# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_56-aldehyde
_database_code_depnum_ccdc_archive 'CCDC 1532176'
_audit_update_record             
;
2017-12-14 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(5R,7R)-6,6-dimethyl-5,6,7,8-tetrahydro-5,7-methanoquinoline-2-carbaldehyde
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H15 N O'
_chemical_formula_sum            'C13 H15 N O'
_exptl_crystal_recrystallization_method ethylacetate
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         201.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   6.5369(4)
_cell_length_b                   7.0071(3)
_cell_length_c                   12.2187(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.720(5)
_cell_angle_gamma                90
_cell_volume                     549.91(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7550
_cell_measurement_theta_min      1.69
_cell_measurement_theta_max      25.60
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.7733
_exptl_absorpt_correction_T_max  0.9392
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube, 12x0.4 mm long-fine focus'
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7168
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.696
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1944
_reflns_number_gt                1834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.971

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0568P)²+0.0285P] 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_abs_structure_details 
;
 Flack x determined using 789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
The Flack parameter was meaningless, -0.7(10), and has been erased.
;

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1944
_refine_ls_number_parameters     138
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4271(4) 0.5009(4) 0.38332(17) 0.0654(6) Uani 1 1 d . . . . .
H1 H 0.5721 0.4755 0.3933 0.078 Uiso 1 1 calc R U . . .
C2 C 0.3386(3) 0.5320(3) 0.48429(16) 0.0518(4) Uani 1 1 d . . . . .
C3 C 0.1326(3) 0.5794(3) 0.47776(18) 0.0609(5) Uani 1 1 d . . . . .
H3 H 0.0423 0.5913 0.4076 0.073 Uiso 1 1 calc R U . . .
C4 C 0.0601(3) 0.6093(3) 0.57552(19) 0.0603(6) Uani 1 1 d . . . . .
H4 H -0.0815 0.6425 0.5735 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1946(3) 0.5908(3) 0.67601(16) 0.0466(4) Uani 1 1 d . . . . .
C6 C 0.4010(2) 0.5355(3) 0.67449(15) 0.0461(4) Uani 1 1 d . . . . .
C7 C 0.1414(3) 0.6258(3) 0.78834(18) 0.0513(5) Uani 1 1 d . . . . .
H7 H -0.0024 0.6738 0.7890 0.062 Uiso 1 1 calc R U . . .
C8 C 0.2168(3) 0.4548(3) 0.86737(14) 0.0466(4) Uani 1 1 d . . . . .
C9 C 0.4352(3) 0.5509(3) 0.88114(17) 0.0572(5) Uani 1 1 d . . . . .
H9 H 0.5238 0.5395 0.9569 0.069 Uiso 1 1 calc R U . . .
C10 C 0.5445(3) 0.5044(4) 0.78437(16) 0.0601(6) Uani 1 1 d . . . . .
H10A H 0.6690 0.5866 0.7887 0.072 Uiso 1 1 calc R U . . .
H10B H 0.5914 0.3698 0.7900 0.072 Uiso 1 1 calc R U . . .
C11 C 0.3216(4) 0.7421(3) 0.8566(2) 0.0669(6) Uani 1 1 d . . . . .
H11A H 0.3894 0.8315 0.8117 0.080 Uiso 1 1 calc R U . . .
H11B H 0.2865 0.8058 0.9230 0.080 Uiso 1 1 calc R U . . .
C12 C 0.1893(4) 0.2546(3) 0.82072(17) 0.0601(5) Uani 1 1 d . . . . .
H12A H 0.2603 0.1639 0.8761 0.090 Uiso 1 1 calc R U . . .
H12B H 0.2491 0.2465 0.7530 0.090 Uiso 1 1 calc R U . . .
H12C H 0.0406 0.2236 0.8028 0.090 Uiso 1 1 calc R U . . .
C13 C 0.1307(3) 0.4629(4) 0.97508(16) 0.0610(5) Uani 1 1 d . . . . .
H13A H -0.0190 0.4360 0.9589 0.092 Uiso 1 1 calc R U . . .
H13B H 0.1543 0.5903 1.0081 0.092 Uiso 1 1 calc R U . . .
H13C H 0.2015 0.3675 1.0275 0.092 Uiso 1 1 calc R U . . .
N1 N 0.4727(2) 0.5084(2) 0.58104(13) 0.0521(4) Uani 1 1 d . . . . .
O1 O 0.3309(3) 0.5050(3) 0.28930(12) 0.0838(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.203(3) . ?
C1 C2 1.473(3) . ?
C1 H1 0.9500 . ?
C2 N1 1.344(3) . ?
C2 C3 1.375(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(2) . ?
C5 C7 1.498(3) . ?
C6 N1 1.326(2) . ?
C6 C10 1.504(2) . ?
C7 C11 1.543(3) . ?
C7 C8 1.560(3) . ?
C7 H7 1.0000 . ?
C8 C12 1.513(3) . ?
C8 C13 1.526(2) . ?
C8 C9 1.559(3) . ?
C9 C10 1.526(3) . ?
C9 C11 1.534(4) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 125.4(2) . . ?
O1 C1 H1 117.3 . . ?
C2 C1 H1 117.3 . . ?
N1 C2 C3 123.51(18) . . ?
N1 C2 C1 115.15(17) . . ?
C3 C2 C1 121.33(18) . . ?
C2 C3 C4 118.48(19) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 119.47(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 117.98(17) . . ?
C4 C5 C7 125.65(16) . . ?
C6 C5 C7 116.37(17) . . ?
N1 C6 C5 122.96(16) . . ?
N1 C6 C10 119.10(14) . . ?
C5 C6 C10 117.94(16) . . ?
C5 C7 C11 107.30(15) . . ?
C5 C7 C8 109.93(14) . . ?
C11 C7 C8 87.11(16) . . ?
C5 C7 H7 116.2 . . ?
C11 C7 H7 116.2 . . ?
C8 C7 H7 116.2 . . ?
C12 C8 C13 108.80(17) . . ?
C12 C8 C9 118.90(17) . . ?
C13 C8 C9 111.62(15) . . ?
C12 C8 C7 118.51(16) . . ?
C13 C8 C7 112.38(15) . . ?
C9 C8 C7 85.01(15) . . ?
C10 C9 C11 108.30(19) . . ?
C10 C9 C8 112.07(16) . . ?
C11 C9 C8 87.45(15) . . ?
C10 C9 H9 115.3 . . ?
C11 C9 H9 115.3 . . ?
C8 C9 H9 115.3 . . ?
C6 C10 C9 110.89(15) . . ?
C6 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
C9 C11 C7 86.42(16) . . ?
C9 C11 H11A 114.2 . . ?
C7 C11 H11A 114.2 . . ?
C9 C11 H11B 114.2 . . ?
C7 C11 H11B 114.3 . . ?
H11A C11 H11B 111.4 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 N1 C2 117.55(15) . . ?

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
O1 C1 C2 N1 175.8(2) . . . . ?
O1 C1 C2 C3 -3.4(4) . . . . ?
N1 C2 C3 C4 1.7(3) . . . . ?
C1 C2 C3 C4 -179.1(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -2.0(3) . . . . ?
C3 C4 C5 C7 177.53(19) . . . . ?
C4 C5 C6 N1 2.8(3) . . . . ?
C7 C5 C6 N1 -176.75(17) . . . . ?
C4 C5 C6 C10 -176.6(2) . . . . ?
C7 C5 C6 C10 3.8(2) . . . . ?
C4 C5 C7 C11 -135.7(2) . . . . ?
C6 C5 C7 C11 43.8(2) . . . . ?
C4 C5 C7 C8 131.1(2) . . . . ?
C6 C5 C7 C8 -49.4(2) . . . . ?
C5 C7 C8 C12 -40.5(2) . . . . ?
C11 C7 C8 C12 -147.82(19) . . . . ?
C5 C7 C8 C13 -168.80(15) . . . . ?
C11 C7 C8 C13 83.83(17) . . . . ?
C5 C7 C8 C9 79.85(17) . . . . ?
C11 C7 C8 C9 -27.51(14) . . . . ?
C12 C8 C9 C10 38.9(3) . . . . ?
C13 C8 C9 C10 166.82(18) . . . . ?
C7 C8 C9 C10 -81.06(19) . . . . ?
C12 C8 C9 C11 147.62(18) . . . . ?
C13 C8 C9 C11 -84.44(18) . . . . ?
C7 C8 C9 C11 27.68(14) . . . . ?
N1 C6 C10 C9 177.63(18) . . . . ?
C5 C6 C10 C9 -2.9(3) . . . . ?
C11 C9 C10 C6 -46.4(2) . . . . ?
C8 C9 C10 C6 48.4(3) . . . . ?
C10 C9 C11 C7 84.48(17) . . . . ?
C8 C9 C11 C7 -27.94(13) . . . . ?
C5 C7 C11 C9 -82.05(17) . . . . ?
C8 C7 C11 C9 27.94(14) . . . . ?
C5 C6 N1 C2 -1.3(3) . . . . ?
C10 C6 N1 C2 178.10(18) . . . . ?
C3 C2 N1 C6 -1.0(3) . . . . ?
C1 C2 N1 C6 179.74(17) . . . . ?

_refine_diff_density_max         0.112
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_ATE69
_database_code_depnum_ccdc_archive 'CCDC 1532178'
_audit_update_record             
;
2017-12-14 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
6-(7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinolin-3-yl)-2,4-diisopropyl-1,2,4,5-tetrazinan-3-one
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H31 N5 O'
_chemical_formula_sum            'C20 H31 N5 O'
_exptl_crystal_recrystallization_method diethylether
_chemical_melting_point          ?

_exptl_crystal_description       rectangle
_exptl_crystal_colour            Yellow
_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         357.50
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.2955(5)
_cell_length_b                   12.3540(10)
_cell_length_c                   16.2973(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2072.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5813
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      24.49
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.7757
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube, 12x0.4 mm long-fine focus'
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19064
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_av_R_equivalents  0.1324
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.069
_diffrn_reflns_theta_max         25.216
_diffrn_reflns_theta_full        25.216
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3694
_reflns_number_gt                1860
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.979

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0792P)²+0.6082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 570 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(10)
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3694
_refine_ls_number_parameters     236
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1939
_refine_ls_wR_factor_gt          0.1530
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8495(5) 0.7358(6) 0.3580(4) 0.0615(17) Uani 1 1 d . . . . .
H1 H 0.8170 0.7378 0.4144 0.074 Uiso 1 1 calc R U . . .
C2 C 0.7350(5) 0.7432(5) 0.3005(3) 0.0571(17) Uani 1 1 d . . . . .
C3 C 0.6119(5) 0.7627(7) 0.3281(3) 0.076(2) Uani 1 1 d . . . . .
H3 H 0.5955 0.7684 0.3841 0.092 Uiso 1 1 calc R U . . .
C4 C 0.5118(5) 0.7740(7) 0.2722(3) 0.073(2) Uani 1 1 d . . . . .
C5 C 0.5398(5) 0.7627(6) 0.1891(3) 0.0587(17) Uani 1 1 d . U . . .
C6 C 0.6657(5) 0.7401(6) 0.1679(3) 0.0671(19) Uani 1 1 d . U . . .
H6 H 0.6840 0.7308 0.1124 0.081 Uiso 1 1 calc R U . . .
C7 C 0.4300(6) 0.7790(7) 0.1307(3) 0.0712(19) Uani 1 1 d . . . . .
H7 H 0.4516 0.7748 0.0722 0.085 Uiso 1 1 calc R U . . .
C8 C 0.3083(6) 0.7127(8) 0.1591(4) 0.081(2) Uani 1 1 d . U . . .
C9 C 0.2873(7) 0.8081(7) 0.2196(4) 0.0921(16) Uani 1 1 d . U . . .
H9 H 0.1963 0.8268 0.2302 0.111 Uiso 1 1 calc R U . . .
C10 C 0.3715(6) 0.7950(8) 0.2963(4) 0.0921(16) Uani 1 1 d . U . . .
H10A H 0.3665 0.8601 0.3293 0.111 Uiso 1 1 calc R U . . .
H10B H 0.3394 0.7350 0.3289 0.111 Uiso 1 1 calc R U . . .
C11 C 0.3566(7) 0.8813(8) 0.1587(5) 0.0921(16) Uani 1 1 d . U . . .
H11A H 0.4114 0.9360 0.1838 0.111 Uiso 1 1 calc R U . . .
H11B H 0.3004 0.9124 0.1172 0.111 Uiso 1 1 calc R U . . .
C12 C 0.3284(8) 0.6000(8) 0.1923(6) 0.115(3) Uani 1 1 d . . . . .
H12A H 0.2478 0.5729 0.2137 0.173 Uiso 1 1 calc R U . . .
H12B H 0.3920 0.6018 0.2353 0.173 Uiso 1 1 calc R U . . .
H12C H 0.3580 0.5534 0.1490 0.173 Uiso 1 1 calc R U . . .
C13 C 0.2034(7) 0.7121(8) 0.0914(5) 0.105(3) Uani 1 1 d . . . . .
H13A H 0.2289 0.6635 0.0484 0.157 Uiso 1 1 calc R U . . .
H13B H 0.1939 0.7838 0.0695 0.157 Uiso 1 1 calc R U . . .
H13C H 0.1222 0.6887 0.1143 0.157 Uiso 1 1 calc R U . . .
C14 C 1.0887(5) 0.7261(7) 0.4219(4) 0.0621(16) Uani 1 1 d . . . . .
C15 C 1.0716(7) 0.9226(6) 0.4401(4) 0.073(2) Uani 1 1 d . . . . .
H15 H 1.1504 0.9102 0.4725 0.087 Uiso 1 1 calc R U . . .
C15A C 1.0597(7) 0.5307(6) 0.4321(4) 0.071(2) Uani 1 1 d . . . . .
H15A H 1.1447 0.5349 0.4591 0.085 Uiso 1 1 calc R U . . .
C16 C 1.0988(8) 1.0146(6) 0.3827(5) 0.095(3) Uani 1 1 d . . . . .
H16A H 1.1796 1.0019 0.3548 0.143 Uiso 1 1 calc R U . . .
H16B H 1.1044 1.0808 0.4132 0.143 Uiso 1 1 calc R U . . .
H16C H 1.0300 1.0199 0.3432 0.143 Uiso 1 1 calc R U . . .
C16A C 1.0640(9) 0.4388(7) 0.3714(5) 0.101(3) Uani 1 1 d . . . . .
H16D H 0.9832 0.4354 0.3422 0.152 Uiso 1 1 calc R U . . .
H16E H 1.0780 0.3719 0.4001 0.152 Uiso 1 1 calc R U . . .
H16F H 1.1337 0.4505 0.3333 0.152 Uiso 1 1 calc R U . . .
C17 C 0.9610(8) 0.9451(7) 0.5001(4) 0.099(3) Uani 1 1 d . . . . .
H17A H 0.8803 0.9481 0.4708 0.149 Uiso 1 1 calc R U . . .
H17B H 0.9759 1.0131 0.5271 0.149 Uiso 1 1 calc R U . . .
H17C H 0.9573 0.8883 0.5403 0.149 Uiso 1 1 calc R U . . .
C17A C 0.9580(8) 0.5088(7) 0.4978(4) 0.097(3) Uani 1 1 d . . . . .
H17D H 0.9602 0.5657 0.5379 0.145 Uiso 1 1 calc R U . . .
H17E H 0.9762 0.4408 0.5240 0.145 Uiso 1 1 calc R U . . .
H17F H 0.8735 0.5061 0.4730 0.145 Uiso 1 1 calc R U . . .
N1 N 0.7644(4) 0.7304(5) 0.2210(3) 0.0646(14) Uani 1 1 d . . . . .
N2 N 0.9157(5) 0.6345(5) 0.3456(4) 0.0698(16) Uani 1 1 d D . . . .
N3 N 1.0367(5) 0.6339(5) 0.3900(3) 0.0658(15) Uani 1 1 d . . . . .
N4 N 1.0467(5) 0.8242(5) 0.3924(3) 0.0672(16) Uani 1 1 d . . . . .
N5 N 0.9301(6) 0.8298(5) 0.3450(4) 0.0721(17) Uani 1 1 d D . . . .
O1 O 1.1769(4) 0.7209(4) 0.4733(2) 0.0690(12) Uani 1 1 d . . . . .
H2N H 0.938(7) 0.630(6) 0.292(2) 0.083 Uiso 1 1 d D U . . .
H5N H 0.945(6) 0.828(5) 0.2905(18) 0.083 Uiso 1 1 d D 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
C1 N2 1.440(9) . ?
C1 N5 1.442(8) . ?
C1 C2 1.509(7) . ?
C1 H1 0.9800 . ?
C2 N1 1.340(7) . ?
C2 C3 1.366(7) . ?
C3 C4 1.383(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(7) . ?
C4 C10 1.519(8) . ?
C5 C6 1.371(7) . ?
C5 C7 1.491(7) . ?
C6 N1 1.341(7) . ?
C6 H6 0.9300 . ?
C7 C11 1.542(11) . ?
C7 C8 1.566(9) . ?
C7 H7 0.9800 . ?
C8 C12 1.509(12) . ?
C8 C13 1.543(9) . ?
C8 C9 1.552(11) . ?
C9 C11 1.521(11) . ?
C9 C10 1.529(9) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O1 1.238(6) . ?
C14 N3 1.362(9) . ?
C14 N4 1.373(8) . ?
C15 N4 1.466(8) . ?
C15 C16 1.498(10) . ?
C15 C17 1.526(10) . ?
C15 H15 0.9800 . ?
C15A N3 1.467(9) . ?
C15A C16A 1.506(10) . ?
C15A C17A 1.521(10) . ?
C15A H15A 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
N2 N3 1.440(7) . ?
N2 H2N 0.91(3) . ?
N4 N5 1.430(7) . ?
N5 H5N 0.90(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N5 114.0(5) . . ?
N2 C1 C2 109.6(5) . . ?
N5 C1 C2 108.0(5) . . ?
N2 C1 H1 108.3 . . ?
N5 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
N1 C2 C3 123.3(5) . . ?
N1 C2 C1 114.6(5) . . ?
C3 C2 C1 122.1(5) . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.5(5) . . ?
C3 C4 C10 123.7(5) . . ?
C5 C4 C10 117.7(5) . . ?
C6 C5 C4 117.5(5) . . ?
C6 C5 C7 125.7(5) . . ?
C4 C5 C7 116.8(5) . . ?
N1 C6 C5 124.9(5) . . ?
N1 C6 H6 117.5 . . ?
C5 C6 H6 117.5 . . ?
C5 C7 C11 107.0(6) . . ?
C5 C7 C8 110.3(5) . . ?
C11 C7 C8 87.1(6) . . ?
C5 C7 H7 116.2 . . ?
C11 C7 H7 116.2 . . ?
C8 C7 H7 116.2 . . ?
C12 C8 C13 110.4(8) . . ?
C12 C8 C9 119.4(7) . . ?
C13 C8 C9 111.1(7) . . ?
C12 C8 C7 118.6(6) . . ?
C13 C8 C7 110.6(6) . . ?
C9 C8 C7 84.4(6) . . ?
C11 C9 C10 109.3(6) . . ?
C11 C9 C8 88.3(6) . . ?
C10 C9 C8 111.1(6) . . ?
C11 C9 H9 115.1 . . ?
C10 C9 H9 115.1 . . ?
C8 C9 H9 115.1 . . ?
C4 C10 C9 110.3(5) . . ?
C4 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C4 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C9 C11 C7 86.3(7) . . ?
C9 C11 H11A 114.3 . . ?
C7 C11 H11A 114.3 . . ?
C9 C11 H11B 114.3 . . ?
C7 C11 H11B 114.3 . . ?
H11A C11 H11B 111.4 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 N3 120.2(7) . . ?
O1 C14 N4 120.9(7) . . ?
N3 C14 N4 118.8(5) . . ?
N4 C15 C16 109.3(6) . . ?
N4 C15 C17 111.1(6) . . ?
C16 C15 C17 113.7(7) . . ?
N4 C15 H15 107.5 . . ?
C16 C15 H15 107.5 . . ?
C17 C15 H15 107.5 . . ?
N3 C15A C16A 110.6(6) . . ?
N3 C15A C17A 111.9(6) . . ?
C16A C15A C17A 110.4(7) . . ?
N3 C15A H15A 107.9 . . ?
C16A C15A H15A 107.9 . . ?
C17A C15A H15A 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15A C17A H17D 109.5 . . ?
C15A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C15A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C2 N1 C6 116.2(4) . . ?
C1 N2 N3 110.1(5) . . ?
C1 N2 H2N 108(5) . . ?
N3 N2 H2N 105(5) . . ?
C14 N3 N2 121.8(5) . . ?
C14 N3 C15A 119.0(6) . . ?
N2 N3 C15A 112.3(6) . . ?
C14 N4 N5 119.7(5) . . ?
C14 N4 C15 119.4(5) . . ?
N5 N4 C15 113.2(6) . . ?
N4 N5 C1 111.4(5) . . ?
N4 N5 H5N 113(4) . . ?
C1 N5 H5N 103(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 N1 -55.5(8) . . . . ?
N5 C1 C2 N1 69.3(8) . . . . ?
N2 C1 C2 C3 125.2(7) . . . . ?
N5 C1 C2 C3 -110.0(8) . . . . ?
N1 C2 C3 C4 -2.4(13) . . . . ?
C1 C2 C3 C4 176.8(7) . . . . ?
C2 C3 C4 C5 1.3(12) . . . . ?
C2 C3 C4 C10 179.5(8) . . . . ?
C3 C4 C5 C6 0.5(11) . . . . ?
C10 C4 C5 C6 -177.8(8) . . . . ?
C3 C4 C5 C7 -178.1(8) . . . . ?
C10 C4 C5 C7 3.6(11) . . . . ?
C4 C5 C6 N1 -1.6(12) . . . . ?
C7 C5 C6 N1 177.0(7) . . . . ?
C6 C5 C7 C11 -133.5(8) . . . . ?
C4 C5 C7 C11 45.0(9) . . . . ?
C6 C5 C7 C8 133.2(7) . . . . ?
C4 C5 C7 C8 -48.2(10) . . . . ?
C5 C7 C8 C12 -40.8(9) . . . . ?
C11 C7 C8 C12 -147.8(7) . . . . ?
C5 C7 C8 C13 -169.7(7) . . . . ?
C11 C7 C8 C13 83.3(7) . . . . ?
C5 C7 C8 C9 79.8(7) . . . . ?
C11 C7 C8 C9 -27.2(5) . . . . ?
C12 C8 C9 C11 147.4(6) . . . . ?
C13 C8 C9 C11 -82.3(7) . . . . ?
C7 C8 C9 C11 27.6(5) . . . . ?
C12 C8 C9 C10 37.4(9) . . . . ?
C13 C8 C9 C10 167.6(6) . . . . ?
C7 C8 C9 C10 -82.5(7) . . . . ?
C3 C4 C10 C9 177.5(8) . . . . ?
C5 C4 C10 C9 -4.3(12) . . . . ?
C11 C9 C10 C4 -44.8(10) . . . . ?
C8 C9 C10 C4 51.0(10) . . . . ?
C10 C9 C11 C7 83.8(7) . . . . ?
C8 C9 C11 C7 -28.0(5) . . . . ?
C5 C7 C11 C9 -82.6(6) . . . . ?
C8 C7 C11 C9 27.8(5) . . . . ?
C3 C2 N1 C6 1.4(11) . . . . ?
C1 C2 N1 C6 -177.8(6) . . . . ?
C5 C6 N1 C2 0.6(11) . . . . ?
N5 C1 N2 N3 49.3(6) . . . . ?
C2 C1 N2 N3 170.5(5) . . . . ?
O1 C14 N3 N2 165.1(5) . . . . ?
N4 C14 N3 N2 -18.7(8) . . . . ?
O1 C14 N3 C15A 16.5(8) . . . . ?
N4 C14 N3 C15A -167.3(6) . . . . ?
C1 N2 N3 C14 -13.4(8) . . . . ?
C1 N2 N3 C15A 137.1(6) . . . . ?
C16A C15A N3 C14 -148.6(6) . . . . ?
C17A C15A N3 C14 87.9(7) . . . . ?
C16A C15A N3 N2 60.0(8) . . . . ?
C17A C15A N3 N2 -63.6(7) . . . . ?
O1 C14 N4 N5 -168.6(5) . . . . ?
N3 C14 N4 N5 15.2(8) . . . . ?
O1 C14 N4 C15 -21.2(9) . . . . ?
N3 C14 N4 C15 162.6(6) . . . . ?
C16 C15 N4 C14 144.2(6) . . . . ?
C17 C15 N4 C14 -89.6(8) . . . . ?
C16 C15 N4 N5 -66.4(8) . . . . ?
C17 C15 N4 N5 59.9(8) . . . . ?
C14 N4 N5 C1 19.6(8) . . . . ?
C15 N4 N5 C1 -129.7(6) . . . . ?
N2 C1 N5 N4 -52.9(7) . . . . ?
C2 C1 N5 N4 -175.1(5) . . . . ?

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_ATE80
_database_code_depnum_ccdc_archive 'CCDC 1811236'
_audit_update_record             
;
2017-12-14 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '2(C20 H28 Cl2 Cu N5 O)'
_chemical_formula_sum            'C20 H28 Cl2 Cu N5 O'
_exptl_crystal_recrystallization_method Ethanol
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         488.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_chemical_absolute_configuration syn

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

_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.
;

_cell_length_a                   13.0978(9)
_cell_length_b                   11.0063(7)
_cell_length_c                   16.8554(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.955(6)
_cell_angle_gamma                90
_cell_volume                     2336.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4951
_cell_measurement_theta_min      1.26
_cell_measurement_theta_max      23.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.184
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.7442
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube, 12x0.4 mm long-fine focus'
_diffrn_source_type              'Stoe IPDS2'
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30974
_diffrn_reflns_av_unetI/netI     0.2514
_diffrn_reflns_av_R_equivalents  0.3274
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.256
_diffrn_reflns_theta_max         25.196
_diffrn_reflns_theta_full        25.196
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             8335
_reflns_number_gt                2991
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.988

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0716P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_number_reflns         8335
_refine_ls_number_parameters     481
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.2226
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.2174
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5128(19) 0.595(3) 0.2647(16) 0.046(6) Uani 1 1 d . U . . .
C2 C 0.543(2) 0.591(3) 0.3559(19) 0.053(8) Uani 1 1 d . . . . .
C3 C 0.497(2) 0.668(3) 0.406(2) 0.058(8) Uani 1 1 d . . . . .
H3 H 0.4446 0.7246 0.3829 0.070 Uiso 1 1 calc R U . . .
C4 C 0.5365(19) 0.653(3) 0.4903(19) 0.056(8) Uani 1 1 d . . . . .
C5 C 0.6103(17) 0.562(2) 0.5211(15) 0.048(7) Uani 1 1 d . . . . .
C6 C 0.6494(19) 0.490(2) 0.4694(18) 0.044(6) Uani 1 1 d . . . . .
H6 H 0.6973 0.4276 0.4909 0.052 Uiso 1 1 calc R U . . .
C7 C 0.6398(16) 0.5438(19) 0.6132(12) 0.059(5) Uani 1 1 d . . . . .
H7 H 0.6904 0.4787 0.6357 0.071 Uiso 1 1 calc R U . . .
C8 C 0.6599(17) 0.668(2) 0.6577(14) 0.062(4) Uani 1 1 d . . . . .
C9 C 0.5351(15) 0.681(2) 0.6350(12) 0.059(6) Uani 1 1 d . . . . .
H9 H 0.5089 0.7237 0.6767 0.070 Uiso 1 1 calc R U . . .
C11 C 0.532(2) 0.544(3) 0.640(2) 0.077(7) Uani 1 1 d . . . . .
H11A H 0.4720 0.5074 0.5994 0.092 Uiso 1 1 calc R U . . .
H11B H 0.5384 0.5126 0.6946 0.092 Uiso 1 1 calc R U . . .
C10 C 0.492(2) 0.730(3) 0.5481(17) 0.084(10) Uani 1 1 d . . . . .
H10A H 0.5120 0.8139 0.5456 0.101 Uiso 1 1 calc R U . . .
H10B H 0.4147 0.7248 0.5317 0.101 Uiso 1 1 calc R U . . .
C12 C 0.722(2) 0.763(3) 0.6253(18) 0.079(4) Uani 1 1 d . . . . .
H12A H 0.6918 0.7722 0.5669 0.119 Uiso 1 1 calc R U . . .
H12B H 0.7186 0.8389 0.6523 0.119 Uiso 1 1 calc R U . . .
H12C H 0.7946 0.7376 0.6361 0.119 Uiso 1 1 calc R U . . .
C13 C 0.7138(18) 0.659(2) 0.7510(13) 0.079(4) Uani 1 1 d . . . . .
H13A H 0.6778 0.6000 0.7752 0.119 Uiso 1 1 calc R U . . .
H13B H 0.7867 0.6358 0.7599 0.119 Uiso 1 1 calc R U . . .
H13C H 0.7107 0.7371 0.7760 0.119 Uiso 1 1 calc R U . . .
C14 C 0.479(2) 0.597(3) 0.1015(19) 0.056(6) Uani 1 1 d . U . . .
C15 C 0.421(2) 0.819(2) 0.1053(16) 0.060(3) Uani 1 1 d . . . . .
H15 H 0.4096 0.8100 0.0456 0.072 Uiso 1 1 calc R U . . .
C15A C 0.491(2) 0.378(3) 0.0988(18) 0.060(3) Uani 1 1 d . . . . .
H15A H 0.5302 0.3888 0.0572 0.072 Uiso 1 1 calc R U . . .
C16 C 0.316(2) 0.846(3) 0.122(2) 0.090(11) Uani 1 1 d . . . . .
H16A H 0.2888 0.9216 0.0963 0.134 Uiso 1 1 calc R U . . .
H16B H 0.2663 0.7820 0.0989 0.134 Uiso 1 1 calc R U . . .
H16C H 0.3250 0.8508 0.1800 0.134 Uiso 1 1 calc R U . . .
C16A C 0.370(2) 0.357(3) 0.053(2) 0.078(10) Uani 1 1 d . . . . .
H16D H 0.3424 0.4273 0.0200 0.117 Uiso 1 1 calc R U . . .
H16E H 0.3631 0.2872 0.0177 0.117 Uiso 1 1 calc R U . . .
H16F H 0.3311 0.3442 0.0927 0.117 Uiso 1 1 calc R U . . .
C17 C 0.505(3) 0.918(3) 0.137(2) 0.090(11) Uani 1 1 d . . . . .
H17A H 0.4793 0.9939 0.1108 0.136 Uiso 1 1 calc R U . . .
H17B H 0.5187 0.9260 0.1955 0.136 Uiso 1 1 calc R U . . .
H17C H 0.5695 0.8962 0.1237 0.136 Uiso 1 1 calc R U . . .
C17A C 0.534(3) 0.270(3) 0.149(2) 0.088(12) Uani 1 1 d . . . . .
H17D H 0.5266 0.2006 0.1140 0.132 Uiso 1 1 calc R U . . .
H17E H 0.6071 0.2832 0.1772 0.132 Uiso 1 1 calc R U . . .
H17F H 0.4945 0.2575 0.1889 0.132 Uiso 1 1 calc R U . . .
C21 C 0.0054(19) 0.422(3) 0.2583(17) 0.045(5) Uani 1 1 d . U . . .
C22 C 0.042(2) 0.425(3) 0.3520(16) 0.043(7) Uani 1 1 d . . . . .
C23 C 0.013(2) 0.345(3) 0.3995(17) 0.045(7) Uani 1 1 d . . . . .
H23 H -0.0411 0.2902 0.3758 0.054 Uiso 1 1 calc R U . . .
C24 C 0.059(2) 0.341(3) 0.482(2) 0.061(8) Uani 1 1 d . . . . .
C25 C 0.1394(18) 0.429(2) 0.5151(18) 0.056(7) Uani 1 1 d . . . . .
C26 C 0.1666(19) 0.507(2) 0.4616(19) 0.049(7) Uani 1 1 d . . . . .
H26 H 0.2226 0.5606 0.4826 0.058 Uiso 1 1 calc R U . . .
C27 C 0.1991(15) 0.4143(19) 0.6048(11) 0.051(5) Uani 1 1 d . . . . .
H27 H 0.2584 0.4703 0.6263 0.062 Uiso 1 1 calc R U . . .
C28 C 0.1185(17) 0.398(2) 0.6591(13) 0.062(4) Uani 1 1 d . . . . .
C29 C 0.1096(18) 0.2679(19) 0.6299(13) 0.062(6) Uani 1 1 d . . . . .
H29 H 0.1008 0.2080 0.6706 0.074 Uiso 1 1 calc R U . . .
C30 C 0.030(2) 0.254(3) 0.5422(16) 0.065(7) Uani 1 1 d . . . . .
H30A H 0.0322 0.1716 0.5230 0.078 Uiso 1 1 calc R U . . .
H30B H -0.0412 0.2713 0.5451 0.078 Uiso 1 1 calc R U . . .
C31 C 0.225(2) 0.276(3) 0.618(2) 0.090(10) Uani 1 1 d . . . . .
H31A H 0.2812 0.2569 0.6676 0.108 Uiso 1 1 calc R U . . .
H31B H 0.2336 0.2334 0.5704 0.108 Uiso 1 1 calc R U . . .
C32 C 0.022(2) 0.483(3) 0.6367(19) 0.079(4) Uani 1 1 d . . . . .
H32A H 0.0420 0.5614 0.6603 0.119 Uiso 1 1 calc R U . . .
H32B H -0.0037 0.4897 0.5778 0.119 Uiso 1 1 calc R U . . .
H32C H -0.0332 0.4498 0.6580 0.119 Uiso 1 1 calc R U . . .
C33 C 0.1778(18) 0.413(2) 0.7510(13) 0.079(4) Uani 1 1 d . . . . .
H33A H 0.1805 0.4980 0.7653 0.119 Uiso 1 1 calc R U . . .
H33B H 0.1412 0.3694 0.7841 0.119 Uiso 1 1 calc R U . . .
H33C H 0.2487 0.3823 0.7610 0.119 Uiso 1 1 calc R U . . .
C34 C -0.038(2) 0.424(3) 0.0946(19) 0.058(6) Uani 1 1 d . U . . .
C35 C -0.0992(19) 0.219(2) 0.0928(16) 0.060(3) Uani 1 1 d . . . . .
H35 H -0.1068 0.2317 0.0339 0.072 Uiso 1 1 calc R U . . .
C35A C -0.022(2) 0.650(3) 0.0968(18) 0.060(3) Uani 1 1 d . . . . .
H35A H 0.0085 0.6408 0.0503 0.072 Uiso 1 1 calc R U . . .
C36 C -0.020(2) 0.115(3) 0.1250(17) 0.072(10) Uani 1 1 d . . . . .
H36A H -0.0472 0.0410 0.0968 0.108 Uiso 1 1 calc R U . . .
H36B H 0.0469 0.1342 0.1150 0.108 Uiso 1 1 calc R U . . .
H36C H -0.0103 0.1048 0.1831 0.108 Uiso 1 1 calc R U . . .
C36A C 0.037(2) 0.750(3) 0.1524(19) 0.065(9) Uani 1 1 d . . . . .
H36D H 0.0285 0.8253 0.1223 0.097 Uiso 1 1 calc R U . . .
H36E H 0.0100 0.7585 0.1994 0.097 Uiso 1 1 calc R U . . .
H36F H 0.1115 0.7300 0.1706 0.097 Uiso 1 1 calc R U . . .
C37 C -0.207(2) 0.195(3) 0.1058(19) 0.080(10) Uani 1 1 d . . . . .
H37A H -0.2374 0.1242 0.0751 0.120 Uiso 1 1 calc R U . . .
H37B H -0.1991 0.1815 0.1634 0.120 Uiso 1 1 calc R U . . .
H37C H -0.2521 0.2637 0.0873 0.120 Uiso 1 1 calc R U . . .
C37A C -0.138(2) 0.682(3) 0.063(2) 0.100(13) Uani 1 1 d . . . . .
H37D H -0.1446 0.7579 0.0334 0.150 Uiso 1 1 calc R U . . .
H37E H -0.1738 0.6195 0.0258 0.150 Uiso 1 1 calc R U . . .
H37F H -0.1704 0.6899 0.1073 0.150 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7531(6) 0.4969(7) 0.2118(6) 0.068(2) Uani 1 1 d . . . . .
Cl2 Cl 0.7446(6) 0.2619(7) 0.3610(6) 0.068(2) Uani 1 1 d . . . . .
Cl3 Cl 0.2494(6) 0.5354(7) 0.2040(6) 0.068(2) Uani 1 1 d . . . . .
Cl4 Cl 0.2381(6) 0.7538(8) 0.3628(6) 0.071(2) Uani 1 1 d . . . . .
Cu1 Cu 0.6655(3) 0.4254(2) 0.2962(2) 0.0537(11) Uani 1 1 d . . . . .
Cu2 Cu 0.1615(3) 0.5955(2) 0.2929(2) 0.0543(11) Uani 1 1 d . . . . .
N1 N 0.6165(16) 0.510(2) 0.3840(14) 0.050(7) Uani 1 1 d . . . . .
N2 N 0.5283(16) 0.487(2) 0.2286(13) 0.048(5) Uani 1 1 d . U . . .
N3 N 0.4968(17) 0.493(2) 0.1449(14) 0.047(5) Uani 1 1 d . U . . .
N4 N 0.4607(17) 0.700(2) 0.1456(15) 0.052(5) Uani 1 1 d . U . . .
N5 N 0.4791(18) 0.699(2) 0.2267(15) 0.053(5) Uani 1 1 d . U . . .
N6 N 0.1186(16) 0.512(2) 0.3825(15) 0.048(6) Uani 1 1 d . . . . .
N7 N 0.0240(17) 0.531(2) 0.2264(15) 0.050(5) Uani 1 1 d . U . . .
N8 N -0.0090(18) 0.533(2) 0.1427(16) 0.058(6) Uani 1 1 d . U . . .
N9 N -0.0515(18) 0.325(2) 0.1385(14) 0.051(5) Uani 1 1 d . U . . .
N10 N -0.0316(17) 0.321(2) 0.2232(14) 0.052(6) Uani 1 1 d . U . . .
O1 O 0.4620(15) 0.606(2) 0.0261(13) 0.071(6) Uani 1 1 d . . . . .
O2 O -0.0573(17) 0.432(2) 0.0206(13) 0.083(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
C1 N5 1.32(3) . ?
C1 N2 1.38(3) . ?
C1 C2 1.48(4) . ?
C2 N1 1.30(3) . ?
C2 C3 1.44(4) . ?
C3 C4 1.38(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.39(3) . ?
C4 C10 1.52(4) . ?
C5 C6 1.38(3) . ?
C5 C7 1.50(3) . ?
C6 N1 1.40(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.54(3) . ?
C7 C11 1.60(3) . ?
C7 H7 0.9800 . ?
C8 C12 1.52(4) . ?
C8 C13 1.54(3) . ?
C8 C9 1.58(3) . ?
C9 C10 1.51(3) . ?
C9 C11 1.52(4) . ?
C9 H9 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O1 1.23(3) . ?
C14 N3 1.34(4) . ?
C14 N4 1.41(4) . ?
C15 N4 1.50(3) . ?
C15 C16 1.51(4) . ?
C15 C17 1.54(3) . ?
C15 H15 0.9800 . ?
C15A C17A 1.48(4) . ?
C15A N3 1.48(3) . ?
C15A C16A 1.58(4) . ?
C15A H15A 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C21 N10 1.29(3) . ?
C21 N7 1.36(3) . ?
C21 C22 1.52(4) . ?
C22 C23 1.32(4) . ?
C22 N6 1.37(3) . ?
C23 C24 1.36(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.43(4) . ?
C24 C30 1.51(4) . ?
C25 C26 1.37(4) . ?
C25 C27 1.51(3) . ?
C26 N6 1.31(4) . ?
C26 H26 0.9300 . ?
C27 C31 1.56(3) . ?
C27 C28 1.59(3) . ?
C27 H27 0.9800 . ?
C28 C29 1.51(3) . ?
C28 C32 1.53(3) . ?
C28 C33 1.54(3) . ?
C29 C30 1.56(3) . ?
C29 C31 1.57(4) . ?
C29 H29 0.9800 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 O2 1.21(3) . ?
C34 N9 1.35(4) . ?
C34 N8 1.44(4) . ?
C35 N9 1.44(3) . ?
C35 C37 1.51(3) . ?
C35 C36 1.54(3) . ?
C35 H35 0.9800 . ?
C35A N8 1.48(4) . ?
C35A C37A 1.51(4) . ?
C35A C36A 1.52(4) . ?
C35A H35A 0.9800 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C36A H36D 0.9600 . ?
C36A H36E 0.9600 . ?
C36A H36F 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C37A H37D 0.9600 . ?
C37A H37E 0.9600 . ?
C37A H37F 0.9600 . ?
Cl1 Cu1 2.204(9) . ?
Cl2 Cu1 2.210(9) . ?
Cl3 Cu2 2.226(9) . ?
Cl4 Cu2 2.186(9) . ?
Cu1 N2 1.96(2) . ?
Cu1 N1 2.00(2) . ?
Cu2 N7 1.97(2) . ?
Cu2 N6 1.98(2) . ?
N2 N3 1.36(3) . ?
N4 N5 1.32(3) . ?
N7 N8 1.36(3) . ?
N9 N10 1.38(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 C1 N2 127(2) . . ?
N5 C1 C2 119(3) . . ?
N2 C1 C2 114(3) . . ?
N1 C2 C3 125(3) . . ?
N1 C2 C1 111(3) . . ?
C3 C2 C1 124(3) . . ?
C4 C3 C2 116(3) . . ?
C4 C3 H3 122.1 . . ?
C2 C3 H3 122.1 . . ?
C3 C4 C5 120(3) . . ?
C3 C4 C10 119(2) . . ?
C5 C4 C10 121(3) . . ?
C6 C5 C4 121(2) . . ?
C6 C5 C7 123(2) . . ?
C4 C5 C7 116(2) . . ?
C5 C6 N1 120(2) . . ?
C5 C6 H6 120.2 . . ?
N1 C6 H6 120.2 . . ?
C5 C7 C8 110.3(18) . . ?
C5 C7 C11 106.9(18) . . ?
C8 C7 C11 84.7(18) . . ?
C5 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C11 C7 H7 116.8 . . ?
C12 C8 C13 106(2) . . ?
C12 C8 C7 118(2) . . ?
C13 C8 C7 114(2) . . ?
C12 C8 C9 118(2) . . ?
C13 C8 C9 114.0(18) . . ?
C7 C8 C9 86.6(16) . . ?
C10 C9 C11 113(2) . . ?
C10 C9 C8 110.9(18) . . ?
C11 C9 C8 86.3(18) . . ?
C10 C9 H9 114.6 . . ?
C11 C9 H9 114.6 . . ?
C8 C9 H9 114.6 . . ?
C9 C11 C7 86.9(19) . . ?
C9 C11 H11A 114.2 . . ?
C7 C11 H11A 114.2 . . ?
C9 C11 H11B 114.2 . . ?
C7 C11 H11B 114.2 . . ?
H11A C11 H11B 111.3 . . ?
C9 C10 C4 109(2) . . ?
C9 C10 H10A 110.0 . . ?
C4 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
C4 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 N3 126(3) . . ?
O1 C14 N4 118(3) . . ?
N3 C14 N4 115(3) . . ?
N4 C15 C16 108(2) . . ?
N4 C15 C17 110(2) . . ?
C16 C15 C17 114(3) . . ?
N4 C15 H15 108.4 . . ?
C16 C15 H15 108.4 . . ?
C17 C15 H15 108.4 . . ?
C17A C15A N3 115(2) . . ?
C17A C15A C16A 109(3) . . ?
N3 C15A C16A 106(2) . . ?
C17A C15A H15A 108.5 . . ?
N3 C15A H15A 108.5 . . ?
C16A C15A H15A 108.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15A C17A H17D 109.5 . . ?
C15A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C15A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
N10 C21 N7 131(3) . . ?
N10 C21 C22 118(3) . . ?
N7 C21 C22 110(3) . . ?
C23 C22 N6 123(3) . . ?
C23 C22 C21 123(3) . . ?
N6 C22 C21 113(3) . . ?
C22 C23 C24 121(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C25 117(3) . . ?
C23 C24 C30 126(3) . . ?
C25 C24 C30 117(3) . . ?
C26 C25 C24 118(3) . . ?
C26 C25 C27 125(2) . . ?
C24 C25 C27 116(3) . . ?
N6 C26 C25 124(3) . . ?
N6 C26 H26 118.0 . . ?
C25 C26 H26 118.0 . . ?
C25 C27 C31 106(2) . . ?
C25 C27 C28 110.3(17) . . ?
C31 C27 C28 87(2) . . ?
C25 C27 H27 116.4 . . ?
C31 C27 H27 116.4 . . ?
C28 C27 H27 116.4 . . ?
C29 C28 C32 121(2) . . ?
C29 C28 C33 113.9(19) . . ?
C32 C28 C33 110(2) . . ?
C29 C28 C27 85.7(17) . . ?
C32 C28 C27 115(2) . . ?
C33 C28 C27 109.6(18) . . ?
C28 C29 C30 111.8(18) . . ?
C28 C29 C31 90(2) . . ?
C30 C29 C31 107(2) . . ?
C28 C29 H29 115.0 . . ?
C30 C29 H29 115.0 . . ?
C31 C29 H29 115.0 . . ?
C24 C30 C29 111(2) . . ?
C24 C30 H30A 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C24 C30 H30B 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
C27 C31 C29 84.2(18) . . ?
C27 C31 H31A 114.6 . . ?
C29 C31 H31A 114.6 . . ?
C27 C31 H31B 114.6 . . ?
C29 C31 H31B 114.6 . . ?
H31A C31 H31B 111.7 . . ?
C28 C32 H32A 109.5 . . ?
C28 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C28 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 C33 H33A 109.5 . . ?
C28 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C28 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O2 C34 N9 127(3) . . ?
O2 C34 N8 118(3) . . ?
N9 C34 N8 115(3) . . ?
N9 C35 C37 110(2) . . ?
N9 C35 C36 105(2) . . ?
C37 C35 C36 113(3) . . ?
N9 C35 H35 109.5 . . ?
C37 C35 H35 109.5 . . ?
C36 C35 H35 109.5 . . ?
N8 C35A C37A 111(2) . . ?
N8 C35A C36A 110(2) . . ?
C37A C35A C36A 111(2) . . ?
N8 C35A H35A 108.2 . . ?
C37A C35A H35A 108.2 . . ?
C36A C35A H35A 108.2 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35A C36A H36D 109.5 . . ?
C35A C36A H36E 109.5 . . ?
H36D C36A H36E 109.5 . . ?
C35A C36A H36F 109.5 . . ?
H36D C36A H36F 109.5 . . ?
H36E C36A H36F 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35A C37A H37D 109.5 . . ?
C35A C37A H37E 109.5 . . ?
H37D C37A H37E 109.5 . . ?
C35A C37A H37F 109.5 . . ?
H37D C37A H37F 109.5 . . ?
H37E C37A H37F 109.5 . . ?
N2 Cu1 N1 80.8(8) . . ?
N2 Cu1 Cl1 93.3(7) . . ?
N1 Cu1 Cl1 129.9(8) . . ?
N2 Cu1 Cl2 142.8(7) . . ?
N1 Cu1 Cl2 102.5(7) . . ?
Cl1 Cu1 Cl2 110.7(3) . . ?
N7 Cu2 N6 81.9(10) . . ?
N7 Cu2 Cl4 143.6(6) . . ?
N6 Cu2 Cl4 98.2(8) . . ?
N7 Cu2 Cl3 94.1(7) . . ?
N6 Cu2 Cl3 133.2(7) . . ?
Cl4 Cu2 Cl3 110.8(3) . . ?
C2 N1 C6 118(3) . . ?
C2 N1 Cu1 114(2) . . ?
C6 N1 Cu1 127.9(18) . . ?
N3 N2 C1 112(2) . . ?
N3 N2 Cu1 126.1(17) . . ?
C1 N2 Cu1 105.3(17) . . ?
C14 N3 N2 125(2) . . ?
C14 N3 C15A 118(2) . . ?
N2 N3 C15A 117(2) . . ?
N5 N4 C14 122(3) . . ?
N5 N4 C15 115(2) . . ?
C14 N4 C15 123(2) . . ?
N4 N5 C1 117(2) . . ?
C26 N6 C22 117(3) . . ?
C26 N6 Cu2 130(2) . . ?
C22 N6 Cu2 112(2) . . ?
N8 N7 C21 113(2) . . ?
N8 N7 Cu2 124(2) . . ?
C21 N7 Cu2 109.1(18) . . ?
N7 N8 C34 122(3) . . ?
N7 N8 C35A 121(2) . . ?
C34 N8 C35A 117(2) . . ?
C34 N9 N10 125(3) . . ?
C34 N9 C35 117(2) . . ?
N10 N9 C35 117(2) . . ?
C21 N10 N9 113(2) . . ?

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
N5 C1 C2 N1 -150(3) . . . . ?
N2 C1 C2 N1 27(4) . . . . ?
N5 C1 C2 C3 30(4) . . . . ?
N2 C1 C2 C3 -153(3) . . . . ?
N1 C2 C3 C4 1(5) . . . . ?
C1 C2 C3 C4 -179(3) . . . . ?
C2 C3 C4 C5 -4(4) . . . . ?
C2 C3 C4 C10 -179(2) . . . . ?
C3 C4 C5 C6 3(4) . . . . ?
C10 C4 C5 C6 178(2) . . . . ?
C3 C4 C5 C7 -174(2) . . . . ?
C10 C4 C5 C7 1(4) . . . . ?
C4 C5 C6 N1 2(4) . . . . ?
C7 C5 C6 N1 179(2) . . . . ?
C6 C5 C7 C8 138(2) . . . . ?
C4 C5 C7 C8 -45(3) . . . . ?
C6 C5 C7 C11 -131(2) . . . . ?
C4 C5 C7 C11 46(3) . . . . ?
C5 C7 C8 C12 -42(3) . . . . ?
C11 C7 C8 C12 -148(2) . . . . ?
C5 C7 C8 C13 -167.2(18) . . . . ?
C11 C7 C8 C13 87(2) . . . . ?
C5 C7 C8 C9 77.9(18) . . . . ?
C11 C7 C8 C9 -28.2(17) . . . . ?
C12 C8 C9 C10 37(3) . . . . ?
C13 C8 C9 C10 161(2) . . . . ?
C7 C8 C9 C10 -83(2) . . . . ?
C12 C8 C9 C11 150(3) . . . . ?
C13 C8 C9 C11 -85(2) . . . . ?
C7 C8 C9 C11 29.9(19) . . . . ?
C10 C9 C11 C7 82(2) . . . . ?
C8 C9 C11 C7 -28.7(16) . . . . ?
C5 C7 C11 C9 -80(2) . . . . ?
C8 C7 C11 C9 29.6(17) . . . . ?
C11 C9 C10 C4 -45(3) . . . . ?
C8 C9 C10 C4 50(3) . . . . ?
C3 C4 C10 C9 171(3) . . . . ?
C5 C4 C10 C9 -4(4) . . . . ?
N10 C21 C22 C23 -20(4) . . . . ?
N7 C21 C22 C23 164(2) . . . . ?
N10 C21 C22 N6 154(2) . . . . ?
N7 C21 C22 N6 -23(3) . . . . ?
N6 C22 C23 C24 -2(4) . . . . ?
C21 C22 C23 C24 171(3) . . . . ?
C22 C23 C24 C25 1(4) . . . . ?
C22 C23 C24 C30 179(3) . . . . ?
C23 C24 C25 C26 -2(4) . . . . ?
C30 C24 C25 C26 180(2) . . . . ?
C23 C24 C25 C27 -173(2) . . . . ?
C30 C24 C25 C27 9(3) . . . . ?
C24 C25 C26 N6 5(4) . . . . ?
C27 C25 C26 N6 175(2) . . . . ?
C26 C25 C27 C31 -127(3) . . . . ?
C24 C25 C27 C31 44(3) . . . . ?
C26 C25 C27 C28 140(2) . . . . ?
C24 C25 C27 C28 -50(3) . . . . ?
C25 C27 C28 C29 79(2) . . . . ?
C31 C27 C28 C29 -27.1(17) . . . . ?
C25 C27 C28 C32 -43(3) . . . . ?
C31 C27 C28 C32 -149(2) . . . . ?
C25 C27 C28 C33 -167(2) . . . . ?
C31 C27 C28 C33 87(2) . . . . ?
C32 C28 C29 C30 35(3) . . . . ?
C33 C28 C29 C30 168.7(19) . . . . ?
C27 C28 C29 C30 -82(2) . . . . ?
C32 C28 C29 C31 144(3) . . . . ?
C33 C28 C29 C31 -83(2) . . . . ?
C27 C28 C29 C31 26.9(16) . . . . ?
C23 C24 C30 C29 174(3) . . . . ?
C25 C24 C30 C29 -8(3) . . . . ?
C28 C29 C30 C24 53(3) . . . . ?
C31 C29 C30 C24 -44(3) . . . . ?
C25 C27 C31 C29 -84(2) . . . . ?
C28 C27 C31 C29 25.9(16) . . . . ?
C28 C29 C31 C27 -27.3(17) . . . . ?
C30 C29 C31 C27 85(2) . . . . ?
C3 C2 N1 C6 4(4) . . . . ?
C1 C2 N1 C6 -176(2) . . . . ?
C3 C2 N1 Cu1 -178(2) . . . . ?
C1 C2 N1 Cu1 3(3) . . . . ?
C5 C6 N1 C2 -5(4) . . . . ?
C5 C6 N1 Cu1 176.7(17) . . . . ?
N5 C1 N2 N3 -5(4) . . . . ?
C2 C1 N2 N3 179(2) . . . . ?
N5 C1 N2 Cu1 135(3) . . . . ?
C2 C1 N2 Cu1 -41(3) . . . . ?
O1 C14 N3 N2 171(3) . . . . ?
N4 C14 N3 N2 -19(4) . . . . ?
O1 C14 N3 C15A -3(4) . . . . ?
N4 C14 N3 C15A 166(2) . . . . ?
C1 N2 N3 C14 16(4) . . . . ?
Cu1 N2 N3 C14 -114(3) . . . . ?
C1 N2 N3 C15A -169(2) . . . . ?
Cu1 N2 N3 C15A 60(3) . . . . ?
C17A C15A N3 C14 168(3) . . . . ?
C16A C15A N3 C14 -71(3) . . . . ?
C17A C15A N3 N2 -7(4) . . . . ?
C16A C15A N3 N2 114(2) . . . . ?
O1 C14 N4 N5 -178(3) . . . . ?
N3 C14 N4 N5 11(4) . . . . ?
O1 C14 N4 C15 1(4) . . . . ?
N3 C14 N4 C15 -169(2) . . . . ?
C16 C15 N4 N5 -62(3) . . . . ?
C17 C15 N4 N5 62(3) . . . . ?
C16 C15 N4 C14 118(3) . . . . ?
C17 C15 N4 C14 -117(3) . . . . ?
C14 N4 N5 C1 -2(4) . . . . ?
C15 N4 N5 C1 179(2) . . . . ?
N2 C1 N5 N4 -2(4) . . . . ?
C2 C1 N5 N4 175(3) . . . . ?
C25 C26 N6 C22 -5(4) . . . . ?
C25 C26 N6 Cu2 -167.4(18) . . . . ?
C23 C22 N6 C26 4(4) . . . . ?
C21 C22 N6 C26 -169(2) . . . . ?
C23 C22 N6 Cu2 169(2) . . . . ?
C21 C22 N6 Cu2 -4(3) . . . . ?
N10 C21 N7 N8 5(4) . . . . ?
C22 C21 N7 N8 -179(2) . . . . ?
N10 C21 N7 Cu2 -138(3) . . . . ?
C22 C21 N7 Cu2 38(2) . . . . ?
C21 N7 N8 C34 -13(4) . . . . ?
Cu2 N7 N8 C34 123(2) . . . . ?
C21 N7 N8 C35A 164(2) . . . . ?
Cu2 N7 N8 C35A -61(3) . . . . ?
O2 C34 N8 N7 -173(3) . . . . ?
N9 C34 N8 N7 13(4) . . . . ?
O2 C34 N8 C35A 10(4) . . . . ?
N9 C34 N8 C35A -164(2) . . . . ?
C37A C35A N8 N7 -105(3) . . . . ?
C36A C35A N8 N7 18(4) . . . . ?
C37A C35A N8 C34 71(3) . . . . ?
C36A C35A N8 C34 -165(2) . . . . ?
O2 C34 N9 N10 -178(3) . . . . ?
N8 C34 N9 N10 -5(4) . . . . ?
O2 C34 N9 C35 -4(5) . . . . ?
N8 C34 N9 C35 169(2) . . . . ?
C37 C35 N9 C34 -113(3) . . . . ?
C36 C35 N9 C34 125(3) . . . . ?
C37 C35 N9 N10 61(3) . . . . ?
C36 C35 N9 N10 -60(3) . . . . ?
N7 C21 N10 N9 3(4) . . . . ?
C22 C21 N10 N9 -173(2) . . . . ?
C34 N9 N10 C21 -2(4) . . . . ?
C35 N9 N10 C21 -176(2) . . . . ?

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.097


# start Validation Reply Form
_vrf_RINTA01_ATE80               
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The overall quality of the data are poor due to the crystal 
quality/instability
;
_vrf_PLAT020_ATE80               
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.327 Report
RESPONSE: The overall quality of the data are poor due to the crystal
 quality/instability
;
_vrf_PLAT026_ATE80               
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         36 %     
RESPONSE: low diffraction intensities in general and specially after
 2theta of 45
;
_vrf_PLAT341_ATE80               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03722 Ang.  
RESPONSE: The overall quality of the data are poor due to the crystal
 quality/instability
;
# end Validation Reply Form
####################################################################### 
# 
# 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_45-ald
_database_code_depnum_ccdc_archive 'CCDC 1532177'
_audit_update_record             
;
2017-12-14 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline-3-carbaldehyde
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H15 N O'
_chemical_formula_sum            'C13 H15 N O'
_exptl_crystal_recrystallization_method ethylacetate
_chemical_melting_point          ?

_exptl_crystal_description       cube
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         201.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-x+1/2, y+1/2, -z+3/4'
'-y, -x, -z+1/2'

_cell_length_a                   7.5168(4)
_cell_length_b                   7.5168(4)
_cell_length_c                   39.316(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2221.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8511
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      23.78

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.9543
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube, 12x0.4 mm long-fine focus'
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28194
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.1169
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.072
_diffrn_reflns_theta_max         25.156
_diffrn_reflns_theta_full        25.156
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1977
_reflns_number_gt                1336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.563
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.001

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=exp[3.0000(sinθ/λ)²)]/[σ²(Fo²)+(0.0892P)²+0.0400] where P=(0.1000Fo²+0.9000Fc²)'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
The Flack parameter was meaningless, -3(5), and has been erased.
;
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_h-m   'P 43 21 2'
_symmetry_int_tables_number      96
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1977
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.384
_refine_ls_restrained_S_all      1.384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4848(6) -0.1973(6) 0.08465(11) 0.0834(11) Uani 1 1 d . . . . .
H1 H 0.6044 -0.2012 0.0769 0.100 Uiso 1 1 calc R U . . .
C2 C 0.3828(5) -0.0350(5) 0.07750(9) 0.0660(9) Uani 1 1 d . . . . .
C3 C 0.2113(5) -0.0106(5) 0.08916(9) 0.0662(9) Uani 1 1 d . . . . .
H3 H 0.1563 -0.0993 0.1028 0.079 Uiso 1 1 calc R U . . .
C4 C 0.1200(4) 0.1426(5) 0.08098(8) 0.0606(8) Uani 1 1 d . . . . .
C5 C 0.2087(4) 0.2689(5) 0.06088(8) 0.0616(8) Uani 1 1 d . . . . .
C6 C 0.3820(5) 0.2333(5) 0.05095(9) 0.0700(10) Uani 1 1 d . . . . .
H6 H 0.4417 0.3205 0.0377 0.084 Uiso 1 1 calc R U . . .
C7 C 0.1084(5) 0.4333(5) 0.05233(9) 0.0697(9) Uani 1 1 d . . . . .
H7 H 0.1734 0.5241 0.0385 0.084 Uiso 1 1 calc R U . . .
C8 C -0.0842(5) 0.3850(5) 0.04007(8) 0.0678(9) Uani 1 1 d . . . . .
C9 C -0.1262(5) 0.3643(5) 0.07873(8) 0.0710(9) Uani 1 1 d . . . . .
H9 H -0.2482 0.4023 0.0858 0.085 Uiso 1 1 calc R U . . .
C10 C -0.0676(5) 0.1837(5) 0.09192(9) 0.0698(10) Uani 1 1 d . . . . .
H10A H -0.0746 0.1826 0.1171 0.084 Uiso 1 1 calc R U . . .
H10B H -0.1488 0.0907 0.0831 0.084 Uiso 1 1 calc R U . . .
C11 C 0.0228(6) 0.5003(6) 0.08587(11) 0.0814(11) Uani 1 1 d . . . . .
H11A H 0.0936 0.4749 0.1065 0.098 Uiso 1 1 calc R U . . .
H11B H -0.0165 0.6260 0.0852 0.098 Uiso 1 1 calc R U . . .
C12 C -0.1112(5) 0.2254(6) 0.01717(9) 0.0745(11) Uani 1 1 d . . . . .
H12A H -0.2383 0.1972 0.0159 0.112 Uiso 1 1 calc R U . . .
H12B H -0.0465 0.1231 0.0265 0.112 Uiso 1 1 calc R U . . .
H12C H -0.0661 0.2524 -0.0056 0.112 Uiso 1 1 calc R U . . .
C13 C -0.1763(6) 0.5455(6) 0.02440(12) 0.0912(13) Uani 1 1 d . . . . .
H13A H -0.1259 0.5691 0.0019 0.137 Uiso 1 1 calc R U . . .
H13B H -0.1584 0.6496 0.0390 0.137 Uiso 1 1 calc R U . . .
H13C H -0.3039 0.5213 0.0222 0.137 Uiso 1 1 calc R U . . .
N1 N 0.4705(4) 0.0857(4) 0.05867(8) 0.0728(9) Uani 1 1 d . . . . .
O1 O 0.4296(5) -0.3252(4) 0.09947(10) 0.1086(12) 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
C1 O1 1.199(5) . ?
C1 C2 1.468(5) . ?
C1 H1 0.9500 . ?
C2 N1 1.344(5) . ?
C2 C3 1.380(5) . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(5) . ?
C4 C10 1.506(5) . ?
C5 C6 1.386(5) . ?
C5 C7 1.486(5) . ?
C6 N1 1.329(5) . ?
C6 H6 0.9500 . ?
C7 C11 1.551(5) . ?
C7 C8 1.568(5) . ?
C7 H7 1.0000 . ?
C8 C12 1.514(6) . ?
C8 C13 1.522(5) . ?
C8 C9 1.560(5) . ?
C9 C10 1.519(5) . ?
C9 C11 1.542(6) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 125.4(4) . . ?
O1 C1 H1 117.3 . . ?
C2 C1 H1 117.3 . . ?
N1 C2 C3 123.5(3) . . ?
N1 C2 C1 114.2(3) . . ?
C3 C2 C1 122.3(4) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 117.4(3) . . ?
C3 C4 C10 124.8(3) . . ?
C5 C4 C10 117.8(3) . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 C7 125.0(3) . . ?
C4 C5 C7 116.7(3) . . ?
N1 C6 C5 124.6(3) . . ?
N1 C6 H6 117.7 . . ?
C5 C6 H6 117.7 . . ?
C5 C7 C11 106.8(3) . . ?
C5 C7 C8 110.2(3) . . ?
C11 C7 C8 87.3(3) . . ?
C5 C7 H7 116.3 . . ?
C11 C7 H7 116.3 . . ?
C8 C7 H7 116.3 . . ?
C12 C8 C13 109.1(3) . . ?
C12 C8 C9 118.3(3) . . ?
C13 C8 C9 112.4(3) . . ?
C12 C8 C7 119.3(3) . . ?
C13 C8 C7 111.1(3) . . ?
C9 C8 C7 84.9(2) . . ?
C10 C9 C11 108.7(3) . . ?
C10 C9 C8 111.3(3) . . ?
C11 C9 C8 88.0(3) . . ?
C10 C9 H9 115.3 . . ?
C11 C9 H9 115.3 . . ?
C8 C9 H9 115.3 . . ?
C4 C10 C9 110.9(3) . . ?
C4 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
C9 C11 C7 86.0(3) . . ?
C9 C11 H11A 114.3 . . ?
C7 C11 H11A 114.3 . . ?
C9 C11 H11B 114.3 . . ?
C7 C11 H11B 114.3 . . ?
H11A C11 H11B 111.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 N1 C2 116.4(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
O1 C1 C2 N1 -176.1(4) . . . . ?
O1 C1 C2 C3 3.6(6) . . . . ?
N1 C2 C3 C4 1.3(5) . . . . ?
C1 C2 C3 C4 -178.4(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C3 C4 C10 179.5(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C10 C4 C5 C6 179.4(3) . . . . ?
C3 C4 C5 C7 -179.9(3) . . . . ?
C10 C4 C5 C7 0.3(4) . . . . ?
C4 C5 C6 N1 1.1(5) . . . . ?
C7 C5 C6 N1 -179.9(3) . . . . ?
C6 C5 C7 C11 -132.2(4) . . . . ?
C4 C5 C7 C11 46.8(4) . . . . ?
C6 C5 C7 C8 134.4(4) . . . . ?
C4 C5 C7 C8 -46.6(4) . . . . ?
C5 C7 C8 C12 -40.1(4) . . . . ?
C11 C7 C8 C12 -147.0(3) . . . . ?
C5 C7 C8 C13 -168.4(3) . . . . ?
C11 C7 C8 C13 84.7(3) . . . . ?
C5 C7 C8 C9 79.6(3) . . . . ?
C11 C7 C8 C9 -27.3(3) . . . . ?
C12 C8 C9 C10 38.9(4) . . . . ?
C13 C8 C9 C10 167.5(3) . . . . ?
C7 C8 C9 C10 -81.8(3) . . . . ?
C12 C8 C9 C11 148.2(3) . . . . ?
C13 C8 C9 C11 -83.3(4) . . . . ?
C7 C8 C9 C11 27.5(3) . . . . ?
C3 C4 C10 C9 179.5(3) . . . . ?
C5 C4 C10 C9 -0.8(4) . . . . ?
C11 C9 C10 C4 -46.7(4) . . . . ?
C8 C9 C10 C4 48.5(4) . . . . ?
C10 C9 C11 C7 84.0(3) . . . . ?
C8 C9 C11 C7 -27.8(3) . . . . ?
C5 C7 C11 C9 -82.7(3) . . . . ?
C8 C7 C11 C9 27.6(3) . . . . ?
C5 C6 N1 C2 -0.1(5) . . . . ?
C3 C2 N1 C6 -1.1(5) . . . . ?
C1 C2 N1 C6 178.6(3) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.071

