# 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 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_trn002_p21n
_database_code_depnum_ccdc_archive 'CCDC 1451694'
_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
'[(N,N`-bis(5-triethylammoniummethylsalicylidene)-1,2-ethylenediiminato)nickel(II)] (ClO4)2'
_chemical_formula_moiety         'C30 H46 N4 Ni O2, 2(Cl O4)'
_chemical_formula_sum            'C30 H46 Cl2 N4 Ni O10'
_chemical_formula_weight         752.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.0932(6)
_cell_length_b                   15.4168(8)
_cell_length_c                   22.8812(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.2906(17)
_cell_angle_gamma                90
_cell_volume                     3557.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.314
_cell_measurement_theta_min      2.175
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0816 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.8843.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            28269
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.439
_diffrn_reflns_theta_min         1.781
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4670
_reflns_number_total             6432
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.775
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6432
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0707
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0766P)²+11.6114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1727
_refine_ls_wR_factor_ref         0.1909
_refine_special_details          
;
_olex2_refinement_description
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1A-C8A ∼ N1A-C8C ∼ N1B-C8B ∼ N1B-C8D
 with sigma of 0.02
 C8C-C8D ∼ C8A-C8B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C8A) = Uanis(C8D) = Uanis(C8B) = Uanis(C8C)
Uanis(C15C) = Uanis(C15A)
4. Others
 Fixed Sof: C8B(0.5) H8BA(0.5) H8BB(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5)
 H14E(0.5) H14F(0.5) H14C(0.5) H14D(0.5) C10C(0.5) H10C(0.5) H10D(0.5)
 C15C(0.5) H15D(0.5) H15E(0.5) H15F(0.5) C11A(0.5) H11D(0.5) H11E(0.5)
 H11F(0.5) C11C(0.5) H11G(0.5) H11H(0.5) H11I(0.5) C10A(0.5) H10E(0.5)
 H10F(0.5) C8C(0.5) H8CA(0.5) H8CB(0.5) C8D(0.5) H8DA(0.5) H8DB(0.5) C15A(0.5)
 H15G(0.5) H15H(0.5) H15I(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C8B(H8BA,H8BB), C8A(H8AA,H8AB), C10B(H10A,H10B), C9A(H9AA,H9AB), C9B(H9BA,
 H9BB), C14B(H14A,H14B), C14A(H14E,H14F), C14A(H14C,H14D), C10C(H10C,H10D),
 C12A(H12A,H12B), C12B(H12C,H12D), C10A(H10E,H10F), C8C(H8CA,H8CB), C8D(H8DA,
 H8DB)
5.b Aromatic/amide H refined with riding coordinates:
 C7B(H7B), C3B(H3B), C3A(H3A), C7A(H7A), C6A(H6A), C4B(H4B), C6B(H6B), C4A(H4A)
5.c Idealised Me refined as rotating group:
 C15B(H15A,H15B,H15C), C11B(H11A,H11B,H11C), C13A(H13A,H13B,H13C), C13B(H13D,
 H13E,H13F), C15C(H15D,H15E,H15F), C11A(H11D,H11E,H11F), C11C(H11G,H11H,H11I),
 C15A(H15G,H15H,H15I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.64858(6) 0.01720(5) 0.97832(3) 0.0392(2) Uani 1 1 d . . . . .
Cl2 Cl 0.75922(11) 0.50433(9) 0.88652(5) 0.0386(3) Uani 1 1 d . . . . .
Cl1 Cl 0.74318(12) -0.20202(10) 1.20492(5) 0.0416(3) Uani 1 1 d . . . . .
C2A C 0.5974(5) -0.0680(4) 0.8701(2) 0.0369(12) Uani 1 1 d . . . . .
O1B O 0.5767(4) 0.1264(2) 0.97107(15) 0.0424(9) Uani 1 1 d . . . . .
C1B C 0.6489(5) 0.1818(3) 1.0654(2) 0.0367(12) Uani 1 1 d . . . . .
O1A O 0.5913(3) 0.0038(2) 0.90175(15) 0.0415(9) Uani 1 1 d . . . . .
N1B N 0.7029(5) 0.0307(3) 1.0554(2) 0.0501(12) Uani 1 1 d D . . . .
O7 O 0.7106(4) 0.4993(4) 0.82737(18) 0.0733(15) Uani 1 1 d . . . . .
O9 O 0.6609(4) 0.4731(3) 0.92406(16) 0.0537(11) Uani 1 1 d . . . . .
O4 O 0.7911(4) -0.1173(3) 1.21848(18) 0.0650(12) Uani 1 1 d . . . . .
O6 O 0.8762(3) 0.4538(3) 0.8940(2) 0.0563(11) Uani 1 1 d . . . . .
O8 O 0.7882(4) 0.5924(3) 0.9009(2) 0.0687(13) Uani 1 1 d . . . . .
C2B C 0.5842(5) 0.1897(4) 1.0094(2) 0.0369(12) Uani 1 1 d . . . . .
N1A N 0.7222(5) -0.0922(3) 0.9854(2) 0.0523(13) Uani 1 1 d D . . . .
O3 O 0.6219(4) -0.2004(4) 1.17200(17) 0.0713(15) Uani 1 1 d . . . . .
O5 O 0.7307(5) -0.2489(3) 1.25780(18) 0.0714(14) Uani 1 1 d . . . . .
C7B C 0.7017(5) 0.0998(4) 1.0858(2) 0.0481(14) Uani 1 1 d . . . . .
H7B H 0.7381 0.0972 1.1246 0.058 Uiso 1 1 calc R . . . .
C3B C 0.5256(5) 0.2698(4) 0.9955(2) 0.0367(12) Uani 1 1 d . . . . .
H3B H 0.4799 0.2766 0.9586 0.044 Uiso 1 1 calc R . . . .
C3A C 0.5371(5) -0.0693(4) 0.8136(2) 0.0360(12) Uani 1 1 d . . . . .
H3A H 0.4925 -0.0188 0.7994 0.043 Uiso 1 1 calc R . . . .
O2 O 0.8387(4) -0.2434(4) 1.17039(19) 0.0738(15) Uani 1 1 d . . . . .
C1A C 0.6615(5) -0.1442(4) 0.8893(2) 0.0386(12) Uani 1 1 d . . . . .
C7A C 0.7196(6) -0.1526(4) 0.9467(3) 0.0507(15) Uani 1 1 d . . . . .
H7A H 0.7591 -0.2066 0.9572 0.061 Uiso 1 1 calc R . . . .
C5A C 0.6060(5) -0.2170(3) 0.7976(2) 0.0372(12) Uani 1 1 d . . . . .
C5B C 0.6020(4) 0.3314(3) 1.0878(2) 0.0330(11) Uani 1 1 d . . . . .
C6A C 0.6625(5) -0.2172(4) 0.8533(2) 0.0410(13) Uani 1 1 d . . . . .
H6A H 0.7036 -0.2687 0.8677 0.049 Uiso 1 1 calc R . . . .
C4B C 0.5324(4) 0.3386(4) 1.0335(2) 0.0344(11) Uani 1 1 d . . . . .
H4B H 0.4898 0.3917 1.0230 0.041 Uiso 1 1 calc R . . . .
C6B C 0.6555(5) 0.2534(4) 1.1029(2) 0.0374(12) Uani 1 1 d . . . . .
H6B H 0.6990 0.2472 1.1402 0.045 Uiso 1 1 calc R . . . .
C4A C 0.5409(5) -0.1409(3) 0.7786(2) 0.0360(12) Uani 1 1 d . . . . .
H4A H 0.4987 -0.1393 0.7408 0.043 Uiso 1 1 calc R . . . .
C8B C 0.730(4) -0.0592(9) 1.0789(8) 0.080(3) Uani 0.5 1 d D . P A 1
H8BA H 0.7766 -0.0558 1.1176 0.096 Uiso 0.5 1 calc R . P A 1
H8BB H 0.6448 -0.0904 1.0836 0.096 Uiso 0.5 1 calc R . P A 1
C8A C 0.808(2) -0.1041(18) 1.0390(7) 0.080(3) Uani 0.5 1 d D . P A 1
H8AA H 0.8191 -0.1660 1.0495 0.096 Uiso 0.5 1 calc R . P A 1
H8AB H 0.8962 -0.0768 1.0354 0.096 Uiso 0.5 1 calc R . P A 1
N2B N 0.7249(4) 0.4704(3) 1.11977(17) 0.0370(10) Uani 1 1 d . . . . .
N2A N 0.7196(4) -0.2990(3) 0.7150(2) 0.0427(11) Uani 1 1 d . . . . .
C10B C 0.6881(5) 0.5256(4) 1.0673(2) 0.0369(12) Uani 1 1 d . . . . .
H10A H 0.5984 0.5498 1.0721 0.044 Uiso 1 1 calc R . . . .
H10B H 0.6843 0.4883 1.0320 0.044 Uiso 1 1 calc R . . . .
C9A C 0.6129(5) -0.2974(3) 0.7612(2) 0.0352(11) Uani 1 1 d . . . . .
H9AA H 0.5254 -0.3061 0.7410 0.042 Uiso 1 1 calc R . . . .
H9AB H 0.6284 -0.3474 0.7878 0.042 Uiso 1 1 calc R . . . .
C9B C 0.6133(5) 0.4053(4) 1.1300(2) 0.0376(12) Uani 1 1 d . . . . .
H9BA H 0.6264 0.3813 1.1699 0.045 Uiso 1 1 calc R . . . .
H9BB H 0.5280 0.4372 1.1286 0.045 Uiso 1 1 calc R . . . .
C14B C 0.8574(5) 0.4237(4) 1.1124(3) 0.0504(15) Uani 1 1 d . . . . .
H14A H 0.9296 0.4637 1.1251 0.060 Uiso 1 1 calc R . . . .
H14B H 0.8611 0.3734 1.1393 0.060 Uiso 1 1 calc R . . . .
C14A C 0.6790(7) -0.2369(4) 0.6672(3) 0.0574(17) Uani 1 1 d . . . . .
H14E H 0.6682 -0.1777 0.6831 0.069 Uiso 0.5 1 calc R . P B 2
H14F H 0.5941 -0.2552 0.6478 0.069 Uiso 0.5 1 calc R . P B 2
H14C H 0.6954 -0.1776 0.6825 0.069 Uiso 0.5 1 calc R . P C 1
H14D H 0.5819 -0.2427 0.6605 0.069 Uiso 0.5 1 calc R . P C 1
C10C C 0.856(2) -0.2799(18) 0.7533(9) 0.053(6) Uani 0.5 1 d . . P D 2
H10C H 0.8498 -0.3087 0.7918 0.064 Uiso 0.5 1 calc R . P D 2
H10D H 0.9305 -0.3075 0.7333 0.064 Uiso 0.5 1 calc R . P D 2
C15B C 0.8864(5) 0.3912(5) 1.0517(3) 0.0615(18) Uani 1 1 d . . . . .
H15A H 0.9011 0.4408 1.0259 0.092 Uiso 1 1 calc GR . . . .
H15B H 0.8109 0.3572 1.0361 0.092 Uiso 1 1 calc GR . . . .
H15C H 0.9659 0.3547 1.0537 0.092 Uiso 1 1 calc GR . . . .
C11B C 0.7837(5) 0.5999(4) 1.0574(2) 0.0464(14) Uani 1 1 d . . . . .
H11A H 0.7621 0.6270 1.0194 0.070 Uiso 1 1 calc GR . . . .
H11B H 0.8746 0.5776 1.0578 0.070 Uiso 1 1 calc GR . . . .
H11C H 0.7759 0.6430 1.0885 0.070 Uiso 1 1 calc GR . . . .
C12A C 0.7333(5) -0.3905(4) 0.6931(3) 0.0482(14) Uani 1 1 d . . . . .
H12A H 0.8074 -0.3923 0.6660 0.058 Uiso 1 1 calc R . . . .
H12B H 0.7577 -0.4283 0.7268 0.058 Uiso 1 1 calc R . . . .
C12B C 0.7428(6) 0.5239(4) 1.1750(2) 0.0562(17) Uani 1 1 d . . . . .
H12C H 0.7749 0.4855 1.2072 0.067 Uiso 1 1 calc R . . . .
H12D H 0.8122 0.5681 1.1690 0.067 Uiso 1 1 calc R . . . .
C13A C 0.6119(6) -0.4274(5) 0.6622(3) 0.0607(17) Uani 1 1 d . . . . .
H13A H 0.5875 -0.3913 0.6282 0.091 Uiso 1 1 calc GR . . . .
H13B H 0.5385 -0.4283 0.6890 0.091 Uiso 1 1 calc GR . . . .
H13C H 0.6303 -0.4866 0.6493 0.091 Uiso 1 1 calc GR . . . .
C13B C 0.6192(8) 0.5691(5) 1.1934(3) 0.075(2) Uani 1 1 d . . . . .
H13D H 0.5808 0.6023 1.1603 0.113 Uiso 1 1 calc GR . . . .
H13E H 0.6413 0.6086 1.2259 0.113 Uiso 1 1 calc GR . . . .
H13F H 0.5549 0.5259 1.2059 0.113 Uiso 1 1 calc GR . . . .
C15C C 0.790(3) -0.239(2) 0.6246(9) 0.065(5) Uani 0.5 1 d . . P E 2
H15D H 0.8742 -0.2268 0.6455 0.098 Uiso 0.5 1 calc GR . P E 2
H15E H 0.7730 -0.1952 0.5942 0.098 Uiso 0.5 1 calc GR . P E 2
H15F H 0.7931 -0.2966 0.6065 0.098 Uiso 0.5 1 calc GR . P E 2
C11A C 0.9247(11) -0.3205(8) 0.7782(5) 0.044(3) Uani 0.5 1 d . . P D 1
H11D H 0.9623 -0.3718 0.7598 0.067 Uiso 0.5 1 calc GR . P D 1
H11E H 0.8620 -0.3387 0.8075 0.067 Uiso 0.5 1 calc GR . P D 1
H11F H 0.9961 -0.2864 0.7973 0.067 Uiso 0.5 1 calc GR . P D 1
C11C C 0.8909(15) -0.1864(11) 0.7639(7) 0.082(5) Uani 0.5 1 d . . P D 2
H11G H 0.8951 -0.1562 0.7263 0.123 Uiso 0.5 1 calc GR . P D 2
H11H H 0.9772 -0.1826 0.7849 0.123 Uiso 0.5 1 calc GR . P D 2
H11I H 0.8230 -0.1593 0.7873 0.123 Uiso 0.5 1 calc GR . P D 2
C10A C 0.851(2) -0.2642(17) 0.7308(8) 0.040(4) Uani 0.5 1 d . . P D 1
H10E H 0.8418 -0.2043 0.7457 0.048 Uiso 0.5 1 calc R . P D 1
H10F H 0.9045 -0.2618 0.6955 0.048 Uiso 0.5 1 calc R . P D 1
C8C C 0.766(2) -0.1129(18) 1.0476(6) 0.080(3) Uani 0.5 1 d D . P A 2
H8CA H 0.7192 -0.1659 1.0598 0.096 Uiso 0.5 1 calc R . P A 2
H8CB H 0.8621 -0.1264 1.0485 0.096 Uiso 0.5 1 calc R . P A 2
C8D C 0.744(4) -0.0479(9) 1.0884(8) 0.080(3) Uani 0.5 1 d D . P A 2
H8DA H 0.8266 -0.0364 1.1121 0.096 Uiso 0.5 1 calc R . P A 2
H8DB H 0.6743 -0.0658 1.1149 0.096 Uiso 0.5 1 calc R . P A 2
C15A C 0.744(3) -0.242(2) 0.6046(9) 0.065(5) Uani 0.5 1 d . . P E 1
H15G H 0.8373 -0.2248 0.6084 0.098 Uiso 0.5 1 calc GR . P E 1
H15H H 0.6964 -0.2033 0.5772 0.098 Uiso 0.5 1 calc GR . P E 1
H15I H 0.7379 -0.3019 0.5899 0.098 Uiso 0.5 1 calc GR . P E 1


_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
Ni1 O1B 1.838(4) . ?
Ni1 O1A 1.834(4) . ?
Ni1 N1B 1.838(5) . ?
Ni1 N1A 1.847(5) . ?
Cl2 O7 1.423(4) . ?
Cl2 O9 1.423(4) . ?
Cl2 O6 1.419(4) . ?
Cl2 O8 1.425(5) . ?
Cl1 O4 1.423(5) . ?
Cl1 O3 1.412(4) . ?
Cl1 O5 1.420(4) . ?
Cl1 O2 1.422(4) . ?
C2A O1A 1.324(7) . ?
C2A C3A 1.407(7) . ?
C2A C1A 1.403(7) . ?
O1B C2B 1.313(6) . ?
C1B C2B 1.421(7) . ?
C1B C7B 1.442(8) . ?
C1B C6B 1.397(7) . ?
N1B C7B 1.272(8) . ?
N1B C8B 1.507(12) . ?
N1B C8D 1.479(12) . ?
C2B C3B 1.400(7) . ?
N1A C7A 1.285(8) . ?
N1A C8A 1.486(12) . ?
N1A C8C 1.507(12) . ?
C3B C4B 1.372(7) . ?
C3A C4A 1.366(7) . ?
C1A C7A 1.424(7) . ?
C1A C6A 1.394(8) . ?
C5A C6A 1.375(7) . ?
C5A C4A 1.405(7) . ?
C5A C9A 1.497(7) . ?
C5B C4B 1.408(6) . ?
C5B C6B 1.357(7) . ?
C5B C9B 1.495(7) . ?
C8B C8A 1.413(19) . ?
N2B C10B 1.507(6) . ?
N2B C9B 1.533(6) . ?
N2B C14B 1.534(7) . ?
N2B C12B 1.515(7) . ?
N2A C9A 1.539(6) . ?
N2A C14A 1.497(7) . ?
N2A C10C 1.63(2) . ?
N2A C12A 1.506(7) . ?
N2A C10A 1.46(3) . ?
C10B C11B 1.520(7) . ?
C14B C15B 1.515(9) . ?
C14A C15C 1.51(3) . ?
C14A C15A 1.60(3) . ?
C10C C11C 1.50(3) . ?
C12A C13A 1.503(8) . ?
C12B C13B 1.503(10) . ?
C11A C10A 1.555(18) . ?
C8C C8D 1.393(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1B Ni1 N1B 94.83(19) . . ?
O1B Ni1 N1A 179.5(2) . . ?
O1A Ni1 O1B 84.80(16) . . ?
O1A Ni1 N1B 179.0(2) . . ?
O1A Ni1 N1A 95.22(19) . . ?
N1B Ni1 N1A 85.2(2) . . ?
O7 Cl2 O8 109.3(3) . . ?
O9 Cl2 O7 109.5(3) . . ?
O9 Cl2 O8 109.0(3) . . ?
O6 Cl2 O7 109.7(3) . . ?
O6 Cl2 O9 109.8(2) . . ?
O6 Cl2 O8 109.5(3) . . ?
O3 Cl1 O4 112.4(3) . . ?
O3 Cl1 O5 111.0(3) . . ?
O3 Cl1 O2 107.7(3) . . ?
O5 Cl1 O4 108.9(3) . . ?
O5 Cl1 O2 109.3(3) . . ?
O2 Cl1 O4 107.5(3) . . ?
O1A C2A C3A 119.1(5) . . ?
O1A C2A C1A 124.1(5) . . ?
C1A C2A C3A 116.9(5) . . ?
C2B O1B Ni1 127.5(3) . . ?
C2B C1B C7B 121.1(5) . . ?
C6B C1B C2B 119.6(5) . . ?
C6B C1B C7B 119.2(5) . . ?
C2A O1A Ni1 126.6(3) . . ?
C7B N1B Ni1 127.6(4) . . ?
C7B N1B C8B 125.6(8) . . ?
C7B N1B C8D 114.6(8) . . ?
C8B N1B Ni1 106.2(7) . . ?
C8D N1B Ni1 117.6(7) . . ?
O1B C2B C1B 123.5(5) . . ?
O1B C2B C3B 119.4(4) . . ?
C3B C2B C1B 117.1(5) . . ?
C7A N1A Ni1 127.2(4) . . ?
C7A N1A C8A 118.3(11) . . ?
C7A N1A C8C 119.5(11) . . ?
C8A N1A Ni1 113.9(11) . . ?
C8C N1A Ni1 112.3(10) . . ?
N1B C7B C1B 124.8(5) . . ?
C4B C3B C2B 121.8(4) . . ?
C4A C3A C2A 121.9(5) . . ?
C2A C1A C7A 122.2(5) . . ?
C6A C1A C2A 120.4(5) . . ?
C6A C1A C7A 117.3(5) . . ?
N1A C7A C1A 124.5(5) . . ?
C6A C5A C4A 117.4(5) . . ?
C6A C5A C9A 119.1(5) . . ?
C4A C5A C9A 123.4(5) . . ?
C4B C5B C9B 122.1(5) . . ?
C6B C5B C4B 118.3(5) . . ?
C6B C5B C9B 119.5(4) . . ?
C5A C6A C1A 122.2(5) . . ?
C3B C4B C5B 120.6(5) . . ?
C5B C6B C1B 122.4(4) . . ?
C3A C4A C5A 121.1(5) . . ?
C8A C8B N1B 108(2) . . ?
C8B C8A N1A 98.5(13) . . ?
C10B N2B C9B 109.4(4) . . ?
C10B N2B C14B 111.4(4) . . ?
C10B N2B C12B 112.0(4) . . ?
C9B N2B C14B 111.0(4) . . ?
C12B N2B C9B 107.0(4) . . ?
C12B N2B C14B 105.8(4) . . ?
C9A N2A C10C 103.2(9) . . ?
C14A N2A C9A 108.2(4) . . ?
C14A N2A C10C 118.5(9) . . ?
C14A N2A C12A 112.5(5) . . ?
C12A N2A C9A 108.6(4) . . ?
C12A N2A C10C 105.1(11) . . ?
C10A N2A C9A 118.5(9) . . ?
C10A N2A C14A 99.5(8) . . ?
C10A N2A C12A 109.3(11) . . ?
N2B C10B C11B 114.0(4) . . ?
C5A C9A N2A 116.4(4) . . ?
C5B C9B N2B 116.0(4) . . ?
C15B C14B N2B 117.2(4) . . ?
N2A C14A C15C 105.6(10) . . ?
N2A C14A C15A 120.7(11) . . ?
C11C C10C N2A 116.5(17) . . ?
C13A C12A N2A 115.3(5) . . ?
C13B C12B N2B 114.4(5) . . ?
N2A C10A C11A 111.8(14) . . ?
C8D C8C N1A 115.6(15) . . ?
C8C C8D N1B 107.3(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
Ni1 O1B C2B C1B -1.9(7) . . . . ?
Ni1 O1B C2B C3B 178.4(3) . . . . ?
Ni1 N1B C7B C1B 3.7(9) . . . . ?
Ni1 N1B C8B C8A 48(3) . . . . ?
Ni1 N1B C8D C8C 16(4) . . . . ?
Ni1 N1A C7A C1A 2.3(9) . . . . ?
Ni1 N1A C8A C8B 41(2) . . . . ?
Ni1 N1A C8C C8D 0(3) . . . . ?
C2A C3A C4A C5A -0.2(7) . . . . ?
C2A C1A C7A N1A -1.8(9) . . . . ?
C2A C1A C6A C5A 2.4(8) . . . . ?
O1B Ni1 O1A C2A -175.1(4) . . . . ?
O1B Ni1 N1B C7B -8.2(6) . . . . ?
O1B Ni1 N1B C8B 163.1(16) . . . . ?
O1B Ni1 N1B C8D 167.0(18) . . . . ?
O1B C2B C3B C4B -178.9(4) . . . . ?
C1B C2B C3B C4B 1.4(7) . . . . ?
O1A Ni1 O1B C2B -173.6(4) . . . . ?
O1A Ni1 N1A C7A -3.4(6) . . . . ?
O1A Ni1 N1A C8A 167.6(10) . . . . ?
O1A Ni1 N1A C8C -171.8(11) . . . . ?
O1A C2A C3A C4A 179.4(4) . . . . ?
O1A C2A C1A C7A 4.0(8) . . . . ?
O1A C2A C1A C6A 179.6(5) . . . . ?
N1B Ni1 O1B C2B 7.3(4) . . . . ?
N1B Ni1 N1A C7A 175.6(6) . . . . ?
N1B Ni1 N1A C8A -13.3(11) . . . . ?
N1B Ni1 N1A C8C 7.2(11) . . . . ?
N1B C8B C8A N1A -54(3) . . . . ?
C2B C1B C7B N1B 4.5(9) . . . . ?
C2B C1B C6B C5B 0.0(7) . . . . ?
C2B C3B C4B C5B 1.4(7) . . . . ?
N1A Ni1 O1A C2A 5.4(4) . . . . ?
N1A Ni1 N1B C7B 171.3(6) . . . . ?
N1A Ni1 N1B C8B -17.4(16) . . . . ?
N1A Ni1 N1B C8D -13.5(18) . . . . ?
N1A C8C C8D N1B -9(4) . . . . ?
C7B C1B C2B O1B -5.4(8) . . . . ?
C7B C1B C2B C3B 174.3(5) . . . . ?
C7B C1B C6B C5B -176.6(5) . . . . ?
C7B N1B C8B C8A -140.5(14) . . . . ?
C7B N1B C8D C8C -168(2) . . . . ?
C3A C2A O1A Ni1 173.9(3) . . . . ?
C3A C2A C1A C7A -176.4(5) . . . . ?
C3A C2A C1A C6A -0.7(7) . . . . ?
C1A C2A O1A Ni1 -6.4(7) . . . . ?
C1A C2A C3A C4A -0.3(7) . . . . ?
C7A N1A C8A C8B -147.3(19) . . . . ?
C7A N1A C8C C8D -169(3) . . . . ?
C7A C1A C6A C5A 178.2(5) . . . . ?
C6A C1A C7A N1A -177.6(6) . . . . ?
C6A C5A C4A C3A 1.7(7) . . . . ?
C6A C5A C9A N2A -100.6(5) . . . . ?
C4B C5B C6B C1B 2.9(7) . . . . ?
C4B C5B C9B N2B -84.2(5) . . . . ?
C6B C1B C2B O1B 178.1(4) . . . . ?
C6B C1B C2B C3B -2.1(7) . . . . ?
C6B C1B C7B N1B -179.0(5) . . . . ?
C6B C5B C4B C3B -3.6(7) . . . . ?
C6B C5B C9B N2B 98.4(5) . . . . ?
C4A C5A C6A C1A -2.8(7) . . . . ?
C4A C5A C9A N2A 81.3(6) . . . . ?
C8B N1B C7B C1B -166.0(18) . . . . ?
C8B N1B C8D C8C 34(11) . . . . ?
C8A N1A C7A C1A -168.3(12) . . . . ?
C8A N1A C8C C8D 99(8) . . . . ?
C10B N2B C9B C5B 73.6(5) . . . . ?
C10B N2B C14B C15B -37.1(7) . . . . ?
C10B N2B C12B C13B 63.6(6) . . . . ?
C9A C5A C6A C1A 179.0(4) . . . . ?
C9A C5A C4A C3A 179.8(4) . . . . ?
C9A N2A C14A C15C 178.0(12) . . . . ?
C9A N2A C14A C15A -162.3(13) . . . . ?
C9A N2A C10C C11C -85.9(15) . . . . ?
C9A N2A C12A C13A 63.1(6) . . . . ?
C9A N2A C10A C11A 66.9(19) . . . . ?
C9B C5B C4B C3B 179.1(4) . . . . ?
C9B C5B C6B C1B -179.7(4) . . . . ?
C9B N2B C10B C11B 172.8(4) . . . . ?
C9B N2B C14B C15B 85.1(6) . . . . ?
C9B N2B C12B C13B -56.3(6) . . . . ?
C14B N2B C10B C11B -64.1(6) . . . . ?
C14B N2B C9B C5B -49.8(5) . . . . ?
C14B N2B C12B C13B -174.8(5) . . . . ?
C14A N2A C9A C5A -70.8(6) . . . . ?
C14A N2A C10C C11C 34(2) . . . . ?
C14A N2A C12A C13A -56.6(6) . . . . ?
C14A N2A C10A C11A -176.2(14) . . . . ?
C10C N2A C9A C5A 55.6(11) . . . . ?
C10C N2A C14A C15C 61.2(17) . . . . ?
C10C N2A C14A C15A 80.8(18) . . . . ?
C10C N2A C12A C13A 173.0(9) . . . . ?
C10C N2A C10A C11A 23(4) . . . . ?
C12A N2A C9A C5A 166.8(4) . . . . ?
C12A N2A C14A C15C -61.9(13) . . . . ?
C12A N2A C14A C15A -42.3(14) . . . . ?
C12A N2A C10C C11C 160.3(14) . . . . ?
C12A N2A C10A C11A -58.2(16) . . . . ?
C12B N2B C10B C11B 54.3(6) . . . . ?
C12B N2B C9B C5B -164.8(5) . . . . ?
C12B N2B C14B C15B -159.1(5) . . . . ?
C10A N2A C9A C5A 41.4(12) . . . . ?
C10A N2A C14A C15C 53.7(16) . . . . ?
C10A N2A C14A C15A 73.3(17) . . . . ?
C10A N2A C10C C11C 55(5) . . . . ?
C10A N2A C12A C13A -166.2(8) . . . . ?
C8C N1A C7A C1A 170.0(11) . . . . ?
C8C N1A C8A C8B -48(4) . . . . ?
C8D N1B C7B C1B -171.6(18) . . . . ?
C8D N1B C8B C8A -115(15) . . . . ?

####################################################################### 
# 
# 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_trn003b_p-1
_database_code_depnum_ccdc_archive 'CCDC 1451695'
_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
"[(N,N'-bis(5-triethylammoniummethylsalicylidene)-1,2-ethylenediiminato)copper(II)](ClO4)2"
_chemical_formula_moiety         'C30 H46 Cu N4 O2, 2(Cl O4)'
_chemical_formula_sum            'C30 H46 Cl2 Cu N4 O10'
_chemical_formula_weight         757.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2787(13)
_cell_length_b                   12.812(2)
_cell_length_c                   16.033(3)
_cell_angle_alpha                70.114(8)
_cell_angle_beta                 82.910(7)
_cell_angle_gamma                87.960(7)
_cell_volume                     1778.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.52
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  0.7254
_exptl_absorpt_correction_T_min  0.5589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1700 before and 0.1112 after correction.
The Ratio of minimum to maximum transmission is 0.7705.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             794
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1462
_diffrn_reflns_av_unetI/netI     0.1229
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41294
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.456
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4906
_reflns_number_total             6415
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         6415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0828
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1550P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2265
_refine_ls_wR_factor_ref         0.2385
_refine_special_details          SQUEEZE
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.53273(6) 0.74585(4) 0.50675(3) 0.0264(2) Uani 1 1 d . . . . .
Cl2 Cl -0.14670(17) -0.13489(14) 0.86759(10) 0.0544(4) Uani 1 1 d . . . . .
O1B O 0.3608(3) 0.6574(2) 0.5352(2) 0.0296(7) Uani 1 1 d . . . . .
N1B N 0.6526(4) 0.6227(3) 0.5662(2) 0.0298(8) Uani 1 1 d . . . . .
N2A N 0.7121(4) 1.3516(3) 0.1765(2) 0.0305(9) Uani 1 1 d . . . . .
O1A O 0.4417(3) 0.8632(3) 0.4235(2) 0.0301(7) Uani 1 1 d . . . . .
N1A N 0.6956(4) 0.8367(3) 0.5068(2) 0.0293(8) Uani 1 1 d . . . . .
C2A C 0.4876(5) 0.9672(4) 0.3861(3) 0.0283(10) Uani 1 1 d . . . . .
C6A C 0.6503(5) 1.1234(4) 0.3638(3) 0.0286(10) Uani 1 1 d . . . . .
H6A H 0.7329 1.1519 0.3787 0.034 Uiso 1 1 calc R . . . .
C1B C 0.4679(5) 0.4808(4) 0.6100(3) 0.0270(10) Uani 1 1 d . . . . .
C1A C 0.6153(5) 1.0098(4) 0.4056(3) 0.0275(10) Uani 1 1 d . . . . .
C6B C 0.4440(5) 0.3657(4) 0.6543(3) 0.0295(10) Uani 1 1 d . . . . .
H6B H 0.5254 0.3192 0.6702 0.035 Uiso 1 1 calc R . . . .
C9A C 0.6033(5) 1.3171(4) 0.2601(3) 0.0282(10) Uani 1 1 d . . . . .
H9AA H 0.6409 1.3420 0.3055 0.034 Uiso 1 1 calc R . . . .
H9AB H 0.5117 1.3573 0.2454 0.034 Uiso 1 1 calc R . . . .
C4A C 0.4467(5) 1.1511(4) 0.2809(3) 0.0312(10) Uani 1 1 d . . . . .
H4A H 0.3901 1.1986 0.2379 0.037 Uiso 1 1 calc R . . . .
C7A C 0.7111(5) 0.9414(4) 0.4658(3) 0.0302(10) Uani 1 1 d . . . . .
H7A H 0.7923 0.9767 0.4760 0.036 Uiso 1 1 calc R . . . .
C7B C 0.6150(5) 0.5211(4) 0.6004(3) 0.0291(10) Uani 1 1 d . . . . .
H7B H 0.6883 0.4681 0.6209 0.035 Uiso 1 1 calc R . . . .
N2B N 0.2836(5) 0.1521(3) 0.8224(3) 0.0381(10) Uani 1 1 d . . . . .
C2B C 0.3490(5) 0.5498(4) 0.5799(3) 0.0255(9) Uani 1 1 d . . . . .
C3B C 0.2118(5) 0.4988(4) 0.6010(3) 0.0307(10) Uani 1 1 d . . . . .
H3B H 0.1296 0.5427 0.5817 0.037 Uiso 1 1 calc R . . . .
C5A C 0.5685(5) 1.1949(4) 0.3018(3) 0.0272(9) Uani 1 1 d . . . . .
C9B C 0.2891(6) 0.1942(4) 0.7208(3) 0.0341(11) Uani 1 1 d . . . . .
H9BA H 0.3700 0.1567 0.6961 0.041 Uiso 1 1 calc R . . . .
H9BB H 0.1979 0.1717 0.7051 0.041 Uiso 1 1 calc R . . . .
C8B C 0.8021(5) 0.6569(4) 0.5621(3) 0.0308(10) Uani 1 1 d . . . . .
H8BA H 0.8585 0.6561 0.5057 0.037 Uiso 1 1 calc R . . . .
H8BB H 0.8483 0.6052 0.6127 0.037 Uiso 1 1 calc R . . . .
C5B C 0.3086(5) 0.3187(4) 0.6752(3) 0.0303(10) Uani 1 1 d . . . . .
C3A C 0.4072(5) 1.0411(4) 0.3212(3) 0.0317(10) Uani 1 1 d . . . . .
H3A H 0.3244 1.0142 0.3051 0.038 Uiso 1 1 calc R . . . .
C8A C 0.7997(5) 0.7740(4) 0.5667(3) 0.0322(10) Uani 1 1 d . . . . .
H8AA H 0.7687 0.7721 0.6286 0.039 Uiso 1 1 calc R . . . .
H8AB H 0.8974 0.8086 0.5471 0.039 Uiso 1 1 calc R . . . .
C10A C 0.8595(5) 1.3069(4) 0.1984(3) 0.0389(12) Uani 1 1 d . . . . .
H10A H 0.9268 1.3281 0.1422 0.047 Uiso 1 1 calc R . . . .
H10B H 0.8532 1.2248 0.2219 0.047 Uiso 1 1 calc R . . . .
C4B C 0.1920(5) 0.3882(4) 0.6483(3) 0.0336(11) Uani 1 1 d . . . . .
H4B H 0.0963 0.3582 0.6631 0.040 Uiso 1 1 calc R . . . .
C12A C 0.7090(6) 1.4789(4) 0.1401(3) 0.0398(12) Uani 1 1 d . . . . .
H12A H 0.6104 1.5029 0.1242 0.048 Uiso 1 1 calc R . . . .
H12B H 0.7276 1.5072 0.1881 0.048 Uiso 1 1 calc R . . . .
C12B C 0.2624(7) 0.0270(4) 0.8522(3) 0.0448(13) Uani 1 1 d . . . . .
H12C H 0.1679 0.0116 0.8359 0.054 Uiso 1 1 calc R . . . .
H12D H 0.3394 -0.0037 0.8188 0.054 Uiso 1 1 calc R . . . .
C14A C 0.6726(6) 1.3037(4) 0.1077(3) 0.0359(11) Uani 1 1 d . . . . .
H14A H 0.7550 1.3174 0.0597 0.043 Uiso 1 1 calc R . . . .
H14B H 0.6616 1.2223 0.1366 0.043 Uiso 1 1 calc R . . . .
C13A C 0.8186(8) 1.5314(5) 0.0588(4) 0.0566(16) Uani 1 1 d . . . . .
H13A H 0.8081 1.4982 0.0131 0.085 Uiso 1 1 calc GR . . . .
H13B H 0.9171 1.5184 0.0762 0.085 Uiso 1 1 calc GR . . . .
H13C H 0.8013 1.6115 0.0348 0.085 Uiso 1 1 calc GR . . . .
C13B C 0.2657(9) -0.0334(5) 0.9513(4) 0.0635(19) Uani 1 1 d . . . . .
H13D H 0.2462 -0.1126 0.9652 0.095 Uiso 1 1 calc GR . . . .
H13E H 0.1915 -0.0027 0.9853 0.095 Uiso 1 1 calc GR . . . .
H13F H 0.3617 -0.0240 0.9675 0.095 Uiso 1 1 calc GR . . . .
C10B C 0.1571(7) 0.2045(5) 0.8630(4) 0.0506(15) Uani 1 1 d . . . . .
H10C H 0.1648 0.1846 0.9276 0.061 Uiso 1 1 calc R . . . .
H10D H 0.1675 0.2861 0.8360 0.061 Uiso 1 1 calc R . . . .
C14B C 0.4201(7) 0.1824(5) 0.8516(3) 0.0466(13) Uani 1 1 d . . . . .
H14C H 0.4323 0.2641 0.8269 0.056 Uiso 1 1 calc R . . . .
H14D H 0.4068 0.1609 0.9175 0.056 Uiso 1 1 calc R . . . .
C11A C 0.9255(6) 1.3454(5) 0.2656(4) 0.0502(14) Uani 1 1 d . . . . .
H11A H 0.9302 1.4266 0.2442 0.075 Uiso 1 1 calc GR . . . .
H11B H 1.0236 1.3153 0.2723 0.075 Uiso 1 1 calc GR . . . .
H11C H 0.8650 1.3189 0.3234 0.075 Uiso 1 1 calc GR . . . .
C15A C 0.5370(7) 1.3478(5) 0.0652(4) 0.0518(14) Uani 1 1 d . . . . .
H15A H 0.5584 1.4193 0.0177 0.078 Uiso 1 1 calc GR . . . .
H15B H 0.4618 1.3576 0.1104 0.078 Uiso 1 1 calc GR . . . .
H15C H 0.5025 1.2950 0.0398 0.078 Uiso 1 1 calc GR . . . .
C15B C 0.5560(7) 0.1311(5) 0.8247(4) 0.0581(16) Uani 1 1 d . . . . .
H15D H 0.5654 0.1449 0.7603 0.087 Uiso 1 1 calc GR . . . .
H15E H 0.5526 0.0509 0.8570 0.087 Uiso 1 1 calc GR . . . .
H15F H 0.6395 0.1636 0.8392 0.087 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.75542(15) 0.43684(12) 0.81804(9) 0.0458(4) Uani 1 1 d . . . . .
O5 O 0.8472(5) 0.4178(4) 0.7469(3) 0.0706(14) Uani 1 1 d . . . . .
O4 O 0.8276(7) 0.4098(6) 0.8920(3) 0.098(2) Uani 1 1 d . . . . .
O9 O -0.0326(6) -0.1576(5) 0.9228(3) 0.0794(15) Uani 1 1 d . . . . .
O2 O 0.7228(6) 0.5526(5) 0.7896(4) 0.0954(18) Uani 1 1 d . . . . .
O7 O -0.2833(7) -0.1252(6) 0.9170(4) 0.106(2) Uani 1 1 d . . . . .
C11B C 0.0086(8) 0.1732(6) 0.8526(5) 0.075(2) Uani 1 1 d . . . . .
H11D H -0.0026 0.1951 0.7890 0.113 Uiso 1 1 calc GR . . . .
H11E H -0.0641 0.2113 0.8815 0.113 Uiso 1 1 calc GR . . . .
H11F H -0.0049 0.0928 0.8806 0.113 Uiso 1 1 calc GR . . . .
O3 O 0.6229(7) 0.3848(6) 0.8324(5) 0.125(3) Uani 1 1 d . . . . .
O8 O -0.1657(7) -0.2207(6) 0.8355(6) 0.134(3) Uani 1 1 d . . . . .
O6 O -0.1172(12) -0.0389(9) 0.7984(6) 0.210(6) 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 O1B 1.906(3) . ?
Cu1 N1B 1.936(4) . ?
Cu1 O1A 1.891(3) . ?
Cu1 N1A 1.940(4) . ?
Cl2 O9 1.422(5) . ?
Cl2 O7 1.435(6) . ?
Cl2 O8 1.388(5) . ?
Cl2 O6 1.357(8) . ?
O1B C2B 1.322(5) . ?
N1B C7B 1.271(6) . ?
N1B C8B 1.456(6) . ?
N2A C9A 1.518(6) . ?
N2A C10A 1.499(6) . ?
N2A C12A 1.535(6) . ?
N2A C14A 1.518(6) . ?
O1A C2A 1.323(5) . ?
N1A C7A 1.282(6) . ?
N1A C8A 1.466(6) . ?
C2A C1A 1.433(7) . ?
C2A C3A 1.417(6) . ?
C6A C1A 1.410(6) . ?
C6A C5A 1.387(6) . ?
C1B C6B 1.413(6) . ?
C1B C7B 1.448(6) . ?
C1B C2B 1.416(6) . ?
C1A C7A 1.439(6) . ?
C6B C5B 1.367(7) . ?
C9A C5A 1.507(6) . ?
C4A C5A 1.403(6) . ?
C4A C3A 1.378(6) . ?
N2B C9B 1.527(6) . ?
N2B C12B 1.522(6) . ?
N2B C10B 1.518(7) . ?
N2B C14B 1.510(7) . ?
C2B C3B 1.402(6) . ?
C3B C4B 1.367(6) . ?
C9B C5B 1.519(6) . ?
C8B C8A 1.527(6) . ?
C5B C4B 1.392(7) . ?
C10A C11A 1.524(7) . ?
C12A C13A 1.520(8) . ?
C12B C13B 1.516(7) . ?
C14A C15A 1.505(8) . ?
C10B C11B 1.493(10) . ?
C14B C15B 1.486(9) . ?
Cl1 O5 1.421(4) . ?
Cl1 O4 1.369(5) . ?
Cl1 O2 1.428(6) . ?
Cl1 O3 1.376(6) . ?

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
O1B Cu1 N1B 93.81(14) . . ?
O1B Cu1 N1A 166.13(15) . . ?
N1B Cu1 N1A 84.48(16) . . ?
O1A Cu1 O1B 90.84(13) . . ?
O1A Cu1 N1B 166.16(14) . . ?
O1A Cu1 N1A 94.04(14) . . ?
O9 Cl2 O7 111.1(3) . . ?
O8 Cl2 O9 111.7(3) . . ?
O8 Cl2 O7 105.4(4) . . ?
O6 Cl2 O9 109.4(4) . . ?
O6 Cl2 O7 109.3(7) . . ?
O6 Cl2 O8 109.9(7) . . ?
C2B O1B Cu1 126.8(3) . . ?
C7B N1B Cu1 126.8(3) . . ?
C7B N1B C8B 121.0(4) . . ?
C8B N1B Cu1 112.1(3) . . ?
C9A N2A C12A 105.8(3) . . ?
C10A N2A C9A 110.3(4) . . ?
C10A N2A C12A 112.7(4) . . ?
C10A N2A C14A 105.8(4) . . ?
C14A N2A C9A 111.6(4) . . ?
C14A N2A C12A 110.8(4) . . ?
C2A O1A Cu1 127.0(3) . . ?
C7A N1A Cu1 126.3(3) . . ?
C7A N1A C8A 121.1(4) . . ?
C8A N1A Cu1 112.3(3) . . ?
O1A C2A C1A 124.3(4) . . ?
O1A C2A C3A 118.1(4) . . ?
C3A C2A C1A 117.6(4) . . ?
C5A C6A C1A 122.4(4) . . ?
C6B C1B C7B 116.8(4) . . ?
C6B C1B C2B 119.3(4) . . ?
C2B C1B C7B 123.9(4) . . ?
C2A C1A C7A 122.9(4) . . ?
C6A C1A C2A 119.1(4) . . ?
C6A C1A C7A 118.1(4) . . ?
C5B C6B C1B 122.7(4) . . ?
C5A C9A N2A 116.6(4) . . ?
C3A C4A C5A 121.7(4) . . ?
N1A C7A C1A 125.2(4) . . ?
N1B C7B C1B 124.4(4) . . ?
C12B N2B C9B 106.0(3) . . ?
C10B N2B C9B 110.0(4) . . ?
C10B N2B C12B 110.3(4) . . ?
C14B N2B C9B 111.5(4) . . ?
C14B N2B C12B 111.8(4) . . ?
C14B N2B C10B 107.2(4) . . ?
O1B C2B C1B 123.9(4) . . ?
O1B C2B C3B 119.5(4) . . ?
C3B C2B C1B 116.6(4) . . ?
C4B C3B C2B 122.4(4) . . ?
C6A C5A C9A 122.0(4) . . ?
C6A C5A C4A 117.9(4) . . ?
C4A C5A C9A 120.1(4) . . ?
C5B C9B N2B 115.7(4) . . ?
N1B C8B C8A 107.9(4) . . ?
C6B C5B C9B 120.6(4) . . ?
C6B C5B C4B 117.3(4) . . ?
C4B C5B C9B 121.9(4) . . ?
C4A C3A C2A 121.3(4) . . ?
N1A C8A C8B 106.3(4) . . ?
N2A C10A C11A 116.0(4) . . ?
C3B C4B C5B 121.6(4) . . ?
C13A C12A N2A 114.4(4) . . ?
C13B C12B N2B 114.8(4) . . ?
C15A C14A N2A 116.5(4) . . ?
C11B C10B N2B 116.5(5) . . ?
C15B C14B N2B 115.6(5) . . ?
O5 Cl1 O2 107.0(3) . . ?
O4 Cl1 O5 109.5(3) . . ?
O4 Cl1 O2 109.3(4) . . ?
O4 Cl1 O3 114.4(5) . . ?
O3 Cl1 O5 111.6(4) . . ?
O3 Cl1 O2 104.7(4) . . ?

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
Cu1 O1B C2B C1B -3.8(6) . . . . ?
Cu1 O1B C2B C3B 175.2(3) . . . . ?
Cu1 N1B C7B C1B -7.7(6) . . . . ?
Cu1 N1B C8B C8A 34.4(4) . . . . ?
Cu1 O1A C2A C1A -2.4(6) . . . . ?
Cu1 O1A C2A C3A 176.4(3) . . . . ?
Cu1 N1A C7A C1A -5.6(7) . . . . ?
Cu1 N1A C8A C8B 35.1(4) . . . . ?
O1B Cu1 O1A C2A 166.1(4) . . . . ?
O1B C2B C3B C4B -178.9(4) . . . . ?
N1B Cu1 O1A C2A -84.2(7) . . . . ?
N1B C8B C8A N1A -44.1(5) . . . . ?
N2A C9A C5A C6A 87.4(5) . . . . ?
N2A C9A C5A C4A -95.2(5) . . . . ?
O1A C2A C1A C6A -177.6(4) . . . . ?
O1A C2A C1A C7A 2.9(7) . . . . ?
O1A C2A C3A C4A 178.5(4) . . . . ?
N1A Cu1 O1A C2A -0.9(4) . . . . ?
C2A C1A C7A N1A 1.3(7) . . . . ?
C6A C1A C7A N1A -178.1(4) . . . . ?
C1B C6B C5B C9B 178.5(4) . . . . ?
C1B C6B C5B C4B 2.2(7) . . . . ?
C1B C2B C3B C4B 0.1(6) . . . . ?
C1A C2A C3A C4A -2.6(7) . . . . ?
C1A C6A C5A C9A 177.6(4) . . . . ?
C1A C6A C5A C4A 0.1(7) . . . . ?
C6B C1B C7B N1B -176.4(4) . . . . ?
C6B C1B C2B O1B -177.6(4) . . . . ?
C6B C1B C2B C3B 3.4(6) . . . . ?
C6B C5B C4B C3B 1.5(7) . . . . ?
C9A N2A C10A C11A -60.4(6) . . . . ?
C9A N2A C12A C13A 176.2(5) . . . . ?
C9A N2A C14A C15A 67.8(5) . . . . ?
C7A N1A C8A C8B -149.5(4) . . . . ?
C7B N1B C8B C8A -150.1(4) . . . . ?
C7B C1B C6B C5B 173.7(4) . . . . ?
C7B C1B C2B O1B 4.1(7) . . . . ?
C7B C1B C2B C3B -174.9(4) . . . . ?
N2B C9B C5B C6B 84.6(6) . . . . ?
N2B C9B C5B C4B -99.3(5) . . . . ?
C2B C1B C6B C5B -4.7(6) . . . . ?
C2B C1B C7B N1B 2.0(7) . . . . ?
C2B C3B C4B C5B -2.7(7) . . . . ?
C5A C6A C1A C2A -2.4(7) . . . . ?
C5A C6A C1A C7A 177.1(4) . . . . ?
C5A C4A C3A C2A 0.4(7) . . . . ?
C9B N2B C12B C13B 175.4(5) . . . . ?
C9B N2B C10B C11B 66.2(6) . . . . ?
C9B N2B C14B C15B -64.4(6) . . . . ?
C9B C5B C4B C3B -174.7(4) . . . . ?
C8B N1B C7B C1B 177.6(4) . . . . ?
C3A C2A C1A C6A 3.6(6) . . . . ?
C3A C2A C1A C7A -175.9(4) . . . . ?
C3A C4A C5A C6A 0.9(7) . . . . ?
C3A C4A C5A C9A -176.6(4) . . . . ?
C8A N1A C7A C1A 179.7(4) . . . . ?
C10A N2A C9A C5A -66.7(5) . . . . ?
C10A N2A C12A C13A 55.6(6) . . . . ?
C10A N2A C14A C15A -172.2(4) . . . . ?
C12A N2A C9A C5A 171.1(4) . . . . ?
C12A N2A C10A C11A 57.6(6) . . . . ?
C12A N2A C14A C15A -49.7(6) . . . . ?
C12B N2B C9B C5B 179.5(4) . . . . ?
C12B N2B C10B C11B -50.4(6) . . . . ?
C12B N2B C14B C15B 54.1(6) . . . . ?
C14A N2A C9A C5A 50.6(5) . . . . ?
C14A N2A C10A C11A 178.8(4) . . . . ?
C14A N2A C12A C13A -62.8(6) . . . . ?
C10B N2B C9B C5B 60.2(5) . . . . ?
C10B N2B C12B C13B -65.5(7) . . . . ?
C10B N2B C14B C15B 175.2(4) . . . . ?
C14B N2B C9B C5B -58.6(6) . . . . ?
C14B N2B C12B C13B 53.7(7) . . . . ?
C14B N2B C10B C11B -172.4(5) . . . . ?


####################################################################### 
# 
# 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_tr
_database_code_depnum_ccdc_archive 'CCDC 1451696'
_audit_update_record             
;
2016-03-23 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_tr                  
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.721 Note
RESPONSE: Completeness to low but supporting chemical facts forwarded the upload. A very small number of measureable crytsals and a not properly working cooling system made the total measurement of the substance impossible.
;
_vrf_PLAT340_tr                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01542 Ang.
RESPONSE: Completeness to low but supporting chemical facts forwarded the upload. A very small number of measureable crytsals and a not properly working cooling system made the total measurement of the substance impossible.
;
_vrf_PLAT911_tr                  
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.600       1202 Report
RESPONSE: Completeness to low but supporting chemical facts forwarded the upload. A very small number of measureable crytsals and a not properly working cooling system made the total measurement of the substance impossible.
;
# Added during the CSD deposition process: Wednesday 23 March 2016 08:58 AM
# end Validation Reply Form

_audit_creation_date             2016-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
[N,N'-bis(5-triethylammoniummethylsalicylidene)-1,2-ethylenediamine](ClO4)2 
;
_chemical_formula_moiety         '2(Cl O4), C30 H48 N4 O2'
_chemical_formula_sum            'C30 H48 Cl2 N4 O10'
_chemical_formula_weight         695.62
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.779(6)
_cell_length_b                   8.339(6)
_cell_length_c                   14.025(12)
_cell_angle_alpha                75.82(2)
_cell_angle_beta                 81.71(2)
_cell_angle_gamma                80.21(4)
_cell_volume                     864.2(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    258
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      22.193
_cell_measurement_theta_min      2.549
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.745987
_exptl_absorpt_correction_T_min  0.530345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0843 before and 0.0242 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0708 before and 0.0192 after correction.
 The Ratio of minimum to maximum transmission is 0.71.
 The λ/2 correction factor is Not present

HKLF 5 dataset constructed from all observations involving domain 1
    4830 Corrected reflections written to file Trn_L1_T5.hkl
 Reflections merged according to point-group -1    
 Single reflections that also occur in composites omitted
 Minimum and maximum apparent transmission:  0.530345  0.745987
 Additional spherical absorption correction applied with mu*r =  0.2000
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1570
_diffrn_reflns_Laue_measured_fraction_full 0.721
_diffrn_reflns_Laue_measured_fraction_max 0.718
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1942
_diffrn_reflns_point_group_measured_fraction_full 0.721
_diffrn_reflns_point_group_measured_fraction_max 0.718
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.544
_diffrn_ambient_temperature      130.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.721
_diffrn_measured_fraction_theta_max 0.718
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1099
_reflns_number_total             1942
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.209
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1942
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0928
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1269P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2098
_refine_ls_wR_factor_ref         0.2268
_refine_special_details          
;
 Refined as a 2-component perfect twin.
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C10 ∼ C11: within 1.6A with sigma of 0.01 and sigma for terminal atoms of
0.02
C5 ∼ C6 ∼ C4 ∼ C9: within 1.6A with sigma of 0.015 and sigma for
terminal atoms of 0.03
C12 ∼ C13: within 1.6A with sigma of 0.008 and sigma for terminal atoms of
0.016
Uanis(C14) = Uanis(C12) = Uanis(C10)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C10(H10A,H10B), C12(H12A,H12B), C9(H9A,H9B), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.7150(4) 0.1432(4) 0.1940(2) 0.0279(8) Uani 1 1 d . . . . .
O4 O 0.8597(8) 0.0746(9) 0.2527(7) 0.038(2) Uani 1 1 d . . . . .
N1 N 0.8476(11) 0.2019(12) 0.4856(7) 0.028(2) Uani 1 1 d . . . . .
O1 O 0.8730(9) 0.5198(9) 0.4415(6) 0.033(2) Uani 1 1 d . . . . .
H1 H 0.8975 0.4173 0.4661 0.050 Uiso 1 1 calc GR . . . .
N2 N 0.2035(10) 0.6416(11) 0.1867(7) 0.0214(19) Uani 1 1 d . . . . .
O3 O 0.7289(10) 0.3146(10) 0.1485(6) 0.048(3) Uani 1 1 d . . . . .
O5 O 0.7214(10) 0.0449(10) 0.1232(7) 0.045(2) Uani 1 1 d . . . . .
C14 C 0.3187(13) 0.7541(14) 0.1139(8) 0.0305(17) Uani 1 1 d . . . . .
H14A H 0.4407 0.7209 0.1311 0.037 Uiso 1 1 calc R . . . .
H14B H 0.3171 0.7343 0.0472 0.037 Uiso 1 1 calc R . . . .
C10 C 0.2600(13) 0.4663(14) 0.1727(8) 0.0305(17) Uani 1 1 d . U . . .
H10A H 0.3817 0.4302 0.1901 0.037 Uiso 1 1 calc R . . . .
H10B H 0.2618 0.4683 0.1017 0.037 Uiso 1 1 calc R . . . .
C12 C 0.0064(12) 0.6985(14) 0.1685(8) 0.0305(17) Uani 1 1 d . U . . .
H12A H -0.0664 0.6298 0.2214 0.037 Uiso 1 1 calc R . . . .
H12B H -0.0257 0.8159 0.1745 0.037 Uiso 1 1 calc R . . . .
C3 C 0.6464(13) 0.7114(15) 0.3613(9) 0.029(3) Uani 1 1 d . . . . .
H3 H 0.7091 0.8015 0.3576 0.035 Uiso 1 1 calc R . . . .
C9 C 0.2149(13) 0.6527(13) 0.2917(8) 0.023(3) Uani 1 1 d . U . . .
H9A H 0.1663 0.7675 0.2984 0.027 Uiso 1 1 calc R . . . .
H9B H 0.1392 0.5760 0.3369 0.027 Uiso 1 1 calc R . . . .
O2 O 0.5508(8) 0.1333(8) 0.2574(6) 0.038(2) Uani 1 1 d . . . . .
C1 C 0.6286(13) 0.4118(13) 0.4051(8) 0.020(3) Uani 1 1 d . . . . .
C4 C 0.4877(12) 0.7419(13) 0.3255(8) 0.022(3) Uani 1 1 d . U . . .
H4 H 0.4385 0.8541 0.3002 0.026 Uiso 1 1 calc R . . . .
C11 C 0.1476(13) 0.3364(13) 0.2322(10) 0.038(3) Uani 1 1 d . U . . .
H11A H 0.1391 0.3367 0.3025 0.057 Uiso 1 1 calc GR . . . .
H11B H 0.2011 0.2258 0.2222 0.057 Uiso 1 1 calc GR . . . .
H11C H 0.0299 0.3629 0.2102 0.057 Uiso 1 1 calc GR . . . .
C2 C 0.7176(11) 0.5487(14) 0.4033(8) 0.020(3) Uani 1 1 d . . . . .
C6 C 0.4658(12) 0.4504(13) 0.3679(8) 0.022(3) Uani 1 1 d . U . . .
H6 H 0.4007 0.3619 0.3720 0.026 Uiso 1 1 calc R . . . .
C7 C 0.7014(14) 0.2408(14) 0.4455(8) 0.027(3) Uani 1 1 d . . . . .
H7 H 0.6396 0.1535 0.4426 0.033 Uiso 1 1 calc R . . . .
C13 C -0.0389(15) 0.6863(16) 0.0708(9) 0.043(3) Uani 1 1 d . U . . .
H13A H -0.1562 0.7474 0.0598 0.064 Uiso 1 1 calc GR . . . .
H13B H -0.0373 0.5686 0.0705 0.064 Uiso 1 1 calc GR . . . .
H13C H 0.0472 0.7348 0.0181 0.064 Uiso 1 1 calc GR . . . .
C15 C 0.2700(16) 0.9371(14) 0.1085(9) 0.043(4) Uani 1 1 d . . . . .
H15A H 0.2514 0.9570 0.1755 0.064 Uiso 1 1 calc GR . . . .
H15B H 0.1618 0.9776 0.0766 0.064 Uiso 1 1 calc GR . . . .
H15C H 0.3648 0.9966 0.0699 0.064 Uiso 1 1 calc GR . . . .
C5 C 0.3947(12) 0.6120(13) 0.3251(8) 0.019(2) Uani 1 1 d . U . . .
C8 C 0.9106(13) 0.0263(15) 0.5248(8) 0.030(3) Uani 1 1 d . . . . .
H8A H 0.8266 -0.0433 0.5148 0.035 Uiso 1 1 calc R . . . .
H8B H 0.9167 0.0074 0.5968 0.035 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 O4 1.445(8) . ?
Cl1 O3 1.431(8) . ?
Cl1 O5 1.425(8) . ?
Cl1 O2 1.450(8) . ?
N1 C7 1.298(14) . ?
N1 C8 1.458(15) . ?
O1 C2 1.353(11) . ?
N2 C14 1.510(12) . ?
N2 C10 1.505(13) . ?
N2 C12 1.565(12) . ?
N2 C9 1.514(12) . ?
C14 C15 1.495(14) . ?
C10 C11 1.518(14) . ?
C12 C13 1.493(15) . ?
C3 C4 1.360(13) . ?
C3 C2 1.394(15) . ?
C9 C5 1.497(13) . ?
C1 C2 1.425(11) . ?
C1 C6 1.396(13) . ?
C1 C7 1.449(15) . ?
C4 C5 1.403(11) . ?
C6 C5 1.388(14) . ?
C8 C8 1.51(2) 2_756 ?

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
O4 Cl1 O2 109.5(5) . . ?
O3 Cl1 O4 109.0(5) . . ?
O3 Cl1 O2 109.1(4) . . ?
O5 Cl1 O4 108.0(5) . . ?
O5 Cl1 O3 112.3(6) . . ?
O5 Cl1 O2 108.9(5) . . ?
C7 N1 C8 119.0(8) . . ?
C14 N2 C12 110.4(8) . . ?
C14 N2 C9 111.0(7) . . ?
C10 N2 C14 107.9(8) . . ?
C10 N2 C12 110.0(7) . . ?
C10 N2 C9 111.7(8) . . ?
C9 N2 C12 105.9(8) . . ?
C15 C14 N2 116.0(9) . . ?
N2 C10 C11 116.0(9) . . ?
C13 C12 N2 115.4(10) . . ?
C4 C3 C2 120.3(9) . . ?
C5 C9 N2 116.0(9) . . ?
C2 C1 C7 121.7(9) . . ?
C6 C1 C2 116.9(9) . . ?
C6 C1 C7 121.4(8) . . ?
C3 C4 C5 121.7(10) . . ?
O1 C2 C3 120.0(9) . . ?
O1 C2 C1 119.7(10) . . ?
C3 C2 C1 120.3(8) . . ?
C5 C6 C1 123.1(8) . . ?
N1 C7 C1 122.7(9) . . ?
C4 C5 C9 119.6(9) . . ?
C6 C5 C9 122.4(8) . . ?
C6 C5 C4 117.5(9) . . ?
N1 C8 C8 111.6(11) . 2_756 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C9 C5 C4 99.9(11) . . . . ?
N2 C9 C5 C6 -88.4(12) . . . . ?
C14 N2 C10 C11 -174.0(9) . . . . ?
C14 N2 C12 C13 63.9(12) . . . . ?
C14 N2 C9 C5 -57.2(12) . . . . ?
C10 N2 C14 C15 173.5(9) . . . . ?
C10 N2 C12 C13 -55.1(12) . . . . ?
C10 N2 C9 C5 63.2(10) . . . . ?
C12 N2 C14 C15 53.2(11) . . . . ?
C12 N2 C10 C11 -53.4(11) . . . . ?
C12 N2 C9 C5 -177.1(8) . . . . ?
C3 C4 C5 C9 175.7(11) . . . . ?
C3 C4 C5 C6 3.6(16) . . . . ?
C9 N2 C14 C15 -63.9(12) . . . . ?
C9 N2 C10 C11 63.9(10) . . . . ?
C9 N2 C12 C13 -175.9(9) . . . . ?
C1 C6 C5 C9 -175.9(10) . . . . ?
C1 C6 C5 C4 -4.0(16) . . . . ?
C4 C3 C2 O1 -178.0(10) . . . . ?
C4 C3 C2 C1 2.9(17) . . . . ?
C2 C3 C4 C5 -3.1(17) . . . . ?
C2 C1 C6 C5 3.9(16) . . . . ?
C2 C1 C7 N1 2.6(16) . . . . ?
C6 C1 C2 O1 177.7(10) . . . . ?
C6 C1 C2 C3 -3.2(15) . . . . ?
C6 C1 C7 N1 -176.0(11) . . . . ?
C7 N1 C8 C8 120.8(12) . . . 2_756 ?
C7 C1 C2 O1 -1.0(15) . . . . ?
C7 C1 C2 C3 178.1(11) . . . . ?
C7 C1 C6 C5 -177.5(11) . . . . ?
C8 N1 C7 C1 179.7(10) . . . . ?

