# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_19120_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2083107'
loop_
_audit_author_name
_audit_author_address
'Veronica Carta'
;Indiana University
United States of America
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
acabelof@iu.edu
dbeagan@iu.edu
vcarta@iu.edu
caulton@indiana.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H28 N4 Ni O6), 1.25(C H2 Cl2)'
_chemical_formula_sum            'C45.25 H58.50 Cl2.50 N8 Ni2 O12'
_chemical_formula_weight         1112.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.981(2)
_cell_length_b                   13.932(2)
_cell_length_c                   25.176(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.521(4)
_cell_angle_gamma                90
_cell_volume                     5209.4(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2463
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      21.30
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.764
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1157 before and 0.0819 after correction. The Ratio of minimum to maximum transmission is 0.7978. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light green'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2322
_exptl_crystal_preparation       synthesized
_exptl_crystal_recrystallization_method 
'vapour diffusion of dichloromethane into a cyclohexane solution'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1784
_diffrn_reflns_av_unetI/netI     0.1852
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            54924
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_min         2.231
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker VENTURE D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7264
_reflns_number_total             12914
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         12914
_refine_ls_number_restraints     630
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0942
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0765P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1956
_refine_ls_wR_factor_ref         0.2307
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1-C1 \\sim Cl1A-C1
 with sigma of 0.01
 Cl2-C1 \\sim Cl2A-C1
 with sigma of 0.01
 Cl4-C2 \\sim Cl3-C2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C21A \\sim C20A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
C7A \\sim C6A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl2A) = Uanis(Cl2)
Uanis(Cl1A) = Uanis(Cl1)
Uanis(Cl4) = Uanis(Cl3) = Uanis(C2)
Uanis(C7) = Uanis(C7A)
Uanis(C21) = Uanis(C21A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H1BC)=Sof(H1BD)=Sof(Cl2A)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(H1AA)=Sof(H1AB)=FVAR(1)
 Fixed Sof: Cl3(0.25) Cl4(0.25) C2(0.25) H2A(0.25) H2B(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C2(H2A,H2B)
6.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), C5(H5), C8(H8), C5A(H5A), C8A(H8A), C19A(H19A), C22A(H22A)
6.c Idealised Me refined as rotating group:
 C18A(H18D,H18E,H18F), C15(H15A,H15B,H15C), C24A(H24D,H24E,H24F), C10(H10A,
 H10B,H10C), C15A(H15D,H15E,H15F), C13(H13A,H13B,H13C), C24(H24A,H24B,H24C),
 C3A(H3AA,H3AB,H3AC), C18(H18A,H18B,H18C), C13A(H13D,H13E,H13F), C3(H3A,H3B,
 H3C), C7(H7A,H7B,H7C), C10A(H10D,H10E,H10F), C21(H21A,H21B,H21C), C7A(H7AA,
 H7AB,H7AC), C21A(H21D,H21E,H21F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.29354(5) 0.59235(6) 0.24219(3) 0.01456(19) Uani 1 1 d . U . . .
Ni1A Ni 0.79641(5) 0.89096(5) 0.76497(3) 0.01430(18) Uani 1 1 d . U . . .
O5 O 0.2786(3) 0.5390(3) 0.16366(16) 0.0197(9) Uani 1 1 d . U . . .
O2 O 0.1630(3) 0.6488(3) 0.23328(16) 0.0197(9) Uani 1 1 d . U . . .
O2A O 0.7017(3) 0.7938(3) 0.78700(17) 0.0219(9) Uani 1 1 d . U . . .
O5A O 0.7096(3) 0.9868(3) 0.71948(16) 0.0210(9) Uani 1 1 d . U . . .
O4A O 0.8443(2) 1.0280(3) 0.75269(15) 0.0171(9) Uani 1 1 d . U . . .
O1A O 0.7343(3) 0.9217(3) 0.83347(16) 0.0240(10) Uani 1 1 d . U . . .
O1 O 0.1877(3) 0.5021(3) 0.25907(16) 0.0234(10) Uani 1 1 d . U . . .
O4 O 0.3792(3) 0.4846(3) 0.22605(16) 0.0231(10) Uani 1 1 d . U . . .
O6A O 0.7565(3) 1.1332(3) 0.70692(18) 0.0282(11) Uani 1 1 d . U . . .
O6 O 0.3749(3) 0.4298(4) 0.14367(18) 0.0322(12) Uani 1 1 d . U . . .
O3 O 0.0496(3) 0.5559(4) 0.24296(17) 0.0304(11) Uani 1 1 d . U . . .
N3A N 0.8453(3) 0.8256(3) 0.70272(18) 0.0138(10) Uani 1 1 d . U . . .
N4A N 0.9010(3) 0.8171(3) 0.80530(17) 0.0126(9) Uani 1 1 d . U . . .
O3A O 0.6389(3) 0.8179(4) 0.8583(2) 0.0393(13) Uani 1 1 d . U . . .
N4 N 0.3437(3) 0.6381(3) 0.31796(17) 0.0120(9) Uani 1 1 d . U . . .
N3 N 0.3675(3) 0.7050(4) 0.22403(18) 0.0157(10) Uani 1 1 d . U . . .
N1A N 0.6896(3) 0.8444(4) 0.8274(2) 0.0230(11) Uani 1 1 d . U . . .
N1 N 0.1313(3) 0.5680(4) 0.24535(19) 0.0206(11) Uani 1 1 d . U . . .
N2 N 0.3448(3) 0.4826(4) 0.1760(2) 0.0204(11) Uani 1 1 d . U . . .
N2A N 0.7692(3) 1.0529(4) 0.7258(2) 0.0205(11) Uani 1 1 d . U . . .
C12 C 0.4043(4) 0.7547(4) 0.2640(2) 0.0141(11) Uani 1 1 d . U . . .
C12A C 0.9151(4) 0.7725(4) 0.7171(2) 0.0154(11) Uani 1 1 d . U . . .
C14A C 0.9442(3) 0.7644(4) 0.7758(2) 0.0134(11) Uani 1 1 d . U . . .
C11A C 0.8079(4) 0.8299(4) 0.6466(2) 0.0149(11) Uani 1 1 d . U . . .
C16 C 0.3341(4) 0.5906(4) 0.3679(2) 0.0139(11) Uani 1 1 d . U . . .
C14 C 0.3888(4) 0.7164(4) 0.3178(2) 0.0154(11) Uani 1 1 d . U . . .
C16A C 0.9164(4) 0.8105(4) 0.8627(2) 0.0147(11) Uani 1 1 d . U . . .
C9 C 0.4624(4) 0.6899(5) 0.1528(2) 0.0205(13) Uani 1 1 d . U . . .
C4 C 0.3229(4) 0.7821(4) 0.1364(2) 0.0167(12) Uani 1 1 d . U . . .
C23 C 0.2578(4) 0.6091(4) 0.3933(2) 0.0193(12) Uani 1 1 d . U . . .
C11 C 0.3853(4) 0.7287(4) 0.1697(2) 0.0161(12) Uani 1 1 d . U . . .
C19 C 0.3902(4) 0.4812(5) 0.4374(2) 0.0258(14) Uani 1 1 d . U . . .
H19 H 0.435326 0.437714 0.452569 0.031 Uiso 1 1 calc R . . . .
C18A C 0.9787(4) 0.9812(4) 0.8633(2) 0.0238(14) Uani 1 1 d . U . . .
H18D H 1.005862 0.963653 0.831256 0.036 Uiso 1 1 calc GR . . . .
H18E H 1.022116 1.018191 0.887639 0.036 Uiso 1 1 calc GR . . . .
H18F H 0.924758 1.020018 0.852840 0.036 Uiso 1 1 calc GR . . . .
C23A C 0.8928(4) 0.7291(4) 0.8890(2) 0.0189(12) Uani 1 1 d . U . . .
C17A C 0.9533(4) 0.8913(4) 0.8912(2) 0.0203(12) Uani 1 1 d . U . . .
C22 C 0.2505(4) 0.5600(5) 0.4413(2) 0.0229(13) Uani 1 1 d . U . . .
H22 H 0.198496 0.570197 0.458545 0.027 Uiso 1 1 calc R . . . .
C15 C 0.4307(4) 0.7682(5) 0.3667(2) 0.0235(14) Uani 1 1 d . U . . .
H15A H 0.495691 0.774199 0.365753 0.035 Uiso 1 1 calc GR . . . .
H15B H 0.420076 0.732041 0.398677 0.035 Uiso 1 1 calc GR . . . .
H15C H 0.404012 0.832221 0.367802 0.035 Uiso 1 1 calc GR . . . .
C17 C 0.4004(4) 0.5267(4) 0.3890(2) 0.0197(12) Uani 1 1 d . U . . .
C5 C 0.3390(4) 0.7960(5) 0.0838(2) 0.0236(14) Uani 1 1 d . U . . .
H5 H 0.297926 0.833736 0.060592 0.028 Uiso 1 1 calc R . . . .
C24A C 0.8496(4) 0.6420(5) 0.8594(2) 0.0245(14) Uani 1 1 d . U . . .
H24D H 0.815249 0.662585 0.825533 0.037 Uiso 1 1 calc GR . . . .
H24E H 0.809088 0.610549 0.881607 0.037 Uiso 1 1 calc GR . . . .
H24F H 0.896624 0.596810 0.852148 0.037 Uiso 1 1 calc GR . . . .
C4A C 0.7420(4) 0.7623(4) 0.6286(2) 0.0203(13) Uani 1 1 d . U . . .
C10 C 0.5323(4) 0.6369(5) 0.1892(3) 0.0295(16) Uani 1 1 d . U . . .
H10A H 0.504732 0.581089 0.204345 0.044 Uiso 1 1 calc GR . . . .
H10B H 0.557875 0.679425 0.218307 0.044 Uiso 1 1 calc GR . . . .
H10C H 0.580157 0.615312 0.168963 0.044 Uiso 1 1 calc GR . . . .
C8 C 0.4742(4) 0.7053(5) 0.0993(2) 0.0256(15) Uani 1 1 d . U . . .
H8 H 0.526090 0.679484 0.086533 0.031 Uiso 1 1 calc R . . . .
C5A C 0.7049(4) 0.7672(5) 0.5750(2) 0.0273(15) Uani 1 1 d . U . . .
H5A H 0.661507 0.720546 0.561598 0.033 Uiso 1 1 calc R . . . .
C15A C 1.0190(4) 0.6961(5) 0.7945(2) 0.0215(13) Uani 1 1 d . U . . .
H15D H 1.032144 0.698890 0.833609 0.032 Uiso 1 1 calc GR . . . .
H15E H 1.072903 0.713952 0.778534 0.032 Uiso 1 1 calc GR . . . .
H15F H 1.000825 0.630719 0.783461 0.032 Uiso 1 1 calc GR . . . .
C20 C 0.3153(5) 0.4978(5) 0.4643(2) 0.0272(14) Uani 1 1 d . U . . .
C6A C 0.7285(5) 0.8368(5) 0.5407(3) 0.0322(16) Uani 1 1 d . U . . .
C8A C 0.7925(4) 0.9031(6) 0.5602(2) 0.0336(17) Uani 1 1 d . U . . .
H8A H 0.809036 0.951595 0.536832 0.040 Uiso 1 1 calc R . . . .
C13 C 0.4610(4) 0.8404(5) 0.2610(2) 0.0238(14) Uani 1 1 d . U . . .
H13A H 0.467093 0.853891 0.223403 0.036 Uiso 1 1 calc GR . . . .
H13B H 0.520688 0.828822 0.280949 0.036 Uiso 1 1 calc GR . . . .
H13C H 0.432995 0.895429 0.276493 0.036 Uiso 1 1 calc GR . . . .
C9A C 0.8343(4) 0.9015(5) 0.6134(2) 0.0266(14) Uani 1 1 d . U . . .
C24 C 0.1891(4) 0.6808(5) 0.3716(2) 0.0250(14) Uani 1 1 d . U . . .
H24A H 0.171527 0.668939 0.333284 0.038 Uiso 1 1 calc GR . . . .
H24B H 0.214285 0.745524 0.376717 0.038 Uiso 1 1 calc GR . . . .
H24C H 0.136111 0.675064 0.390464 0.038 Uiso 1 1 calc GR . . . .
C3A C 0.7141(4) 0.6844(5) 0.6647(2) 0.0263(15) Uani 1 1 d . U . . .
H3AA H 0.761784 0.635961 0.670655 0.039 Uiso 1 1 calc GR . . . .
H3AB H 0.658439 0.654225 0.647728 0.039 Uiso 1 1 calc GR . . . .
H3AC H 0.703891 0.712432 0.699061 0.039 Uiso 1 1 calc GR . . . .
C18 C 0.4812(4) 0.5039(5) 0.3607(2) 0.0251(14) Uani 1 1 d . U . . .
H18A H 0.519065 0.561169 0.360281 0.038 Uiso 1 1 calc GR . . . .
H18B H 0.460525 0.483868 0.323813 0.038 Uiso 1 1 calc GR . . . .
H18C H 0.516091 0.451948 0.379659 0.038 Uiso 1 1 calc GR . . . .
C19A C 0.9652(5) 0.8854(5) 0.9467(2) 0.0279(15) Uani 1 1 d . U . . .
H19A H 0.989855 0.939268 0.966645 0.033 Uiso 1 1 calc R . . . .
C6 C 0.4136(4) 0.7563(5) 0.0642(2) 0.0246(14) Uani 1 1 d . U . . .
C13A C 0.9652(5) 0.7177(5) 0.6789(2) 0.0295(16) Uani 1 1 d . U . . .
H13D H 0.936707 0.728536 0.642112 0.044 Uiso 1 1 calc GR . . . .
H13E H 0.963903 0.649027 0.687211 0.044 Uiso 1 1 calc GR . . . .
H13F H 1.027846 0.739822 0.682538 0.044 Uiso 1 1 calc GR . . . .
C3 C 0.2408(4) 0.8268(5) 0.1557(3) 0.0295(16) Uani 1 1 d . U . . .
H3A H 0.258106 0.886657 0.174757 0.044 Uiso 1 1 calc GR . . . .
H3B H 0.215713 0.782185 0.179992 0.044 Uiso 1 1 calc GR . . . .
H3C H 0.195454 0.840409 0.124938 0.044 Uiso 1 1 calc GR . . . .
C20A C 0.9430(5) 0.8050(5) 0.9743(3) 0.0327(16) Uani 1 1 d . U . . .
C22A C 0.9066(5) 0.7278(5) 0.9447(2) 0.0293(16) Uani 1 1 d . U . . .
H22A H 0.890490 0.672019 0.962915 0.035 Uiso 1 1 calc R . . . .
C7 C 0.4274(5) 0.7685(6) 0.0065(3) 0.0471(15) Uani 1 1 d . U . . .
H7A H 0.424983 0.836834 -0.002766 0.071 Uiso 1 1 calc GR . . . .
H7B H 0.379883 0.734143 -0.016449 0.071 Uiso 1 1 calc GR . . . .
H7C H 0.486221 0.742337 0.001030 0.071 Uiso 1 1 calc GR . . . .
C10A C 0.9065(5) 0.9739(6) 0.6323(3) 0.0393(19) Uani 1 1 d . U . . .
H10D H 0.890610 1.007335 0.663969 0.059 Uiso 1 1 calc GR . . . .
H10E H 0.911444 1.020575 0.603657 0.059 Uiso 1 1 calc GR . . . .
H10F H 0.964183 0.940875 0.641342 0.059 Uiso 1 1 calc GR . . . .
C21 C 0.3049(6) 0.4461(5) 0.5163(3) 0.0440(15) Uani 1 1 d . U . . .
H21A H 0.306614 0.492938 0.545465 0.066 Uiso 1 1 calc GR . . . .
H21B H 0.354171 0.399959 0.524548 0.066 Uiso 1 1 calc GR . . . .
H21C H 0.247197 0.411949 0.512493 0.066 Uiso 1 1 calc GR . . . .
C7A C 0.6861(5) 0.8419(6) 0.4829(3) 0.0471(15) Uani 1 1 d . U . . .
H7AA H 0.701916 0.784260 0.463904 0.071 Uiso 1 1 calc GR . . . .
H7AB H 0.708383 0.898888 0.465945 0.071 Uiso 1 1 calc GR . . . .
H7AC H 0.620499 0.845994 0.481366 0.071 Uiso 1 1 calc GR . . . .
C21A C 0.9566(6) 0.8024(6) 1.0349(3) 0.0440(15) Uani 1 1 d . U . . .
H21D H 1.016318 0.827977 1.048196 0.066 Uiso 1 1 calc GR . . . .
H21E H 0.952044 0.736054 1.047099 0.066 Uiso 1 1 calc GR . . . .
H21F H 0.910334 0.841626 1.048556 0.066 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.1913(3) 0.8230(3) 0.48612(15) 0.0741(13) Uani 0.772(4) 1 d D U P A 1
Cl2 Cl 0.0865(2) 0.9467(2) 0.54416(14) 0.0691(10) Uani 0.772(4) 1 d D U P A 1
C1 C 0.1876(7) 0.8833(7) 0.5492(4) 0.073(3) Uani 1 1 d D U . . .
H1AA H 0.190654 0.835883 0.578651 0.087 Uiso 0.772(4) 1 calc R . P A 1
H1AB H 0.239268 0.927770 0.556620 0.087 Uiso 0.772(4) 1 calc R . P A 1
H1BC H 0.204957 0.950794 0.543789 0.087 Uiso 0.228(4) 1 calc R . P A 2
H1BD H 0.241033 0.848860 0.567165 0.087 Uiso 0.228(4) 1 calc R . P A 2
Cl2A Cl 0.0973(7) 0.8791(8) 0.5910(4) 0.0691(10) Uani 0.228(4) 1 d D U P A 2
Cl1A Cl 0.1518(11) 0.8296(14) 0.4868(5) 0.0741(13) Uani 0.228(4) 1 d D U P A 2
Cl3 Cl 0.3979(7) 0.9917(8) 0.4368(4) 0.070(2) Uani 0.25 1 d D U P B -1
Cl4 Cl 0.5509(7) 1.0135(8) 0.5211(4) 0.070(2) Uani 0.25 1 d D U P B -1
C2 C 0.5093(18) 0.979(3) 0.4581(12) 0.070(2) Uani 0.25 1 d D U P B -1
H2A H 0.542499 1.014505 0.432943 0.083 Uiso 0.25 1 calc R . P B -1
H2B H 0.524255 0.909961 0.454599 0.083 Uiso 0.25 1 calc R . P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O5 2.097(4) . ?
Ni1 O2 2.093(4) . ?
Ni1 O1 2.110(4) . ?
Ni1 O4 2.050(4) . ?
Ni1 N4 2.058(4) . ?
Ni1 N3 2.009(5) . ?
Ni1A O2A 2.088(4) . ?
Ni1A O5A 2.096(4) . ?
Ni1A O4A 2.077(4) . ?
Ni1A O1A 2.108(4) . ?
Ni1A N3A 2.030(5) . ?
Ni1A N4A 2.032(5) . ?
O5 N2 1.271(6) . ?
O2 N1 1.273(6) . ?
O2A N1A 1.269(6) . ?
O5A N2A 1.278(6) . ?
O4A N2A 1.283(6) . ?
O1A N1A 1.267(6) . ?
O1 N1 1.265(6) . ?
O4 N2 1.298(6) . ?
O6A N2A 1.220(6) . ?
O6 N2 1.225(6) . ?
O3 N1 1.230(6) . ?
N3A C12A 1.294(7) . ?
N3A C11A 1.450(7) . ?
N4A C14A 1.279(7) . ?
N4A C16A 1.436(7) . ?
O3A N1A 1.215(6) . ?
N4 C16 1.445(7) . ?
N4 C14 1.284(7) . ?
N3 C12 1.285(7) . ?
N3 C11 1.465(7) . ?
C12 C14 1.501(8) . ?
C12 C13 1.473(8) . ?
C12A C14A 1.491(8) . ?
C12A C13A 1.504(8) . ?
C14A C15A 1.498(8) . ?
C11A C4A 1.397(8) . ?
C11A C9A 1.392(8) . ?
C16 C23 1.404(8) . ?
C16 C17 1.387(8) . ?
C14 C15 1.493(8) . ?
C16A C23A 1.382(8) . ?
C16A C17A 1.407(8) . ?
C9 C11 1.392(8) . ?
C9 C10 1.495(8) . ?
C9 C8 1.398(8) . ?
C4 C11 1.387(8) . ?
C4 C5 1.389(8) . ?
C4 C3 1.515(8) . ?
C23 C22 1.406(8) . ?
C23 C24 1.486(8) . ?
C19 H19 0.9500 . ?
C19 C17 1.400(8) . ?
C19 C20 1.403(9) . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C18A C17A 1.509(8) . ?
C23A C24A 1.523(8) . ?
C23A C22A 1.390(8) . ?
C17A C19A 1.388(8) . ?
C22 H22 0.9500 . ?
C22 C20 1.371(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C18 1.517(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(8) . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
C4A C5A 1.390(8) . ?
C4A C3A 1.510(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C6 1.378(8) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.375(9) . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C20 C21 1.521(8) . ?
C6A C8A 1.375(9) . ?
C6A C7A 1.512(9) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.403(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C9A C10A 1.508(9) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19A H19A 0.9500 . ?
C19A C20A 1.382(9) . ?
C6 C7 1.504(8) . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C20A C22A 1.379(9) . ?
C20A C21A 1.513(9) . ?
C22A H22A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
Cl1 C1 1.803(9) . ?
Cl2 C1 1.745(10) . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 Cl2A 1.821(11) . ?
C1 Cl1A 1.759(12) . ?
Cl3 C2 1.69(2) . ?
Cl4 C2 1.70(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

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
O5 Ni1 O1 89.33(16) . . ?
O2 Ni1 O5 92.82(15) . . ?
O2 Ni1 O1 61.89(16) . . ?
O4 Ni1 O5 62.97(16) . . ?
O4 Ni1 O2 148.69(16) . . ?
O4 Ni1 O1 96.32(17) . . ?
O4 Ni1 N4 104.39(17) . . ?
N4 Ni1 O5 164.78(16) . . ?
N4 Ni1 O2 101.87(16) . . ?
N4 Ni1 O1 101.00(17) . . ?
N3 Ni1 O5 93.24(17) . . ?
N3 Ni1 O2 102.59(18) . . ?
N3 Ni1 O1 164.40(18) . . ?
N3 Ni1 O4 98.56(18) . . ?
N3 Ni1 N4 79.83(18) . . ?
O2A Ni1A O5A 99.43(16) . . ?
O2A Ni1A O1A 61.73(16) . . ?
O5A Ni1A O1A 90.52(16) . . ?
O4A Ni1A O2A 153.60(16) . . ?
O4A Ni1A O5A 62.27(15) . . ?
O4A Ni1A O1A 97.66(16) . . ?
N3A Ni1A O2A 103.91(17) . . ?
N3A Ni1A O5A 97.14(17) . . ?
N3A Ni1A O4A 97.51(17) . . ?
N3A Ni1A O1A 164.82(18) . . ?
N3A Ni1A N4A 80.01(18) . . ?
N4A Ni1A O2A 92.60(17) . . ?
N4A Ni1A O5A 167.97(17) . . ?
N4A Ni1A O4A 106.31(17) . . ?
N4A Ni1A O1A 95.05(17) . . ?
N2 O5 Ni1 90.3(3) . . ?
N1 O2 Ni1 90.9(3) . . ?
N1A O2A Ni1A 91.5(3) . . ?
N2A O5A Ni1A 91.1(3) . . ?
N2A O4A Ni1A 91.8(3) . . ?
N1A O1A Ni1A 90.6(3) . . ?
N1 O1 Ni1 90.3(3) . . ?
N2 O4 Ni1 91.6(3) . . ?
C12A N3A Ni1A 113.6(4) . . ?
C12A N3A C11A 119.4(5) . . ?
C11A N3A Ni1A 127.0(4) . . ?
C14A N4A Ni1A 114.6(4) . . ?
C14A N4A C16A 121.3(5) . . ?
C16A N4A Ni1A 123.2(4) . . ?
C16 N4 Ni1 126.8(4) . . ?
C14 N4 Ni1 112.9(4) . . ?
C14 N4 C16 120.3(5) . . ?
C12 N3 Ni1 115.8(4) . . ?
C12 N3 C11 119.9(5) . . ?
C11 N3 Ni1 124.2(4) . . ?
O1A N1A O2A 116.2(5) . . ?
O3A N1A O2A 120.8(5) . . ?
O3A N1A O1A 123.0(5) . . ?
O1 N1 O2 116.8(5) . . ?
O3 N1 O2 120.7(5) . . ?
O3 N1 O1 122.6(5) . . ?
O5 N2 O4 115.0(5) . . ?
O6 N2 O5 123.5(5) . . ?
O6 N2 O4 121.6(5) . . ?
O5A N2A O4A 114.9(5) . . ?
O6A N2A O5A 122.8(5) . . ?
O6A N2A O4A 122.3(5) . . ?
N3 C12 C14 114.5(5) . . ?
N3 C12 C13 125.9(5) . . ?
C13 C12 C14 119.6(5) . . ?
N3A C12A C14A 116.2(5) . . ?
N3A C12A C13A 124.4(5) . . ?
C14A C12A C13A 119.3(5) . . ?
N4A C14A C12A 115.3(5) . . ?
N4A C14A C15A 126.7(5) . . ?
C12A C14A C15A 117.9(5) . . ?
C4A C11A N3A 117.1(5) . . ?
C9A C11A N3A 120.7(5) . . ?
C9A C11A C4A 122.2(5) . . ?
C23 C16 N4 119.5(5) . . ?
C17 C16 N4 118.6(5) . . ?
C17 C16 C23 121.9(5) . . ?
N4 C14 C12 116.7(5) . . ?
N4 C14 C15 124.9(5) . . ?
C15 C14 C12 118.3(5) . . ?
C23A C16A N4A 121.2(5) . . ?
C23A C16A C17A 121.3(5) . . ?
C17A C16A N4A 117.5(5) . . ?
C11 C9 C10 123.2(5) . . ?
C11 C9 C8 116.7(5) . . ?
C8 C9 C10 120.1(5) . . ?
C11 C4 C5 117.6(5) . . ?
C11 C4 C3 122.5(5) . . ?
C5 C4 C3 119.9(5) . . ?
C16 C23 C22 117.5(6) . . ?
C16 C23 C24 121.5(5) . . ?
C22 C23 C24 121.0(5) . . ?
C9 C11 N3 117.2(5) . . ?
C4 C11 N3 119.7(5) . . ?
C4 C11 C9 123.0(5) . . ?
C17 C19 H19 119.0 . . ?
C17 C19 C20 122.0(6) . . ?
C20 C19 H19 119.0 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
C16A C23A C24A 122.6(5) . . ?
C16A C23A C22A 118.7(6) . . ?
C22A C23A C24A 118.7(6) . . ?
C16A C17A C18A 122.2(5) . . ?
C19A C17A C16A 117.2(6) . . ?
C19A C17A C18A 120.6(5) . . ?
C23 C22 H22 118.7 . . ?
C20 C22 C23 122.6(6) . . ?
C20 C22 H22 118.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C17 C19 118.0(6) . . ?
C16 C17 C18 122.0(5) . . ?
C19 C17 C18 120.0(6) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.0(6) . . ?
C6 C5 H5 119.0 . . ?
C23A C24A H24D 109.5 . . ?
C23A C24A H24E 109.5 . . ?
C23A C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
C11A C4A C3A 121.9(5) . . ?
C5A C4A C11A 117.3(6) . . ?
C5A C4A C3A 120.8(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C8 H8 118.6 . . ?
C6 C8 C9 122.7(6) . . ?
C6 C8 H8 118.6 . . ?
C4A C5A H5A 118.6 . . ?
C6A C5A C4A 122.7(6) . . ?
C6A C5A H5A 118.6 . . ?
C14A C15A H15D 109.5 . . ?
C14A C15A H15E 109.5 . . ?
C14A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C19 C20 C21 121.0(7) . . ?
C22 C20 C19 117.9(6) . . ?
C22 C20 C21 121.0(6) . . ?
C5A C6A C7A 121.9(6) . . ?
C8A C6A C5A 118.3(6) . . ?
C8A C6A C7A 119.8(6) . . ?
C6A C8A H8A 118.9 . . ?
C6A C8A C9A 122.3(6) . . ?
C9A C8A H8A 118.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11A C9A C8A 117.2(6) . . ?
C11A C9A C10A 122.6(6) . . ?
C8A C9A C10A 120.1(6) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4A C3A H3AA 109.5 . . ?
C4A C3A H3AB 109.5 . . ?
C4A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17A C19A H19A 118.5 . . ?
C20A C19A C17A 123.0(6) . . ?
C20A C19A H19A 118.5 . . ?
C5 C6 C7 121.1(6) . . ?
C8 C6 C5 118.0(5) . . ?
C8 C6 C7 121.0(6) . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C19A C20A C21A 121.1(6) . . ?
C22A C20A C19A 117.7(6) . . ?
C22A C20A C21A 121.2(6) . . ?
C23A C22A H22A 119.0 . . ?
C20A C22A C23A 122.0(6) . . ?
C20A C22A H22A 119.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C6A C7A H7AA 109.5 . . ?
C6A C7A H7AB 109.5 . . ?
C6A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C20A C21A H21D 109.5 . . ?
C20A C21A H21E 109.5 . . ?
C20A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
Cl1 C1 H1AA 110.2 . . ?
Cl1 C1 H1AB 110.2 . . ?
Cl2 C1 Cl1 107.4(5) . . ?
Cl2 C1 H1AA 110.2 . . ?
Cl2 C1 H1AB 110.2 . . ?
H1AA C1 H1AB 108.5 . . ?
H1BC C1 H1BD 108.2 . . ?
Cl2A C1 H1BC 109.7 . . ?
Cl2A C1 H1BD 109.7 . . ?
Cl1A C1 H1BC 109.7 . . ?
Cl1A C1 H1BD 109.7 . . ?
Cl1A C1 Cl2A 109.9(9) . . ?
Cl3 C2 Cl4 119(2) . . ?
Cl3 C2 H2A 107.5 . . ?
Cl3 C2 H2B 107.5 . . ?
Cl4 C2 H2A 107.5 . . ?
Cl4 C2 H2B 107.5 . . ?
H2A C2 H2B 107.0 . . ?

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
_geom_hbond_publ_flag
C15 H15A O3A 0.98 2.53 3.373(8) 144.4 4_575 yes
C15 H15C Cl3 0.98 2.83 3.644(12) 141.1 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O5 N2 O4 3.3(5) . . . . ?
Ni1 O5 N2 O6 -176.8(5) . . . . ?
Ni1 O2 N1 O1 4.4(5) . . . . ?
Ni1 O2 N1 O3 -174.8(5) . . . . ?
Ni1 O1 N1 O2 -4.4(5) . . . . ?
Ni1 O1 N1 O3 174.8(5) . . . . ?
Ni1 O4 N2 O5 -3.3(5) . . . . ?
Ni1 O4 N2 O6 176.7(5) . . . . ?
Ni1 N4 C16 C23 -87.1(6) . . . . ?
Ni1 N4 C16 C17 92.1(6) . . . . ?
Ni1 N4 C14 C12 -5.6(6) . . . . ?
Ni1 N4 C14 C15 178.1(4) . . . . ?
Ni1 N3 C12 C14 2.8(6) . . . . ?
Ni1 N3 C12 C13 -179.7(5) . . . . ?
Ni1 N3 C11 C9 -91.1(6) . . . . ?
Ni1 N3 C11 C4 84.4(6) . . . . ?
Ni1A O2A N1A O1A 1.4(5) . . . . ?
Ni1A O2A N1A O3A -177.5(5) . . . . ?
Ni1A O5A N2A O4A 1.6(5) . . . . ?
Ni1A O5A N2A O6A -179.6(5) . . . . ?
Ni1A O4A N2A O5A -1.6(5) . . . . ?
Ni1A O4A N2A O6A 179.5(5) . . . . ?
Ni1A O1A N1A O2A -1.3(5) . . . . ?
Ni1A O1A N1A O3A 177.5(5) . . . . ?
Ni1A N3A C12A C14A 3.0(6) . . . . ?
Ni1A N3A C12A C13A -178.8(5) . . . . ?
Ni1A N3A C11A C4A -87.5(6) . . . . ?
Ni1A N3A C11A C9A 89.5(6) . . . . ?
Ni1A N4A C14A C12A 4.7(6) . . . . ?
Ni1A N4A C14A C15A -174.6(5) . . . . ?
Ni1A N4A C16A C23A 101.5(6) . . . . ?
Ni1A N4A C16A C17A -76.1(6) . . . . ?
N3A C12A C14A N4A -5.3(7) . . . . ?
N3A C12A C14A C15A 174.1(5) . . . . ?
N3A C11A C4A C5A 178.9(5) . . . . ?
N3A C11A C4A C3A -3.3(9) . . . . ?
N3A C11A C9A C8A -177.5(6) . . . . ?
N3A C11A C9A C10A 4.1(10) . . . . ?
N4A C16A C23A C24A 0.1(9) . . . . ?
N4A C16A C23A C22A -177.9(5) . . . . ?
N4A C16A C17A C18A -1.8(8) . . . . ?
N4A C16A C17A C19A 177.9(5) . . . . ?
N4 C16 C23 C22 178.8(5) . . . . ?
N4 C16 C23 C24 -3.5(8) . . . . ?
N4 C16 C17 C19 -180.0(5) . . . . ?
N4 C16 C17 C18 -1.3(8) . . . . ?
N3 C12 C14 N4 2.1(7) . . . . ?
N3 C12 C14 C15 178.6(5) . . . . ?
C12 N3 C11 C9 85.0(7) . . . . ?
C12 N3 C11 C4 -99.5(7) . . . . ?
C12A N3A C11A C4A 89.5(6) . . . . ?
C12A N3A C11A C9A -93.5(7) . . . . ?
C14A N4A C16A C23A -67.4(7) . . . . ?
C14A N4A C16A C17A 115.0(6) . . . . ?
C11A N3A C12A C14A -174.3(5) . . . . ?
C11A N3A C12A C13A 3.8(9) . . . . ?
C11A C4A C5A C6A -2.1(10) . . . . ?
C16 N4 C14 C12 173.1(5) . . . . ?
C16 N4 C14 C15 -3.1(8) . . . . ?
C16 C23 C22 C20 1.8(9) . . . . ?
C14 N4 C16 C23 94.3(6) . . . . ?
C14 N4 C16 C17 -86.5(7) . . . . ?
C16A N4A C14A C12A 174.5(5) . . . . ?
C16A N4A C14A C15A -4.9(9) . . . . ?
C16A C23A C22A C20A 0.0(10) . . . . ?
C16A C17A C19A C20A 0.2(10) . . . . ?
C9 C8 C6 C5 1.7(11) . . . . ?
C9 C8 C6 C7 -178.0(7) . . . . ?
C4 C5 C6 C8 -2.7(10) . . . . ?
C4 C5 C6 C7 177.1(6) . . . . ?
C23 C16 C17 C19 -0.8(9) . . . . ?
C23 C16 C17 C18 177.8(6) . . . . ?
C23 C22 C20 C19 -2.0(10) . . . . ?
C23 C22 C20 C21 179.9(6) . . . . ?
C11 N3 C12 C14 -173.6(5) . . . . ?
C11 N3 C12 C13 3.9(9) . . . . ?
C11 C9 C8 C6 0.2(10) . . . . ?
C11 C4 C5 C6 1.6(9) . . . . ?
C18A C17A C19A C20A 179.9(7) . . . . ?
C23A C16A C17A C18A -179.4(6) . . . . ?
C23A C16A C17A C19A 0.3(9) . . . . ?
C17A C16A C23A C24A 177.7(6) . . . . ?
C17A C16A C23A C22A -0.4(9) . . . . ?
C17A C19A C20A C22A -0.6(11) . . . . ?
C17A C19A C20A C21A -179.5(7) . . . . ?
C17 C16 C23 C22 -0.3(9) . . . . ?
C17 C16 C23 C24 177.4(6) . . . . ?
C17 C19 C20 C22 0.8(10) . . . . ?
C17 C19 C20 C21 178.9(6) . . . . ?
C5 C4 C11 N3 -174.8(5) . . . . ?
C5 C4 C11 C9 0.5(9) . . . . ?
C24A C23A C22A C20A -178.1(7) . . . . ?
C4A C11A C9A C8A -0.6(10) . . . . ?
C4A C11A C9A C10A -179.0(6) . . . . ?
C4A C5A C6A C8A 1.1(11) . . . . ?
C4A C5A C6A C7A -178.9(7) . . . . ?
C10 C9 C11 N3 -8.0(9) . . . . ?
C10 C9 C11 C4 176.6(6) . . . . ?
C10 C9 C8 C6 -177.8(7) . . . . ?
C8 C9 C11 N3 174.0(6) . . . . ?
C8 C9 C11 C4 -1.4(9) . . . . ?
C5A C6A C8A C9A 0.2(11) . . . . ?
C20 C19 C17 C16 0.6(9) . . . . ?
C20 C19 C17 C18 -178.0(6) . . . . ?
C6A C8A C9A C11A -0.5(11) . . . . ?
C6A C8A C9A C10A 177.9(7) . . . . ?
C13 C12 C14 N4 -175.6(5) . . . . ?
C13 C12 C14 C15 0.9(8) . . . . ?
C9A C11A C4A C5A 1.9(9) . . . . ?
C9A C11A C4A C3A 179.7(6) . . . . ?
C24 C23 C22 C20 -175.9(6) . . . . ?
C3A C4A C5A C6A -179.9(7) . . . . ?
C19A C20A C22A C23A 0.5(11) . . . . ?
C13A C12A C14A N4A 176.5(5) . . . . ?
C13A C12A C14A C15A -4.1(8) . . . . ?
C3 C4 C11 N3 6.9(9) . . . . ?
C3 C4 C11 C9 -177.9(6) . . . . ?
C3 C4 C5 C6 180.0(6) . . . . ?
C7A C6A C8A C9A -179.7(7) . . . . ?
C21A C20A C22A C23A 179.4(7) . . . . ?

_olex2_date_sample_data_collection 2018-08-22
_olex2_date_sample_submission    2019-08-22
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20016
_database_code_depnum_ccdc_archive 'CCDC 2083110'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana University
United States of America
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 N3 Ni O'
_chemical_formula_weight         409.18

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                   8.631(6)
_cell_length_b                   9.896(6)
_cell_length_c                   12.698(8)
_cell_angle_alpha                67.393(17)
_cell_angle_beta                 84.22(2)
_cell_angle_gamma                78.271(17)
_cell_volume                     979.9(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1234
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      19.78

_exptl_crystal_description       needle
_exptl_crystal_colour            teal
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             434
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.021
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.004
_exptl_absorpt_coefficient_mu    1.007
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4112
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2018'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'0.50 degree frames measured for 5 and 9 seconds each'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            12098
_diffrn_reflns_av_unetI/netI     0.2827
_diffrn_reflns_av_R_equivalents  0.2083
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.266
_diffrn_reflns_theta_max         25.262
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3478
_reflns_number_gt                1648
_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       'BIS v6.2.9 (BrukerNano, 2018)'
_computing_cell_refinement       'SAINT V8.38A (BrukerNano, 2017)'
_computing_data_reduction        'SAINT V8.38A (BrukerNano, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 v2018.1-0 (BrukerNano, 2018)'
_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)+(0.1533P)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_number_reflns         3478
_refine_ls_number_parameters     253
_refine_ls_number_restraints     211
_refine_ls_R_factor_all          0.2105
_refine_ls_R_factor_gt           0.1238
_refine_ls_wR_factor_ref         0.3484
_refine_ls_wR_factor_gt          0.2828
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.941
_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
Ni1 Ni 0.34758(18) 0.54185(14) 0.50492(13) 0.0365(7) Uani 1 1 d . . . . .
O1 O 0.3664(9) 0.2565(7) 0.4986(7) 0.042(2) Uani 1 1 d . . . . .
N1 N 0.3107(10) 0.6348(9) 0.6164(8) 0.034(2) Uani 1 1 d . . . . .
N2 N 0.3115(10) 0.7455(9) 0.4035(8) 0.036(2) Uani 1 1 d . . . . .
N3 N 0.3480(11) 0.3775(9) 0.5014(7) 0.038(2) Uani 1 1 d . . . . .
C1 C 0.3036(13) 0.7814(11) 0.5702(10) 0.037(2) Uani 1 1 d . . . . .
C2 C 0.3015(13) 0.8435(11) 0.4522(10) 0.037(2) Uani 1 1 d . . . . .
C3 C 0.2797(14) 0.8730(12) 0.6456(10) 0.044(3) Uani 1 1 d . . . . .
H3A H 0.166153 0.904373 0.657135 0.065 Uiso 1 1 calc R U . . .
H3B H 0.329448 0.960944 0.608429 0.065 Uiso 1 1 calc R U . . .
H3C H 0.328080 0.812375 0.719536 0.065 Uiso 1 1 calc R U . . .
C4 C 0.2774(16) 1.0068(11) 0.3875(11) 0.049(3) Uani 1 1 d . . . . .
H4A H 0.277689 1.027274 0.305605 0.074 Uiso 1 1 calc R U . . .
H4B H 0.363087 1.047171 0.403560 0.074 Uiso 1 1 calc R U . . .
H4C H 0.175673 1.053741 0.410649 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2869(14) 0.5591(11) 0.7361(10) 0.035(2) Uani 1 1 d . . . . .
C6 C 0.4056(14) 0.5103(11) 0.8137(10) 0.039(2) Uani 1 1 d . . . . .
C7 C 0.3710(14) 0.4258(12) 0.9269(10) 0.039(2) Uani 1 1 d . . . . .
H7 H 0.450983 0.395221 0.981714 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2216(14) 0.3836(12) 0.9635(10) 0.042(2) Uani 1 1 d . . . . .
C9 C 0.1089(15) 0.4403(12) 0.8858(10) 0.040(2) Uani 1 1 d . . . . .
H9 H 0.005564 0.420218 0.910853 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1299(14) 0.5252(12) 0.7724(10) 0.039(2) Uani 1 1 d . . . . .
C11 C 0.5708(14) 0.5444(12) 0.7780(10) 0.041(3) Uani 1 1 d . . . . .
H11A H 0.612568 0.507555 0.717458 0.062 Uiso 1 1 calc R U . . .
H11B H 0.640005 0.495572 0.843761 0.062 Uiso 1 1 calc R U . . .
H11C H 0.566624 0.652231 0.749675 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1982(15) 0.2765(13) 1.0822(10) 0.046(3) Uani 1 1 d . . . . .
H12A H 0.092327 0.305887 1.111093 0.069 Uiso 1 1 calc R U . . .
H12B H 0.278128 0.277268 1.131440 0.069 Uiso 1 1 calc R U . . .
H12C H 0.208679 0.176253 1.081758 0.069 Uiso 1 1 calc R U . . .
C13 C 0.0031(15) 0.5826(12) 0.6916(10) 0.045(3) Uani 1 1 d . . . . .
H13A H -0.090034 0.538502 0.727433 0.068 Uiso 1 1 calc R U . . .
H13B H 0.037527 0.557029 0.624527 0.068 Uiso 1 1 calc R U . . .
H13C H -0.023798 0.690974 0.668035 0.068 Uiso 1 1 calc R U . . .
C14 C 0.2837(13) 0.7916(10) 0.2850(10) 0.032(2) Uani 1 1 d . . . . .
C15 C 0.1291(13) 0.7912(10) 0.2559(10) 0.034(2) Uani 1 1 d . . . . .
C16 C 0.1018(14) 0.8179(11) 0.1438(10) 0.040(2) Uani 1 1 d . . . . .
H16 H -0.001588 0.817581 0.124380 0.048 Uiso 1 1 calc R U . . .
C17 C 0.2168(14) 0.8449(11) 0.0586(10) 0.040(2) Uani 1 1 d . . . . .
C18 C 0.3669(14) 0.8541(10) 0.0871(10) 0.037(2) Uani 1 1 d . . . . .
H18 H 0.446226 0.879842 0.029072 0.045 Uiso 1 1 calc R U . . .
C19 C 0.3999(13) 0.8260(10) 0.1985(10) 0.033(2) Uani 1 1 d . . . . .
C20 C -0.0020(13) 0.7609(13) 0.3461(10) 0.043(3) Uani 1 1 d . . . . .
H20A H -0.100925 0.770027 0.310200 0.064 Uiso 1 1 calc R U . . .
H20B H -0.015534 0.833021 0.383245 0.064 Uiso 1 1 calc R U . . .
H20C H 0.025782 0.659980 0.403080 0.064 Uiso 1 1 calc R U . . .
C21 C 0.1930(15) 0.8538(12) -0.0604(10) 0.045(3) Uani 1 1 d . . . . .
H21A H 0.218126 0.753605 -0.062388 0.067 Uiso 1 1 calc R U . . .
H21B H 0.262939 0.916266 -0.114558 0.067 Uiso 1 1 calc R U . . .
H21C H 0.082626 0.897141 -0.081466 0.067 Uiso 1 1 calc R U . . .
C22 C 0.5624(13) 0.8298(11) 0.2250(10) 0.038(3) Uani 1 1 d . . . . .
H22A H 0.628794 0.850670 0.155229 0.057 Uiso 1 1 calc R U . . .
H22B H 0.607418 0.733304 0.281898 0.057 Uiso 1 1 calc R U . . .
H22C H 0.558168 0.907900 0.255226 0.057 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 N3 1.644(8) . ?
Ni1 N2 1.910(9) . ?
Ni1 N1 1.934(8) . ?
Ni1 Ni1 2.598(3) 2_666 ?
O1 N3 1.189(10) . ?
N1 C1 1.331(13) . ?
N1 C5 1.428(14) . ?
N2 C2 1.322(13) . ?
N2 C14 1.425(14) . ?
C1 C2 1.384(15) . ?
C1 C3 1.526(14) . ?
C2 C4 1.485(14) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.375(17) . ?
C5 C10 1.449(16) . ?
C6 C7 1.395(16) . ?
C6 C11 1.517(16) . ?
C7 C8 1.414(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.335(17) . ?
C8 C12 1.494(16) . ?
C9 C10 1.375(15) . ?
C9 H9 0.9500 . ?
C10 C13 1.448(17) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.399(14) . ?
C14 C15 1.420(16) . ?
C15 C16 1.380(16) . ?
C15 C20 1.515(14) . ?
C16 C17 1.377(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.409(17) . ?
C17 C21 1.512(16) . ?
C18 C19 1.380(16) . ?
C18 H18 0.9500 . ?
C19 C22 1.486(15) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Ni1 N2 138.4(4) . . ?
N3 Ni1 N1 137.7(4) . . ?
N2 Ni1 N1 81.0(4) . . ?
N3 Ni1 Ni1 82.3(3) . 2_666 ?
N2 Ni1 Ni1 104.2(3) . 2_666 ?
N1 Ni1 Ni1 105.5(3) . 2_666 ?
C1 N1 C5 121.6(8) . . ?
C1 N1 Ni1 113.2(7) . . ?
C5 N1 Ni1 125.2(6) . . ?
C2 N2 C14 121.3(9) . . ?
C2 N2 Ni1 115.3(8) . . ?
C14 N2 Ni1 123.2(6) . . ?
O1 N3 Ni1 172.6(9) . . ?
N1 C1 C2 115.5(9) . . ?
N1 C1 C3 120.5(10) . . ?
C2 C1 C3 123.6(9) . . ?
N2 C2 C1 114.0(9) . . ?
N2 C2 C4 123.3(11) . . ?
C1 C2 C4 122.5(9) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 123.5(10) . . ?
C6 C5 C10 120.4(11) . . ?
N1 C5 C10 115.9(10) . . ?
C5 C6 C7 118.1(11) . . ?
C5 C6 C11 121.4(11) . . ?
C7 C6 C11 120.4(12) . . ?
C6 C7 C8 122.7(12) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 116.4(11) . . ?
C9 C8 C12 123.4(11) . . ?
C7 C8 C12 120.1(12) . . ?
C8 C9 C10 125.4(12) . . ?
C8 C9 H9 117.3 . . ?
C10 C9 H9 117.3 . . ?
C9 C10 C13 123.0(11) . . ?
C9 C10 C5 116.7(11) . . ?
C13 C10 C5 120.3(11) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 119.0(11) . . ?
C19 C14 N2 124.4(10) . . ?
C15 C14 N2 116.4(9) . . ?
C16 C15 C14 118.4(10) . . ?
C16 C15 C20 120.9(10) . . ?
C14 C15 C20 120.7(10) . . ?
C17 C16 C15 123.3(12) . . ?
C17 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
C16 C17 C18 117.7(11) . . ?
C16 C17 C21 123.2(11) . . ?
C18 C17 C21 118.9(10) . . ?
C19 C18 C17 120.8(11) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 120.6(11) . . ?
C18 C19 C22 118.6(10) . . ?
C14 C19 C22 120.8(11) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C5 N1 C1 C2 -169.3(9) . . . . ?
Ni1 N1 C1 C2 8.6(12) . . . . ?
C5 N1 C1 C3 3.9(16) . . . . ?
Ni1 N1 C1 C3 -178.3(8) . . . . ?
C14 N2 C2 C1 169.0(9) . . . . ?
Ni1 N2 C2 C1 -6.0(12) . . . . ?
C14 N2 C2 C4 -6.5(17) . . . . ?
Ni1 N2 C2 C4 178.6(9) . . . . ?
N1 C1 C2 N2 -1.9(14) . . . . ?
C3 C1 C2 N2 -174.7(11) . . . . ?
N1 C1 C2 C4 173.7(11) . . . . ?
C3 C1 C2 C4 0.8(17) . . . . ?
C1 N1 C5 C6 -86.1(12) . . . . ?
Ni1 N1 C5 C6 96.4(11) . . . . ?
C1 N1 C5 C10 98.5(12) . . . . ?
Ni1 N1 C5 C10 -79.1(10) . . . . ?
N1 C5 C6 C7 -174.2(8) . . . . ?
C10 C5 C6 C7 1.1(13) . . . . ?
N1 C5 C6 C11 4.8(14) . . . . ?
C10 C5 C6 C11 -180.0(9) . . . . ?
C5 C6 C7 C8 2.7(14) . . . . ?
C11 C6 C7 C8 -176.3(9) . . . . ?
C6 C7 C8 C9 -5.9(15) . . . . ?
C6 C7 C8 C12 171.9(9) . . . . ?
C7 C8 C9 C10 5.5(16) . . . . ?
C12 C8 C9 C10 -172.1(9) . . . . ?
C8 C9 C10 C13 179.4(10) . . . . ?
C8 C9 C10 C5 -2.0(15) . . . . ?
C6 C5 C10 C9 -1.5(13) . . . . ?
N1 C5 C10 C9 174.1(8) . . . . ?
C6 C5 C10 C13 177.1(9) . . . . ?
N1 C5 C10 C13 -7.3(13) . . . . ?
C2 N2 C14 C19 88.1(12) . . . . ?
Ni1 N2 C14 C19 -97.3(10) . . . . ?
C2 N2 C14 C15 -96.6(11) . . . . ?
Ni1 N2 C14 C15 78.0(10) . . . . ?
C19 C14 C15 C16 3.1(13) . . . . ?
N2 C14 C15 C16 -172.5(8) . . . . ?
C19 C14 C15 C20 -177.4(9) . . . . ?
N2 C14 C15 C20 7.0(12) . . . . ?
C14 C15 C16 C17 0.0(14) . . . . ?
C20 C15 C16 C17 -179.5(9) . . . . ?
C15 C16 C17 C18 -3.8(15) . . . . ?
C15 C16 C17 C21 171.6(9) . . . . ?
C16 C17 C18 C19 4.6(14) . . . . ?
C21 C17 C18 C19 -171.0(9) . . . . ?
C17 C18 C19 C14 -1.6(14) . . . . ?
C17 C18 C19 C22 177.0(9) . . . . ?
C15 C14 C19 C18 -2.3(13) . . . . ?
N2 C14 C19 C18 172.9(9) . . . . ?
C15 C14 C19 C22 179.1(8) . . . . ?
N2 C14 C19 C22 -5.7(14) . . . . ?

_refine_diff_density_max         2.711
_refine_diff_density_min         -1.158
_refine_diff_density_rms         0.160



# start Validation Reply Form
_vrf_RINTA01_20016               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Poor data to only low resoluion from very small, partially decayed 
crystal.
;
_vrf_PLAT020_20016               
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.208 Report
RESPONSE: Poor data to only low resoluion from very small, partially decayed 
crystal.
;
# end Validation Reply Form







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

data_19123
_database_code_depnum_ccdc_archive 'CCDC 2083112'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana University
United States of America
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C16 H28 B2 N4 Ni2 O8), 2 (C4 H8 O)'
_chemical_formula_sum            'C24 H44 B2 N4 Ni2 O10'
_chemical_formula_weight         687.67

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'
B B 0.0013 0.0007 '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/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                   12.209(2)
_cell_length_b                   7.5518(13)
_cell_length_c                   17.864(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.243(5)
_cell_angle_gamma                90
_cell_volume                     1581.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3676
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      24.71

_exptl_crystal_description       needle
_exptl_crystal_colour            teal
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.247
_shelx_estimated_absorpt_T_min   0.691
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6282
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2018'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'0.50 degree frames measured for 17 seconds each'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            21147
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.363
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3630
_reflns_number_gt                2816
_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       'BIS v6.2.9 (BrukerNano, 2018)'
_computing_cell_refinement       'SAINT V8.38A (BrukerNano, 2017)'
_computing_data_reduction        'SAINT V8.38A (BrukerNano, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 v2018.1-0 (BrukerNano, 2018)'

_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)+(0.0502P)²+1.1965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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         3630
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Ni1 Ni 0.46004(3) 0.41580(5) 0.56532(2) 0.01824(12) Uani 1 1 d . . . . .
O1 O 0.3650(2) 0.4788(3) 0.68882(14) 0.0355(6) Uani 1 1 d . . . . .
O2 O 0.60278(17) 0.5016(3) 0.54469(11) 0.0200(4) Uani 1 1 d . . . . .
O3 O 0.80282(17) 0.5582(3) 0.56780(12) 0.0212(4) Uani 1 1 d . . . . .
O4 O 0.74062(16) 0.4222(3) 0.66418(11) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.4078(2) 0.4561(3) 0.63844(15) 0.0220(6) Uani 1 1 d . . . . .
N2 N 0.4845(2) 0.1672(3) 0.52830(13) 0.0178(5) Uani 1 1 d . . . . .
B1 B 0.7095(3) 0.4959(4) 0.58977(19) 0.0183(7) Uani 1 1 d . . . . .
C1 C 0.5870(2) 0.0881(4) 0.54728(16) 0.0188(6) Uani 1 1 d . . . . .
H1 H 0.650621 0.147951 0.580540 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3979(2) 0.0782(4) 0.48040(16) 0.0199(6) Uani 1 1 d . . . . .
H2 H 0.324275 0.130828 0.465132 0.024 Uiso 1 1 calc R U . . .
C3 C 0.9003(3) 0.5549(4) 0.63702(18) 0.0232(7) Uani 1 1 d . . . . .
C4 C 0.8648(2) 0.4115(4) 0.68925(17) 0.0207(6) Uani 1 1 d . . . . .
C5 C 0.9105(3) 0.7407(4) 0.6717(2) 0.0319(8) Uani 1 1 d . . . . .
H5A H 0.917252 0.826945 0.632171 0.048 Uiso 1 1 calc R U . . .
H5B H 0.978403 0.747336 0.716542 0.048 Uiso 1 1 calc R U . . .
H5C H 0.842523 0.767363 0.688499 0.048 Uiso 1 1 calc R U . . .
C6 C 1.0054(3) 0.5092(5) 0.6116(2) 0.0290(7) Uani 1 1 d . . . . .
H6A H 1.019711 0.603005 0.577644 0.043 Uiso 1 1 calc R U . . .
H6B H 0.993180 0.396655 0.583195 0.043 Uiso 1 1 calc R U . . .
H6C H 1.071347 0.498407 0.657671 0.043 Uiso 1 1 calc R U . . .
C7 C 0.9048(3) 0.4504(5) 0.77621(19) 0.0327(8) Uani 1 1 d . . . . .
H7A H 0.877473 0.357263 0.804721 0.049 Uiso 1 1 calc R U . . .
H7B H 0.874306 0.565026 0.786594 0.049 Uiso 1 1 calc R U . . .
H7C H 0.988332 0.454041 0.793353 0.049 Uiso 1 1 calc R U . . .
C8 C 0.8975(3) 0.2238(4) 0.67353(19) 0.0275(7) Uani 1 1 d . . . . .
H8A H 0.861156 0.139646 0.700865 0.041 Uiso 1 1 calc R U . . .
H8B H 0.980567 0.210445 0.692221 0.041 Uiso 1 1 calc R U . . .
H8C H 0.871926 0.200221 0.617370 0.041 Uiso 1 1 calc R U . . .
O1S O 0.1762(2) -0.0626(3) 0.52034(13) 0.0335(6) Uani 1 1 d . . . . .
C1S C 0.1502(3) 0.0881(5) 0.5613(2) 0.0350(8) Uani 1 1 d . . . . .
H1SA H 0.069137 0.086139 0.561321 0.042 Uiso 1 1 calc R U . . .
H1SB H 0.165157 0.199443 0.536638 0.042 Uiso 1 1 calc R U . . .
C2S C 0.2277(3) 0.0733(5) 0.6436(2) 0.0339(8) Uani 1 1 d . . . . .
H2SA H 0.193676 0.131381 0.681525 0.041 Uiso 1 1 calc R U . . .
H2SB H 0.303488 0.126081 0.648043 0.041 Uiso 1 1 calc R U . . .
C3S C 0.2360(3) -0.1259(4) 0.6558(2) 0.0316(8) Uani 1 1 d . . . . .
H3SA H 0.306305 -0.159165 0.696559 0.038 Uiso 1 1 calc R U . . .
H3SB H 0.168826 -0.172930 0.670138 0.038 Uiso 1 1 calc R U . . .
C4S C 0.2388(3) -0.1906(4) 0.57604(19) 0.0278(7) Uani 1 1 d . . . . .
H4SA H 0.318551 -0.199148 0.573322 0.033 Uiso 1 1 calc R U . . .
H4SB H 0.202908 -0.308833 0.565200 0.033 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 N1 1.634(3) . ?
Ni1 O2 1.988(2) . ?
Ni1 O2 1.999(2) 3_666 ?
Ni1 N2 2.040(2) . ?
O1 N1 1.173(3) . ?
O2 B1 1.327(4) . ?
O3 B1 1.387(4) . ?
O3 C3 1.457(4) . ?
O4 B1 1.392(4) . ?
O4 C4 1.458(3) . ?
N2 C2 1.340(4) . ?
N2 C1 1.341(4) . ?
C1 C2 1.381(4) 3_656 ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C6 1.515(4) . ?
C3 C5 1.525(4) . ?
C3 C4 1.568(4) . ?
C4 C8 1.520(4) . ?
C4 C7 1.521(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O1S C1S 1.436(4) . ?
O1S C4S 1.443(4) . ?
C1S C2S 1.514(5) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C2S C3S 1.520(5) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S C4S 1.517(4) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?

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
N1 Ni1 O2 130.20(11) . . ?
N1 Ni1 O2 126.84(11) . 3_666 ?
O2 Ni1 O2 80.29(9) . 3_666 ?
N1 Ni1 N2 123.76(11) . . ?
O2 Ni1 N2 91.40(9) . . ?
O2 Ni1 N2 91.10(9) 3_666 . ?
B1 O2 Ni1 129.77(19) . . ?
B1 O2 Ni1 130.42(19) . 3_666 ?
Ni1 O2 Ni1 99.71(9) . 3_666 ?
B1 O3 C3 107.1(2) . . ?
B1 O4 C4 107.3(2) . . ?
O1 N1 Ni1 176.1(2) . . ?
C2 N2 C1 116.9(2) . . ?
C2 N2 Ni1 120.47(19) . . ?
C1 N2 Ni1 122.6(2) . . ?
O2 B1 O3 124.2(3) . . ?
O2 B1 O4 123.5(3) . . ?
O3 B1 O4 112.3(3) . . ?
N2 C1 C2 121.5(3) . 3_656 ?
N2 C1 H1 119.2 . . ?
C2 C1 H1 119.2 3_656 . ?
N2 C2 C1 121.6(3) . 3_656 ?
N2 C2 H2 119.2 . . ?
C1 C2 H2 119.2 3_656 . ?
O3 C3 C6 108.0(2) . . ?
O3 C3 C5 106.4(2) . . ?
C6 C3 C5 110.5(3) . . ?
O3 C3 C4 102.8(2) . . ?
C6 C3 C4 114.8(3) . . ?
C5 C3 C4 113.5(3) . . ?
O4 C4 C8 107.4(2) . . ?
O4 C4 C7 108.2(2) . . ?
C8 C4 C7 110.0(3) . . ?
O4 C4 C3 102.5(2) . . ?
C8 C4 C3 113.8(2) . . ?
C7 C4 C3 114.3(3) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1S O1S C4S 109.2(2) . . ?
O1S C1S C2S 105.7(3) . . ?
O1S C1S H1SA 110.6 . . ?
C2S C1S H1SA 110.6 . . ?
O1S C1S H1SB 110.6 . . ?
C2S C1S H1SB 110.6 . . ?
H1SA C1S H1SB 108.7 . . ?
C1S C2S C3S 102.1(3) . . ?
C1S C2S H2SA 111.3 . . ?
C3S C2S H2SA 111.3 . . ?
C1S C2S H2SB 111.3 . . ?
C3S C2S H2SB 111.3 . . ?
H2SA C2S H2SB 109.2 . . ?
C4S C3S C2S 101.6(3) . . ?
C4S C3S H3SA 111.4 . . ?
C2S C3S H3SA 111.4 . . ?
C4S C3S H3SB 111.4 . . ?
C2S C3S H3SB 111.4 . . ?
H3SA C3S H3SB 109.3 . . ?
O1S C4S C3S 106.6(3) . . ?
O1S C4S H4SA 110.4 . . ?
C3S C4S H4SA 110.4 . . ?
O1S C4S H4SB 110.4 . . ?
C3S C4S H4SB 110.4 . . ?
H4SA C4S H4SB 108.6 . . ?

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
Ni1 O2 B1 O3 178.80(19) . . . . ?
Ni1 O2 B1 O3 3.2(4) 3_666 . . . ?
Ni1 O2 B1 O4 0.4(4) . . . . ?
Ni1 O2 B1 O4 -175.21(19) 3_666 . . . ?
C3 O3 B1 O2 170.8(3) . . . . ?
C3 O3 B1 O4 -10.6(3) . . . . ?
C4 O4 B1 O2 170.0(3) . . . . ?
C4 O4 B1 O3 -8.6(3) . . . . ?
C2 N2 C1 C2 -0.9(4) . . . 3_656 ?
Ni1 N2 C1 C2 -178.0(2) . . . 3_656 ?
C1 N2 C2 C1 0.9(4) . . . 3_656 ?
Ni1 N2 C2 C1 178.1(2) . . . 3_656 ?
B1 O3 C3 C6 145.4(3) . . . . ?
B1 O3 C3 C5 -95.9(3) . . . . ?
B1 O3 C3 C4 23.6(3) . . . . ?
B1 O4 C4 C8 -97.8(3) . . . . ?
B1 O4 C4 C7 143.5(3) . . . . ?
B1 O4 C4 C3 22.4(3) . . . . ?
O3 C3 C4 O4 -27.9(3) . . . . ?
C6 C3 C4 O4 -144.9(3) . . . . ?
C5 C3 C4 O4 86.6(3) . . . . ?
O3 C3 C4 C8 87.8(3) . . . . ?
C6 C3 C4 C8 -29.2(4) . . . . ?
C5 C3 C4 C8 -157.7(3) . . . . ?
O3 C3 C4 C7 -144.7(2) . . . . ?
C6 C3 C4 C7 98.3(3) . . . . ?
C5 C3 C4 C7 -30.2(4) . . . . ?
C4S O1S C1S C2S 15.9(4) . . . . ?
O1S C1S C2S C3S -33.6(3) . . . . ?
C1S C2S C3S C4S 37.5(3) . . . . ?
C1S O1S C4S C3S 8.6(3) . . . . ?
C2S C3S C4S O1S -29.1(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
_geom_hbond_publ_flag
C1 H1 O4 0.95 2.61 3.472(4) 151.1 . yes
C8 H8C O1S 0.98 2.58 3.541(4) 166.1 3_656 yes

_refine_diff_density_max         1.351
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.088



####################################################################### 
# 
# 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_19181
_database_code_depnum_ccdc_archive 'CCDC 2083113'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana University
United States of America
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H16 B N2 Ni O4'
_chemical_formula_sum            'C11 H16 B N2 Ni O4'
_chemical_formula_weight         309.78

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'
B B 0.0013 0.0007 '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                   10.2092(5)
_cell_length_b                   11.9426(6)
_cell_length_c                   11.9808(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.560(2)
_cell_angle_gamma                90
_cell_volume                     1460.21(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9722
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.64

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.337
_shelx_estimated_absorpt_T_min   0.748
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2018'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'0.50 degree frames measured for 1.5 seconds each'
_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            48522
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.408
_diffrn_reflns_theta_max         30.060
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4277
_reflns_number_gt                3269
_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       'BIS v6.2.9 (BrukerNano, 2018)'
_computing_cell_refinement       'SAINT V8.38A (BrukerNano, 2017)'
_computing_data_reduction        'SAINT V8.38A (BrukerNano, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 v2018.1-0 (BrukerNano, 2018)'
_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)+(0.0334P)²+2.0731P] 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         4277
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.91599(3) 0.55125(2) 0.40307(2) 0.01551(8) Uani 1 1 d . . . . .
O1 O 0.89727(15) 0.49313(12) 0.55801(13) 0.0179(3) Uani 1 1 d . . . . .
O2 O 0.80091(15) 0.39412(14) 0.70867(13) 0.0211(3) Uani 1 1 d . . . . .
O3 O 0.67034(15) 0.43687(13) 0.55500(13) 0.0190(3) Uani 1 1 d . . . . .
O4 O 0.77342(19) 0.56842(18) 0.20436(16) 0.0370(5) Uani 1 1 d . . . . .
N1 N 0.93641(18) 0.71305(14) 0.43978(16) 0.0171(4) Uani 1 1 d . . . . .
N2 N 0.83098(19) 0.53829(15) 0.28579(16) 0.0203(4) Uani 1 1 d . . . . .
B1 B 0.7948(2) 0.44453(19) 0.6037(2) 0.0166(4) Uani 1 1 d . . . . .
C1 C 0.9053(2) 0.79397(18) 0.3661(2) 0.0217(5) Uani 1 1 d . . . . .
H1 H 0.865662 0.772908 0.296536 0.026 Uiso 1 1 calc R U . . .
C2 C 0.9279(2) 0.90678(18) 0.38613(19) 0.0216(5) Uani 1 1 d . . . . .
H2 H 0.903777 0.961074 0.331382 0.026 Uiso 1 1 calc R U . . .
C3 C 0.9865(2) 0.93986(16) 0.48753(18) 0.0164(4) Uani 1 1 d . . . . .
C4 C 1.0177(2) 0.85568(17) 0.56409(19) 0.0190(4) Uani 1 1 d . . . . .
H4 H 1.056817 0.874020 0.634585 0.023 Uiso 1 1 calc R U . . .
C5 C 0.9915(2) 0.74548(18) 0.53712(19) 0.0192(4) Uani 1 1 d . . . . .
H5 H 1.013821 0.689491 0.590657 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6797(2) 0.3315(2) 0.7190(2) 0.0226(5) Uani 1 1 d . . . . .
C7 C 0.5839(2) 0.39891(19) 0.64177(19) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.6422(3) 0.3264(3) 0.8401(2) 0.0382(7) Uani 1 1 d . . . . .
H8A H 0.703036 0.276918 0.881212 0.057 Uiso 1 1 calc R U . . .
H8B H 0.552850 0.297188 0.845049 0.057 Uiso 1 1 calc R U . . .
H8C H 0.646450 0.401670 0.872486 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7063(3) 0.2140(2) 0.6755(3) 0.0319(6) Uani 1 1 d . . . . .
H9A H 0.723735 0.217551 0.595535 0.048 Uiso 1 1 calc R U . . .
H9B H 0.629627 0.166505 0.687304 0.048 Uiso 1 1 calc R U . . .
H9C H 0.782592 0.182378 0.715641 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5301(3) 0.5030(2) 0.6982(2) 0.0316(6) Uani 1 1 d . . . . .
H10A H 0.602811 0.546754 0.730776 0.047 Uiso 1 1 calc R U . . .
H10B H 0.471021 0.480494 0.757339 0.047 Uiso 1 1 calc R U . . .
H10C H 0.481902 0.548607 0.642933 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4729(2) 0.3304(2) 0.5903(2) 0.0272(5) Uani 1 1 d . . . . .
H11A H 0.415662 0.379140 0.544864 0.041 Uiso 1 1 calc R U . . .
H11B H 0.422324 0.296145 0.649735 0.041 Uiso 1 1 calc R U . . .
H11C H 0.509012 0.271538 0.543174 0.041 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 N2 1.6386(19) . ?
Ni1 N1 1.9914(17) . ?
Ni1 O1 1.9960(16) . ?
Ni1 O1 2.0210(15) 3_766 ?
O1 B1 1.328(3) . ?
O2 B1 1.394(3) . ?
O2 C6 1.454(3) . ?
O3 B1 1.387(3) . ?
O3 C7 1.454(3) . ?
O4 N2 1.181(3) . ?
N1 C5 1.338(3) . ?
N1 C1 1.342(3) . ?
C1 C2 1.387(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 C3 1.491(4) 3_776 ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C8 1.512(3) . ?
C6 C9 1.524(4) . ?
C6 C7 1.553(3) . ?
C7 C11 1.515(3) . ?
C7 C10 1.525(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
N2 Ni1 N1 109.32(8) . . ?
N2 Ni1 O1 134.65(8) . . ?
N1 Ni1 O1 98.28(7) . . ?
N2 Ni1 O1 130.34(8) . 3_766 ?
N1 Ni1 O1 96.38(7) . 3_766 ?
O1 Ni1 O1 78.92(7) . 3_766 ?
B1 O1 Ni1 129.22(15) . . ?
B1 O1 Ni1 122.63(14) . 3_766 ?
Ni1 O1 Ni1 101.08(7) . 3_766 ?
B1 O2 C6 106.36(17) . . ?
B1 O3 C7 106.64(17) . . ?
C5 N1 C1 116.85(19) . . ?
C5 N1 Ni1 120.82(15) . . ?
C1 N1 Ni1 122.15(15) . . ?
O4 N2 Ni1 156.83(18) . . ?
O1 B1 O3 125.3(2) . . ?
O1 B1 O2 123.0(2) . . ?
O3 B1 O2 111.68(19) . . ?
N1 C1 C2 123.4(2) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 116.98(19) . . ?
C4 C3 C3 121.7(2) . 3_776 ?
C2 C3 C3 121.3(2) . 3_776 ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 123.7(2) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
O2 C6 C8 109.9(2) . . ?
O2 C6 C9 106.55(19) . . ?
C8 C6 C9 110.1(2) . . ?
O2 C6 C7 101.91(17) . . ?
C8 C6 C7 114.9(2) . . ?
C9 C6 C7 112.9(2) . . ?
O3 C7 C11 109.84(19) . . ?
O3 C7 C10 107.22(19) . . ?
C11 C7 C10 110.3(2) . . ?
O3 C7 C6 101.69(17) . . ?
C11 C7 C6 114.48(19) . . ?
C10 C7 C6 112.8(2) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N1 Ni1 N2 O4 3.2(5) . . . . ?
O1 Ni1 N2 O4 127.4(5) . . . . ?
O1 Ni1 N2 O4 -113.6(5) 3_766 . . . ?
Ni1 O1 B1 O3 -8.9(3) . . . . ?
Ni1 O1 B1 O3 -153.66(17) 3_766 . . . ?
Ni1 O1 B1 O2 170.98(15) . . . . ?
Ni1 O1 B1 O2 26.2(3) 3_766 . . . ?
C7 O3 B1 O1 -168.5(2) . . . . ?
C7 O3 B1 O2 11.6(2) . . . . ?
C6 O2 B1 O1 -168.5(2) . . . . ?
C6 O2 B1 O3 11.4(2) . . . . ?
C5 N1 C1 C2 0.3(4) . . . . ?
Ni1 N1 C1 C2 -174.80(19) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C3 179.7(3) . . . 3_776 ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C3 C4 C5 -179.7(3) 3_776 . . . ?
C1 N1 C5 C4 -0.4(3) . . . . ?
Ni1 N1 C5 C4 174.81(18) . . . . ?
C3 C4 C5 N1 -0.1(4) . . . . ?
B1 O2 C6 C8 -149.9(2) . . . . ?
B1 O2 C6 C9 90.8(2) . . . . ?
B1 O2 C6 C7 -27.7(2) . . . . ?
B1 O3 C7 C11 -149.44(19) . . . . ?
B1 O3 C7 C10 90.7(2) . . . . ?
B1 O3 C7 C6 -27.8(2) . . . . ?
O2 C6 C7 O3 33.7(2) . . . . ?
C8 C6 C7 O3 152.5(2) . . . . ?
C9 C6 C7 O3 -80.2(2) . . . . ?
O2 C6 C7 C11 152.0(2) . . . . ?
C8 C6 C7 C11 -89.2(3) . . . . ?
C9 C6 C7 C11 38.1(3) . . . . ?
O2 C6 C7 C10 -80.8(2) . . . . ?
C8 C6 C7 C10 38.0(3) . . . . ?
C9 C6 C7 C10 165.3(2) . . . . ?

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
_geom_hbond_publ_flag
C2 H2 O2 0.95 2.48 3.421(3) 168.9 4_575 yes
C4 H4 O2 0.95 2.35 3.283(3) 165.4 2_756 yes
C5 H5 O1 0.95 2.65 3.176(3) 115.1 . yes
C10 H10B O4 0.98 2.62 3.448(3) 142.8 3_666 yes
C11 H11A O3 0.98 2.64 3.572(3) 158.8 3_666 yes

_refine_diff_density_max         0.650
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.095



####################################################################### 
# 
# 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_mo_21006_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2083109'
loop_
_audit_author_name
_audit_author_address
'Veronica Carta'
;Indiana University
United States of America
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
dbeagan@iu.edu
vcarta@iu.edu
caulton@indiana.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22.967 H28 Cl0.033 F2.9 N3 Ni O3.9 S0.967'
_chemical_formula_sum            'C22.97 H28 Cl0.03 F2.90 N3 Ni O3.90 S0.97'
_chemical_formula_weight         554.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.4858(3)
_cell_length_b                   19.4001(6)
_cell_length_c                   12.4864(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.9590(10)
_cell_angle_gamma                90
_cell_volume                     2631.35(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    133.0
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1153
_exptl_crystal_preparation       synthesized
_exptl_crystal_recrystallization_method 'vapor diffusion of pentane into THF'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            92275
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.019
_diffrn_ambient_temperature      133.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker VENTURE D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4579
_reflns_number_total             6025
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+2.8604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(O2)
3. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(S1)=Sof(O2)=Sof(O3)=Sof(F2)=Sof(O4)=Sof(F3)=Sof(F1)=Sof(C23)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C17(H17), C6(H6), C20(H20)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C16(H16A,H16B,
 H16C), C5(H5A,H5B,H5C), C22(H22A,H22B,H22C), C1(H1A,H1B,H1C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.62785(3) 0.72007(2) 0.44236(3) 0.02274(10) Uani 1 1 d . . . . .
S1 S 0.74864(7) 0.62981(4) 0.66191(6) 0.02645(18) Uani 0.9667(15) 1 d . . P A 1
O2 O 0.65496(19) 0.63717(11) 0.55067(18) 0.0327(5) Uani 0.9667(15) 1 d . . P A
1
O3 O 0.83657(19) 0.68459(11) 0.69009(18) 0.0368(5) Uani 0.9667(15) 1 d . . P A
1
F2 F 0.9302(2) 0.54243(12) 0.73249(18) 0.0663(7) Uani 0.9667(15) 1 d . . P A 1
N3 N 0.51740(19) 0.66871(11) 0.30980(18) 0.0214(5) Uani 1 1 d . . . . .
N2 N 0.4647(2) 0.74032(11) 0.46266(18) 0.0217(5) Uani 1 1 d . . . . .
O4 O 0.7010(2) 0.60828(12) 0.7491(2) 0.0415(6) Uani 0.9667(15) 1 d . . P A 1
F3 F 0.7633(3) 0.49882(11) 0.6189(2) 0.0673(7) Uani 0.9667(15) 1 d . . P A 1
O1 O 0.8031(2) 0.81691(13) 0.4302(2) 0.0526(7) Uani 1 1 d . . . . .
F1 F 0.8754(3) 0.56335(14) 0.5558(2) 0.0733(8) Uani 0.9667(15) 1 d . . P A 1
N1 N 0.7352(2) 0.77450(13) 0.4404(2) 0.0295(5) Uani 1 1 d . . . . .
C7 C 0.4706(2) 0.84752(14) 0.5666(2) 0.0240(6) Uani 1 1 d . . . . .
C12 C 0.4018(2) 0.67398(13) 0.2962(2) 0.0222(5) Uani 1 1 d . . . . .
C10 C 0.3714(2) 0.71523(13) 0.3846(2) 0.0223(5) Uani 1 1 d . . . . .
C9 C 0.4510(2) 0.77625(14) 0.5586(2) 0.0229(5) Uani 1 1 d . . . . .
C14 C 0.5599(2) 0.62798(14) 0.2330(2) 0.0229(5) Uani 1 1 d . . . . .
C15 C 0.5892(2) 0.66137(14) 0.1460(2) 0.0257(6) Uani 1 1 d . . . . .
C21 C 0.5740(3) 0.55703(15) 0.2503(2) 0.0288(6) Uani 1 1 d . . . . .
C2 C 0.4247(3) 0.73918(14) 0.6441(2) 0.0275(6) Uani 1 1 d . . . . .
C8 C 0.4971(3) 0.88731(15) 0.4740(2) 0.0302(6) Uani 1 1 d . . . . .
H8A H 0.581803 0.878208 0.476176 0.045 Uiso 1 1 calc R U . . .
H8B H 0.487030 0.936710 0.484826 0.045 Uiso 1 1 calc R U . . .
H8C H 0.439845 0.872984 0.400451 0.045 Uiso 1 1 calc R U . . .
C13 C 0.3006(2) 0.64181(15) 0.2031(2) 0.0287(6) Uani 1 1 d . . . . .
H13A H 0.334916 0.619574 0.149475 0.043 Uiso 1 1 calc R U . . .
H13B H 0.241663 0.677388 0.163752 0.043 Uiso 1 1 calc R U . . .
H13C H 0.258706 0.607267 0.234704 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4187(2) 0.77596(16) 0.7383(2) 0.0307(6) Uani 1 1 d . . . . .
H3 H 0.402312 0.751561 0.797814 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6319(3) 0.62095(15) 0.0747(2) 0.0296(6) Uani 1 1 d . . . . .
H17 H 0.650803 0.642537 0.014102 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4622(2) 0.88105(15) 0.6619(2) 0.0288(6) Uani 1 1 d . . . . .
H6 H 0.475077 0.929463 0.668117 0.035 Uiso 1 1 calc R U . . .
C18 C 0.6478(3) 0.55028(16) 0.0888(3) 0.0327(7) Uani 1 1 d . . . . .
C11 C 0.2400(2) 0.72336(16) 0.3778(3) 0.0325(6) Uani 1 1 d . . . . .
H11A H 0.203519 0.677812 0.378859 0.049 Uiso 1 1 calc R U . . .
H11B H 0.194751 0.747195 0.307336 0.049 Uiso 1 1 calc R U . . .
H11C H 0.235487 0.750400 0.442578 0.049 Uiso 1 1 calc R U . . .
C20 C 0.6197(3) 0.51965(16) 0.1773(3) 0.0335(7) Uani 1 1 d . . . . .
H20 H 0.631905 0.471424 0.188812 0.040 Uiso 1 1 calc R U . . .
C4 C 0.4358(2) 0.84657(16) 0.7484(2) 0.0308(6) Uani 1 1 d . . . . .
C16 C 0.5757(3) 0.73835(15) 0.1297(3) 0.0322(7) Uani 1 1 d . . . . .
H16A H 0.493581 0.752421 0.129382 0.048 Uiso 1 1 calc R U . . .
H16B H 0.586282 0.750990 0.057499 0.048 Uiso 1 1 calc R U . . .
H16C H 0.638310 0.761662 0.191803 0.048 Uiso 1 1 calc R U . . .
C5 C 0.4243(3) 0.88440(19) 0.8497(3) 0.0444(8) Uani 1 1 d . . . . .
H5A H 0.343827 0.907089 0.829322 0.067 Uiso 1 1 calc R U . . .
H5B H 0.489560 0.919136 0.874486 0.067 Uiso 1 1 calc R U . . .
H5C H 0.432104 0.851623 0.911400 0.067 Uiso 1 1 calc R U . . .
C22 C 0.5397(3) 0.52068(16) 0.3429(3) 0.0395(8) Uani 1 1 d . . . . .
H22A H 0.543192 0.553444 0.403553 0.059 Uiso 1 1 calc R U . . .
H22B H 0.597656 0.482886 0.373313 0.059 Uiso 1 1 calc R U . . .
H22C H 0.456115 0.502116 0.311739 0.059 Uiso 1 1 calc R U . . .
C1 C 0.4029(3) 0.66249(15) 0.6385(3) 0.0356(7) Uani 1 1 d . . . . .
H1A H 0.315430 0.653175 0.599609 0.053 Uiso 1 1 calc R U . . .
H1B H 0.426931 0.643619 0.715374 0.053 Uiso 1 1 calc R U . . .
H1C H 0.452125 0.640801 0.596702 0.053 Uiso 1 1 calc R U . . .
C19 C 0.6962(3) 0.50805(18) 0.0105(3) 0.0446(8) Uani 1 1 d . . . . .
H19A H 0.697446 0.536440 -0.053995 0.067 Uiso 1 1 calc R U . . .
H19B H 0.642665 0.468060 -0.016816 0.067 Uiso 1 1 calc R U . . .
H19C H 0.779872 0.492299 0.051762 0.067 Uiso 1 1 calc R U . . .
C23 C 0.8339(3) 0.55488(18) 0.6410(3) 0.0404(8) Uani 0.9667(15) 1 d . . P A 1
Cl1 Cl 0.738(2) 0.6691(11) 0.5980(19) 0.0327(5) Uani 0.0333(15) 1 d . . P A 2


_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 O2 2.059(2) . ?
Ni1 N3 1.994(2) . ?
Ni1 N2 2.010(2) . ?
Ni1 N1 1.630(2) . ?
Ni1 Cl1 2.18(2) . ?
S1 O2 1.462(2) . ?
S1 O3 1.429(2) . ?
S1 O4 1.430(2) . ?
S1 C23 1.819(3) . ?
F2 C23 1.328(4) . ?
N3 C12 1.287(3) . ?
N3 C14 1.445(3) . ?
N2 C10 1.287(3) . ?
N2 C9 1.438(3) . ?
F3 C23 1.331(4) . ?
O1 N1 1.169(3) . ?
F1 C23 1.310(4) . ?
C7 C9 1.399(4) . ?
C7 C8 1.502(4) . ?
C7 C6 1.387(4) . ?
C12 C10 1.494(4) . ?
C12 C13 1.488(4) . ?
C10 C11 1.492(4) . ?
C9 C2 1.400(4) . ?
C14 C15 1.396(4) . ?
C14 C21 1.395(4) . ?
C15 C17 1.389(4) . ?
C15 C16 1.508(4) . ?
C21 C20 1.394(4) . ?
C21 C22 1.511(4) . ?
C2 C3 1.396(4) . ?
C2 C1 1.506(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.384(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(4) . ?
C6 H6 0.9500 . ?
C6 C4 1.385(4) . ?
C18 C20 1.383(4) . ?
C18 C19 1.512(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C20 H20 0.9500 . ?
C4 C5 1.505(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Ni1 O2 94.28(8) . . ?
N3 Ni1 N2 80.48(9) . . ?
N3 Ni1 Cl1 122.8(6) . . ?
N2 Ni1 O2 91.04(9) . . ?
N2 Ni1 Cl1 105.7(6) . . ?
N1 Ni1 O2 124.22(11) . . ?
N1 Ni1 N3 126.27(10) . . ?
N1 Ni1 N2 128.04(10) . . ?
N1 Ni1 Cl1 94.8(6) . . ?
O2 S1 C23 101.90(14) . . ?
O3 S1 O2 113.86(13) . . ?
O3 S1 O4 116.37(14) . . ?
O3 S1 C23 105.01(16) . . ?
O4 S1 O2 113.99(14) . . ?
O4 S1 C23 103.46(15) . . ?
S1 O2 Ni1 127.45(13) . . ?
C12 N3 Ni1 114.88(18) . . ?
C12 N3 C14 120.8(2) . . ?
C14 N3 Ni1 124.28(16) . . ?
C10 N2 Ni1 114.29(18) . . ?
C10 N2 C9 121.7(2) . . ?
C9 N2 Ni1 123.94(17) . . ?
O1 N1 Ni1 173.1(3) . . ?
C9 C7 C8 121.4(2) . . ?
C6 C7 C9 118.1(3) . . ?
C6 C7 C8 120.5(3) . . ?
N3 C12 C10 115.1(2) . . ?
N3 C12 C13 125.5(2) . . ?
C13 C12 C10 119.5(2) . . ?
N2 C10 C12 115.2(2) . . ?
N2 C10 C11 125.5(2) . . ?
C11 C10 C12 119.3(2) . . ?
C7 C9 N2 118.7(2) . . ?
C7 C9 C2 121.5(2) . . ?
C2 C9 N2 119.7(2) . . ?
C15 C14 N3 118.8(2) . . ?
C21 C14 N3 118.9(2) . . ?
C21 C14 C15 122.3(3) . . ?
C14 C15 C16 121.6(2) . . ?
C17 C15 C14 117.4(3) . . ?
C17 C15 C16 121.0(3) . . ?
C14 C21 C22 122.3(3) . . ?
C20 C21 C14 117.4(3) . . ?
C20 C21 C22 120.3(3) . . ?
C9 C2 C1 123.0(3) . . ?
C3 C2 C9 117.5(3) . . ?
C3 C2 C1 119.4(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.6(3) . . ?
C4 C3 H3 118.7 . . ?
C15 C17 H17 118.8 . . ?
C18 C17 C15 122.4(3) . . ?
C18 C17 H17 118.8 . . ?
C7 C6 H6 118.8 . . ?
C4 C6 C7 122.4(3) . . ?
C4 C6 H6 118.8 . . ?
C17 C18 C19 121.0(3) . . ?
C20 C18 C17 118.0(3) . . ?
C20 C18 C19 120.9(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C20 H20 118.8 . . ?
C18 C20 C21 122.3(3) . . ?
C18 C20 H20 118.8 . . ?
C3 C4 C6 117.9(3) . . ?
C3 C4 C5 120.7(3) . . ?
C6 C4 C5 121.4(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F2 C23 S1 111.0(2) . . ?
F2 C23 F3 108.1(3) . . ?
F3 C23 S1 111.2(3) . . ?
F1 C23 S1 111.8(2) . . ?
F1 C23 F2 107.5(3) . . ?
F1 C23 F3 107.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 N3 C12 C10 -2.3(3) . . . . ?
Ni1 N3 C12 C13 178.9(2) . . . . ?
Ni1 N3 C14 C15 -81.5(3) . . . . ?
Ni1 N3 C14 C21 96.5(3) . . . . ?
Ni1 N2 C10 C12 2.0(3) . . . . ?
Ni1 N2 C10 C11 -179.0(2) . . . . ?
Ni1 N2 C9 C7 74.0(3) . . . . ?
Ni1 N2 C9 C2 -102.9(3) . . . . ?
O2 S1 C23 F2 175.8(2) . . . . ?
O2 S1 C23 F3 -63.8(2) . . . . ?
O2 S1 C23 F1 55.8(3) . . . . ?
O3 S1 O2 Ni1 -6.6(2) . . . . ?
O3 S1 C23 F2 56.8(3) . . . . ?
O3 S1 C23 F3 177.2(2) . . . . ?
O3 S1 C23 F1 -63.2(3) . . . . ?
N3 C12 C10 N2 0.2(3) . . . . ?
N3 C12 C10 C11 -178.9(2) . . . . ?
N3 C14 C15 C17 178.9(2) . . . . ?
N3 C14 C15 C16 -0.9(4) . . . . ?
N3 C14 C21 C20 -177.6(2) . . . . ?
N3 C14 C21 C22 3.4(4) . . . . ?
N2 C9 C2 C3 176.7(2) . . . . ?
N2 C9 C2 C1 -3.3(4) . . . . ?
O4 S1 O2 Ni1 130.12(17) . . . . ?
O4 S1 C23 F2 -65.7(3) . . . . ?
O4 S1 C23 F3 54.7(3) . . . . ?
O4 S1 C23 F1 174.3(3) . . . . ?
C7 C9 C2 C3 -0.1(4) . . . . ?
C7 C9 C2 C1 179.9(3) . . . . ?
C7 C6 C4 C3 0.7(4) . . . . ?
C7 C6 C4 C5 -178.6(3) . . . . ?
C12 N3 C14 C15 98.6(3) . . . . ?
C12 N3 C14 C21 -83.4(3) . . . . ?
C10 N2 C9 C7 -109.6(3) . . . . ?
C10 N2 C9 C2 73.5(3) . . . . ?
C9 N2 C10 C12 -174.7(2) . . . . ?
C9 N2 C10 C11 4.3(4) . . . . ?
C9 C7 C6 C4 0.2(4) . . . . ?
C9 C2 C3 C4 1.0(4) . . . . ?
C14 N3 C12 C10 177.5(2) . . . . ?
C14 N3 C12 C13 -1.2(4) . . . . ?
C14 C15 C17 C18 -1.2(4) . . . . ?
C14 C21 C20 C18 -1.5(4) . . . . ?
C15 C14 C21 C20 0.3(4) . . . . ?
C15 C14 C21 C22 -178.7(3) . . . . ?
C15 C17 C18 C20 0.1(4) . . . . ?
C15 C17 C18 C19 -179.1(3) . . . . ?
C21 C14 C15 C17 1.0(4) . . . . ?
C21 C14 C15 C16 -178.8(3) . . . . ?
C2 C3 C4 C6 -1.3(4) . . . . ?
C2 C3 C4 C5 177.9(3) . . . . ?
C8 C7 C9 N2 4.1(4) . . . . ?
C8 C7 C9 C2 -179.1(2) . . . . ?
C8 C7 C6 C4 178.8(3) . . . . ?
C13 C12 C10 N2 179.1(2) . . . . ?
C13 C12 C10 C11 0.0(4) . . . . ?
C17 C18 C20 C21 1.4(4) . . . . ?
C6 C7 C9 N2 -177.3(2) . . . . ?
C6 C7 C9 C2 -0.5(4) . . . . ?
C16 C15 C17 C18 178.6(3) . . . . ?
C22 C21 C20 C18 177.5(3) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
C19 C18 C20 C21 -179.5(3) . . . . ?
C23 S1 O2 Ni1 -119.14(18) . . . . ?

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

data_20009
_database_code_depnum_ccdc_archive 'CCDC 2083111'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana University
United States of America
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 N4 Ni O3'
_chemical_formula_sum            'C22 H28 N4 Ni O3'
_chemical_formula_weight         455.19

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      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                   11.6060(7)
_cell_length_b                   16.8019(11)
_cell_length_c                   12.3281(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.731(2)
_cell_angle_gamma                90
_cell_volume                     2233.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9006
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      28.17

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.899
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6718
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2018'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_details      
'0.50 degree frames measured for 2 seconds each'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            51982
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.060
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5558
_reflns_number_gt                4368
_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       'BIS v6.2.9 (BrukerNano, 2018)'
_computing_cell_refinement       'SAINT V8.38A (BrukerNano, 2017)'
_computing_data_reduction        'SAINT V8.38A (BrukerNano, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 v2018.1-0 (BrukerNano, 2018)'
_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)+(0.0348P)²+3.2020P] 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         5558
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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 0.76472(3) 0.71244(2) 0.57350(3) 0.01404(9) Uani 1 1 d . . . . .
O1 O 0.92694(18) 0.83132(12) 0.55499(18) 0.0290(4) Uani 1 1 d . . . . .
O2 O 0.81564(18) 0.60916(11) 0.65754(16) 0.0253(4) Uani 1 1 d . . . . .
O3 O 0.9250(2) 0.67730(12) 0.80402(17) 0.0314(5) Uani 1 1 d . . . . .
N1 N 0.60565(18) 0.72989(11) 0.60138(17) 0.0141(4) Uani 1 1 d . . . . .
N2 N 0.64319(18) 0.65975(11) 0.43081(16) 0.0127(4) Uani 1 1 d . . . . .
N3 N 0.86130(19) 0.78177(12) 0.56744(18) 0.0177(4) Uani 1 1 d . . . . .
N4 N 0.8933(2) 0.61060(13) 0.7632(2) 0.0245(5) Uani 1 1 d . . . . .
C1 C 0.5922(2) 0.77079(13) 0.6987(2) 0.0137(4) Uani 1 1 d . . . . .
C2 C 0.5806(2) 0.72622(14) 0.7898(2) 0.0149(5) Uani 1 1 d . . . . .
C3 C 0.5611(2) 0.76730(14) 0.8800(2) 0.0163(5) Uani 1 1 d . . . . .
H3 H 0.551436 0.737842 0.941827 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5555(2) 0.84975(14) 0.8822(2) 0.0163(5) Uani 1 1 d . . . . .
C5 C 0.5725(2) 0.89230(14) 0.7921(2) 0.0167(5) Uani 1 1 d . . . . .
H5 H 0.572194 0.948809 0.794335 0.020 Uiso 1 1 calc R U . . .
C6 C 0.5899(2) 0.85424(14) 0.6986(2) 0.0144(4) Uani 1 1 d . . . . .
C7 C 0.5863(2) 0.63667(14) 0.7912(2) 0.0208(5) Uani 1 1 d . . . . .
H7A H 0.508445 0.615286 0.735132 0.031 Uiso 1 1 calc R U . . .
H7B H 0.598480 0.617274 0.869686 0.031 Uiso 1 1 calc R U . . .
H7C H 0.655534 0.619171 0.769761 0.031 Uiso 1 1 calc R U . . .
C8 C 0.5279(2) 0.89249(16) 0.9769(2) 0.0222(5) Uani 1 1 d . . . . .
H8A H 0.439375 0.905614 0.949146 0.033 Uiso 1 1 calc R U . . .
H8B H 0.576827 0.941572 0.997537 0.033 Uiso 1 1 calc R U . . .
H8C H 0.549407 0.858166 1.045895 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6042(2) 0.90141(15) 0.6007(2) 0.0200(5) Uani 1 1 d . . . . .
H9A H 0.684127 0.888768 0.594872 0.030 Uiso 1 1 calc R U . . .
H9B H 0.600862 0.958380 0.616324 0.030 Uiso 1 1 calc R U . . .
H9C H 0.536887 0.887823 0.527138 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5072(2) 0.70870(13) 0.5163(2) 0.0138(4) Uani 1 1 d . . . . .
C11 C 0.5284(2) 0.66387(13) 0.42031(19) 0.0131(4) Uani 1 1 d . . . . .
C12 C 0.3783(2) 0.72714(14) 0.5076(2) 0.0172(5) Uani 1 1 d . . . . .
H12A H 0.374708 0.726333 0.585774 0.026 Uiso 1 1 calc R U . . .
H12B H 0.321140 0.687189 0.458426 0.026 Uiso 1 1 calc R U . . .
H12C H 0.354426 0.779986 0.472924 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4214(2) 0.62857(14) 0.3238(2) 0.0165(5) Uani 1 1 d . . . . .
H13A H 0.451208 0.601878 0.268459 0.025 Uiso 1 1 calc R U . . .
H13B H 0.363012 0.670788 0.283344 0.025 Uiso 1 1 calc R U . . .
H13C H 0.379488 0.589821 0.355919 0.025 Uiso 1 1 calc R U . . .
C14 C 0.6770(2) 0.61737(14) 0.3461(2) 0.0132(4) Uani 1 1 d . . . . .
C15 C 0.7065(2) 0.66090(14) 0.2632(2) 0.0152(5) Uani 1 1 d . . . . .
C16 C 0.7416(2) 0.61862(15) 0.1835(2) 0.0196(5) Uani 1 1 d . . . . .
H16 H 0.760339 0.647186 0.125575 0.024 Uiso 1 1 calc R U . . .
C17 C 0.7504(2) 0.53612(15) 0.1855(2) 0.0196(5) Uani 1 1 d . . . . .
C18 C 0.7218(2) 0.49516(15) 0.2698(2) 0.0189(5) Uani 1 1 d . . . . .
H18 H 0.727227 0.438730 0.271966 0.023 Uiso 1 1 calc R U . . .
C19 C 0.6852(2) 0.53438(14) 0.3518(2) 0.0153(5) Uani 1 1 d . . . . .
C20 C 0.6984(3) 0.75061(15) 0.2584(2) 0.0219(5) Uani 1 1 d . . . . .
H20A H 0.616550 0.767346 0.255828 0.033 Uiso 1 1 calc R U . . .
H20B H 0.710769 0.769686 0.188411 0.033 Uiso 1 1 calc R U . . .
H20C H 0.762718 0.773007 0.328037 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7897(3) 0.49217(18) 0.0980(3) 0.0297(6) Uani 1 1 d . . . . .
H21A H 0.718529 0.463323 0.043237 0.045 Uiso 1 1 calc R U . . .
H21B H 0.855690 0.454314 0.139135 0.045 Uiso 1 1 calc R U . . .
H21C H 0.820440 0.530344 0.054990 0.045 Uiso 1 1 calc R U . . .
C22 C 0.6568(2) 0.48859(14) 0.4436(2) 0.0202(5) Uani 1 1 d . . . . .
H22A H 0.683625 0.433246 0.444159 0.030 Uiso 1 1 calc R U . . .
H22B H 0.567270 0.490022 0.426169 0.030 Uiso 1 1 calc R U . . .
H22C H 0.700823 0.512648 0.520253 0.030 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 N3 1.637(2) . ?
Ni1 O2 1.9952(19) . ?
Ni1 N2 2.0075(19) . ?
Ni1 N1 2.0204(19) . ?
O1 N3 1.176(3) . ?
O2 N4 1.280(3) . ?
O3 N4 1.228(3) . ?
N1 C10 1.282(3) . ?
N1 C1 1.441(3) . ?
N2 C11 1.291(3) . ?
N2 C14 1.434(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.506(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 C8 1.503(3) . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C9 1.503(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.493(3) . ?
C10 C11 1.498(3) . ?
C11 C13 1.489(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.398(3) . ?
C14 C15 1.399(3) . ?
C15 C16 1.390(3) . ?
C15 C20 1.510(3) . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 C21 1.510(3) . ?
C18 C19 1.398(3) . ?
C18 H18 0.9500 . ?
C19 C22 1.502(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Ni1 O2 124.50(9) . . ?
N3 Ni1 N2 122.99(9) . . ?
O2 Ni1 N2 92.78(8) . . ?
N3 Ni1 N1 126.05(9) . . ?
O2 Ni1 N1 98.71(8) . . ?
N2 Ni1 N1 79.82(8) . . ?
N4 O2 Ni1 118.25(16) . . ?
C10 N1 C1 118.40(19) . . ?
C10 N1 Ni1 114.43(15) . . ?
C1 N1 Ni1 126.76(15) . . ?
C11 N2 C14 120.27(19) . . ?
C11 N2 Ni1 115.35(15) . . ?
C14 N2 Ni1 124.34(15) . . ?
O1 N3 Ni1 175.5(2) . . ?
O3 N4 O2 115.2(2) . . ?
C2 C1 C6 122.0(2) . . ?
C2 C1 N1 119.1(2) . . ?
C6 C1 N1 118.9(2) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 C7 120.3(2) . . ?
C1 C2 C7 121.9(2) . . ?
C4 C3 C2 122.2(2) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 C8 121.2(2) . . ?
C5 C4 C8 120.5(2) . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 117.7(2) . . ?
C5 C6 C9 120.9(2) . . ?
C1 C6 C9 121.4(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C12 124.5(2) . . ?
N1 C10 C11 115.4(2) . . ?
C12 C10 C11 120.1(2) . . ?
N2 C11 C13 125.7(2) . . ?
N2 C11 C10 114.4(2) . . ?
C13 C11 C10 120.0(2) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 121.9(2) . . ?
C19 C14 N2 119.4(2) . . ?
C15 C14 N2 118.7(2) . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 C20 120.9(2) . . ?
C14 C15 C20 121.4(2) . . ?
C17 C16 C15 122.4(2) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C18 C17 C16 118.2(2) . . ?
C18 C17 C21 120.8(2) . . ?
C16 C17 C21 121.0(2) . . ?
C17 C18 C19 122.0(2) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C14 C19 C18 117.9(2) . . ?
C14 C19 C22 121.3(2) . . ?
C18 C19 C22 120.9(2) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Ni1 O2 N4 O3 3.0(3) . . . . ?
C10 N1 C1 C2 86.7(3) . . . . ?
Ni1 N1 C1 C2 -101.0(2) . . . . ?
C10 N1 C1 C6 -92.7(3) . . . . ?
Ni1 N1 C1 C6 79.6(3) . . . . ?
C6 C1 C2 C3 2.7(3) . . . . ?
N1 C1 C2 C3 -176.7(2) . . . . ?
C6 C1 C2 C7 -178.4(2) . . . . ?
N1 C1 C2 C7 2.2(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C7 C2 C3 C4 179.9(2) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C2 C3 C4 C8 176.8(2) . . . . ?
C3 C4 C5 C6 2.5(4) . . . . ?
C8 C4 C5 C6 -175.6(2) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C9 178.1(2) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
N1 C1 C6 C5 177.8(2) . . . . ?
C2 C1 C6 C9 179.2(2) . . . . ?
N1 C1 C6 C9 -1.5(3) . . . . ?
C1 N1 C10 C12 3.3(3) . . . . ?
Ni1 N1 C10 C12 -169.85(18) . . . . ?
C1 N1 C10 C11 -177.83(19) . . . . ?
Ni1 N1 C10 C11 9.0(3) . . . . ?
C14 N2 C11 C13 -1.0(3) . . . . ?
Ni1 N2 C11 C13 -178.97(18) . . . . ?
C14 N2 C11 C10 178.91(19) . . . . ?
Ni1 N2 C11 C10 1.0(2) . . . . ?
N1 C10 C11 N2 -6.7(3) . . . . ?
C12 C10 C11 N2 172.1(2) . . . . ?
N1 C10 C11 C13 173.2(2) . . . . ?
C12 C10 C11 C13 -7.9(3) . . . . ?
C11 N2 C14 C19 -79.2(3) . . . . ?
Ni1 N2 C14 C19 98.5(2) . . . . ?
C11 N2 C14 C15 103.7(3) . . . . ?
Ni1 N2 C14 C15 -78.6(2) . . . . ?
C19 C14 C15 C16 1.6(4) . . . . ?
N2 C14 C15 C16 178.7(2) . . . . ?
C19 C14 C15 C20 -179.4(2) . . . . ?
N2 C14 C15 C20 -2.4(3) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C20 C15 C16 C17 179.8(2) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C15 C16 C17 C21 -179.6(2) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C21 C17 C18 C19 179.9(2) . . . . ?
C15 C14 C19 C18 -1.3(4) . . . . ?
N2 C14 C19 C18 -178.3(2) . . . . ?
C15 C14 C19 C22 178.2(2) . . . . ?
N2 C14 C19 C22 1.2(3) . . . . ?
C17 C18 C19 C14 0.5(4) . . . . ?
C17 C18 C19 C22 -179.0(2) . . . . ?

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
_geom_hbond_publ_flag
C12 H12C O3 0.98 2.60 3.190(3) 118.5 4_575 yes
C13 H13B O3 0.98 2.64 3.272(3) 122.6 4_575 yes

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.088



####################################################################### 
# 
# 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_19121_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2083108'
loop_
_audit_author_name
_audit_author_address
'Veronica Carta'
;Indiana University
United States of America
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
dbeagan@iu.edu
acabelof@iu.edu
vcarta@iu.edu
caulton@indiana.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H28 N4 Ni O4)'
_chemical_formula_sum            'C44 H56 N8 Ni2 O8'
_chemical_formula_weight         942.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.866(3)
_cell_length_b                   14.341(3)
_cell_length_c                   23.383(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4649.5(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5686
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      21.77
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex 3 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1984
_exptl_crystal_preparation       syntehsized
_exptl_crystal_recrystallization_method 
'vapor diffurion of pentane into a tetrahydrofuran solution'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1819
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            66234
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.257
_diffrn_reflns_theta_min         2.221
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker VENTURE D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                6583
_reflns_number_total             8294
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 2405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     576
_refine_ls_number_reflns         8294
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0620
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0138P)²+9.2399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1196
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.47(3)
 0.53(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C17A(H17A), C20A(H20A), C6A(H6A), C3(H3), C6(H6), C17(H17), C20(H20), C3A(H3A)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C8(H8A,H8B,H8C), C11A(H11D,H11E,H11F), C13(H13A,H13B,
 H13C), C13A(H13D,H13E,H13F), C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC), C22A(H22D,
 H22E,H22F), C16(H16A,H16B,H16C), C8A(H8AA,H8AB,H8AC), C22(H22A,H22B,H22C),
 C16A(H16D,H16E,H16F), C19A(H19D,H19E,H19F), C5A(H5AA,H5AB,H5AC), C19(H19A,H19B,
 H19C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.37472(8) 0.24738(7) 0.51592(5) 0.0169(2) Uani 1 1 d . . . . .
Ni1A Ni 0.37275(8) 0.73139(7) 0.47731(4) 0.0183(3) Uani 1 1 d . . . . .
O1 O 0.4656(5) 0.3609(4) 0.5325(3) 0.0239(16) Uani 1 1 d . . . . .
O4 O 0.2362(4) 0.1933(4) 0.5127(4) 0.0250(14) Uani 1 1 d . . . . .
O2 O 0.3414(4) 0.3775(4) 0.4807(3) 0.0238(13) Uani 1 1 d . . . . .
N3 N 0.4421(5) 0.1913(5) 0.4467(3) 0.0140(16) Uani 1 1 d . . . . .
N4A N 0.4226(5) 0.6749(5) 0.5523(3) 0.0144(16) Uani 1 1 d . . . . .
O1A O 0.4609(5) 0.8459(4) 0.4629(3) 0.0288(18) Uani 1 1 d . . . . .
O4A O 0.2357(4) 0.6721(4) 0.4789(3) 0.0293(15) Uani 1 1 d . . . . .
O3 O 0.2768(5) 0.2815(4) 0.5811(3) 0.0275(15) Uani 1 1 d . . . . .
N4 N 0.4538(5) 0.1460(5) 0.5550(3) 0.0148(17) Uani 1 1 d . . . . .
N3A N 0.4710(5) 0.6387(5) 0.4455(4) 0.0165(18) Uani 1 1 d . . . . .
O3A O 0.2578(4) 0.8089(4) 0.5099(3) 0.0294(15) Uani 1 1 d . . . . .
O2A O 0.3588(5) 0.8069(5) 0.4011(3) 0.0345(17) Uani 1 1 d . . . . .
C14 C 0.4521(6) 0.1268(6) 0.6148(4) 0.0146(18) Uani 1 1 d . . . . .
C9 C 0.4204(6) 0.2090(6) 0.3869(4) 0.018(2) Uani 1 1 d . . . . .
C10A C 0.5221(6) 0.5991(5) 0.4831(5) 0.019(2) Uani 1 1 d . . . . .
C14A C 0.3892(6) 0.6937(6) 0.6084(4) 0.018(2) Uani 1 1 d . . . . .
C9A C 0.4912(6) 0.6290(6) 0.3847(4) 0.0158(19) Uani 1 1 d . . . . .
C15A C 0.3266(6) 0.6299(6) 0.6355(4) 0.018(2) Uani 1 1 d . . . . .
C12A C 0.4944(7) 0.6179(6) 0.5447(4) 0.017(2) Uani 1 1 d . . . . .
N1 N 0.4124(5) 0.4182(5) 0.5042(3) 0.0253(19) Uani 1 1 d . . . . .
C10 C 0.5064(6) 0.1297(6) 0.4596(4) 0.018(2) Uani 1 1 d . . . . .
C7A C 0.4228(6) 0.5833(6) 0.3506(4) 0.018(2) Uani 1 1 d . . . . .
C12 C 0.5153(6) 0.1054(5) 0.5211(5) 0.0161(19) Uani 1 1 d . . . . .
C7 C 0.3523(6) 0.1497(6) 0.3602(4) 0.021(2) Uani 1 1 d . . . . .
C2 C 0.4604(6) 0.2844(6) 0.3577(4) 0.022(2) Uani 1 1 d . . . . .
C18A C 0.3239(6) 0.7322(6) 0.7192(4) 0.021(2) Uani 1 1 d . . . . .
C11 C 0.5704(6) 0.0810(6) 0.4171(4) 0.022(2) Uani 1 1 d . . . . .
H11A H 0.554385 0.102004 0.378352 0.033 Uiso 1 1 calc GR . . . .
H11B H 0.560645 0.013472 0.419853 0.033 Uiso 1 1 calc GR . . . .
H11C H 0.638025 0.095783 0.425360 0.033 Uiso 1 1 calc GR . . . .
C8 C 0.3067(7) 0.0693(6) 0.3915(5) 0.025(2) Uani 1 1 d . . . . .
H8A H 0.357130 0.026905 0.405095 0.038 Uiso 1 1 calc GR . . . .
H8B H 0.263343 0.035700 0.365572 0.038 Uiso 1 1 calc GR . . . .
H8C H 0.269861 0.092971 0.424185 0.038 Uiso 1 1 calc GR . . . .
C21A C 0.4183(6) 0.7764(6) 0.6352(4) 0.020(2) Uani 1 1 d . . . . .
C15 C 0.3789(6) 0.0696(6) 0.6371(4) 0.0189(19) Uani 1 1 d . . . . .
C11A C 0.6089(5) 0.5372(6) 0.4726(4) 0.0200(19) Uani 1 1 d . . . . .
H11D H 0.616538 0.526929 0.431371 0.030 Uiso 1 1 calc GR . . . .
H11E H 0.599459 0.477245 0.491812 0.030 Uiso 1 1 calc GR . . . .
H11F H 0.666885 0.567566 0.487689 0.030 Uiso 1 1 calc GR . . . .
C13 C 0.5873(6) 0.0348(6) 0.5392(4) 0.021(2) Uani 1 1 d . . . . .
H13A H 0.584470 0.027022 0.580770 0.031 Uiso 1 1 calc GR . . . .
H13B H 0.652050 0.055578 0.528124 0.031 Uiso 1 1 calc GR . . . .
H13C H 0.573101 -0.024886 0.520560 0.031 Uiso 1 1 calc GR . . . .
C21 C 0.5209(6) 0.1690(6) 0.6508(4) 0.021(2) Uani 1 1 d . . . . .
C2A C 0.5749(6) 0.6683(6) 0.3612(4) 0.021(2) Uani 1 1 d . . . . .
C17A C 0.2955(6) 0.6510(7) 0.6906(4) 0.021(2) Uani 1 1 d . . . . .
H17A H 0.253416 0.608727 0.709403 0.025 Uiso 1 1 calc R . . . .
C13A C 0.5489(6) 0.5702(6) 0.5913(4) 0.019(2) Uani 1 1 d . . . . .
H13D H 0.526619 0.593265 0.628442 0.028 Uiso 1 1 calc GR . . . .
H13E H 0.617923 0.583126 0.587041 0.028 Uiso 1 1 calc GR . . . .
H13F H 0.537916 0.502756 0.588971 0.028 Uiso 1 1 calc GR . . . .
C20A C 0.3852(6) 0.7932(6) 0.6914(4) 0.023(2) Uani 1 1 d . . . . .
H20A H 0.405613 0.848050 0.710667 0.027 Uiso 1 1 calc R . . . .
C6A C 0.4422(7) 0.5730(6) 0.2923(4) 0.024(2) Uani 1 1 d . . . . .
H6A H 0.397287 0.541166 0.268610 0.029 Uiso 1 1 calc R . . . .
C3 C 0.4343(7) 0.2986(7) 0.3017(4) 0.027(2) Uani 1 1 d . . . . .
H3 H 0.463670 0.348258 0.281245 0.033 Uiso 1 1 calc R . . . .
C1 C 0.5343(7) 0.3463(7) 0.3866(4) 0.029(2) Uani 1 1 d . . . . .
H1A H 0.506208 0.408034 0.393446 0.043 Uiso 1 1 calc GR . . . .
H1B H 0.591033 0.352515 0.361908 0.043 Uiso 1 1 calc GR . . . .
H1C H 0.553403 0.318442 0.423141 0.043 Uiso 1 1 calc GR . . . .
C6 C 0.3283(6) 0.1682(6) 0.3033(4) 0.022(2) Uani 1 1 d . . . . .
H6 H 0.284332 0.128003 0.284221 0.026 Uiso 1 1 calc R . . . .
C1A C 0.6469(6) 0.7217(6) 0.3970(4) 0.027(2) Uani 1 1 d . . . . .
H1AA H 0.614065 0.748974 0.430090 0.040 Uiso 1 1 calc GR . . . .
H1AB H 0.675684 0.771437 0.373883 0.040 Uiso 1 1 calc GR . . . .
H1AC H 0.697619 0.679196 0.410142 0.040 Uiso 1 1 calc GR . . . .
C22A C 0.4830(7) 0.8451(6) 0.6061(5) 0.027(2) Uani 1 1 d . . . . .
H22D H 0.546667 0.817004 0.600290 0.040 Uiso 1 1 calc GR . . . .
H22E H 0.489413 0.900908 0.630015 0.040 Uiso 1 1 calc GR . . . .
H22F H 0.455306 0.862354 0.569056 0.040 Uiso 1 1 calc GR . . . .
C17 C 0.3779(7) 0.0528(6) 0.6955(4) 0.025(2) Uani 1 1 d . . . . .
H17 H 0.329197 0.013474 0.710746 0.030 Uiso 1 1 calc R . . . .
C20 C 0.5157(7) 0.1487(7) 0.7086(4) 0.029(2) Uani 1 1 d . . . . .
H20 H 0.562517 0.175381 0.733310 0.035 Uiso 1 1 calc R . . . .
N2 N 0.2087(6) 0.2376(6) 0.5578(4) 0.035(2) Uani 1 1 d . . . . .
C4 C 0.3667(7) 0.2434(7) 0.2736(4) 0.029(2) Uani 1 1 d . . . . .
N2A N 0.1967(6) 0.7459(6) 0.4986(3) 0.036(2) Uani 1 1 d . . . . .
C16 C 0.3036(7) 0.0247(7) 0.5991(4) 0.027(2) Uani 1 1 d . . . . .
H16A H 0.243719 0.060867 0.600949 0.040 Uiso 1 1 calc GR . . . .
H16B H 0.291398 -0.039111 0.612131 0.040 Uiso 1 1 calc GR . . . .
H16C H 0.327101 0.023456 0.559562 0.040 Uiso 1 1 calc GR . . . .
C8A C 0.3307(6) 0.5447(6) 0.3748(4) 0.023(2) Uani 1 1 d . . . . .
H8AA H 0.345725 0.499632 0.405035 0.035 Uiso 1 1 calc GR . . . .
H8AB H 0.294058 0.513696 0.344446 0.035 Uiso 1 1 calc GR . . . .
H8AC H 0.292102 0.595705 0.390847 0.035 Uiso 1 1 calc GR . . . .
C3A C 0.5907(7) 0.6572(7) 0.3035(4) 0.027(2) Uani 1 1 d . . . . .
H3A H 0.647211 0.683510 0.287093 0.032 Uiso 1 1 calc R . . . .
N1A N 0.4255(6) 0.8639(6) 0.4144(4) 0.037(2) Uani 1 1 d . . . . .
C18 C 0.4451(7) 0.0910(7) 0.7324(4) 0.030(2) Uani 1 1 d . . . . .
C4A C 0.5271(7) 0.6090(6) 0.2681(4) 0.026(2) Uani 1 1 d . . . . .
C22 C 0.5998(7) 0.2302(7) 0.6273(5) 0.034(2) Uani 1 1 d . . . . .
H22A H 0.650627 0.191180 0.610713 0.050 Uiso 1 1 calc GR . . . .
H22B H 0.626994 0.268114 0.658268 0.050 Uiso 1 1 calc GR . . . .
H22C H 0.573243 0.271225 0.597732 0.050 Uiso 1 1 calc GR . . . .
C16A C 0.2941(7) 0.5425(7) 0.6058(4) 0.028(2) Uani 1 1 d . . . . .
H16D H 0.270199 0.558103 0.567523 0.043 Uiso 1 1 calc GR . . . .
H16E H 0.242444 0.513099 0.627951 0.043 Uiso 1 1 calc GR . . . .
H16F H 0.348604 0.499280 0.602467 0.043 Uiso 1 1 calc GR . . . .
C19A C 0.2858(7) 0.7544(7) 0.7790(4) 0.032(2) Uani 1 1 d . . . . .
H19D H 0.227530 0.792709 0.775873 0.048 Uiso 1 1 calc GR . . . .
H19E H 0.335086 0.788535 0.800567 0.048 Uiso 1 1 calc GR . . . .
H19F H 0.270373 0.696168 0.798963 0.048 Uiso 1 1 calc GR . . . .
C5A C 0.5492(8) 0.5948(7) 0.2050(4) 0.039(3) Uani 1 1 d . . . . .
H5AA H 0.575690 0.532170 0.199135 0.058 Uiso 1 1 calc GR . . . .
H5AB H 0.596384 0.641415 0.192460 0.058 Uiso 1 1 calc GR . . . .
H5AC H 0.489789 0.601707 0.182682 0.058 Uiso 1 1 calc GR . . . .
C19 C 0.4447(8) 0.0686(8) 0.7957(4) 0.041(3) Uani 1 1 d . . . . .
H19A H 0.384976 0.035784 0.805493 0.062 Uiso 1 1 calc GR . . . .
H19B H 0.448714 0.126672 0.817679 0.062 Uiso 1 1 calc GR . . . .
H19C H 0.500174 0.029005 0.804832 0.062 Uiso 1 1 calc GR . . . .
C5 C 0.3371(8) 0.2629(9) 0.2125(5) 0.042(3) Uani 1 1 d . . . . .
H5A H 0.295789 0.318293 0.211393 0.062 Uiso 1 1 calc GR . . . .
H5B H 0.301518 0.209217 0.197339 0.062 Uiso 1 1 calc GR . . . .
H5C H 0.394728 0.273672 0.189188 0.062 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 2.094(6) . ?
Ni1 O4 2.072(6) . ?
Ni1 O2 2.091(6) . ?
Ni1 N3 2.035(7) . ?
Ni1 O3 2.099(6) . ?
Ni1 N4 2.038(7) . ?
Ni1A N4A 2.051(8) . ?
Ni1A O1A 2.074(6) . ?
Ni1A O4A 2.082(6) . ?
Ni1A N3A 2.043(8) . ?
Ni1A O3A 2.088(6) . ?
Ni1A O2A 2.093(6) . ?
O1 N1 1.287(9) . ?
O4 N2 1.290(11) . ?
O2 N1 1.269(9) . ?
N3 C9 1.452(12) . ?
N3 C10 1.291(11) . ?
N4A C14A 1.418(12) . ?
N4A C12A 1.301(12) . ?
O1A N1A 1.262(11) . ?
O4A N2A 1.274(10) . ?
O3 N2 1.257(10) . ?
N4 C14 1.425(12) . ?
N4 C12 1.303(12) . ?
N3A C10A 1.262(12) . ?
N3A C9A 1.457(12) . ?
O3A N2A 1.267(10) . ?
O2A N1A 1.274(11) . ?
C14 C15 1.406(12) . ?
C14 C21 1.409(12) . ?
C9 C7 1.417(12) . ?
C9 C2 1.394(12) . ?
C10A C12A 1.515(14) . ?
C10A C11A 1.515(11) . ?
C14A C15A 1.412(12) . ?
C14A C21A 1.400(12) . ?
C9A C7A 1.401(12) . ?
C9A C2A 1.403(12) . ?
C15A C17A 1.390(13) . ?
C15A C16A 1.503(13) . ?
C12A C13A 1.492(13) . ?
C10 C12 1.485(15) . ?
C10 C11 1.504(12) . ?
C7A C6A 1.397(14) . ?
C7A C8A 1.504(12) . ?
C12 C13 1.483(12) . ?
C7 C8 1.505(13) . ?
C7 C6 1.397(14) . ?
C2 C3 1.373(14) . ?
C2 C1 1.515(13) . ?
C18A C17A 1.400(13) . ?
C18A C20A 1.382(13) . ?
C18A C19A 1.528(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C21A C20A 1.413(13) . ?
C21A C22A 1.496(12) . ?
C15 C17 1.385(12) . ?
C15 C16 1.514(12) . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 C20 1.384(14) . ?
C21 C22 1.507(13) . ?
C2A C1A 1.511(12) . ?
C2A C3A 1.377(13) . ?
C17A H17A 0.9500 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C20A H20A 0.9500 . ?
C6A H6A 0.9500 . ?
C6A C4A 1.403(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C4 1.388(13) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C17 H17 0.9500 . ?
C17 C18 1.382(14) . ?
C20 H20 0.9500 . ?
C20 C18 1.398(14) . ?
C4 C5 1.512(15) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C3A H3A 0.9500 . ?
C3A C4A 1.393(13) . ?
C18 C19 1.515(14) . ?
C4A C5A 1.522(14) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 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 O3 94.2(3) . . ?
O4 Ni1 O1 148.8(3) . . ?
O4 Ni1 O2 96.6(2) . . ?
O4 Ni1 O3 60.9(3) . . ?
O2 Ni1 O1 60.8(2) . . ?
O2 Ni1 O3 86.3(2) . . ?
N3 Ni1 O1 100.3(3) . . ?
N3 Ni1 O4 104.4(3) . . ?
N3 Ni1 O2 98.1(3) . . ?
N3 Ni1 O3 165.2(3) . . ?
N3 Ni1 N4 80.1(3) . . ?
N4 Ni1 O1 98.5(3) . . ?
N4 Ni1 O4 104.4(3) . . ?
N4 Ni1 O2 158.8(2) . . ?
N4 Ni1 O3 100.9(3) . . ?
N4A Ni1A O1A 104.7(3) . . ?
N4A Ni1A O4A 97.5(3) . . ?
N4A Ni1A O3A 98.9(3) . . ?
N4A Ni1A O2A 164.3(3) . . ?
O1A Ni1A O4A 149.7(3) . . ?
O1A Ni1A O3A 95.0(3) . . ?
O1A Ni1A O2A 60.5(3) . . ?
O4A Ni1A O3A 60.9(3) . . ?
O4A Ni1A O2A 98.1(3) . . ?
N3A Ni1A N4A 80.1(3) . . ?
N3A Ni1A O1A 93.6(3) . . ?
N3A Ni1A O4A 110.5(3) . . ?
N3A Ni1A O3A 171.2(3) . . ?
N3A Ni1A O2A 95.1(3) . . ?
O3A Ni1A O2A 88.0(3) . . ?
N1 O1 Ni1 93.2(5) . . ?
N2 O4 Ni1 93.4(5) . . ?
N1 O2 Ni1 94.0(4) . . ?
C9 N3 Ni1 127.0(5) . . ?
C10 N3 Ni1 113.7(6) . . ?
C10 N3 C9 119.2(7) . . ?
C14A N4A Ni1A 127.3(5) . . ?
C12A N4A Ni1A 112.9(6) . . ?
C12A N4A C14A 119.8(8) . . ?
N1A O1A Ni1A 94.6(5) . . ?
N2A O4A Ni1A 93.2(5) . . ?
N2 O3 Ni1 93.1(5) . . ?
C14 N4 Ni1 124.7(6) . . ?
C12 N4 Ni1 113.4(7) . . ?
C12 N4 C14 121.5(8) . . ?
C10A N3A Ni1A 114.5(7) . . ?
C10A N3A C9A 121.9(8) . . ?
C9A N3A Ni1A 123.0(6) . . ?
N2A O3A Ni1A 93.1(5) . . ?
N1A O2A Ni1A 93.3(6) . . ?
C15 C14 N4 119.3(8) . . ?
C15 C14 C21 121.2(9) . . ?
C21 C14 N4 119.5(8) . . ?
C7 C9 N3 117.2(8) . . ?
C2 C9 N3 121.7(8) . . ?
C2 C9 C7 121.0(9) . . ?
N3A C10A C12A 116.0(8) . . ?
N3A C10A C11A 126.6(10) . . ?
C12A C10A C11A 117.3(8) . . ?
C15A C14A N4A 119.5(8) . . ?
C21A C14A N4A 118.8(8) . . ?
C21A C14A C15A 121.6(9) . . ?
C7A C9A N3A 118.1(7) . . ?
C7A C9A C2A 121.6(8) . . ?
C2A C9A N3A 120.2(8) . . ?
C14A C15A C16A 121.1(9) . . ?
C17A C15A C14A 117.8(8) . . ?
C17A C15A C16A 121.1(8) . . ?
N4A C12A C10A 115.8(8) . . ?
N4A C12A C13A 125.2(9) . . ?
C13A C12A C10A 119.0(8) . . ?
O2 N1 O1 111.9(6) . . ?
N3 C10 C12 116.4(8) . . ?
N3 C10 C11 124.8(9) . . ?
C12 C10 C11 118.8(8) . . ?
C9A C7A C8A 122.1(8) . . ?
C6A C7A C9A 118.4(8) . . ?
C6A C7A C8A 119.5(8) . . ?
N4 C12 C10 115.5(8) . . ?
N4 C12 C13 124.9(9) . . ?
C13 C12 C10 119.5(8) . . ?
C9 C7 C8 121.7(9) . . ?
C6 C7 C9 117.7(8) . . ?
C6 C7 C8 120.6(8) . . ?
C9 C2 C1 120.3(9) . . ?
C3 C2 C9 118.5(9) . . ?
C3 C2 C1 121.2(8) . . ?
C17A C18A C19A 120.9(8) . . ?
C20A C18A C17A 118.3(9) . . ?
C20A C18A C19A 120.8(8) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14A C21A C20A 117.8(8) . . ?
C14A C21A C22A 121.8(8) . . ?
C20A C21A C22A 120.4(8) . . ?
C14 C15 C16 121.8(8) . . ?
C17 C15 C14 118.3(8) . . ?
C17 C15 C16 119.9(8) . . ?
C10A C11A H11D 109.5 . . ?
C10A C11A H11E 109.5 . . ?
C10A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C21 C22 121.7(9) . . ?
C20 C21 C14 117.2(8) . . ?
C20 C21 C22 121.0(9) . . ?
C9A C2A C1A 122.3(8) . . ?
C3A C2A C9A 118.0(8) . . ?
C3A C2A C1A 119.7(8) . . ?
C15A C17A C18A 122.4(8) . . ?
C15A C17A H17A 118.8 . . ?
C18A C17A H17A 118.8 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C18A C20A C21A 122.0(8) . . ?
C18A C20A H20A 119.0 . . ?
C21A C20A H20A 119.0 . . ?
C7A C6A H6A 119.5 . . ?
C7A C6A C4A 121.0(9) . . ?
C4A C6A H6A 119.5 . . ?
C2 C3 H3 118.5 . . ?
C2 C3 C4 122.9(9) . . ?
C4 C3 H3 118.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C6 H6 118.9 . . ?
C4 C6 C7 122.2(9) . . ?
C4 C6 H6 118.9 . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C21A C22A H22D 109.5 . . ?
C21A C22A H22E 109.5 . . ?
C21A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C15 C17 H17 118.7 . . ?
C18 C17 C15 122.7(9) . . ?
C18 C17 H17 118.7 . . ?
C21 C20 H20 118.3 . . ?
C21 C20 C18 123.3(9) . . ?
C18 C20 H20 118.3 . . ?
O3 N2 O4 112.3(7) . . ?
C3 C4 C5 121.6(9) . . ?
C6 C4 C3 117.6(9) . . ?
C6 C4 C5 120.8(9) . . ?
O3A N2A O4A 112.6(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C2A C3A H3A 118.7 . . ?
C2A C3A C4A 122.5(9) . . ?
C4A C3A H3A 118.7 . . ?
O1A N1A O2A 111.6(8) . . ?
C17 C18 C20 117.3(9) . . ?
C17 C18 C19 121.6(9) . . ?
C20 C18 C19 121.1(10) . . ?
C6A C4A C5A 120.7(9) . . ?
C3A C4A C6A 118.4(9) . . ?
C3A C4A C5A 121.0(9) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

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
_geom_hbond_publ_flag
C11A H11F O2 0.98 2.55 3.454(9) 153.2 3_565 yes
C13 H13B O3A 0.98 2.47 3.328(11) 145.9 3_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O1 N1 O2 -3.1(7) . . . . ?
Ni1 O4 N2 O3 -4.8(7) . . . . ?
Ni1 O2 N1 O1 3.1(7) . . . . ?
Ni1 N3 C9 C7 -90.6(9) . . . . ?
Ni1 N3 C9 C2 85.8(9) . . . . ?
Ni1 N3 C10 C12 4.4(9) . . . . ?
Ni1 N3 C10 C11 -176.7(7) . . . . ?
Ni1 O3 N2 O4 4.7(7) . . . . ?
Ni1 N4 C14 C15 83.3(9) . . . . ?
Ni1 N4 C14 C21 -93.7(9) . . . . ?
Ni1 N4 C12 C10 -8.8(9) . . . . ?
Ni1 N4 C12 C13 174.8(6) . . . . ?
Ni1A N4A C14A C15A 101.2(8) . . . . ?
Ni1A N4A C14A C21A -77.8(9) . . . . ?
Ni1A N4A C12A C10A -4.2(9) . . . . ?
Ni1A N4A C12A C13A 176.6(7) . . . . ?
Ni1A O1A N1A O2A 0.5(7) . . . . ?
Ni1A O4A N2A O3A -4.5(8) . . . . ?
Ni1A N3A C10A C12A 7.0(10) . . . . ?
Ni1A N3A C10A C11A -171.4(6) . . . . ?
Ni1A N3A C9A C7A -74.6(9) . . . . ?
Ni1A N3A C9A C2A 102.7(8) . . . . ?
Ni1A O3A N2A O4A 4.5(8) . . . . ?
Ni1A O2A N1A O1A -0.5(7) . . . . ?
N3 C9 C7 C8 -2.2(12) . . . . ?
N3 C9 C7 C6 177.8(7) . . . . ?
N3 C9 C2 C3 -178.0(8) . . . . ?
N3 C9 C2 C1 4.7(13) . . . . ?
N3 C10 C12 N4 3.0(11) . . . . ?
N3 C10 C12 C13 179.7(7) . . . . ?
N4A C14A C15A C17A -180.0(7) . . . . ?
N4A C14A C15A C16A -0.4(13) . . . . ?
N4A C14A C21A C20A -179.2(8) . . . . ?
N4A C14A C21A C22A 0.2(12) . . . . ?
N4 C14 C15 C17 -179.2(8) . . . . ?
N4 C14 C15 C16 2.3(12) . . . . ?
N4 C14 C21 C20 179.5(8) . . . . ?
N4 C14 C21 C22 -3.3(13) . . . . ?
N3A C10A C12A N4A -1.8(12) . . . . ?
N3A C10A C12A C13A 177.4(7) . . . . ?
N3A C9A C7A C6A -179.4(7) . . . . ?
N3A C9A C7A C8A 0.1(12) . . . . ?
N3A C9A C2A C1A -0.1(13) . . . . ?
N3A C9A C2A C3A -180.0(8) . . . . ?
C14 N4 C12 C10 178.0(7) . . . . ?
C14 N4 C12 C13 1.5(12) . . . . ?
C14 C15 C17 C18 0.9(13) . . . . ?
C14 C21 C20 C18 -1.5(14) . . . . ?
C9 N3 C10 C12 -171.7(7) . . . . ?
C9 N3 C10 C11 7.3(12) . . . . ?
C9 C7 C6 C4 -2.0(13) . . . . ?
C9 C2 C3 C4 2.8(14) . . . . ?
C10A N3A C9A C7A 114.9(9) . . . . ?
C10A N3A C9A C2A -67.8(11) . . . . ?
C14A N4A C12A C10A 177.6(7) . . . . ?
C14A N4A C12A C13A -1.6(12) . . . . ?
C14A C15A C17A C18A 0.1(13) . . . . ?
C14A C21A C20A C18A -1.8(13) . . . . ?
C9A N3A C10A C12A 178.2(7) . . . . ?
C9A N3A C10A C11A -0.2(13) . . . . ?
C9A C7A C6A C4A -1.2(13) . . . . ?
C9A C2A C3A C4A 0.0(14) . . . . ?
C15A C14A C21A C20A 1.9(13) . . . . ?
C15A C14A C21A C22A -178.7(8) . . . . ?
C12A N4A C14A C15A -80.9(10) . . . . ?
C12A N4A C14A C21A 100.1(10) . . . . ?
C10 N3 C9 C7 84.8(10) . . . . ?
C10 N3 C9 C2 -98.8(10) . . . . ?
C7A C9A C2A C1A 177.1(8) . . . . ?
C7A C9A C2A C3A -2.8(13) . . . . ?
C7A C6A C4A C3A -1.5(13) . . . . ?
C7A C6A C4A C5A 178.0(8) . . . . ?
C12 N4 C14 C15 -104.2(9) . . . . ?
C12 N4 C14 C21 78.8(10) . . . . ?
C7 C9 C2 C3 -1.8(13) . . . . ?
C7 C9 C2 C1 -179.0(8) . . . . ?
C7 C6 C4 C3 2.9(13) . . . . ?
C7 C6 C4 C5 -178.3(9) . . . . ?
C2 C9 C7 C8 -178.6(8) . . . . ?
C2 C9 C7 C6 1.4(13) . . . . ?
C2 C3 C4 C6 -3.3(14) . . . . ?
C2 C3 C4 C5 177.9(9) . . . . ?
C11 C10 C12 N4 -176.0(7) . . . . ?
C11 C10 C12 C13 0.6(11) . . . . ?
C8 C7 C6 C4 178.0(8) . . . . ?
C21A C14A C15A C17A -1.0(13) . . . . ?
C21A C14A C15A C16A 178.6(8) . . . . ?
C15 C14 C21 C20 2.6(13) . . . . ?
C15 C14 C21 C22 179.9(8) . . . . ?
C15 C17 C18 C20 0.2(14) . . . . ?
C15 C17 C18 C19 -177.7(9) . . . . ?
C11A C10A C12A N4A 176.7(7) . . . . ?
C11A C10A C12A C13A -4.1(12) . . . . ?
C21 C14 C15 C17 -2.3(12) . . . . ?
C21 C14 C15 C16 179.2(8) . . . . ?
C21 C20 C18 C17 0.2(14) . . . . ?
C21 C20 C18 C19 178.0(9) . . . . ?
C2A C9A C7A C6A 3.4(13) . . . . ?
C2A C9A C7A C8A -177.2(8) . . . . ?
C2A C3A C4A C6A 2.1(14) . . . . ?
C2A C3A C4A C5A -177.4(9) . . . . ?
C17A C18A C20A C21A 0.9(13) . . . . ?
C20A C18A C17A C15A 0.0(13) . . . . ?
C1 C2 C3 C4 -180.0(9) . . . . ?
C1A C2A C3A C4A -179.9(9) . . . . ?
C22A C21A C20A C18A 178.8(9) . . . . ?
C16 C15 C17 C18 179.4(9) . . . . ?
C8A C7A C6A C4A 179.3(8) . . . . ?
C22 C21 C20 C18 -178.8(9) . . . . ?
C16A C15A C17A C18A -179.5(9) . . . . ?
C19A C18A C17A C15A 178.1(8) . . . . ?
C19A C18A C20A C21A -177.3(9) . . . . ?

_olex2_date_sample_data_collection 2019-08-22
_olex2_date_sample_submission    2019-08-22
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.47(3)
2 0.53(3)

