# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_al063_0m
_database_code_depnum_ccdc_archive 'CCDC 1038475'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;
_audit_creation_date             2014-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36 H38 Cl2 Cu2 N6, 2(C H2 Cl2)'
_chemical_formula_sum            'C38 H42 Cl6 Cu2 N6'
_chemical_formula_weight         922.55
_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'

_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                   8.2153(8)
_cell_length_b                   11.1662(10)
_cell_length_c                   11.5343(11)
_cell_angle_alpha                85.272(3)
_cell_angle_beta                 84.430(3)
_cell_angle_gamma                77.543(3)
_cell_volume                     1026.24(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5572
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.660
_shelx_estimated_absorpt_T_min   0.502
_exptl_absorpt_coefficient_mu    1.463
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0564 before and 0.0340 after correction.
The Ratio of minimum to maximum transmission is 0.8587.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.546
_exptl_crystal_size_mid          0.431
_exptl_crystal_size_min          0.31
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13923
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.787
_diffrn_reflns_theta_min         1.777
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3628
_reflns_number_total             4388
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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., 2013)'
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.161
_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)+(0.0647P)²+0.1746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1175
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
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
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C17(H17), C15(H15), C6(H6), C18(H18), C16(H16), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_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
Cu1 Cu 0.46333(4) 0.47832(3) 0.39387(3) 0.03966(13) Uani 1 1 d . . . . .
Cl1 Cl 0.24486(8) 0.57992(6) 0.27955(6) 0.04572(18) Uani 1 1 d . . . . .
Cl3 Cl 0.35869(14) 0.89636(11) 0.10519(9) 0.0908(3) Uani 1 1 d . . . . .
Cl2 Cl 0.67518(16) 0.73838(13) 0.04920(12) 0.1169(5) Uani 1 1 d . . . . .
N1 N 0.4191(2) 0.24364(17) 0.50872(16) 0.0319(4) Uani 1 1 d . . . . .
N3 N 0.3509(2) 0.54943(17) 0.73870(17) 0.0328(4) Uani 1 1 d . . . . .
N2 N 0.2390(2) 0.38892(16) 0.58526(15) 0.0284(4) Uani 1 1 d . . . . .
C2 C 0.3039(3) 0.1896(2) 0.5778(2) 0.0396(6) Uani 1 1 d . . . . .
H2 H 0.3044 0.1061 0.5886 0.048 Uiso 1 1 calc R . . . .
C9 C 0.7098(3) 0.1479(2) 0.4487(2) 0.0379(5) Uani 1 1 d . . . . .
C8 C 0.8251(3) 0.0990(2) 0.3605(3) 0.0457(6) Uani 1 1 d . . . . .
H8 H 0.9378 0.0784 0.3743 0.055 Uiso 1 1 calc R . . . .
C14 C 0.1902(3) 0.5459(2) 0.73025(19) 0.0301(5) Uani 1 1 d . . . . .
C7 C 0.7793(4) 0.0795(3) 0.2529(3) 0.0504(7) Uani 1 1 d . . . . .
C1 C 0.3797(3) 0.3684(2) 0.5117(2) 0.0303(5) Uani 1 1 d . . . . .
C10 C 0.3100(4) 0.2002(3) 0.2912(3) 0.0603(8) Uani 1 1 d . . . . .
H10A H 0.2756 0.2880 0.2905 0.090 Uiso 1 1 calc GR . . . .
H10B H 0.2421 0.1634 0.3502 0.090 Uiso 1 1 calc GR . . . .
H10C H 0.2969 0.1733 0.2164 0.090 Uiso 1 1 calc GR . . . .
C17 C 0.2775(4) 0.6103(3) 0.9336(2) 0.0505(7) Uani 1 1 d . . . . .
H17 H 0.3107 0.6323 1.0023 0.061 Uiso 1 1 calc R . . . .
C15 C 0.0687(3) 0.5742(2) 0.8206(2) 0.0417(6) Uani 1 1 d . . . . .
H15 H -0.0417 0.5712 0.8119 0.050 Uiso 1 1 calc R . . . .
C5 C 0.4900(3) 0.1623(2) 0.3172(2) 0.0413(6) Uani 1 1 d . . . . .
C6 C 0.6109(4) 0.1104(3) 0.2329(2) 0.0516(7) Uani 1 1 d . . . . .
H6 H 0.5784 0.0960 0.1612 0.062 Uiso 1 1 calc R . . . .
C4 C 0.5426(3) 0.1820(2) 0.4242(2) 0.0334(5) Uani 1 1 d . . . . .
C18 C 0.3918(3) 0.5807(2) 0.8403(2) 0.0436(6) Uani 1 1 d . . . . .
H18 H 0.5030 0.5823 0.8477 0.052 Uiso 1 1 calc R . . . .
C16 C 0.1128(4) 0.6072(3) 0.9242(2) 0.0497(7) Uani 1 1 d . . . . .
H16 H 0.0329 0.6268 0.9863 0.060 Uiso 1 1 calc R . . . .
C19 C 0.5133(4) 0.7789(3) 0.1546(3) 0.0697(9) Uani 1 1 d . . . . .
H19A H 0.4657 0.7078 0.1796 0.084 Uiso 1 1 calc R . . . .
H19B H 0.5568 0.8042 0.2218 0.084 Uiso 1 1 calc R . . . .
C12 C 0.7632(4) 0.1605(3) 0.5672(3) 0.0601(8) Uani 1 1 d . . . . .
H12A H 0.7189 0.1048 0.6231 0.090 Uiso 1 1 calc GR . . . .
H12B H 0.7218 0.2432 0.5894 0.090 Uiso 1 1 calc GR . . . .
H12C H 0.8831 0.1415 0.5648 0.090 Uiso 1 1 calc GR . . . .
C11 C 0.9096(5) 0.0272(4) 0.1583(3) 0.0851(12) Uani 1 1 d . . . . .
H11A H 0.9176 0.0894 0.0966 0.128 Uiso 1 1 calc GR . . . .
H11B H 0.8781 -0.0412 0.1279 0.128 Uiso 1 1 calc GR . . . .
H11C H 1.0160 0.0003 0.1903 0.128 Uiso 1 1 calc GR . . . .
C13 C 0.1470(3) 0.5114(2) 0.6151(2) 0.0325(5) Uani 1 1 d . . . . .
H13A H 0.0279 0.5137 0.6188 0.039 Uiso 1 1 calc R . . . .
H13B H 0.1724 0.5714 0.5541 0.039 Uiso 1 1 calc R . . . .
C3 C 0.1911(3) 0.2815(2) 0.6263(2) 0.0387(5) Uani 1 1 d . . . . .
H3 H 0.0988 0.2738 0.6775 0.046 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
Cu1 Cu1 2.6832(7) 2_666 ?
Cu1 Cl1 2.3625(7) . ?
Cu1 N3 2.0454(19) 2_666 ?
Cu1 C1 1.932(2) . ?
Cl3 C19 1.720(4) . ?
Cl2 C19 1.723(4) . ?
N1 C2 1.384(3) . ?
N1 C1 1.363(3) . ?
N1 C4 1.439(3) . ?
N3 Cu1 2.0453(19) 2_666 ?
N3 C14 1.343(3) . ?
N3 C18 1.342(3) . ?
N2 C1 1.356(3) . ?
N2 C13 1.464(3) . ?
N2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.344(4) . ?
C9 C8 1.383(4) . ?
C9 C4 1.394(3) . ?
C9 C12 1.501(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.379(4) . ?
C14 C15 1.378(3) . ?
C14 C13 1.508(3) . ?
C7 C6 1.388(4) . ?
C7 C11 1.512(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 C5 1.501(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(4) . ?
C17 C16 1.375(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(4) . ?
C5 C6 1.387(4) . ?
C5 C4 1.396(4) . ?
C6 H6 0.9300 . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C3 H3 0.9300 . ?

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
Cl1 Cu1 Cu1 130.63(2) . 2_666 ?
N3 Cu1 Cu1 119.54(6) 2_666 2_666 ?
N3 Cu1 Cl1 97.36(6) 2_666 . ?
C1 Cu1 Cu1 69.57(7) . 2_666 ?
C1 Cu1 Cl1 109.62(7) . . ?
C1 Cu1 N3 132.70(9) . 2_666 ?
C2 N1 C4 125.00(19) . . ?
C1 N1 C2 111.40(19) . . ?
C1 N1 C4 122.26(19) . . ?
C14 N3 Cu1 125.36(15) . 2_666 ?
C18 N3 Cu1 116.99(16) . 2_666 ?
C18 N3 C14 117.5(2) . . ?
C1 N2 C13 123.78(18) . . ?
C1 N2 C3 112.06(18) . . ?
C3 N2 C13 124.15(19) . . ?
N1 C2 H2 126.7 . . ?
C3 C2 N1 106.6(2) . . ?
C3 C2 H2 126.7 . . ?
C8 C9 C4 117.6(2) . . ?
C8 C9 C12 120.9(2) . . ?
C4 C9 C12 121.6(2) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 C9 122.4(3) . . ?
C7 C8 H8 118.8 . . ?
N3 C14 C15 122.4(2) . . ?
N3 C14 C13 116.63(19) . . ?
C15 C14 C13 120.9(2) . . ?
C8 C7 C6 118.5(2) . . ?
C8 C7 C11 120.7(3) . . ?
C6 C7 C11 120.8(3) . . ?
N1 C1 Cu1 123.56(16) . . ?
N2 C1 Cu1 129.58(16) . . ?
N2 C1 N1 103.34(18) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
C18 C17 H17 120.5 . . ?
C18 C17 C16 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C6 C5 C10 120.5(3) . . ?
C6 C5 C4 117.8(2) . . ?
C4 C5 C10 121.6(2) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6 119.2 . . ?
C9 C4 N1 120.1(2) . . ?
C9 C4 C5 122.0(2) . . ?
C5 C4 N1 117.9(2) . . ?
N3 C18 C17 123.2(2) . . ?
N3 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
Cl3 C19 Cl2 112.29(19) . . ?
Cl3 C19 H19A 109.1 . . ?
Cl3 C19 H19B 109.1 . . ?
Cl2 C19 H19A 109.1 . . ?
Cl2 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C13 C14 112.13(18) . . ?
N2 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N2 C3 H3 126.7 . . ?
C2 C3 N2 106.6(2) . . ?
C2 C3 H3 126.7 . . ?

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 N3 C14 C15 -175.14(18) 2_666 . . . ?
Cu1 N3 C14 C13 3.7(3) 2_666 . . . ?
Cu1 N3 C18 C17 175.3(2) 2_666 . . . ?
N1 C2 C3 N2 0.4(3) . . . . ?
N3 C14 C15 C16 -0.3(4) . . . . ?
N3 C14 C13 N2 60.1(3) . . . . ?
C2 N1 C1 Cu1 -159.90(18) . . . . ?
C2 N1 C1 N2 0.7(3) . . . . ?
C2 N1 C4 C9 -104.8(3) . . . . ?
C2 N1 C4 C5 77.5(3) . . . . ?
C9 C8 C7 C6 0.0(4) . . . . ?
C9 C8 C7 C11 179.2(3) . . . . ?
C8 C9 C4 N1 -174.3(2) . . . . ?
C8 C9 C4 C5 3.2(4) . . . . ?
C8 C7 C6 C5 1.4(4) . . . . ?
C14 N3 C18 C17 -1.0(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C1 N1 C2 C3 -0.7(3) . . . . ?
C1 N1 C4 C9 89.6(3) . . . . ?
C1 N1 C4 C5 -88.1(3) . . . . ?
C1 N2 C13 C14 -98.4(2) . . . . ?
C1 N2 C3 C2 0.0(3) . . . . ?
C10 C5 C6 C7 177.2(3) . . . . ?
C10 C5 C4 N1 -1.9(4) . . . . ?
C10 C5 C4 C9 -179.5(3) . . . . ?
C15 C14 C13 N2 -121.0(2) . . . . ?
C6 C5 C4 N1 175.7(2) . . . . ?
C6 C5 C4 C9 -1.9(4) . . . . ?
C4 N1 C2 C3 -167.7(2) . . . . ?
C4 N1 C1 Cu1 7.5(3) . . . . ?
C4 N1 C1 N2 168.0(2) . . . . ?
C4 C9 C8 C7 -2.3(4) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C18 N3 C14 C15 0.8(3) . . . . ?
C18 N3 C14 C13 179.6(2) . . . . ?
C18 C17 C16 C15 -0.1(5) . . . . ?
C16 C17 C18 N3 0.6(5) . . . . ?
C12 C9 C8 C7 176.2(3) . . . . ?
C12 C9 C4 N1 7.2(4) . . . . ?
C12 C9 C4 C5 -175.2(3) . . . . ?
C11 C7 C6 C5 -177.8(3) . . . . ?
C13 N2 C1 Cu1 -20.1(3) . . . . ?
C13 N2 C1 N1 -179.03(19) . . . . ?
C13 N2 C3 C2 178.6(2) . . . . ?
C13 C14 C15 C16 -179.0(2) . . . . ?
C3 N2 C1 Cu1 158.52(19) . . . . ?
C3 N2 C1 N1 -0.4(2) . . . . ?
C3 N2 C13 C14 83.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_al065_0m
_database_code_depnum_ccdc_archive 'CCDC 1038476'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;
_audit_creation_date             2014-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36 H38 Cl2 Cu2 N6, 2(C H2 Cl2)'
_chemical_formula_sum            'C38 H42 Cl6 Cu2 N6'
_chemical_formula_weight         922.55
_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'

_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                   8.1887(6)
_cell_length_b                   10.9691(7)
_cell_length_c                   11.3579(8)
_cell_angle_alpha                85.0163(15)
_cell_angle_beta                 85.1738(16)
_cell_angle_gamma                77.5551(15)
_cell_volume                     990.21(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7618
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.794
_shelx_estimated_absorpt_T_min   0.628
_exptl_absorpt_coefficient_mu    1.516
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0750 before and 0.0293 after correction.
The Ratio of minimum to maximum transmission is 0.8441.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11434
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.745
_diffrn_reflns_theta_min         1.804
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3934
_reflns_number_total             4210
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.040
_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)+(0.0289P)²+0.6356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0618
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C18(H18), C15(H15), C17(H17), C8(H8), C16(H16)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.46616(2) 0.98141(2) 0.89570(2) 0.01438(6) Uani 1 1 d . . . . .
Cl1 Cl 0.24195(4) 1.07728(3) 0.77779(3) 0.01601(9) Uani 1 1 d . . . . .
Cl2 Cl 0.64494(6) 0.59814(4) 1.39648(4) 0.02923(11) Uani 1 1 d . . . . .
Cl3 Cl 0.32310(6) 0.76514(5) 1.44785(5) 0.03570(12) Uani 1 1 d . . . . .
N1 N 0.41803(15) 0.74202(12) 1.01085(11) 0.0118(2) Uani 1 1 d . . . . .
N2 N 0.23630(15) 0.89003(11) 1.08606(11) 0.0108(2) Uani 1 1 d . . . . .
C13 C 0.14431(18) 1.01487(14) 1.11648(13) 0.0124(3) Uani 1 1 d . . . . .
H13A H 0.0225 1.0171 1.1208 0.015 Uiso 1 1 calc R . . . .
H13B H 0.1685 1.0776 1.0531 0.015 Uiso 1 1 calc R . . . .
C9 C 0.71038(19) 0.64701(14) 0.95086(14) 0.0148(3) Uani 1 1 d . . . . .
C1 C 0.38001(18) 0.86940(14) 1.01556(13) 0.0124(3) Uani 1 1 d . . . . .
C2 C 0.29809(19) 0.68662(14) 1.07581(13) 0.0143(3) Uani 1 1 d . . . . .
H2 H 0.2967 0.5999 1.0846 0.017 Uiso 1 1 calc R . . . .
C3 C 0.18422(19) 0.78003(14) 1.12390(13) 0.0139(3) Uani 1 1 d . . . . .
H3 H 0.0875 0.7721 1.1738 0.017 Uiso 1 1 calc R . . . .
C6 C 0.6088(2) 0.60826(15) 0.73075(14) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.5741 0.5916 0.6571 0.023 Uiso 1 1 calc R . . . .
C14 C 0.19096(18) 1.04925(13) 1.23313(13) 0.0115(3) Uani 1 1 d . . . . .
C4 C 0.54194(19) 0.68038(13) 0.92525(13) 0.0127(3) Uani 1 1 d . . . . .
C18 C 0.39879(19) 1.08286(14) 1.34369(14) 0.0156(3) Uani 1 1 d . . . . .
H18 H 0.5133 1.0842 1.3504 0.019 Uiso 1 1 calc R . . . .
C15 C 0.07136(19) 1.07749(14) 1.32612(14) 0.0152(3) Uani 1 1 d . . . . .
H15 H -0.0422 1.0744 1.3180 0.018 Uiso 1 1 calc R . . . .
C17 C 0.2866(2) 1.11330(15) 1.43978(14) 0.0182(3) Uani 1 1 d . . . . .
H17 H 0.3233 1.1358 1.5104 0.022 Uiso 1 1 calc R . . . .
C8 C 0.82653(19) 0.59914(14) 0.86081(15) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.9422 0.5794 0.8752 0.021 Uiso 1 1 calc R . . . .
C5 C 0.4882(2) 0.66100(14) 0.81628(14) 0.0156(3) Uani 1 1 d . . . . .
C12 C 0.7648(2) 0.65864(16) 1.07169(16) 0.0218(3) Uani 1 1 d . . . . .
H12A H 0.7166 0.7428 1.0969 0.033 Uiso 1 1 calc GR . . . .
H12B H 0.8874 0.6442 1.0688 0.033 Uiso 1 1 calc GR . . . .
H12C H 0.7260 0.5965 1.1282 0.033 Uiso 1 1 calc GR . . . .
C7 C 0.7788(2) 0.57936(15) 0.75065(15) 0.0189(3) Uani 1 1 d . . . . .
C10 C 0.3065(2) 0.70029(17) 0.78931(15) 0.0213(3) Uani 1 1 d . . . . .
H10A H 0.2688 0.7906 0.7959 0.032 Uiso 1 1 calc GR . . . .
H10B H 0.2389 0.6557 0.8458 0.032 Uiso 1 1 calc GR . . . .
H10C H 0.2936 0.6801 0.7087 0.032 Uiso 1 1 calc GR . . . .
C19 C 0.4862(2) 0.71831(17) 1.33916(15) 0.0229(4) Uani 1 1 d . . . . .
H19A H 0.4401 0.6885 1.2718 0.027 Uiso 1 1 calc R . . . .
H19B H 0.5349 0.7911 1.3092 0.027 Uiso 1 1 calc R . . . .
C11 C 0.9080(2) 0.52636(19) 0.65536(17) 0.0305(4) Uani 1 1 d . . . . .
H11A H 0.8611 0.4729 0.6086 0.046 Uiso 1 1 calc GR . . . .
H11B H 1.0075 0.4768 0.6921 0.046 Uiso 1 1 calc GR . . . .
H11C H 0.9394 0.5950 0.6036 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.1197(2) 1.11043(15) 1.43146(14) 0.0177(3) Uani 1 1 d . . . . .
H16 H 0.0399 1.1305 1.4963 0.021 Uiso 1 1 calc R . . . .
N3 N 0.35367(16) 1.05140(11) 1.24087(11) 0.0124(2) 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 Cu1 2.5638(4) 2_677 ?
Cu1 Cl1 2.3679(4) . ?
Cu1 C1 1.9447(15) . ?
Cu1 N3 2.0482(13) 2_677 ?
Cl2 C19 1.7623(18) . ?
Cl3 C19 1.7632(18) . ?
N1 C1 1.3692(19) . ?
N1 C2 1.3913(19) . ?
N1 C4 1.4437(19) . ?
N2 C13 1.4683(18) . ?
N2 C1 1.3548(19) . ?
N2 C3 1.3869(19) . ?
C13 C14 1.509(2) . ?
C9 C4 1.397(2) . ?
C9 C8 1.393(2) . ?
C9 C12 1.502(2) . ?
C2 C3 1.348(2) . ?
C6 C5 1.394(2) . ?
C6 C7 1.393(2) . ?
C14 C15 1.387(2) . ?
C14 N3 1.3480(19) . ?
C4 C5 1.396(2) . ?
C18 C17 1.382(2) . ?
C18 N3 1.348(2) . ?
C15 C16 1.391(2) . ?
C17 C16 1.385(2) . ?
C8 C7 1.390(2) . ?
C5 C10 1.507(2) . ?
C7 C11 1.510(2) . ?
N3 Cu1 2.0482(13) 2_677 ?

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
Cl1 Cu1 Cu1 131.933(15) . 2_677 ?
C1 Cu1 Cu1 68.31(4) . 2_677 ?
C1 Cu1 Cl1 107.14(5) . . ?
C1 Cu1 N3 131.94(6) . 2_677 ?
N3 Cu1 Cu1 122.54(4) 2_677 2_677 ?
N3 Cu1 Cl1 96.63(4) 2_677 . ?
C1 N1 C2 111.43(12) . . ?
C1 N1 C4 122.19(12) . . ?
C2 N1 C4 124.62(12) . . ?
C1 N2 C13 123.78(12) . . ?
C1 N2 C3 112.25(12) . . ?
C3 N2 C13 123.96(12) . . ?
N2 C13 C14 112.11(12) . . ?
C4 C9 C12 121.61(14) . . ?
C8 C9 C4 117.51(15) . . ?
C8 C9 C12 120.86(14) . . ?
N1 C1 Cu1 122.57(11) . . ?
N2 C1 Cu1 129.57(11) . . ?
N2 C1 N1 103.33(12) . . ?
C3 C2 N1 106.58(13) . . ?
C2 C3 N2 106.40(13) . . ?
C7 C6 C5 121.61(15) . . ?
C15 C14 C13 121.17(13) . . ?
N3 C14 C13 116.30(13) . . ?
N3 C14 C15 122.53(14) . . ?
C9 C4 N1 120.01(13) . . ?
C5 C4 N1 117.78(13) . . ?
C5 C4 C9 122.16(14) . . ?
N3 C18 C17 123.15(14) . . ?
C14 C15 C16 119.17(14) . . ?
C18 C17 C16 118.94(15) . . ?
C7 C8 C9 122.19(15) . . ?
C6 C5 C4 118.02(14) . . ?
C6 C5 C10 120.57(15) . . ?
C4 C5 C10 121.38(14) . . ?
C6 C7 C11 120.84(16) . . ?
C8 C7 C6 118.40(15) . . ?
C8 C7 C11 120.76(16) . . ?
Cl2 C19 Cl3 111.46(9) . . ?
C17 C16 C15 118.57(15) . . ?
C14 N3 Cu1 124.31(10) . 2_677 ?
C14 N3 C18 117.63(13) . . ?
C18 N3 Cu1 117.99(10) . 2_677 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 0.68(17) . . . . ?
N1 C4 C5 C6 176.28(13) . . . . ?
N1 C4 C5 C10 -1.3(2) . . . . ?
N2 C13 C14 C15 -120.96(15) . . . . ?
N2 C13 C14 N3 59.38(17) . . . . ?
C13 N2 C1 Cu1 -23.1(2) . . . . ?
C13 N2 C1 N1 -179.12(12) . . . . ?
C13 N2 C3 C2 178.50(13) . . . . ?
C13 C14 C15 C16 -179.08(14) . . . . ?
C13 C14 N3 Cu1 2.61(18) . . . 2_677 ?
C13 C14 N3 C18 179.44(13) . . . . ?
C9 C4 C5 C6 -1.0(2) . . . . ?
C9 C4 C5 C10 -178.60(15) . . . . ?
C9 C8 C7 C6 -0.2(2) . . . . ?
C9 C8 C7 C11 -179.52(16) . . . . ?
C1 N1 C2 C3 -1.04(17) . . . . ?
C1 N1 C4 C9 87.69(18) . . . . ?
C1 N1 C4 C5 -89.63(17) . . . . ?
C1 N2 C13 C14 -95.05(16) . . . . ?
C1 N2 C3 C2 -0.13(17) . . . . ?
C2 N1 C1 Cu1 -157.25(11) . . . . ?
C2 N1 C1 N2 0.93(16) . . . . ?
C2 N1 C4 C9 -108.76(17) . . . . ?
C2 N1 C4 C5 73.92(19) . . . . ?
C3 N2 C13 C14 86.47(16) . . . . ?
C3 N2 C1 Cu1 155.53(12) . . . . ?
C3 N2 C1 N1 -0.49(16) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C4 N1 C1 Cu1 8.26(19) . . . . ?
C4 N1 C1 N2 166.43(13) . . . . ?
C4 N1 C2 C3 -166.13(14) . . . . ?
C4 C9 C8 C7 -2.8(2) . . . . ?
C18 C17 C16 C15 -0.3(2) . . . . ?
C15 C14 N3 Cu1 -177.04(11) . . . 2_677 ?
C15 C14 N3 C18 -0.2(2) . . . . ?
C17 C18 N3 Cu1 176.61(12) . . . 2_677 ?
C17 C18 N3 C14 -0.4(2) . . . . ?
C8 C9 C4 N1 -173.79(13) . . . . ?
C8 C9 C4 C5 3.4(2) . . . . ?
C5 C6 C7 C8 2.8(2) . . . . ?
C5 C6 C7 C11 -177.89(16) . . . . ?
C12 C9 C4 N1 7.9(2) . . . . ?
C12 C9 C4 C5 -174.93(15) . . . . ?
C12 C9 C8 C7 175.57(15) . . . . ?
C7 C6 C5 C4 -2.2(2) . . . . ?
C7 C6 C5 C10 175.41(16) . . . . ?
N3 C14 C15 C16 0.6(2) . . . . ?
N3 C18 C17 C16 0.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_al064_0m
_database_code_depnum_ccdc_archive 'CCDC 1038477'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;
_audit_creation_date             2014-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C38 H42 Cl2 Cu2 N6, 2(C H2 Cl2)'
_chemical_formula_sum            'C40 H46 Cl6 Cu2 N6'
_chemical_formula_weight         950.61
_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'

_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                   8.3056(14)
_cell_length_b                   11.1055(19)
_cell_length_c                   11.873(2)
_cell_angle_alpha                86.315(6)
_cell_angle_beta                 89.284(6)
_cell_angle_gamma                77.720(6)
_cell_volume                     1067.9(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3047
_cell_measurement_temperature    290
_cell_measurement_theta_max      22.14
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.715
_exptl_absorpt_coefficient_mu    1.408
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0512 before and 0.0369 after correction.
The Ratio of minimum to maximum transmission is 0.8460.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12827
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.788
_diffrn_reflns_theta_min         1.719
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2994
_reflns_number_total             4523
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.045
_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)+(0.0800P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1458
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C15(H15), C3(H3), C6(H6), C18(H18), C8(H8), C17(H17)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C11(H11A,H11B,
 H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.45352(5) 0.98145(4) 0.39661(4) 0.04561(18) Uani 1 1 d . . . . .
Cl1 Cl 0.22236(11) 1.08132(9) 0.28733(9) 0.0529(3) Uani 1 1 d . . . . .
Cl3 Cl 0.3605(2) 0.75740(16) 0.91836(15) 0.1084(5) Uani 1 1 d . . . . .
Cl2 Cl 0.6742(2) 0.59592(17) 0.89616(14) 0.1141(6) Uani 1 1 d . . . . .
N1 N 0.4220(3) 0.7421(2) 0.5013(2) 0.0386(7) Uani 1 1 d . . . . .
N2 N 0.2500(3) 0.8871(2) 0.5757(2) 0.0334(6) Uani 1 1 d . . . . .
C1 C 0.3828(4) 0.8684(3) 0.5068(3) 0.0353(7) Uani 1 1 d . . . . .
C9 C 0.7048(5) 0.6452(3) 0.4520(3) 0.0442(9) Uani 1 1 d . . . . .
C14 C 0.2134(4) 1.0453(3) 0.7171(3) 0.0349(7) Uani 1 1 d . . . . .
C2 C 0.3145(5) 0.6876(3) 0.5658(3) 0.0506(10) Uani 1 1 d . . . . .
H2 H 0.3162 0.6035 0.5750 0.061 Uiso 1 1 calc R . . . .
C13 C 0.1615(4) 1.0097(3) 0.6053(3) 0.0374(8) Uani 1 1 d . . . . .
H13A H 0.0443 1.0112 0.6074 0.045 Uiso 1 1 calc R . . . .
H13B H 0.1801 1.0704 0.5469 0.045 Uiso 1 1 calc R . . . .
C15 C 0.1012(4) 1.0800(3) 0.8001(3) 0.0442(9) Uani 1 1 d . . . . .
H15 H -0.0090 1.0787 0.7888 0.053 Uiso 1 1 calc R . . . .
C4 C 0.5395(4) 0.6813(3) 0.4223(3) 0.0388(8) Uani 1 1 d . . . . .
C3 C 0.2074(5) 0.7781(3) 0.6127(3) 0.0473(9) Uani 1 1 d . . . . .
H3 H 0.1210 0.7691 0.6609 0.057 Uiso 1 1 calc R . . . .
C6 C 0.6000(6) 0.6080(4) 0.2391(3) 0.0573(11) Uani 1 1 d . . . . .
H6 H 0.5646 0.5931 0.1683 0.069 Uiso 1 1 calc R . . . .
C10 C 0.3055(6) 0.7046(5) 0.2824(4) 0.0689(13) Uani 1 1 d . . . . .
H10A H 0.2390 0.6658 0.3338 0.103 Uiso 1 1 calc GR . . . .
H10B H 0.2905 0.6820 0.2072 0.103 Uiso 1 1 calc GR . . . .
H10C H 0.2730 0.7927 0.2852 0.103 Uiso 1 1 calc GR . . . .
C16 C 0.1498(5) 1.1167(4) 0.9004(3) 0.0507(10) Uani 1 1 d . . . . .
C18 C 0.4226(5) 1.0747(4) 0.8282(3) 0.0500(10) Uani 1 1 d . . . . .
H18 H 0.5341 1.0710 0.8397 0.060 Uiso 1 1 calc R . . . .
C8 C 0.8148(5) 0.5948(3) 0.3700(4) 0.0521(10) Uani 1 1 d . . . . .
H8 H 0.9265 0.5738 0.3876 0.063 Uiso 1 1 calc R . . . .
C5 C 0.4841(5) 0.6628(3) 0.3154(3) 0.0485(9) Uani 1 1 d . . . . .
C17 C 0.3162(5) 1.1119(4) 0.9127(4) 0.0578(11) Uani 1 1 d . . . . .
H17 H 0.3555 1.1344 0.9795 0.069 Uiso 1 1 calc R . . . .
C7 C 0.7660(5) 0.5746(4) 0.2639(4) 0.0545(10) Uani 1 1 d . . . . .
C12 C 0.7633(6) 0.6578(4) 0.5684(4) 0.0692(13) Uani 1 1 d . . . . .
H12A H 0.7199 0.7400 0.5906 0.104 Uiso 1 1 calc GR . . . .
H12B H 0.8815 0.6420 0.5692 0.104 Uiso 1 1 calc GR . . . .
H12C H 0.7261 0.5995 0.6202 0.104 Uiso 1 1 calc GR . . . .
C20 C 0.5255(6) 0.7092(5) 0.8314(4) 0.0827(15) Uani 1 1 d . . . . .
H20A H 0.4873 0.6783 0.7643 0.099 Uiso 1 1 calc R . . . .
H20B H 0.5733 0.7792 0.8079 0.099 Uiso 1 1 calc R . . . .
C19 C 0.0301(8) 1.1628(6) 0.9893(5) 0.102(2) Uani 1 1 d . . . . .
H19A H 0.0026 1.2514 0.9823 0.154 Uiso 1 1 calc GR . . . .
H19B H 0.0780 1.1357 1.0621 0.154 Uiso 1 1 calc GR . . . .
H19C H -0.0678 1.1313 0.9810 0.154 Uiso 1 1 calc GR . . . .
C11 C 0.8910(7) 0.5163(5) 0.1788(4) 0.0880(16) Uani 1 1 d . . . . .
H11A H 0.9347 0.4316 0.2032 0.132 Uiso 1 1 calc GR . . . .
H11B H 0.9789 0.5602 0.1727 0.132 Uiso 1 1 calc GR . . . .
H11C H 0.8388 0.5201 0.1067 0.132 Uiso 1 1 calc GR . . . .
N3 N 0.3751(3) 1.0432(3) 0.7291(2) 0.0377(7) 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 Cu1 2.6659(10) 2_676 ?
Cu1 Cl1 2.3604(11) . ?
Cu1 C1 1.927(3) . ?
Cu1 N3 2.040(3) 2_676 ?
Cl3 C20 1.719(5) . ?
Cl2 C20 1.714(5) . ?
N1 C1 1.377(4) . ?
N1 C2 1.380(4) . ?
N1 C4 1.438(4) . ?
N2 C1 1.353(4) . ?
N2 C13 1.465(4) . ?
N2 C3 1.376(4) . ?
C9 C4 1.389(5) . ?
C9 C8 1.388(5) . ?
C9 C12 1.496(6) . ?
C14 C13 1.503(5) . ?
C14 C15 1.364(5) . ?
C14 N3 1.348(4) . ?
C2 C3 1.339(5) . ?
C15 C16 1.375(5) . ?
C4 C5 1.397(5) . ?
C6 C5 1.385(6) . ?
C6 C7 1.380(6) . ?
C10 C5 1.506(6) . ?
C16 C17 1.381(5) . ?
C16 C19 1.480(6) . ?
C18 C17 1.355(5) . ?
C18 N3 1.336(5) . ?
C8 C7 1.374(6) . ?
C7 C11 1.513(6) . ?
N3 Cu1 2.040(3) 2_676 ?

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
Cl1 Cu1 Cu1 131.00(4) . 2_676 ?
C1 Cu1 Cu1 69.30(10) . 2_676 ?
C1 Cu1 Cl1 108.08(10) . . ?
C1 Cu1 N3 132.54(13) . 2_676 ?
N3 Cu1 Cu1 119.19(8) 2_676 2_676 ?
N3 Cu1 Cl1 98.64(9) 2_676 . ?
C1 N1 C2 110.7(3) . . ?
C1 N1 C4 122.8(3) . . ?
C2 N1 C4 125.6(3) . . ?
C1 N2 C13 123.5(3) . . ?
C1 N2 C3 112.1(3) . . ?
C3 N2 C13 124.5(3) . . ?
N1 C1 Cu1 123.5(2) . . ?
N2 C1 Cu1 129.3(2) . . ?
N2 C1 N1 103.4(3) . . ?
C4 C9 C12 121.7(4) . . ?
C8 C9 C4 117.6(4) . . ?
C8 C9 C12 120.7(4) . . ?
C15 C14 C13 121.3(3) . . ?
N3 C14 C13 116.2(3) . . ?
N3 C14 C15 122.5(3) . . ?
C3 C2 N1 107.3(3) . . ?
N2 C13 C14 113.1(3) . . ?
C14 C15 C16 120.5(3) . . ?
C9 C4 N1 119.9(3) . . ?
C9 C4 C5 121.5(3) . . ?
C5 C4 N1 118.6(3) . . ?
C2 C3 N2 106.6(3) . . ?
C7 C6 C5 122.6(4) . . ?
C15 C16 C17 116.5(4) . . ?
C15 C16 C19 122.0(4) . . ?
C17 C16 C19 121.4(4) . . ?
N3 C18 C17 123.3(4) . . ?
C7 C8 C9 122.9(4) . . ?
C4 C5 C10 121.4(3) . . ?
C6 C5 C4 117.8(4) . . ?
C6 C5 C10 120.8(4) . . ?
C18 C17 C16 120.4(4) . . ?
C6 C7 C11 121.8(4) . . ?
C8 C7 C6 117.6(4) . . ?
C8 C7 C11 120.6(4) . . ?
Cl2 C20 Cl3 112.3(3) . . ?
C14 N3 Cu1 125.5(2) . 2_676 ?
C18 N3 Cu1 117.3(2) . 2_676 ?
C18 N3 C14 116.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 0.4(4) . . . . ?
N1 C4 C5 C6 177.8(3) . . . . ?
N1 C4 C5 C10 -0.3(5) . . . . ?
C1 N1 C2 C3 -0.2(4) . . . . ?
C1 N1 C4 C9 90.1(4) . . . . ?
C1 N1 C4 C5 -88.2(4) . . . . ?
C1 N2 C13 C14 -97.5(4) . . . . ?
C1 N2 C3 C2 -0.4(4) . . . . ?
C9 C4 C5 C6 -0.5(5) . . . . ?
C9 C4 C5 C10 -178.6(4) . . . . ?
C9 C8 C7 C6 0.9(6) . . . . ?
C9 C8 C7 C11 -178.4(4) . . . . ?
C14 C15 C16 C17 -2.3(6) . . . . ?
C14 C15 C16 C19 175.8(4) . . . . ?
C2 N1 C1 Cu1 -160.0(3) . . . . ?
C2 N1 C1 N2 -0.1(4) . . . . ?
C2 N1 C4 C9 -102.0(4) . . . . ?
C2 N1 C4 C5 79.7(4) . . . . ?
C13 N2 C1 Cu1 -20.5(5) . . . . ?
C13 N2 C1 N1 -178.8(3) . . . . ?
C13 N2 C3 C2 178.6(3) . . . . ?
C13 C14 C15 C16 -177.6(3) . . . . ?
C13 C14 N3 Cu1 8.5(4) . . . 2_676 ?
C13 C14 N3 C18 -180.0(3) . . . . ?
C15 C14 C13 N2 -124.9(3) . . . . ?
C15 C14 N3 Cu1 -170.2(3) . . . 2_676 ?
C15 C14 N3 C18 1.3(5) . . . . ?
C15 C16 C17 C18 1.2(6) . . . . ?
C4 N1 C1 Cu1 9.5(5) . . . . ?
C4 N1 C1 N2 169.4(3) . . . . ?
C4 N1 C2 C3 -169.3(3) . . . . ?
C4 C9 C8 C7 -2.9(5) . . . . ?
C3 N2 C1 Cu1 158.6(3) . . . . ?
C3 N2 C1 N1 0.3(4) . . . . ?
C3 N2 C13 C14 83.6(4) . . . . ?
C8 C9 C4 N1 -175.5(3) . . . . ?
C8 C9 C4 C5 2.7(5) . . . . ?
C5 C6 C7 C8 1.5(6) . . . . ?
C5 C6 C7 C11 -179.2(4) . . . . ?
C17 C18 N3 Cu1 169.7(3) . . . 2_676 ?
C17 C18 N3 C14 -2.5(6) . . . . ?
C7 C6 C5 C4 -1.7(6) . . . . ?
C7 C6 C5 C10 176.4(4) . . . . ?
C12 C9 C4 N1 5.5(5) . . . . ?
C12 C9 C4 C5 -176.3(4) . . . . ?
C12 C9 C8 C7 176.1(4) . . . . ?
C19 C16 C17 C18 -176.9(4) . . . . ?
N3 C14 C13 N2 56.4(4) . . . . ?
N3 C14 C15 C16 1.1(6) . . . . ?
N3 C18 C17 C16 1.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_al058_0m
_database_code_depnum_ccdc_archive 'CCDC 1038478'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;
_audit_creation_date             2014-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C38 H42 Cl2 Cu2 N6, 2(C H2 Cl2)'
_chemical_formula_sum            'C40 H46 Cl6 Cu2 N6'
_chemical_formula_weight         950.61
_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'

_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                   8.3293(13)
_cell_length_b                   10.9929(17)
_cell_length_c                   11.7343(18)
_cell_angle_alpha                86.079(5)
_cell_angle_beta                 89.732(6)
_cell_angle_gamma                77.869(5)
_cell_volume                     1047.9(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5554
_cell_measurement_temperature    102
_cell_measurement_theta_max      26.68
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.595
_exptl_absorpt_coefficient_mu    1.435
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0618 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.8587.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.138
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15195
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.718
_diffrn_reflns_theta_min         1.740
_diffrn_ambient_temperature      102
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3698
_reflns_number_total             4437
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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., 2013)'
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.161
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.146
_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)+(0.0686P)²+0.1674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1225
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C15(H15), C18(H18), C6(H6), C17(H17), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C)
;
_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
Cu1 Cu 0.04269(4) 0.01602(3) 0.60193(3) 0.01753(13) Uani 1 1 d . . . . .
Cl1 Cl 0.27820(8) -0.07822(6) 0.71441(6) 0.01971(17) Uani 1 1 d . . . . .
Cl2 Cl -0.17248(12) 0.40840(9) 1.10085(7) 0.0412(2) Uani 1 1 d . . . . .
Cl3 Cl 0.14747(11) 0.24163(8) 1.08535(8) 0.0409(2) Uani 1 1 d . . . . .
N1 N 0.0770(3) 0.2597(2) 0.49676(19) 0.0142(5) Uani 1 1 d . . . . .
N3 N 0.1250(3) -0.0444(2) 0.26916(19) 0.0153(5) Uani 1 1 d . . . . .
N2 N 0.2519(3) 0.11347(19) 0.42410(18) 0.0129(5) Uani 1 1 d . . . . .
C2 C 0.1880(3) 0.3166(3) 0.4359(2) 0.0184(6) Uani 1 1 d . . . . .
H2 H 0.1871 0.4033 0.4281 0.022 Uiso 1 1 calc R . . . .
C1 C 0.1152(3) 0.1321(2) 0.4909(2) 0.0142(5) Uani 1 1 d . . . . .
C8 C -0.3203(4) 0.4048(3) 0.6279(3) 0.0210(6) Uani 1 1 d . . . . .
H8 H -0.4342 0.4252 0.6094 0.025 Uiso 1 1 calc R . . . .
C15 C 0.3998(3) -0.0822(3) 0.1962(2) 0.0188(6) Uani 1 1 d . . . . .
H15 H 0.5125 -0.0817 0.2079 0.023 Uiso 1 1 calc R . . . .
C10 C 0.1929(4) 0.2966(3) 0.7193(3) 0.0254(7) Uani 1 1 d . . . . .
H10A H 0.2587 0.3429 0.6707 0.038 Uiso 1 1 calc GR . . . .
H10B H 0.2287 0.2072 0.7096 0.038 Uiso 1 1 calc GR . . . .
H10C H 0.2075 0.3125 0.7994 0.038 Uiso 1 1 calc GR . . . .
C18 C 0.0747(3) -0.0762(3) 0.1681(2) 0.0190(6) Uani 1 1 d . . . . .
H18 H -0.0392 -0.0724 0.1570 0.023 Uiso 1 1 calc R . . . .
C14 C 0.2873(3) -0.0466(2) 0.2815(2) 0.0143(5) Uani 1 1 d . . . . .
C6 C -0.1023(4) 0.3923(3) 0.7635(2) 0.0229(6) Uani 1 1 d . . . . .
H6 H -0.0664 0.4073 0.8370 0.027 Uiso 1 1 calc R . . . .
C13 C 0.3418(3) -0.0112(2) 0.3949(2) 0.0143(5) Uani 1 1 d . . . . .
H13A H 0.3242 -0.0741 0.4555 0.017 Uiso 1 1 calc R . . . .
H13B H 0.4608 -0.0120 0.3922 0.017 Uiso 1 1 calc R . . . .
C17 C 0.1800(4) -0.1138(3) 0.0802(2) 0.0224(6) Uani 1 1 d . . . . .
H17 H 0.1390 -0.1363 0.0110 0.027 Uiso 1 1 calc R . . . .
C16 C 0.3486(4) -0.1183(3) 0.0940(2) 0.0216(6) Uani 1 1 d . . . . .
C3 C 0.2981(3) 0.2244(3) 0.3898(2) 0.0177(6) Uani 1 1 d . . . . .
H3 H 0.3888 0.2339 0.3433 0.021 Uiso 1 1 calc R . . . .
C9 C -0.2089(3) 0.3555(2) 0.5449(2) 0.0180(6) Uani 1 1 d . . . . .
C11 C -0.3948(4) 0.4816(3) 0.8232(3) 0.0357(8) Uani 1 1 d . . . . .
H11A H -0.5048 0.4998 0.7885 0.054 Uiso 1 1 calc GR . . . .
H11B H -0.3684 0.5590 0.8468 0.054 Uiso 1 1 calc GR . . . .
H11C H -0.3919 0.4226 0.8900 0.054 Uiso 1 1 calc GR . . . .
C7 C -0.2700(4) 0.4250(3) 0.7369(2) 0.0213(6) Uani 1 1 d . . . . .
C4 C -0.0420(3) 0.3203(2) 0.5766(2) 0.0151(6) Uani 1 1 d . . . . .
C5 C 0.0137(4) 0.3386(2) 0.6859(2) 0.0186(6) Uani 1 1 d . . . . .
C12 C -0.2670(4) 0.3447(3) 0.4253(3) 0.0261(7) Uani 1 1 d . . . . .
H12A H -0.3869 0.3567 0.4241 0.039 Uiso 1 1 calc GR . . . .
H12B H -0.2183 0.2617 0.4004 0.039 Uiso 1 1 calc GR . . . .
H12C H -0.2335 0.4085 0.3736 0.039 Uiso 1 1 calc GR . . . .
C20 C -0.0226(4) 0.2919(3) 1.1732(3) 0.0337(8) Uani 1 1 d . . . . .
H20A H -0.0718 0.2199 1.1978 0.040 Uiso 1 1 calc R . . . .
H20B H 0.0147 0.3251 1.2425 0.040 Uiso 1 1 calc R . . . .
C19 C 0.4689(5) -0.1656(4) 0.0056(3) 0.0481(10) Uani 1 1 d . . . . .
H19A H 0.5646 -0.1273 0.0107 0.072 Uiso 1 1 calc GR . . . .
H19B H 0.4179 -0.1445 -0.0702 0.072 Uiso 1 1 calc GR . . . .
H19C H 0.5039 -0.2564 0.0180 0.072 Uiso 1 1 calc GR . . . .


_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 Cu1 2.5668(8) 2_556 ?
Cu1 Cl1 2.3762(8) . ?
Cu1 N3 2.049(2) 2_556 ?
Cu1 C1 1.945(3) . ?
Cl2 C20 1.763(3) . ?
Cl3 C20 1.764(4) . ?
N1 C2 1.390(3) . ?
N1 C1 1.378(3) . ?
N1 C4 1.450(3) . ?
N3 Cu1 2.049(2) 2_556 ?
N3 C18 1.352(3) . ?
N3 C14 1.355(3) . ?
N2 C1 1.367(3) . ?
N2 C13 1.479(3) . ?
N2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.356(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.399(4) . ?
C8 C7 1.394(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.387(4) . ?
C15 C16 1.386(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C5 1.513(4) . ?
C18 H18 0.9500 . ?
C18 C17 1.379(4) . ?
C14 C13 1.509(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(4) . ?
C6 C5 1.391(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C16 1.405(4) . ?
C16 C19 1.482(4) . ?
C3 H3 0.9500 . ?
C9 C4 1.407(4) . ?
C9 C12 1.507(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C7 1.516(4) . ?
C4 C5 1.407(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
Cl1 Cu1 Cu1 131.81(3) . 2_556 ?
N3 Cu1 Cu1 121.60(7) 2_556 2_556 ?
N3 Cu1 Cl1 98.35(7) 2_556 . ?
C1 Cu1 Cu1 68.58(8) . 2_556 ?
C1 Cu1 Cl1 105.88(8) . . ?
C1 Cu1 N3 131.38(10) . 2_556 ?
C2 N1 C4 125.0(2) . . ?
C1 N1 C2 111.4(2) . . ?
C1 N1 C4 122.3(2) . . ?
C18 N3 Cu1 118.01(18) . 2_556 ?
C18 N3 C14 117.1(2) . . ?
C14 N3 Cu1 124.46(18) . 2_556 ?
C1 N2 C13 123.5(2) . . ?
C1 N2 C3 112.1(2) . . ?
C3 N2 C13 124.3(2) . . ?
N1 C2 H2 126.6 . . ?
C3 C2 N1 106.8(2) . . ?
C3 C2 H2 126.6 . . ?
N1 C1 Cu1 123.64(19) . . ?
N2 C1 Cu1 128.83(18) . . ?
N2 C1 N1 103.2(2) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C7 C8 C9 122.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C14 120.3(3) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
N3 C18 H18 118.3 . . ?
N3 C18 C17 123.5(3) . . ?
C17 C18 H18 118.3 . . ?
N3 C14 C15 122.4(2) . . ?
N3 C14 C13 116.6(2) . . ?
C15 C14 C13 121.0(2) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.2(3) . . ?
N2 C13 C14 112.4(2) . . ?
N2 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C18 C17 H17 120.4 . . ?
C18 C17 C16 119.3(3) . . ?
C16 C17 H17 120.4 . . ?
C15 C16 C17 117.4(3) . . ?
C15 C16 C19 120.9(3) . . ?
C17 C16 C19 121.7(3) . . ?
N2 C3 H3 126.8 . . ?
C2 C3 N2 106.5(2) . . ?
C2 C3 H3 126.8 . . ?
C8 C9 C4 117.6(3) . . ?
C8 C9 C12 120.5(3) . . ?
C4 C9 C12 121.9(3) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
C8 C7 C6 118.2(3) . . ?
C8 C7 C11 120.4(3) . . ?
C6 C7 C11 121.4(3) . . ?
C9 C4 N1 119.9(2) . . ?
C9 C4 C5 121.8(3) . . ?
C5 C4 N1 118.3(2) . . ?
C6 C5 C10 121.1(3) . . ?
C6 C5 C4 117.9(3) . . ?
C4 C5 C10 121.0(3) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Cl2 C20 Cl3 111.33(18) . . ?
Cl2 C20 H20A 109.4 . . ?
Cl2 C20 H20B 109.4 . . ?
Cl3 C20 H20A 109.4 . . ?
Cl3 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Cu1 N3 C18 C17 -171.1(2) 2_556 . . . ?
Cu1 N3 C14 C15 171.35(19) 2_556 . . . ?
Cu1 N3 C14 C13 -7.1(3) 2_556 . . . ?
N1 C2 C3 N2 -0.3(3) . . . . ?
N1 C4 C5 C10 0.2(4) . . . . ?
N1 C4 C5 C6 -177.5(2) . . . . ?
N3 C18 C17 C16 -0.9(4) . . . . ?
N3 C14 C13 N2 -55.9(3) . . . . ?
C2 N1 C1 Cu1 158.0(2) . . . . ?
C2 N1 C1 N2 -0.4(3) . . . . ?
C2 N1 C4 C9 105.0(3) . . . . ?
C2 N1 C4 C5 -77.0(3) . . . . ?
C1 N1 C2 C3 0.4(3) . . . . ?
C1 N1 C4 C9 -88.9(3) . . . . ?
C1 N1 C4 C5 89.1(3) . . . . ?
C1 N2 C13 C14 94.8(3) . . . . ?
C1 N2 C3 C2 0.0(3) . . . . ?
C8 C9 C4 N1 175.2(2) . . . . ?
C8 C9 C4 C5 -2.8(4) . . . . ?
C15 C14 C13 N2 125.6(3) . . . . ?
C18 N3 C14 C15 -1.4(4) . . . . ?
C18 N3 C14 C13 -179.9(2) . . . . ?
C18 C17 C16 C15 -1.1(4) . . . . ?
C18 C17 C16 C19 176.0(3) . . . . ?
C14 N3 C18 C17 2.1(4) . . . . ?
C14 C15 C16 C17 1.8(4) . . . . ?
C14 C15 C16 C19 -175.3(3) . . . . ?
C13 N2 C1 Cu1 21.9(4) . . . . ?
C13 N2 C1 N1 178.7(2) . . . . ?
C13 N2 C3 C2 -178.5(2) . . . . ?
C16 C15 C14 N3 -0.5(4) . . . . ?
C16 C15 C14 C13 177.9(2) . . . . ?
C3 N2 C1 Cu1 -156.6(2) . . . . ?
C3 N2 C1 N1 0.2(3) . . . . ?
C3 N2 C13 C14 -86.9(3) . . . . ?
C9 C8 C7 C6 -1.2(4) . . . . ?
C9 C8 C7 C11 178.5(3) . . . . ?
C9 C4 C5 C10 178.1(3) . . . . ?
C9 C4 C5 C6 0.5(4) . . . . ?
C7 C8 C9 C4 3.1(4) . . . . ?
C7 C8 C9 C12 -175.1(3) . . . . ?
C7 C6 C5 C10 -176.1(3) . . . . ?
C7 C6 C5 C4 1.6(4) . . . . ?
C4 N1 C2 C3 167.8(2) . . . . ?
C4 N1 C1 Cu1 -9.8(4) . . . . ?
C4 N1 C1 N2 -168.1(2) . . . . ?
C5 C6 C7 C8 -1.3(4) . . . . ?
C5 C6 C7 C11 179.0(3) . . . . ?
C12 C9 C4 N1 -6.6(4) . . . . ?
C12 C9 C4 C5 175.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_al007_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1038479'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;
_audit_creation_date             2014-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36 H36 Cl4 Cu2 N6, 2(C H2 Cl2)'
_chemical_formula_sum            'C38 H40 Cl8 Cu2 N6'
_chemical_formula_weight         991.44
_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'

_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                   8.253(3)
_cell_length_b                   10.948(3)
_cell_length_c                   11.802(4)
_cell_angle_alpha                85.792(9)
_cell_angle_beta                 89.721(9)
_cell_angle_gamma                78.477(9)
_cell_volume                     1041.9(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8781
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.822
_shelx_estimated_absorpt_T_min   0.538
_exptl_absorpt_coefficient_mu    1.570
_exptl_absorpt_correction_T_max  0.8320
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0500 before and 0.0406 after correction.
The Ratio of minimum to maximum transmission is 0.7108.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.436
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14284
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.983
_diffrn_reflns_theta_min         1.730
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4123
_reflns_number_total             4444
_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       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4444
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.162
_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)+(0.0544P)²+0.3981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0952
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
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
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C2(H2), C8(H8), C17(H17), C6(H6), C3(H3)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.54406(3) 0.51380(2) 0.59967(2) 0.01588(9) Uani 1 1 d . . . . .
Cl1 Cl 0.77922(5) 0.42345(4) 0.70898(4) 0.01807(12) Uani 1 1 d . . . . .
Cl2 Cl 0.98032(7) 0.33313(5) -0.00618(4) 0.02687(14) Uani 1 1 d . . . . .
Cl3 Cl 1.36223(7) 0.26065(5) -0.08504(5) 0.02947(14) Uani 1 1 d . . . . .
Cl4 Cl 1.67598(7) 0.08636(6) -0.10102(5) 0.03805(16) Uani 1 1 d . . . . .
N1 N 0.57421(19) 0.76055(14) 0.49622(13) 0.0135(3) Uani 1 1 d . . . . .
N3 N 0.62207(19) 0.45784(15) 0.27104(13) 0.0138(3) Uani 1 1 d . . . . .
N2 N 0.74918(18) 0.61715(14) 0.42324(13) 0.0121(3) Uani 1 1 d . . . . .
C15 C 0.8984(2) 0.42175(18) 0.19874(16) 0.0146(4) Uani 1 1 d . . . . .
H15 H 1.0119 0.4238 0.2091 0.017 Uiso 1 1 calc R . . . .
C4 C 0.4564(2) 0.81999(17) 0.57645(16) 0.0140(4) Uani 1 1 d . . . . .
C18 C 0.5708(2) 0.42510(19) 0.17157(17) 0.0180(4) Uani 1 1 d . . . . .
H18 H 0.4558 0.4286 0.1612 0.022 Uiso 1 1 calc R . . . .
C9 C 0.2888(2) 0.85481(17) 0.54598(17) 0.0162(4) Uani 1 1 d . . . . .
C14 C 0.7848(2) 0.45678(17) 0.28263(15) 0.0122(3) Uani 1 1 d . . . . .
C2 C 0.6849(2) 0.82017(18) 0.43559(17) 0.0171(4) Uani 1 1 d . . . . .
H2 H 0.6836 0.9074 0.4284 0.020 Uiso 1 1 calc R . . . .
C5 C 0.5140(2) 0.83724(18) 0.68432(17) 0.0179(4) Uani 1 1 d . . . . .
C13 C 0.8402(2) 0.49394(17) 0.39507(15) 0.0130(3) Uani 1 1 d . . . . .
H13A H 0.8238 0.4306 0.4560 0.016 Uiso 1 1 calc R . . . .
H13B H 0.9598 0.4950 0.3918 0.016 Uiso 1 1 calc R . . . .
C8 C 0.1788(2) 0.90292(18) 0.62908(18) 0.0196(4) Uani 1 1 d . . . . .
H8 H 0.0640 0.9236 0.6112 0.024 Uiso 1 1 calc R . . . .
C17 C 0.6756(2) 0.3866(2) 0.08360(17) 0.0195(4) Uani 1 1 d . . . . .
H17 H 0.6345 0.3631 0.0151 0.023 Uiso 1 1 calc R . . . .
C7 C 0.2305(3) 0.92187(19) 0.73703(18) 0.0210(4) Uani 1 1 d . . . . .
C1 C 0.6127(2) 0.63402(17) 0.48933(15) 0.0130(3) Uani 1 1 d . . . . .
C16 C 0.8427(2) 0.38358(18) 0.09905(16) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.3992(3) 0.89030(19) 0.76290(18) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.4366 0.9053 0.8356 0.025 Uiso 1 1 calc R . . . .
C3 C 0.7946(2) 0.72936(18) 0.38897(16) 0.0162(4) Uani 1 1 d . . . . .
H3 H 0.8851 0.7403 0.3419 0.019 Uiso 1 1 calc R . . . .
C12 C 0.2305(3) 0.8457(2) 0.42721(19) 0.0238(4) Uani 1 1 d . . . . .
H12A H 0.2686 0.9084 0.3759 0.036 Uiso 1 1 calc GR . . . .
H12B H 0.1094 0.8607 0.4253 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.2754 0.7620 0.4029 0.036 Uiso 1 1 calc GR . . . .
C10 C 0.6941(3) 0.7956(2) 0.71667(19) 0.0239(4) Uani 1 1 d . . . . .
H10A H 0.7298 0.7064 0.7054 0.036 Uiso 1 1 calc GR . . . .
H10B H 0.7094 0.8094 0.7967 0.036 Uiso 1 1 calc GR . . . .
H10C H 0.7601 0.8437 0.6690 0.036 Uiso 1 1 calc GR . . . .
C11 C 0.1077(3) 0.9771(2) 0.8244(2) 0.0332(6) Uani 1 1 d . . . . .
H11A H 0.1356 1.0546 0.8476 0.050 Uiso 1 1 calc GR . . . .
H11B H 0.1121 0.9173 0.8908 0.050 Uiso 1 1 calc GR . . . .
H11C H -0.0040 0.9952 0.7913 0.050 Uiso 1 1 calc GR . . . .
C19 C 1.5309(3) 0.2064(2) -0.17292(18) 0.0263(5) Uani 1 1 d . . . . .
H19A H 1.4902 0.1747 -0.2416 0.032 Uiso 1 1 calc R . . . .
H19B H 1.5852 0.2766 -0.1976 0.032 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
Cu1 Cu1 2.5226(8) 2_666 ?
Cu1 Cl1 2.3407(7) . ?
Cu1 N3 2.0453(16) 2_666 ?
Cu1 C1 1.9462(19) . ?
Cu1 C1 2.5483(19) 2_666 ?
Cl2 C16 1.7244(19) . ?
Cl3 C19 1.764(2) . ?
Cl4 C19 1.760(2) . ?
N1 C4 1.447(2) . ?
N1 C2 1.391(2) . ?
N1 C1 1.366(2) . ?
N3 Cu1 2.0453(16) 2_666 ?
N3 C18 1.347(2) . ?
N3 C14 1.348(2) . ?
N2 C13 1.467(2) . ?
N2 C1 1.357(2) . ?
N2 C3 1.387(2) . ?
C15 C14 1.382(3) . ?
C15 C16 1.387(3) . ?
C4 C9 1.401(3) . ?
C4 C5 1.400(3) . ?
C18 C17 1.384(3) . ?
C9 C8 1.393(3) . ?
C9 C12 1.501(3) . ?
C14 C13 1.515(2) . ?
C2 C3 1.351(3) . ?
C5 C6 1.395(3) . ?
C5 C10 1.507(3) . ?
C8 C7 1.388(3) . ?
C17 C16 1.385(3) . ?
C7 C6 1.395(3) . ?
C7 C11 1.514(3) . ?
C1 Cu1 2.5483(19) 2_666 ?

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
Cu1 Cu1 C1 45.13(4) 2_666 2_666 ?
Cl1 Cu1 Cu1 132.71(2) . 2_666 ?
Cl1 Cu1 C1 117.25(5) . 2_666 ?
N3 Cu1 Cu1 121.89(5) 2_666 2_666 ?
N3 Cu1 Cl1 98.21(5) 2_666 . ?
N3 Cu1 C1 91.94(6) 2_666 2_666 ?
C1 Cu1 Cu1 68.13(6) . 2_666 ?
C1 Cu1 Cl1 106.24(6) . . ?
C1 Cu1 N3 129.82(7) . 2_666 ?
C1 Cu1 C1 113.27(6) . 2_666 ?
C2 N1 C4 124.16(16) . . ?
C1 N1 C4 122.93(15) . . ?
C1 N1 C2 111.61(15) . . ?
C18 N3 Cu1 118.45(13) . 2_666 ?
C18 N3 C14 117.24(16) . . ?
C14 N3 Cu1 123.92(12) . 2_666 ?
C1 N2 C13 123.54(15) . . ?
C1 N2 C3 112.00(15) . . ?
C3 N2 C13 124.43(15) . . ?
C14 C15 C16 118.40(17) . . ?
C9 C4 N1 119.68(17) . . ?
C5 C4 N1 118.32(16) . . ?
C5 C4 C9 121.97(17) . . ?
N3 C18 C17 123.86(18) . . ?
C4 C9 C12 121.43(18) . . ?
C8 C9 C4 117.39(18) . . ?
C8 C9 C12 121.13(18) . . ?
N3 C14 C15 122.98(17) . . ?
N3 C14 C13 116.47(15) . . ?
C15 C14 C13 120.54(16) . . ?
C3 C2 N1 106.32(17) . . ?
C4 C5 C10 121.17(17) . . ?
C6 C5 C4 118.19(18) . . ?
C6 C5 C10 120.60(18) . . ?
N2 C13 C14 112.38(15) . . ?
C7 C8 C9 122.53(19) . . ?
C18 C17 C16 117.56(18) . . ?
C8 C7 C6 118.38(19) . . ?
C8 C7 C11 121.1(2) . . ?
C6 C7 C11 120.5(2) . . ?
Cu1 C1 Cu1 66.73(6) . 2_666 ?
N1 C1 Cu1 124.04(13) . . ?
N1 C1 Cu1 131.07(13) . 2_666 ?
N2 C1 Cu1 127.81(13) . . ?
N2 C1 Cu1 99.14(11) . 2_666 ?
N2 C1 N1 103.48(15) . . ?
C15 C16 Cl2 120.34(15) . . ?
C17 C16 Cl2 119.78(15) . . ?
C17 C16 C15 119.89(17) . . ?
C5 C6 C7 121.45(19) . . ?
C2 C3 N2 106.59(16) . . ?
Cl4 C19 Cl3 111.19(12) . . ?

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 N3 C18 C17 -170.67(16) 2_666 . . . ?
Cu1 N3 C14 C15 171.43(14) 2_666 . . . ?
Cu1 N3 C14 C13 -7.3(2) 2_666 . . . ?
N1 C4 C9 C8 175.24(16) . . . . ?
N1 C4 C9 C12 -7.2(3) . . . . ?
N1 C4 C5 C6 -177.65(17) . . . . ?
N1 C4 C5 C10 0.2(3) . . . . ?
N1 C2 C3 N2 -0.6(2) . . . . ?
N3 C18 C17 C16 -0.9(3) . . . . ?
N3 C14 C13 N2 -55.2(2) . . . . ?
C15 C14 C13 N2 126.05(18) . . . . ?
C4 N1 C2 C3 167.66(17) . . . . ?
C4 N1 C1 Cu1 77.4(2) . . . 2_666 ?
C4 N1 C1 Cu1 -10.1(2) . . . . ?
C4 N1 C1 N2 -167.44(16) . . . . ?
C4 C9 C8 C7 2.8(3) . . . . ?
C4 C5 C6 C7 2.1(3) . . . . ?
C18 N3 C14 C15 -1.3(3) . . . . ?
C18 N3 C14 C13 179.97(17) . . . . ?
C18 C17 C16 Cl2 178.56(16) . . . . ?
C18 C17 C16 C15 -1.8(3) . . . . ?
C9 C4 C5 C6 0.3(3) . . . . ?
C9 C4 C5 C10 178.12(18) . . . . ?
C9 C8 C7 C6 -0.5(3) . . . . ?
C9 C8 C7 C11 178.60(19) . . . . ?
C14 N3 C18 C17 2.4(3) . . . . ?
C14 C15 C16 Cl2 -177.49(14) . . . . ?
C14 C15 C16 C17 2.9(3) . . . . ?
C2 N1 C4 C9 104.9(2) . . . . ?
C2 N1 C4 C5 -77.1(2) . . . . ?
C2 N1 C1 Cu1 157.31(14) . . . . ?
C2 N1 C1 Cu1 -115.19(17) . . . 2_666 ?
C2 N1 C1 N2 0.0(2) . . . . ?
C5 C4 C9 C8 -2.7(3) . . . . ?
C5 C4 C9 C12 174.87(18) . . . . ?
C13 N2 C1 Cu1 21.6(3) . . . . ?
C13 N2 C1 Cu1 -46.01(18) . . . 2_666 ?
C13 N2 C1 N1 177.70(15) . . . . ?
C13 N2 C3 C2 -177.42(16) . . . . ?
C8 C7 C6 C5 -2.0(3) . . . . ?
C1 N1 C4 C9 -89.2(2) . . . . ?
C1 N1 C4 C5 88.8(2) . . . . ?
C1 N1 C2 C3 0.4(2) . . . . ?
C1 N2 C13 C14 94.5(2) . . . . ?
C1 N2 C3 C2 0.7(2) . . . . ?
C16 C15 C14 N3 -1.3(3) . . . . ?
C16 C15 C14 C13 177.38(17) . . . . ?
C3 N2 C13 C14 -87.6(2) . . . . ?
C3 N2 C1 Cu1 135.88(13) . . . 2_666 ?
C3 N2 C1 Cu1 -156.55(14) . . . . ?
C3 N2 C1 N1 -0.4(2) . . . . ?
C12 C9 C8 C7 -174.75(19) . . . . ?
C10 C5 C6 C7 -175.7(2) . . . . ?
C11 C7 C6 C5 178.8(2) . . . . ?

####################################################################### 
# 
# 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_al008_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1038480'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;
_audit_creation_date             2014-03-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C38 H42 Cl2 Cu2 N6 O2, 2(C H2 Cl2)'
_chemical_formula_sum            'C40 H46 Cl6 Cu2 N6 O2'
_chemical_formula_weight         982.61
_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                   8.292(2)
_cell_length_b                   10.995(3)
_cell_length_c                   12.277(4)
_cell_angle_alpha                84.743(9)
_cell_angle_beta                 86.680(8)
_cell_angle_gamma                78.394(8)
_cell_volume                     1090.9(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7340
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.785
_shelx_estimated_absorpt_T_min   0.652
_exptl_absorpt_coefficient_mu    1.384
_exptl_absorpt_correction_T_max  0.7562
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0550 before and 0.0364 after correction.
The Ratio of minimum to maximum transmission is 0.8951.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.184
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13159
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.764
_diffrn_reflns_theta_min         1.667
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4158
_reflns_number_total             4622
_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       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2008)'
_refine_diff_density_max         1.002
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4622
_refine_ls_number_restraints     204
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.187
_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)+(0.0610P)²+0.6530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1153
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
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
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C2(H2), C3(H3), C17(H17), C8(H8), C6(H6)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C11(H11A,H11B,
 H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.53668(3) 0.51642(3) 0.59734(2) 0.02016(11) Uani 1 1 d . . . . .
Cl1 Cl 0.76574(7) 0.41605(6) 0.69955(5) 0.02363(15) Uani 1 1 d . . . . .
Cl3 Cl 1.66458(10) 0.07170(8) -0.11088(8) 0.0486(2) Uani 1 1 d . . . . .
Cl2 Cl 1.38861(10) 0.26510(8) -0.05227(7) 0.0450(2) Uani 1 1 d . . . . .
O1 O 0.9998(2) 0.34603(19) 0.04204(14) 0.0274(4) Uani 1 1 d . . . . .
N1 N 0.5747(2) 0.76090(18) 0.49350(17) 0.0178(4) Uani 1 1 d . . . . .
N3 N 0.6382(2) 0.46175(18) 0.27922(16) 0.0178(4) Uani 1 1 d . . . . .
N2 N 0.7546(2) 0.61716(18) 0.42473(16) 0.0157(4) Uani 1 1 d . . . . .
C14 C 0.8004(3) 0.4584(2) 0.29138(19) 0.0161(4) Uani 1 1 d . . . . .
C15 C 0.9207(3) 0.4220(2) 0.21198(19) 0.0185(5) Uani 1 1 d . . . . .
H15 H 1.0305 0.4222 0.2233 0.022 Uiso 1 1 calc R . . . .
C4 C 0.4548(3) 0.8191(2) 0.5725(2) 0.0187(5) Uani 1 1 d . . . . .
C1 C 0.6163(3) 0.6345(2) 0.49083(19) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.5086(3) 0.8332(2) 0.6756(2) 0.0226(5) Uani 1 1 d . . . . .
C18 C 0.5973(3) 0.4295(2) 0.1832(2) 0.0229(5) Uani 1 1 d . . . . .
H18 H 0.4861 0.4337 0.1723 0.027 Uiso 1 1 calc R . . . .
C16 C 0.8751(3) 0.3849(2) 0.11441(19) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.6852(3) 0.8203(2) 0.4301(2) 0.0231(5) Uani 1 1 d . . . . .
H2 H 0.6820 0.9056 0.4201 0.028 Uiso 1 1 calc R . . . .
C9 C 0.2891(3) 0.8561(2) 0.5459(2) 0.0227(5) Uani 1 1 d . . . . .
C3 C 0.7982(3) 0.7295(2) 0.3859(2) 0.0217(5) Uani 1 1 d . . . . .
H3 H 0.8873 0.7402 0.3389 0.026 Uiso 1 1 calc R . . . .
C13 C 0.8470(3) 0.4948(2) 0.39927(19) 0.0173(4) Uani 1 1 d . . . . .
H13A H 0.8260 0.4331 0.4572 0.021 Uiso 1 1 calc R . . . .
H13B H 0.9639 0.4956 0.3964 0.021 Uiso 1 1 calc R . . . .
C17 C 0.7088(3) 0.3906(2) 0.0993(2) 0.0232(5) Uani 1 1 d . . . . .
H17 H 0.6736 0.3687 0.0346 0.028 Uiso 1 1 calc R . . . .
C8 C 0.1766(3) 0.9010(2) 0.6285(2) 0.0279(6) Uani 1 1 d . . . . .
H8 H 0.0653 0.9221 0.6136 0.033 Uiso 1 1 calc R . . . .
C6 C 0.3912(4) 0.8831(2) 0.7536(2) 0.0280(6) Uani 1 1 d . . . . .
H6 H 0.4252 0.8952 0.8220 0.034 Uiso 1 1 calc R . . . .
C7 C 0.2244(3) 0.9153(2) 0.7320(2) 0.0301(6) Uani 1 1 d . . . . .
C12 C 0.2359(4) 0.8496(3) 0.4321(3) 0.0358(7) Uani 1 1 d . . . . .
H12A H 0.2797 0.9090 0.3829 0.054 Uiso 1 1 calc GR . . . .
H12B H 0.1178 0.8683 0.4313 0.054 Uiso 1 1 calc GR . . . .
H12C H 0.2762 0.7673 0.4094 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.6870(4) 0.7904(3) 0.7034(2) 0.0313(6) Uani 1 1 d . . . . .
H10A H 0.7216 0.7037 0.6919 0.047 Uiso 1 1 calc GR . . . .
H10B H 0.6996 0.8024 0.7787 0.047 Uiso 1 1 calc GR . . . .
H10C H 0.7535 0.8379 0.6573 0.047 Uiso 1 1 calc GR . . . .
C19 C 0.9527(4) 0.3132(4) -0.0606(2) 0.0405(8) Uani 1 1 d . . . . .
H19A H 1.0490 0.2922 -0.1077 0.061 Uiso 1 1 calc GR . . . .
H19B H 0.8781 0.3826 -0.0948 0.061 Uiso 1 1 calc GR . . . .
H19C H 0.8995 0.2430 -0.0480 0.061 Uiso 1 1 calc GR . . . .
C20 C 1.5227(4) 0.2048(3) -0.1594(3) 0.0383(7) Uani 1 1 d . . . . .
H20A H 1.5818 0.2678 -0.1915 0.046 Uiso 1 1 calc R . . . .
H20B H 1.4591 0.1830 -0.2160 0.046 Uiso 1 1 calc R . . . .
C11 C 0.0982(4) 0.9657(3) 0.8190(3) 0.0477(9) Uani 1 1 d . . . . .
H11A H 0.0320 1.0427 0.7906 0.072 Uiso 1 1 calc GR . . . .
H11B H 0.1536 0.9798 0.8818 0.072 Uiso 1 1 calc GR . . . .
H11C H 0.0290 0.9064 0.8398 0.072 Uiso 1 1 calc GR . . . .


_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 Cu1 2.5744(9) 2_666 ?
Cu1 Cl1 2.3620(8) . ?
Cu1 N3 2.032(2) 2_666 ?
Cu1 C1 1.940(2) . ?
Cl3 C20 1.763(3) . ?
Cl2 C20 1.761(3) . ?
O1 C16 1.352(3) . ?
O1 C19 1.438(3) . ?
N1 C4 1.444(3) . ?
N1 C1 1.366(3) . ?
N1 C2 1.391(3) . ?
N3 Cu1 2.032(2) 2_666 ?
N3 C14 1.354(3) . ?
N3 C18 1.343(3) . ?
N2 C1 1.357(3) . ?
N2 C3 1.392(3) . ?
N2 C13 1.459(3) . ?
C14 C15 1.380(3) . ?
C14 C13 1.511(3) . ?
C15 C16 1.395(3) . ?
C4 C5 1.397(4) . ?
C4 C9 1.401(3) . ?
C5 C6 1.393(4) . ?
C5 C10 1.509(4) . ?
C18 C17 1.382(4) . ?
C16 C17 1.390(4) . ?
C2 C3 1.354(4) . ?
C9 C8 1.393(4) . ?
C9 C12 1.501(4) . ?
C8 C7 1.385(4) . ?
C6 C7 1.391(4) . ?
C7 C11 1.512(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cu1 129.48(3) . 2_666 ?
N3 Cu1 Cu1 121.14(6) 2_666 2_666 ?
N3 Cu1 Cl1 99.21(6) 2_666 . ?
C1 Cu1 Cu1 69.35(7) . 2_666 ?
C1 Cu1 Cl1 106.27(7) . . ?
C1 Cu1 N3 132.34(9) . 2_666 ?
C16 O1 C19 116.0(2) . . ?
C1 N1 C4 122.04(19) . . ?
C1 N1 C2 111.5(2) . . ?
C2 N1 C4 125.0(2) . . ?
C14 N3 Cu1 124.36(16) . 2_666 ?
C18 N3 Cu1 118.40(16) . 2_666 ?
C18 N3 C14 116.4(2) . . ?
C1 N2 C3 111.93(19) . . ?
C1 N2 C13 123.64(19) . . ?
C3 N2 C13 124.4(2) . . ?
N3 C14 C15 123.3(2) . . ?
N3 C14 C13 116.6(2) . . ?
C15 C14 C13 120.1(2) . . ?
C14 C15 C16 119.1(2) . . ?
C5 C4 N1 118.1(2) . . ?
C5 C4 C9 122.0(2) . . ?
C9 C4 N1 119.9(2) . . ?
N1 C1 Cu1 124.26(17) . . ?
N2 C1 Cu1 128.92(17) . . ?
N2 C1 N1 103.68(19) . . ?
C4 C5 C10 121.1(2) . . ?
C6 C5 C4 118.0(2) . . ?
C6 C5 C10 120.8(2) . . ?
N3 C18 C17 124.5(2) . . ?
O1 C16 C15 115.9(2) . . ?
O1 C16 C17 125.6(2) . . ?
C17 C16 C15 118.5(2) . . ?
C3 C2 N1 106.6(2) . . ?
C4 C9 C12 121.1(2) . . ?
C8 C9 C4 117.4(2) . . ?
C8 C9 C12 121.5(2) . . ?
C2 C3 N2 106.3(2) . . ?
N2 C13 C14 111.90(19) . . ?
C18 C17 C16 118.2(2) . . ?
C7 C8 C9 122.4(3) . . ?
C7 C6 C5 121.8(3) . . ?
C8 C7 C6 118.4(2) . . ?
C8 C7 C11 120.6(3) . . ?
C6 C7 C11 121.0(3) . . ?
Cl2 C20 Cl3 110.74(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
Cu1 N3 C14 C15 168.22(18) 2_666 . . . ?
Cu1 N3 C14 C13 -10.6(3) 2_666 . . . ?
Cu1 N3 C18 C17 -168.2(2) 2_666 . . . ?
O1 C16 C17 C18 178.2(2) . . . . ?
N1 C4 C5 C6 -176.6(2) . . . . ?
N1 C4 C5 C10 0.7(3) . . . . ?
N1 C4 C9 C8 174.1(2) . . . . ?
N1 C4 C9 C12 -6.9(4) . . . . ?
N1 C2 C3 N2 -0.8(3) . . . . ?
N3 C14 C15 C16 -0.9(4) . . . . ?
N3 C14 C13 N2 -54.3(3) . . . . ?
N3 C18 C17 C16 -0.5(4) . . . . ?
C14 N3 C18 C17 2.0(4) . . . . ?
C14 C15 C16 O1 -177.6(2) . . . . ?
C14 C15 C16 C17 2.3(4) . . . . ?
C15 C14 C13 N2 126.9(2) . . . . ?
C15 C16 C17 C18 -1.7(4) . . . . ?
C4 N1 C1 Cu1 -5.2(3) . . . . ?
C4 N1 C1 N2 -166.6(2) . . . . ?
C4 N1 C2 C3 166.7(2) . . . . ?
C4 C5 C6 C7 1.7(4) . . . . ?
C4 C9 C8 C7 3.2(4) . . . . ?
C1 N1 C4 C5 85.1(3) . . . . ?
C1 N1 C4 C9 -93.0(3) . . . . ?
C1 N1 C2 C3 0.4(3) . . . . ?
C1 N2 C3 C2 0.9(3) . . . . ?
C1 N2 C13 C14 96.9(3) . . . . ?
C5 C4 C9 C8 -3.8(4) . . . . ?
C5 C4 C9 C12 175.1(2) . . . . ?
C5 C6 C7 C8 -2.3(4) . . . . ?
C5 C6 C7 C11 178.1(3) . . . . ?
C18 N3 C14 C15 -1.3(3) . . . . ?
C18 N3 C14 C13 179.9(2) . . . . ?
C2 N1 C4 C5 -79.8(3) . . . . ?
C2 N1 C4 C9 102.1(3) . . . . ?
C2 N1 C1 Cu1 161.53(18) . . . . ?
C2 N1 C1 N2 0.1(3) . . . . ?
C9 C4 C5 C6 1.5(4) . . . . ?
C9 C4 C5 C10 178.8(2) . . . . ?
C9 C8 C7 C6 -0.2(4) . . . . ?
C9 C8 C7 C11 179.4(3) . . . . ?
C3 N2 C1 Cu1 -160.83(18) . . . . ?
C3 N2 C1 N1 -0.6(3) . . . . ?
C3 N2 C13 C14 -84.1(3) . . . . ?
C13 N2 C1 Cu1 18.3(3) . . . . ?
C13 N2 C1 N1 178.6(2) . . . . ?
C13 N2 C3 C2 -178.3(2) . . . . ?
C13 C14 C15 C16 177.9(2) . . . . ?
C12 C9 C8 C7 -175.7(2) . . . . ?
C10 C5 C6 C7 -175.6(3) . . . . ?
C19 O1 C16 C15 -177.2(2) . . . . ?
C19 O1 C16 C17 2.8(4) . . . . ?

####################################################################### 
# 
# 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_al009_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1038481'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;
_audit_creation_date             2014-03-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C18 H18 Cl Cu N4 O2)'
_chemical_formula_sum            'C36 H36 Cl2 Cu2 N8 O4'
_chemical_formula_weight         842.71
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   9.0636(13)
_cell_length_b                   9.6375(13)
_cell_length_c                   20.925(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1827.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.595
_exptl_absorpt_coefficient_mu    1.361
_exptl_absorpt_correction_T_max  0.7784
_exptl_absorpt_correction_T_min  0.7278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0566 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.9350.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.118
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22052
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.736
_diffrn_reflns_theta_min         2.327
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3692
_reflns_number_total             3874
_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       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 
;
 Flack x determined using 1532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.061(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     204
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0228
_refine_ls_restrained_S_all      1.037
_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)+(0.0383P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0605
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
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
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C17(H17), C15(H15), C2(H2), C8(H8), C6(H6)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.40255(3) 0.91323(3) 0.60722(2) 0.01821(10) Uani 1 1 d . . . . .
Cl1 Cl 0.61478(7) 0.92813(7) 0.56500(3) 0.02292(14) Uani 1 1 d . . . . .
N2 N 0.0806(2) 0.8946(2) 0.61324(9) 0.0177(4) Uani 1 1 d . . . . .
O1 O 0.5253(2) 1.1248(2) 0.36819(9) 0.0291(5) Uani 1 1 d . . . . .
O2 O 0.4803(2) 0.9059(2) 0.37746(9) 0.0312(5) Uani 1 1 d . . . . .
N3 N 0.1199(3) 1.1175(2) 0.52422(10) 0.0220(5) Uani 1 1 d . . . . .
N1 N 0.1742(2) 0.9213(3) 0.70589(10) 0.0172(4) Uani 1 1 d . . . . .
N4 N 0.4576(2) 1.0262(2) 0.39133(11) 0.0212(5) Uani 1 1 d . . . . .
C3 C -0.0363(3) 0.9053(3) 0.65510(12) 0.0217(5) Uani 1 1 d . . . . .
H3 H -0.1361 0.9018 0.6449 0.026 Uiso 1 1 calc R . . . .
C16 C 0.3406(3) 1.0579(3) 0.43847(11) 0.0175(5) Uani 1 1 d . . . . .
C18 C 0.1991(3) 1.2179(3) 0.49684(13) 0.0234(6) Uani 1 1 d . . . . .
H18 H 0.1761 1.3093 0.5070 0.028 Uiso 1 1 calc R . . . .
C17 C 0.3136(3) 1.1946(3) 0.45412(12) 0.0204(6) Uani 1 1 d . . . . .
H17 H 0.3689 1.2669 0.4370 0.025 Uiso 1 1 calc R . . . .
C14 C 0.1529(3) 0.9861(3) 0.50925(12) 0.0182(5) Uani 1 1 d . . . . .
C5 C 0.3280(3) 1.0790(3) 0.76720(12) 0.0194(5) Uani 1 1 d . . . . .
C15 C 0.2614(3) 0.9506(3) 0.46507(11) 0.0172(5) Uani 1 1 d . . . . .
H15 H 0.2795 0.8587 0.4540 0.021 Uiso 1 1 calc R . . . .
C1 C 0.2115(3) 0.9054(3) 0.64336(11) 0.0168(5) Uani 1 1 d . . . . .
C4 C 0.2799(3) 0.9427(3) 0.75618(11) 0.0172(5) Uani 1 1 d . . . . .
C13 C 0.0652(3) 0.8764(3) 0.54372(12) 0.0207(6) Uani 1 1 d . . . . .
H13A H -0.0379 0.8834 0.5318 0.025 Uiso 1 1 calc R . . . .
H13B H 0.1004 0.7851 0.5315 0.025 Uiso 1 1 calc R . . . .
C2 C 0.0222(3) 0.9219(3) 0.71363(12) 0.0214(5) Uani 1 1 d . . . . .
H2 H -0.0292 0.9318 0.7518 0.026 Uiso 1 1 calc R . . . .
C9 C 0.3301(3) 0.8301(3) 0.79156(13) 0.0213(6) Uani 1 1 d . . . . .
C10 C 0.2615(3) 1.1982(3) 0.73099(14) 0.0269(6) Uani 1 1 d . . . . .
H10A H 0.2810 1.1870 0.6862 0.040 Uiso 1 1 calc GR . . . .
H10B H 0.3042 1.2836 0.7456 0.040 Uiso 1 1 calc GR . . . .
H10C H 0.1569 1.2000 0.7380 0.040 Uiso 1 1 calc GR . . . .
C8 C 0.4389(3) 0.8550(3) 0.83734(13) 0.0250(6) Uani 1 1 d . . . . .
H8 H 0.4751 0.7811 0.8613 0.030 Uiso 1 1 calc R . . . .
C6 C 0.4362(3) 1.0975(3) 0.81405(12) 0.0233(6) Uani 1 1 d . . . . .
H6 H 0.4699 1.1868 0.8226 0.028 Uiso 1 1 calc R . . . .
C12 C 0.2660(3) 0.6872(3) 0.78202(15) 0.0290(7) Uani 1 1 d . . . . .
H12A H 0.1675 0.6846 0.7989 0.043 Uiso 1 1 calc GR . . . .
H12B H 0.3259 0.6202 0.8039 0.043 Uiso 1 1 calc GR . . . .
H12C H 0.2637 0.6659 0.7372 0.043 Uiso 1 1 calc GR . . . .
C7 C 0.4946(3) 0.9876(3) 0.84804(13) 0.0249(6) Uani 1 1 d . . . . .
C11 C 0.6190(3) 1.0111(4) 0.89506(14) 0.0366(7) Uani 1 1 d . . . . .
H11A H 0.6162 0.9406 0.9275 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.6081 1.1007 0.9145 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.7118 1.0068 0.8730 0.055 Uiso 1 1 calc GR . . . .


_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 Cl1 2.1215(7) . ?
Cu1 C1 1.891(2) . ?
N2 C3 1.379(3) . ?
N2 C1 1.348(3) . ?
N2 C13 1.472(3) . ?
O1 N4 1.231(3) . ?
O2 N4 1.213(3) . ?
N3 C18 1.334(4) . ?
N3 C14 1.339(3) . ?
N1 C1 1.360(3) . ?
N1 C4 1.438(3) . ?
N1 C2 1.387(3) . ?
N4 C16 1.480(3) . ?
C3 C2 1.344(4) . ?
C16 C17 1.379(4) . ?
C16 C15 1.376(4) . ?
C18 C17 1.388(4) . ?
C14 C15 1.392(4) . ?
C14 C13 1.506(4) . ?
C5 C4 1.403(4) . ?
C5 C10 1.502(4) . ?
C5 C6 1.398(4) . ?
C4 C9 1.390(4) . ?
C9 C8 1.396(4) . ?
C9 C12 1.508(4) . ?
C8 C7 1.392(4) . ?
C6 C7 1.382(4) . ?
C7 C11 1.514(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Cu1 Cl1 178.08(9) . . ?
C3 N2 C13 124.4(2) . . ?
C1 N2 C3 111.96(19) . . ?
C1 N2 C13 123.7(2) . . ?
C18 N3 C14 117.7(2) . . ?
C1 N1 C4 123.7(2) . . ?
C1 N1 C2 111.1(2) . . ?
C2 N1 C4 125.1(2) . . ?
O1 N4 C16 117.4(2) . . ?
O2 N4 O1 124.0(2) . . ?
O2 N4 C16 118.6(2) . . ?
C2 C3 N2 106.5(2) . . ?
C17 C16 N4 118.8(2) . . ?
C15 C16 N4 119.2(2) . . ?
C15 C16 C17 122.0(2) . . ?
N3 C18 C17 124.2(2) . . ?
C16 C17 C18 116.1(2) . . ?
N3 C14 C15 123.1(2) . . ?
N3 C14 C13 115.7(2) . . ?
C15 C14 C13 121.2(2) . . ?
C4 C5 C10 120.6(2) . . ?
C6 C5 C4 116.9(2) . . ?
C6 C5 C10 122.5(3) . . ?
C16 C15 C14 116.9(2) . . ?
N2 C1 Cu1 128.49(17) . . ?
N2 C1 N1 103.8(2) . . ?
N1 C1 Cu1 127.46(18) . . ?
C5 C4 N1 117.5(2) . . ?
C9 C4 N1 119.7(2) . . ?
C9 C4 C5 122.8(2) . . ?
N2 C13 C14 109.9(2) . . ?
C3 C2 N1 106.6(2) . . ?
C4 C9 C8 117.6(3) . . ?
C4 C9 C12 121.1(3) . . ?
C8 C9 C12 121.3(3) . . ?
C7 C8 C9 121.6(3) . . ?
C7 C6 C5 122.1(3) . . ?
C8 C7 C11 120.8(3) . . ?
C6 C7 C8 118.8(3) . . ?
C6 C7 C11 120.4(3) . . ?

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 C3 C2 N1 0.2(4) . . . . ?
O1 N4 C16 C17 -0.1(4) . . . . ?
O1 N4 C16 C15 179.5(2) . . . . ?
O2 N4 C16 C17 -179.6(2) . . . . ?
O2 N4 C16 C15 0.0(4) . . . . ?
N3 C18 C17 C16 2.3(4) . . . . ?
N3 C14 C15 C16 2.9(4) . . . . ?
N3 C14 C13 N2 -56.3(3) . . . . ?
N1 C4 C9 C8 176.4(2) . . . . ?
N1 C4 C9 C12 -5.3(4) . . . . ?
N4 C16 C17 C18 177.8(2) . . . . ?
N4 C16 C15 C14 179.8(2) . . . . ?
C3 N2 C1 Cu1 -174.2(2) . . . . ?
C3 N2 C1 N1 0.8(3) . . . . ?
C3 N2 C13 C14 126.9(3) . . . . ?
C18 N3 C14 C15 -2.4(4) . . . . ?
C18 N3 C14 C13 177.2(2) . . . . ?
C17 C16 C15 C14 -0.6(4) . . . . ?
C14 N3 C18 C17 -0.3(4) . . . . ?
C5 C4 C9 C8 -3.6(4) . . . . ?
C5 C4 C9 C12 174.7(2) . . . . ?
C5 C6 C7 C8 -3.0(4) . . . . ?
C5 C6 C7 C11 175.7(2) . . . . ?
C15 C16 C17 C18 -1.8(4) . . . . ?
C15 C14 C13 N2 123.4(3) . . . . ?
C1 N2 C3 C2 -0.7(3) . . . . ?
C1 N2 C13 C14 -51.9(3) . . . . ?
C1 N1 C4 C5 84.6(3) . . . . ?
C1 N1 C4 C9 -95.4(3) . . . . ?
C1 N1 C2 C3 0.4(4) . . . . ?
C4 N1 C1 Cu1 -2.3(4) . . . . ?
C4 N1 C1 N2 -177.3(2) . . . . ?
C4 N1 C2 C3 176.9(2) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C4 C9 C8 C7 0.8(4) . . . . ?
C13 N2 C3 C2 -179.5(2) . . . . ?
C13 N2 C1 Cu1 4.7(4) . . . . ?
C13 N2 C1 N1 179.7(2) . . . . ?
C13 C14 C15 C16 -176.8(2) . . . . ?
C2 N1 C1 Cu1 174.3(2) . . . . ?
C2 N1 C1 N2 -0.7(3) . . . . ?
C2 N1 C4 C5 -91.5(3) . . . . ?
C2 N1 C4 C9 88.5(4) . . . . ?
C9 C8 C7 C6 2.5(4) . . . . ?
C9 C8 C7 C11 -176.3(3) . . . . ?
C10 C5 C4 N1 4.7(3) . . . . ?
C10 C5 C4 C9 -175.2(3) . . . . ?
C10 C5 C6 C7 178.6(3) . . . . ?
C6 C5 C4 N1 -176.9(2) . . . . ?
C6 C5 C4 C9 3.1(4) . . . . ?
C12 C9 C8 C7 -177.5(3) . . . . ?

####################################################################### 
# 
# 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_al059_0m
_database_code_depnum_ccdc_archive 'CCDC 1038482'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;
_audit_creation_date             2014-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H25 Cl Cu N3'
_chemical_formula_sum            'C21 H25 Cl Cu N3'
_chemical_formula_weight         418.43
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5545(5)
_cell_length_b                   8.8034(5)
_cell_length_c                   23.9329(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.6239(16)
_cell_angle_gamma                90
_cell_volume                     1999.61(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8734
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.61
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.880
_shelx_estimated_absorpt_T_min   0.759
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0683 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.9110.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.106
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26675
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.775
_diffrn_reflns_theta_min         1.713
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3800
_reflns_number_total             4269
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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., 2013)'
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+1.6917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
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
2.a Ternary CH refined with riding coordinates:
 C13(H13), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C3(H3), C7(H7), C2(H2), C8(H8), C19(H19), C6(H6), C18(H18), C20(H20)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C)
;
_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
Cu1 Cu 0.48586(2) 0.06513(3) 0.33637(2) 0.01540(8) Uani 1 1 d . . . . .
Cl1 Cl 0.26873(5) -0.03623(6) 0.32639(2) 0.02522(12) Uani 1 1 d . . . . .
N1 N 0.79271(15) 0.02843(17) 0.36354(6) 0.0132(3) Uani 1 1 d . . . . .
N3 N 0.55794(16) -0.20858(17) 0.15148(6) 0.0153(3) Uani 1 1 d . . . . .
C1 C 0.67060(19) -0.0115(2) 0.33206(7) 0.0135(3) Uani 1 1 d . . . . .
N2 N 0.71378(16) -0.10871(17) 0.29340(6) 0.0147(3) Uani 1 1 d . . . . .
C21 C 0.5424(2) -0.1530(2) 0.09896(8) 0.0192(4) Uani 1 1 d . . . . .
H21 H 0.5038 -0.2173 0.0692 0.023 Uiso 1 1 calc R . . . .
C3 C 0.8587(2) -0.1273(2) 0.30039(8) 0.0180(4) Uani 1 1 d . . . . .
H3 H 0.9123 -0.1889 0.2782 0.022 Uiso 1 1 calc R . . . .
C16 C 0.6177(2) -0.1854(2) 0.25100(7) 0.0183(4) Uani 1 1 d . . . . .
H16A H 0.5222 -0.1849 0.2632 0.022 Uiso 1 1 calc R . . . .
H16B H 0.6476 -0.2926 0.2486 0.022 Uiso 1 1 calc R . . . .
C15 C 0.8275(2) -0.1778(2) 0.52487(9) 0.0256(4) Uani 1 1 d . . . . .
H15A H 0.9279 -0.1516 0.5297 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.8170 -0.2886 0.5244 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.7822 -0.1356 0.5561 0.038 Uiso 1 1 calc GR . . . .
C9 C 0.78178(19) 0.0578(2) 0.46432(8) 0.0164(4) Uani 1 1 d . . . . .
C7 C 0.8162(2) 0.3075(2) 0.50598(8) 0.0218(4) Uani 1 1 d . . . . .
H7 H 0.8224 0.3706 0.5384 0.026 Uiso 1 1 calc R . . . .
C2 C 0.90890(19) -0.0417(2) 0.34460(8) 0.0176(4) Uani 1 1 d . . . . .
H2 H 1.0046 -0.0311 0.3599 0.021 Uiso 1 1 calc R . . . .
C13 C 0.7584(2) -0.1121(2) 0.46962(8) 0.0256(5) Uani 1 1 d . . . . .
H13 H 0.8017 -0.1631 0.4385 0.031 Uiso 1 1 calc R . . . .
C5 C 0.82474(19) 0.2805(2) 0.40608(8) 0.0167(4) Uani 1 1 d . . . . .
C8 C 0.7900(2) 0.1533(2) 0.51106(8) 0.0201(4) Uani 1 1 d . . . . .
H8 H 0.7775 0.1124 0.5469 0.024 Uiso 1 1 calc R . . . .
C19 C 0.6333(2) 0.0892(2) 0.12930(8) 0.0216(4) Uani 1 1 d . . . . .
H19 H 0.6591 0.1906 0.1216 0.026 Uiso 1 1 calc R . . . .
C6 C 0.8334(2) 0.3700(2) 0.45442(8) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.8514 0.4758 0.4518 0.025 Uiso 1 1 calc R . . . .
C4 C 0.79874(18) 0.1255(2) 0.41223(7) 0.0137(4) Uani 1 1 d . . . . .
C11 C 0.7735(2) 0.5014(3) 0.33878(10) 0.0317(5) Uani 1 1 d . . . . .
H11A H 0.6744 0.4908 0.3451 0.048 Uiso 1 1 calc GR . . . .
H11B H 0.7790 0.5324 0.2998 0.048 Uiso 1 1 calc GR . . . .
H11C H 0.8187 0.5785 0.3643 0.048 Uiso 1 1 calc GR . . . .
C17 C 0.61025(18) -0.1153(2) 0.19342(7) 0.0149(4) Uani 1 1 d . . . . .
C10 C 0.8489(2) 0.3493(2) 0.34989(8) 0.0231(4) Uani 1 1 d . . . . .
H10 H 0.8106 0.2770 0.3197 0.028 Uiso 1 1 calc R . . . .
C18 C 0.6483(2) 0.0340(2) 0.18381(8) 0.0176(4) Uani 1 1 d . . . . .
H18 H 0.6842 0.0974 0.2143 0.021 Uiso 1 1 calc R . . . .
C20 C 0.5797(2) -0.0069(2) 0.08619(8) 0.0223(4) Uani 1 1 d . . . . .
H20 H 0.5689 0.0274 0.0483 0.027 Uiso 1 1 calc R . . . .
C12 C 1.0061(2) 0.3690(3) 0.34569(10) 0.0366(6) Uani 1 1 d . . . . .
H12A H 1.0474 0.4351 0.3762 0.055 Uiso 1 1 calc GR . . . .
H12B H 1.0193 0.4151 0.3094 0.055 Uiso 1 1 calc GR . . . .
H12C H 1.0525 0.2696 0.3488 0.055 Uiso 1 1 calc GR . . . .
C14 C 0.6023(3) -0.1523(4) 0.46289(12) 0.0676(11) Uani 1 1 d . . . . .
H14A H 0.5915 -0.2630 0.4630 0.101 Uiso 1 1 calc GR . . . .
H14B H 0.5572 -0.1113 0.4272 0.101 Uiso 1 1 calc GR . . . .
H14C H 0.5579 -0.1085 0.4941 0.101 Uiso 1 1 calc GR . . . .


_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 Cl1 2.2456(5) . ?
Cu1 N3 2.0631(16) 2_655 ?
Cu1 C1 1.9036(18) . ?
N1 C1 1.360(2) . ?
N1 C2 1.391(2) . ?
N1 C4 1.441(2) . ?
N3 Cu1 2.0630(16) 2_645 ?
N3 C21 1.341(2) . ?
N3 C17 1.348(2) . ?
C1 N2 1.359(2) . ?
N2 C3 1.385(2) . ?
N2 C16 1.453(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.379(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.342(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.504(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C13 1.522(3) . ?
C9 C13 1.520(3) . ?
C9 C8 1.395(3) . ?
C9 C4 1.408(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(3) . ?
C7 C6 1.378(3) . ?
C2 H2 0.9500 . ?
C13 H13 1.0000 . ?
C13 C14 1.523(3) . ?
C5 C6 1.394(3) . ?
C5 C4 1.398(3) . ?
C5 C10 1.517(3) . ?
C8 H8 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.384(3) . ?
C19 C20 1.386(3) . ?
C6 H6 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C10 1.529(3) . ?
C17 C18 1.390(3) . ?
C10 H10 1.0000 . ?
C10 C12 1.527(3) . ?
C18 H18 0.9500 . ?
C20 H20 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N3 Cu1 Cl1 101.46(4) 2_655 . ?
C1 Cu1 Cl1 134.78(6) . . ?
C1 Cu1 N3 123.67(7) . 2_655 ?
C1 N1 C2 111.75(15) . . ?
C1 N1 C4 123.58(15) . . ?
C2 N1 C4 124.60(15) . . ?
C21 N3 Cu1 118.81(12) . 2_645 ?
C21 N3 C17 117.86(16) . . ?
C17 N3 Cu1 123.19(12) . 2_645 ?
N1 C1 Cu1 128.30(13) . . ?
N2 C1 Cu1 128.06(13) . . ?
N2 C1 N1 103.39(15) . . ?
C1 N2 C3 111.73(15) . . ?
C1 N2 C16 123.43(15) . . ?
C3 N2 C16 124.83(16) . . ?
N3 C21 H21 118.5 . . ?
N3 C21 C20 122.99(17) . . ?
C20 C21 H21 118.5 . . ?
N2 C3 H3 126.6 . . ?
C2 C3 N2 106.85(16) . . ?
C2 C3 H3 126.6 . . ?
N2 C16 H16A 108.7 . . ?
N2 C16 H16B 108.7 . . ?
N2 C16 C17 114.12(15) . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
C8 C9 C13 121.46(17) . . ?
C8 C9 C4 116.96(17) . . ?
C4 C9 C13 121.57(16) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.70(18) . . ?
N1 C2 H2 126.9 . . ?
C3 C2 N1 106.28(16) . . ?
C3 C2 H2 126.9 . . ?
C15 C13 H13 107.6 . . ?
C15 C13 C14 108.98(17) . . ?
C9 C13 C15 113.14(16) . . ?
C9 C13 H13 107.6 . . ?
C9 C13 C14 111.8(2) . . ?
C14 C13 H13 107.6 . . ?
C6 C5 C4 117.30(17) . . ?
C6 C5 C10 120.62(17) . . ?
C4 C5 C10 122.03(17) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 C9 120.89(18) . . ?
C7 C8 H8 119.6 . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.48(18) . . ?
C20 C19 H19 120.8 . . ?
C7 C6 C5 121.01(19) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C9 C4 N1 117.86(16) . . ?
C5 C4 N1 119.00(16) . . ?
C5 C4 C9 123.12(17) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
N3 C17 C16 113.99(16) . . ?
N3 C17 C18 122.32(16) . . ?
C18 C17 C16 123.64(16) . . ?
C5 C10 C11 112.78(17) . . ?
C5 C10 H10 107.8 . . ?
C5 C10 C12 110.80(16) . . ?
C11 C10 H10 107.8 . . ?
C12 C10 C11 109.66(18) . . ?
C12 C10 H10 107.8 . . ?
C19 C18 C17 119.16(17) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C21 C20 C19 119.16(18) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Cu1 N3 C21 C20 -174.63(15) 2_645 . . . ?
Cu1 N3 C17 C16 -6.9(2) 2_645 . . . ?
Cu1 N3 C17 C18 175.40(13) 2_645 . . . ?
Cu1 C1 N2 C3 174.01(13) . . . . ?
Cu1 C1 N2 C16 -7.3(3) . . . . ?
N1 C1 N2 C3 -0.5(2) . . . . ?
N1 C1 N2 C16 178.15(15) . . . . ?
N3 C21 C20 C19 -1.4(3) . . . . ?
N3 C17 C18 C19 -0.5(3) . . . . ?
C1 N1 C2 C3 0.0(2) . . . . ?
C1 N1 C4 C9 85.6(2) . . . . ?
C1 N1 C4 C5 -96.1(2) . . . . ?
C1 N2 C3 C2 0.6(2) . . . . ?
C1 N2 C16 C17 101.7(2) . . . . ?
N2 C3 C2 N1 -0.3(2) . . . . ?
N2 C16 C17 N3 160.69(15) . . . . ?
N2 C16 C17 C18 -21.7(3) . . . . ?
C21 N3 C17 C16 177.39(16) . . . . ?
C21 N3 C17 C18 -0.3(3) . . . . ?
C3 N2 C16 C17 -79.8(2) . . . . ?
C16 N2 C3 C2 -178.11(16) . . . . ?
C16 C17 C18 C19 -177.96(18) . . . . ?
C2 N1 C1 Cu1 -174.20(13) . . . . ?
C2 N1 C1 N2 0.34(19) . . . . ?
C2 N1 C4 C9 -91.0(2) . . . . ?
C2 N1 C4 C5 87.3(2) . . . . ?
C13 C9 C8 C7 177.77(18) . . . . ?
C13 C9 C4 N1 0.2(3) . . . . ?
C13 C9 C4 C5 -177.97(18) . . . . ?
C8 C9 C13 C15 -33.9(3) . . . . ?
C8 C9 C13 C14 89.7(2) . . . . ?
C8 C9 C4 N1 179.08(15) . . . . ?
C8 C9 C4 C5 0.9(3) . . . . ?
C8 C7 C6 C5 0.1(3) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C6 C5 C4 N1 -178.39(16) . . . . ?
C6 C5 C4 C9 -0.2(3) . . . . ?
C6 C5 C10 C11 -44.5(3) . . . . ?
C6 C5 C10 C12 78.9(2) . . . . ?
C4 N1 C1 Cu1 8.8(3) . . . . ?
C4 N1 C1 N2 -176.67(15) . . . . ?
C4 N1 C2 C3 176.97(16) . . . . ?
C4 C9 C13 C15 144.94(18) . . . . ?
C4 C9 C13 C14 -91.6(2) . . . . ?
C4 C9 C8 C7 -1.1(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C4 C5 C10 C11 138.11(19) . . . . ?
C4 C5 C10 C12 -98.5(2) . . . . ?
C17 N3 C21 C20 1.2(3) . . . . ?
C10 C5 C6 C7 -177.83(18) . . . . ?
C10 C5 C4 N1 -0.9(3) . . . . ?
C10 C5 C4 C9 177.30(17) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C20 C19 C18 C17 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ae161_a
_database_code_depnum_ccdc_archive 'CCDC 1431818'
_audit_update_record             
;
2015-10-18 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H38 Cl2 Cu2 N6'
_chemical_formula_sum            'C36 H38 Cl2 Cu2 N6'
_chemical_formula_weight         752.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.0169(4)
_cell_length_b                   15.9690(6)
_cell_length_c                   10.7209(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.0560(10)
_cell_angle_gamma                90
_cell_volume                     1708.24(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8772
_cell_measurement_theta_min      2.294
_cell_measurement_theta_max      26.036

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    1.437
_shelx_estimated_absorpt_T_min   0.393
_shelx_estimated_absorpt_T_max   0.641
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12547
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         26.044
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3371
_reflns_number_gt                3169
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²+1.0073P] 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         3371
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0532
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Cu1 Cu 0.42798(2) 0.46358(2) 0.85622(2) 0.01524(7) Uani 1 1 d . . . . .
N1 N 0.39446(12) 0.32080(7) 0.68336(11) 0.0133(2) Uani 1 1 d . . . . .
C1 C 0.35148(14) 0.36540(9) 0.78051(13) 0.0130(3) Uani 1 1 d . . . . .
Cl1 Cl 0.49417(3) 0.59002(2) 0.89837(3) 0.01588(8) Uani 1 1 d . . . . .
C3 C 0.21073(14) 0.25724(9) 0.72725(13) 0.0154(3) Uani 1 1 d . . . . .
H3 H 0.1364 0.2203 0.7274 0.018 Uiso 1 1 calc R U . . .
N3 N -0.06356(12) 0.39023(8) 0.94525(11) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.30962(14) 0.25410(9) 0.65013(13) 0.0156(3) Uani 1 1 d . . . . .
H2 H 0.3194 0.2142 0.5858 0.019 Uiso 1 1 calc R U . . .
N2 N 0.23828(11) 0.32478(7) 0.80640(11) 0.0135(2) Uani 1 1 d . . . . .
C4 C 0.51807(14) 0.33648(9) 0.62818(13) 0.0137(3) Uani 1 1 d . . . . .
C5 C 0.63743(15) 0.30956(9) 0.69260(13) 0.0153(3) Uani 1 1 d . . . . .
C6 C 0.75603(15) 0.32309(10) 0.63730(14) 0.0192(3) Uani 1 1 d . . . . .
H00K H 0.8384 0.3053 0.6798 0.023 Uiso 1 1 calc R U . . .
C7 C 0.75721(16) 0.36197(10) 0.52155(14) 0.0206(3) Uani 1 1 d . . . . .
C8 C 0.63628(16) 0.38712(9) 0.45966(14) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.6364 0.4131 0.3799 0.024 Uiso 1 1 calc R U . . .
C9 C 0.51463(15) 0.37534(9) 0.51137(13) 0.0168(3) Uani 1 1 d . . . . .
C10 C 0.63862(16) 0.26616(10) 0.81732(14) 0.0213(3) Uani 1 1 d . . . . .
H00F H 0.5917 0.2124 0.8067 0.032 Uiso 1 1 calc R U . . .
H10 H 0.5935 0.3014 0.8755 0.032 Uiso 1 1 calc R U . . .
H00J H 0.7315 0.2564 0.8510 0.032 Uiso 1 1 calc R U . . .
C11 C 0.88732(18) 0.37743(13) 0.46442(17) 0.0325(4) Uani 1 1 d . . . . .
H00P H 0.8740 0.3688 0.3737 0.049 Uiso 1 1 calc R U . . .
H00Q H 0.9556 0.3384 0.5006 0.049 Uiso 1 1 calc R U . . .
H00R H 0.9168 0.4351 0.4819 0.049 Uiso 1 1 calc R U . . .
C12 C 0.38578(17) 0.40389(10) 0.44105(15) 0.0242(3) Uani 1 1 d . . . . .
H12 H 0.3589 0.3636 0.3746 0.036 Uiso 1 1 calc R U . . .
H00N H 0.3991 0.4590 0.4040 0.036 Uiso 1 1 calc R U . . .
H00O H 0.3155 0.4076 0.4989 0.036 Uiso 1 1 calc R U . . .
C13 C 0.15904(14) 0.34654(9) 0.91016(13) 0.0151(3) Uani 1 1 d . . . . .
H00B H 0.2176 0.3761 0.9751 0.018 Uiso 1 1 calc R U . . .
H13 H 0.1282 0.2942 0.9479 0.018 Uiso 1 1 calc R U . . .
C14 C 0.03826(14) 0.40088(9) 0.87349(13) 0.0131(3) Uani 1 1 d . . . . .
C15 C 0.03594(15) 0.45942(9) 0.77776(14) 0.0169(3) Uani 1 1 d . . . . .
H15 H 0.1097 0.4649 0.7284 0.020 Uiso 1 1 calc R U . . .
C16 C -0.07634(15) 0.50979(10) 0.75570(14) 0.0194(3) Uani 1 1 d . . . . .
H00L H -0.0810 0.5501 0.6903 0.023 Uiso 1 1 calc R U . . .
C17 C -0.18132(15) 0.50072(10) 0.82978(14) 0.0186(3) Uani 1 1 d . . . . .
H17 H -0.2589 0.5350 0.8172 0.022 Uiso 1 1 calc R U . . .
C18 C -0.17069(15) 0.44047(10) 0.92271(14) 0.0186(3) Uani 1 1 d . . . . .
H18 H -0.2431 0.4342 0.9735 0.022 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
Cu1 C1 1.8960(14) . ?
Cu1 Cl1 2.1604(4) . ?
N1 C1 1.3625(18) . ?
N1 C2 1.3894(18) . ?
N1 C4 1.4404(18) . ?
C1 N2 1.3561(18) . ?
C3 C2 1.346(2) . ?
C3 N2 1.3850(19) . ?
C3 H3 0.9500 . ?
N3 C14 1.3413(18) . ?
N3 C18 1.3446(19) . ?
C2 H2 0.9500 . ?
N2 C13 1.4641(17) . ?
C4 C5 1.395(2) . ?
C4 C9 1.395(2) . ?
C5 C6 1.391(2) . ?
C5 C10 1.505(2) . ?
C6 C7 1.389(2) . ?
C6 H00K 0.9500 . ?
C7 C8 1.388(2) . ?
C7 C11 1.508(2) . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C9 C12 1.507(2) . ?
C10 H00F 0.9800 . ?
C10 H10 0.9800 . ?
C10 H00J 0.9800 . ?
C11 H00P 0.9800 . ?
C11 H00Q 0.9800 . ?
C11 H00R 0.9800 . ?
C12 H12 0.9800 . ?
C12 H00N 0.9800 . ?
C12 H00O 0.9800 . ?
C13 C14 1.5125(19) . ?
C13 H00B 0.9900 . ?
C13 H13 0.9900 . ?
C14 C15 1.387(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H00L 0.9500 . ?
C17 C18 1.382(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Cu1 Cl1 165.32(4) . . ?
C1 N1 C2 111.68(12) . . ?
C1 N1 C4 124.34(12) . . ?
C2 N1 C4 123.81(12) . . ?
N2 C1 N1 103.46(12) . . ?
N2 C1 Cu1 128.43(10) . . ?
N1 C1 Cu1 128.06(10) . . ?
C2 C3 N2 106.72(12) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
C14 N3 C18 117.16(13) . . ?
C3 C2 N1 106.29(12) . . ?
C3 C2 H2 126.9 . . ?
N1 C2 H2 126.9 . . ?
C1 N2 C3 111.84(11) . . ?
C1 N2 C13 124.13(12) . . ?
C3 N2 C13 123.93(12) . . ?
C5 C4 C9 122.26(13) . . ?
C5 C4 N1 118.26(13) . . ?
C9 C4 N1 119.45(13) . . ?
C6 C5 C4 117.92(13) . . ?
C6 C5 C10 120.67(14) . . ?
C4 C5 C10 121.40(13) . . ?
C7 C6 C5 121.69(14) . . ?
C7 C6 H00K 119.2 . . ?
C5 C6 H00K 119.2 . . ?
C8 C7 C6 118.73(14) . . ?
C8 C7 C11 120.48(15) . . ?
C6 C7 C11 120.78(15) . . ?
C7 C8 C9 121.80(14) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C4 C9 C8 117.59(14) . . ?
C4 C9 C12 122.41(14) . . ?
C8 C9 C12 119.99(14) . . ?
C5 C10 H00F 109.5 . . ?
C5 C10 H10 109.5 . . ?
H00F C10 H10 109.5 . . ?
C5 C10 H00J 109.5 . . ?
H00F C10 H00J 109.5 . . ?
H10 C10 H00J 109.5 . . ?
C7 C11 H00P 109.5 . . ?
C7 C11 H00Q 109.5 . . ?
H00P C11 H00Q 109.5 . . ?
C7 C11 H00R 109.5 . . ?
H00P C11 H00R 109.5 . . ?
H00Q C11 H00R 109.5 . . ?
C9 C12 H12 109.5 . . ?
C9 C12 H00N 109.5 . . ?
H12 C12 H00N 109.5 . . ?
C9 C12 H00O 109.5 . . ?
H12 C12 H00O 109.5 . . ?
H00N C12 H00O 109.5 . . ?
N2 C13 C14 114.43(11) . . ?
N2 C13 H00B 108.7 . . ?
C14 C13 H00B 108.7 . . ?
N2 C13 H13 108.7 . . ?
C14 C13 H13 108.7 . . ?
H00B C13 H13 107.6 . . ?
N3 C14 C15 123.09(13) . . ?
N3 C14 C13 114.17(12) . . ?
C15 C14 C13 122.68(13) . . ?
C16 C15 C14 118.55(14) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C17 C16 C15 119.27(14) . . ?
C17 C16 H00L 120.4 . . ?
C15 C16 H00L 120.4 . . ?
C16 C17 C18 118.27(14) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
N3 C18 C17 123.66(14) . . ?
N3 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
