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

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

data_tcd542
_database_code_depnum_ccdc_archive 'CCDC 1518826'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_audit_creation_date             2016-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        'Bis(2-picolylamino)zinc perchlorate '
_chemical_formula_moiety         'C12 H16 N4 Zn, 2(Cl O4)'
_chemical_formula_sum            'C12 H16 Cl2 N4 O8 Zn'
_chemical_formula_weight         480.56
_chemical_melting_point          '518 (Decomposition) '
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'
Cl Cl 0.1484 0.1585 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   14.9255(7)
_cell_length_b                   14.9255(7)
_cell_length_c                   15.3140(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3411.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5191
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.806
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0514 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.9000.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21050
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.289
_diffrn_reflns_theta_min         1.905
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'DUO Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX DUO KAPPA'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1832
_reflns_number_total             2120
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'

_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX 3 (Bruker, 2015) '
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'XP (Bruker, 2008-2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+24.8580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          
;
Perchlorate oxygen atoms modelled in two positions with occupancies of 69/31%. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Others
 Sof(O2A)=Sof(O1A)=Sof(O4A)=Sof(O3A)=1-FVAR(1)
 Sof(O1)=Sof(O3)=Sof(O2)=Sof(O4)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Zn1 Zn 0.5000 0.7500 0.40603(4) 0.02716(18) Uani 1 2 d S T P . .
Cl1 Cl 0.29428(6) 0.81765(6) 0.55200(5) 0.02059(19) Uani 1 1 d . . . . .
N4 N 0.40279(19) 0.7106(2) 0.31963(19) 0.0198(6) Uani 1 1 d . . . . .
N1 N 0.4776(2) 0.6301(2) 0.4615(2) 0.0261(7) Uani 1 1 d . . . . .
H1A H 0.5216 0.5910 0.4460 0.031 Uiso 1 1 calc R . . . .
H1B H 0.4777 0.6355 0.5207 0.031 Uiso 1 1 calc R . . . .
C3 C 0.3658(2) 0.6322(2) 0.3430(2) 0.0190(7) Uani 1 1 d . . . . .
C8 C 0.3067(2) 0.5876(3) 0.2869(2) 0.0243(8) Uani 1 1 d . . . . .
H8 H 0.2797 0.5328 0.3041 0.029 Uiso 1 1 calc R . . . .
C2 C 0.3895(2) 0.5962(3) 0.4315(2) 0.0237(8) Uani 1 1 d . . . . .
H2A H 0.3427 0.6140 0.4739 0.028 Uiso 1 1 calc R . . . .
H2B H 0.3911 0.5299 0.4292 0.028 Uiso 1 1 calc R . . . .
C5 C 0.3846(2) 0.7459(3) 0.2408(2) 0.0245(8) Uani 1 1 d . . . . .
H5 H 0.4112 0.8014 0.2251 0.029 Uiso 1 1 calc R . . . .
C6 C 0.3286(3) 0.7041(3) 0.1822(2) 0.0281(9) Uani 1 1 d . . . . .
H6 H 0.3178 0.7294 0.1263 0.034 Uiso 1 1 calc R . . . .
O1 O 0.3721(4) 0.7630(3) 0.5665(4) 0.0410(14) Uani 0.687(8) 1 d . . . A 1
C7 C 0.2884(3) 0.6243(3) 0.2065(3) 0.0294(9) Uani 1 1 d . . . . .
H7 H 0.2483 0.5950 0.1677 0.035 Uiso 1 1 calc R . . . .
O3 O 0.2210(5) 0.7660(5) 0.5224(4) 0.0473(19) Uani 0.687(8) 1 d . . . A 1
O2 O 0.3180(3) 0.8861(3) 0.4876(3) 0.0322(13) Uani 0.687(8) 1 d . . . A 1
O4 O 0.2721(4) 0.8611(4) 0.6328(3) 0.0384(14) Uani 0.687(8) 1 d . . . A 1
O2A O 0.3297(6) 0.8167(9) 0.4666(6) 0.038(4) Uani 0.313(8) 1 d . . . A 2
O1A O 0.3310(9) 0.7405(7) 0.6002(7) 0.033(3) Uani 0.313(8) 1 d . . . A 2
O4A O 0.1957(8) 0.8036(9) 0.5447(9) 0.032(3) Uani 0.313(8) 1 d . . . A 2
O3A O 0.3085(8) 0.8969(6) 0.5974(9) 0.043(3) Uani 0.313(8) 1 d . . . A 2


_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
Zn1 N4 2.050(3) 6_564 ?
Zn1 N4 2.050(3) . ?
Zn1 N1 2.010(3) 6_564 ?
Zn1 N1 2.010(3) . ?
Cl1 O1 1.437(5) . ?
Cl1 O3 1.413(5) . ?
Cl1 O2 1.464(4) . ?
Cl1 O4 1.436(4) . ?
Cl1 O2A 1.410(8) . ?
Cl1 O1A 1.474(10) . ?
Cl1 O4A 1.491(13) . ?
Cl1 O3A 1.388(9) . ?
N4 C3 1.342(5) . ?
N4 C5 1.345(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C2 1.481(5) . ?
C3 C8 1.399(5) . ?
C3 C2 1.501(5) . ?
C8 H8 0.9500 . ?
C8 C7 1.376(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(6) . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Zn1 N4 99.60(17) . 6_564 ?
N1 Zn1 N4 84.22(12) 6_564 6_564 ?
N1 Zn1 N4 84.22(12) . . ?
N1 Zn1 N4 130.27(13) 6_564 . ?
N1 Zn1 N4 130.27(13) . 6_564 ?
N1 Zn1 N1 129.99(19) . 6_564 ?
O1 Cl1 O2 107.8(3) . . ?
O3 Cl1 O1 111.4(4) . . ?
O3 Cl1 O2 110.6(3) . . ?
O3 Cl1 O4 110.2(4) . . ?
O4 Cl1 O1 108.0(3) . . ?
O4 Cl1 O2 108.7(3) . . ?
O2A Cl1 O1A 108.5(6) . . ?
O2A Cl1 O4A 107.4(7) . . ?
O1A Cl1 O4A 107.1(7) . . ?
O3A Cl1 O2A 114.6(7) . . ?
O3A Cl1 O1A 110.9(6) . . ?
O3A Cl1 O4A 108.0(7) . . ?
C3 N4 Zn1 111.7(2) . . ?
C3 N4 C5 119.8(3) . . ?
C5 N4 Zn1 127.6(3) . . ?
Zn1 N1 H1A 110.0 . . ?
Zn1 N1 H1B 110.0 . . ?
H1A N1 H1B 108.3 . . ?
C2 N1 Zn1 108.7(2) . . ?
C2 N1 H1A 110.0 . . ?
C2 N1 H1B 110.0 . . ?
N4 C3 C8 120.7(3) . . ?
N4 C3 C2 117.1(3) . . ?
C8 C3 C2 122.2(3) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 C3 119.0(4) . . ?
C7 C8 H8 120.5 . . ?
N1 C2 C3 111.5(3) . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N4 C5 H5 119.0 . . ?
N4 C5 C6 122.0(4) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.6(4) . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 119.8(4) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?

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
N1 H1A O2 0.91 2.50 3.086(6) 123 6_564
N1 H1A O4 0.91 2.36 3.253(7) 167 4_454
N1 H1A O4A 0.91 2.43 3.014(14) 122 4_454
N1 H1B O1 0.91 2.50 3.404(7) 170 12_767
N1 H1B O4 0.91 2.61 3.168(6) 120 12_767
N1 H1B O1A 0.91 2.19 3.012(10) 150 12_767
C8 H8 O3A 0.95 2.56 3.353(10) 141 14_546
C2 H2B O1A 0.99 2.53 3.290(15) 133 4_454
C2 H2B O3A 0.99 2.37 3.242(11) 146 14_546
C5 H5 O4A 0.95 2.46 3.229(13) 138 7_554
C6 H6 O3 0.95 2.35 3.251(7) 158 13_565

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
Zn1 N4 C3 C8 -171.4(3) . . . . ?
Zn1 N4 C3 C2 9.6(4) . . . . ?
Zn1 N4 C5 C6 168.2(3) . . . . ?
Zn1 N1 C2 C3 27.8(4) . . . . ?
N4 C3 C8 C7 1.4(5) . . . . ?
N4 C3 C2 N1 -25.6(5) . . . . ?
N4 C5 C6 C7 1.6(6) . . . . ?
C3 N4 C5 C6 0.0(5) . . . . ?
C3 C8 C7 C6 0.2(5) . . . . ?
C8 C3 C2 N1 155.5(3) . . . . ?
C2 C3 C8 C7 -179.7(3) . . . . ?
C5 N4 C3 C8 -1.5(5) . . . . ?
C5 N4 C3 C2 179.5(3) . . . . ?
C5 C6 C7 C8 -1.6(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Mitegen holder in oil'
_olex2_submission_original_sample_id L211-Zn(ClO4)-THF
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
####################################################################### 
# 
# 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_tcd440
_database_code_depnum_ccdc_archive 'CCDC 1518829'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_audit_creation_date             2016-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
'5-(2-hydroxyethoxy)-2-{[(2-methylpyridinyl)-E-imino]methyl}phenol '
_chemical_formula_moiety         'C15 H16 N2 O3'
_chemical_formula_sum            'C15 H16 N2 O3'
_chemical_formula_weight         272.30
_chemical_melting_point          397
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.3704(2)
_cell_length_b                   20.0520(5)
_cell_length_c                   12.4990(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.5131(15)
_cell_angle_gamma                90
_cell_volume                     1323.39(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.100
_cell_measurement_theta_min      2.622
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0645 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9184.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             576
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32488
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         33.144
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST Eco'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3656
_reflns_number_total             5038
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'

_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX 3 (Bruker, 2015) '
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'XP (Bruker, 2008-2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         5038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.5059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1271
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N1 N -0.25555(18) 0.49762(5) 0.28308(8) 0.01626(19) Uani 1 1 d . . . . .
C2 C -0.2518(2) 0.56238(6) 0.31076(10) 0.0186(2) Uani 1 1 d . . . . .
H2 H -0.3998 0.5882 0.2869 0.022 Uiso 1 1 calc R . . . .
C3 C -0.0434(2) 0.59332(6) 0.37217(10) 0.0193(2) Uani 1 1 d . . . . .
H3 H -0.0482 0.6392 0.3904 0.023 Uiso 1 1 calc R . . . .
C4 C 0.1720(2) 0.55564(6) 0.40624(10) 0.0196(2) Uani 1 1 d . . . . .
H4 H 0.3185 0.5753 0.4485 0.024 Uiso 1 1 calc R . . . .
C5 C 0.1718(2) 0.48889(6) 0.37815(10) 0.0175(2) Uani 1 1 d . . . . .
H5 H 0.3183 0.4623 0.4005 0.021 Uiso 1 1 calc R . . . .
C6 C -0.0460(2) 0.46135(5) 0.31672(9) 0.0137(2) Uani 1 1 d . . . . .
C7 C -0.0632(2) 0.38956(5) 0.28120(9) 0.0160(2) Uani 1 1 d . . . . .
H7A H -0.2291 0.3712 0.2906 0.019 Uiso 1 1 calc R . . . .
H7B H -0.0540 0.3871 0.2029 0.019 Uiso 1 1 calc R . . . .
N8 N 0.13846(18) 0.34908(5) 0.34288(8) 0.01513(18) Uani 1 1 d . . . . .
C9 C 0.2551(2) 0.30743(5) 0.29161(9) 0.0140(2) Uani 1 1 d . . . . .
H9 H 0.2080 0.3036 0.2148 0.017 Uiso 1 1 calc R . . . .
C10 C 0.4580(2) 0.26603(5) 0.34911(8) 0.01221(19) Uani 1 1 d . . . . .
C11 C 0.5409(2) 0.27274(5) 0.46275(8) 0.01314(19) Uani 1 1 d . . . . .
C12 C 0.7422(2) 0.23504(5) 0.51561(8) 0.0147(2) Uani 1 1 d . . . . .
H12 H 0.7994 0.2404 0.5916 0.018 Uiso 1 1 calc R . . . .
C13 C 0.8613(2) 0.18931(5) 0.45774(9) 0.0134(2) Uani 1 1 d . . . . .
C14 C 0.7804(2) 0.18095(6) 0.34564(9) 0.0143(2) Uani 1 1 d . . . . .
H14 H 0.8603 0.1494 0.3063 0.017 Uiso 1 1 calc R . . . .
C15 C 0.5808(2) 0.21974(5) 0.29322(9) 0.0137(2) Uani 1 1 d . . . . .
H15 H 0.5259 0.2147 0.2170 0.016 Uiso 1 1 calc R . . . .
O16 O 0.42686(17) 0.31598(4) 0.52110(7) 0.01826(18) Uani 1 1 d . . . . .
H16 H 0.293(4) 0.3341(11) 0.4714(18) 0.051(6) Uiso 1 1 d . . . . .
O17 O 1.05459(16) 0.15491(4) 0.51851(6) 0.01725(17) Uani 1 1 d . . . . .
C18 C 1.1903(2) 0.10718(6) 0.46512(9) 0.0166(2) Uani 1 1 d . . . . .
H18A H 1.2555 0.1286 0.4044 0.020 Uiso 1 1 calc R . . . .
H18B H 1.0772 0.0700 0.4354 0.020 Uiso 1 1 calc R . . . .
C19 C 1.4058(2) 0.08171(6) 0.54903(10) 0.0181(2) Uani 1 1 d . . . . .
H19A H 1.5236 0.0556 0.5131 0.022 Uiso 1 1 calc R . . . .
H19B H 1.5004 0.1197 0.5874 0.022 Uiso 1 1 calc R . . . .
O20 O 1.30967(18) 0.04095(5) 0.62475(8) 0.0225(2) Uani 1 1 d . . . . .
H20 H 1.441(4) 0.0311(10) 0.6763(17) 0.040(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3430(15) . ?
N1 C6 1.3414(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3831(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3824(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3836(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3909(16) . ?
C6 C7 1.5043(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N8 1.4567(14) . ?
N8 C9 1.2834(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.4517(15) . ?
C10 C11 1.4152(14) . ?
C10 C15 1.3971(15) . ?
C11 C12 1.3844(15) . ?
C11 O16 1.3497(13) . ?
C12 H12 0.9500 . ?
C12 C13 1.3934(15) . ?
C13 C14 1.3992(14) . ?
C13 O17 1.3576(13) . ?
C14 H14 0.9500 . ?
C14 C15 1.3883(15) . ?
C15 H15 0.9500 . ?
O16 H16 0.93(2) . ?
O17 C18 1.4386(14) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5024(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 O20 1.4172(15) . ?
O20 H20 0.89(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
C6 N1 C2 118.11(10) . . ?
N1 C2 H2 118.3 . . ?
N1 C2 C3 123.31(11) . . ?
C3 C2 H2 118.3 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.21(11) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.25(11) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.07(11) . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 122.05(10) . . ?
N1 C6 C7 115.04(10) . . ?
C5 C6 C7 122.90(10) . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N8 C7 C6 112.17(9) . . ?
N8 C7 H7A 109.2 . . ?
N8 C7 H7B 109.2 . . ?
C9 N8 C7 118.82(10) . . ?
N8 C9 H9 119.5 . . ?
N8 C9 C10 121.04(10) . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.84(10) . . ?
C15 C10 C9 120.82(9) . . ?
C15 C10 C11 118.32(10) . . ?
C12 C11 C10 120.15(10) . . ?
O16 C11 C10 120.86(10) . . ?
O16 C11 C12 118.99(9) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.26(10) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 120.71(10) . . ?
O17 C13 C12 114.86(9) . . ?
O17 C13 C14 124.43(10) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.51(10) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 122.03(10) . . ?
C14 C15 H15 119.0 . . ?
C11 O16 H16 105.1(13) . . ?
C13 O17 C18 118.61(8) . . ?
O17 C18 H18A 110.3 . . ?
O17 C18 H18B 110.3 . . ?
O17 C18 C19 107.04(9) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
O20 C19 C18 109.52(10) . . ?
O20 C19 H19A 109.8 . . ?
O20 C19 H19B 109.8 . . ?
C19 O20 H20 106.0(13) . . ?

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
C3 H3 O16 0.95 2.64 3.2140(15) 119 3_566
C7 H7B O17 0.99 2.62 3.5685(15) 161 4_465
C9 H9 O17 0.95 2.58 3.4699(13) 156 4_465
O16 H16 N8 0.93(2) 1.70(2) 2.5578(12) 152(2) .
O20 H20 N1 0.89(2) 2.00(2) 2.8775(13) 174.6(19) 4_766

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
N1 C2 C3 C4 0.31(18) . . . . ?
N1 C6 C7 N8 -164.52(10) . . . . ?
C2 N1 C6 C5 -0.30(16) . . . . ?
C2 N1 C6 C7 -179.14(10) . . . . ?
C2 C3 C4 C5 -0.08(18) . . . . ?
C3 C4 C5 C6 -0.31(18) . . . . ?
C4 C5 C6 N1 0.51(17) . . . . ?
C4 C5 C6 C7 179.26(11) . . . . ?
C5 C6 C7 N8 16.65(16) . . . . ?
C6 N1 C2 C3 -0.12(17) . . . . ?
C6 C7 N8 C9 -135.51(11) . . . . ?
C7 N8 C9 C10 179.82(10) . . . . ?
N8 C9 C10 C11 -3.04(16) . . . . ?
N8 C9 C10 C15 178.61(10) . . . . ?
C9 C10 C11 C12 -177.06(10) . . . . ?
C9 C10 C11 O16 2.56(16) . . . . ?
C9 C10 C15 C14 178.01(10) . . . . ?
C10 C11 C12 C13 -1.29(17) . . . . ?
C11 C10 C15 C14 -0.38(16) . . . . ?
C11 C12 C13 C14 0.27(17) . . . . ?
C11 C12 C13 O17 -179.45(10) . . . . ?
C12 C13 C14 C15 0.67(17) . . . . ?
C12 C13 O17 C18 -179.26(10) . . . . ?
C13 C14 C15 C10 -0.61(17) . . . . ?
C13 O17 C18 C19 174.90(9) . . . . ?
C14 C13 O17 C18 1.03(16) . . . . ?
C15 C10 C11 C12 1.34(16) . . . . ?
C15 C10 C11 O16 -179.04(10) . . . . ?
O16 C11 C12 C13 179.08(10) . . . . ?
O17 C13 C14 C15 -179.63(10) . . . . ?
O17 C18 C19 O20 70.49(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in oil'
_olex2_submission_original_sample_id L221
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_tcd375
_database_code_depnum_ccdc_archive 'CCDC 1518825'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Cis-dichloro(N-[4-(hydroxyphenyl)methyl]-2-pyridinemethamino)copper '
_chemical_name_common            ?
_chemical_melting_point          451
_chemical_formula_moiety         'C30 H34 Cl4 Cu2 N6 O2, C26 H28 Cl4 Cu2 N4 O2'
_chemical_formula_sum            'C56 H62 Cl8 Cu4 N10 O4'
_chemical_formula_weight         1476.91

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   11.9914(6)
_cell_length_b                   12.6755(6)
_cell_length_c                   12.6960(6)
_cell_angle_alpha                113.9980(10)
_cell_angle_beta                 96.5800(10)
_cell_angle_gamma                115.3470(10)
_cell_volume                     1492.64(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9795
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      30.10

_exptl_crystal_description       fragment
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.819
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6898
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker, 2014/5) was used for absorption correction.
wR2(int) was 0.0472 before and 0.0380 after correction.
The Ratio of minimum to maximum transmission is 0.925.
The λ/2 correction factor is 0.00150.
;

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.258
_diffrn_reflns_number            58825
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.874
_diffrn_reflns_theta_max         30.211
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8816
_reflns_number_gt                7707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker, 2014)'
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008-2014)'
_computing_publication_material  'SHELXTL (Bruker, 2008-2014)'

_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)+(0.0273P)²+0.7451P] 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         8816
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0572
_refine_ls_wR_factor_gt          0.0542
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C2 C 0.31742(13) 0.84895(14) 0.73585(13) 0.0162(2) Uani 1 1 d . . . . .
H2 H 0.2420 0.8500 0.7055 0.019 Uiso 1 1 calc R U . . .
C3 C 0.33687(14) 0.84328(14) 0.84248(13) 0.0180(3) Uani 1 1 d . . . . .
H3 H 0.2759 0.8406 0.8845 0.022 Uiso 1 1 calc R U . . .
C4 C 0.44737(14) 0.84157(14) 0.88720(12) 0.0178(3) Uani 1 1 d . . . . .
H4 H 0.4622 0.8361 0.9595 0.021 Uiso 1 1 calc R U . . .
C5 C 0.53550(13) 0.84794(14) 0.82439(12) 0.0161(2) Uani 1 1 d . . . . .
H5 H 0.6123 0.8484 0.8538 0.019 Uiso 1 1 calc R U . . .
C6 C 0.50947(12) 0.85367(13) 0.71776(12) 0.0132(2) Uani 1 1 d . . . . .
C7 C 0.60456(13) 0.86879(15) 0.65008(12) 0.0155(2) Uani 1 1 d . . . . .
H7A H 0.6767 0.9649 0.6923 0.019 Uiso 1 1 calc R U . . .
H7B H 0.6437 0.8143 0.6510 0.019 Uiso 1 1 calc R U . . .
C9 C 0.50975(13) 0.68718(14) 0.43184(13) 0.0163(2) Uani 1 1 d . . . . .
H9A H 0.4669 0.6642 0.3478 0.020 Uiso 1 1 calc R U . . .
H9B H 0.4466 0.6199 0.4487 0.020 Uiso 1 1 calc R U . . .
C10 C 0.63074(13) 0.67547(14) 0.43553(12) 0.0145(2) Uani 1 1 d . . . . .
C11 C 0.61948(13) 0.55170(14) 0.40738(12) 0.0160(2) Uani 1 1 d . . . . .
H11 H 0.5360 0.4761 0.3865 0.019 Uiso 1 1 calc R U . . .
C12 C 0.72834(14) 0.53743(14) 0.40945(13) 0.0168(2) Uani 1 1 d . . . . .
H12 H 0.7188 0.4524 0.3889 0.020 Uiso 1 1 calc R U . . .
C13 C 0.85139(13) 0.64845(14) 0.44173(12) 0.0153(2) Uani 1 1 d . . . . .
C14 C 0.86463(13) 0.77235(14) 0.47003(12) 0.0158(2) Uani 1 1 d . . . . .
H14 H 0.9484 0.8481 0.4918 0.019 Uiso 1 1 calc R U . . .
C15 C 0.75457(13) 0.78492(14) 0.46627(12) 0.0164(2) Uani 1 1 d . . . . .
H15 H 0.7640 0.8696 0.4850 0.020 Uiso 1 1 calc R U . . .
C17 C 0.12532(13) 0.51709(14) 0.36542(12) 0.0162(2) Uani 1 1 d . . . . .
C18 C 0.00112(14) 0.38884(14) 0.31129(13) 0.0202(3) Uani 1 1 d . . . . .
H18A H -0.0431 0.3905 0.3717 0.030 Uiso 1 1 calc R U . . .
H18B H 0.0181 0.3148 0.2870 0.030 Uiso 1 1 calc R U . . .
H18C H -0.0552 0.3749 0.2386 0.030 Uiso 1 1 calc R U . . .
C20 C 0.38477(13) 0.34051(14) 1.07188(13) 0.0182(3) Uani 1 1 d . . . . .
H20 H 0.3979 0.3819 1.1573 0.022 Uiso 1 1 calc R U . . .
C21 C 0.49254(14) 0.38084(16) 1.03523(15) 0.0223(3) Uani 1 1 d . . . . .
H21 H 0.5783 0.4491 1.0943 0.027 Uiso 1 1 calc R U . . .
C22 C 0.47267(15) 0.31931(17) 0.90998(15) 0.0245(3) Uani 1 1 d . . . . .
H22 H 0.5452 0.3437 0.8824 0.029 Uiso 1 1 calc R U . . .
C23 C 0.34646(15) 0.22256(16) 0.82634(14) 0.0221(3) Uani 1 1 d . . . . .
H23 H 0.3310 0.1802 0.7405 0.027 Uiso 1 1 calc R U . . .
C24 C 0.24223(14) 0.18795(14) 0.86936(12) 0.0164(2) Uani 1 1 d . . . . .
C25 C 0.10232(14) 0.08214(15) 0.78373(12) 0.0184(3) Uani 1 1 d . . . . .
H25A H 0.0827 0.0984 0.7158 0.022 Uiso 1 1 calc R U . . .
H25B H 0.0917 -0.0086 0.7474 0.022 Uiso 1 1 calc R U . . .
C27 C -0.05707(13) 0.15663(14) 0.83008(12) 0.0159(2) Uani 1 1 d . . . . .
H27A H -0.1300 0.1388 0.8629 0.019 Uiso 1 1 calc R U . . .
H27B H -0.0957 0.1189 0.7407 0.019 Uiso 1 1 calc R U . . .
C28 C 0.03529(13) 0.30756(14) 0.89115(12) 0.0147(2) Uani 1 1 d . . . . .
C29 C 0.07460(13) 0.39231(14) 1.01827(12) 0.0155(2) Uani 1 1 d . . . . .
H29 H 0.0444 0.3534 1.0669 0.019 Uiso 1 1 calc R U . . .
C30 C 0.15653(13) 0.53172(14) 1.07471(12) 0.0158(2) Uani 1 1 d . . . . .
H30 H 0.1833 0.5876 1.1612 0.019 Uiso 1 1 calc R U . . .
C31 C 0.19925(13) 0.58893(14) 1.00266(12) 0.0153(2) Uani 1 1 d . . . . .
C32 C 0.16223(14) 0.50671(14) 0.87636(12) 0.0178(3) Uani 1 1 d . . . . .
H32 H 0.1926 0.5456 0.8277 0.021 Uiso 1 1 calc R U . . .
C33 C 0.08029(14) 0.36699(14) 0.82177(12) 0.0174(3) Uani 1 1 d . . . . .
H33 H 0.0546 0.3111 0.7354 0.021 Uiso 1 1 calc R U . . .
Cl1 Cl 0.40313(3) 0.86259(3) 0.33793(3) 0.01670(6) Uani 1 1 d . . . . .
Cl2 Cl 0.22082(3) 0.90499(3) 0.51649(3) 0.01738(6) Uani 1 1 d . . . . .
Cl3 Cl 0.20740(3) 0.25199(3) 1.23160(3) 0.01719(6) Uani 1 1 d . . . . .
Cl4 Cl -0.10410(3) 0.07107(3) 1.04803(3) 0.01556(6) Uani 1 1 d . . . . .
Cu1 Cu 0.37876(2) 0.84601(2) 0.50967(2) 0.01257(4) Uani 1 1 d . . . . .
Cu2 Cu 0.10025(2) 0.15874(2) 1.02979(2) 0.01307(4) Uani 1 1 d . . . . .
N1 N 0.40141(11) 0.85298(11) 0.67337(10) 0.0132(2) Uani 1 1 d . . . . .
N8 N 0.53821(11) 0.82380(12) 0.52126(10) 0.0127(2) Uani 1 1 d . . . . .
N16 N 0.22158(12) 0.61839(13) 0.40765(12) 0.0203(2) Uani 1 1 d . . . . .
N19 N 0.26168(11) 0.24442(11) 0.99041(10) 0.0152(2) Uani 1 1 d . . . . .
N26 N 0.00824(11) 0.08494(12) 0.84912(10) 0.0153(2) Uani 1 1 d . . . . .
O1 O 0.95620(10) 0.63005(11) 0.44349(10) 0.0190(2) Uani 1 1 d . . . . .
H1 H 1.0254 0.7040 0.4673 0.028 Uiso 1 1 calc R U . . .
O2 O 0.27625(10) 0.72628(10) 1.05189(9) 0.0204(2) Uani 1 1 d . . . . .
H2A H 0.3021 0.7650 1.1290 0.031 Uiso 1 1 calc R U . . .
H8 H 0.5886(17) 0.8834(18) 0.5049(16) 0.016(4) Uiso 1 1 d . . . . .
H26 H -0.0524(19) 0.003(2) 0.8232(17) 0.023(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 N1 1.3484(16) . ?
C2 C3 1.3834(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3930(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3899(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3922(18) . ?
C5 H5 0.9500 . ?
C6 N1 1.3474(16) . ?
C6 C7 1.4988(18) . ?
C7 N8 1.4792(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 N8 1.4866(17) . ?
C9 C10 1.5177(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.3946(19) . ?
C10 C11 1.3995(18) . ?
C11 C12 1.3912(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3928(19) . ?
C12 H12 0.9500 . ?
C13 O1 1.3723(15) . ?
C13 C14 1.3913(19) . ?
C14 C15 1.3932(18) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 N16 1.1392(18) . ?
C17 C18 1.4549(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 N19 1.3484(18) . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.3910(19) . ?
C23 H23 0.9500 . ?
C24 N19 1.3449(17) . ?
C24 C25 1.505(2) . ?
C25 N26 1.4793(17) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C27 N26 1.4974(17) . ?
C27 C28 1.5068(19) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C33 1.3911(19) . ?
C28 C29 1.4010(18) . ?
C29 C30 1.3869(19) . ?
C29 H29 0.9500 . ?
C30 C31 1.3979(18) . ?
C30 H30 0.9500 . ?
C31 O2 1.3712(17) . ?
C31 C32 1.3913(18) . ?
C32 C33 1.392(2) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
Cl1 Cu1 2.3130(4) . ?
Cl2 Cu1 2.3130(3) . ?
Cl3 Cu2 2.2571(4) . ?
Cl4 Cu2 2.3024(4) . ?
Cl4 Cu2 2.6922(4) 2_557 ?
Cu1 N1 2.0254(11) . ?
Cu1 N8 2.0463(11) . ?
Cu1 N16 2.3020(13) . ?
Cu2 N19 2.0101(12) . ?
Cu2 N26 2.0358(11) . ?
Cu2 Cl4 2.6922(4) 2_557 ?
N8 H8 0.863(18) . ?
N26 H26 0.854(19) . ?
O1 H1 0.8400 . ?
O2 H2A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 C3 122.53(12) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 118.86(12) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.93(12) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 118.96(12) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 122.09(12) . . ?
N1 C6 C7 116.38(11) . . ?
C5 C6 C7 121.44(11) . . ?
N8 C7 C6 111.04(10) . . ?
N8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N8 C9 C10 114.00(11) . . ?
N8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
C15 C10 C11 118.17(12) . . ?
C15 C10 C9 122.06(12) . . ?
C11 C10 C9 119.77(12) . . ?
C12 C11 C10 121.21(12) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.68(12) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
O1 C13 C14 122.30(12) . . ?
O1 C13 C12 117.72(12) . . ?
C14 C13 C12 119.98(12) . . ?
C13 C14 C15 119.77(12) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 121.18(12) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
N16 C17 C18 179.01(15) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N19 C20 C21 122.16(13) . . ?
N19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C20 C21 C22 118.62(14) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C23 C22 C21 119.30(14) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 119.13(14) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
N19 C24 C23 121.64(13) . . ?
N19 C24 C25 116.24(12) . . ?
C23 C24 C25 122.08(13) . . ?
N26 C25 C24 111.28(11) . . ?
N26 C25 H25A 109.4 . . ?
C24 C25 H25A 109.4 . . ?
N26 C25 H25B 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
N26 C27 C28 113.40(11) . . ?
N26 C27 H27A 108.9 . . ?
C28 C27 H27A 108.9 . . ?
N26 C27 H27B 108.9 . . ?
C28 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C33 C28 C29 118.17(12) . . ?
C33 C28 C27 120.65(12) . . ?
C29 C28 C27 121.15(12) . . ?
C30 C29 C28 121.53(12) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C29 C30 C31 119.13(12) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
O2 C31 C32 117.53(12) . . ?
O2 C31 C30 122.11(12) . . ?
C32 C31 C30 120.35(13) . . ?
C31 C32 C33 119.50(12) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C28 C33 C32 121.30(12) . . ?
C28 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
Cu2 Cl4 Cu2 84.542(11) . 2_557 ?
N1 Cu1 N8 82.60(4) . . ?
N1 Cu1 N16 90.95(5) . . ?
N8 Cu1 N16 96.18(4) . . ?
N1 Cu1 Cl2 95.76(3) . . ?
N8 Cu1 Cl2 171.50(3) . . ?
N16 Cu1 Cl2 92.18(3) . . ?
N1 Cu1 Cl1 167.32(3) . . ?
N8 Cu1 Cl1 86.94(3) . . ?
N16 Cu1 Cl1 97.32(3) . . ?
Cl2 Cu1 Cl1 93.526(13) . . ?
N19 Cu2 N26 82.25(5) . . ?
N19 Cu2 Cl3 95.98(3) . . ?
N26 Cu2 Cl3 176.89(4) . . ?
N19 Cu2 Cl4 167.96(3) . . ?
N26 Cu2 Cl4 88.26(3) . . ?
Cl3 Cu2 Cl4 93.148(13) . . ?
N19 Cu2 Cl4 91.29(3) . 2_557 ?
N26 Cu2 Cl4 86.06(3) . 2_557 ?
Cl3 Cu2 Cl4 96.558(12) . 2_557 ?
Cl4 Cu2 Cl4 95.459(11) . 2_557 ?
C6 N1 C2 118.62(11) . . ?
C6 N1 Cu1 114.24(8) . . ?
C2 N1 Cu1 127.02(9) . . ?
C7 N8 C9 113.03(10) . . ?
C7 N8 Cu1 109.53(8) . . ?
C9 N8 Cu1 114.73(8) . . ?
C7 N8 H8 107.4(12) . . ?
C9 N8 H8 110.4(11) . . ?
Cu1 N8 H8 100.8(11) . . ?
C17 N16 Cu1 163.95(11) . . ?
C24 N19 C20 119.10(12) . . ?
C24 N19 Cu2 114.06(9) . . ?
C20 N19 Cu2 126.53(9) . . ?
C25 N26 C27 114.14(11) . . ?
C25 N26 Cu2 108.80(8) . . ?
C27 N26 Cu2 113.25(8) . . ?
C25 N26 H26 108.6(13) . . ?
C27 N26 H26 107.4(12) . . ?
Cu2 N26 H26 104.1(12) . . ?
C13 O1 H1 109.5 . . ?
C31 O2 H2A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 N1 -0.1(2) . . . . ?
C4 C5 C6 C7 176.40(13) . . . . ?
N1 C6 C7 N8 -23.73(16) . . . . ?
C5 C6 C7 N8 159.56(12) . . . . ?
N8 C9 C10 C15 -31.24(18) . . . . ?
N8 C9 C10 C11 148.82(12) . . . . ?
C15 C10 C11 C12 -0.2(2) . . . . ?
C9 C10 C11 C12 179.75(12) . . . . ?
C10 C11 C12 C13 0.9(2) . . . . ?
C11 C12 C13 O1 179.51(12) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
O1 C13 C14 C15 179.76(12) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C10 0.5(2) . . . . ?
C11 C10 C15 C14 -0.5(2) . . . . ?
C9 C10 C15 C14 179.52(12) . . . . ?
N19 C20 C21 C22 -0.3(2) . . . . ?
C20 C21 C22 C23 1.4(2) . . . . ?
C21 C22 C23 C24 -0.6(2) . . . . ?
C22 C23 C24 N19 -1.3(2) . . . . ?
C22 C23 C24 C25 -179.20(13) . . . . ?
N19 C24 C25 N26 14.18(17) . . . . ?
C23 C24 C25 N26 -167.86(13) . . . . ?
N26 C27 C28 C33 105.20(14) . . . . ?
N26 C27 C28 C29 -77.02(15) . . . . ?
C33 C28 C29 C30 -0.3(2) . . . . ?
C27 C28 C29 C30 -178.11(12) . . . . ?
C28 C29 C30 C31 0.9(2) . . . . ?
C29 C30 C31 O2 177.50(12) . . . . ?
C29 C30 C31 C32 -1.4(2) . . . . ?
O2 C31 C32 C33 -177.76(12) . . . . ?
C30 C31 C32 C33 1.1(2) . . . . ?
C29 C28 C33 C32 0.0(2) . . . . ?
C27 C28 C33 C32 177.90(12) . . . . ?
C31 C32 C33 C28 -0.5(2) . . . . ?
C5 C6 N1 C2 1.16(19) . . . . ?
C7 C6 N1 C2 -175.53(12) . . . . ?
C5 C6 N1 Cu1 -175.07(10) . . . . ?
C7 C6 N1 Cu1 8.24(15) . . . . ?
C3 C2 N1 C6 -1.1(2) . . . . ?
C3 C2 N1 Cu1 174.61(10) . . . . ?
C6 C7 N8 C9 -102.46(13) . . . . ?
C6 C7 N8 Cu1 26.81(13) . . . . ?
C10 C9 N8 C7 -57.60(15) . . . . ?
C10 C9 N8 Cu1 175.85(9) . . . . ?
C23 C24 N19 C20 2.4(2) . . . . ?
C25 C24 N19 C20 -179.59(12) . . . . ?
C23 C24 N19 Cu2 -171.50(11) . . . . ?
C25 C24 N19 Cu2 6.47(15) . . . . ?
C21 C20 N19 C24 -1.6(2) . . . . ?
C21 C20 N19 Cu2 171.51(10) . . . . ?
C24 C25 N26 C27 100.60(13) . . . . ?
C24 C25 N26 Cu2 -26.95(13) . . . . ?
C28 C27 N26 C25 -69.46(14) . . . . ?
C28 C27 N26 Cu2 55.78(13) . . . . ?

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
C2 H2 Cl2 0.95 2.77 3.3431(14) 120 .
C3 H3 Cl4 0.95 2.80 3.6274(14) 146 2_567
C7 H7B Cl3 0.99 2.79 3.7061(13) 153 2_667
C18 H18B Cl3 0.98 2.78 3.6015(15) 142 1_554
C20 H20 Cl3 0.95 2.71 3.2697(15) 118 .
O1 H1 Cl2 0.84 2.37 3.2099(11) 175 1_655
O2 H2A Cl1 0.84 2.31 3.1412(11) 170 1_556
N8 H8 Cl2 0.863(18) 2.825(18) 3.6810(12) 172.1(15) 2_676
N26 H26 Cl3 0.854(19) 2.672(19) 3.5147(12) 169.1(16) 2_557

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.062


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_tcd437
_database_code_depnum_ccdc_archive 'CCDC 1518827'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_audit_creation_date             2016-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
4-{[(2-methylpyridinyl)-E-imino]methyl}-benzene-1,3-diol
_chemical_formula_moiety         'C13 H12 N2 O2'
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_chemical_melting_point          433
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   22.8835(13)
_cell_length_b                   5.7669(3)
_cell_length_c                   18.6703(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.5980(15)
_cell_angle_gamma                90
_cell_volume                     2274.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6350
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      3.58
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0534 before and 0.0437 after correction.
The Ratio of minimum to maximum transmission is 0.9488.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             960
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8049
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.260
_diffrn_reflns_theta_min         3.580
_diffrn_ambient_temperature      99.92
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST Eco'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2250
_reflns_number_total             2810
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'

_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX 3 (Bruker, 2015) '
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'XP (Bruker, 2008-2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0049(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+1.9147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N1 N 0.58499(5) 0.71258(19) 0.92775(6) 0.0204(2) Uani 1 1 d . . . . .
O1 O 0.62545(4) 1.00231(15) 0.71896(5) 0.0210(2) Uani 1 1 d . . . . .
C2 C 0.52741(7) 0.7143(2) 0.93096(8) 0.0260(3) Uani 1 1 d . . . . .
H2 H 0.5167 0.8406 0.9562 0.031 Uiso 1 1 calc R . . . .
O2 O 0.67251(4) 0.95174(16) 0.49179(5) 0.0227(2) Uani 1 1 d . . . . .
C3 C 0.48306(6) 0.5428(3) 0.89961(8) 0.0281(3) Uani 1 1 d . . . . .
H3 H 0.4429 0.5502 0.9034 0.034 Uiso 1 1 calc R . . . .
C4 C 0.49848(7) 0.3594(3) 0.86245(8) 0.0303(3) Uani 1 1 d . . . . .
H4 H 0.4690 0.2382 0.8400 0.036 Uiso 1 1 calc R . . . .
C5 C 0.55773(7) 0.3557(2) 0.85849(8) 0.0268(3) Uani 1 1 d . . . . .
H5 H 0.5695 0.2315 0.8334 0.032 Uiso 1 1 calc R . . . .
C6 C 0.59960(6) 0.5351(2) 0.89157(7) 0.0174(3) Uani 1 1 d . . . . .
C7 C 0.66392(6) 0.5416(2) 0.88674(7) 0.0201(3) Uani 1 1 d . . . . .
H7A H 0.6943 0.6233 0.9325 0.024 Uiso 1 1 calc R . . . .
H7B H 0.6795 0.3815 0.8866 0.024 Uiso 1 1 calc R . . . .
N8 N 0.65956(5) 0.66177(18) 0.81565(6) 0.0182(2) Uani 1 1 d . . . . .
C9 C 0.68139(5) 0.5578(2) 0.77028(7) 0.0158(2) Uani 1 1 d . . . . .
H9 H 0.6991 0.4073 0.7835 0.019 Uiso 1 1 calc R . . . .
C10 C 0.67949(5) 0.6657(2) 0.69922(6) 0.0150(2) Uani 1 1 d . . . . .
C11 C 0.65047(5) 0.8842(2) 0.67507(7) 0.0157(2) Uani 1 1 d . . . . .
C12 C 0.64714(6) 0.9804(2) 0.60509(7) 0.0171(3) Uani 1 1 d . . . . .
H12 H 0.6268 1.1255 0.5885 0.021 Uiso 1 1 calc R . . . .
C13 C 0.67366(6) 0.8638(2) 0.55949(7) 0.0170(2) Uani 1 1 d . . . . .
C14 C 0.70402(6) 0.6495(2) 0.58371(7) 0.0180(3) Uani 1 1 d . . . . .
H14 H 0.7229 0.5716 0.5532 0.022 Uiso 1 1 calc R . . . .
C15 C 0.70602(5) 0.5539(2) 0.65212(7) 0.0165(2) Uani 1 1 d . . . . .
H15 H 0.7260 0.4077 0.6679 0.020 Uiso 1 1 calc R . . . .
H2A H 0.6413(9) 1.070(4) 0.4730(11) 0.050(5) Uiso 1 1 d . . . . .
H1 H 0.6318(10) 0.909(4) 0.7639(12) 0.057(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3419(17) . ?
N1 C6 1.3375(16) . ?
O1 C11 1.3506(14) . ?
O1 H1 0.96(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(2) . ?
O2 C13 1.3527(14) . ?
O2 H2A 0.95(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3838(18) . ?
C6 C7 1.5093(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N8 1.4665(15) . ?
N8 C9 1.2851(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.4509(16) . ?
C10 C11 1.4146(16) . ?
C10 C15 1.4030(16) . ?
C11 C12 1.3942(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3937(16) . ?
C13 C14 1.4047(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3756(16) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 117.94(11) . . ?
C11 O1 H1 106.9(12) . . ?
N1 C2 H2 118.2 . . ?
N1 C2 C3 123.50(13) . . ?
C3 C2 H2 118.2 . . ?
C13 O2 H2A 110.8(11) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.31(12) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.82(13) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.23(13) . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 122.20(12) . . ?
N1 C6 C7 116.75(11) . . ?
C5 C6 C7 121.03(12) . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N8 C7 C6 109.69(10) . . ?
N8 C7 H7A 109.7 . . ?
N8 C7 H7B 109.7 . . ?
C9 N8 C7 117.87(11) . . ?
N8 C9 H9 119.3 . . ?
N8 C9 C10 121.33(11) . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 121.25(10) . . ?
C15 C10 C9 120.52(11) . . ?
C15 C10 C11 118.22(10) . . ?
O1 C11 C10 120.82(10) . . ?
O1 C11 C12 118.99(11) . . ?
C12 C11 C10 120.19(11) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.06(11) . . ?
C13 C12 H12 120.0 . . ?
O2 C13 C12 122.24(11) . . ?
O2 C13 C14 117.41(11) . . ?
C12 C13 C14 120.34(11) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.18(11) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 121.97(11) . . ?
C14 C15 H15 119.0 . . ?

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
O2 H2A N1 0.95(2) 1.76(2) 2.7106(14) 173.1(17) 6_575
O1 H1 N8 0.96(2) 1.70(2) 2.5772(13) 149.8(18) .

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
N1 C2 C3 C4 -0.4(2) . . . . ?
N1 C6 C7 N8 -90.03(13) . . . . ?
O1 C11 C12 C13 178.80(11) . . . . ?
C2 N1 C6 C5 -0.48(18) . . . . ?
C2 N1 C6 C7 178.19(11) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
O2 C13 C14 C15 -179.78(11) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 N1 0.3(2) . . . . ?
C4 C5 C6 C7 -178.32(12) . . . . ?
C5 C6 C7 N8 88.65(14) . . . . ?
C6 N1 C2 C3 0.51(19) . . . . ?
C6 C7 N8 C9 -127.39(12) . . . . ?
C7 N8 C9 C10 -179.36(10) . . . . ?
N8 C9 C10 C11 -3.46(18) . . . . ?
N8 C9 C10 C15 177.23(11) . . . . ?
C9 C10 C11 O1 2.21(17) . . . . ?
C9 C10 C11 C12 -177.58(11) . . . . ?
C9 C10 C15 C14 178.82(11) . . . . ?
C10 C11 C12 C13 -1.41(18) . . . . ?
C11 C10 C15 C14 -0.52(17) . . . . ?
C11 C12 C13 O2 -178.94(11) . . . . ?
C11 C12 C13 C14 -0.18(18) . . . . ?
C12 C13 C14 C15 1.40(18) . . . . ?
C13 C14 C15 C10 -1.04(18) . . . . ?
C15 C10 C11 O1 -178.46(10) . . . . ?
C15 C10 C11 C12 1.74(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in oil'
_olex2_submission_original_sample_id L211
_olex2_submission_special_instructions 'No special instructions were received'
