# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_xbp36
_database_code_depnum_ccdc_archive 'CCDC 1531601'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Co(B-Bn)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 Co N2 O2'
_chemical_formula_sum            'C34 H32 Co N2 O2'
_chemical_formula_weight         559.54

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   15.1696(16)
_cell_length_b                   16.2061(17)
_cell_length_c                   5.6087(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1378.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      31.43

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             586
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.656
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6935
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            23476
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.839
_diffrn_reflns_theta_max         31.717
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4637
_reflns_number_gt                4338
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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=1/[σ²(Fo²)+(0.0358P)²+0.1111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.011(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4637
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
Co1 Co 0.5000 0.5000 0.38225(5) 0.01525(7) Uani 1 2 d S T P . .
N1 N 0.58101(8) 0.43429(8) 0.5774(2) 0.0154(2) Uani 1 1 d . . . . .
O1 O 0.45478(8) 0.40919(6) 0.1994(2) 0.0185(2) Uani 1 1 d . . . . .
C1 C 0.36096(11) 0.29564(11) -0.0582(3) 0.0235(3) Uani 1 1 d . . . . .
H1 H 0.3329 0.3458 -0.0140 0.028 Uiso 1 1 calc R U . . .
C2 C 0.32066(13) 0.24408(12) -0.2233(4) 0.0309(4) Uani 1 1 d . . . . .
H2 H 0.2653 0.2589 -0.2901 0.037 Uiso 1 1 calc R U . . .
C3 C 0.36124(14) 0.17074(12) -0.2911(4) 0.0307(4) Uani 1 1 d . . . . .
H3 H 0.3343 0.1357 -0.4058 0.037 Uiso 1 1 calc R U . . .
C4 C 0.44130(13) 0.14934(11) -0.1895(3) 0.0267(4) Uani 1 1 d . . . . .
H4 H 0.4689 0.0991 -0.2342 0.032 Uiso 1 1 calc R U . . .
C5 C 0.48166(10) 0.20026(10) -0.0238(3) 0.0210(3) Uani 1 1 d . . . . .
H5 H 0.5365 0.1845 0.0444 0.025 Uiso 1 1 calc R U . . .
C6 C 0.44207(10) 0.27498(9) 0.0441(3) 0.0177(3) Uani 1 1 d . . . . .
C7 C 0.48431(9) 0.33382(9) 0.2143(3) 0.0155(3) Uani 1 1 d . . . . .
C8 C 0.54891(10) 0.30737(9) 0.3717(3) 0.0166(3) Uani 1 1 d . . . . .
H8 H 0.5654 0.2510 0.3598 0.020 Uiso 1 1 calc R U . . .
C9 C 0.59347(9) 0.35433(9) 0.5487(3) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.65644(10) 0.30802(10) 0.7090(3) 0.0194(3) Uani 1 1 d . . . . .
H10A H 0.6617 0.2509 0.6537 0.029 Uiso 1 1 calc R U . . .
H10B H 0.6340 0.3086 0.8728 0.029 Uiso 1 1 calc R U . . .
H10C H 0.7144 0.3346 0.7043 0.029 Uiso 1 1 calc R U . . .
C11 C 0.62688(10) 0.47764(9) 0.7723(3) 0.0176(3) Uani 1 1 d . . . . .
H11A H 0.6288 0.4410 0.9135 0.021 Uiso 1 1 calc R U . . .
H11B H 0.5924 0.5272 0.8162 0.021 Uiso 1 1 calc R U . . .
C12 C 0.72004(9) 0.50379(11) 0.7107(3) 0.0168(2) Uani 1 1 d . . . . .
C13 C 0.78822(11) 0.48882(12) 0.8694(3) 0.0260(4) Uani 1 1 d . . . . .
H13 H 0.7766 0.4599 1.0133 0.031 Uiso 1 1 calc R U . . .
C14 C 0.87346(12) 0.51558(14) 0.8208(3) 0.0334(5) Uani 1 1 d . . . . .
H14 H 0.9195 0.5050 0.9316 0.040 Uiso 1 1 calc R U . . .
C15 C 0.89139(11) 0.55751(11) 0.6117(4) 0.0270(3) Uani 1 1 d . . . . .
H15 H 0.9495 0.5764 0.5792 0.032 Uiso 1 1 calc R U . . .
C16 C 0.82419(11) 0.57181(11) 0.4499(3) 0.0238(3) Uani 1 1 d . . . . .
H16 H 0.8365 0.5998 0.3048 0.029 Uiso 1 1 calc R U . . .
C17 C 0.73872(11) 0.54545(10) 0.4988(3) 0.0215(3) Uani 1 1 d . . . . .
H17 H 0.6929 0.5559 0.3874 0.026 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 1.9203(11) 2_665 ?
Co1 O1 1.9203(11) . ?
Co1 N1 1.9602(13) 2_665 ?
Co1 N1 1.9603(13) . ?
N1 C9 1.320(2) . ?
N1 C11 1.4739(19) . ?
O1 C7 1.3037(17) . ?
C1 C2 1.389(2) . ?
C1 C6 1.398(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.494(2) . ?
C7 C8 1.387(2) . ?
C8 C9 1.422(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.511(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.515(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.386(2) . ?
C12 C17 1.396(2) . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O1 115.45(7) 2_665 . ?
O1 Co1 N1 96.08(5) 2_665 2_665 ?
O1 Co1 N1 119.38(5) . 2_665 ?
O1 Co1 N1 119.38(5) 2_665 . ?
O1 Co1 N1 96.07(5) . . ?
N1 Co1 N1 112.10(8) 2_665 . ?
C9 N1 C11 119.41(13) . . ?
C9 N1 Co1 123.72(11) . . ?
C11 N1 Co1 116.82(10) . . ?
C7 O1 Co1 124.13(10) . . ?
C2 C1 C6 121.11(16) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 120.09(18) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.29(17) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.94(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.43(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.14(15) . . ?
C1 C6 C7 119.13(14) . . ?
C5 C6 C7 122.71(14) . . ?
O1 C7 C8 124.97(13) . . ?
O1 C7 C6 114.19(13) . . ?
C8 C7 C6 120.84(13) . . ?
C7 C8 C9 127.94(13) . . ?
C7 C8 H8 116.0 . . ?
C9 C8 H8 116.0 . . ?
N1 C9 C8 122.88(14) . . ?
N1 C9 C10 120.37(14) . . ?
C8 C9 C10 116.74(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 113.87(13) . . ?
N1 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C17 118.67(14) . . ?
C13 C12 C11 120.06(14) . . ?
C17 C12 C11 121.24(14) . . ?
C12 C13 C14 120.91(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.15(16) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.57(16) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.36(17) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.33(16) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?

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
C6 C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C6 C7 177.85(17) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C4 C5 C6 C7 -177.45(16) . . . . ?
Co1 O1 C7 C8 3.6(2) . . . . ?
Co1 O1 C7 C6 -176.66(10) . . . . ?
C1 C6 C7 O1 -19.2(2) . . . . ?
C5 C6 C7 O1 158.90(15) . . . . ?
C1 C6 C7 C8 160.60(15) . . . . ?
C5 C6 C7 C8 -21.3(2) . . . . ?
O1 C7 C8 C9 1.9(3) . . . . ?
C6 C7 C8 C9 -177.89(14) . . . . ?
C11 N1 C9 C8 177.28(13) . . . . ?
Co1 N1 C9 C8 0.0(2) . . . . ?
C11 N1 C9 C10 -2.0(2) . . . . ?
Co1 N1 C9 C10 -179.28(10) . . . . ?
C7 C8 C9 N1 -3.8(2) . . . . ?
C7 C8 C9 C10 175.49(15) . . . . ?
C9 N1 C11 C12 83.84(18) . . . . ?
Co1 N1 C11 C12 -98.65(13) . . . . ?
N1 C11 C12 C13 -133.26(16) . . . . ?
N1 C11 C12 C17 48.8(2) . . . . ?
C17 C12 C13 C14 0.8(3) . . . . ?
C11 C12 C13 C14 -177.15(17) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C15 C16 C17 C12 -0.5(3) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C11 C12 C17 C16 177.46(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11B O1 0.99 2.49 3.2615(19) 134.6 2_666

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_xbp14
_database_code_depnum_ccdc_archive 'CCDC 1531606'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Ni(B-Et)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 Ni1 O2'
_chemical_formula_sum            'C24 H28 N2 Ni O2'
_chemical_formula_weight         435.19

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5160(5)
_cell_length_b                   12.6431(9)
_cell_length_c                   13.1097(14)
_cell_angle_alpha                118.470(2)
_cell_angle_beta                 101.607(2)
_cell_angle_gamma                95.514(2)
_cell_volume                     1045.70(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      31.62

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.950
_shelx_estimated_absorpt_T_min   0.825
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7064
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            34968
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         31.660
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6904
_reflns_number_gt                6169
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+0.0835P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6904
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.41212(2) 0.32665(2) 0.70238(2) 0.01207(4) Uani 1 1 d . . . . .
N1 N 0.29890(11) 0.41738(7) 0.83057(7) 0.01210(14) Uani 1 1 d . . . . .
N2 N 0.24188(11) 0.23788(7) 0.53875(7) 0.01295(14) Uani 1 1 d . . . . .
O1 O 0.60679(9) 0.46527(6) 0.75326(6) 0.01420(13) Uani 1 1 d . . . . .
O2 O 0.45811(10) 0.18215(6) 0.70632(6) 0.01553(13) Uani 1 1 d . . . . .
C1 C 0.85960(14) 0.78341(9) 0.96936(9) 0.01510(17) Uani 1 1 d . . . . .
H1 H 0.7946 0.8082 1.0293 0.018 Uiso 1 1 calc R U . . .
C2 C 1.02088(15) 0.86173(9) 0.98801(9) 0.01902(19) Uani 1 1 d . . . . .
H2 H 1.0663 0.9393 1.0609 0.023 Uiso 1 1 calc R U . . .
C3 C 1.11637(15) 0.82721(10) 0.90041(10) 0.0204(2) Uani 1 1 d . . . . .
H3 H 1.2260 0.8813 0.9131 0.024 Uiso 1 1 calc R U . . .
C4 C 1.05049(14) 0.71323(10) 0.79430(9) 0.01768(18) Uani 1 1 d . . . . .
H4 H 1.1153 0.6893 0.7343 0.021 Uiso 1 1 calc R U . . .
C5 C 0.88981(13) 0.63411(9) 0.77573(9) 0.01467(17) Uani 1 1 d . . . . .
H5 H 0.8461 0.5562 0.7031 0.018 Uiso 1 1 calc R U . . .
C6 C 0.79166(13) 0.66779(9) 0.86268(8) 0.01240(16) Uani 1 1 d . . . . .
C7 C 0.62285(12) 0.57757(8) 0.83996(8) 0.01165(16) Uani 1 1 d . . . . .
C8 C 0.49994(13) 0.61479(9) 0.90914(8) 0.01335(16) Uani 1 1 d . . . . .
H8 H 0.5192 0.7009 0.9634 0.016 Uiso 1 1 calc R U . . .
C9 C 0.34655(13) 0.53678(9) 0.90732(8) 0.01217(16) Uani 1 1 d . . . . .
C10 C 0.24465(14) 0.59928(9) 1.00085(9) 0.01583(17) Uani 1 1 d . . . . .
H10A H 0.1110 0.5788 0.9608 0.024 Uiso 1 1 calc R U . . .
H10B H 0.2916 0.6889 1.0435 0.024 Uiso 1 1 calc R U . . .
H10C H 0.2653 0.5706 1.0589 0.024 Uiso 1 1 calc R U . . .
C11 C 0.14643(13) 0.33919(9) 0.83530(9) 0.01475(17) Uani 1 1 d . . . . .
H11A H 0.1327 0.3792 0.9183 0.018 Uiso 1 1 calc R U . . .
H11B H 0.1779 0.2588 0.8162 0.018 Uiso 1 1 calc R U . . .
C12 C -0.03777(14) 0.31753(10) 0.74629(9) 0.01851(19) Uani 1 1 d . . . . .
H12A H -0.1346 0.2620 0.7491 0.028 Uiso 1 1 calc R U . . .
H12B H -0.0236 0.2802 0.6643 0.028 Uiso 1 1 calc R U . . .
H12C H -0.0735 0.3965 0.7683 0.028 Uiso 1 1 calc R U . . .
C13 C 0.48548(14) 0.00569(9) 0.77370(9) 0.01675(18) Uani 1 1 d . . . . .
H13 H 0.5114 0.0899 0.8355 0.020 Uiso 1 1 calc R U . . .
C14 C 0.51669(15) -0.08388(10) 0.80441(10) 0.0203(2) Uani 1 1 d . . . . .
H14 H 0.5634 -0.0603 0.8870 0.024 Uiso 1 1 calc R U . . .
C15 C 0.47989(15) -0.20739(10) 0.71497(11) 0.0206(2) Uani 1 1 d . . . . .
H15 H 0.4990 -0.2684 0.7361 0.025 Uiso 1 1 calc R U . . .
C16 C 0.41475(14) -0.24097(10) 0.59406(10) 0.01906(19) Uani 1 1 d . . . . .
H16 H 0.3911 -0.3251 0.5325 0.023 Uiso 1 1 calc R U . . .
C17 C 0.38412(13) -0.15205(9) 0.56295(9) 0.01532(17) Uani 1 1 d . . . . .
H17 H 0.3409 -0.1759 0.4801 0.018 Uiso 1 1 calc R U . . .
C18 C 0.41626(12) -0.02755(9) 0.65245(9) 0.01288(16) Uani 1 1 d . . . . .
C19 C 0.37531(12) 0.06974(8) 0.62278(8) 0.01215(16) Uani 1 1 d . . . . .
C20 C 0.25174(13) 0.03628(9) 0.51316(9) 0.01390(16) Uani 1 1 d . . . . .
H20 H 0.1997 -0.0495 0.4599 0.017 Uiso 1 1 calc R U . . .
C21 C 0.19400(13) 0.11644(9) 0.47149(8) 0.01282(16) Uani 1 1 d . . . . .
C22 C 0.07336(15) 0.05412(9) 0.34206(9) 0.01801(18) Uani 1 1 d . . . . .
H22A H -0.0449 0.0808 0.3405 0.027 Uiso 1 1 calc R U . . .
H22B H 0.0488 -0.0356 0.3068 0.027 Uiso 1 1 calc R U . . .
H22C H 0.1380 0.0769 0.2951 0.027 Uiso 1 1 calc R U . . .
C23 C 0.16491(14) 0.30775(9) 0.48332(9) 0.01642(18) Uani 1 1 d . . . . .
H23A H 0.0272 0.2863 0.4618 0.020 Uiso 1 1 calc R U . . .
H23B H 0.2007 0.2827 0.4077 0.020 Uiso 1 1 calc R U . . .
C24 C 0.23246(18) 0.44640(10) 0.56606(10) 0.0249(2) Uani 1 1 d . . . . .
H24A H 0.1759 0.4881 0.5255 0.037 Uiso 1 1 calc R U . . .
H24B H 0.3684 0.4687 0.5852 0.037 Uiso 1 1 calc R U . . .
H24C H 0.1967 0.4720 0.6409 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.9124(7) . ?
Ni1 O2 1.9141(7) . ?
Ni1 N1 1.9467(8) . ?
Ni1 N2 1.9551(8) . ?
N1 C9 1.3125(12) . ?
N1 C11 1.4709(12) . ?
N2 C21 1.3191(12) . ?
N2 C23 1.4779(12) . ?
O1 C7 1.3022(11) . ?
O2 C19 1.2956(11) . ?
C1 C2 1.3889(13) . ?
C1 C6 1.4048(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.3923(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3898(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3912(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.4004(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.4985(13) . ?
C7 C8 1.3824(13) . ?
C8 C9 1.4319(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.5116(13) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5251(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3954(14) . ?
C13 C18 1.4007(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.3895(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3924(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3901(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.4017(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.4966(13) . ?
C19 C20 1.3838(13) . ?
C20 C21 1.4250(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.5135(13) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.5172(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 Ni1 O2 122.87(3) . . ?
O1 Ni1 N1 94.33(3) . . ?
O2 Ni1 N1 108.19(3) . . ?
O1 Ni1 N2 121.34(3) . . ?
O2 Ni1 N2 95.65(3) . . ?
N1 Ni1 N2 115.14(3) . . ?
C9 N1 C11 120.62(8) . . ?
C9 N1 Ni1 125.77(7) . . ?
C11 N1 Ni1 113.61(6) . . ?
C21 N2 C23 116.76(8) . . ?
C21 N2 Ni1 123.50(6) . . ?
C23 N2 Ni1 119.70(6) . . ?
C7 O1 Ni1 125.65(6) . . ?
C19 O2 Ni1 125.12(6) . . ?
C2 C1 C6 120.59(9) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 120.36(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.67(9) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.13(9) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.87(9) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.38(9) . . ?
C5 C6 C7 118.74(8) . . ?
C1 C6 C7 122.85(8) . . ?
O1 C7 C8 124.84(9) . . ?
O1 C7 C6 114.46(8) . . ?
C8 C7 C6 120.70(8) . . ?
C7 C8 C9 126.65(9) . . ?
C7 C8 H8 116.7 . . ?
C9 C8 H8 116.7 . . ?
N1 C9 C8 122.12(8) . . ?
N1 C9 C10 121.66(8) . . ?
C8 C9 C10 116.20(8) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 111.70(8) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 120.54(10) . . ?
C14 C13 H13 119.7 . . ?
C18 C13 H13 119.7 . . ?
C15 C14 C13 120.40(10) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.45(9) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.38(10) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.72(9) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 118.48(9) . . ?
C13 C18 C19 119.28(9) . . ?
C17 C18 C19 122.23(9) . . ?
O2 C19 C20 124.75(9) . . ?
O2 C19 C18 115.58(8) . . ?
C20 C19 C18 119.65(8) . . ?
C19 C20 C21 127.08(9) . . ?
C19 C20 H20 116.5 . . ?
C21 C20 H20 116.5 . . ?
N2 C21 C20 123.50(9) . . ?
N2 C21 C22 120.54(8) . . ?
C20 C21 C22 115.96(8) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 C24 112.88(8) . . ?
N2 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
N2 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.75(15) . . . . ?
C1 C2 C3 C4 -0.58(16) . . . . ?
C2 C3 C4 C5 0.07(16) . . . . ?
C3 C4 C5 C6 0.29(15) . . . . ?
C4 C5 C6 C1 -0.13(14) . . . . ?
C4 C5 C6 C7 -178.09(8) . . . . ?
C2 C1 C6 C5 -0.39(14) . . . . ?
C2 C1 C6 C7 177.49(9) . . . . ?
Ni1 O1 C7 C8 -0.36(13) . . . . ?
Ni1 O1 C7 C6 178.67(6) . . . . ?
C5 C6 C7 O1 14.57(12) . . . . ?
C1 C6 C7 O1 -163.30(9) . . . . ?
C5 C6 C7 C8 -166.36(9) . . . . ?
C1 C6 C7 C8 15.77(13) . . . . ?
O1 C7 C8 C9 6.88(16) . . . . ?
C6 C7 C8 C9 -172.09(8) . . . . ?
C11 N1 C9 C8 176.93(8) . . . . ?
Ni1 N1 C9 C8 -3.77(13) . . . . ?
C11 N1 C9 C10 -1.68(13) . . . . ?
Ni1 N1 C9 C10 177.61(7) . . . . ?
C7 C8 C9 N1 -4.55(15) . . . . ?
C7 C8 C9 C10 174.14(9) . . . . ?
C9 N1 C11 C12 95.76(10) . . . . ?
Ni1 N1 C11 C12 -83.62(8) . . . . ?
C18 C13 C14 C15 0.15(15) . . . . ?
C13 C14 C15 C16 1.18(16) . . . . ?
C14 C15 C16 C17 -0.93(15) . . . . ?
C15 C16 C17 C18 -0.67(15) . . . . ?
C14 C13 C18 C17 -1.72(14) . . . . ?
C14 C13 C18 C19 176.99(9) . . . . ?
C16 C17 C18 C13 1.98(14) . . . . ?
C16 C17 C18 C19 -176.69(9) . . . . ?
Ni1 O2 C19 C20 5.58(13) . . . . ?
Ni1 O2 C19 C18 -172.59(6) . . . . ?
C13 C18 C19 O2 20.32(12) . . . . ?
C17 C18 C19 O2 -161.03(9) . . . . ?
C13 C18 C19 C20 -157.95(9) . . . . ?
C17 C18 C19 C20 20.70(13) . . . . ?
O2 C19 C20 C21 0.46(16) . . . . ?
C18 C19 C20 C21 178.56(9) . . . . ?
C23 N2 C21 C20 -177.94(9) . . . . ?
Ni1 N2 C21 C20 4.02(13) . . . . ?
C23 N2 C21 C22 2.81(13) . . . . ?
Ni1 N2 C21 C22 -175.22(7) . . . . ?
C19 C20 C21 N2 -5.73(16) . . . . ?
C19 C20 C21 C22 173.55(9) . . . . ?
C21 N2 C23 C24 -178.23(9) . . . . ?
Ni1 N2 C23 C24 -0.12(11) . . . . ?

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_xbp17
_database_code_depnum_ccdc_archive 'CCDC 1531598'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Cu(B-Et)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 Cu N2 O2'
_chemical_formula_sum            'C24 H28 Cu N2 O2'
_chemical_formula_weight         440.02

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.813(2)
_cell_length_b                   7.2285(13)
_cell_length_c                   23.157(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.407(2)
_cell_angle_gamma                90
_cell_volume                     2144.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    7527
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      29.41

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   0.6259
_exptl_transmission_factor_max   0.7459
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.040
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            30346
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.759
_diffrn_reflns_theta_max         29.658
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6026
_reflns_number_gt                4811
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.9273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6026
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.51188(2) 0.55551(3) 0.64087(2) 0.01807(8) Uani 1 1 d . . . . .
N1 N 0.49314(12) 0.3771(2) 0.57861(6) 0.0195(3) Uani 1 1 d . . . . .
N2 N 0.50391(12) 0.5860(2) 0.72440(7) 0.0192(3) Uani 1 1 d . . . . .
O1 O 0.39126(10) 0.69880(19) 0.62184(5) 0.0216(3) Uani 1 1 d . . . . .
O2 O 0.66057(10) 0.5571(2) 0.63790(6) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.25196(15) 0.9747(3) 0.60405(8) 0.0217(4) Uani 1 1 d . . . . .
H1 H 0.2911 0.9681 0.6390 0.026 Uiso 1 1 calc R U . . .
C2 C 0.18867(16) 1.1274(3) 0.59352(9) 0.0256(4) Uani 1 1 d . . . . .
H2 H 0.1853 1.2244 0.6211 0.031 Uiso 1 1 calc R U . . .
C3 C 0.13045(16) 1.1388(3) 0.54299(9) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.0871 1.2431 0.5358 0.034 Uiso 1 1 calc R U . . .
C4 C 0.13604(16) 0.9963(3) 0.50289(9) 0.0269(4) Uani 1 1 d . . . . .
H4 H 0.0965 1.0038 0.4681 0.032 Uiso 1 1 calc R U . . .
C5 C 0.19891(14) 0.8429(3) 0.51313(8) 0.0223(4) Uani 1 1 d . . . . .
H5 H 0.2013 0.7458 0.4856 0.027 Uiso 1 1 calc R U . . .
C6 C 0.25888(13) 0.8308(3) 0.56401(8) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.33411(13) 0.6754(3) 0.57551(7) 0.0171(3) Uani 1 1 d . . . . .
C8 C 0.34132(14) 0.5275(3) 0.53873(8) 0.0194(4) Uani 1 1 d . . . . .
H8 H 0.2909 0.5216 0.5085 0.023 Uiso 1 1 calc R U . . .
C9 C 0.41641(14) 0.3806(3) 0.54072(7) 0.0176(3) Uani 1 1 d . . . . .
C10 C 0.40421(15) 0.2315(3) 0.49548(8) 0.0228(4) Uani 1 1 d . . . . .
H10A H 0.3431 0.2585 0.4713 0.034 Uiso 1 1 calc R U . . .
H10B H 0.3949 0.1115 0.5144 0.034 Uiso 1 1 calc R U . . .
H10C H 0.4667 0.2278 0.4714 0.034 Uiso 1 1 calc R U . . .
C11 C 0.57011(16) 0.2257(3) 0.57881(8) 0.0254(4) Uani 1 1 d . . . . .
H11A H 0.6414 0.2785 0.5790 0.030 Uiso 1 1 calc R U . . .
H11B H 0.5617 0.1514 0.5432 0.030 Uiso 1 1 calc R U . . .
C12 C 0.55693(19) 0.1019(3) 0.63097(10) 0.0347(5) Uani 1 1 d . . . . .
H12A H 0.6108 0.0057 0.6308 0.052 Uiso 1 1 calc R U . . .
H12B H 0.4878 0.0441 0.6296 0.052 Uiso 1 1 calc R U . . .
H12C H 0.5637 0.1759 0.6663 0.052 Uiso 1 1 calc R U . . .
C13 C 0.86652(16) 0.5879(3) 0.61129(9) 0.0255(4) Uani 1 1 d . . . . .
H13 H 0.8147 0.6039 0.5822 0.031 Uiso 1 1 calc R U . . .
C14 C 0.97140(17) 0.5946(3) 0.59637(10) 0.0291(4) Uani 1 1 d . . . . .
H14 H 0.9905 0.6157 0.5574 0.035 Uiso 1 1 calc R U . . .
C15 C 1.04839(16) 0.5705(3) 0.63823(10) 0.0273(4) Uani 1 1 d . . . . .
H15 H 1.1201 0.5754 0.6282 0.033 Uiso 1 1 calc R U . . .
C16 C 1.01912(16) 0.5391(3) 0.69504(10) 0.0274(4) Uani 1 1 d . . . . .
H16 H 1.0712 0.5222 0.7239 0.033 Uiso 1 1 calc R U . . .
C17 C 0.91450(15) 0.5322(3) 0.71003(9) 0.0238(4) Uani 1 1 d . . . . .
H17 H 0.8959 0.5096 0.7490 0.029 Uiso 1 1 calc R U . . .
C18 C 0.83601(14) 0.5580(3) 0.66834(8) 0.0193(3) Uani 1 1 d . . . . .
C19 C 0.72182(14) 0.5563(3) 0.68280(8) 0.0190(3) Uani 1 1 d . . . . .
C20 C 0.68927(15) 0.5554(3) 0.73930(8) 0.0223(4) Uani 1 1 d . . . . .
H20 H 0.7423 0.5462 0.7680 0.027 Uiso 1 1 calc R U . . .
C21 C 0.58413(15) 0.5666(2) 0.75939(8) 0.0191(3) Uani 1 1 d . . . . .
C22 C 0.57081(16) 0.5563(3) 0.82438(8) 0.0234(4) Uani 1 1 d . . . . .
H22A H 0.6378 0.5252 0.8426 0.035 Uiso 1 1 calc R U . . .
H22B H 0.5193 0.4608 0.8337 0.035 Uiso 1 1 calc R U . . .
H22C H 0.5467 0.6762 0.8388 0.035 Uiso 1 1 calc R U . . .
C23 C 0.39781(15) 0.6104(3) 0.74692(8) 0.0251(4) Uani 1 1 d . . . . .
H23A H 0.3644 0.7174 0.7275 0.030 Uiso 1 1 calc R U . . .
H23B H 0.4017 0.6376 0.7888 0.030 Uiso 1 1 calc R U . . .
C24 C 0.33139(17) 0.4390(3) 0.73731(11) 0.0357(5) Uani 1 1 d . . . . .
H24A H 0.2598 0.4638 0.7497 0.054 Uiso 1 1 calc R U . . .
H24B H 0.3602 0.3360 0.7598 0.054 Uiso 1 1 calc R U . . .
H24C H 0.3314 0.4067 0.6962 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9069(14) . ?
Cu1 O1 1.9094(13) . ?
Cu1 N1 1.9481(16) . ?
Cu1 N2 1.9504(16) . ?
N1 C9 1.313(2) . ?
N1 C11 1.473(2) . ?
N2 C21 1.312(2) . ?
N2 C23 1.470(2) . ?
O1 C7 1.306(2) . ?
O2 C19 1.298(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.397(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.502(2) . ?
C7 C8 1.371(3) . ?
C8 C9 1.433(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.510(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.514(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.391(3) . ?
C13 C18 1.397(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.402(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.503(3) . ?
C19 C20 1.376(3) . ?
C20 C21 1.431(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.518(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.519(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
O2 Cu1 O1 142.71(6) . . ?
O2 Cu1 N1 95.47(6) . . ?
O1 Cu1 N1 95.34(6) . . ?
O2 Cu1 N2 95.42(6) . . ?
O1 Cu1 N2 96.86(6) . . ?
N1 Cu1 N2 143.31(7) . . ?
C9 N1 C11 120.96(16) . . ?
C9 N1 Cu1 124.72(13) . . ?
C11 N1 Cu1 114.23(12) . . ?
C21 N2 C23 121.08(16) . . ?
C21 N2 Cu1 123.66(13) . . ?
C23 N2 Cu1 114.87(12) . . ?
C7 O1 Cu1 124.59(12) . . ?
C19 O2 Cu1 124.72(12) . . ?
C2 C1 C6 120.98(18) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.34(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.37(19) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.66(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.41(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.24(17) . . ?
C1 C6 C7 118.86(16) . . ?
C5 C6 C7 122.82(16) . . ?
O1 C7 C8 124.87(16) . . ?
O1 C7 C6 113.85(15) . . ?
C8 C7 C6 121.26(16) . . ?
C7 C8 C9 127.30(17) . . ?
C7 C8 H8 116.3 . . ?
C9 C8 H8 116.3 . . ?
N1 C9 C8 122.34(17) . . ?
N1 C9 C10 121.54(17) . . ?
C8 C9 C10 116.10(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 111.29(16) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 121.17(19) . . ?
C14 C13 H13 119.4 . . ?
C18 C13 H13 119.4 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.08(19) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.82(19) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 117.89(18) . . ?
C13 C18 C19 119.42(17) . . ?
C17 C18 C19 122.69(17) . . ?
O2 C19 C20 125.16(17) . . ?
O2 C19 C18 113.91(16) . . ?
C20 C19 C18 120.93(17) . . ?
C19 C20 C21 126.98(17) . . ?
C19 C20 H20 116.5 . . ?
C21 C20 H20 116.5 . . ?
N2 C21 C20 122.72(17) . . ?
N2 C21 C22 121.64(17) . . ?
C20 C21 C22 115.63(16) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 C24 111.64(18) . . ?
N2 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
N2 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C1 C6 C7 175.71(17) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 -175.42(17) . . . . ?
Cu1 O1 C7 C8 11.2(3) . . . . ?
Cu1 O1 C7 C6 -167.13(11) . . . . ?
C1 C6 C7 O1 -4.0(2) . . . . ?
C5 C6 C7 O1 172.56(16) . . . . ?
C1 C6 C7 C8 177.61(17) . . . . ?
C5 C6 C7 C8 -5.9(3) . . . . ?
O1 C7 C8 C9 -5.5(3) . . . . ?
C6 C7 C8 C9 172.74(17) . . . . ?
C11 N1 C9 C8 -178.88(17) . . . . ?
Cu1 N1 C9 C8 4.9(3) . . . . ?
C11 N1 C9 C10 -0.6(3) . . . . ?
Cu1 N1 C9 C10 -176.86(13) . . . . ?
C7 C8 C9 N1 -3.3(3) . . . . ?
C7 C8 C9 C10 178.34(18) . . . . ?
C9 N1 C11 C12 -109.8(2) . . . . ?
Cu1 N1 C11 C12 66.8(2) . . . . ?
C18 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C14 C13 C18 C17 -0.9(3) . . . . ?
C14 C13 C18 C19 178.55(18) . . . . ?
C16 C17 C18 C13 1.0(3) . . . . ?
C16 C17 C18 C19 -178.46(17) . . . . ?
Cu1 O2 C19 C20 -0.4(3) . . . . ?
Cu1 O2 C19 C18 -179.99(11) . . . . ?
C13 C18 C19 O2 9.5(2) . . . . ?
C17 C18 C19 O2 -171.07(18) . . . . ?
C13 C18 C19 C20 -170.12(19) . . . . ?
C17 C18 C19 C20 9.3(3) . . . . ?
O2 C19 C20 C21 -4.2(3) . . . . ?
C18 C19 C20 C21 175.34(18) . . . . ?
C23 N2 C21 C20 -175.57(18) . . . . ?
Cu1 N2 C21 C20 12.1(3) . . . . ?
C23 N2 C21 C22 3.9(3) . . . . ?
Cu1 N2 C21 C22 -168.46(14) . . . . ?
C19 C20 C21 N2 -2.4(3) . . . . ?
C19 C20 C21 C22 178.14(19) . . . . ?
C21 N2 C23 C24 -108.2(2) . . . . ?
Cu1 N2 C23 C24 64.8(2) . . . . ?

_refine_diff_density_max         0.931
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_xbp15
_database_code_depnum_ccdc_archive 'CCDC 1531597'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Ni(B-Et)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 Ni O2'
_chemical_formula_sum            'C24 H28 N2 Ni O2'
_chemical_formula_weight         435.19

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.509(5)
_cell_length_b                   9.826(5)
_cell_length_c                   12.281(6)
_cell_angle_alpha                87.621(8)
_cell_angle_beta                 70.731(7)
_cell_angle_gamma                74.265(8)
_cell_volume                     1041.2(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    1644
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.39

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.954
_shelx_estimated_absorpt_T_min   0.696
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            28983
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.759
_diffrn_reflns_theta_max         31.567
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6833
_reflns_number_gt                5893
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.5813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6833
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.49443(2) 0.24886(2) 0.50096(2) 0.01434(6) Uani 1 1 d . . . . .
N1 N 0.35025(14) 0.43229(13) 0.49900(11) 0.0190(2) Uani 1 1 d . . . . .
N2 N 0.64611(13) 0.07054(12) 0.50340(10) 0.01462(19) Uani 1 1 d . . . . .
O1 O 0.41886(13) 0.24701(11) 0.65944(9) 0.01973(19) Uani 1 1 d . . . . .
O2 O 0.56415(11) 0.24519(11) 0.34200(9) 0.01641(18) Uani 1 1 d . . . . .
C1 C 0.31943(16) 0.16536(14) 0.88789(12) 0.0184(2) Uani 1 1 d . . . . .
H1 H 0.3647 0.0915 0.8291 0.022 Uiso 1 1 calc R U . . .
C2 C 0.29058(17) 0.13210(15) 1.00332(13) 0.0200(2) Uani 1 1 d . . . . .
H2 H 0.3162 0.0360 1.0227 0.024 Uiso 1 1 calc R U . . .
C3 C 0.22435(17) 0.23954(16) 1.09018(12) 0.0202(3) Uani 1 1 d . . . . .
H3 H 0.2041 0.2171 1.1689 0.024 Uiso 1 1 calc R U . . .
C4 C 0.18788(17) 0.38039(16) 1.06080(12) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.1429 0.4540 1.1198 0.025 Uiso 1 1 calc R U . . .
C5 C 0.21691(16) 0.41382(15) 0.94580(12) 0.0185(2) Uani 1 1 d . . . . .
H5 H 0.1922 0.5101 0.9268 0.022 Uiso 1 1 calc R U . . .
C6 C 0.28240(15) 0.30652(14) 0.85764(12) 0.0155(2) Uani 1 1 d . . . . .
C7 C 0.31073(15) 0.34047(14) 0.73369(12) 0.0151(2) Uani 1 1 d . . . . .
C8 C 0.22341(16) 0.46349(15) 0.70505(13) 0.0190(2) Uani 1 1 d . . . . .
H8 H 0.1445 0.5242 0.7660 0.023 Uiso 1 1 calc R U . . .
C9 C 0.24358(15) 0.50544(14) 0.59047(12) 0.0170(2) Uani 1 1 d . . . . .
C10 C 0.13445(17) 0.64699(15) 0.58106(14) 0.0221(3) Uani 1 1 d . . . . .
H10A H 0.0548 0.6781 0.6565 0.033 Uiso 1 1 calc R U . . .
H10B H 0.0851 0.6368 0.5244 0.033 Uiso 1 1 calc R U . . .
H10C H 0.1930 0.7173 0.5562 0.033 Uiso 1 1 calc R U . . .
C11 C 0.35809(19) 0.49804(16) 0.38681(14) 0.0222(3) Uani 1 1 d . . . . .
H11A H 0.4661 0.4694 0.3331 0.027 Uiso 1 1 calc R U . . .
H11B H 0.3259 0.6024 0.3988 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2530(2) 0.45224(19) 0.33433(16) 0.0302(3) Uani 1 1 d . . . . .
H12A H 0.2691 0.4865 0.2563 0.045 Uiso 1 1 calc R U . . .
H12B H 0.1447 0.4920 0.3823 0.045 Uiso 1 1 calc R U . . .
H12C H 0.2774 0.3487 0.3306 0.045 Uiso 1 1 calc R U . . .
C13 C 0.59717(16) 0.25707(16) 0.10517(12) 0.0198(2) Uani 1 1 d . . . . .
H13 H 0.4941 0.2755 0.1573 0.024 Uiso 1 1 calc R U . . .
C14 C 0.62292(18) 0.28496(17) -0.01083(13) 0.0228(3) Uani 1 1 d . . . . .
H14 H 0.5376 0.3204 -0.0377 0.027 Uiso 1 1 calc R U . . .
C15 C 0.77368(18) 0.26089(16) -0.08756(13) 0.0214(3) Uani 1 1 d . . . . .
H15 H 0.7915 0.2798 -0.1668 0.026 Uiso 1 1 calc R U . . .
C16 C 0.89829(17) 0.20895(15) -0.04742(13) 0.0210(3) Uani 1 1 d . . . . .
H16 H 1.0012 0.1943 -0.0991 0.025 Uiso 1 1 calc R U . . .
C17 C 0.87252(16) 0.17855(15) 0.06802(12) 0.0184(2) Uani 1 1 d . . . . .
H17 H 0.9581 0.1414 0.0943 0.022 Uiso 1 1 calc R U . . .
C18 C 0.72149(15) 0.20219(14) 0.14593(12) 0.0153(2) Uani 1 1 d . . . . .
C19 C 0.69135(15) 0.16787(14) 0.26976(12) 0.0150(2) Uani 1 1 d . . . . .
C20 C 0.79286(16) 0.05614(15) 0.29973(12) 0.0183(2) Uani 1 1 d . . . . .
H20 H 0.8871 0.0102 0.2416 0.022 Uiso 1 1 calc R U . . .
C21 C 0.76396(15) 0.00609(14) 0.41299(12) 0.0166(2) Uani 1 1 d . . . . .
C22 C 0.87830(17) -0.13266(16) 0.42199(14) 0.0226(3) Uani 1 1 d . . . . .
H22A H 0.9677 -0.1535 0.3507 0.034 Uiso 1 1 calc R U . . .
H22B H 0.8278 -0.2093 0.4335 0.034 Uiso 1 1 calc R U . . .
H22C H 0.9130 -0.1246 0.4876 0.034 Uiso 1 1 calc R U . . .
C23 C 0.62988(16) -0.00010(14) 0.61377(12) 0.0171(2) Uani 1 1 d . . . . .
H23A H 0.6759 -0.1034 0.5975 0.020 Uiso 1 1 calc R U . . .
H23B H 0.5185 0.0162 0.6584 0.020 Uiso 1 1 calc R U . . .
C24 C 0.70853(19) 0.05396(18) 0.68639(14) 0.0245(3) Uani 1 1 d . . . . .
H24A H 0.6871 0.0107 0.7613 0.037 Uiso 1 1 calc R U . . .
H24B H 0.6684 0.1571 0.6983 0.037 Uiso 1 1 calc R U . . .
H24C H 0.8206 0.0287 0.6461 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8401(14) . ?
Ni1 O2 1.8414(14) . ?
Ni1 N2 1.9506(13) . ?
Ni1 N1 1.9510(14) . ?
N1 C9 1.3142(19) . ?
N1 C11 1.485(2) . ?
N2 C21 1.3198(18) . ?
N2 C23 1.4782(18) . ?
O1 C7 1.2926(16) . ?
O2 C19 1.2949(16) . ?
C1 C2 1.395(2) . ?
C1 C6 1.402(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4019(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.496(2) . ?
C7 C8 1.3737(19) . ?
C8 C9 1.415(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.519(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.520(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.392(2) . ?
C13 C18 1.4005(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.4009(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.494(2) . ?
C19 C20 1.3779(19) . ?
C20 C21 1.420(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.522(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.527(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 Ni1 O2 177.22(5) . . ?
O1 Ni1 N2 87.35(5) . . ?
O2 Ni1 N2 92.38(5) . . ?
O1 Ni1 N1 92.69(5) . . ?
O2 Ni1 N1 87.72(5) . . ?
N2 Ni1 N1 177.08(5) . . ?
C9 N1 C11 115.64(12) . . ?
C9 N1 Ni1 125.23(10) . . ?
C11 N1 Ni1 119.13(10) . . ?
C21 N2 C23 116.44(12) . . ?
C21 N2 Ni1 124.96(10) . . ?
C23 N2 Ni1 118.60(9) . . ?
C7 O1 Ni1 129.72(10) . . ?
C19 O2 Ni1 129.06(9) . . ?
C2 C1 C6 120.76(13) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.10(14) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.52(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.49(13) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.51(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.61(13) . . ?
C1 C6 C7 120.18(12) . . ?
C5 C6 C7 121.20(12) . . ?
O1 C7 C8 124.32(13) . . ?
O1 C7 C6 115.51(12) . . ?
C8 C7 C6 120.17(12) . . ?
C7 C8 C9 124.12(13) . . ?
C7 C8 H8 117.9 . . ?
C9 C8 H8 117.9 . . ?
N1 C9 C8 123.84(13) . . ?
N1 C9 C10 121.83(13) . . ?
C8 C9 C10 114.30(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 110.36(13) . . ?
N1 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 120.76(13) . . ?
C14 C13 H13 119.6 . . ?
C18 C13 H13 119.6 . . ?
C13 C14 C15 120.09(14) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 119.61(14) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.26(13) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.62(13) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 118.63(13) . . ?
C13 C18 C19 119.91(12) . . ?
C17 C18 C19 121.45(12) . . ?
O2 C19 C20 124.45(13) . . ?
O2 C19 C18 115.60(12) . . ?
C20 C19 C18 119.89(12) . . ?
C19 C20 C21 123.45(13) . . ?
C19 C20 H20 118.3 . . ?
C21 C20 H20 118.3 . . ?
N2 C21 C20 123.78(13) . . ?
N2 C21 C22 121.87(13) . . ?
C20 C21 C22 114.33(12) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 C24 112.26(12) . . ?
N2 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
N2 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ni1 O1 C7 176.15(13) . . . . ?
N1 Ni1 O1 C7 -0.93(13) . . . . ?
N2 Ni1 O2 C19 -14.57(12) . . . . ?
N1 Ni1 O2 C19 162.51(12) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C2 C1 C6 C7 -178.64(13) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C5 C6 C7 178.46(12) . . . . ?
Ni1 O1 C7 C8 2.7(2) . . . . ?
Ni1 O1 C7 C6 -177.93(9) . . . . ?
C1 C6 C7 O1 -25.73(18) . . . . ?
C5 C6 C7 O1 155.11(13) . . . . ?
C1 C6 C7 C8 153.62(14) . . . . ?
C5 C6 C7 C8 -25.54(19) . . . . ?
O1 C7 C8 C9 -1.8(2) . . . . ?
C6 C7 C8 C9 178.94(13) . . . . ?
C11 N1 C9 C8 -176.81(13) . . . . ?
Ni1 N1 C9 C8 3.1(2) . . . . ?
C11 N1 C9 C10 0.8(2) . . . . ?
Ni1 N1 C9 C10 -179.22(10) . . . . ?
C7 C8 C9 N1 -1.3(2) . . . . ?
C7 C8 C9 C10 -179.12(13) . . . . ?
C9 N1 C11 C12 -89.97(17) . . . . ?
Ni1 N1 C11 C12 90.07(14) . . . . ?
C18 C13 C14 C15 -1.2(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 1.3(2) . . . . ?
C15 C16 C17 C18 -1.3(2) . . . . ?
C14 C13 C18 C17 1.3(2) . . . . ?
C14 C13 C18 C19 -177.69(13) . . . . ?
C16 C17 C18 C13 0.0(2) . . . . ?
C16 C17 C18 C19 178.91(12) . . . . ?
Ni1 O2 C19 C20 9.4(2) . . . . ?
Ni1 O2 C19 C18 -173.44(9) . . . . ?
C13 C18 C19 O2 -30.31(18) . . . . ?
C17 C18 C19 O2 150.76(13) . . . . ?
C13 C18 C19 C20 147.03(14) . . . . ?
C17 C18 C19 C20 -31.89(19) . . . . ?
O2 C19 C20 C21 4.7(2) . . . . ?
C18 C19 C20 C21 -172.40(12) . . . . ?
C23 N2 C21 C20 177.29(12) . . . . ?
Ni1 N2 C21 C20 -2.43(19) . . . . ?
C23 N2 C21 C22 -0.71(18) . . . . ?
Ni1 N2 C21 C22 179.56(10) . . . . ?
C19 C20 C21 N2 -7.8(2) . . . . ?
C19 C20 C21 C22 170.34(13) . . . . ?
C21 N2 C23 C24 93.70(15) . . . . ?
Ni1 N2 C23 C24 -86.56(13) . . . . ?

_refine_diff_density_max         1.405
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.151

####################################################################### 
# 
# 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_xbp49
_database_code_depnum_ccdc_archive 'CCDC 1531604'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'beta Zn(B-Bn)2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 N2 O2 Zn'
_chemical_formula_sum            'C34 H32 N2 O2 Zn'
_chemical_formula_weight         565.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.8756(12)
_cell_length_b                   14.6124(13)
_cell_length_c                   14.7723(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.4210(10)
_cell_angle_gamma                90
_cell_volume                     2768.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      31.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.921
_shelx_estimated_absorpt_T_min   0.874
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7194
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            44087
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.714
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8437
_reflns_number_gt                7188
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+1.6032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8437
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.38879(2) 0.35097(2) 0.64920(2) 0.01872(6) Uani 1 1 d . . . . .
N1 N 0.33298(10) 0.33898(8) 0.50420(9) 0.0193(2) Uani 1 1 d . . . . .
N2 N 0.31437(10) 0.37543(9) 0.73850(9) 0.0198(2) Uani 1 1 d . . . . .
O1 O 0.43842(9) 0.22449(7) 0.67873(8) 0.0233(2) Uani 1 1 d . . . . .
O2 O 0.50217(8) 0.43724(7) 0.70812(8) 0.0192(2) Uani 1 1 d . . . . .
C1 C 0.50902(12) 0.05610(10) 0.75116(11) 0.0199(3) Uani 1 1 d . . . . .
H1 H 0.5178 0.1067 0.7939 0.024 Uiso 1 1 calc R U . . .
C2 C 0.54895(13) -0.02907(11) 0.78977(12) 0.0236(3) Uani 1 1 d . . . . .
H2 H 0.5848 -0.0360 0.8585 0.028 Uiso 1 1 calc R U . . .
C3 C 0.53663(13) -0.10400(11) 0.72849(12) 0.0249(3) Uani 1 1 d . . . . .
H3 H 0.5641 -0.1620 0.7549 0.030 Uiso 1 1 calc R U . . .
C4 C 0.48369(13) -0.09318(10) 0.62813(12) 0.0229(3) Uani 1 1 d . . . . .
H4 H 0.4748 -0.1441 0.5858 0.028 Uiso 1 1 calc R U . . .
C5 C 0.44371(12) -0.00829(10) 0.58932(11) 0.0188(3) Uani 1 1 d . . . . .
H5 H 0.4075 -0.0019 0.5206 0.023 Uiso 1 1 calc R U . . .
C6 C 0.45613(11) 0.06805(9) 0.65023(10) 0.0157(2) Uani 1 1 d . . . . .
C7 C 0.41835(11) 0.16187(9) 0.61234(11) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.36577(13) 0.17551(10) 0.51319(11) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.3545 0.1223 0.4736 0.025 Uiso 1 1 calc R U . . .
C9 C 0.32601(12) 0.25864(10) 0.46208(11) 0.0204(3) Uani 1 1 d . . . . .
C10 C 0.27426(16) 0.25021(12) 0.35190(11) 0.0318(4) Uani 1 1 d . . . . .
H10A H 0.3124 0.2873 0.3213 0.048 Uiso 1 1 calc R U . . .
H10B H 0.2021 0.2719 0.3301 0.048 Uiso 1 1 calc R U . . .
H10C H 0.2748 0.1860 0.3329 0.048 Uiso 1 1 calc R U . . .
C11 C 0.29054(17) 0.41859(11) 0.43925(12) 0.0334(4) Uani 1 1 d . . . . .
H11A H 0.2138 0.4127 0.4074 0.040 Uiso 1 1 calc R U . . .
H11B H 0.3191 0.4190 0.3873 0.040 Uiso 1 1 calc R U . . .
C12 C 0.31713(13) 0.50756(10) 0.49477(11) 0.0229(3) Uani 1 1 d . . . . .
C13 C 0.26879(13) 0.53120(11) 0.55838(12) 0.0234(3) Uani 1 1 d . . . . .
H13 H 0.2161 0.4927 0.5637 0.028 Uiso 1 1 calc R U . . .
C14 C 0.29673(13) 0.61034(11) 0.61406(12) 0.0257(3) Uani 1 1 d . . . . .
H14 H 0.2638 0.6254 0.6579 0.031 Uiso 1 1 calc R U . . .
C15 C 0.37272(14) 0.66756(11) 0.60580(13) 0.0275(3) Uani 1 1 d . . . . .
H15 H 0.3927 0.7214 0.6446 0.033 Uiso 1 1 calc R U . . .
C16 C 0.41929(13) 0.64578(11) 0.54070(14) 0.0283(3) Uani 1 1 d . . . . .
H16 H 0.4705 0.6854 0.5340 0.034 Uiso 1 1 calc R U . . .
C17 C 0.39147(13) 0.56619(11) 0.48499(12) 0.0264(3) Uani 1 1 d . . . . .
H17 H 0.4234 0.5519 0.4401 0.032 Uiso 1 1 calc R U . . .
C18 C 0.68972(12) 0.52527(11) 0.80376(11) 0.0221(3) Uani 1 1 d . . . . .
H18 H 0.6908 0.4688 0.7722 0.027 Uiso 1 1 calc R U . . .
C19 C 0.77873(12) 0.57913(13) 0.83864(12) 0.0283(3) Uani 1 1 d . . . . .
H19 H 0.8408 0.5588 0.8322 0.034 Uiso 1 1 calc R U . . .
C20 C 0.77731(14) 0.66250(13) 0.88286(12) 0.0308(4) Uani 1 1 d . . . . .
H20 H 0.8384 0.6993 0.9065 0.037 Uiso 1 1 calc R U . . .
C21 C 0.68688(14) 0.69229(12) 0.89258(12) 0.0280(3) Uani 1 1 d . . . . .
H21 H 0.6859 0.7497 0.9224 0.034 Uiso 1 1 calc R U . . .
C22 C 0.59746(13) 0.63832(10) 0.85875(11) 0.0222(3) Uani 1 1 d . . . . .
H22 H 0.5356 0.6590 0.8655 0.027 Uiso 1 1 calc R U . . .
C23 C 0.59851(11) 0.55347(10) 0.81467(10) 0.0177(3) Uani 1 1 d . . . . .
C24 C 0.50604(11) 0.49085(9) 0.77893(10) 0.0161(2) Uani 1 1 d . . . . .
C25 C 0.43742(11) 0.49195(10) 0.82685(10) 0.0182(3) Uani 1 1 d . . . . .
H25 H 0.4506 0.5368 0.8767 0.022 Uiso 1 1 calc R U . . .
C26 C 0.34961(11) 0.43436(10) 0.81070(10) 0.0181(3) Uani 1 1 d . . . . .
C27 C 0.29870(14) 0.44427(13) 0.88458(13) 0.0293(3) Uani 1 1 d . . . . .
H27A H 0.2983 0.3848 0.9151 0.044 Uiso 1 1 calc R U . . .
H27B H 0.2269 0.4659 0.8513 0.044 Uiso 1 1 calc R U . . .
H27C H 0.3380 0.4885 0.9350 0.044 Uiso 1 1 calc R U . . .
C28 C 0.22778(16) 0.31388(15) 0.73440(13) 0.0368(4) Uani 1 1 d . . . . .
H28A H 0.1874 0.3430 0.7693 0.044 Uiso 1 1 calc R U . . .
H28B H 0.2571 0.2559 0.7685 0.044 Uiso 1 1 calc R U . . .
C29 C 0.15554(12) 0.29300(11) 0.63044(11) 0.0228(3) Uani 1 1 d . . . . .
C30 C 0.16120(14) 0.21136(12) 0.58566(14) 0.0291(3) Uani 1 1 d . . . . .
H30 H 0.2116 0.1669 0.6207 0.035 Uiso 1 1 calc R U . . .
C31 C 0.09411(17) 0.19335(14) 0.49003(15) 0.0400(5) Uani 1 1 d . . . . .
H31 H 0.0993 0.1371 0.4600 0.048 Uiso 1 1 calc R U . . .
C32 C 0.02086(17) 0.25626(17) 0.43913(14) 0.0462(6) Uani 1 1 d . . . . .
H32 H -0.0248 0.2438 0.3736 0.055 Uiso 1 1 calc R U . . .
C33 C 0.01287(16) 0.33832(16) 0.48278(16) 0.0422(5) Uani 1 1 d . . . . .
H33 H -0.0386 0.3819 0.4475 0.051 Uiso 1 1 calc R U . . .
C34 C 0.08057(14) 0.35686(12) 0.57877(14) 0.0306(4) Uani 1 1 d . . . . .
H34 H 0.0754 0.4132 0.6087 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 1.9435(11) . ?
Zn1 O1 1.9625(11) . ?
Zn1 N1 1.9883(13) . ?
Zn1 N2 1.9934(13) . ?
N1 C9 1.3148(19) . ?
N1 C11 1.4797(19) . ?
N2 C26 1.3116(19) . ?
N2 C28 1.483(2) . ?
O1 C7 1.2916(17) . ?
O2 C24 1.2914(17) . ?
C1 C2 1.393(2) . ?
C1 C6 1.399(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4019(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4980(19) . ?
C7 C8 1.379(2) . ?
C8 C9 1.425(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.513(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.506(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.390(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 C23 1.398(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.403(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.499(2) . ?
C24 C25 1.386(2) . ?
C25 C26 1.424(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.516(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.511(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.381(2) . ?
C29 C34 1.389(2) . ?
C30 C31 1.389(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.364(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.397(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O1 110.85(5) . . ?
O2 Zn1 N1 117.11(5) . . ?
O1 Zn1 N1 96.66(5) . . ?
O2 Zn1 N2 97.04(5) . . ?
O1 Zn1 N2 104.37(5) . . ?
N1 Zn1 N2 129.91(5) . . ?
C9 N1 C11 117.13(13) . . ?
C9 N1 Zn1 121.10(10) . . ?
C11 N1 Zn1 121.63(10) . . ?
C26 N2 C28 118.44(14) . . ?
C26 N2 Zn1 121.96(10) . . ?
C28 N2 Zn1 118.70(11) . . ?
C7 O1 Zn1 122.86(9) . . ?
C24 O2 Zn1 122.18(9) . . ?
C2 C1 C6 120.85(14) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.43(14) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.28(14) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.46(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.88(14) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.09(13) . . ?
C1 C6 C7 118.61(12) . . ?
C5 C6 C7 123.27(13) . . ?
O1 C7 C8 125.29(13) . . ?
O1 C7 C6 114.91(12) . . ?
C8 C7 C6 119.80(12) . . ?
C7 C8 C9 128.80(14) . . ?
C7 C8 H8 115.6 . . ?
C9 C8 H8 115.6 . . ?
N1 C9 C8 124.51(13) . . ?
N1 C9 C10 120.05(13) . . ?
C8 C9 C10 115.44(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 111.80(13) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C17 C12 C13 119.05(15) . . ?
C17 C12 C11 120.84(16) . . ?
C13 C12 C11 120.09(16) . . ?
C14 C13 C12 120.70(15) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.05(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.62(16) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.34(16) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 120.20(15) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C23 120.46(16) . . ?
C19 C18 H18 119.8 . . ?
C23 C18 H18 119.8 . . ?
C20 C19 C18 120.20(16) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.06(15) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.19(16) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 120.11(16) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 118.96(14) . . ?
C18 C23 C24 118.08(13) . . ?
C22 C23 C24 122.96(13) . . ?
O2 C24 C25 126.60(13) . . ?
O2 C24 C23 114.91(12) . . ?
C25 C24 C23 118.39(12) . . ?
C24 C25 C26 128.16(13) . . ?
C24 C25 H25 115.9 . . ?
C26 C25 H25 115.9 . . ?
N2 C26 C25 123.64(13) . . ?
N2 C26 C27 121.09(14) . . ?
C25 C26 C27 115.26(13) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N2 C28 C29 112.15(13) . . ?
N2 C28 H28A 109.2 . . ?
C29 C28 H28A 109.2 . . ?
N2 C28 H28B 109.2 . . ?
C29 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C30 C29 C34 118.99(16) . . ?
C30 C29 C28 121.64(17) . . ?
C34 C29 C28 119.37(17) . . ?
C29 C30 C31 120.83(18) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C32 C31 C30 120.17(19) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 120.11(18) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C34 119.88(19) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C29 C34 C33 120.02(18) . . ?
C29 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?

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
C6 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C1 C6 C7 -177.71(14) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 177.62(14) . . . . ?
Zn1 O1 C7 C8 3.8(2) . . . . ?
Zn1 O1 C7 C6 -175.60(9) . . . . ?
C1 C6 C7 O1 -0.38(19) . . . . ?
C5 C6 C7 O1 -178.57(13) . . . . ?
C1 C6 C7 C8 -179.84(14) . . . . ?
C5 C6 C7 C8 2.0(2) . . . . ?
O1 C7 C8 C9 2.4(3) . . . . ?
C6 C7 C8 C9 -178.22(15) . . . . ?
C11 N1 C9 C8 177.88(16) . . . . ?
Zn1 N1 C9 C8 -6.5(2) . . . . ?
C11 N1 C9 C10 -1.3(2) . . . . ?
Zn1 N1 C9 C10 174.41(12) . . . . ?
C7 C8 C9 N1 -0.8(3) . . . . ?
C7 C8 C9 C10 178.42(16) . . . . ?
C9 N1 C11 C12 -171.68(15) . . . . ?
Zn1 N1 C11 C12 12.7(2) . . . . ?
N1 C11 C12 C17 107.07(18) . . . . ?
N1 C11 C12 C13 -71.6(2) . . . . ?
C17 C12 C13 C14 -2.3(2) . . . . ?
C11 C12 C13 C14 176.35(15) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C13 C12 C17 C16 2.1(2) . . . . ?
C11 C12 C17 C16 -176.53(15) . . . . ?
C15 C16 C17 C12 -0.4(2) . . . . ?
C23 C18 C19 C20 -1.4(2) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C20 C21 C22 C23 0.0(2) . . . . ?
C19 C18 C23 C22 1.9(2) . . . . ?
C19 C18 C23 C24 -177.75(13) . . . . ?
C21 C22 C23 C18 -1.2(2) . . . . ?
C21 C22 C23 C24 178.41(14) . . . . ?
Zn1 O2 C24 C25 4.3(2) . . . . ?
Zn1 O2 C24 C23 -179.43(9) . . . . ?
C18 C23 C24 O2 -27.34(18) . . . . ?
C22 C23 C24 O2 153.01(14) . . . . ?
C18 C23 C24 C25 149.25(14) . . . . ?
C22 C23 C24 C25 -30.4(2) . . . . ?
O2 C24 C25 C26 1.2(3) . . . . ?
C23 C24 C25 C26 -174.93(14) . . . . ?
C28 N2 C26 C25 174.94(15) . . . . ?
Zn1 N2 C26 C25 6.0(2) . . . . ?
C28 N2 C26 C27 -4.1(2) . . . . ?
Zn1 N2 C26 C27 -173.08(11) . . . . ?
C24 C25 C26 N2 -7.1(2) . . . . ?
C24 C25 C26 C27 172.01(15) . . . . ?
C26 N2 C28 C29 146.19(16) . . . . ?
Zn1 N2 C28 C29 -44.5(2) . . . . ?
N2 C28 C29 C30 101.1(2) . . . . ?
N2 C28 C29 C34 -79.7(2) . . . . ?
C34 C29 C30 C31 0.8(2) . . . . ?
C28 C29 C30 C31 179.98(16) . . . . ?
C29 C30 C31 C32 -0.5(3) . . . . ?
C30 C31 C32 C33 -0.2(3) . . . . ?
C31 C32 C33 C34 0.5(3) . . . . ?
C30 C29 C34 C33 -0.5(2) . . . . ?
C28 C29 C34 C33 -179.66(16) . . . . ?
C32 C33 C34 C29 -0.2(3) . . . . ?

_refine_diff_density_max         1.047
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_xbp21
_database_code_depnum_ccdc_archive 'CCDC 1531600'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Ni(B-Bn)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 N2 Ni O2'
_chemical_formula_sum            'C34 H32 N2 Ni O2'
_chemical_formula_weight         559.32

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.5225(3)
_cell_length_b                   25.9549(12)
_cell_length_c                   6.9974(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.5330(10)
_cell_angle_gamma                90
_cell_volume                     1351.09(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      31.59

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.753
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3

_diffrn_reflns_number            22633
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.569
_diffrn_reflns_theta_max         31.605
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4497
_reflns_number_gt                4141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.9020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4497
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.0000 0.01127(7) Uani 1 2 d S . P . .
N1 N 0.62797(13) 0.52746(4) 0.23940(15) 0.01216(18) Uani 1 1 d . . . . .
O1 O 0.47825(12) 0.43629(3) 0.10864(13) 0.01379(16) Uani 1 1 d . . . . .
C1 C 0.35554(18) 0.34275(5) 0.25341(18) 0.0170(2) Uani 1 1 d . . . . .
H1 H 0.2633 0.3641 0.1886 0.020 Uiso 1 1 calc R U . . .
C2 C 0.3172(2) 0.29191(5) 0.2975(2) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.1985 0.2790 0.2647 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4525(2) 0.26003(5) 0.3894(2) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.4263 0.2254 0.4188 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6258(2) 0.27905(5) 0.4378(2) 0.0245(3) Uani 1 1 d . . . . .
H4 H 0.7184 0.2572 0.4995 0.029 Uiso 1 1 calc R U . . .
C5 C 0.66485(19) 0.32997(5) 0.3965(2) 0.0194(2) Uani 1 1 d . . . . .
H5 H 0.7835 0.3428 0.4308 0.023 Uiso 1 1 calc R U . . .
C6 C 0.52886(17) 0.36229(5) 0.30415(17) 0.0141(2) Uani 1 1 d . . . . .
C7 C 0.56642(15) 0.41759(4) 0.26689(17) 0.0122(2) Uani 1 1 d . . . . .
C8 C 0.67946(16) 0.44535(5) 0.40058(17) 0.0137(2) Uani 1 1 d . . . . .
H8 H 0.7465 0.4275 0.5059 0.016 Uiso 1 1 calc R U . . .
C9 C 0.70116(16) 0.49970(4) 0.38900(18) 0.0126(2) Uani 1 1 d . . . . .
C10 C 0.80892(16) 0.52433(5) 0.56593(18) 0.0154(2) Uani 1 1 d . . . . .
H10A H 0.8866 0.5513 0.5253 0.023 Uiso 1 1 calc R U . . .
H10B H 0.8831 0.4981 0.6403 0.023 Uiso 1 1 calc R U . . .
H10C H 0.7267 0.5396 0.6465 0.023 Uiso 1 1 calc R U . . .
C11 C 0.65206(15) 0.58369(4) 0.25847(17) 0.0124(2) Uani 1 1 d . . . . .
H11A H 0.6502 0.5935 0.3949 0.015 Uiso 1 1 calc R U . . .
H11B H 0.5494 0.6010 0.1789 0.015 Uiso 1 1 calc R U . . .
C12 C 0.82553(15) 0.60310(4) 0.19725(17) 0.0122(2) Uani 1 1 d . . . . .
C13 C 0.87854(17) 0.65400(5) 0.23964(19) 0.0166(2) Uani 1 1 d . . . . .
H13 H 0.8101 0.6750 0.3128 0.020 Uiso 1 1 calc R U . . .
C14 C 1.03059(19) 0.67409(5) 0.1755(2) 0.0213(3) Uani 1 1 d . . . . .
H14 H 1.0640 0.7089 0.2033 0.026 Uiso 1 1 calc R U . . .
C15 C 1.13416(18) 0.64365(6) 0.0710(2) 0.0219(3) Uani 1 1 d . . . . .
H15 H 1.2381 0.6575 0.0278 0.026 Uiso 1 1 calc R U . . .
C16 C 1.08403(17) 0.59259(5) 0.0302(2) 0.0195(2) Uani 1 1 d . . . . .
H16 H 1.1546 0.5714 -0.0400 0.023 Uiso 1 1 calc R U . . .
C17 C 0.92995(16) 0.57267(5) 0.09279(18) 0.0149(2) Uani 1 1 d . . . . .
H17 H 0.8959 0.5380 0.0638 0.018 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8373(9) 3_665 ?
Ni1 O1 1.8373(9) . ?
Ni1 N1 1.9396(11) . ?
Ni1 N1 1.9396(10) 3_665 ?
N1 C9 1.3217(16) . ?
N1 C11 1.4744(15) . ?
O1 C7 1.2976(14) . ?
C1 C2 1.3949(18) . ?
C1 C6 1.3949(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3936(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4041(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4933(16) . ?
C7 C8 1.3715(17) . ?
C8 C9 1.4239(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.5168(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5185(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.3948(16) . ?
C12 C13 1.3990(16) . ?
C13 C14 1.3906(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3975(17) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 180.00(6) 3_665 . ?
O1 Ni1 N1 87.91(4) 3_665 . ?
O1 Ni1 N1 92.09(4) . . ?
O1 Ni1 N1 92.10(4) 3_665 3_665 ?
O1 Ni1 N1 87.90(4) . 3_665 ?
N1 Ni1 N1 180.0 . 3_665 ?
C9 N1 C11 115.89(10) . . ?
C9 N1 Ni1 125.37(8) . . ?
C11 N1 Ni1 118.72(8) . . ?
C7 O1 Ni1 128.62(8) . . ?
C2 C1 C6 120.24(13) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.22(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.79(13) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.38(13) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.04(13) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.31(12) . . ?
C1 C6 C7 119.93(11) . . ?
C5 C6 C7 120.72(11) . . ?
O1 C7 C8 124.91(11) . . ?
O1 C7 C6 115.00(10) . . ?
C8 C7 C6 120.00(11) . . ?
C7 C8 C9 123.11(11) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
N1 C9 C8 123.18(11) . . ?
N1 C9 C10 121.75(10) . . ?
C8 C9 C10 115.02(11) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 113.71(9) . . ?
N1 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C17 C12 C13 118.74(11) . . ?
C17 C12 C11 122.30(10) . . ?
C13 C12 C11 118.90(10) . . ?
C14 C13 C12 120.52(12) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.55(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 119.43(12) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 119.92(12) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.82(11) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 O1 C7 -16.73(10) . . . . ?
N1 Ni1 O1 C7 163.27(10) 3_665 . . . ?
C6 C1 C2 C3 -1.1(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C2 C1 C6 C5 1.23(18) . . . . ?
C2 C1 C6 C7 -176.44(11) . . . . ?
C4 C5 C6 C1 -0.45(19) . . . . ?
C4 C5 C6 C7 177.20(12) . . . . ?
Ni1 O1 C7 C8 9.53(17) . . . . ?
Ni1 O1 C7 C6 -174.05(8) . . . . ?
C1 C6 C7 O1 -36.41(15) . . . . ?
C5 C6 C7 O1 145.95(12) . . . . ?
C1 C6 C7 C8 140.20(12) . . . . ?
C5 C6 C7 C8 -37.44(17) . . . . ?
O1 C7 C8 C9 5.76(19) . . . . ?
C6 C7 C8 C9 -170.49(11) . . . . ?
C11 N1 C9 C8 175.20(10) . . . . ?
Ni1 N1 C9 C8 -6.53(17) . . . . ?
C11 N1 C9 C10 -2.15(16) . . . . ?
Ni1 N1 C9 C10 176.13(8) . . . . ?
C7 C8 C9 N1 -6.73(19) . . . . ?
C7 C8 C9 C10 170.78(11) . . . . ?
C9 N1 C11 C12 86.81(13) . . . . ?
Ni1 N1 C11 C12 -91.59(10) . . . . ?
N1 C11 C12 C17 13.79(16) . . . . ?
N1 C11 C12 C13 -169.07(11) . . . . ?
C17 C12 C13 C14 1.21(19) . . . . ?
C11 C12 C13 C14 -176.02(12) . . . . ?
C12 C13 C14 C15 -1.1(2) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C13 C12 C17 C16 -0.43(18) . . . . ?
C11 C12 C17 C16 176.71(11) . . . . ?
C15 C16 C17 C12 -0.5(2) . . . . ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_xbp19
_database_code_depnum_ccdc_archive 'CCDC 1531599'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Co(B-Et)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 Co N2 O2'
_chemical_formula_sum            'C24 H28 Co N2 O2'
_chemical_formula_weight         435.41

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.6021(17)
_cell_length_b                   13.2685(18)
_cell_length_c                   14.856(2)
_cell_angle_alpha                102.934(2)
_cell_angle_beta                 94.203(2)
_cell_angle_gamma                117.9330(18)
_cell_volume                     2092.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    6139
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      29.98

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.842
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            35987
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.437
_diffrn_reflns_theta_max         31.689
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13854
_reflns_number_gt                9361
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.4340P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13854
_refine_ls_number_parameters     531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.84812(2) 0.71247(2) 0.19043(2) 0.01346(7) Uani 1 1 d . . . . .
Co2 Co 0.18157(2) 0.29685(2) 0.29505(2) 0.01439(7) Uani 1 1 d . . . . .
N1 N 0.94868(15) 0.83674(14) 0.13241(11) 0.0135(3) Uani 1 1 d . . . . .
N2 N 0.76395(14) 0.54250(14) 0.11670(11) 0.0136(3) Uani 1 1 d . . . . .
N3 N 0.09494(15) 0.17149(14) 0.35499(11) 0.0150(3) Uani 1 1 d . . . . .
N4 N 0.26448(15) 0.46342(14) 0.37620(11) 0.0150(3) Uani 1 1 d . . . . .
O1 O 0.97292(12) 0.75737(12) 0.29880(9) 0.0157(3) Uani 1 1 d . . . . .
O2 O 0.70542(12) 0.71868(12) 0.22273(10) 0.0169(3) Uani 1 1 d . . . . .
O3 O 0.04682(12) 0.24246(12) 0.19151(9) 0.0150(3) Uani 1 1 d . . . . .
O4 O 0.32675(12) 0.29364(12) 0.26491(10) 0.0175(3) Uani 1 1 d . . . . .
C1 C 1.13159(18) 0.77489(18) 0.44528(13) 0.0161(4) Uani 1 1 d . . . . .
H1 H 1.0539 0.7044 0.4211 0.019 Uiso 1 1 calc R U . . .
C2 C 1.2053(2) 0.78922(19) 0.52666(14) 0.0195(4) Uani 1 1 d . . . . .
H2 H 1.1783 0.7286 0.5574 0.023 Uiso 1 1 calc R U . . .
C3 C 1.3187(2) 0.8923(2) 0.56309(15) 0.0224(4) Uani 1 1 d . . . . .
H3 H 1.3693 0.9023 0.6188 0.027 Uiso 1 1 calc R U . . .
C4 C 1.35769(19) 0.9803(2) 0.51794(15) 0.0225(5) Uani 1 1 d . . . . .
H4 H 1.4350 1.0511 0.5429 0.027 Uiso 1 1 calc R U . . .
C5 C 1.28441(18) 0.96567(19) 0.43657(14) 0.0183(4) Uani 1 1 d . . . . .
H5 H 1.3122 1.0265 0.4060 0.022 Uiso 1 1 calc R U . . .
C6 C 1.16944(17) 0.86204(17) 0.39846(13) 0.0140(4) Uani 1 1 d . . . . .
C7 C 1.08532(17) 0.84364(17) 0.31214(13) 0.0125(4) Uani 1 1 d . . . . .
C8 C 1.12851(17) 0.91590(17) 0.25444(13) 0.0139(4) Uani 1 1 d . . . . .
H8 H 1.2138 0.9726 0.2716 0.017 Uiso 1 1 calc R U . . .
C9 C 1.06374(17) 0.91792(17) 0.17260(13) 0.0130(4) Uani 1 1 d . . . . .
C10 C 1.13294(18) 1.01954(17) 0.13306(14) 0.0168(4) Uani 1 1 d . . . . .
H10A H 1.0871 1.0616 0.1291 0.025 Uiso 1 1 calc R U . . .
H10B H 1.1430 0.9885 0.0699 0.025 Uiso 1 1 calc R U . . .
H10C H 1.2139 1.0748 0.1744 0.025 Uiso 1 1 calc R U . . .
C11 C 0.89514(18) 0.84845(18) 0.04638(14) 0.0172(4) Uani 1 1 d . . . . .
H11A H 0.9520 0.8602 0.0022 0.021 Uiso 1 1 calc R U . . .
H11B H 0.8856 0.9199 0.0633 0.021 Uiso 1 1 calc R U . . .
C12 C 0.7723(2) 0.7406(2) -0.00202(17) 0.0352(6) Uani 1 1 d . . . . .
H12A H 0.7410 0.7512 -0.0595 0.053 Uiso 1 1 calc R U . . .
H12B H 0.7146 0.7307 0.0405 0.053 Uiso 1 1 calc R U . . .
H12C H 0.7812 0.6696 -0.0186 0.053 Uiso 1 1 calc R U . . .
C13 C 0.52374(19) 0.77961(19) 0.23402(14) 0.0182(4) Uani 1 1 d . . . . .
H13 H 0.6067 0.8412 0.2450 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4332(2) 0.8094(2) 0.24908(15) 0.0217(4) Uani 1 1 d . . . . .
H14 H 0.4544 0.8909 0.2694 0.026 Uiso 1 1 calc R U . . .
C15 C 0.3115(2) 0.7203(2) 0.23456(15) 0.0231(5) Uani 1 1 d . . . . .
H15 H 0.2492 0.7404 0.2442 0.028 Uiso 1 1 calc R U . . .
C16 C 0.28220(19) 0.6019(2) 0.20588(14) 0.0206(4) Uani 1 1 d . . . . .
H16 H 0.1994 0.5406 0.1964 0.025 Uiso 1 1 calc R U . . .
C17 C 0.37234(18) 0.57185(19) 0.19088(14) 0.0177(4) Uani 1 1 d . . . . .
H17 H 0.3508 0.4902 0.1721 0.021 Uiso 1 1 calc R U . . .
C18 C 0.49494(17) 0.66057(18) 0.20307(13) 0.0141(4) Uani 1 1 d . . . . .
C19 C 0.59451(17) 0.63256(17) 0.18346(13) 0.0137(4) Uani 1 1 d . . . . .
C20 C 0.56395(18) 0.52218(17) 0.12410(14) 0.0150(4) Uani 1 1 d . . . . .
H20 H 0.4788 0.4691 0.0989 0.018 Uiso 1 1 calc R U . . .
C21 C 0.64318(18) 0.47738(17) 0.09569(13) 0.0136(4) Uani 1 1 d . . . . .
C22 C 0.58186(19) 0.34768(17) 0.03909(14) 0.0186(4) Uani 1 1 d . . . . .
H22A H 0.6087 0.3410 -0.0212 0.028 Uiso 1 1 calc R U . . .
H22B H 0.4926 0.3136 0.0271 0.028 Uiso 1 1 calc R U . . .
H22C H 0.6045 0.3042 0.0745 0.028 Uiso 1 1 calc R U . . .
C23 C 0.83433(19) 0.48505(19) 0.08103(15) 0.0193(4) Uani 1 1 d . . . . .
H23A H 0.8177 0.4631 0.0112 0.023 Uiso 1 1 calc R U . . .
H23B H 0.8066 0.4108 0.0995 0.023 Uiso 1 1 calc R U . . .
C24 C 0.9711(2) 0.5658(2) 0.11900(17) 0.0267(5) Uani 1 1 d . . . . .
H24A H 1.0147 0.5258 0.0914 0.040 Uiso 1 1 calc R U . . .
H24B H 0.9885 0.5834 0.1878 0.040 Uiso 1 1 calc R U . . .
H24C H 0.9985 0.6403 0.1024 0.040 Uiso 1 1 calc R U . . .
C25 C -0.13150(18) 0.21534(17) 0.05470(14) 0.0154(4) Uani 1 1 d . . . . .
H37 H -0.0539 0.2865 0.0728 0.018 Uiso 1 1 calc R U . . .
C26 C -0.21649(19) 0.19523(19) -0.02190(14) 0.0182(4) Uani 1 1 d . . . . .
H38 H -0.1968 0.2527 -0.0555 0.022 Uiso 1 1 calc R U . . .
C27 C -0.32989(19) 0.09167(19) -0.04947(15) 0.0198(4) Uani 1 1 d . . . . .
H39 H -0.3884 0.0785 -0.1013 0.024 Uiso 1 1 calc R U . . .
C28 C -0.35758(18) 0.00717(19) -0.00085(14) 0.0192(4) Uani 1 1 d . . . . .
H40 H -0.4346 -0.0647 -0.0204 0.023 Uiso 1 1 calc R U . . .
C29 C -0.27362(18) 0.02721(18) 0.07577(14) 0.0160(4) Uani 1 1 d . . . . .
H41 H -0.2940 -0.0308 0.1088 0.019 Uiso 1 1 calc R U . . .
C30 C -0.15850(17) 0.13229(17) 0.10558(13) 0.0130(4) Uani 1 1 d . . . . .
C31 C -0.06438(17) 0.15760(17) 0.18745(13) 0.0135(4) Uani 1 1 d . . . . .
C32 C -0.09882(18) 0.09260(17) 0.25098(13) 0.0151(4) Uani 1 1 d . . . . .
H44 H -0.1843 0.0388 0.2416 0.018 Uiso 1 1 calc R U . . .
C33 C -0.02319(18) 0.09508(17) 0.32925(14) 0.0149(4) Uani 1 1 d . . . . .
C34 C -0.08717(19) 0.00310(18) 0.37992(14) 0.0184(4) Uani 1 1 d . . . . .
H46A H -0.0678 0.0426 0.4479 0.028 Uiso 1 1 calc R U . . .
H46B H -0.0591 -0.0553 0.3683 0.028 Uiso 1 1 calc R U . . .
H46C H -0.1761 -0.0377 0.3565 0.028 Uiso 1 1 calc R U . . .
C35 C 0.17131(19) 0.16804(19) 0.43255(14) 0.0200(4) Uani 1 1 d . . . . .
H47A H 0.2523 0.1864 0.4171 0.024 Uiso 1 1 calc R U . . .
H47B H 0.1317 0.0868 0.4399 0.024 Uiso 1 1 calc R U . . .
C36 C 0.1893(2) 0.25717(19) 0.52469(14) 0.0231(5) Uani 1 1 d . . . . .
H48A H 0.2447 0.2565 0.5742 0.035 Uiso 1 1 calc R U . . .
H48B H 0.1099 0.2353 0.5427 0.035 Uiso 1 1 calc R U . . .
H48C H 0.2251 0.3372 0.5167 0.035 Uiso 1 1 calc R U . . .
C37 C 0.50754(19) 0.23138(18) 0.25447(14) 0.0176(4) Uani 1 1 d . . . . .
H25 H 0.4245 0.1694 0.2417 0.021 Uiso 1 1 calc R U . . .
C38 C 0.5991(2) 0.2028(2) 0.23893(15) 0.0203(4) Uani 1 1 d . . . . .
H26 H 0.5779 0.1216 0.2152 0.024 Uiso 1 1 calc R U . . .
C39 C 0.7209(2) 0.2917(2) 0.25778(14) 0.0216(4) Uani 1 1 d . . . . .
H27 H 0.7834 0.2718 0.2487 0.026 Uiso 1 1 calc R U . . .
C40 C 0.75064(19) 0.4105(2) 0.29020(14) 0.0202(4) Uani 1 1 d . . . . .
H28 H 0.8338 0.4720 0.3024 0.024 Uiso 1 1 calc R U . . .
C41 C 0.65992(18) 0.43973(19) 0.30477(14) 0.0171(4) Uani 1 1 d . . . . .
H29 H 0.6815 0.5212 0.3259 0.021 Uiso 1 1 calc R U . . .
C42 C 0.53671(17) 0.35059(17) 0.28876(13) 0.0142(4) Uani 1 1 d . . . . .
C43 C 0.43701(18) 0.37860(17) 0.30792(13) 0.0144(4) Uani 1 1 d . . . . .
C44 C 0.46576(18) 0.48664(17) 0.36992(14) 0.0161(4) Uani 1 1 d . . . . .
H32 H 0.5506 0.5397 0.3964 0.019 Uiso 1 1 calc R U . . .
C45 C 0.38545(18) 0.52934(17) 0.39951(13) 0.0145(4) Uani 1 1 d . . . . .
C46 C 0.44646(19) 0.65754(18) 0.45988(15) 0.0210(4) Uani 1 1 d . . . . .
H34A H 0.4196 0.6608 0.5202 0.032 Uiso 1 1 calc R U . . .
H34B H 0.4236 0.7031 0.4271 0.032 Uiso 1 1 calc R U . . .
H34C H 0.5358 0.6919 0.4715 0.032 Uiso 1 1 calc R U . . .
C47 C 0.19400(19) 0.51917(18) 0.41493(15) 0.0188(4) Uani 1 1 d . . . . .
H35A H 0.2181 0.5927 0.3960 0.023 Uiso 1 1 calc R U . . .
H35B H 0.2141 0.5421 0.4847 0.023 Uiso 1 1 calc R U . . .
C48 C 0.0570(2) 0.4360(2) 0.38058(19) 0.0307(5) Uani 1 1 d . . . . .
H36A H 0.0132 0.4736 0.4116 0.046 Uiso 1 1 calc R U . . .
H36B H 0.0336 0.3611 0.3958 0.046 Uiso 1 1 calc R U . . .
H36C H 0.0357 0.4194 0.3121 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 1.9284(14) . ?
Co1 O1 1.9344(14) . ?
Co1 N2 1.9732(16) . ?
Co1 N1 1.9764(16) . ?
Co2 O4 1.9325(14) . ?
Co2 O3 1.9346(14) . ?
Co2 N3 1.9636(17) . ?
Co2 N4 1.9720(17) . ?
N1 C9 1.319(2) . ?
N1 C11 1.474(2) . ?
N2 C21 1.318(2) . ?
N2 C23 1.473(2) . ?
N3 C33 1.311(2) . ?
N3 C35 1.469(2) . ?
N4 C45 1.322(2) . ?
N4 C47 1.472(2) . ?
O1 C7 1.302(2) . ?
O2 C19 1.298(2) . ?
O3 C31 1.309(2) . ?
O4 C43 1.300(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.393(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(3) . ?
C7 C8 1.378(3) . ?
C8 C9 1.426(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.501(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.504(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.389(3) . ?
C13 C18 1.397(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.402(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.497(3) . ?
C19 C20 1.384(3) . ?
C20 C21 1.426(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.509(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.514(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.390(3) . ?
C25 C30 1.400(3) . ?
C25 H37 0.9500 . ?
C26 C27 1.386(3) . ?
C26 H38 0.9500 . ?
C27 C28 1.390(3) . ?
C27 H39 0.9500 . ?
C28 C29 1.382(3) . ?
C28 H40 0.9500 . ?
C29 C30 1.407(3) . ?
C29 H41 0.9500 . ?
C30 C31 1.494(3) . ?
C31 C32 1.377(3) . ?
C32 C33 1.433(3) . ?
C32 H44 0.9500 . ?
C33 C34 1.511(3) . ?
C34 H46A 0.9800 . ?
C34 H46B 0.9800 . ?
C34 H46C 0.9800 . ?
C35 C36 1.517(3) . ?
C35 H47A 0.9900 . ?
C35 H47B 0.9900 . ?
C36 H48A 0.9800 . ?
C36 H48B 0.9800 . ?
C36 H48C 0.9800 . ?
C37 C38 1.392(3) . ?
C37 C42 1.401(3) . ?
C37 H25 0.9500 . ?
C38 C39 1.385(3) . ?
C38 H26 0.9500 . ?
C39 C40 1.392(3) . ?
C39 H27 0.9500 . ?
C40 C41 1.385(3) . ?
C40 H28 0.9500 . ?
C41 C42 1.402(3) . ?
C41 H29 0.9500 . ?
C42 C43 1.497(3) . ?
C43 C44 1.381(3) . ?
C44 C45 1.425(3) . ?
C44 H32 0.9500 . ?
C45 C46 1.510(3) . ?
C46 H34A 0.9800 . ?
C46 H34B 0.9800 . ?
C46 H34C 0.9800 . ?
C47 C48 1.514(3) . ?
C47 H35A 0.9900 . ?
C47 H35B 0.9900 . ?
C48 H36A 0.9800 . ?
C48 H36B 0.9800 . ?
C48 H36C 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
O2 Co1 O1 113.75(6) . . ?
O2 Co1 N2 97.66(6) . . ?
O1 Co1 N2 114.91(6) . . ?
O2 Co1 N1 113.76(6) . . ?
O1 Co1 N1 97.67(6) . . ?
N2 Co1 N1 120.12(7) . . ?
O4 Co2 O3 117.72(6) . . ?
O4 Co2 N3 108.99(7) . . ?
O3 Co2 N3 96.79(6) . . ?
O4 Co2 N4 97.39(6) . . ?
O3 Co2 N4 119.67(6) . . ?
N3 Co2 N4 117.08(7) . . ?
C9 N1 C11 117.11(16) . . ?
C9 N1 Co1 121.51(13) . . ?
C11 N1 Co1 121.20(12) . . ?
C21 N2 C23 117.77(16) . . ?
C21 N2 Co1 121.31(13) . . ?
C23 N2 Co1 120.89(13) . . ?
C33 N3 C35 120.98(17) . . ?
C33 N3 Co2 123.44(13) . . ?
C35 N3 Co2 115.58(13) . . ?
C45 N4 C47 117.02(16) . . ?
C45 N4 Co2 121.67(13) . . ?
C47 N4 Co2 121.30(13) . . ?
C7 O1 Co1 122.72(12) . . ?
C19 O2 Co1 122.26(12) . . ?
C31 O3 Co2 122.28(12) . . ?
C43 O4 Co2 122.47(12) . . ?
C2 C1 C6 121.20(19) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.76(19) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.92(18) . . ?
C1 C6 C7 119.17(17) . . ?
C5 C6 C7 122.88(18) . . ?
O1 C7 C8 125.02(17) . . ?
O1 C7 C6 114.75(16) . . ?
C8 C7 C6 120.23(17) . . ?
C7 C8 C9 129.37(18) . . ?
C7 C8 H8 115.3 . . ?
C9 C8 H8 115.3 . . ?
N1 C9 C8 123.27(17) . . ?
N1 C9 C10 120.20(17) . . ?
C8 C9 C10 116.53(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 112.16(17) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 121.1(2) . . ?
C14 C13 H13 119.4 . . ?
C18 C13 H13 119.4 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 117.96(18) . . ?
C13 C18 C19 119.33(17) . . ?
C17 C18 C19 122.70(18) . . ?
O2 C19 C20 125.29(18) . . ?
O2 C19 C18 115.29(17) . . ?
C20 C19 C18 119.38(17) . . ?
C19 C20 C21 128.66(18) . . ?
C19 C20 H20 115.7 . . ?
C21 C20 H20 115.7 . . ?
N2 C21 C20 123.63(18) . . ?
N2 C21 C22 119.89(17) . . ?
C20 C21 C22 116.47(17) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 C24 112.04(17) . . ?
N2 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
N2 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 120.98(18) . . ?
C26 C25 H37 119.5 . . ?
C30 C25 H37 119.5 . . ?
C27 C26 C25 120.23(19) . . ?
C27 C26 H38 119.9 . . ?
C25 C26 H38 119.9 . . ?
C26 C27 C28 119.63(19) . . ?
C26 C27 H39 120.2 . . ?
C28 C27 H39 120.2 . . ?
C29 C28 C27 120.31(19) . . ?
C29 C28 H40 119.8 . . ?
C27 C28 H40 119.8 . . ?
C28 C29 C30 120.99(19) . . ?
C28 C29 H41 119.5 . . ?
C30 C29 H41 119.5 . . ?
C25 C30 C29 117.85(18) . . ?
C25 C30 C31 119.16(17) . . ?
C29 C30 C31 122.99(17) . . ?
O3 C31 C32 125.56(18) . . ?
O3 C31 C30 114.99(17) . . ?
C32 C31 C30 119.45(17) . . ?
C31 C32 C33 128.78(18) . . ?
C31 C32 H44 115.6 . . ?
C33 C32 H44 115.6 . . ?
N3 C33 C32 122.20(18) . . ?
N3 C33 C34 121.70(18) . . ?
C32 C33 C34 116.09(17) . . ?
C33 C34 H46A 109.5 . . ?
C33 C34 H46B 109.5 . . ?
H46A C34 H46B 109.5 . . ?
C33 C34 H46C 109.5 . . ?
H46A C34 H46C 109.5 . . ?
H46B C34 H46C 109.5 . . ?
N3 C35 C36 111.22(17) . . ?
N3 C35 H47A 109.4 . . ?
C36 C35 H47A 109.4 . . ?
N3 C35 H47B 109.4 . . ?
C36 C35 H47B 109.4 . . ?
H47A C35 H47B 108.0 . . ?
C35 C36 H48A 109.5 . . ?
C35 C36 H48B 109.5 . . ?
H48A C36 H48B 109.5 . . ?
C35 C36 H48C 109.5 . . ?
H48A C36 H48C 109.5 . . ?
H48B C36 H48C 109.5 . . ?
C38 C37 C42 120.64(19) . . ?
C38 C37 H25 119.7 . . ?
C42 C37 H25 119.7 . . ?
C39 C38 C37 120.6(2) . . ?
C39 C38 H26 119.7 . . ?
C37 C38 H26 119.7 . . ?
C38 C39 C40 119.2(2) . . ?
C38 C39 H27 120.4 . . ?
C40 C39 H27 120.4 . . ?
C41 C40 C39 120.5(2) . . ?
C41 C40 H28 119.7 . . ?
C39 C40 H28 119.7 . . ?
C40 C41 C42 120.86(19) . . ?
C40 C41 H29 119.6 . . ?
C42 C41 H29 119.6 . . ?
C37 C42 C41 118.09(18) . . ?
C37 C42 C43 119.53(17) . . ?
C41 C42 C43 122.37(18) . . ?
O4 C43 C44 125.21(18) . . ?
O4 C43 C42 114.88(17) . . ?
C44 C43 C42 119.87(18) . . ?
C43 C44 C45 128.79(19) . . ?
C43 C44 H32 115.6 . . ?
C45 C44 H32 115.6 . . ?
N4 C45 C44 123.47(18) . . ?
N4 C45 C46 120.52(18) . . ?
C44 C45 C46 116.01(18) . . ?
C45 C46 H34A 109.5 . . ?
C45 C46 H34B 109.5 . . ?
H34A C46 H34B 109.5 . . ?
C45 C46 H34C 109.5 . . ?
H34A C46 H34C 109.5 . . ?
H34B C46 H34C 109.5 . . ?
N4 C47 C48 111.81(17) . . ?
N4 C47 H35A 109.3 . . ?
C48 C47 H35A 109.3 . . ?
N4 C47 H35B 109.3 . . ?
C48 C47 H35B 109.3 . . ?
H35A C47 H35B 107.9 . . ?
C47 C48 H36A 109.5 . . ?
C47 C48 H36B 109.5 . . ?
H36A C48 H36B 109.5 . . ?
C47 C48 H36C 109.5 . . ?
H36A C48 H36C 109.5 . . ?
H36B C48 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 C7 -178.63(18) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 178.20(19) . . . . ?
Co1 O1 C7 C8 2.6(3) . . . . ?
Co1 O1 C7 C6 -177.97(12) . . . . ?
C1 C6 C7 O1 13.0(3) . . . . ?
C5 C6 C7 O1 -164.97(18) . . . . ?
C1 C6 C7 C8 -167.51(18) . . . . ?
C5 C6 C7 C8 14.5(3) . . . . ?
O1 C7 C8 C9 2.9(3) . . . . ?
C6 C7 C8 C9 -176.48(18) . . . . ?
C11 N1 C9 C8 -178.11(17) . . . . ?
Co1 N1 C9 C8 6.7(3) . . . . ?
C11 N1 C9 C10 2.5(3) . . . . ?
Co1 N1 C9 C10 -172.71(13) . . . . ?
C7 C8 C9 N1 -8.3(3) . . . . ?
C7 C8 C9 C10 171.19(19) . . . . ?
C9 N1 C11 C12 170.24(19) . . . . ?
Co1 N1 C11 C12 -14.6(2) . . . . ?
C18 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C14 C13 C18 C17 -2.2(3) . . . . ?
C14 C13 C18 C19 177.18(18) . . . . ?
C16 C17 C18 C13 2.3(3) . . . . ?
C16 C17 C18 C19 -177.10(18) . . . . ?
Co1 O2 C19 C20 8.4(3) . . . . ?
Co1 O2 C19 C18 -169.25(12) . . . . ?
C13 C18 C19 O2 19.8(3) . . . . ?
C17 C18 C19 O2 -160.82(18) . . . . ?
C13 C18 C19 C20 -157.97(18) . . . . ?
C17 C18 C19 C20 21.4(3) . . . . ?
O2 C19 C20 C21 2.2(3) . . . . ?
C18 C19 C20 C21 179.69(18) . . . . ?
C23 N2 C21 C20 -178.81(18) . . . . ?
Co1 N2 C21 C20 -0.5(3) . . . . ?
C23 N2 C21 C22 1.6(3) . . . . ?
Co1 N2 C21 C22 179.94(13) . . . . ?
C19 C20 C21 N2 -6.6(3) . . . . ?
C19 C20 C21 C22 173.01(19) . . . . ?
C21 N2 C23 C24 -173.88(18) . . . . ?
Co1 N2 C23 C24 7.8(2) . . . . ?
C30 C25 C26 C27 -0.3(3) . . . . ?
C25 C26 C27 C28 -0.9(3) . . . . ?
C26 C27 C28 C29 1.3(3) . . . . ?
C27 C28 C29 C30 -0.6(3) . . . . ?
C26 C25 C30 C29 0.9(3) . . . . ?
C26 C25 C30 C31 -179.99(17) . . . . ?
C28 C29 C30 C25 -0.5(3) . . . . ?
C28 C29 C30 C31 -179.52(18) . . . . ?
Co2 O3 C31 C32 -3.8(3) . . . . ?
Co2 O3 C31 C30 176.37(11) . . . . ?
C25 C30 C31 O3 -15.5(3) . . . . ?
C29 C30 C31 O3 163.57(17) . . . . ?
C25 C30 C31 C32 164.67(18) . . . . ?
C29 C30 C31 C32 -16.3(3) . . . . ?
O3 C31 C32 C33 -5.3(3) . . . . ?
C30 C31 C32 C33 174.51(18) . . . . ?
C35 N3 C33 C32 -176.91(17) . . . . ?
Co2 N3 C33 C32 3.4(3) . . . . ?
C35 N3 C33 C34 2.2(3) . . . . ?
Co2 N3 C33 C34 -177.48(14) . . . . ?
C31 C32 C33 N3 5.5(3) . . . . ?
C31 C32 C33 C34 -173.70(19) . . . . ?
C33 N3 C35 C36 -96.9(2) . . . . ?
Co2 N3 C35 C36 82.86(19) . . . . ?
C42 C37 C38 C39 0.5(3) . . . . ?
C37 C38 C39 C40 -1.7(3) . . . . ?
C38 C39 C40 C41 0.9(3) . . . . ?
C39 C40 C41 C42 1.1(3) . . . . ?
C38 C37 C42 C41 1.4(3) . . . . ?
C38 C37 C42 C43 -177.94(18) . . . . ?
C40 C41 C42 C37 -2.2(3) . . . . ?
C40 C41 C42 C43 177.14(18) . . . . ?
Co2 O4 C43 C44 -8.9(3) . . . . ?
Co2 O4 C43 C42 168.83(12) . . . . ?
C37 C42 C43 O4 -20.2(3) . . . . ?
C41 C42 C43 O4 160.50(18) . . . . ?
C37 C42 C43 C44 157.73(18) . . . . ?
C41 C42 C43 C44 -21.6(3) . . . . ?
O4 C43 C44 C45 -0.6(3) . . . . ?
C42 C43 C44 C45 -178.30(19) . . . . ?
C47 N4 C45 C44 178.03(18) . . . . ?
Co2 N4 C45 C44 -0.9(3) . . . . ?
C47 N4 C45 C46 -2.5(3) . . . . ?
Co2 N4 C45 C46 178.56(14) . . . . ?
C43 C44 C45 N4 6.2(3) . . . . ?
C43 C44 C45 C46 -173.3(2) . . . . ?
C45 N4 C47 C48 178.20(18) . . . . ?
Co2 N4 C47 C48 -2.9(2) . . . . ?

_refine_diff_density_max         1.625
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_xbp56
_database_code_depnum_ccdc_archive 'CCDC 1531603'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Zn(B-Et)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 O2 Zn'
_chemical_formula_sum            'C24 H28 N2 O2 Zn'
_chemical_formula_weight         441.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3939(10)
_cell_length_b                   12.6055(17)
_cell_length_c                   13.2996(18)
_cell_angle_alpha                116.469(2)
_cell_angle_beta                 105.648(2)
_cell_angle_gamma                93.280(2)
_cell_volume                     1045.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    4863
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      31.37

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.197
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6559
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            15597
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.812
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6341
_reflns_number_gt                4688
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 The ethyl arm from N1 containing C11 and C12 is disordered over two
orientations with refined occupancies of 0.41:0.59.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+1.2576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6341
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.31388(5) 0.37119(3) 0.70706(2) 0.03449(10) Uani 1 1 d . . . . .
N1A N 0.5352(11) 0.4228(7) 0.8286(7) 0.0168(13) Uani 0.416(11) 1 d . . P A 1
N1B N 0.5743(7) 0.3907(5) 0.8358(4) 0.0162(9) Uani 0.584(11) 1 d . . P A 2
N2 N 0.2976(3) 0.28514(18) 0.53780(16) 0.0265(4) Uani 1 1 d . . . . .
O1 O 0.1491(2) 0.29329(15) 0.75739(13) 0.0264(3) Uani 1 1 d . . . . .
O2 O 0.2499(3) 0.52083(16) 0.71185(15) 0.0369(4) Uani 1 1 d . . . . .
C1 C -0.1090(3) 0.14992(19) 0.78118(19) 0.0218(4) Uani 1 1 d . . . . .
H1 H -0.1386 0.1568 0.7105 0.026 Uiso 1 1 calc R U . . .
C2 C -0.2490(3) 0.0881(2) 0.7992(2) 0.0279(5) Uani 1 1 d . . . . .
H2 H -0.3728 0.0525 0.7406 0.033 Uiso 1 1 calc R U . . .
C3 C -0.2077(4) 0.0785(2) 0.9023(2) 0.0351(6) Uani 1 1 d . . . . .
H3 H -0.3030 0.0363 0.9146 0.042 Uiso 1 1 calc R U . . .
C4 C -0.0280(4) 0.1304(2) 0.9872(2) 0.0348(6) Uani 1 1 d . . . . .
H4 H -0.0003 0.1245 1.0584 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1122(4) 0.1909(2) 0.9696(2) 0.0272(5) Uani 1 1 d . . . . .
H5 H 0.2359 0.2255 1.0284 0.033 Uiso 1 1 calc R U . . .
C6 C 0.0735(3) 0.20168(19) 0.86541(18) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.2197(3) 0.26815(19) 0.84262(18) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.4094(3) 0.2981(2) 0.9120(2) 0.0268(5) Uani 1 1 d . . . . .
H8 H 0.4382 0.2687 0.9678 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5697(3) 0.3676(2) 0.9119(2) 0.0335(6) Uani 1 1 d . . . . .
C10 C 0.7559(3) 0.3979(3) 1.0108(2) 0.0441(7) Uani 1 1 d . . . . .
H10A H 0.7346 0.3673 1.0635 0.066 Uiso 1 1 calc R U . . .
H10B H 0.8018 0.4859 1.0563 0.066 Uiso 1 1 calc R U . . .
H10C H 0.8521 0.3601 0.9765 0.066 Uiso 1 1 calc R U . . .
C11A C 0.6918(9) 0.5041(6) 0.8329(5) 0.0239(18) Uani 0.416(11) 1 d . . P A 1
H11A H 0.7891 0.5434 0.9134 0.029 Uiso 0.416(11) 1 calc R U P A 1
H11B H 0.6399 0.5685 0.8182 0.029 Uiso 0.416(11) 1 calc R U P A 1
C12A C 0.7868(18) 0.4369(12) 0.7416(11) 0.031(2) Uani 0.416(11) 1 d . . P A 1
H12A H 0.8811 0.4950 0.7418 0.047 Uiso 0.416(11) 1 calc R U P A 1
H12B H 0.6892 0.3926 0.6625 0.047 Uiso 0.416(11) 1 calc R U P A 1
H12C H 0.8515 0.3797 0.7615 0.047 Uiso 0.416(11) 1 calc R U P A 1
C11B C 0.7562(6) 0.4549(5) 0.8469(3) 0.0235(13) Uani 0.584(11) 1 d . . P A 2
H11C H 0.8582 0.4099 0.8588 0.028 Uiso 0.584(11) 1 calc R U P A 2
H11D H 0.7926 0.5362 0.9177 0.028 Uiso 0.584(11) 1 calc R U P A 2
C12B C 0.7423(14) 0.4681(12) 0.7389(10) 0.052(3) Uani 0.584(11) 1 d . . P A 2
H12D H 0.8672 0.5090 0.7483 0.078 Uiso 0.584(11) 1 calc R U P A 2
H12E H 0.6460 0.5162 0.7292 0.078 Uiso 0.584(11) 1 calc R U P A 2
H12F H 0.7047 0.3878 0.6686 0.078 Uiso 0.584(11) 1 calc R U P A 2
C13 C 0.2954(4) 0.7638(2) 0.7738(2) 0.0343(6) Uani 1 1 d . . . . .
H13 H 0.3322 0.7425 0.8354 0.041 Uiso 1 1 calc R U . . .
C14 C 0.2956(4) 0.8839(2) 0.8029(2) 0.0388(6) Uani 1 1 d . . . . .
H14 H 0.3328 0.9440 0.8840 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2417(4) 0.9170(2) 0.7143(3) 0.0383(6) Uani 1 1 d . . . . .
H15 H 0.2442 0.9995 0.7343 0.046 Uiso 1 1 calc R U . . .
C16 C 0.1840(4) 0.8275(2) 0.5958(2) 0.0349(6) Uani 1 1 d . . . . .
H16 H 0.1449 0.8491 0.5345 0.042 Uiso 1 1 calc R U . . .
C17 C 0.1830(3) 0.7077(2) 0.5664(2) 0.0308(5) Uani 1 1 d . . . . .
H17 H 0.1418 0.6476 0.4851 0.037 Uiso 1 1 calc R U . . .
C18 C 0.2417(3) 0.6735(2) 0.6549(2) 0.0293(5) Uani 1 1 d . . . . .
C19 C 0.2513(3) 0.5455(2) 0.6273(2) 0.0284(5) Uani 1 1 d . . . . .
C20 C 0.2661(3) 0.4652(2) 0.51857(19) 0.0279(5) Uani 1 1 d . . . . .
H20 H 0.2685 0.4974 0.4664 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2783(3) 0.3416(2) 0.47467(18) 0.0258(5) Uani 1 1 d . . . . .
C22 C 0.2659(4) 0.2732(2) 0.3452(2) 0.0321(5) Uani 1 1 d . . . . .
H22A H 0.2551 0.3285 0.3114 0.048 Uiso 1 1 calc R U . . .
H22B H 0.1529 0.2069 0.3009 0.048 Uiso 1 1 calc R U . . .
H22C H 0.3817 0.2402 0.3396 0.048 Uiso 1 1 calc R U . . .
C23 C 0.3121(4) 0.1578(2) 0.4801(2) 0.0354(6) Uani 1 1 d . . . . .
H23A H 0.4281 0.1512 0.4558 0.042 Uiso 1 1 calc R U . . .
H23B H 0.1989 0.1115 0.4075 0.042 Uiso 1 1 calc R U . . .
C24 C 0.3230(5) 0.1037(3) 0.5621(3) 0.0474(7) Uani 1 1 d . . . . .
H24A H 0.3388 0.0198 0.5223 0.071 Uiso 1 1 calc R U . . .
H24B H 0.2045 0.1052 0.5820 0.071 Uiso 1 1 calc R U . . .
H24C H 0.4327 0.1509 0.6351 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1A 1.796(8) . ?
Zn1 O1 1.9456(15) . ?
Zn1 O2 1.949(2) . ?
Zn1 N2 1.9800(18) . ?
Zn1 N1B 2.119(6) . ?
N1A C11A 1.473(9) . ?
N1A C9 1.527(9) . ?
N1B C9 1.179(6) . ?
N1B C11B 1.466(6) . ?
N2 C21 1.308(3) . ?
N2 C23 1.464(3) . ?
O1 C7 1.295(3) . ?
O2 C19 1.295(3) . ?
C1 C6 1.391(3) . ?
C1 C2 1.394(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.504(3) . ?
C7 C8 1.376(3) . ?
C8 C9 1.434(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.512(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11A C12A 1.515(14) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C11B C12B 1.495(12) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13 C14 1.385(4) . ?
C13 C18 1.399(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.498(4) . ?
C19 C20 1.386(3) . ?
C20 C21 1.418(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.516(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.511(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
N1A Zn1 O1 101.0(2) . . ?
N1A Zn1 O2 103.2(3) . . ?
O1 Zn1 O2 114.25(7) . . ?
N1A Zn1 N2 123.3(2) . . ?
O1 Zn1 N2 117.13(7) . . ?
O2 Zn1 N2 97.60(8) . . ?
O1 Zn1 N1B 95.91(14) . . ?
O2 Zn1 N1B 115.84(17) . . ?
N2 Zn1 N1B 117.42(15) . . ?
C11A N1A C9 121.1(5) . . ?
C11A N1A Zn1 117.7(5) . . ?
C9 N1A Zn1 120.5(5) . . ?
C9 N1B C11B 118.3(4) . . ?
C9 N1B Zn1 119.5(3) . . ?
C11B N1B Zn1 121.1(3) . . ?
C21 N2 C23 117.79(19) . . ?
C21 N2 Zn1 120.79(16) . . ?
C23 N2 Zn1 121.39(16) . . ?
C7 O1 Zn1 121.32(14) . . ?
C19 O2 Zn1 121.25(16) . . ?
C6 C1 C2 120.8(2) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 C7 119.01(18) . . ?
C5 C6 C7 122.8(2) . . ?
O1 C7 C8 126.3(2) . . ?
O1 C7 C6 114.38(18) . . ?
C8 C7 C6 119.3(2) . . ?
C7 C8 C9 129.0(2) . . ?
C7 C8 H8 115.5 . . ?
C9 C8 H8 115.5 . . ?
N1B C9 C8 126.0(3) . . ?
N1B C9 C10 117.8(3) . . ?
C8 C9 C10 115.6(3) . . ?
C8 C9 N1A 119.0(3) . . ?
C10 C9 N1A 124.5(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1A C11A C12A 112.0(7) . . ?
N1A C11A H11A 109.2 . . ?
C12A C11A H11A 109.2 . . ?
N1A C11A H11B 109.2 . . ?
C12A C11A H11B 109.2 . . ?
H11A C11A H11B 107.9 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
N1B C11B C12B 111.6(5) . . ?
N1B C11B H11C 109.3 . . ?
C12B C11B H11C 109.3 . . ?
N1B C11B H11D 109.3 . . ?
C12B C11B H11D 109.3 . . ?
H11C C11B H11D 108.0 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C14 C13 C18 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C18 C13 H13 119.5 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 119.0(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 118.0(2) . . ?
C17 C18 C19 122.7(2) . . ?
C13 C18 C19 119.3(2) . . ?
O2 C19 C20 125.5(2) . . ?
O2 C19 C18 115.1(2) . . ?
C20 C19 C18 119.3(2) . . ?
C19 C20 C21 128.7(2) . . ?
C19 C20 H20 115.6 . . ?
C21 C20 H20 115.6 . . ?
N2 C21 C20 124.4(2) . . ?
N2 C21 C22 119.6(2) . . ?
C20 C21 C22 116.0(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 C24 111.5(2) . . ?
N2 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
N2 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Zn1 N1A C11A -170.9(4) . . . . ?
O2 Zn1 N1A C11A -52.5(5) . . . . ?
N2 Zn1 N1A C11A 56.0(6) . . . . ?
O1 Zn1 N1A C9 19.1(5) . . . . ?
O2 Zn1 N1A C9 137.5(4) . . . . ?
N2 Zn1 N1A C9 -114.0(4) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C6 C7 -179.7(2) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 179.0(2) . . . . ?
Zn1 O1 C7 C8 4.4(3) . . . . ?
Zn1 O1 C7 C6 -176.66(13) . . . . ?
C1 C6 C7 O1 14.1(3) . . . . ?
C5 C6 C7 O1 -164.9(2) . . . . ?
C1 C6 C7 C8 -166.9(2) . . . . ?
C5 C6 C7 C8 14.1(3) . . . . ?
O1 C7 C8 C9 3.5(4) . . . . ?
C6 C7 C8 C9 -175.4(2) . . . . ?
C11B N1B C9 C8 -175.2(3) . . . . ?
Zn1 N1B C9 C8 16.9(6) . . . . ?
C11B N1B C9 C10 -4.4(6) . . . . ?
Zn1 N1B C9 C10 -172.3(2) . . . . ?
C7 C8 C9 N1B -16.7(5) . . . . ?
C7 C8 C9 C10 172.3(2) . . . . ?
C7 C8 C9 N1A 2.5(5) . . . . ?
C11A N1A C9 C8 174.3(4) . . . . ?
Zn1 N1A C9 C8 -16.0(6) . . . . ?
C11A N1A C9 C10 5.5(7) . . . . ?
Zn1 N1A C9 C10 175.2(3) . . . . ?
C9 N1A C11A C12A 95.4(9) . . . . ?
Zn1 N1A C11A C12A -74.6(8) . . . . ?
C9 N1B C11B C12B 175.2(9) . . . . ?
Zn1 N1B C11B C12B -17.1(7) . . . . ?
C18 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C13 2.1(3) . . . . ?
C16 C17 C18 C19 -177.2(2) . . . . ?
C14 C13 C18 C17 -1.9(3) . . . . ?
C14 C13 C18 C19 177.5(2) . . . . ?
Zn1 O2 C19 C20 10.8(3) . . . . ?
Zn1 O2 C19 C18 -167.22(15) . . . . ?
C17 C18 C19 O2 -159.7(2) . . . . ?
C13 C18 C19 O2 21.0(3) . . . . ?
C17 C18 C19 C20 22.2(3) . . . . ?
C13 C18 C19 C20 -157.2(2) . . . . ?
O2 C19 C20 C21 1.6(4) . . . . ?
C18 C19 C20 C21 179.6(2) . . . . ?
C23 N2 C21 C20 -178.7(2) . . . . ?
Zn1 N2 C21 C20 -0.4(3) . . . . ?
C23 N2 C21 C22 1.8(3) . . . . ?
Zn1 N2 C21 C22 -179.91(15) . . . . ?
C19 C20 C21 N2 -7.6(4) . . . . ?
C19 C20 C21 C22 171.9(2) . . . . ?
C21 N2 C23 C24 -177.0(2) . . . . ?
Zn1 N2 C23 C24 4.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10A O2 0.98 2.64 3.374(4) 131.9 2_667
C12A H12C O1 0.98 2.51 3.330(11) 140.7 1_655
C24 H24B O1 0.98 2.63 3.276(4) 123.4 .

_refine_diff_density_max         0.488
_refine_diff_density_min         -2.342
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_xbp22
_database_code_depnum_ccdc_archive 'CCDC 1531605'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Cu(B-Bn)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 Cu N2 O2'
_chemical_formula_sum            'C34 H32 Cu N2 O2'
_chemical_formula_weight         564.15

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.4162(7)
_cell_length_b                   10.2399(8)
_cell_length_c                   14.8195(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.6690(10)
_cell_angle_gamma                90
_cell_volume                     1368.86(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    8577
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      29.44

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             590
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.832
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            23334
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.434
_diffrn_reflns_theta_max         31.592
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9053
_reflns_number_gt                8129
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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=1/[σ²(Fo²)+(0.0345P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.023(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9053
_refine_ls_number_parameters     355
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.22010(3) 0.44852(3) 0.52457(2) 0.01423(7) Uani 1 1 d . . . . .
N1 N 0.4073(2) 0.3494(2) 0.56014(13) 0.0150(4) Uani 1 1 d . . . . .
N2 N 0.0078(2) 0.48884(19) 0.49615(13) 0.0153(4) Uani 1 1 d . . . . .
O1 O 0.20550(16) 0.4410(2) 0.39266(10) 0.0170(3) Uani 1 1 d . . . . .
O2 O 0.26755(18) 0.52773(17) 0.64678(11) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.1349(3) 0.4839(2) 0.20379(16) 0.0188(5) Uani 1 1 d . . . . .
H1 H 0.0679 0.5072 0.2384 0.023 Uiso 1 1 calc R U . . .
C2 C 0.0955(3) 0.5072(3) 0.10713(17) 0.0221(5) Uani 1 1 d . . . . .
H2 H 0.0020 0.5450 0.0763 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1934(3) 0.4750(3) 0.05572(17) 0.0237(6) Uani 1 1 d . . . . .
H3 H 0.1678 0.4917 -0.0101 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3282(3) 0.4184(3) 0.10148(19) 0.0295(7) Uani 1 1 d . . . . .
H4 H 0.3957 0.3969 0.0669 0.035 Uiso 1 1 calc R U . . .
C5 C 0.3657(3) 0.3928(3) 0.19697(19) 0.0248(6) Uani 1 1 d . . . . .
H5 H 0.4574 0.3514 0.2268 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2702(2) 0.4273(2) 0.25057(16) 0.0155(5) Uani 1 1 d . . . . .
C7 C 0.3074(3) 0.4050(2) 0.35509(17) 0.0147(4) Uani 1 1 d . . . . .
C8 C 0.4396(3) 0.3477(2) 0.40427(16) 0.0162(4) Uani 1 1 d . . . . .
H8 H 0.5085 0.3291 0.3701 0.019 Uiso 1 1 calc R U . . .
C9 C 0.4820(3) 0.3140(2) 0.50165(17) 0.0153(4) Uani 1 1 d . . . . .
C10 C 0.6167(3) 0.2265(3) 0.53410(18) 0.0209(5) Uani 1 1 d . . . . .
H10A H 0.6674 0.2222 0.4849 0.031 Uiso 1 1 calc R U . . .
H10B H 0.5854 0.1387 0.5465 0.031 Uiso 1 1 calc R U . . .
H10C H 0.6844 0.2622 0.5919 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4578(3) 0.3001(2) 0.65771(17) 0.0167(5) Uani 1 1 d . . . . .
H11A H 0.4798 0.2058 0.6558 0.020 Uiso 1 1 calc R U . . .
H11B H 0.3756 0.3093 0.6865 0.020 Uiso 1 1 calc R U . . .
C12 C 0.5934(3) 0.3679(3) 0.72041(17) 0.0152(5) Uani 1 1 d . . . . .
C13 C 0.6888(3) 0.2995(3) 0.79476(18) 0.0206(5) Uani 1 1 d . . . . .
H13 H 0.6706 0.2099 0.8040 0.025 Uiso 1 1 calc R U . . .
C14 C 0.8108(3) 0.3615(3) 0.85565(19) 0.0251(6) Uani 1 1 d . . . . .
H14 H 0.8755 0.3137 0.9058 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8383(3) 0.4916(3) 0.84362(18) 0.0223(6) Uani 1 1 d . . . . .
H15 H 0.9211 0.5336 0.8857 0.027 Uiso 1 1 calc R U . . .
C16 C 0.7445(3) 0.5611(3) 0.76985(18) 0.0208(5) Uani 1 1 d . . . . .
H16 H 0.7629 0.6508 0.7613 0.025 Uiso 1 1 calc R U . . .
C17 C 0.6232(3) 0.4987(3) 0.70831(17) 0.0172(5) Uani 1 1 d . . . . .
H17 H 0.5600 0.5463 0.6574 0.021 Uiso 1 1 calc R U . . .
C18 C 0.1761(3) 0.7301(3) 0.82409(18) 0.0229(5) Uani 1 1 d . . . . .
H18 H 0.0824 0.7644 0.7897 0.027 Uiso 1 1 calc R U . . .
C19 C 0.2441(3) 0.7746(3) 0.91457(19) 0.0274(6) Uani 1 1 d . . . . .
H19 H 0.1974 0.8403 0.9412 0.033 Uiso 1 1 calc R U . . .
C20 C 0.3778(3) 0.7249(3) 0.96592(19) 0.0274(6) Uani 1 1 d . . . . .
H20 H 0.4231 0.7554 1.0281 0.033 Uiso 1 1 calc R U . . .
C21 C 0.4473(3) 0.6293(3) 0.92646(19) 0.0286(6) Uani 1 1 d . . . . .
H21 H 0.5400 0.5944 0.9618 0.034 Uiso 1 1 calc R U . . .
C22 C 0.3808(3) 0.5853(3) 0.83544(18) 0.0235(5) Uani 1 1 d . . . . .
H22 H 0.4290 0.5206 0.8088 0.028 Uiso 1 1 calc R U . . .
C23 C 0.2449(3) 0.6347(2) 0.78301(17) 0.0177(5) Uani 1 1 d . . . . .
C24 C 0.1764(3) 0.5847(2) 0.68476(16) 0.0155(4) Uani 1 1 d . . . . .
C25 C 0.0269(3) 0.5983(2) 0.64317(17) 0.0179(5) Uani 1 1 d . . . . .
H25 H -0.0279 0.6437 0.6781 0.021 Uiso 1 1 calc R U . . .
C26 C -0.0538(3) 0.5511(2) 0.55295(17) 0.0161(4) Uani 1 1 d . . . . .
C27 C -0.2194(3) 0.5751(3) 0.52583(18) 0.0214(5) Uani 1 1 d . . . . .
H27A H -0.2426 0.6342 0.5716 0.032 Uiso 1 1 calc R U . . .
H27B H -0.2713 0.4920 0.5253 0.032 Uiso 1 1 calc R U . . .
H27C H -0.2516 0.6146 0.4630 0.032 Uiso 1 1 calc R U . . .
C28 C -0.0903(2) 0.4489(3) 0.40405(14) 0.0165(4) Uani 1 1 d . . . . .
H28A H -0.1828 0.4128 0.4131 0.020 Uiso 1 1 calc R U . . .
H28B H -0.0413 0.3782 0.3785 0.020 Uiso 1 1 calc R U . . .
C29 C -0.1299(3) 0.5586(3) 0.33237(17) 0.0180(5) Uani 1 1 d . . . . .
C30 C -0.0510(3) 0.6743(3) 0.34227(19) 0.0224(5) Uani 1 1 d . . . . .
H30 H 0.0266 0.6900 0.3984 0.027 Uiso 1 1 calc R U . . .
C31 C -0.0835(4) 0.7678(3) 0.2714(2) 0.0337(7) Uani 1 1 d . . . . .
H31 H -0.0276 0.8463 0.2787 0.040 Uiso 1 1 calc R U . . .
C32 C -0.1978(4) 0.7460(3) 0.1900(2) 0.0404(9) Uani 1 1 d . . . . .
H32 H -0.2204 0.8095 0.1413 0.049 Uiso 1 1 calc R U . . .
C33 C -0.2788(4) 0.6319(4) 0.1798(2) 0.0426(9) Uani 1 1 d . . . . .
H33 H -0.3573 0.6171 0.1240 0.051 Uiso 1 1 calc R U . . .
C34 C -0.2461(3) 0.5393(3) 0.25043(19) 0.0289(6) Uani 1 1 d . . . . .
H34 H -0.3033 0.4615 0.2432 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9166(17) . ?
Cu1 O1 1.9214(14) . ?
Cu1 N2 1.965(2) . ?
Cu1 N1 1.970(2) . ?
N1 C9 1.314(3) . ?
N1 C11 1.476(3) . ?
N2 C26 1.316(3) . ?
N2 C28 1.470(3) . ?
O1 C7 1.293(3) . ?
O2 C24 1.293(3) . ?
C1 C6 1.391(3) . ?
C1 C2 1.393(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.504(3) . ?
C7 C8 1.380(3) . ?
C8 C9 1.425(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.514(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.515(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.391(4) . ?
C12 C13 1.394(3) . ?
C13 C14 1.393(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.387(4) . ?
C18 C23 1.404(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.369(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.503(3) . ?
C24 C25 1.372(3) . ?
C25 C26 1.420(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.515(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.517(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.384(4) . ?
C29 C34 1.396(4) . ?
C30 C31 1.389(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.385(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.379(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.380(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 155.18(8) . . ?
O2 Cu1 N2 93.48(7) . . ?
O1 Cu1 N2 91.08(7) . . ?
O2 Cu1 N1 90.97(8) . . ?
O1 Cu1 N1 92.81(8) . . ?
N2 Cu1 N1 160.51(8) . . ?
C9 N1 C11 118.0(2) . . ?
C9 N1 Cu1 124.94(16) . . ?
C11 N1 Cu1 116.77(15) . . ?
C26 N2 C28 117.0(2) . . ?
C26 N2 Cu1 124.94(16) . . ?
C28 N2 Cu1 118.04(14) . . ?
C7 O1 Cu1 127.16(14) . . ?
C24 O2 Cu1 126.76(15) . . ?
C6 C1 C2 121.3(2) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.8(2) . . ?
C1 C6 C7 119.1(2) . . ?
C5 C6 C7 123.1(2) . . ?
O1 C7 C8 124.2(2) . . ?
O1 C7 C6 114.70(19) . . ?
C8 C7 C6 121.1(2) . . ?
C7 C8 C9 125.9(2) . . ?
C7 C8 H8 117.0 . . ?
C9 C8 H8 117.0 . . ?
N1 C9 C8 123.6(2) . . ?
N1 C9 C10 120.8(2) . . ?
C8 C9 C10 115.5(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 115.0(2) . . ?
N1 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
N1 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C17 C12 C13 118.5(3) . . ?
C17 C12 C11 121.9(2) . . ?
C13 C12 C11 119.6(2) . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 121.0(3) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C23 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C23 C18 H18 119.8 . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.6(2) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C18 118.5(2) . . ?
C22 C23 C24 119.2(2) . . ?
C18 C23 C24 122.3(2) . . ?
O2 C24 C25 125.0(2) . . ?
O2 C24 C23 114.9(2) . . ?
C25 C24 C23 120.0(2) . . ?
C24 C25 C26 126.2(2) . . ?
C24 C25 H25 116.9 . . ?
C26 C25 H25 116.9 . . ?
N2 C26 C25 123.5(2) . . ?
N2 C26 C27 121.2(2) . . ?
C25 C26 C27 115.3(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N2 C28 C29 114.0(2) . . ?
N2 C28 H28A 108.8 . . ?
C29 C28 H28A 108.8 . . ?
N2 C28 H28B 108.8 . . ?
C29 C28 H28B 108.8 . . ?
H28A C28 H28B 107.6 . . ?
C30 C29 C34 118.5(3) . . ?
C30 C29 C28 122.9(2) . . ?
C34 C29 C28 118.6(2) . . ?
C29 C30 C31 121.0(3) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C32 C31 C30 119.6(3) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C33 C32 C31 120.0(3) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 120.2(3) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C33 C34 C29 120.7(3) . . ?
C33 C34 H34 119.6 . . ?
C29 C34 H34 119.6 . . ?

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
C6 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -2.0(4) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 179.6(2) . . . . ?
C4 C5 C6 C1 2.1(4) . . . . ?
C4 C5 C6 C7 -178.3(2) . . . . ?
Cu1 O1 C7 C8 9.6(4) . . . . ?
Cu1 O1 C7 C6 -171.87(16) . . . . ?
C1 C6 C7 O1 0.6(3) . . . . ?
C5 C6 C7 O1 -179.0(2) . . . . ?
C1 C6 C7 C8 179.2(2) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
O1 C7 C8 C9 3.0(4) . . . . ?
C6 C7 C8 C9 -175.5(2) . . . . ?
C11 N1 C9 C8 175.8(2) . . . . ?
Cu1 N1 C9 C8 2.6(3) . . . . ?
C11 N1 C9 C10 -0.7(3) . . . . ?
Cu1 N1 C9 C10 -173.89(18) . . . . ?
C7 C8 C9 N1 -9.4(4) . . . . ?
C7 C8 C9 C10 167.3(2) . . . . ?
C9 N1 C11 C12 76.8(3) . . . . ?
Cu1 N1 C11 C12 -109.5(2) . . . . ?
N1 C11 C12 C17 31.2(3) . . . . ?
N1 C11 C12 C13 -151.3(2) . . . . ?
C17 C12 C13 C14 0.3(4) . . . . ?
C11 C12 C13 C14 -177.3(2) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C13 C12 C17 C16 -0.9(4) . . . . ?
C11 C12 C17 C16 176.6(2) . . . . ?
C15 C16 C17 C12 0.8(4) . . . . ?
C23 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C18 0.0(4) . . . . ?
C21 C22 C23 C24 180.0(2) . . . . ?
C19 C18 C23 C22 0.8(4) . . . . ?
C19 C18 C23 C24 -179.2(2) . . . . ?
Cu1 O2 C24 C25 0.1(3) . . . . ?
Cu1 O2 C24 C23 178.35(15) . . . . ?
C22 C23 C24 O2 -19.2(3) . . . . ?
C18 C23 C24 O2 160.9(2) . . . . ?
C22 C23 C24 C25 159.2(2) . . . . ?
C18 C23 C24 C25 -20.8(4) . . . . ?
O2 C24 C25 C26 1.1(4) . . . . ?
C23 C24 C25 C26 -177.1(2) . . . . ?
C28 N2 C26 C25 -178.6(2) . . . . ?
Cu1 N2 C26 C25 0.4(3) . . . . ?
C28 N2 C26 C27 2.5(3) . . . . ?
Cu1 N2 C26 C27 -178.59(17) . . . . ?
C24 C25 C26 N2 -1.3(4) . . . . ?
C24 C25 C26 C27 177.7(2) . . . . ?
C26 N2 C28 C29 78.6(2) . . . . ?
Cu1 N2 C28 C29 -100.4(2) . . . . ?
N2 C28 C29 C30 17.2(3) . . . . ?
N2 C28 C29 C34 -166.4(2) . . . . ?
C34 C29 C30 C31 -1.8(4) . . . . ?
C28 C29 C30 C31 174.7(2) . . . . ?
C29 C30 C31 C32 0.9(4) . . . . ?
C30 C31 C32 C33 0.1(5) . . . . ?
C31 C32 C33 C34 -0.1(5) . . . . ?
C32 C33 C34 C29 -0.8(5) . . . . ?
C30 C29 C34 C33 1.8(4) . . . . ?
C28 C29 C34 C33 -174.9(3) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_xbp50
_database_code_depnum_ccdc_archive 'CCDC 1531602'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            alpha-Zn(B-Bn)2
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 N2 O2 Zn'
_chemical_formula_sum            'C34 H32 N2 O2 Zn'
_chemical_formula_weight         565.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   15.2491(19)
_cell_length_b                   16.231(2)
_cell_length_c                   5.5977(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1385.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      31.62

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.920
_shelx_estimated_absorpt_T_min   0.699
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            23276
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.832
_diffrn_reflns_theta_max         31.640
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4641
_reflns_number_gt                4489
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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=1/[σ²(Fo²)+(0.0369P)²+0.1030P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.036(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4641
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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
Zn1 Zn 0.5000 0.5000 0.39446(4) 0.01686(7) Uani 1 2 d S T P . .
N1 N 0.58225(8) 0.43348(8) 0.5852(2) 0.0160(2) Uani 1 1 d . . . . .
O1 O 0.45499(8) 0.40990(6) 0.2024(2) 0.0199(2) Uani 1 1 d . . . . .
C1 C 0.36169(11) 0.29678(10) -0.0564(3) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.3337 0.3467 -0.0110 0.029 Uiso 1 1 calc R U . . .
C2 C 0.32160(13) 0.24550(12) -0.2229(4) 0.0325(4) Uani 1 1 d . . . . .
H2 H 0.2667 0.2605 -0.2902 0.039 Uiso 1 1 calc R U . . .
C3 C 0.36209(14) 0.17209(12) -0.2912(4) 0.0326(4) Uani 1 1 d . . . . .
H3 H 0.3353 0.1371 -0.4061 0.039 Uiso 1 1 calc R U . . .
C4 C 0.44158(13) 0.15071(11) -0.1901(3) 0.0290(4) Uani 1 1 d . . . . .
H4 H 0.4692 0.1006 -0.2358 0.035 Uiso 1 1 calc R U . . .
C5 C 0.48177(10) 0.20139(10) -0.0225(3) 0.0222(3) Uani 1 1 d . . . . .
H5 H 0.5361 0.1854 0.0464 0.027 Uiso 1 1 calc R U . . .
C6 C 0.44255(10) 0.27608(9) 0.0454(3) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.48457(8) 0.33499(8) 0.2168(3) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.54924(10) 0.30804(9) 0.3721(3) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.5659 0.2519 0.3569 0.021 Uiso 1 1 calc R U . . .
C9 C 0.59412(9) 0.35410(9) 0.5525(3) 0.0153(2) Uani 1 1 d . . . . .
C10 C 0.65739(10) 0.30672(10) 0.7088(3) 0.0197(3) Uani 1 1 d . . . . .
H10A H 0.6621 0.2499 0.6508 0.030 Uiso 1 1 calc R U . . .
H10B H 0.6359 0.3065 0.8738 0.030 Uiso 1 1 calc R U . . .
H10C H 0.7152 0.3330 0.7031 0.030 Uiso 1 1 calc R U . . .
C11 C 0.62856(10) 0.47584(10) 0.7812(3) 0.0188(3) Uani 1 1 d . . . . .
H11A H 0.6314 0.4385 0.9209 0.023 Uiso 1 1 calc R U . . .
H11B H 0.5943 0.5250 0.8286 0.023 Uiso 1 1 calc R U . . .
C12 C 0.72085(9) 0.50251(12) 0.7165(2) 0.0178(2) Uani 1 1 d . . . . .
C13 C 0.78938(11) 0.48773(12) 0.8727(3) 0.0286(4) Uani 1 1 d . . . . .
H13 H 0.7786 0.4586 1.0170 0.034 Uiso 1 1 calc R U . . .
C14 C 0.87387(12) 0.51489(15) 0.8214(4) 0.0372(5) Uani 1 1 d . . . . .
H14 H 0.9201 0.5044 0.9309 0.045 Uiso 1 1 calc R U . . .
C15 C 0.89082(11) 0.55711(12) 0.6119(4) 0.0295(4) Uani 1 1 d . . . . .
H15 H 0.9484 0.5762 0.5776 0.035 Uiso 1 1 calc R U . . .
C16 C 0.82309(11) 0.57134(11) 0.4526(3) 0.0254(3) Uani 1 1 d . . . . .
H16 H 0.8344 0.5997 0.3073 0.030 Uiso 1 1 calc R U . . .
C17 C 0.73838(11) 0.54444(10) 0.5036(3) 0.0229(3) Uani 1 1 d . . . . .
H17 H 0.6923 0.5546 0.3932 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.9404(11) . ?
Zn1 O1 1.9404(11) 2_665 ?
Zn1 N1 1.9695(13) 2_665 ?
Zn1 N1 1.9695(13) . ?
N1 C9 1.3140(19) . ?
N1 C11 1.475(2) . ?
O1 C7 1.2994(17) . ?
C1 C2 1.391(2) . ?
C1 C6 1.399(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.498(2) . ?
C7 C8 1.386(2) . ?
C8 C9 1.431(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.513(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.516(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.383(2) . ?
C12 C17 1.399(2) . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 112.71(7) . 2_665 ?
O1 Zn1 N1 119.22(5) . 2_665 ?
O1 Zn1 N1 96.46(5) 2_665 2_665 ?
O1 Zn1 N1 96.46(5) . . ?
O1 Zn1 N1 119.22(5) 2_665 . ?
N1 Zn1 N1 114.35(8) 2_665 . ?
C9 N1 C11 119.66(13) . . ?
C9 N1 Zn1 123.35(10) . . ?
C11 N1 Zn1 116.92(9) . . ?
C7 O1 Zn1 123.24(10) . . ?
C2 C1 C6 121.09(16) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.00(17) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.37(16) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.96(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.39(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.18(14) . . ?
C1 C6 C7 118.97(14) . . ?
C5 C6 C7 122.83(14) . . ?
O1 C7 C8 125.54(13) . . ?
O1 C7 C6 114.15(12) . . ?
C8 C7 C6 120.31(12) . . ?
C7 C8 C9 128.20(13) . . ?
C7 C8 H8 115.9 . . ?
C9 C8 H8 115.9 . . ?
N1 C9 C8 123.02(13) . . ?
N1 C9 C10 120.38(13) . . ?
C8 C9 C10 116.60(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 113.58(12) . . ?
N1 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C17 118.60(14) . . ?
C13 C12 C11 120.05(14) . . ?
C17 C12 C11 121.31(13) . . ?
C12 C13 C14 120.93(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.33(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.33(16) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.50(17) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.29(16) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?

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
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 C6 C7 177.66(17) . . . . ?
C4 C5 C6 C1 1.3(2) . . . . ?
C4 C5 C6 C7 -177.22(16) . . . . ?
Zn1 O1 C7 C8 2.0(2) . . . . ?
Zn1 O1 C7 C6 -177.82(9) . . . . ?
C1 C6 C7 O1 -19.2(2) . . . . ?
C5 C6 C7 O1 159.29(14) . . . . ?
C1 C6 C7 C8 160.97(15) . . . . ?
C5 C6 C7 C8 -20.5(2) . . . . ?
O1 C7 C8 C9 2.7(2) . . . . ?
C6 C7 C8 C9 -177.49(14) . . . . ?
C11 N1 C9 C8 177.67(13) . . . . ?
Zn1 N1 C9 C8 0.9(2) . . . . ?
C11 N1 C9 C10 -2.2(2) . . . . ?
Zn1 N1 C9 C10 -178.98(10) . . . . ?
C7 C8 C9 N1 -4.3(2) . . . . ?
C7 C8 C9 C10 175.60(14) . . . . ?
C9 N1 C11 C12 84.30(17) . . . . ?
Zn1 N1 C11 C12 -98.74(13) . . . . ?
N1 C11 C12 C13 -133.96(17) . . . . ?
N1 C11 C12 C17 48.0(2) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?
C11 C12 C13 C14 -177.18(18) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
C11 C12 C17 C16 177.34(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11B O1 0.99 2.46 3.2591(19) 137.3 2_666

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.054

