 
data_k_sq
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H10 N2 Ni O4' 
_chemical_formula_weight          376.99

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'
 
_space_group_crystal_system       tetragonal
_space_group_IT_number            120
_space_group_name_H-M_alt         'I -4 c 2'
_space_group_name_Hall            'I -4 -2c'
 
_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'
 'y, -x, -z'
 '-y, x, -z'
 'x, -y, z+1/2'
 '-x, y, z+1/2'
 'y, x, -z+1/2'
 '-y, -x, -z+1/2'
 'x+1/2, y+1/2, z+1/2'
 '-x+1/2, -y+1/2, z+1/2'
 'y+1/2, -x+1/2, -z+1/2'
 '-y+1/2, x+1/2, -z+1/2'
 'x+1/2, -y+1/2, z+1'
 '-x+1/2, y+1/2, z+1'
 'y+1/2, x+1/2, -z+1'
 '-y+1/2, -x+1/2, -z+1'
 
_cell_length_a                    22.9846(9)
_cell_length_b                    22.9846(9)
_cell_length_c                    23.4908(12)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      12410.0(12)
_cell_formula_units_Z             16
_cell_measurement_temperature     158(2)
_cell_measurement_reflns_used     42219
_cell_measurement_theta_min       2.98
_cell_measurement_theta_max       25.33
 
_exptl_crystal_description        block
_exptl_crystal_colour             green
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     0.807          
_exptl_crystal_F_000              3072
_exptl_transmission_factor_min    0.6830  
_exptl_transmission_factor_max    0.7452
_exptl_crystal_size_max           0.140
_exptl_crystal_size_mid           0.130
_exptl_crystal_size_min           0.110
_exptl_absorpt_coefficient_mu     0.639
_shelx_estimated_absorpt_T_min    0.916
_shelx_estimated_absorpt_T_max    0.933
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    sadabs
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       158(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             31579
_diffrn_reflns_av_unetI/netI      0.0740
_diffrn_reflns_av_R_equivalents   0.1073
_diffrn_reflns_limit_h_min        -27
_diffrn_reflns_limit_h_max        26
_diffrn_reflns_limit_k_min        -25
_diffrn_reflns_limit_k_max        25
_diffrn_reflns_limit_l_min        -28
_diffrn_reflns_limit_l_max        28
_diffrn_reflns_theta_min          2.139
_diffrn_reflns_theta_max          25.319
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.994
_diffrn_measured_fraction_theta_full  0.994
_diffrn_reflns_Laue_measured_fraction_max    0.994
_diffrn_reflns_Laue_measured_fraction_full   0.994
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              5600
_reflns_number_gt                 4384
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.877
_reflns_Friedel_fraction_max      0.997
_reflns_Friedel_fraction_full     0.998
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1227P)²+15.9491P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    0.16(4)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          5600
_refine_ls_number_parameters      227
_refine_ls_number_restraints      98
_refine_ls_R_factor_all           0.0892
_refine_ls_R_factor_gt            0.0653
_refine_ls_wR_factor_ref          0.1952
_refine_ls_wR_factor_gt           0.1718
_refine_ls_goodness_of_fit_ref    1.036
_refine_ls_restrained_S_all       1.074
_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 0.62071(4) 0.30920(4) 0.90401(4) 0.0259(3) Uani 1 1 d . . . . .
O4 O 0.3677(2) 0.3114(2) 0.4946(2) 0.0341(13) Uani 1 1 d . . . . .
O2 O 0.6373(3) 0.3121(3) 0.6208(2) 0.0433(16) Uani 1 1 d . . . . .
O1 O 0.5982(3) 0.3935(3) 0.5943(3) 0.0573(18) Uani 1 1 d . . . . .
O3 O 0.4497(2) 0.2826(3) 0.4536(2) 0.0359(14) Uani 1 1 d . . . . .
N2 N 0.2681(3) 0.1644(3) 0.5987(3) 0.0374(15) Uani 1 1 d D U . . .
N1 N 0.5851(3) 0.3004(3) 0.8246(3) 0.0375(17) Uani 1 1 d D U . . .
C9 C 0.5358(3) 0.2920(4) 0.7139(3) 0.043(2) Uani 1 1 d D U . . .
C3 C 0.5032(4) 0.3140(4) 0.5577(4) 0.053(3) Uani 1 1 d . U . . .
H3 H 0.5196 0.3310 0.5245 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3694(3) 0.2310(4) 0.6006(4) 0.047(2) Uani 1 1 d D U . . .
C6 C 0.4532(3) 0.2677(4) 0.6524(4) 0.037(2) Uani 1 1 d . . . . .
H6 H 0.4351 0.2516 0.6852 0.044 Uiso 1 1 calc R U . . .
C7 C 0.5087(4) 0.2926(4) 0.6592(4) 0.042(2) Uani 1 1 d . . . . .
C5 C 0.4245(3) 0.2648(4) 0.6042(4) 0.046(2) Uani 1 1 d . . . . .
C8 C 0.4204(4) 0.2943(4) 0.4976(3) 0.039(2) Uani 1 1 d . . . . .
C2 C 0.5344(4) 0.3150(5) 0.6089(4) 0.053(3) Uani 1 1 d . . . . .
C4 C 0.4500(4) 0.2889(5) 0.5549(3) 0.051(3) Uani 1 1 d . . . . .
C1 C 0.5936(4) 0.3411(4) 0.6075(3) 0.041(2) Uani 1 1 d . . . . .
C16 C 0.2720(4) 0.2115(4) 0.6305(4) 0.078(3) Uani 1 1 d D U . . .
H16 H 0.2393 0.2223 0.6528 0.094 Uiso 1 1 calc R U . . .
C15 C 0.3213(4) 0.2465(5) 0.6334(5) 0.081(3) Uani 1 1 d D U . . .
H15 H 0.3222 0.2800 0.6570 0.097 Uiso 1 1 calc R U . . .
C18 C 0.3133(4) 0.1484(5) 0.5667(5) 0.078(3) Uani 1 1 d D U . . .
H18 H 0.3106 0.1146 0.5436 0.093 Uiso 1 1 calc R U . . .
C17 C 0.3647(5) 0.1810(5) 0.5669(5) 0.086(4) Uani 1 1 d D U . . .
H17 H 0.3966 0.1691 0.5440 0.104 Uiso 1 1 calc R U . . .
C12 C 0.5046(5) 0.3157(4) 0.7570(4) 0.078(3) Uani 1 1 d D U . . .
H12 H 0.4663 0.3297 0.7508 0.093 Uiso 1 1 calc R U . . .
C10 C 0.5928(4) 0.2705(4) 0.7237(4) 0.076(3) Uani 1 1 d D U . . .
H10 H 0.6153 0.2534 0.6943 0.091 Uiso 1 1 calc R U . . .
C13 C 0.5306(4) 0.3191(4) 0.8113(4) 0.074(3) Uani 1 1 d D U . . .
H13 H 0.5081 0.3359 0.8411 0.089 Uiso 1 1 calc R U . . .
C11 C 0.6141(4) 0.2761(4) 0.7804(4) 0.069(3) Uani 1 1 d D U . . .
H11 H 0.6520 0.2615 0.7878 0.082 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 2.041(6) 11_556 ?
Ni1 N1 2.047(7) . ?
Ni1 O2 2.058(6) 8_666 ?
Ni1 O3 2.086(5) 6_655 ?
Ni1 O4 2.146(5) 6_655 ?
Ni1 O1 2.155(6) 8_666 ?
Ni1 C1 2.416(8) 8_666 ?
Ni1 C8 2.418(7) 6_655 ?
O4 C8 1.278(10) . ?
O4 Ni1 2.146(5) 6_654 ?
O2 C1 1.245(11) . ?
O2 Ni1 2.058(6) 8_666 ?
O1 C1 1.248(11) . ?
O1 Ni1 2.155(6) 8_666 ?
O3 C8 1.261(10) . ?
O3 Ni1 2.086(5) 6_654 ?
N2 C16 1.319(10) . ?
N2 C18 1.335(10) . ?
N2 Ni1 2.041(6) 12_546 ?
N1 C11 1.355(10) . ?
N1 C13 1.362(10) . ?
C9 C12 1.355(10) . ?
C9 C10 1.418(10) . ?
C9 C7 1.428(11) . ?
C3 C4 1.354(14) . ?
C3 C2 1.400(13) . ?
C3 H3 0.9500 . ?
C14 C15 1.393(10) . ?
C14 C17 1.400(11) . ?
C14 C5 1.488(11) . ?
C6 C5 1.312(12) . ?
C6 C7 1.408(12) . ?
C6 H6 0.9500 . ?
C7 C2 1.419(12) . ?
C5 C4 1.411(11) . ?
C8 C4 1.512(11) . ?
C8 Ni1 2.418(7) 6_654 ?
C2 C1 1.487(12) . ?
C1 Ni1 2.416(8) 8_666 ?
C16 C15 1.390(11) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C18 C17 1.397(11) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C12 C13 1.411(10) . ?
C12 H12 0.9500 . ?
C10 C11 1.424(10) . ?
C10 H10 0.9500 . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
N2 Ni1 N1 94.7(3) 11_556 . ?
N2 Ni1 O2 98.2(2) 11_556 8_666 ?
N1 Ni1 O2 95.8(3) . 8_666 ?
N2 Ni1 O3 98.3(2) 11_556 6_655 ?
N1 Ni1 O3 99.8(2) . 6_655 ?
O2 Ni1 O3 156.3(2) 8_666 6_655 ?
N2 Ni1 O4 89.4(2) 11_556 6_655 ?
N1 Ni1 O4 162.9(2) . 6_655 ?
O2 Ni1 O4 100.0(2) 8_666 6_655 ?
O3 Ni1 O4 63.2(2) 6_655 6_655 ?
N2 Ni1 O1 159.2(3) 11_556 8_666 ?
N1 Ni1 O1 93.1(3) . 8_666 ?
O2 Ni1 O1 61.9(3) 8_666 8_666 ?
O3 Ni1 O1 99.3(3) 6_655 8_666 ?
O4 Ni1 O1 88.7(3) 6_655 8_666 ?
N2 Ni1 C1 128.5(3) 11_556 8_666 ?
N1 Ni1 C1 97.8(3) . 8_666 ?
O2 Ni1 C1 31.0(3) 8_666 8_666 ?
O3 Ni1 C1 128.0(3) 6_655 8_666 ?
O4 Ni1 C1 92.5(2) 6_655 8_666 ?
O1 Ni1 C1 31.0(3) 8_666 8_666 ?
N2 Ni1 C8 95.6(3) 11_556 6_655 ?
N1 Ni1 C8 131.1(3) . 6_655 ?
O2 Ni1 C8 129.5(3) 8_666 6_655 ?
O3 Ni1 C8 31.4(3) 6_655 6_655 ?
O4 Ni1 C8 31.8(2) 6_655 6_655 ?
O1 Ni1 C8 93.7(3) 8_666 6_655 ?
C1 Ni1 C8 112.0(3) 8_666 6_655 ?
C8 O4 Ni1 85.9(4) . 6_654 ?
C1 O2 Ni1 90.6(5) . 8_666 ?
C1 O1 Ni1 86.1(5) . 8_666 ?
C8 O3 Ni1 88.9(5) . 6_654 ?
C16 N2 C18 119.4(8) . . ?
C16 N2 Ni1 118.9(5) . 12_546 ?
C18 N2 Ni1 121.6(6) . 12_546 ?
C11 N1 C13 114.1(8) . . ?
C11 N1 Ni1 122.9(6) . . ?
C13 N1 Ni1 123.1(6) . . ?
C12 C9 C10 120.4(7) . . ?
C12 C9 C7 115.9(8) . . ?
C10 C9 C7 123.6(8) . . ?
C4 C3 C2 120.8(8) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C15 C14 C17 117.4(9) . . ?
C15 C14 C5 120.6(8) . . ?
C17 C14 C5 121.9(8) . . ?
C5 C6 C7 125.0(8) . . ?
C5 C6 H6 117.5 . . ?
C7 C6 H6 117.5 . . ?
C6 C7 C2 115.6(8) . . ?
C6 C7 C9 119.6(7) . . ?
C2 C7 C9 124.8(8) . . ?
C6 C5 C4 118.7(8) . . ?
C6 C5 C14 120.1(8) . . ?
C4 C5 C14 120.8(8) . . ?
O3 C8 O4 121.8(7) . . ?
O3 C8 C4 118.1(8) . . ?
O4 C8 C4 120.1(7) . . ?
O3 C8 Ni1 59.6(4) . 6_654 ?
O4 C8 Ni1 62.3(4) . 6_654 ?
C4 C8 Ni1 175.1(7) . 6_654 ?
C3 C2 C7 119.7(8) . . ?
C3 C2 C1 117.2(8) . . ?
C7 C2 C1 123.1(8) . . ?
C3 C4 C5 120.2(8) . . ?
C3 C4 C8 114.4(7) . . ?
C5 C4 C8 125.2(8) . . ?
O2 C1 O1 120.7(8) . . ?
O2 C1 C2 121.1(8) . . ?
O1 C1 C2 118.1(8) . . ?
O2 C1 Ni1 58.4(4) . 8_666 ?
O1 C1 Ni1 62.8(4) . 8_666 ?
C2 C1 Ni1 174.3(7) . 8_666 ?
N2 C16 C15 123.9(9) . . ?
N2 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
C16 C15 C14 118.2(10) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
N2 C18 C17 120.6(10) . . ?
N2 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C17 C14 120.5(10) . . ?
C18 C17 H17 119.8 . . ?
C14 C17 H17 119.8 . . ?
C9 C12 C13 118.4(9) . . ?
C9 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C9 C10 C11 116.1(9) . . ?
C9 C10 H10 122.0 . . ?
C11 C10 H10 122.0 . . ?
N1 C13 C12 125.3(9) . . ?
N1 C13 H13 117.3 . . ?
C12 C13 H13 117.3 . . ?
N1 C11 C10 125.7(10) . . ?
N1 C11 H11 117.1 . . ?
C10 C11 H11 117.1 . . ?
 
_refine_diff_density_max    0.925
_refine_diff_density_min   -0.583
_refine_diff_density_rms    0.088




