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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aa156
_database_code_depnum_ccdc_archive 'CCDC 1983967'
loop_
_audit_author_name
_audit_author_address
'Abdullah M. Abudayyeh and Sally Brooker'
;University of Otago
New Zealand
;
_audit_update_record             
;
2020-02-14 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2020-02-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
'copper(II) complex of N5-donor diphenylamine macrocycle'
_chemical_formula_moiety         'C24 H24 Cu N5, B F4'
_chemical_formula_sum            'C24 H24 B Cu F4 N5'
_chemical_formula_weight         532.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         Cu
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.1780(7)
_cell_length_b                   18.9792(19)
_cell_length_c                   11.7456(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.602(8)
_cell_angle_gamma                90
_cell_volume                     2268.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2014
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.5340
_cell_measurement_theta_min      4.3830
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.787
_exptl_absorpt_coefficient_mu    1.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.099
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.1163
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9080
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.517
_diffrn_reflns_theta_min         4.428
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1725
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  37.00   1.00   20.00    --  -42.04  19.00 -60.00  119
  2  ω     25.00  68.00   1.00   20.00    --   42.04-125.00  90.00   43
  3  ω     28.00  81.00   1.00   20.00    --   42.04 -99.00-150.00   53
  4  ω     29.00 133.00   1.00   60.00    --  104.32 -30.00-150.00  104
  5  ω     94.00 178.00   1.00   60.00    --  104.32 125.00 -60.00   84
  6  ω     78.00 109.00   1.00   60.00    --  104.32  77.00   0.00   31
  7  ω     65.00  95.00   1.00   60.00    --  104.32-125.00 -30.00   30
  8  ω    133.00 170.00   1.00   60.00    --  104.32  77.00   0.00   37
  9  ω     22.00 106.00   1.00   60.00    --  104.32 -95.00  60.00   84
 10  ω     80.00 107.00   1.00   60.00    --  104.32 -61.00 -60.00   27
 11  ω     45.00  93.00   1.00   60.00    --  104.32 -95.00-120.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1199079000
_diffrn_orient_matrix_UB_12      0.0032644000
_diffrn_orient_matrix_UB_13      -0.0826715000
_diffrn_orient_matrix_UB_21      -0.0227915000
_diffrn_orient_matrix_UB_22      -0.0796663000
_diffrn_orient_matrix_UB_23      0.0165240000
_diffrn_orient_matrix_UB_31      -0.0894647000
_diffrn_orient_matrix_UB_32      0.0157168000
_diffrn_orient_matrix_UB_33      0.1004393000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2686
_reflns_number_total             4375
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.529
_refine_diff_density_min         -1.384
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4375
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.0928
_refine_ls_restrained_S_all      1.056
_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)+(0.0946P)²+10.5845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2237
_refine_ls_wR_factor_ref         0.2627
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 B1-F11 \\sim B1-F12 \\sim B1-F13 \\sim B1-F14
 with sigma of 0.01
 F11-F12 \\sim F11-F13 \\sim F11-F14 \\sim F12-F13 \\sim F12-F14 \\sim F13-F14
 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B), C11(H11A,H11B), C19(H19A,H19B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C3(H3), C16(H16), C5(H5), C12(H12), C17(H17), C21(H21),
 C22(H22), C4(H4), C15(H15), C24(H24), C14(H14), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.70288(9) 0.80265(6) 0.45029(9) 0.0329(3) Uani 1 1 d . . . . .
N5 N 0.7166(6) 0.8371(4) 0.2680(5) 0.0341(14) Uani 1 1 d . . . . .
N3 N 0.9086(5) 0.8109(4) 0.4416(5) 0.0365(15) Uani 1 1 d . . . . .
N1 N 0.5159(6) 0.7918(3) 0.4734(5) 0.0332(13) Uani 1 1 d . . . . .
N4 N 0.7106(6) 0.8991(4) 0.5044(5) 0.0364(14) Uani 1 1 d . . . . .
N2 N 0.7385(6) 0.7020(4) 0.4480(5) 0.0383(15) Uani 1 1 d . . . . .
C1 C 0.4547(6) 0.7374(4) 0.4139(6) 0.0314(16) Uani 1 1 d . . . . .
C7 C 0.6510(7) 0.6547(4) 0.4304(6) 0.0340(16) Uani 1 1 d . . . . .
H7 H 0.675490 0.607680 0.438287 0.041 Uiso 1 1 calc R . . . .
C18 C 0.4479(6) 0.8340(4) 0.5452(6) 0.0331(16) Uani 1 1 d . . . . .
C2 C 0.3287(7) 0.7469(4) 0.3602(6) 0.0352(17) Uani 1 1 d . . . . .
H2 H 0.288361 0.790788 0.364174 0.042 Uiso 1 1 calc R . . . .
C20 C 0.8443(6) 0.8484(4) 0.2447(6) 0.0328(16) Uani 1 1 d . . . . .
C3 C 0.2659(7) 0.6940(5) 0.3033(7) 0.0405(18) Uani 1 1 d . . . . .
H3 H 0.184443 0.702588 0.268144 0.049 Uiso 1 1 calc R . . . .
C6 C 0.5152(6) 0.6706(4) 0.3987(6) 0.0338(16) Uani 1 1 d . . . . .
C13 C 0.4948(7) 0.9009(4) 0.5836(6) 0.0361(17) Uani 1 1 d . . . . .
C16 C 0.2542(7) 0.8533(5) 0.6609(6) 0.0388(18) Uani 1 1 d . . . . .
H16 H 0.174725 0.836559 0.687142 0.047 Uiso 1 1 calc R . . . .
C10 C 0.9445(7) 0.8776(5) 0.5007(7) 0.043(2) Uani 1 1 d . . . . .
H10A H 1.026740 0.895117 0.472112 0.052 Uiso 1 1 calc R . . . .
H10B H 0.956781 0.868664 0.581643 0.052 Uiso 1 1 calc R . . . .
C5 C 0.4445(7) 0.6168(4) 0.3422(6) 0.0375(18) Uani 1 1 d . . . . .
H5 H 0.483153 0.572592 0.335868 0.045 Uiso 1 1 calc R . . . .
C12 C 0.6198(7) 0.9316(4) 0.5564(6) 0.0372(17) Uani 1 1 d . . . . .
H12 H 0.635463 0.978014 0.578066 0.045 Uiso 1 1 calc R . . . .
C17 C 0.3262(7) 0.8119(5) 0.5912(6) 0.0366(17) Uani 1 1 d . . . . .
H17 H 0.294701 0.767227 0.572861 0.044 Uiso 1 1 calc R . . . .
C8 C 0.8777(7) 0.6825(5) 0.4639(7) 0.0411(19) Uani 1 1 d . . . . .
H8A H 0.911466 0.664991 0.392778 0.049 Uiso 1 1 calc R . . . .
H8B H 0.886587 0.645438 0.520491 0.049 Uiso 1 1 calc R . . . .
C21 C 0.8790(8) 0.8908(5) 0.1526(6) 0.0407(19) Uani 1 1 d . . . . .
H21 H 0.966854 0.897488 0.135622 0.049 Uiso 1 1 calc R . . . .
C22 C 0.7806(8) 0.9223(4) 0.0877(6) 0.0399(18) Uani 1 1 d . . . . .
H22 H 0.801712 0.950377 0.025996 0.048 Uiso 1 1 calc R . . . .
C4 C 0.3211(7) 0.6268(5) 0.2964(7) 0.0411(19) Uani 1 1 d . . . . .
H4 H 0.275075 0.589945 0.261648 0.049 Uiso 1 1 calc R . . . .
C15 C 0.2972(8) 0.9203(5) 0.6937(7) 0.044(2) Uani 1 1 d . . . . .
H15 H 0.246688 0.948841 0.739738 0.053 Uiso 1 1 calc R . . . .
C24 C 0.6240(7) 0.8688(4) 0.2066(6) 0.0371(17) Uani 1 1 d . . . . .
H24 H 0.536911 0.861855 0.225848 0.044 Uiso 1 1 calc R . . . .
C11 C 0.8381(7) 0.9326(5) 0.4821(7) 0.0411(18) Uani 1 1 d . . . . .
H11A H 0.852918 0.972021 0.533353 0.049 Uiso 1 1 calc R . . . .
H11B H 0.838961 0.949895 0.404438 0.049 Uiso 1 1 calc R . . . .
C19 C 0.9429(7) 0.8103(5) 0.3193(6) 0.0385(18) Uani 1 1 d . . . . .
H19A H 0.949163 0.761795 0.293782 0.046 Uiso 1 1 calc R . . . .
H19B H 1.028469 0.831937 0.311297 0.046 Uiso 1 1 calc R . . . .
C9 C 0.9549(7) 0.7469(5) 0.5026(7) 0.043(2) Uani 1 1 d . . . . .
H9A H 0.945190 0.753427 0.583838 0.052 Uiso 1 1 calc R . . . .
H9B H 1.047388 0.739646 0.488716 0.052 Uiso 1 1 calc R . . . .
C14 C 0.4167(8) 0.9427(5) 0.6556(7) 0.0427(19) Uani 1 1 d . . . . .
H14 H 0.447479 0.986918 0.677860 0.051 Uiso 1 1 calc R . . . .
C23 C 0.6495(8) 0.9121(5) 0.1145(7) 0.0405(18) Uani 1 1 d . . . . .
H23 H 0.581779 0.933401 0.072405 0.049 Uiso 1 1 calc R . . . .
B1 B 0.7370(6) 0.5685(3) 0.7096(6) 0.042(2) Uani 1 1 d D . . . .
F11 F 0.6583(6) 0.5454(3) 0.7914(5) 0.082(2) Uani 1 1 d D . . . .
F12 F 0.6979(13) 0.5362(3) 0.6123(6) 0.189(7) Uani 1 1 d D . . A 1
F13 F 0.8592(6) 0.5522(5) 0.7359(11) 0.242(10) Uani 1 1 d D . . B 1
F14 F 0.7214(6) 0.6378(3) 0.6916(4) 0.0626(15) Uani 1 1 d D . . C 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N5 2.247(6) . ?
Cu1 N3 2.106(5) . ?
Cu1 N1 1.940(6) . ?
Cu1 N4 1.939(7) . ?
Cu1 N2 1.944(7) . ?
N5 C20 1.354(8) . ?
N5 C24 1.317(10) . ?
N3 C10 1.484(11) . ?
N3 C19 1.487(9) . ?
N3 C9 1.480(11) . ?
N1 C1 1.385(10) . ?
N1 C18 1.366(9) . ?
N4 C12 1.279(9) . ?
N4 C11 1.475(9) . ?
N2 C7 1.278(10) . ?
N2 C8 1.472(9) . ?
C1 C2 1.424(10) . ?
C1 C6 1.422(11) . ?
C7 H7 0.9300 . ?
C7 C6 1.454(10) . ?
C18 C13 1.425(12) . ?
C18 C17 1.428(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(12) . ?
C20 C21 1.400(11) . ?
C20 C19 1.501(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(12) . ?
C6 C5 1.406(11) . ?
C13 C12 1.443(10) . ?
C13 C14 1.420(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.363(11) . ?
C16 C15 1.395(12) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.515(11) . ?
C5 H5 0.9300 . ?
C5 C4 1.366(12) . ?
C12 H12 0.9300 . ?
C17 H17 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.517(12) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(12) . ?
C22 H22 0.9300 . ?
C22 C23 1.393(11) . ?
C4 H4 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.375(11) . ?
C24 H24 0.9300 . ?
C24 C23 1.388(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 H14 0.9300 . ?
C23 H23 0.9300 . ?
B1 F11 1.342(6) . ?
B1 F12 1.348(7) . ?
B1 F13 1.310(6) . ?
B1 F14 1.341(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N5 81.0(2) . . ?
N1 Cu1 N5 104.6(2) . . ?
N1 Cu1 N3 174.4(3) . . ?
N1 Cu1 N2 94.7(3) . . ?
N4 Cu1 N5 92.0(3) . . ?
N4 Cu1 N3 85.1(3) . . ?
N4 Cu1 N1 94.9(3) . . ?
N4 Cu1 N2 157.9(3) . . ?
N2 Cu1 N5 104.8(2) . . ?
N2 Cu1 N3 83.5(3) . . ?
C20 N5 Cu1 109.0(5) . . ?
C24 N5 Cu1 126.4(4) . . ?
C24 N5 C20 119.6(6) . . ?
C10 N3 Cu1 105.8(4) . . ?
C10 N3 C19 113.5(6) . . ?
C19 N3 Cu1 107.9(4) . . ?
C9 N3 Cu1 102.6(4) . . ?
C9 N3 C10 113.7(6) . . ?
C9 N3 C19 112.4(6) . . ?
C1 N1 Cu1 116.0(4) . . ?
C18 N1 Cu1 122.7(5) . . ?
C18 N1 C1 121.3(6) . . ?
C12 N4 Cu1 126.0(5) . . ?
C12 N4 C11 121.9(7) . . ?
C11 N4 Cu1 112.1(5) . . ?
C7 N2 Cu1 124.3(5) . . ?
C7 N2 C8 120.4(7) . . ?
C8 N2 Cu1 115.2(5) . . ?
N1 C1 C2 121.0(7) . . ?
N1 C1 C6 122.5(7) . . ?
C6 C1 C2 116.4(7) . . ?
N2 C7 H7 118.4 . . ?
N2 C7 C6 123.2(7) . . ?
C6 C7 H7 118.4 . . ?
N1 C18 C13 123.1(6) . . ?
N1 C18 C17 121.5(7) . . ?
C13 C18 C17 115.3(6) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 122.0(7) . . ?
C3 C2 H2 119.0 . . ?
N5 C20 C21 120.8(7) . . ?
N5 C20 C19 115.8(6) . . ?
C21 C20 C19 123.3(6) . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(8) . . ?
C4 C3 H3 119.3 . . ?
C1 C6 C7 124.5(7) . . ?
C5 C6 C1 119.3(7) . . ?
C5 C6 C7 116.1(7) . . ?
C18 C13 C12 125.4(6) . . ?
C14 C13 C18 119.9(6) . . ?
C14 C13 C12 114.7(7) . . ?
C17 C16 H16 119.3 . . ?
C17 C16 C15 121.4(7) . . ?
C15 C16 H16 119.3 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 C11 110.8(6) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C6 C5 H5 118.8 . . ?
C4 C5 C6 122.5(8) . . ?
C4 C5 H5 118.8 . . ?
N4 C12 C13 124.4(7) . . ?
N4 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C18 C17 H17 118.5 . . ?
C16 C17 C18 123.0(8) . . ?
C16 C17 H17 118.5 . . ?
N2 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
N2 C8 C9 108.8(7) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.7(7) . . ?
C22 C21 H21 120.6 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(7) . . ?
C23 C22 H22 120.0 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(8) . . ?
C5 C4 H4 120.9 . . ?
C16 C15 H15 121.1 . . ?
C14 C15 C16 117.7(7) . . ?
C14 C15 H15 121.1 . . ?
N5 C24 H24 118.3 . . ?
N5 C24 C23 123.4(7) . . ?
C23 C24 H24 118.3 . . ?
N4 C11 C10 107.9(7) . . ?
N4 C11 H11A 110.1 . . ?
N4 C11 H11B 110.1 . . ?
C10 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
N3 C19 C20 112.9(6) . . ?
N3 C19 H19A 109.0 . . ?
N3 C19 H19B 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
N3 C9 C8 111.2(7) . . ?
N3 C9 H9A 109.4 . . ?
N3 C9 H9B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C13 C14 H14 118.8 . . ?
C15 C14 C13 122.4(8) . . ?
C15 C14 H14 118.8 . . ?
C22 C23 H23 121.3 . . ?
C24 C23 C22 117.4(8) . . ?
C24 C23 H23 121.3 . . ?
F11 B1 F12 106.9(5) . . ?
F13 B1 F11 109.6(5) . . ?
F13 B1 F12 110.4(6) . . ?
F13 B1 F14 112.1(5) . . ?
F14 B1 F11 111.3(5) . . ?
F14 B1 F12 106.3(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.751
_oxdiff_exptl_absorpt_empirical_full_min 0.552
####################################################################### 
# 
# 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_aa254b
_database_code_depnum_ccdc_archive 'CCDC 1983968'
loop_
_audit_author_name
_audit_author_address
'Abdullah M. Abudayyeh and Sally Brooker'
;University of Otago
New Zealand
;
_audit_update_record             
;
2020-02-14 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2020-02-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
'copper(II) complex of N5-donor acyclic diphenylamine ligand'
_chemical_formula_moiety         'C28 H26 Cu N5, B F4'
_chemical_formula_sum            'C28 H26 B Cu F4 N5'
_chemical_formula_weight         582.89
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.2239(6)
_cell_length_b                   8.5237(4)
_cell_length_c                   20.9758(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.841(6)
_cell_angle_gamma                90
_cell_volume                     2543.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12782
_cell_measurement_temperature    100.02(11)
_cell_measurement_theta_max      72.8660
_cell_measurement_theta_min      4.4130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.714
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.359
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1196
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 5 3 0.3556
6 0 -13 0.0991
-2 -5 8 0.3203
6 0 7 0.0753
-6 0 -8 0.0580
3 -5 -3 0.4024
-4 1 13 0.1977
-5 -2 12 0.1978
-10 1 2 0.1262
-8 -1 -3 0.0922
-5 -1 -9 0.0656
-1 1 13 0.0750

_exptl_crystal_size_max          0.864
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.138
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.9914 4.9972 2.9910 -0.0025 -0.0746 -0.9894
5.9991 0.0031 -12.9882 0.2654 0.9298 0.2417
-2.0067 -4.9997 7.9976 -0.1394 -0.7582 0.7530
5.9883 -0.0024 7.0073 -0.9697 -0.0408 0.1882
-5.9877 0.0027 -8.0071 1.0315 0.0894 -0.1856
2.9927 -4.9971 -2.9925 0.0921 0.0248 0.9549
-4.0008 0.9963 12.9906 -0.4797 -0.7761 -0.3414
-5.0019 -2.0020 11.9908 -0.2230 -0.9396 0.1328
-9.9869 0.9998 1.9842 0.7371 -0.5412 -0.5189
-7.9888 -0.9981 -3.0107 0.9370 -0.3070 -0.0992
-4.9895 -0.9967 -9.0049 1.0388 0.1337 0.0203
-1.0047 0.9960 12.9951 -0.7484 -0.6267 -0.2379

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23142
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.612
_diffrn_reflns_theta_min         4.442
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3449
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00  -1.00   1.00    2.00    --  -41.67 -19.00 120.00  121
  2  ω    -66.00  33.00   1.00    2.00    --  -41.67  38.00 -60.00   99
  3  ω      1.00  83.00   1.00    2.00    --   41.67 -99.00  30.00   82
  4  ω     32.00 133.00   1.00    8.00    --  104.32 -61.00 120.00  101
  5  ω     22.00 109.00   1.00    8.00    --  104.32 -95.00 -30.00   87
  6  ω     31.00 130.00   1.00    8.00    --  104.32 -45.00  60.00   99
  7  ω     94.00 178.00   1.00    8.00    --  104.32 125.00-180.00   84
  8  ω     52.00 178.00   1.00    8.00    --  104.32  15.00 -90.00  126
  9  ω     31.00 117.00   1.00    8.00    --  104.32-125.00 120.00   86
 10  ω   -114.00 -14.00   1.00    2.00    --  -41.67 -57.00 -30.00  100
 11  ω   -118.00  -9.00   1.00    2.00    --  -41.67 -77.00 -90.00  109
 12  ω     52.00 178.00   1.00    8.00    --  104.32  15.00  90.00  126
 13  ω     78.00 177.00   1.00    8.00    --  104.32  45.00 -30.00   99
 14  ω     31.00 117.00   1.00    8.00    --  104.32-125.00 -60.00   86
 15  ω     75.00 177.00   1.00    8.00    --  104.32  61.00 150.00  102
 16  ω   -118.00  -9.00   1.00    2.00    --  -41.67 -77.00  90.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0896003000
_diffrn_orient_matrix_UB_12      -0.0350675000
_diffrn_orient_matrix_UB_13      -0.0618316000
_diffrn_orient_matrix_UB_21      0.0499585000
_diffrn_orient_matrix_UB_22      0.0540101000
_diffrn_orient_matrix_UB_23      -0.0485021000
_diffrn_orient_matrix_UB_31      0.0345275000
_diffrn_orient_matrix_UB_32      -0.1687933000
_diffrn_orient_matrix_UB_33      -0.0027013000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4671
_reflns_number_total             4989
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.012
_refine_diff_density_min         -1.386
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.071
_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)+(0.0450P)²+11.4252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1526
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C20(H20A,H20B), C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C22(H22), C7(H7), C24(H24), C27(H27), C2(H2), C15(H15), C25(H25),
 C5(H5), C14(H14), C13(H13), C17(H17), C3(H3), C26(H26), C4(H4), C16(H16),
 C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.57036(3) 0.66666(6) 0.28743(3) 0.02396(16) Uani 1 1 d . . . . .
F1 F 0.31301(16) 0.5293(3) 0.06384(12) 0.0388(6) Uani 1 1 d . . . . .
F4 F 0.24592(16) 0.5731(3) 0.14361(12) 0.0422(6) Uani 1 1 d . . . . .
N5 N 0.44651(19) 0.8064(3) 0.23429(16) 0.0237(6) Uani 1 1 d . . . . .
N2 N 0.5246(2) 0.4961(4) 0.21861(16) 0.0262(6) Uani 1 1 d . . . . .
N1 N 0.69184(19) 0.6624(4) 0.27334(16) 0.0240(6) Uani 1 1 d . . . . .
F2 F 0.1556(2) 0.5667(6) 0.03401(14) 0.0860(14) Uani 1 1 d . . . . .
N4 N 0.6196(2) 0.8359(4) 0.35586(16) 0.0266(7) Uani 1 1 d . . . . .
N3 N 0.5382(2) 0.5207(4) 0.36316(16) 0.0261(6) Uani 1 1 d . . . . .
F3 F 0.2222(3) 0.3452(4) 0.0874(3) 0.0919(14) Uani 1 1 d . . . . .
C28 C 0.7749(2) 0.6640(4) 0.32844(19) 0.0232(7) Uani 1 1 d . . . . .
C19 C 0.4093(2) 0.9009(4) 0.27000(19) 0.0245(7) Uani 1 1 d . . . . .
C23 C 0.7809(2) 0.7408(4) 0.38987(19) 0.0250(7) Uani 1 1 d . . . . .
C1 C 0.6915(2) 0.6655(4) 0.20768(19) 0.0236(7) Uani 1 1 d . . . . .
C18 C 0.3349(2) 1.0008(5) 0.2376(2) 0.0295(8) Uani 1 1 d . . . . .
H18 H 0.309395 1.062458 0.263212 0.035 Uiso 1 1 calc R . . . .
C22 C 0.7060(2) 0.8375(4) 0.39619(19) 0.0258(7) Uani 1 1 d . . . . .
H22 H 0.721962 0.907000 0.432724 0.031 Uiso 1 1 calc R . . . .
C6 C 0.6167(2) 0.5953(4) 0.15325(19) 0.0261(8) Uani 1 1 d . . . . .
C7 C 0.5461(2) 0.4985(4) 0.16428(19) 0.0266(8) Uani 1 1 d . . . . .
H7 H 0.512783 0.431357 0.129040 0.032 Uiso 1 1 calc R . . . .
C10 C 0.4638(3) 0.4217(4) 0.3421(2) 0.0286(8) Uani 1 1 d . . . . .
C24 C 0.8646(2) 0.7344(4) 0.4476(2) 0.0276(8) Uani 1 1 d . . . . .
H24 H 0.867332 0.785004 0.487525 0.033 Uiso 1 1 calc R . . . .
C27 C 0.8562(2) 0.5857(4) 0.3280(2) 0.0277(8) Uani 1 1 d . . . . .
H27 H 0.855278 0.536083 0.288318 0.033 Uiso 1 1 calc R . . . .
C21 C 0.5571(3) 0.9531(5) 0.3694(2) 0.0294(8) Uani 1 1 d . . . . .
H21A H 0.559854 1.049722 0.345796 0.035 Uiso 1 1 calc R . . . .
H21B H 0.579281 0.975506 0.417941 0.035 Uiso 1 1 calc R . . . .
C2 C 0.7614(3) 0.7440(5) 0.1904(2) 0.0286(8) Uani 1 1 d . . . . .
H2 H 0.812377 0.787724 0.224922 0.034 Uiso 1 1 calc R . . . .
C20 C 0.4554(2) 0.8971(5) 0.34650(19) 0.0281(8) Uani 1 1 d . . . . .
H20A H 0.453733 0.790858 0.362600 0.034 Uiso 1 1 calc R . . . .
H20B H 0.420492 0.963651 0.366607 0.034 Uiso 1 1 calc R . . . .
C15 C 0.4095(2) 0.8126(4) 0.16593(19) 0.0274(8) Uani 1 1 d . . . . .
H15 H 0.434190 0.746747 0.141155 0.033 Uiso 1 1 calc R . . . .
C25 C 0.9421(3) 0.6547(5) 0.4457(2) 0.0310(8) Uani 1 1 d . . . . .
H25 H 0.996770 0.650043 0.484052 0.037 Uiso 1 1 calc R . . . .
C5 C 0.6139(3) 0.6121(5) 0.0858(2) 0.0303(8) Uani 1 1 d . . . . .
H5 H 0.564502 0.566796 0.050633 0.036 Uiso 1 1 calc R . . . .
C9 C 0.4030(2) 0.4276(5) 0.2682(2) 0.0312(8) Uani 1 1 d . . . . .
H9A H 0.379655 0.533677 0.256612 0.037 Uiso 1 1 calc R . . . .
H9B H 0.349229 0.359230 0.260483 0.037 Uiso 1 1 calc R . . . .
C14 C 0.5963(3) 0.5124(5) 0.4283(2) 0.0296(8) Uani 1 1 d . . . . .
H14 H 0.646324 0.582358 0.443074 0.036 Uiso 1 1 calc R . . . .
C13 C 0.5860(3) 0.4056(5) 0.4748(2) 0.0341(9) Uani 1 1 d . . . . .
H13 H 0.629528 0.400901 0.519037 0.041 Uiso 1 1 calc R . . . .
C17 C 0.2987(3) 1.0089(5) 0.1672(2) 0.0328(8) Uani 1 1 d . . . . .
H17 H 0.250062 1.077809 0.144958 0.039 Uiso 1 1 calc R . . . .
C3 C 0.7561(3) 0.7577(5) 0.1235(2) 0.0322(8) Uani 1 1 d . . . . .
H3 H 0.803250 0.811103 0.113940 0.039 Uiso 1 1 calc R . . . .
C26 C 0.9370(3) 0.5808(5) 0.3850(2) 0.0318(9) Uani 1 1 d . . . . .
H26 H 0.989165 0.527231 0.382981 0.038 Uiso 1 1 calc R . . . .
C8 C 0.4555(3) 0.3776(4) 0.2216(2) 0.0292(8) Uani 1 1 d . . . . .
H8A H 0.487811 0.279348 0.238060 0.035 Uiso 1 1 calc R . . . .
H8B H 0.410558 0.359862 0.176005 0.035 Uiso 1 1 calc R . . . .
C4 C 0.6816(3) 0.6932(5) 0.0702(2) 0.0332(9) Uani 1 1 d . . . . .
H4 H 0.677734 0.704637 0.025187 0.040 Uiso 1 1 calc R . . . .
C16 C 0.3365(3) 0.9118(5) 0.1304(2) 0.0318(8) Uani 1 1 d . . . . .
H16 H 0.313364 0.913391 0.082939 0.038 Uiso 1 1 calc R . . . .
C11 C 0.4470(3) 0.3161(5) 0.3874(2) 0.0345(9) Uani 1 1 d . . . . .
H11 H 0.393785 0.252670 0.372909 0.041 Uiso 1 1 calc R . . . .
C12 C 0.5094(3) 0.3062(5) 0.4538(2) 0.0376(9) Uani 1 1 d . . . . .
H12 H 0.500014 0.233701 0.483846 0.045 Uiso 1 1 calc R . . . .
B1 B 0.2342(3) 0.5046(6) 0.0811(2) 0.0332(10) 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 N5 2.173(3) . ?
Cu1 N2 1.992(3) . ?
Cu1 N1 1.974(3) . ?
Cu1 N4 1.984(3) . ?
Cu1 N3 2.206(3) . ?
F1 B1 1.388(5) . ?
F4 B1 1.387(5) . ?
N5 C19 1.354(5) . ?
N5 C15 1.342(5) . ?
N2 C7 1.293(5) . ?
N2 C8 1.475(5) . ?
N1 C28 1.376(5) . ?
N1 C1 1.376(5) . ?
F2 B1 1.358(5) . ?
N4 C22 1.287(5) . ?
N4 C21 1.476(4) . ?
N3 C10 1.354(5) . ?
N3 C14 1.339(5) . ?
F3 B1 1.383(6) . ?
C28 C23 1.419(5) . ?
C28 C27 1.409(5) . ?
C19 C18 1.386(5) . ?
C19 C20 1.506(5) . ?
C23 C22 1.450(5) . ?
C23 C24 1.413(5) . ?
C1 C6 1.426(5) . ?
C1 C2 1.409(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.382(6) . ?
C22 H22 0.9300 . ?
C6 C7 1.438(5) . ?
C6 C5 1.407(5) . ?
C7 H7 0.9300 . ?
C10 C9 1.497(6) . ?
C10 C11 1.398(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.373(5) . ?
C27 H27 0.9300 . ?
C27 C26 1.376(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.526(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C16 1.384(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.399(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.374(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.528(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.380(6) . ?
C17 H17 0.9300 . ?
C17 C16 1.389(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(6) . ?
C26 H26 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C4 H4 0.9300 . ?
C16 H16 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.381(6) . ?
C12 H12 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
N5 Cu1 N3 107.71(11) . . ?
N2 Cu1 N5 90.69(12) . . ?
N2 Cu1 N3 90.01(12) . . ?
N1 Cu1 N5 128.42(12) . . ?
N1 Cu1 N2 89.03(12) . . ?
N1 Cu1 N4 89.37(12) . . ?
N1 Cu1 N3 123.86(12) . . ?
N4 Cu1 N5 90.46(12) . . ?
N4 Cu1 N2 178.39(12) . . ?
N4 Cu1 N3 90.72(12) . . ?
C19 N5 Cu1 120.0(2) . . ?
C15 N5 Cu1 121.8(2) . . ?
C15 N5 C19 117.9(3) . . ?
C7 N2 Cu1 119.6(3) . . ?
C7 N2 C8 117.2(3) . . ?
C8 N2 Cu1 122.7(2) . . ?
C28 N1 Cu1 120.2(2) . . ?
C1 N1 Cu1 118.7(2) . . ?
C1 N1 C28 121.0(3) . . ?
C22 N4 Cu1 121.2(3) . . ?
C22 N4 C21 116.4(3) . . ?
C21 N4 Cu1 121.9(2) . . ?
C10 N3 Cu1 119.4(3) . . ?
C14 N3 Cu1 122.0(2) . . ?
C14 N3 C10 118.2(3) . . ?
N1 C28 C23 120.7(3) . . ?
N1 C28 C27 122.5(3) . . ?
C27 C28 C23 116.8(3) . . ?
N5 C19 C18 121.6(3) . . ?
N5 C19 C20 116.7(3) . . ?
C18 C19 C20 121.7(3) . . ?
C28 C23 C22 123.1(3) . . ?
C24 C23 C28 120.5(3) . . ?
C24 C23 C22 116.3(3) . . ?
N1 C1 C6 120.7(3) . . ?
N1 C1 C2 122.2(3) . . ?
C2 C1 C6 117.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
N4 C22 C23 126.0(3) . . ?
N4 C22 H22 117.0 . . ?
C23 C22 H22 117.0 . . ?
C1 C6 C7 122.8(3) . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 117.6(3) . . ?
N2 C7 C6 126.1(3) . . ?
N2 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
N3 C10 C9 117.1(3) . . ?
N3 C10 C11 120.9(4) . . ?
C11 C10 C9 122.0(4) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.1(4) . . ?
C25 C24 H24 119.4 . . ?
C28 C27 H27 119.2 . . ?
C26 C27 C28 121.7(4) . . ?
C26 C27 H27 119.2 . . ?
N4 C21 H21A 109.2 . . ?
N4 C21 H21B 109.2 . . ?
N4 C21 C20 112.3(3) . . ?
H21A C21 H21B 107.9 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(4) . . ?
C3 C2 H2 119.2 . . ?
C19 C20 C21 111.4(3) . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
N5 C15 H15 118.3 . . ?
N5 C15 C16 123.4(3) . . ?
C16 C15 H15 118.3 . . ?
C24 C25 H25 120.7 . . ?
C24 C25 C26 118.6(3) . . ?
C26 C25 H25 120.7 . . ?
C6 C5 H5 118.9 . . ?
C4 C5 C6 122.3(4) . . ?
C4 C5 H5 118.9 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C10 C9 C8 112.4(3) . . ?
H9A C9 H9B 107.9 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
N3 C14 H14 118.1 . . ?
N3 C14 C13 123.7(4) . . ?
C13 C14 H14 118.1 . . ?
C14 C13 H13 120.9 . . ?
C12 C13 C14 118.2(4) . . ?
C12 C13 H13 120.9 . . ?
C18 C17 H17 120.7 . . ?
C18 C17 C16 118.5(4) . . ?
C16 C17 H17 120.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C27 C26 C25 121.3(3) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
N2 C8 C9 112.3(3) . . ?
N2 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C15 C16 C17 118.5(4) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(4) . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
F4 B1 F1 110.5(3) . . ?
F2 B1 F1 111.7(4) . . ?
F2 B1 F4 107.9(4) . . ?
F2 B1 F3 109.9(4) . . ?
F3 B1 F1 109.2(4) . . ?
F3 B1 F4 107.5(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.024
_oxdiff_exptl_absorpt_empirical_full_min 0.686
