# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_Acr(CH2NMe2)2_ZnBr(dmf)
_database_code_depnum_ccdc_archive 'CCDC 1061423'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 Br N4 O Zn, C3 H7 Br3 N O Zn'
_chemical_formula_sum            'C25 H37 Br4 N5 O2 Zn2'
_chemical_formula_weight         889.97

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   20.985(3)
_cell_length_b                   9.749(2)
_cell_length_c                   16.858(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.33(2)
_cell_angle_gamma                90
_cell_volume                     3212.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9765
_cell_measurement_theta_min      2.334
_cell_measurement_theta_max      27.8225

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_F_000             1752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    6.499
_shelx_estimated_absorpt_T_min   0.340
_shelx_estimated_absorpt_T_max   0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3815
_exptl_absorpt_correction_T_max  0.5631
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC Mo Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            194567
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.042
_diffrn_reflns_theta_max         27.891
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7674
_reflns_number_gt                7009
_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 v2012.2'
_computing_cell_refinement       'SAINT V8.30C'
_computing_data_reduction        'SAINT V8.30C'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0285P)²+3.3288P] 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         7674
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0528
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34194(2) 0.66238(2) 0.26731(2) 0.02274(5) Uani 1 1 d . . . . .
Zn1 Zn 0.29950(2) 0.82163(2) 0.34473(2) 0.01432(5) Uani 1 1 d . . . . .
N1 N 0.40984(8) 0.88846(17) 0.42322(10) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.54852(10) 0.6489(2) 0.54575(14) 0.0257(4) Uani 1 1 d . . . . .
H1 H 0.5931 0.6208 0.5503 0.031 Uiso 1 1 calc R U . . .
C2 C 0.51903(11) 0.5917(2) 0.59717(14) 0.0285(5) Uani 1 1 d . . . . .
H2 H 0.5429 0.5238 0.6374 0.034 Uiso 1 1 calc R U . . .
C3 C 0.45251(11) 0.6330(2) 0.59110(13) 0.0254(4) Uani 1 1 d . . . . .
H3 H 0.4328 0.5921 0.6279 0.030 Uiso 1 1 calc R U . . .
C4 C 0.41593(10) 0.7299(2) 0.53379(12) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.40325(10) 1.0638(2) 0.32194(13) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.43184(11) 1.1295(2) 0.27098(14) 0.0260(4) Uani 1 1 d . . . . .
H6 H 0.4074 1.2020 0.2351 0.031 Uiso 1 1 calc R U . . .
C7 C 0.49712(12) 1.0918(2) 0.27048(15) 0.0290(5) Uani 1 1 d . . . . .
H7 H 0.5156 1.1388 0.2343 0.035 Uiso 1 1 calc R U . . .
C8 C 0.53321(11) 0.9891(2) 0.32121(15) 0.0264(5) Uani 1 1 d . . . . .
H8 H 0.5769 0.9649 0.3206 0.032 Uiso 1 1 calc R U . . .
C9 C 0.54123(10) 0.8132(2) 0.43091(14) 0.0237(4) Uani 1 1 d . . . . .
H9 H 0.5848 0.7849 0.4317 0.028 Uiso 1 1 calc R U . . .
C10 C 0.51339(10) 0.7508(2) 0.48480(13) 0.0209(4) Uani 1 1 d . . . . .
C11 C 0.44601(9) 0.7916(2) 0.47881(12) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.43949(9) 0.9538(2) 0.37475(12) 0.0179(4) Uani 1 1 d . . . . .
C13 C 0.50597(10) 0.9173(2) 0.37556(13) 0.0217(4) Uani 1 1 d . . . . .
C14 C 0.34839(10) 0.7823(2) 0.53330(12) 0.0197(4) Uani 1 1 d . . . . .
H14A H 0.3403 0.7441 0.5833 0.024 Uiso 1 1 calc R U . . .
H14B H 0.3511 0.8833 0.5397 0.024 Uiso 1 1 calc R U . . .
N2 N 0.28851(8) 0.74726(17) 0.45462(10) 0.0170(3) Uani 1 1 d . . . . .
C15 C 0.22663(10) 0.8047(2) 0.46570(13) 0.0228(4) Uani 1 1 d . . . . .
H15A H 0.2316 0.9043 0.4733 0.034 Uiso 1 1 calc R U . . .
H15B H 0.2213 0.7635 0.5160 0.034 Uiso 1 1 calc R U . . .
H15C H 0.1862 0.7841 0.4152 0.034 Uiso 1 1 calc R U . . .
C16 C 0.28079(11) 0.5955(2) 0.44650(14) 0.0227(4) Uani 1 1 d . . . . .
H16A H 0.2782 0.5574 0.4990 0.034 Uiso 1 1 calc R U . . .
H16B H 0.3203 0.5562 0.4366 0.034 Uiso 1 1 calc R U . . .
H16C H 0.2388 0.5730 0.3985 0.034 Uiso 1 1 calc R U . . .
C17 C 0.33775(10) 1.1138(2) 0.32913(13) 0.0206(4) Uani 1 1 d . . . . .
H17A H 0.3454 1.1284 0.3900 0.025 Uiso 1 1 calc R U . . .
H17B H 0.3258 1.2036 0.3001 0.025 Uiso 1 1 calc R U . . .
N3 N 0.27862(8) 1.01815(17) 0.29191(10) 0.0178(3) Uani 1 1 d . . . . .
C18 C 0.21970(10) 1.0817(2) 0.30704(15) 0.0257(4) Uani 1 1 d . . . . .
H18A H 0.2313 1.0953 0.3683 0.039 Uiso 1 1 calc R U . . .
H18B H 0.1798 1.0213 0.2849 0.039 Uiso 1 1 calc R U . . .
H18C H 0.2091 1.1705 0.2779 0.039 Uiso 1 1 calc R U . . .
C19 C 0.26191(12) 1.0083(2) 0.19838(13) 0.0268(4) Uani 1 1 d . . . . .
H19A H 0.2998 0.9640 0.1874 0.040 Uiso 1 1 calc R U . . .
H19B H 0.2547 1.1005 0.1736 0.040 Uiso 1 1 calc R U . . .
H19C H 0.2202 0.9538 0.1726 0.040 Uiso 1 1 calc R U . . .
O1 O 0.19188(7) 0.77362(16) 0.27357(9) 0.0215(3) Uani 1 1 d . . . . .
C20 C 0.16991(10) 0.7081(2) 0.20569(13) 0.0202(4) Uani 1 1 d . . . . .
H20 H 0.1976 0.6365 0.1975 0.024 Uiso 1 1 calc R U . . .
N4 N 0.11032(8) 0.73200(18) 0.14408(11) 0.0191(3) Uani 1 1 d . . . . .
C21 C 0.08904(11) 0.6534(2) 0.06489(13) 0.0265(4) Uani 1 1 d . . . . .
H21A H 0.0438 0.6134 0.0540 0.040 Uiso 1 1 calc R U . . .
H21B H 0.1221 0.5798 0.0699 0.040 Uiso 1 1 calc R U . . .
H21C H 0.0869 0.7141 0.0177 0.040 Uiso 1 1 calc R U . . .
C22 C 0.06551(10) 0.8432(2) 0.14899(14) 0.0230(4) Uani 1 1 d . . . . .
H22A H 0.0819 0.8806 0.2069 0.034 Uiso 1 1 calc R U . . .
H22B H 0.0189 0.8081 0.1346 0.034 Uiso 1 1 calc R U . . .
H22C H 0.0656 0.9156 0.1087 0.034 Uiso 1 1 calc R U . . .
Zn2 Zn 0.15733(2) 0.26469(2) 0.00710(2) 0.01705(5) Uani 1 1 d . . . . .
Br2 Br 0.12078(2) 0.03168(2) -0.02196(2) 0.02144(5) Uani 1 1 d . . . . .
Br3 Br 0.27627(2) 0.30631(3) 0.05007(2) 0.03254(6) Uani 1 1 d . . . . .
Br4 Br 0.08716(2) 0.41766(2) -0.10030(2) 0.02151(5) Uani 1 1 d . . . . .
O2 O 0.13164(8) 0.30907(15) 0.10968(9) 0.0232(3) Uani 1 1 d . . . . .
N5 N 0.05500(9) 0.28977(18) 0.17532(11) 0.0200(3) Uani 1 1 d . . . . .
C23 C 0.07905(10) 0.2570(2) 0.11579(12) 0.0199(4) Uani 1 1 d . . . . .
H23 H 0.0551 0.1898 0.0750 0.024 Uiso 1 1 calc R U . . .
C24 C 0.08753(12) 0.3933(2) 0.23944(13) 0.0261(4) Uani 1 1 d . . . . .
H24A H 0.0929 0.3578 0.2959 0.039 Uiso 1 1 calc R U . . .
H24B H 0.0590 0.4760 0.2277 0.039 Uiso 1 1 calc R U . . .
H24C H 0.1326 0.4159 0.2380 0.039 Uiso 1 1 calc R U . . .
C25 C -0.00779(11) 0.2266(2) 0.17708(14) 0.0261(4) Uani 1 1 d . . . . .
H25A H 0.0013 0.1847 0.2330 0.039 Uiso 1 1 calc R U . . .
H25B H -0.0234 0.1560 0.1328 0.039 Uiso 1 1 calc R U . . .
H25C H -0.0433 0.2969 0.1666 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.3983(4) . ?
Zn1 N2 2.0789(16) . ?
Zn1 N3 2.0909(17) . ?
Zn1 O1 2.1882(14) . ?
Zn1 N1 2.3039(16) . ?
N1 C11 1.352(3) . ?
N1 C12 1.353(3) . ?
C1 C2 1.355(3) . ?
C1 C10 1.426(3) . ?
C2 C3 1.420(3) . ?
C3 C4 1.370(3) . ?
C4 C11 1.430(3) . ?
C4 C14 1.504(3) . ?
C5 C6 1.372(3) . ?
C5 C12 1.425(3) . ?
C5 C17 1.504(3) . ?
C6 C7 1.422(3) . ?
C7 C8 1.354(4) . ?
C8 C13 1.428(3) . ?
C9 C10 1.387(3) . ?
C9 C13 1.394(3) . ?
C10 C11 1.437(3) . ?
C12 C13 1.435(3) . ?
C14 N2 1.498(2) . ?
N2 C15 1.487(2) . ?
N2 C16 1.489(3) . ?
C17 N3 1.496(2) . ?
N3 C18 1.486(2) . ?
N3 C19 1.489(3) . ?
O1 C20 1.243(2) . ?
C20 N4 1.324(3) . ?
N4 C22 1.457(3) . ?
N4 C21 1.462(3) . ?
Zn2 O2 2.0361(15) . ?
Zn2 Br3 2.3674(5) . ?
Zn2 Br2 2.3907(5) . ?
Zn2 Br4 2.3939(5) . ?
O2 C23 1.253(3) . ?
N5 C23 1.316(3) . ?
N5 C24 1.455(3) . ?
N5 C25 1.464(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N3 128.68(6) . . ?
N2 Zn1 O1 89.25(6) . . ?
N3 Zn1 O1 87.01(6) . . ?
N2 Zn1 N1 90.05(6) . . ?
N3 Zn1 N1 89.81(6) . . ?
O1 Zn1 N1 175.31(6) . . ?
N2 Zn1 Br1 116.27(5) . . ?
N3 Zn1 Br1 115.04(5) . . ?
O1 Zn1 Br1 94.40(4) . . ?
N1 Zn1 Br1 90.06(4) . . ?
C11 N1 C12 118.79(16) . . ?
C11 N1 Zn1 113.22(13) . . ?
C12 N1 Zn1 111.91(12) . . ?
C2 C1 C10 120.71(19) . . ?
C1 C2 C3 120.2(2) . . ?
C4 C3 C2 122.0(2) . . ?
C3 C4 C11 118.75(19) . . ?
C3 C4 C14 121.56(19) . . ?
C11 C4 C14 119.41(17) . . ?
C6 C5 C12 119.15(18) . . ?
C6 C5 C17 121.31(19) . . ?
C12 C5 C17 119.30(17) . . ?
C5 C6 C7 121.7(2) . . ?
C8 C7 C6 120.4(2) . . ?
C7 C8 C13 120.36(19) . . ?
C10 C9 C13 120.68(18) . . ?
C9 C10 C1 123.16(19) . . ?
C9 C10 C11 118.07(19) . . ?
C1 C10 C11 118.8(2) . . ?
N1 C11 C4 118.30(17) . . ?
N1 C11 C10 122.16(18) . . ?
C4 C11 C10 119.54(18) . . ?
N1 C12 C5 118.28(17) . . ?
N1 C12 C13 122.46(18) . . ?
C5 C12 C13 119.26(18) . . ?
C9 C13 C8 123.21(19) . . ?
C9 C13 C12 117.65(19) . . ?
C8 C13 C12 119.1(2) . . ?
N2 C14 C4 114.39(15) . . ?
C15 N2 C16 108.34(16) . . ?
C15 N2 C14 107.02(15) . . ?
C16 N2 C14 109.64(15) . . ?
C15 N2 Zn1 111.46(12) . . ?
C16 N2 Zn1 107.96(12) . . ?
C14 N2 Zn1 112.36(12) . . ?
N3 C17 C5 114.02(16) . . ?
C18 N3 C19 108.59(16) . . ?
C18 N3 C17 106.44(16) . . ?
C19 N3 C17 108.94(16) . . ?
C18 N3 Zn1 111.58(13) . . ?
C19 N3 Zn1 108.90(13) . . ?
C17 N3 Zn1 112.30(12) . . ?
C20 O1 Zn1 125.28(13) . . ?
O1 C20 N4 124.07(19) . . ?
C20 N4 C22 122.10(17) . . ?
C20 N4 C21 120.81(18) . . ?
C22 N4 C21 116.94(17) . . ?
O2 Zn2 Br3 106.21(5) . . ?
O2 Zn2 Br2 102.22(4) . . ?
Br3 Zn2 Br2 116.712(12) . . ?
O2 Zn2 Br4 103.30(4) . . ?
Br3 Zn2 Br4 114.496(19) . . ?
Br2 Zn2 Br4 111.944(19) . . ?
C23 O2 Zn2 119.81(13) . . ?
C23 N5 C24 121.90(18) . . ?
C23 N5 C25 120.72(18) . . ?
C24 N5 C25 117.34(17) . . ?
O2 C23 N5 123.92(19) . . ?

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
C10 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C11 -0.3(3) . . . . ?
C2 C3 C4 C14 -174.27(19) . . . . ?
C12 C5 C6 C7 -0.9(3) . . . . ?
C17 C5 C6 C7 173.42(19) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C13 0.3(3) . . . . ?
C13 C9 C10 C1 -176.70(19) . . . . ?
C13 C9 C10 C11 3.0(3) . . . . ?
C2 C1 C10 C9 179.6(2) . . . . ?
C2 C1 C10 C11 -0.1(3) . . . . ?
C12 N1 C11 C4 175.82(17) . . . . ?
Zn1 N1 C11 C4 -49.8(2) . . . . ?
C12 N1 C11 C10 -3.4(3) . . . . ?
Zn1 N1 C11 C10 130.95(16) . . . . ?
C3 C4 C11 N1 -179.17(18) . . . . ?
C14 C4 C11 N1 -5.1(3) . . . . ?
C3 C4 C11 C10 0.1(3) . . . . ?
C14 C4 C11 C10 174.17(17) . . . . ?
C9 C10 C11 N1 -0.4(3) . . . . ?
C1 C10 C11 N1 179.33(17) . . . . ?
C9 C10 C11 C4 -179.62(18) . . . . ?
C1 C10 C11 C4 0.1(3) . . . . ?
C11 N1 C12 C5 -174.54(17) . . . . ?
Zn1 N1 C12 C5 50.6(2) . . . . ?
C11 N1 C12 C13 4.7(3) . . . . ?
Zn1 N1 C12 C13 -130.22(16) . . . . ?
C6 C5 C12 N1 -178.66(18) . . . . ?
C17 C5 C12 N1 6.9(3) . . . . ?
C6 C5 C12 C13 2.1(3) . . . . ?
C17 C5 C12 C13 -172.37(17) . . . . ?
C10 C9 C13 C8 177.33(19) . . . . ?
C10 C9 C13 C12 -1.9(3) . . . . ?
C7 C8 C13 C9 -178.2(2) . . . . ?
C7 C8 C13 C12 0.9(3) . . . . ?
N1 C12 C13 C9 -2.1(3) . . . . ?
C5 C12 C13 C9 177.12(18) . . . . ?
N1 C12 C13 C8 178.68(18) . . . . ?
C5 C12 C13 C8 -2.1(3) . . . . ?
C3 C4 C14 N2 -114.8(2) . . . . ?
C11 C4 C14 N2 71.3(2) . . . . ?
C4 C14 N2 C15 179.14(17) . . . . ?
C4 C14 N2 C16 61.8(2) . . . . ?
C4 C14 N2 Zn1 -58.2(2) . . . . ?
C6 C5 C17 N3 112.7(2) . . . . ?
C12 C5 C17 N3 -72.9(2) . . . . ?
C5 C17 N3 C18 178.32(17) . . . . ?
C5 C17 N3 C19 -64.8(2) . . . . ?
C5 C17 N3 Zn1 55.95(19) . . . . ?
Zn1 O1 C20 N4 -146.10(16) . . . . ?
O1 C20 N4 C22 2.6(3) . . . . ?
O1 C20 N4 C21 178.01(19) . . . . ?
Zn2 O2 C23 N5 -173.27(15) . . . . ?
C24 N5 C23 O2 1.2(3) . . . . ?
C25 N5 C23 O2 178.55(19) . . . . ?

_refine_diff_density_max         1.419
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.078


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF/DMF'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Acr(CH2NMe2)2_CdBr2
_database_code_depnum_ccdc_archive 'CCDC 1061424'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4,5-bis(dimethylaminemethylene)acridine cadmium bromide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 Br2 Cd N3'
_chemical_formula_sum            'C19 H23 Br2 Cd N3'
_chemical_formula_weight         565.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br 0.1811 1.6452 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -1.4396 0.7832 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.135(2)
_cell_length_b                   13.332(2)
_cell_length_c                   13.562(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2013.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9755
_cell_measurement_theta_min      2.2235
_cell_measurement_theta_max      21.399

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.185
_exptl_absorpt_coefficient_mu    2.706
_shelx_estimated_absorpt_T_min   0.581
_shelx_estimated_absorpt_T_max   0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            77405
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_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         1.690
_diffrn_reflns_theta_max         21.684
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4810
_reflns_number_gt                4699
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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 v2012.2'
_computing_cell_refinement       'SAINT V8.30C'
_computing_data_reduction        'SAINT V8.30C'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0099P)²+0.4021P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00180(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2011 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4810
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0129
_refine_ls_R_factor_gt           0.0121
_refine_ls_wR_factor_ref         0.0263
_refine_ls_wR_factor_gt          0.0261
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.43800(2) 0.70350(2) 0.74869(2) 0.01138(4) Uani 1 1 d . . . . .
Br1 Br 0.54328(2) 0.83812(2) 0.64134(2) 0.01494(5) Uani 1 1 d . . . . .
N1 N 0.60138(16) 0.58864(14) 0.68272(14) 0.0125(4) Uani 1 1 d . . . . .
C1 C 0.6551(3) 0.58872(19) 0.4123(2) 0.0282(7) Uani 1 1 d . . . . .
H1 H 0.7163 0.6036 0.3658 0.034 Uiso 1 1 calc R U . . .
Br2 Br 0.26165(2) 0.80896(2) 0.83116(2) 0.01949(6) Uani 1 1 d . . . . .
C2 C 0.5462(3) 0.55776(19) 0.38029(19) 0.0321(7) Uani 1 1 d . . . . .
H2 H 0.5303 0.5535 0.3116 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4553(3) 0.53139(18) 0.44985(18) 0.0258(6) Uani 1 1 d . . . . .
H3 H 0.3803 0.5072 0.4264 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4731(2) 0.54009(17) 0.54928(17) 0.0176(5) Uani 1 1 d . . . . .
C5 C 0.7255(2) 0.63238(17) 0.82052(19) 0.0180(5) Uani 1 1 d . . . . .
C6 C 0.8316(2) 0.67017(19) 0.8545(2) 0.0268(6) Uani 1 1 d . . . . .
H6 H 0.8428 0.6769 0.9236 0.032 Uiso 1 1 calc R U . . .
C7 C 0.9254(2) 0.6997(2) 0.7904(2) 0.0356(7) Uani 1 1 d . . . . .
H7 H 0.9968 0.7283 0.8166 0.043 Uiso 1 1 calc R U . . .
C9 C 0.7883(2) 0.63386(18) 0.5511(2) 0.0253(6) Uani 1 1 d . . . . .
H9 H 0.8518 0.6490 0.5067 0.030 Uiso 1 1 calc R U . . .
C8 C 0.9135(2) 0.6873(2) 0.6922(2) 0.0311(7) Uani 1 1 d . . . . .
H8 H 0.9775 0.7059 0.6496 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6790(2) 0.59934(18) 0.51446(19) 0.0213(6) Uani 1 1 d . . . . .
C11 C 0.5865(2) 0.57617(17) 0.58438(18) 0.0156(5) Uani 1 1 d . . . . .
C12 C 0.7088(2) 0.62125(17) 0.71614(19) 0.0161(5) Uani 1 1 d . . . . .
C13 C 0.8055(2) 0.64641(18) 0.6515(2) 0.0221(6) Uani 1 1 d . . . . .
C14 C 0.3795(2) 0.50670(17) 0.62171(18) 0.0161(5) Uani 1 1 d . . . . .
H14A H 0.3214 0.4628 0.5872 0.019 Uiso 1 1 calc R U . . .
H14B H 0.4189 0.4661 0.6736 0.019 Uiso 1 1 calc R U . . .
N2 N 0.31227(16) 0.59000(14) 0.66972(15) 0.0146(4) Uani 1 1 d . . . . .
C15 C 0.2298(2) 0.54568(18) 0.7425(2) 0.0230(5) Uani 1 1 d . . . . .
H15A H 0.1867 0.5993 0.7771 0.034 Uiso 1 1 calc R U . . .
H15B H 0.2757 0.5060 0.7902 0.034 Uiso 1 1 calc R U . . .
H15C H 0.1719 0.5022 0.7087 0.034 Uiso 1 1 calc R U . . .
C16 C 0.2410(2) 0.64578(19) 0.59519(18) 0.0219(5) Uani 1 1 d . . . . .
H16A H 0.2951 0.6741 0.5454 0.033 Uiso 1 1 calc R U . . .
H16B H 0.1968 0.7001 0.6276 0.033 Uiso 1 1 calc R U . . .
H16C H 0.1842 0.6000 0.5633 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6304(2) 0.59577(18) 0.89016(18) 0.0177(5) Uani 1 1 d . . . . .
H17A H 0.6016 0.5294 0.8674 0.021 Uiso 1 1 calc R U . . .
H17B H 0.6666 0.5866 0.9562 0.021 Uiso 1 1 calc R U . . .
N3 N 0.52530(17) 0.66472(14) 0.89900(13) 0.0147(4) Uani 1 1 d . . . . .
C18 C 0.4372(2) 0.61705(18) 0.96631(17) 0.0219(5) Uani 1 1 d . . . . .
H18A H 0.3651 0.6589 0.9704 0.033 Uiso 1 1 calc R U . . .
H18B H 0.4728 0.6101 1.0321 0.033 Uiso 1 1 calc R U . . .
H18C H 0.4157 0.5506 0.9409 0.033 Uiso 1 1 calc R U . . .
C19 C 0.5639(2) 0.76175(17) 0.94088(17) 0.0207(5) Uani 1 1 d . . . . .
H19A H 0.6234 0.7927 0.8972 0.031 Uiso 1 1 calc R U . . .
H19B H 0.5995 0.7507 1.0060 0.031 Uiso 1 1 calc R U . . .
H19C H 0.4942 0.8062 0.9472 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N3 2.3170(19) . ?
Cd1 N2 2.3231(19) . ?
Cd1 N1 2.5407(18) . ?
Cd1 Br1 2.5913(4) . ?
Cd1 Br2 2.6616(4) . ?
N1 C12 1.351(3) . ?
N1 C11 1.354(3) . ?
C1 C2 1.352(4) . ?
C1 C10 1.417(4) . ?
C2 C3 1.428(4) . ?
C3 C4 1.368(3) . ?
C4 C11 1.432(3) . ?
C4 C14 1.500(3) . ?
C5 C6 1.364(3) . ?
C5 C12 1.435(4) . ?
C5 C17 1.501(3) . ?
C6 C7 1.415(4) . ?
C7 C8 1.350(4) . ?
C9 C13 1.385(4) . ?
C9 C10 1.392(4) . ?
C8 C13 1.431(4) . ?
C10 C11 1.434(3) . ?
C12 C13 1.429(3) . ?
C14 N2 1.489(3) . ?
N2 C15 1.472(3) . ?
N2 C16 1.484(3) . ?
C17 N3 1.493(3) . ?
N3 C19 1.477(3) . ?
N3 C18 1.483(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cd1 N2 120.87(7) . . ?
N3 Cd1 N1 82.81(6) . . ?
N2 Cd1 N1 82.91(6) . . ?
N3 Cd1 Br1 117.33(5) . . ?
N2 Cd1 Br1 117.69(5) . . ?
N1 Cd1 Br1 84.01(4) . . ?
N3 Cd1 Br2 93.31(5) . . ?
N2 Cd1 Br2 95.35(5) . . ?
N1 Cd1 Br2 174.08(4) . . ?
Br1 Cd1 Br2 101.773(14) . . ?
C12 N1 C11 118.6(2) . . ?
C12 N1 Cd1 108.77(14) . . ?
C11 N1 Cd1 109.46(14) . . ?
C2 C1 C10 120.9(3) . . ?
C1 C2 C3 119.9(2) . . ?
C4 C3 C2 121.8(3) . . ?
C3 C4 C11 119.0(2) . . ?
C3 C4 C14 121.3(2) . . ?
C11 C4 C14 119.6(2) . . ?
C6 C5 C12 118.9(2) . . ?
C6 C5 C17 121.2(2) . . ?
C12 C5 C17 119.7(2) . . ?
C5 C6 C7 122.3(3) . . ?
C8 C7 C6 120.0(3) . . ?
C13 C9 C10 120.7(2) . . ?
C7 C8 C13 120.7(3) . . ?
C9 C10 C1 123.1(3) . . ?
C9 C10 C11 117.6(2) . . ?
C1 C10 C11 119.3(3) . . ?
N1 C11 C4 118.4(2) . . ?
N1 C11 C10 122.5(2) . . ?
C4 C11 C10 119.1(2) . . ?
N1 C12 C13 122.5(2) . . ?
N1 C12 C5 118.6(2) . . ?
C13 C12 C5 118.9(2) . . ?
C9 C13 C12 118.1(2) . . ?
C9 C13 C8 122.8(2) . . ?
C12 C13 C8 119.1(3) . . ?
N2 C14 C4 114.48(19) . . ?
C15 N2 C16 108.91(18) . . ?
C15 N2 C14 107.91(18) . . ?
C16 N2 C14 110.15(19) . . ?
C15 N2 Cd1 109.17(15) . . ?
C16 N2 Cd1 108.03(14) . . ?
C14 N2 Cd1 112.61(13) . . ?
N3 C17 C5 113.80(19) . . ?
C19 N3 C18 109.33(19) . . ?
C19 N3 C17 110.03(19) . . ?
C18 N3 C17 107.69(18) . . ?
C19 N3 Cd1 105.36(13) . . ?
C18 N3 Cd1 111.09(14) . . ?
C17 N3 Cd1 113.30(14) . . ?

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
C10 C1 C2 C3 -2.5(4) . . . . ?
C1 C2 C3 C4 2.5(4) . . . . ?
C2 C3 C4 C11 -0.3(4) . . . . ?
C2 C3 C4 C14 -176.5(2) . . . . ?
C12 C5 C6 C7 0.6(4) . . . . ?
C17 C5 C6 C7 176.2(2) . . . . ?
C5 C6 C7 C8 -2.6(4) . . . . ?
C6 C7 C8 C13 1.4(4) . . . . ?
C13 C9 C10 C1 177.6(2) . . . . ?
C13 C9 C10 C11 -0.9(3) . . . . ?
C2 C1 C10 C9 -178.0(2) . . . . ?
C2 C1 C10 C11 0.4(4) . . . . ?
C12 N1 C11 C4 179.0(2) . . . . ?
Cd1 N1 C11 C4 -55.4(2) . . . . ?
C12 N1 C11 C10 -2.1(3) . . . . ?
Cd1 N1 C11 C10 123.5(2) . . . . ?
C3 C4 C11 N1 177.2(2) . . . . ?
C14 C4 C11 N1 -6.6(3) . . . . ?
C3 C4 C11 C10 -1.8(3) . . . . ?
C14 C4 C11 C10 174.4(2) . . . . ?
C9 C10 C11 N1 1.3(3) . . . . ?
C1 C10 C11 N1 -177.1(2) . . . . ?
C9 C10 C11 C4 -179.7(2) . . . . ?
C1 C10 C11 C4 1.8(3) . . . . ?
C11 N1 C12 C13 2.3(3) . . . . ?
Cd1 N1 C12 C13 -123.6(2) . . . . ?
C11 N1 C12 C5 -178.6(2) . . . . ?
Cd1 N1 C12 C5 55.5(2) . . . . ?
C6 C5 C12 N1 -176.7(2) . . . . ?
C17 C5 C12 N1 7.7(3) . . . . ?
C6 C5 C12 C13 2.4(3) . . . . ?
C17 C5 C12 C13 -173.3(2) . . . . ?
C10 C9 C13 C12 1.1(4) . . . . ?
C10 C9 C13 C8 -176.2(2) . . . . ?
N1 C12 C13 C9 -1.8(3) . . . . ?
C5 C12 C13 C9 179.1(2) . . . . ?
N1 C12 C13 C8 175.5(2) . . . . ?
C5 C12 C13 C8 -3.5(3) . . . . ?
C7 C8 C13 C9 178.9(3) . . . . ?
C7 C8 C13 C12 1.6(4) . . . . ?
C3 C4 C14 N2 -105.3(3) . . . . ?
C11 C4 C14 N2 78.5(3) . . . . ?
C4 C14 N2 C15 -176.6(2) . . . . ?
C4 C14 N2 C16 64.6(3) . . . . ?
C4 C14 N2 Cd1 -56.0(2) . . . . ?
C6 C5 C17 N3 105.9(3) . . . . ?
C12 C5 C17 N3 -78.5(3) . . . . ?
C5 C17 N3 C19 -63.3(3) . . . . ?
C5 C17 N3 C18 177.62(19) . . . . ?
C5 C17 N3 Cd1 54.4(2) . . . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method THF/DMF
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_AcrNMe2_ZnOAc
_database_code_depnum_ccdc_archive 'CCDC 1423218'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4,5-bis(dimethylaminemethylene)acridine tetrakis(?-acetate) bis(acetate) zinc(II) '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H41 N3 O12 Zn3'
_chemical_formula_sum            'C31 H41 N3 O12 Zn3'
_chemical_formula_weight         843.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.3242 0.9375 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.449(2)
_cell_length_b                   20.113(2)
_cell_length_c                   21.008(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.42(2)
_cell_angle_gamma                90
_cell_volume                     3499.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9813
_cell_measurement_theta_min      2.237
_cell_measurement_theta_max      20.537

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             1736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    1.111
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5243
_exptl_absorpt_correction_T_max  0.5599
_exptl_absorpt_process_details   SADABS-2015/1
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'INCOATEC Ag Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            178761
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.940
_diffrn_reflns_theta_max         20.553
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7163
_reflns_number_gt                6521
_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 v2012.2'
_computing_cell_refinement       'SAINT V8.30C'
_computing_data_reduction        'SAINT V8.30C'
_computing_structure_solution    
'SHELXT (G.M.Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0227P)²+3.1079P] 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         7163
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0544
_refine_ls_wR_factor_gt          0.0526
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.23835(2) 0.22958(2) 0.48204(2) 0.01473(5) Uani 1 1 d . . . . .
N1 N 0.15944(16) 0.16971(7) 0.38632(7) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.4785(2) 0.09064(11) 0.31285(9) 0.0284(4) Uani 1 1 d . . . . .
H1 H 0.5132 0.0482 0.3013 0.034 Uiso 1 1 calc R U . . .
C2 C 0.5645(2) 0.14555(12) 0.30402(9) 0.0323(5) Uani 1 1 d . . . . .
H2 H 0.6600 0.1411 0.2869 0.039 Uiso 1 1 calc R U . . .
C3 C 0.5137(2) 0.20949(11) 0.31997(9) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.5748 0.2474 0.3126 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3779(2) 0.21794(9) 0.34592(8) 0.0219(4) Uani 1 1 d . . . . .
C5 C -0.0672(2) 0.12671(9) 0.42521(8) 0.0188(3) Uani 1 1 d . . . . .
C6 C -0.1568(2) 0.07277(9) 0.43632(9) 0.0240(4) Uani 1 1 d . . . . .
H6 H -0.2484 0.0795 0.4555 0.029 Uiso 1 1 calc R U . . .
C7 C -0.1171(2) 0.00700(9) 0.42006(9) 0.0268(4) Uani 1 1 d . . . . .
H7 H -0.1796 -0.0295 0.4299 0.032 Uiso 1 1 calc R U . . .
C8 C 0.0097(2) -0.00387(9) 0.39063(9) 0.0242(4) Uani 1 1 d . . . . .
H8 H 0.0337 -0.0478 0.3788 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2410(2) 0.04196(9) 0.34863(8) 0.0218(4) Uani 1 1 d . . . . .
H9 H 0.2674 -0.0011 0.3352 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3359(2) 0.09609(9) 0.33947(8) 0.0213(4) Uani 1 1 d . . . . .
C11 C 0.2882(2) 0.16043(9) 0.35782(8) 0.0182(3) Uani 1 1 d . . . . .
C12 C 0.0702(2) 0.11639(8) 0.39580(8) 0.0165(3) Uani 1 1 d . . . . .
C13 C 0.1075(2) 0.05040(9) 0.37733(8) 0.0191(3) Uani 1 1 d . . . . .
C14 C 0.3116(2) 0.28519(9) 0.35718(8) 0.0232(4) Uani 1 1 d . . . . .
H14A H 0.3693 0.3190 0.3362 0.028 Uiso 1 1 calc R U . . .
H14B H 0.1964 0.2866 0.3355 0.028 Uiso 1 1 calc R U . . .
N2 N 0.32462(18) 0.30371(7) 0.42700(7) 0.0205(3) Uani 1 1 d . . . . .
C15 C 0.2279(3) 0.36525(9) 0.42832(10) 0.0300(4) Uani 1 1 d . . . . .
H15A H 0.2330 0.3789 0.4734 0.045 Uiso 1 1 calc R U . . .
H15B H 0.1154 0.3567 0.4075 0.045 Uiso 1 1 calc R U . . .
H15C H 0.2717 0.4007 0.4049 0.045 Uiso 1 1 calc R U . . .
C16 C 0.4964(2) 0.31967(10) 0.45468(9) 0.0290(4) Uani 1 1 d . . . . .
H16A H 0.5629 0.2800 0.4534 0.044 Uiso 1 1 calc R U . . .
H16B H 0.5063 0.3344 0.4998 0.044 Uiso 1 1 calc R U . . .
H16C H 0.5331 0.3552 0.4291 0.044 Uiso 1 1 calc R U . . .
C17 C -0.1146(2) 0.19638(9) 0.44011(9) 0.0199(3) Uani 1 1 d . . . . .
H17A H -0.1185 0.2244 0.4011 0.024 Uiso 1 1 calc R U . . .
H17B H -0.2244 0.1954 0.4499 0.024 Uiso 1 1 calc R U . . .
N3 N -0.00101(17) 0.22762(7) 0.49628(7) 0.0187(3) Uani 1 1 d . . . . .
C18 C -0.0633(2) 0.29518(10) 0.50614(10) 0.0298(4) Uani 1 1 d . . . . .
H18A H 0.0126 0.3180 0.5405 0.045 Uiso 1 1 calc R U . . .
H18B H -0.1686 0.2915 0.5187 0.045 Uiso 1 1 calc R U . . .
H18C H -0.0750 0.3206 0.4657 0.045 Uiso 1 1 calc R U . . .
C19 C -0.0034(2) 0.18860(10) 0.55646(9) 0.0256(4) Uani 1 1 d . . . . .
H19A H 0.0635 0.2110 0.5937 0.038 Uiso 1 1 calc R U . . .
H19B H 0.0393 0.1439 0.5519 0.038 Uiso 1 1 calc R U . . .
H19C H -0.1146 0.1853 0.5632 0.038 Uiso 1 1 calc R U . . .
O1 O 0.31292(14) 0.14269(6) 0.52110(6) 0.0196(2) Uani 1 1 d . . . . .
C20 C 0.4635(2) 0.13335(9) 0.52341(8) 0.0210(4) Uani 1 1 d . . . . .
C21 C 0.5372(2) 0.07303(10) 0.56105(10) 0.0316(4) Uani 1 1 d . . . . .
H21A H 0.5560 0.0826 0.6077 0.047 Uiso 1 1 calc R U . . .
H21B H 0.6401 0.0622 0.5486 0.047 Uiso 1 1 calc R U . . .
H21C H 0.4634 0.0352 0.5512 0.047 Uiso 1 1 calc R U . . .
O2 O 0.54832(17) 0.17166(8) 0.49895(8) 0.0405(4) Uani 1 1 d . . . . .
O3 O 0.31163(15) 0.29048(6) 0.56532(6) 0.0205(3) Uani 1 1 d . . . . .
C22 C 0.4192(2) 0.28724(9) 0.61569(9) 0.0219(4) Uani 1 1 d . . . . .
C23 C 0.4579(3) 0.22225(10) 0.65124(10) 0.0444(6) Uani 1 1 d . . . . .
H23A H 0.4587 0.2288 0.6975 0.067 Uiso 1 1 calc R U . . .
H23B H 0.5642 0.2066 0.6458 0.067 Uiso 1 1 calc R U . . .
H23C H 0.3759 0.1891 0.6335 0.067 Uiso 1 1 calc R U . . .
O4 O 0.50029(15) 0.33762(6) 0.64063(6) 0.0251(3) Uani 1 1 d . . . . .
Zn2 Zn 0.40221(2) 0.42513(2) 0.63409(2) 0.01805(5) Uani 1 1 d . . . . .
O5 O 0.34388(17) 0.46996(6) 0.55038(6) 0.0282(3) Uani 1 1 d . . . . .
C24 C 0.2606(2) 0.52186(9) 0.53549(8) 0.0213(4) Uani 1 1 d . . . . .
C25 C 0.2182(3) 0.53892(10) 0.46414(9) 0.0324(5) Uani 1 1 d . . . . .
H25A H 0.1958 0.5866 0.4591 0.049 Uiso 1 1 calc R U . . .
H25B H 0.1223 0.5137 0.4436 0.049 Uiso 1 1 calc R U . . .
H25C H 0.3089 0.5274 0.4435 0.049 Uiso 1 1 calc R U . . .
O6 O 0.21016(16) 0.55943(6) 0.57457(6) 0.0258(3) Uani 1 1 d . . . . .
O7 O 0.09112(16) 0.49749(6) 0.68984(7) 0.0266(3) Uani 1 1 d . . . . .
C26 C 0.0950(2) 0.43561(8) 0.68333(8) 0.0191(3) Uani 1 1 d . . . . .
C27 C -0.0434(2) 0.39605(9) 0.69926(9) 0.0242(4) Uani 1 1 d . . . . .
H27A H -0.1413 0.4234 0.6914 0.036 Uiso 1 1 calc R U . . .
H27B H -0.0179 0.3827 0.7450 0.036 Uiso 1 1 calc R U . . .
H27C H -0.0609 0.3563 0.6717 0.036 Uiso 1 1 calc R U . . .
O8 O 0.20622(16) 0.40361(7) 0.66547(7) 0.0294(3) Uani 1 1 d . . . . .
O9 O 0.58085(15) 0.47707(6) 0.68368(6) 0.0244(3) Uani 1 1 d . . . . .
C28 C 0.5870(2) 0.53432(8) 0.70810(8) 0.0186(3) Uani 1 1 d . . . . .
C29 C 0.7493(2) 0.55792(9) 0.74454(9) 0.0254(4) Uani 1 1 d . . . . .
H29A H 0.7836 0.5304 0.7833 0.038 Uiso 1 1 calc R U . . .
H29B H 0.7410 0.6044 0.7575 0.038 Uiso 1 1 calc R U . . .
H29C H 0.8287 0.5543 0.7165 0.038 Uiso 1 1 calc R U . . .
O10 O 0.46878(16) 0.57269(7) 0.70556(7) 0.0301(3) Uani 1 1 d . . . . .
Zn3 Zn 0.23525(2) 0.56743(2) 0.67090(2) 0.01616(5) Uani 1 1 d . . . . .
O11 O 0.15015(16) 0.65702(6) 0.67996(6) 0.0255(3) Uani 1 1 d . . . . .
C30 C 0.1523(2) 0.66228(9) 0.74104(9) 0.0245(4) Uani 1 1 d . . . . .
C31 C 0.0991(3) 0.72873(11) 0.76338(11) 0.0390(5) Uani 1 1 d . . . . .
H31A H 0.0103 0.7219 0.7865 0.059 Uiso 1 1 calc R U . . .
H31B H 0.0624 0.7574 0.7256 0.059 Uiso 1 1 calc R U . . .
H31C H 0.1900 0.7499 0.7925 0.059 Uiso 1 1 calc R U . . .
O12 O 0.19737(18) 0.61709(7) 0.78013(7) 0.0339(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
Zn1 O1 1.9798(12) . ?
Zn1 N3 2.1025(15) . ?
Zn1 N2 2.1035(15) . ?
Zn1 O3 2.1250(12) . ?
Zn1 N1 2.3253(14) . ?
N1 C12 1.348(2) . ?
N1 C11 1.355(2) . ?
C1 C2 1.355(3) . ?
C1 C10 1.430(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C11 1.432(2) . ?
C4 C14 1.501(3) . ?
C5 C6 1.369(2) . ?
C5 C12 1.434(2) . ?
C5 C17 1.507(2) . ?
C6 C7 1.423(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.356(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.430(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 C13 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.431(2) . ?
C12 C13 1.435(2) . ?
C14 N2 1.496(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N2 C15 1.486(2) . ?
N2 C16 1.488(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N3 1.503(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N3 C18 1.486(2) . ?
N3 C19 1.492(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O1 C20 1.277(2) . ?
C20 O2 1.232(2) . ?
C20 C21 1.513(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O3 C22 1.253(2) . ?
C22 O4 1.276(2) . ?
C22 C23 1.509(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O4 Zn2 1.9386(13) . ?
Zn2 O8 1.9485(14) . ?
Zn2 O5 1.9506(13) . ?
Zn2 O9 1.9576(13) . ?
O5 C24 1.263(2) . ?
C24 O6 1.251(2) . ?
C24 C25 1.510(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O6 Zn3 1.9992(13) . ?
O7 C26 1.253(2) . ?
O7 Zn3 1.9524(13) . ?
C26 O8 1.256(2) . ?
C26 C27 1.505(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O9 C28 1.257(2) . ?
C28 O10 1.255(2) . ?
C28 C29 1.509(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
O10 Zn3 1.9661(14) . ?
Zn3 O11 1.9632(12) . ?
Zn3 C30 2.5906(18) . ?
O11 C30 1.284(2) . ?
C30 O12 1.234(2) . ?
C30 C31 1.514(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 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
O1 Zn1 N3 99.25(5) . . ?
O1 Zn1 N2 137.48(6) . . ?
N3 Zn1 N2 122.63(6) . . ?
O1 Zn1 O3 98.66(5) . . ?
N3 Zn1 O3 91.45(5) . . ?
N2 Zn1 O3 88.15(5) . . ?
O1 Zn1 N1 85.10(5) . . ?
N3 Zn1 N1 89.67(5) . . ?
N2 Zn1 N1 87.88(5) . . ?
O3 Zn1 N1 175.85(5) . . ?
C12 N1 C11 118.51(15) . . ?
C12 N1 Zn1 110.92(10) . . ?
C11 N1 Zn1 109.61(10) . . ?
C2 C1 C10 120.51(19) . . ?
C2 C1 H1 119.7 . . ?
C10 C1 H1 119.7 . . ?
C1 C2 C3 120.78(17) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 121.44(19) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C11 118.79(18) . . ?
C3 C4 C14 122.73(17) . . ?
C11 C4 C14 118.28(15) . . ?
C6 C5 C12 118.74(16) . . ?
C6 C5 C17 121.51(16) . . ?
C12 C5 C17 119.68(15) . . ?
C5 C6 C7 122.07(17) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 120.29(17) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C13 120.35(17) . . ?
C7 C8 H8 119.8 . . ?
C13 C8 H8 119.8 . . ?
C10 C9 C13 120.30(16) . . ?
C10 C9 H9 119.8 . . ?
C13 C9 H9 119.8 . . ?
C9 C10 C1 123.29(17) . . ?
C9 C10 C11 118.12(16) . . ?
C1 C10 C11 118.59(17) . . ?
N1 C11 C10 122.49(16) . . ?
N1 C11 C4 117.72(16) . . ?
C10 C11 C4 119.79(16) . . ?
N1 C12 C5 118.20(15) . . ?
N1 C12 C13 122.43(15) . . ?
C5 C12 C13 119.37(15) . . ?
C9 C13 C8 122.78(16) . . ?
C9 C13 C12 118.07(16) . . ?
C8 C13 C12 119.12(16) . . ?
N2 C14 C4 114.94(14) . . ?
N2 C14 H14A 108.5 . . ?
C4 C14 H14A 108.5 . . ?
N2 C14 H14B 108.5 . . ?
C4 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C15 N2 C16 108.06(15) . . ?
C15 N2 C14 106.96(14) . . ?
C16 N2 C14 108.27(14) . . ?
C15 N2 Zn1 109.18(11) . . ?
C16 N2 Zn1 110.83(11) . . ?
C14 N2 Zn1 113.35(10) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C5 113.41(13) . . ?
N3 C17 H17A 108.9 . . ?
C5 C17 H17A 108.9 . . ?
N3 C17 H17B 108.9 . . ?
C5 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C18 N3 C19 107.35(14) . . ?
C18 N3 C17 107.63(13) . . ?
C19 N3 C17 109.37(14) . . ?
C18 N3 Zn1 112.33(11) . . ?
C19 N3 Zn1 107.77(11) . . ?
C17 N3 Zn1 112.24(10) . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O1 Zn1 112.23(11) . . ?
O2 C20 O1 123.34(17) . . ?
O2 C20 C21 120.39(16) . . ?
O1 C20 C21 116.21(16) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 O3 Zn1 135.22(11) . . ?
O3 C22 O4 123.11(16) . . ?
O3 C22 C23 120.87(17) . . ?
O4 C22 C23 116.02(16) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 O4 Zn2 120.30(11) . . ?
O4 Zn2 O8 98.88(6) . . ?
O4 Zn2 O5 120.78(6) . . ?
O8 Zn2 O5 109.13(6) . . ?
O4 Zn2 O9 99.97(5) . . ?
O8 Zn2 O9 123.77(6) . . ?
O5 Zn2 O9 105.29(6) . . ?
C24 O5 Zn2 129.36(12) . . ?
O6 C24 O5 125.60(16) . . ?
O6 C24 C25 118.00(16) . . ?
O5 C24 C25 116.40(16) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 O6 Zn3 136.99(12) . . ?
C26 O7 Zn3 131.49(12) . . ?
O7 C26 O8 125.36(17) . . ?
O7 C26 C27 117.54(16) . . ?
O8 C26 C27 117.09(16) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 O8 Zn2 136.34(12) . . ?
C28 O9 Zn2 132.15(12) . . ?
O10 C28 O9 125.27(16) . . ?
O10 C28 C29 117.64(16) . . ?
O9 C28 C29 117.08(16) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 O10 Zn3 135.61(12) . . ?
O7 Zn3 O11 112.73(6) . . ?
O7 Zn3 O10 125.73(6) . . ?
O11 Zn3 O10 105.94(6) . . ?
O7 Zn3 O6 101.71(6) . . ?
O11 Zn3 O6 101.80(5) . . ?
O10 Zn3 O6 106.06(6) . . ?
O7 Zn3 C30 99.48(6) . . ?
O11 Zn3 C30 28.76(6) . . ?
O10 Zn3 C30 96.58(6) . . ?
O6 Zn3 C30 130.44(6) . . ?
C30 O11 Zn3 103.86(11) . . ?
O12 C30 O11 123.08(17) . . ?
O12 C30 C31 121.03(18) . . ?
O11 C30 C31 115.87(17) . . ?
O12 C30 Zn3 75.72(11) . . ?
O11 C30 Zn3 47.37(8) . . ?
C31 C30 Zn3 163.10(15) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C10 C1 C2 C3 -1.0(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C11 1.0(3) . . . . ?
C2 C3 C4 C14 -173.77(17) . . . . ?
C12 C5 C6 C7 0.5(3) . . . . ?
C17 C5 C6 C7 177.43(16) . . . . ?
C5 C6 C7 C8 -2.2(3) . . . . ?
C6 C7 C8 C13 1.8(3) . . . . ?
C13 C9 C10 C1 177.28(16) . . . . ?
C13 C9 C10 C11 -2.6(2) . . . . ?
C2 C1 C10 C9 178.82(17) . . . . ?
C2 C1 C10 C11 -1.3(3) . . . . ?
C12 N1 C11 C10 -2.1(2) . . . . ?
Zn1 N1 C11 C10 126.56(14) . . . . ?
C12 N1 C11 C4 177.69(14) . . . . ?
Zn1 N1 C11 C4 -53.63(16) . . . . ?
C9 C10 C11 N1 3.2(2) . . . . ?
C1 C10 C11 N1 -176.68(15) . . . . ?
C9 C10 C11 C4 -176.65(15) . . . . ?
C1 C10 C11 C4 3.5(2) . . . . ?
C3 C4 C11 N1 176.86(15) . . . . ?
C14 C4 C11 N1 -8.2(2) . . . . ?
C3 C4 C11 C10 -3.3(2) . . . . ?
C14 C4 C11 C10 171.66(15) . . . . ?
C11 N1 C12 C5 -179.19(14) . . . . ?
Zn1 N1 C12 C5 52.74(17) . . . . ?
C11 N1 C12 C13 0.5(2) . . . . ?
Zn1 N1 C12 C13 -127.55(14) . . . . ?
C6 C5 C12 N1 -178.67(15) . . . . ?
C17 C5 C12 N1 4.3(2) . . . . ?
C6 C5 C12 C13 1.6(2) . . . . ?
C17 C5 C12 C13 -175.40(15) . . . . ?
C10 C9 C13 C8 -177.14(16) . . . . ?
C10 C9 C13 C12 1.1(2) . . . . ?
C7 C8 C13 C9 178.50(16) . . . . ?
C7 C8 C13 C12 0.3(2) . . . . ?
N1 C12 C13 C9 0.0(2) . . . . ?
C5 C12 C13 C9 179.70(15) . . . . ?
N1 C12 C13 C8 178.28(15) . . . . ?
C5 C12 C13 C8 -2.0(2) . . . . ?
C3 C4 C14 N2 -112.06(19) . . . . ?
C11 C4 C14 N2 73.2(2) . . . . ?
C4 C14 N2 C15 -170.05(15) . . . . ?
C4 C14 N2 C16 73.71(18) . . . . ?
C4 C14 N2 Zn1 -49.68(18) . . . . ?
C6 C5 C17 N3 110.84(18) . . . . ?
C12 C5 C17 N3 -72.2(2) . . . . ?
C5 C17 N3 C18 -179.10(15) . . . . ?
C5 C17 N3 C19 -62.77(18) . . . . ?
C5 C17 N3 Zn1 56.79(16) . . . . ?
Zn1 O1 C20 O2 -5.9(2) . . . . ?
Zn1 O1 C20 C21 171.52(13) . . . . ?
Zn1 O3 C22 O4 140.19(14) . . . . ?
Zn1 O3 C22 C23 -40.9(3) . . . . ?
O3 C22 O4 Zn2 32.3(2) . . . . ?
C23 C22 O4 Zn2 -146.63(16) . . . . ?
Zn2 O5 C24 O6 7.4(3) . . . . ?
Zn2 O5 C24 C25 -172.02(14) . . . . ?
O5 C24 O6 Zn3 5.5(3) . . . . ?
C25 C24 O6 Zn3 -175.11(14) . . . . ?
Zn3 O7 C26 O8 4.8(3) . . . . ?
Zn3 O7 C26 C27 -176.35(12) . . . . ?
O7 C26 O8 Zn2 -5.9(3) . . . . ?
C27 C26 O8 Zn2 175.24(13) . . . . ?
Zn2 O9 C28 O10 0.5(3) . . . . ?
Zn2 O9 C28 C29 179.16(12) . . . . ?
O9 C28 O10 Zn3 2.9(3) . . . . ?
C29 C28 O10 Zn3 -175.78(13) . . . . ?
Zn3 O11 C30 O12 -1.3(2) . . . . ?
Zn3 O11 C30 C31 177.36(15) . . . . ?

_refine_diff_density_max         0.646
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.054

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene/dimethylformamide'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_AcrNMe2_HCl
_database_code_depnum_ccdc_archive 'CCDC 1423219'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4,5-bis(N,N-dimethylaminemethylene)acridine hydrochloride '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N3, C H4 O, 2(Cl)'
_chemical_formula_sum            'C20 H29 Cl2 N3 O'
_chemical_formula_weight         398.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   16.700(3)
_cell_length_b                   11.503(2)
_cell_length_c                   10.836(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2081.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2682
_cell_measurement_theta_min      28.4155
_cell_measurement_theta_max      66.4135

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.905
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS-2015/1
_exptl_special_details           ?

# start Validation Reply Form
_vrf_PLAT910_AcrNMe2_HCl         
;
PROBLEM: Missing # of FCF Reflection(s) Below Th(Min) ... 285 Report
RESPONSE: The low completeness of the data set is due to an interruption 
of the cooling system during the measurement along with the loss of the crystal.
;
# end Validation Reply Form

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Copper Rotating Anode'
_diffrn_measurement_device_type  'SMART-3000 Turbo'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3602
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         28.413
_diffrn_reflns_theta_max         66.420
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.792
_diffrn_measured_fraction_theta_full 0.772
_diffrn_reflns_Laue_measured_fraction_max 0.792
_diffrn_reflns_Laue_measured_fraction_full 0.772
_diffrn_reflns_point_group_measured_fraction_max 0.470
_diffrn_reflns_point_group_measured_fraction_full 0.458
_reflns_number_total             1723
_reflns_number_gt                1676
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.122
_reflns_Friedel_fraction_max     0.109
_reflns_Friedel_fraction_full    0.106

_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 v2012.2'
_computing_cell_refinement       'SAINT V8.30C'
_computing_data_reduction        'SAINT V8.30C'
_computing_structure_solution    
'SHELXT (G.M.Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0182P)²+0.2011P] 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_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.008(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1723
_refine_ls_number_parameters     252
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0436
_refine_ls_wR_factor_gt          0.0433
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.43373(3) 0.49289(4) 0.47147(5) 0.02397(14) Uani 1 1 d . . . . .
Cl2 Cl 0.45608(3) -0.01747(3) 0.32726(4) 0.02309(14) Uani 1 1 d . . . . .
O1 O 0.63078(10) 0.06132(14) 0.34399(18) 0.0379(4) Uani 1 1 d . . . . .
H1A H 0.581(3) 0.025(3) 0.345(3) 0.042(7) Uiso 1 1 d . . . . .
C20 C 0.67532(18) 0.0132(2) 0.2468(3) 0.0424(6) Uani 1 1 d . . . . .
H20A H 0.7258 0.0557 0.2379 0.064 Uiso 1 1 calc R U . . .
H20B H 0.6446 0.0189 0.1700 0.064 Uiso 1 1 calc R U . . .
H20C H 0.6866 -0.0687 0.2647 0.064 Uiso 1 1 calc R U . . .
N1 N 0.62971(10) 0.52014(14) 0.60324(15) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.49976(11) 0.30291(15) 0.64510(16) 0.0219(3) Uani 1 1 d D . . . .
H2A H 0.4941(17) 0.365(2) 0.599(2) 0.022(6) Uiso 1 1 d D . . . .
N3 N 0.47516(10) 0.68652(15) 0.65560(16) 0.0219(3) Uani 1 1 d D . . . .
H3A H 0.4818(18) 0.623(2) 0.610(3) 0.029(6) Uiso 1 1 d D . . . .
C1 C 0.77244(13) 0.3302(2) 0.4324(2) 0.0293(5) Uani 1 1 d . . . . .
H1 H 0.8140 0.3348 0.3727 0.035 Uiso 1 1 calc R U . . .
C2 C 0.75223(13) 0.22588(19) 0.4815(2) 0.0332(5) Uani 1 1 d . . . . .
H2 H 0.7803 0.1578 0.4570 0.040 Uiso 1 1 calc R U . . .
C3 C 0.68911(14) 0.21784(19) 0.5695(2) 0.0295(5) Uani 1 1 d . . . . .
H3 H 0.6759 0.1440 0.6030 0.035 Uiso 1 1 calc R U . . .
C4 C 0.64705(13) 0.31349(17) 0.6073(2) 0.0231(4) Uani 1 1 d . . . . .
C5 C 0.61953(12) 0.72702(17) 0.62110(18) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.64740(14) 0.83541(18) 0.5910(2) 0.0285(5) Uani 1 1 d . . . . .
H6 H 0.6245 0.9018 0.6294 0.034 Uiso 1 1 calc R U . . .
C7 C 0.71007(14) 0.85038(19) 0.5032(2) 0.0324(5) Uani 1 1 d . . . . .
H7 H 0.7289 0.9263 0.4845 0.039 Uiso 1 1 calc R U . . .
C8 C 0.74289(14) 0.7571(2) 0.4462(2) 0.0309(5) Uani 1 1 d . . . . .
H8 H 0.7834 0.7682 0.3858 0.037 Uiso 1 1 calc R U . . .
C9 C 0.75365(13) 0.5431(2) 0.42781(19) 0.0264(4) Uani 1 1 d . . . . .
H9 H 0.7936 0.5506 0.3659 0.032 Uiso 1 1 calc R U . . .
C10 C 0.73163(11) 0.43321(17) 0.4701(2) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.66820(12) 0.42591(17) 0.55954(18) 0.0209(4) Uani 1 1 d . . . . .
C12 C 0.65459(12) 0.62603(17) 0.56568(18) 0.0211(4) Uani 1 1 d . . . . .
C13 C 0.71712(11) 0.64186(17) 0.4762(2) 0.0242(4) Uani 1 1 d . . . . .
C14 C 0.58204(13) 0.30346(17) 0.70251(19) 0.0220(4) Uani 1 1 d . . . . .
H14A H 0.5861 0.3695 0.7607 0.026 Uiso 1 1 calc R U . . .
H14B H 0.5897 0.2308 0.7501 0.026 Uiso 1 1 calc R U . . .
C15 C 0.43717(13) 0.3060(2) 0.7438(2) 0.0297(5) Uani 1 1 d . . . . .
H15A H 0.3843 0.3164 0.7060 0.044 Uiso 1 1 calc R U . . .
H15B H 0.4480 0.3709 0.8000 0.044 Uiso 1 1 calc R U . . .
H15C H 0.4381 0.2328 0.7900 0.044 Uiso 1 1 calc R U . . .
C16 C 0.48640(13) 0.20112(19) 0.5620(2) 0.0263(4) Uani 1 1 d . . . . .
H16A H 0.4324 0.2053 0.5269 0.039 Uiso 1 1 calc R U . . .
H16B H 0.4921 0.1290 0.6094 0.039 Uiso 1 1 calc R U . . .
H16C H 0.5260 0.2023 0.4953 0.039 Uiso 1 1 calc R U . . .
C17 C 0.55452(13) 0.71288(18) 0.71549(19) 0.0216(4) Uani 1 1 d . . . . .
H17A H 0.5499 0.7852 0.7645 0.026 Uiso 1 1 calc R U . . .
H17B H 0.5688 0.6489 0.7725 0.026 Uiso 1 1 calc R U . . .
C18 C 0.41289(14) 0.6611(2) 0.7509(2) 0.0305(5) Uani 1 1 d . . . . .
H18A H 0.3987 0.7330 0.7941 0.046 Uiso 1 1 calc R U . . .
H18B H 0.4340 0.6045 0.8102 0.046 Uiso 1 1 calc R U . . .
H18C H 0.3652 0.6290 0.7108 0.046 Uiso 1 1 calc R U . . .
C19 C 0.44878(15) 0.7832(2) 0.5732(2) 0.0313(5) Uani 1 1 d . . . . .
H19A H 0.4872 0.7921 0.5054 0.047 Uiso 1 1 calc R U . . .
H19B H 0.4461 0.8556 0.6206 0.047 Uiso 1 1 calc R U . . .
H19C H 0.3957 0.7653 0.5394 0.047 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.403(3) . ?
N1 C11 1.346(3) . ?
N1 C12 1.350(3) . ?
N2 C16 1.494(3) . ?
N2 C15 1.496(3) . ?
N2 C14 1.508(3) . ?
N3 C19 1.493(3) . ?
N3 C18 1.494(3) . ?
N3 C17 1.507(3) . ?
C1 C2 1.356(4) . ?
C1 C10 1.426(3) . ?
C2 C3 1.425(4) . ?
C3 C4 1.368(3) . ?
C4 C11 1.437(3) . ?
C4 C14 1.502(3) . ?
C5 C6 1.370(3) . ?
C5 C12 1.433(3) . ?
C5 C17 1.500(3) . ?
C6 C7 1.425(4) . ?
C7 C8 1.354(4) . ?
C8 C13 1.431(3) . ?
C9 C13 1.392(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.438(3) . ?
C12 C13 1.437(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C12 118.26(18) . . ?
C16 N2 C15 110.19(17) . . ?
C16 N2 C14 112.82(16) . . ?
C15 N2 C14 109.98(17) . . ?
C19 N3 C18 110.72(17) . . ?
C19 N3 C17 111.55(17) . . ?
C18 N3 C17 110.73(17) . . ?
C2 C1 C10 120.3(2) . . ?
C1 C2 C3 120.28(19) . . ?
C4 C3 C2 121.9(2) . . ?
C3 C4 C11 119.3(2) . . ?
C3 C4 C14 120.98(19) . . ?
C11 C4 C14 119.61(17) . . ?
C6 C5 C12 119.94(19) . . ?
C6 C5 C17 120.45(18) . . ?
C12 C5 C17 119.57(17) . . ?
C5 C6 C7 121.2(2) . . ?
C8 C7 C6 120.40(19) . . ?
C7 C8 C13 120.6(2) . . ?
C13 C9 C10 120.04(18) . . ?
C9 C10 C1 122.20(19) . . ?
C9 C10 C11 117.96(18) . . ?
C1 C10 C11 119.76(19) . . ?
N1 C11 C4 118.73(19) . . ?
N1 C11 C10 122.80(18) . . ?
C4 C11 C10 118.44(17) . . ?
N1 C12 C5 118.65(18) . . ?
N1 C12 C13 122.80(18) . . ?
C5 C12 C13 118.50(18) . . ?
C9 C13 C8 122.59(19) . . ?
C9 C13 C12 117.99(18) . . ?
C8 C13 C12 119.29(19) . . ?
C4 C14 N2 112.05(16) . . ?
C5 C17 N3 111.39(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 1.1(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C11 -1.7(3) . . . . ?
C2 C3 C4 C14 -178.5(2) . . . . ?
C12 C5 C6 C7 1.2(3) . . . . ?
C17 C5 C6 C7 178.9(2) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C13 -2.1(3) . . . . ?
C13 C9 C10 C1 -173.82(19) . . . . ?
C13 C9 C10 C11 2.9(3) . . . . ?
C2 C1 C10 C9 176.0(2) . . . . ?
C2 C1 C10 C11 -0.7(3) . . . . ?
C12 N1 C11 C4 174.46(17) . . . . ?
C12 N1 C11 C10 -3.3(3) . . . . ?
C3 C4 C11 N1 -175.87(19) . . . . ?
C14 C4 C11 N1 1.0(3) . . . . ?
C3 C4 C11 C10 2.0(3) . . . . ?
C14 C4 C11 C10 178.89(18) . . . . ?
C9 C10 C11 N1 0.1(3) . . . . ?
C1 C10 C11 N1 176.91(18) . . . . ?
C9 C10 C11 C4 -177.68(18) . . . . ?
C1 C10 C11 C4 -0.9(3) . . . . ?
C11 N1 C12 C5 -173.72(17) . . . . ?
C11 N1 C12 C13 3.6(3) . . . . ?
C6 C5 C12 N1 175.55(19) . . . . ?
C17 C5 C12 N1 -2.1(3) . . . . ?
C6 C5 C12 C13 -1.9(3) . . . . ?
C17 C5 C12 C13 -179.57(17) . . . . ?
C10 C9 C13 C8 173.2(2) . . . . ?
C10 C9 C13 C12 -2.6(3) . . . . ?
C7 C8 C13 C9 -174.5(2) . . . . ?
C7 C8 C13 C12 1.4(3) . . . . ?
N1 C12 C13 C9 -0.7(3) . . . . ?
C5 C12 C13 C9 176.66(18) . . . . ?
N1 C12 C13 C8 -176.69(19) . . . . ?
C5 C12 C13 C8 0.6(3) . . . . ?
C3 C4 C14 N2 -100.7(2) . . . . ?
C11 C4 C14 N2 82.4(2) . . . . ?
C16 N2 C14 C4 62.7(2) . . . . ?
C15 N2 C14 C4 -173.80(17) . . . . ?
C6 C5 C17 N3 104.0(2) . . . . ?
C12 C5 C17 N3 -78.3(2) . . . . ?
C19 N3 C17 C5 -61.8(2) . . . . ?
C18 N3 C17 C5 174.39(16) . . . . ?

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 H1A Cl2 0.93(4) 2.15(4) 3.0605(19) 166(3) .
N2 H2A Cl1 0.88(3) 2.26(3) 3.0874(19) 158(2) .
N3 H3A Cl1 0.88(3) 2.27(3) 3.0693(18) 150(3) .
C14 H14A Cl1 0.99 2.80 3.749(2) 161.1 2_665
C14 H14B Cl2 0.99 2.70 3.613(2) 153.0 2_655
C16 H16B Cl2 0.98 2.82 3.694(2) 148.5 2_655
C17 H17A Cl2 0.99 2.76 3.711(2) 161.6 2_665
C17 H17B Cl1 0.99 2.70 3.652(2) 160.4 2_665
C18 H18A O1 0.98 2.48 3.427(3) 163.5 2_665
C19 H19A Cl2 0.98 2.97 3.518(3) 116.8 1_565

_refine_diff_density_max         0.105
_refine_diff_density_min         -0.090
_refine_diff_density_rms         0.020

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_preparation       Luminescent
