# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_nc124-a
_database_code_depnum_ccdc_archive 'CCDC 2010597'
loop_
_audit_author_name
_audit_author_address
'Francois Michaud'
;Universite de Brest plateforme DRX
France
;
_audit_update_record             
;
2020-06-18 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

_audit_creation_date             2012-02-13T18:02:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
2-(1,4,8,11-tetraazatricyclo[9.3.1.14,8]hexadec-6-yl)ethanol
_chemical_formula_moiety         
;
        C14 H28 N4 O
;
_chemical_formula_sum            'C14 H28 N4 O'
_chemical_formula_weight         268.4

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4724(6)
_cell_length_b                   8.8104(6)
_cell_length_c                   10.4428(7)
_cell_angle_alpha                102.601(6)
_cell_angle_beta                 95.879(6)
_cell_angle_gamma                107.157(6)
_cell_volume                     715.16(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2033
_cell_measurement_theta_min      2.9307
_cell_measurement_theta_max      31.4917

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       'planar // (0 1 0)'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.01
0 -2 -1 0.03
1 -1 -2 0.1
0 0 1 0.09
-1 1 -2 0.055
1 -1 2 0.055
0 1 -1 0.08
0 -1 1 0.07
1 -1 1 0.065
-1 1 -1 0.055
0 1 0 0.04
_exptl_crystal_recrystallization_method 
;
Slow evaporation of aqueous solution at room temperature
;

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_T_max  0.9960

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed X-ray tube'
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_orient_matrix_ub_11      -0.0588556107
_diffrn_orient_matrix_ub_12      0.020221028
_diffrn_orient_matrix_ub_13      -0.0407937333
_diffrn_orient_matrix_ub_21      0.0040499475
_diffrn_orient_matrix_ub_22      -0.0605706884
_diffrn_orient_matrix_ub_23      -0.0557263645
_diffrn_orient_matrix_ub_31      -0.0668323142
_diffrn_orient_matrix_ub_32      -0.0596316468
_diffrn_orient_matrix_ub_33      0.0156342299
_diffrn_measurement_device       'Kappa-geometry diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_number            5561
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2904
_reflns_number_gt                1718
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
        WinGX (Farrugia, 1999)
        PLATON (Spek, 1990-2003)
        PARST (Nardelli, 1999)
        enCIFer (Allen et al., 2004)
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0481P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2904
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.47550(19) 0.61178(19) 0.35383(15) 0.0237(4) Uani 1 1 d . . .
H1A H 0.5593 0.6874 0.3174 0.028 Uiso 1 1 calc R . .
H1B H 0.5377 0.5709 0.4165 0.028 Uiso 1 1 calc R . .
C2 C 0.37833(19) 0.70914(19) 0.43171(15) 0.0241(4) Uani 1 1 d . . .
H2A H 0.2933 0.6331 0.4669 0.029 Uiso 1 1 calc R . .
H2B H 0.4572 0.7926 0.5091 0.029 Uiso 1 1 calc R . .
C3 C 0.2083(2) 0.8894(2) 0.44227(16) 0.0300(4) Uani 1 1 d . . .
H3A H 0.1709 0.9616 0.3944 0.036 Uiso 1 1 calc R . .
H3B H 0.2902 0.9607 0.5231 0.036 Uiso 1 1 calc R . .
C4 C 0.0563(2) 0.7796(2) 0.48438(16) 0.0330(4) Uani 1 1 d . . .
H4A H 0.0961 0.7279 0.5507 0.04 Uiso 1 1 calc R . .
H4B H -0.007 0.8483 0.5275 0.04 Uiso 1 1 calc R . .
C5 C -0.0601(2) 0.6455(2) 0.36612(16) 0.0313(4) Uani 1 1 d . . .
H5A H -0.1453 0.566 0.3984 0.038 Uiso 1 1 calc R . .
H5B H -0.1192 0.695 0.3089 0.038 Uiso 1 1 calc R . .
C6 C -0.06691(19) 0.41348(19) 0.18572(15) 0.0268(4) Uani 1 1 d . . .
H6A H -0.1406 0.447 0.1256 0.032 Uiso 1 1 calc R . .
H6B H -0.1403 0.3383 0.2293 0.032 Uiso 1 1 calc R . .
C7 C 0.02550(19) 0.31728(19) 0.10052(15) 0.0250(4) Uani 1 1 d . . .
H7A H -0.0583 0.233 0.0264 0.03 Uiso 1 1 calc R . .
H7B H 0.1028 0.3941 0.0604 0.03 Uiso 1 1 calc R . .
C8 C 0.21061(19) 0.15269(19) 0.07265(15) 0.0241(4) Uani 1 1 d . . .
H8A H 0.1291 0.0867 -0.0099 0.029 Uiso 1 1 calc R . .
H8B H 0.2513 0.076 0.1126 0.029 Uiso 1 1 calc R . .
C9 C 0.36040(18) 0.27350(18) 0.03568(15) 0.0216(4) Uani 1 1 d . . .
H9 H 0.3151 0.3365 -0.019 0.026 Uiso 1 1 calc R . .
C10 C 0.47238(18) 0.39592(19) 0.16199(15) 0.0230(4) Uani 1 1 d . . .
H10A H 0.5289 0.3384 0.2132 0.028 Uiso 1 1 calc R . .
H10B H 0.56 0.482 0.1378 0.028 Uiso 1 1 calc R . .
C11 C 0.4640(2) 0.18766(19) -0.04596(16) 0.0268(4) Uani 1 1 d . . .
H11A H 0.5525 0.272 -0.0711 0.032 Uiso 1 1 calc R . .
H11B H 0.5206 0.1363 0.0114 0.032 Uiso 1 1 calc R . .
C12 C 0.3652(2) 0.05650(19) -0.17182(16) 0.0290(4) Uani 1 1 d . . .
H12A H 0.2792 -0.0307 -0.1473 0.035 Uiso 1 1 calc R . .
H12B H 0.3062 0.1062 -0.229 0.035 Uiso 1 1 calc R . .
C13 C 0.24753(18) 0.34242(19) 0.28247(15) 0.0223(4) Uani 1 1 d . . .
H13A H 0.3045 0.2772 0.3239 0.027 Uiso 1 1 calc R . .
H13B H 0.1908 0.3936 0.3492 0.027 Uiso 1 1 calc R . .
C14 C 0.16280(19) 0.68018(18) 0.24321(14) 0.0234(4) Uani 1 1 d . . .
H14A H 0.1072 0.7437 0.1982 0.028 Uiso 1 1 calc R . .
H14B H 0.2156 0.6216 0.1776 0.028 Uiso 1 1 calc R . .
N1 N 0.37294(15) 0.47195(15) 0.24406(12) 0.0203(3) Uani 1 1 d . . .
N2 N 0.29267(16) 0.79337(15) 0.35499(12) 0.0238(3) Uani 1 1 d . . .
N3 N 0.03739(16) 0.56034(15) 0.28893(12) 0.0234(3) Uani 1 1 d . . .
N4 N 0.12324(15) 0.23421(15) 0.16719(12) 0.0228(3) Uani 1 1 d . . .
O1 O 0.46924(15) -0.01555(13) -0.24539(11) 0.0335(3) Uani 1 1 d . . .
H1 H 0.5329 0.055 -0.2762 0.054(6) Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4612(18) . ?
C1 C2 1.525(2) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 N2 1.4756(18) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 N2 1.4873(18) . ?
C3 C4 1.534(2) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.523(2) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 N3 1.4602(19) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 N3 1.4623(19) . ?
C6 C7 1.526(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 N4 1.4723(19) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 N4 1.4807(18) . ?
C8 C9 1.5412(19) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.524(2) . ?
C9 C11 1.527(2) . ?
C9 H9 1 . ?
C10 N1 1.4571(18) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.518(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 O1 1.4235(18) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 N4 1.4541(19) . ?
C13 N1 1.4710(17) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 N3 1.4607(18) . ?
C14 N2 1.4660(19) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
O1 H1 0.84 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 115.08(13) . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
N2 C2 C1 115.19(12) . . ?
N2 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
N2 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
N2 C3 C4 112.78(13) . . ?
N2 C3 H3A 109 . . ?
C4 C3 H3A 109 . . ?
N2 C3 H3B 109 . . ?
C4 C3 H3B 109 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.96(13) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N3 C5 C4 109.71(13) . . ?
N3 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
N3 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N3 C6 C7 116.54(13) . . ?
N3 C6 H6A 108.2 . . ?
C7 C6 H6A 108.2 . . ?
N3 C6 H6B 108.2 . . ?
C7 C6 H6B 108.2 . . ?
H6A C6 H6B 107.3 . . ?
N4 C7 C6 117.34(13) . . ?
N4 C7 H7A 108 . . ?
C6 C7 H7A 108 . . ?
N4 C7 H7B 108 . . ?
C6 C7 H7B 108 . . ?
H7A C7 H7B 107.2 . . ?
N4 C8 C9 113.74(12) . . ?
N4 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N4 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C11 109.91(13) . . ?
C10 C9 C8 109.70(12) . . ?
C11 C9 C8 113.15(13) . . ?
C10 C9 H9 108 . . ?
C11 C9 H9 108 . . ?
C8 C9 H9 108 . . ?
N1 C10 C9 110.29(12) . . ?
N1 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C9 115.15(13) . . ?
C12 C11 H11A 108.5 . . ?
C9 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C9 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
O1 C12 C11 112.48(13) . . ?
O1 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
O1 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N4 C13 N1 111.00(12) . . ?
N4 C13 H13A 109.4 . . ?
N1 C13 H13A 109.4 . . ?
N4 C13 H13B 109.4 . . ?
N1 C13 H13B 109.4 . . ?
H13A C13 H13B 108 . . ?
N3 C14 N2 111.11(12) . . ?
N3 C14 H14A 109.4 . . ?
N2 C14 H14A 109.4 . . ?
N3 C14 H14B 109.4 . . ?
N2 C14 H14B 109.4 . . ?
H14A C14 H14B 108 . . ?
C10 N1 C1 113.09(12) . . ?
C10 N1 C13 108.60(12) . . ?
C1 N1 C13 115.46(11) . . ?
C14 N2 C2 113.39(12) . . ?
C14 N2 C3 106.67(12) . . ?
C2 N2 C3 110.36(12) . . ?
C5 N3 C14 108.70(12) . . ?
C5 N3 C6 113.26(12) . . ?
C14 N3 C6 115.57(12) . . ?
C13 N4 C7 114.18(12) . . ?
C13 N4 C8 108.12(12) . . ?
C7 N4 C8 110.65(12) . . ?
C12 O1 H1 109.5 . . ?

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
O1 H1 N2 0.84 2.05 2.8865(17) 172.3 2_665

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_common            cyclam-bisformyl-hydroxyethyl
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_A19097O_014_sq
_database_code_depnum_ccdc_archive 'CCDC 2011525'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
South Korea
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H28 Cl2 Cu N4'
_chemical_formula_weight         362.82

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'
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      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                   6.813(2)
_cell_length_b                   12.552(5)
_cell_length_c                   10.796(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.241(12)
_cell_angle_gamma                90
_cell_volume                     898.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4889
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      28.24

_exptl_crystal_description       rod
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             382
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    1.507
_shelx_estimated_absorpt_T_min   0.537
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5275
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9934
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.620
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2133
_reflns_number_gt                1693
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0371P)²+1.6787P] 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         2133
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cu1 Cu 0.500000 0.500000 0.500000 0.0408(2) Uani 1 2 d S . P . .
N2 N 0.3613(5) 0.4268(2) 0.6191(3) 0.0417(6) Uani 1 1 d . . . . .
H2 H 0.234(7) 0.454(4) 0.600(4) 0.063 Uiso 1 1 d . U . . .
C3 C 0.3467(6) 0.3121(3) 0.5864(4) 0.0551(10) Uani 1 1 d . . . . .
H3A H 0.233478 0.279167 0.615978 0.066 Uiso 1 1 calc R U . . .
H3B H 0.472821 0.275056 0.628055 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4436(6) 0.4408(3) 0.7549(4) 0.0536(10) Uani 1 1 d . . . . .
H4A H 0.583429 0.413296 0.777389 0.064 Uiso 1 1 calc R U . . .
H4B H 0.362356 0.399214 0.802970 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4429(7) 0.5580(4) 0.7926(4) 0.0612(11) Uani 1 1 d . . . . .
H5A H 0.304170 0.586021 0.763505 0.073 Uiso 1 1 calc R U . . .
H5B H 0.479788 0.562982 0.886571 0.073 Uiso 1 1 calc R U . . .
C6 C 0.5834(6) 0.6272(3) 0.7397(4) 0.0541(9) Uani 1 1 d . . . . .
H6A H 0.719971 0.595462 0.761980 0.065 Uiso 1 1 calc R U . . .
H6B H 0.591022 0.697963 0.781095 0.065 Uiso 1 1 calc R U . . .
N7 N 0.5237(4) 0.6425(2) 0.5981(3) 0.0408(6) Uani 1 1 d . . . . .
C8 C 0.6885(6) 0.6972(3) 0.5574(4) 0.0523(9) Uani 1 1 d . . . . .
H8A H 0.819248 0.664330 0.598557 0.063 Uiso 1 1 calc R U . . .
H8B H 0.692131 0.773171 0.582452 0.063 Uiso 1 1 calc R U . . .
C9 C 0.3385(6) 0.7061(4) 0.5720(4) 0.0601(10) Uani 1 1 d . . . . .
H9A H 0.359997 0.770925 0.623898 0.090 Uiso 1 1 calc R U . . .
H9B H 0.228803 0.664417 0.592909 0.090 Uiso 1 1 calc R U . . .
H9C H 0.302844 0.725455 0.481671 0.090 Uiso 1 1 calc R U . . .
Cl10 Cl 0.90761(14) 0.44365(8) 0.65547(11) 0.0578(3) 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
Cu1 N2 1.987(3) . ?
Cu1 N2 1.987(3) 3_666 ?
Cu1 N7 2.066(3) . ?
Cu1 N7 2.066(3) 3_666 ?
N2 C4 1.455(5) . ?
N2 C3 1.480(5) . ?
N2 H2 0.91(5) . ?
C3 C8 1.520(6) 3_666 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.526(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.500(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.501(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C9 1.465(5) . ?
N7 C8 1.467(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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 Cu1 N2 180.0 . 3_666 ?
N2 Cu1 N7 93.50(12) . . ?
N2 Cu1 N7 86.50(12) 3_666 . ?
N2 Cu1 N7 86.50(12) . 3_666 ?
N2 Cu1 N7 93.50(12) 3_666 3_666 ?
N7 Cu1 N7 180.00(7) . 3_666 ?
C4 N2 C3 110.3(3) . . ?
C4 N2 Cu1 117.8(2) . . ?
C3 N2 Cu1 108.2(2) . . ?
C4 N2 H2 108(3) . . ?
C3 N2 H2 107(3) . . ?
Cu1 N2 H2 105(3) . . ?
N2 C3 C8 107.7(3) . 3_666 ?
N2 C3 H3A 110.2 . . ?
C8 C3 H3A 110.2 3_666 . ?
N2 C3 H3B 110.2 . . ?
C8 C3 H3B 110.2 3_666 . ?
H3A C3 H3B 108.5 . . ?
N2 C4 C5 111.2(3) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 114.6(3) . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 N7 114.4(3) . . ?
C5 C6 H6A 108.7 . . ?
N7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
N7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C9 N7 C8 111.8(3) . . ?
C9 N7 C6 106.6(3) . . ?
C8 N7 C6 108.5(3) . . ?
C9 N7 Cu1 114.2(2) . . ?
C8 N7 Cu1 103.1(2) . . ?
C6 N7 Cu1 112.5(2) . . ?
N7 C8 C3 108.5(3) . 3_666 ?
N7 C8 H8A 110.0 . . ?
C3 C8 H8A 110.0 3_666 . ?
N7 C8 H8B 110.0 . . ?
C3 C8 H8B 110.0 3_666 . ?
H8A C8 H8B 108.4 . . ?
N7 C9 H9A 109.5 . . ?
N7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
C4 N2 C3 C8 -166.0(3) . . . 3_666 ?
Cu1 N2 C3 C8 -35.9(3) . . . 3_666 ?
C3 N2 C4 C5 -175.0(3) . . . . ?
Cu1 N2 C4 C5 60.2(4) . . . . ?
N2 C4 C5 C6 -67.0(5) . . . . ?
C4 C5 C6 N7 68.4(5) . . . . ?
C5 C6 N7 C9 68.1(4) . . . . ?
C5 C6 N7 C8 -171.3(3) . . . . ?
C5 C6 N7 Cu1 -57.9(4) . . . . ?
C9 N7 C8 C3 -76.9(4) . . . 3_666 ?
C6 N7 C8 C3 165.8(3) . . . 3_666 ?
Cu1 N7 C8 C3 46.3(3) . . . 3_666 ?

_refine_diff_density_max         0.855
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.078























####################################################################### 
# 
# 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_PO19133O_015
_database_code_depnum_ccdc_archive 'CCDC 2011524'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
South Korea
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H28 Cl2 N4 Zn'
_chemical_formula_weight         364.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1456 0.1550 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2992 1.4004 '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                   16.424(3)
_cell_length_b                   6.4810(13)
_cell_length_c                   16.486(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.23(3)
_cell_angle_gamma                90
_cell_volume                     1624.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    26493
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    1.755
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8024
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.314
_diffrn_reflns_theta_max         24.975
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2121
_reflns_number_gt                1303
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'PAL BL2D-SMDC Program'
_computing_cell_refinement       HKL3000sm
_computing_data_reduction        HKL3000sm
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_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)+(0.1777P)²] 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         2121
_refine_ls_number_parameters     171
_refine_ls_number_restraints     288
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0825
_refine_ls_wR_factor_ref         0.2644
_refine_ls_wR_factor_gt          0.2324
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      0.979
_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
Zn1 Zn 0.000000 0.50295(12) 0.250000 0.0682(6) Uani 1 2 d S TU P . .
Cl2A Cl 0.0434(5) 0.7597(8) 0.1681(5) 0.0888(17) Uani 0.5 1 d . U P A 1
N3A N 0.065(2) 0.273(6) 0.190(3) 0.074(5) Uani 0.5 1 d . U P A 1
H3A H 0.050720 0.133409 0.206873 0.089 Uiso 0.5 1 calc R U P A 1
C4A C 0.151(2) 0.285(5) 0.2202(13) 0.078(3) Uani 0.5 1 d D U P A 1
H4AA H 0.167015 0.423672 0.205279 0.093 Uiso 0.5 1 calc R U P A 1
H4AB H 0.172348 0.183462 0.187620 0.093 Uiso 0.5 1 calc R U P A 1
C5A C 0.2032(13) 0.250(2) 0.3177(11) 0.079(3) Uani 0.5 1 d D U P A 1
H5AA H 0.181574 0.122184 0.335648 0.095 Uiso 0.5 1 calc R U P A 1
H5AB H 0.265808 0.228318 0.327208 0.095 Uiso 0.5 1 calc R U P A 1
C6A C 0.1973(10) 0.424(3) 0.3759(10) 0.078(3) Uani 0.5 1 d D U P A 1
H6AA H 0.240441 0.396959 0.435912 0.094 Uiso 0.5 1 calc R U P A 1
H6AB H 0.215573 0.552677 0.355255 0.094 Uiso 0.5 1 calc R U P A 1
N7A N 0.1114(11) 0.460(2) 0.3812(13) 0.074(3) Uani 0.5 1 d D U P A 1
C8A C 0.0844(11) 0.292(3) 0.4239(12) 0.078(3) Uani 0.5 1 d D U P A 1
H8AA H 0.116615 0.303120 0.488064 0.094 Uiso 0.5 1 calc R U P A 1
H8AB H 0.100405 0.159313 0.404455 0.094 Uiso 0.5 1 calc R U P A 1
C9A C -0.0132(13) 0.295(5) 0.404(2) 0.082(4) Uani 0.5 1 d D U P A 1
H9AA H -0.028068 0.180794 0.435640 0.098 Uiso 0.5 1 calc R U P A 1
H9AB H -0.029033 0.426349 0.424744 0.098 Uiso 0.5 1 calc R U P A 1
C10A C 0.1203(11) 0.653(2) 0.4344(10) 0.083(4) Uani 0.5 1 d D U P A 1
H10A H 0.163908 0.630933 0.493772 0.124 Uiso 0.5 1 calc R U P A 1
H10B H 0.063420 0.687450 0.437408 0.124 Uiso 0.5 1 calc R U P A 1
H10C H 0.139520 0.767026 0.406767 0.124 Uiso 0.5 1 calc R U P A 1
Cl2B Cl 0.0834(5) 0.7707(8) 0.2087(5) 0.0909(17) Uani 0.5 1 d . U P A 2
N3B N 0.052(2) 0.263(6) 0.198(3) 0.069(4) Uani 0.5 1 d . U P A 2
H3B H 0.030812 0.128731 0.212696 0.083 Uiso 0.5 1 calc R U P A 2
C4B C 0.158(2) 0.265(5) 0.2425(13) 0.076(3) Uani 0.5 1 d D U P A 2
H4BA H 0.183354 0.137517 0.228049 0.092 Uiso 0.5 1 calc R U P A 2
H4BB H 0.182893 0.386369 0.223705 0.092 Uiso 0.5 1 calc R U P A 2
C5B C 0.1745(12) 0.274(3) 0.3390(12) 0.078(3) Uani 0.5 1 d D U P A 2
H5BA H 0.154340 0.143833 0.356355 0.094 Uiso 0.5 1 calc R U P A 2
H5BB H 0.238607 0.286015 0.372700 0.094 Uiso 0.5 1 calc R U P A 2
N6B N 0.1301(12) 0.448(2) 0.3628(11) 0.075(3) Uani 0.5 1 d D U P A 2
C7B C 0.1217(10) 0.411(3) 0.4475(10) 0.075(3) Uani 0.5 1 d D U P A 2
H7BA H 0.098770 0.539139 0.464043 0.090 Uiso 0.5 1 calc R U P A 2
H7BB H 0.181338 0.387757 0.492190 0.090 Uiso 0.5 1 calc R U P A 2
C8B C 0.0637(11) 0.234(2) 0.4525(13) 0.081(3) Uani 0.5 1 d D U P A 2
H8BA H 0.072143 0.211889 0.514597 0.097 Uiso 0.5 1 calc R U P A 2
H8BB H 0.083182 0.106840 0.431689 0.097 Uiso 0.5 1 calc R U P A 2
C9B C -0.0337(14) 0.265(5) 0.400(2) 0.081(4) Uani 0.5 1 d D U P A 2
H9BA H -0.052963 0.397994 0.415603 0.098 Uiso 0.5 1 calc R U P A 2
H9BB H -0.067714 0.153266 0.413294 0.098 Uiso 0.5 1 calc R U P A 2
C10B C 0.1829(10) 0.637(2) 0.3733(11) 0.087(4) Uani 0.5 1 d D U P A 2
H10D H 0.242411 0.613378 0.416518 0.131 Uiso 0.5 1 calc R U P A 2
H10E H 0.155336 0.749925 0.393376 0.131 Uiso 0.5 1 calc R U P A 2
H10F H 0.185996 0.674614 0.316915 0.131 Uiso 0.5 1 calc R U P 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 N3B 2.11(4) . ?
Zn1 N3B 2.11(4) 2 ?
Zn1 N7A 2.260(19) 2 ?
Zn1 N7A 2.26(2) . ?
Zn1 N3A 2.26(3) . ?
Zn1 N3A 2.26(3) 2 ?
Zn1 N6B 2.268(19) 2 ?
Zn1 N6B 2.268(19) . ?
Zn1 Cl2A 2.415(6) . ?
Zn1 Cl2A 2.415(6) 2 ?
Zn1 Cl2B 2.461(6) . ?
Zn1 Cl2B 2.461(6) 2 ?
N3A C4A 1.32(5) . ?
N3A C9A 1.46(6) 2 ?
N3A H3A 1.0000 . ?
C4A C5A 1.525(19) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A C6A 1.506(18) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A N7A 1.465(18) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
N7A C8A 1.451(18) . ?
N7A C10A 1.504(17) . ?
C8A C9A 1.51(2) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
N3B C9B 1.52(6) 2 ?
N3B C4B 1.61(5) . ?
N3B H3B 1.0000 . ?
C4B C5B 1.51(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B N6B 1.471(18) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
N6B C7B 1.473(18) . ?
N6B C10B 1.476(17) . ?
C7B C8B 1.516(17) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.52(2) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?

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
N7A Zn1 N7A 165.9(8) 2 . ?
N7A Zn1 N3A 81.1(12) 2 . ?
N7A Zn1 N3A 89.6(12) . . ?
N7A Zn1 N3A 89.6(12) 2 2 ?
N7A Zn1 N3A 81.1(12) . 2 ?
N3A Zn1 N3A 97.7(19) . 2 ?
N7A Zn1 N6B 13.0(5) 2 2 ?
N7A Zn1 N6B 159.3(4) . 2 ?
N3A Zn1 N6B 89.5(11) . 2 ?
N3A Zn1 N6B 78.6(12) 2 2 ?
N3B Zn1 N6B 79.3(12) . . ?
N3B Zn1 N6B 87.3(12) 2 . ?
N6B Zn1 N6B 161.9(8) 2 . ?
N7A Zn1 Cl2A 81.5(4) 2 . ?
N7A Zn1 Cl2A 108.5(5) . . ?
N3A Zn1 Cl2A 85.5(10) . . ?
N3A Zn1 Cl2A 170.0(10) 2 . ?
N7A Zn1 Cl2A 108.5(5) 2 2 ?
N7A Zn1 Cl2A 81.5(4) . 2 ?
N3A Zn1 Cl2A 170.0(10) . 2 ?
N3A Zn1 Cl2A 85.5(10) 2 2 ?
Cl2A Zn1 Cl2A 92.9(3) . 2 ?
N3B Zn1 Cl2B 93.1(9) . . ?
N3B Zn1 Cl2B 170.8(11) 2 . ?
N6B Zn1 Cl2B 109.5(4) 2 . ?
N6B Zn1 Cl2B 83.6(4) . . ?
N7A Zn1 Cl2B 91.0(5) 2 2 ?
N7A Zn1 Cl2B 98.9(4) . 2 ?
N3A Zn1 Cl2B 171.0(12) . 2 ?
N3A Zn1 Cl2B 86.6(9) 2 2 ?
Cl2A Zn1 Cl2B 88.97(16) . 2 ?
Cl2A Zn1 Cl2B 17.50(11) 2 2 ?
C4A N3A C9A 120(3) . 2 ?
C4A N3A Zn1 115(2) . . ?
C9A N3A Zn1 103(2) 2 . ?
C4A N3A H3A 106.2 . . ?
C9A N3A H3A 106.2 2 . ?
Zn1 N3A H3A 106.2 . . ?
N3A C4A C5A 119(3) . . ?
N3A C4A H4AA 107.6 . . ?
C5A C4A H4AA 107.6 . . ?
N3A C4A H4AB 107.6 . . ?
C5A C4A H4AB 107.6 . . ?
H4AA C4A H4AB 107.1 . . ?
C6A C5A C4A 114.6(18) . . ?
C6A C5A H5AA 108.6 . . ?
C4A C5A H5AA 108.6 . . ?
C6A C5A H5AB 108.6 . . ?
C4A C5A H5AB 108.6 . . ?
H5AA C5A H5AB 107.6 . . ?
N7A C6A C5A 116.9(15) . . ?
N7A C6A H6AA 108.1 . . ?
C5A C6A H6AA 108.1 . . ?
N7A C6A H6AB 108.1 . . ?
C5A C6A H6AB 108.1 . . ?
H6AA C6A H6AB 107.3 . . ?
C8A N7A C6A 112.8(16) . . ?
C8A N7A C10A 108.7(16) . . ?
C6A N7A C10A 106.5(14) . . ?
C8A N7A Zn1 105.7(12) . . ?
C6A N7A Zn1 114.3(12) . . ?
C10A N7A Zn1 108.7(11) . . ?
N7A C8A C9A 112.3(18) . . ?
N7A C8A H8AA 109.2 . . ?
C9A C8A H8AA 109.2 . . ?
N7A C8A H8AB 109.2 . . ?
C9A C8A H8AB 109.2 . . ?
H8AA C8A H8AB 107.9 . . ?
N3A C9A C8A 112(3) 2 . ?
N3A C9A H9AA 109.2 2 . ?
C8A C9A H9AA 109.2 . . ?
N3A C9A H9AB 109.2 2 . ?
C8A C9A H9AB 109.2 . . ?
H9AA C9A H9AB 107.9 . . ?
N7A C10A H10A 109.5 . . ?
N7A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
N7A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C9B N3B C4B 103(2) 2 . ?
C9B N3B Zn1 118(3) 2 . ?
C4B N3B Zn1 110(2) . . ?
C9B N3B H3B 108.2 2 . ?
C4B N3B H3B 108.2 . . ?
Zn1 N3B H3B 108.2 . . ?
C5B C4B N3B 102(2) . . ?
C5B C4B H4BA 111.4 . . ?
N3B C4B H4BA 111.4 . . ?
C5B C4B H4BB 111.4 . . ?
N3B C4B H4BB 111.4 . . ?
H4BA C4B H4BB 109.2 . . ?
N6B C5B C4B 114(2) . . ?
N6B C5B H5BA 108.8 . . ?
C4B C5B H5BA 108.8 . . ?
N6B C5B H5BB 108.8 . . ?
C4B C5B H5BB 108.8 . . ?
H5BA C5B H5BB 107.7 . . ?
C5B N6B C7B 111.4(16) . . ?
C5B N6B C10B 109.8(16) . . ?
C7B N6B C10B 106.5(14) . . ?
C5B N6B Zn1 108.1(12) . . ?
C7B N6B Zn1 113.9(11) . . ?
C10B N6B Zn1 107.1(11) . . ?
N6B C7B C8B 117.4(15) . . ?
N6B C7B H7BA 108.0 . . ?
C8B C7B H7BA 108.0 . . ?
N6B C7B H7BB 108.0 . . ?
C8B C7B H7BB 108.0 . . ?
H7BA C7B H7BB 107.2 . . ?
C7B C8B C9B 114.6(15) . . ?
C7B C8B H8BA 108.6 . . ?
C9B C8B H8BA 108.6 . . ?
C7B C8B H8BB 108.6 . . ?
C9B C8B H8BB 108.6 . . ?
H8BA C8B H8BB 107.6 . . ?
C8B C9B H9BA 109.5 . . ?
N3B C9B H9BA 109.5 2 . ?
C8B C9B H9BB 109.5 . . ?
N3B C9B H9BB 109.5 2 . ?
H9BA C9B H9BB 108.1 . . ?
N6B C10B H10D 109.5 . . ?
N6B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
N6B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 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
C9A N3A C4A C5A -177(3) 2 . . . ?
Zn1 N3A C4A C5A 60(3) . . . . ?
N3A C4A C5A C6A -73(3) . . . . ?
C4A C5A C6A N7A 67(3) . . . . ?
C5A C6A N7A C8A 67(2) . . . . ?
C5A C6A N7A C10A -173.8(15) . . . . ?
C5A C6A N7A Zn1 -53.8(18) . . . . ?
C6A N7A C8A C9A -161.4(19) . . . . ?
C10A N7A C8A C9A 81(2) . . . . ?
Zn1 N7A C8A C9A -36(2) . . . . ?
N7A C8A C9A N3A 61(3) . . . 2 ?
C9B N3B C4B C5B 177(2) 2 . . . ?
Zn1 N3B C4B C5B 50(2) . . . . ?
N3B C4B C5B N6B -55(2) . . . . ?
C4B C5B N6B C7B 160.0(18) . . . . ?
C4B C5B N6B C10B -82(2) . . . . ?
C4B C5B N6B Zn1 34(2) . . . . ?
C5B N6B C7B C8B -65(2) . . . . ?
C10B N6B C7B C8B 175.2(14) . . . . ?
Zn1 N6B C7B C8B 57.3(17) . . . . ?
N6B C7B C8B C9B -68(3) . . . . ?
C7B C8B C9B N3B 68(3) . . . 2 ?

_refine_diff_density_max         1.760
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.113





















