# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_yuto_co_0m
_database_code_depnum_ccdc_archive 'CCDC 1892441'
loop_
_audit_author_name
_audit_author_address
'Mihaela Cibian'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-01-21 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
_vrf_PLAT480_yuto_co_0m          
;
PROBLEM: 
Long H...A H-Bond Reported H6A ..CL3 . 2.99 Ang.
Long H...A H-Bond Reported H9 ..CL2 . 2.97 Ang.

RESPONSE: 
indication of weak hydrogen bonding
;
_vrf_PLAT911_yuto_co_0m          
;
PROBLEM: 
Missing # FCF Refl Between THmin & STh/L= 0.600 13 Report

RESPONSE: 
overflow
;

_vrf_PLAT154_yuto_co_0m          
;
PROBLEM: 
The sus on the Cell Angles are Equal .......... 0.001 Degree

RESPONSE:
checked; the error values on the cell angles found in the *.P4P file
are 0.0011, 0.0011, and 0.0011 for alpha, beta and gamma, respectively. 
;

_vrf_PLAT232_yuto_co_0m          
;
PROBLEM: 
Hirshfeld Test Diff (M-X) Co1 -- N1 .. 6.3 su

RESPONSE:
bond involving the heaviest atom in the structure; relevant atomic
sites have been checked and they were found to be consistent with the
chemistry performed.
;

_vrf_PLAT605_yuto_co_0m          
;
PROBLEM: 
Largest Solvent Accessible VOID in the Structure .. 108 Ang3

RESPONSE:
Disordered co-crystallized solvent was removed using SQUEEZE routine 
(PLATON (Spek, 2009)) as implemented in OLEX2 (Dolomanov et al., 2009). 
As a result, an improvement of the R1 factor with 11.2 % was obtained. 
The presence of one co-crystallized methanol molecule or two 
co-crystallized water molecules can be estimated based on the 
calculated volume of accessible voids (119 Ang3 per unit cell) 
containing 38 electrons (Z=2). The insights obtained from the attempts 
to model the disordered solvent and the identity of the solvents used 
for crystallization (methanol/ diethylether) are also considered 
for supporting this estimation.
;

_vrf_PLAT868_yuto_co_0m          
;
PROBLEM: 
ALERTS Due to the Use of _smtbx_masks Suppressed

RESPONSE:
Disordered co-crystallized solvent was removed using SQUEEZE routine 
(PLATON (Spek, 2009)) as implemented in OLEX2 (Dolomanov et al., 2009). 
As a result, an improvement of the R1 factor with 11.2 % was obtained. 
The presence of one co-crystallized methanol molecule or two 
co-crystallized water molecules can be estimated based on the 
calculated volume of accessible void (119 Ang3 per unit cell) 
containing 38 electrons (Z=2). The insights obtained from the attempts 
to model the disordered solvent and the identity of the solvents used 
for crystallization (methanol/ diethylether) are also considered 
for supporting this estimation.
;
_audit_creation_date             2018-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 Cl2 Co N4, Cl'
_chemical_formula_sum            'C14 H16 Cl3 Co N4'
_chemical_formula_weight         405.59
_chemical_melting_point          ?
_exptl_crystal_recrystallization_method 
'slow diffusion of diethylether into a solution of the compound in methanol'
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'
Co Co 0.3494 0.9721 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1082(10)
_cell_length_b                   9.8312(10)
_cell_length_c                   9.9666(11)
_cell_angle_alpha                93.6550(10)
_cell_angle_beta                 98.8980(10)
_cell_angle_gamma                90.0060(10)
_cell_volume                     879.88(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7067
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.036
_cell_measurement_theta_min      2.264
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. 
wR2(int) was 0.0772 before and 0.0376 after correction. The Ratio 
of minimum to maximum transmission is 0.7914. The λ/2 correction 
factor is 0.00150.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker SMART APEX II Charged-Coupled Device (CCD) Area Detector 
diffractometer. The crystal-to-detector distance was 6.0 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10731
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.088
_diffrn_reflns_theta_min         2.073
_diffrn_ambient_temperature      100
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode with a mirror focussing unit'
_diffrn_source_target            ?
_diffrn_source_type              ?
_diffrn_standards_number         ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3861
_reflns_number_total             4301
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.066
_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)+(0.0528P)²+0.5539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0961
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.27110(3) 0.12484(2) 0.12962(2) 0.01749(9) Uani 1 1 d . . . . .
Cl1 Cl 0.19407(5) 0.12792(5) -0.09723(5) 0.02358(11) Uani 1 1 d . . . . .
C1 C 0.2347(2) 0.09844(19) 0.39776(19) 0.0192(4) Uani 1 1 d . . . . .
N1 N 0.33447(18) 0.12733(16) 0.31798(17) 0.0189(3) Uani 1 1 d . . . . .
Cl2 Cl 0.32774(5) -0.09802(4) 0.10952(5) 0.02181(11) Uani 1 1 d . . . . .
N2 N 0.47416(19) 0.19694(17) 0.12609(17) 0.0215(3) Uani 1 1 d . . . . .
H2 H 0.518(3) 0.150(3) 0.062(3) 0.029(7) Uiso 1 1 d . . . . .
C2 C 0.2725(2) 0.1136(2) 0.5375(2) 0.0225(4) Uani 1 1 d . . . . .
H2A H 0.202331 0.094023 0.595084 0.027 Uiso 1 1 calc R . . . .
N3 N 0.22100(19) 0.30912(16) 0.14751(16) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.4154(2) 0.1583(2) 0.5920(2) 0.0243(4) Uani 1 1 d . . . . .
H3 H 0.442766 0.171783 0.687872 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5185(2) 0.1833(2) 0.5070(2) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.617067 0.211704 0.543619 0.029 Uiso 1 1 calc R . . . .
N4 N 0.07213(18) 0.09261(17) 0.17840(17) 0.0203(3) Uani 1 1 d . . . . .
H4A H 0.022(3) 0.026(3) 0.128(3) 0.033(7) Uiso 1 1 d . . . . .
C5 C 0.4742(2) 0.16592(19) 0.3677(2) 0.0204(4) Uani 1 1 d . . . . .
C6 C 0.5705(2) 0.1760(2) 0.2593(2) 0.0246(4) Uani 1 1 d . . . . .
H6A H 0.641230 0.253330 0.283664 0.030 Uiso 1 1 calc R . . . .
H6B H 0.628355 0.091359 0.251679 0.030 Uiso 1 1 calc R . . . .
C7 C 0.4630(2) 0.3440(2) 0.0944(2) 0.0252(4) Uani 1 1 d . . . . .
H7A H 0.459635 0.351919 -0.004498 0.030 Uiso 1 1 calc R . . . .
H7B H 0.551291 0.394937 0.142854 0.030 Uiso 1 1 calc R . . . .
C8 C 0.3246(2) 0.4030(2) 0.1384(2) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.2933(3) 0.5401(2) 0.1585(2) 0.0287(4) Uani 1 1 d . . . . .
H9 H 0.366664 0.608015 0.155561 0.034 Uiso 1 1 calc R . . . .
C10 C 0.1518(3) 0.5755(2) 0.1832(2) 0.0318(5) Uani 1 1 d . . . . .
H10 H 0.127985 0.668885 0.197410 0.038 Uiso 1 1 calc R . . . .
C11 C 0.0449(3) 0.4761(2) 0.1872(2) 0.0281(4) Uani 1 1 d . . . . .
H11 H -0.052516 0.500390 0.201973 0.034 Uiso 1 1 calc R . . . .
C12 C 0.0833(2) 0.3411(2) 0.16924(19) 0.0224(4) Uani 1 1 d . . . . .
C13 C -0.0178(2) 0.2201(2) 0.1642(2) 0.0242(4) Uani 1 1 d . . . . .
H13A H -0.086414 0.213656 0.076698 0.029 Uiso 1 1 calc R . . . .
H13B H -0.077930 0.230917 0.238817 0.029 Uiso 1 1 calc R . . . .
C14 C 0.0912(2) 0.0431(2) 0.31951(19) 0.0212(4) Uani 1 1 d . . . . .
H14A H 0.007342 0.074284 0.365714 0.025 Uiso 1 1 calc R . . . .
H14B H 0.092143 -0.057773 0.314897 0.025 Uiso 1 1 calc R . . . .
Cl3 Cl 0.09984(6) 0.73551(5) 0.49171(6) 0.03087(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 Cl1 2.2634(6) . ?
Co1 N1 1.8754(17) . ?
Co1 Cl2 2.2546(5) . ?
Co1 N2 1.9868(17) . ?
Co1 N3 1.8726(17) . ?
Co1 N4 1.9782(16) . ?
C1 N1 1.338(2) . ?
C1 C2 1.380(3) . ?
C1 C14 1.498(3) . ?
N1 C5 1.338(2) . ?
N2 H2 0.90(3) . ?
N2 C6 1.500(3) . ?
N2 C7 1.499(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.391(3) . ?
N3 C8 1.337(2) . ?
N3 C12 1.340(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
N4 H4A 0.88(3) . ?
N4 C13 1.500(3) . ?
N4 C14 1.502(2) . ?
C5 C6 1.501(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.502(3) . ?
C8 C9 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 C13 1.497(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 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 Co1 Cl1 178.48(5) . . ?
N1 Co1 Cl2 90.02(5) . . ?
N1 Co1 N2 83.84(7) . . ?
N1 Co1 N4 84.14(7) . . ?
Cl2 Co1 Cl1 91.484(19) . . ?
N2 Co1 Cl1 95.76(5) . . ?
N2 Co1 Cl2 96.76(5) . . ?
N3 Co1 Cl1 88.75(5) . . ?
N3 Co1 N1 89.76(7) . . ?
N3 Co1 Cl2 178.98(5) . . ?
N3 Co1 N2 84.20(7) . . ?
N3 Co1 N4 84.24(7) . . ?
N4 Co1 Cl1 95.96(5) . . ?
N4 Co1 Cl2 94.75(5) . . ?
N4 Co1 N2 163.32(7) . . ?
N1 C1 C2 120.01(18) . . ?
N1 C1 C14 113.11(16) . . ?
C2 C1 C14 126.77(17) . . ?
C1 N1 Co1 118.23(13) . . ?
C5 N1 Co1 118.94(13) . . ?
C5 N1 C1 122.69(17) . . ?
Co1 N2 H2 111.1(17) . . ?
C6 N2 Co1 109.49(12) . . ?
C6 N2 H2 105.8(17) . . ?
C7 N2 Co1 108.69(13) . . ?
C7 N2 H2 109.0(17) . . ?
C7 N2 C6 112.73(16) . . ?
C1 C2 H2A 120.7 . . ?
C1 C2 C3 118.52(18) . . ?
C3 C2 H2A 120.7 . . ?
C8 N3 Co1 118.47(14) . . ?
C8 N3 C12 122.92(18) . . ?
C12 N3 Co1 118.62(13) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.34(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.43(18) . . ?
C5 C4 H4 120.8 . . ?
Co1 N4 H4A 113.2(18) . . ?
C13 N4 Co1 109.67(12) . . ?
C13 N4 H4A 108.2(18) . . ?
C13 N4 C14 113.16(15) . . ?
C14 N4 Co1 108.60(12) . . ?
C14 N4 H4A 104.0(18) . . ?
N1 C5 C4 119.93(18) . . ?
N1 C5 C6 113.08(17) . . ?
C4 C5 C6 126.84(18) . . ?
N2 C6 C5 109.21(16) . . ?
N2 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
N2 C7 C8 109.37(16) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
N3 C8 C7 113.37(17) . . ?
N3 C8 C9 119.75(19) . . ?
C9 C8 C7 126.68(18) . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.3(2) . . ?
C10 C9 H9 120.9 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H11 120.7 . . ?
N3 C12 C11 119.76(19) . . ?
N3 C12 C13 113.79(17) . . ?
C11 C12 C13 126.37(19) . . ?
N4 C13 H13A 109.7 . . ?
N4 C13 H13B 109.7 . . ?
C12 C13 N4 109.87(16) . . ?
C12 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C1 C14 N4 108.91(15) . . ?
C1 C14 H14A 109.9 . . ?
C1 C14 H14B 109.9 . . ?
N4 C14 H14A 109.9 . . ?
N4 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?

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
N2 H2 Cl2 0.90(3) 2.41(3) 3.2765(18) 161(2) 2_655 yes
C4 H4 Cl3 0.95 2.71 3.564(2) 149.9 2_666 yes
N4 H4A Cl1 0.88(3) 2.46(3) 3.2252(17) 146(2) 2 yes
C6 H6A Cl3 0.99 2.99 3.654(2) 125.6 2_666 yes
C9 H9 Cl2 0.95 2.97 3.642(2) 129.1 1_565 yes
C13 H13A Cl2 0.99 2.83 3.749(2) 153.8 2 yes
C13 H13B Cl3 0.99 2.72 3.621(2) 151.0 2_566 yes
C14 H14A Cl3 0.99 2.56 3.434(2) 147.1 2_566 yes
C14 H14B Cl3 0.99 2.77 3.566(2) 138.1 1_545 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
Co1 N1 C5 C4 172.73(14) . . . . ?
Co1 N1 C5 C6 -11.4(2) . . . . ?
Co1 N2 C6 C5 -24.22(19) . . . . ?
Co1 N2 C7 C8 25.73(19) . . . . ?
Co1 N3 C8 C7 8.3(2) . . . . ?
Co1 N3 C8 C9 -176.52(15) . . . . ?
Co1 N3 C12 C11 177.91(15) . . . . ?
Co1 N3 C12 C13 -5.0(2) . . . . ?
Co1 N4 C13 C12 -20.91(19) . . . . ?
Co1 N4 C14 C1 27.83(18) . . . . ?
Cl1 Co1 N3 C8 -90.14(14) . . . . ?
Cl1 Co1 N3 C12 90.04(14) . . . . ?
C1 N1 C5 C4 -3.0(3) . . . . ?
C1 N1 C5 C6 172.88(17) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
N1 Co1 N3 C8 89.61(15) . . . . ?
N1 Co1 N3 C12 -90.21(15) . . . . ?
N1 C1 C2 C3 -0.4(3) . . . . ?
N1 C1 C14 N4 -25.3(2) . . . . ?
N1 C5 C6 N2 23.3(2) . . . . ?
Cl2 Co1 N1 C1 -89.78(14) . . . . ?
Cl2 Co1 N1 C5 94.34(14) . . . . ?
N2 Co1 N1 C1 173.42(15) . . . . ?
N2 Co1 N1 C5 -2.46(14) . . . . ?
N2 Co1 N3 C8 5.78(15) . . . . ?
N2 Co1 N3 C12 -174.04(15) . . . . ?
N2 C7 C8 N3 -22.6(2) . . . . ?
N2 C7 C8 C9 162.6(2) . . . . ?
C2 C1 N1 Co1 -172.91(14) . . . . ?
C2 C1 N1 C5 2.8(3) . . . . ?
C2 C1 C14 N4 158.40(19) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
N3 Co1 N1 C1 89.23(14) . . . . ?
N3 Co1 N1 C5 -86.65(15) . . . . ?
N3 C8 C9 C10 -2.2(3) . . . . ?
N3 C12 C13 N4 17.2(2) . . . . ?
C3 C4 C5 N1 0.7(3) . . . . ?
C3 C4 C5 C6 -174.49(19) . . . . ?
C4 C5 C6 N2 -161.20(19) . . . . ?
N4 Co1 N1 C1 5.00(14) . . . . ?
N4 Co1 N1 C5 -170.89(15) . . . . ?
N4 Co1 N3 C8 173.75(15) . . . . ?
N4 Co1 N3 C12 -6.07(15) . . . . ?
C6 N2 C7 C8 -95.84(19) . . . . ?
C7 N2 C6 C5 96.90(19) . . . . ?
C7 C8 C9 C10 172.3(2) . . . . ?
C8 N3 C12 C11 -1.9(3) . . . . ?
C8 N3 C12 C13 175.17(17) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C10 C11 C12 N3 -0.5(3) . . . . ?
C10 C11 C12 C13 -177.2(2) . . . . ?
C11 C12 C13 N4 -165.92(19) . . . . ?
C12 N3 C8 C7 -171.90(18) . . . . ?
C12 N3 C8 C9 3.3(3) . . . . ?
C13 N4 C14 C1 -94.18(18) . . . . ?
C14 C1 N1 Co1 10.6(2) . . . . ?
C14 C1 N1 C5 -173.73(17) . . . . ?
C14 C1 C2 C3 175.60(19) . . . . ?
C14 N4 C13 C12 100.50(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.500 0.500 119.2 37.9 ?

_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_yuto_znh_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1892444'
loop_
_audit_author_name
_audit_author_address
'Mihaela Cibian'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-01-21 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
_vrf_PLAT094_yuto_znh_2_0m       
;
PROBLEM: 
Ratio of Maximum / Minimum Residual Density .... 2.88 Report

RESPONSE: 
checked; the highest residual electron density peak (0.86 eA-3) 
is localized 1.68 A from H2 and do not make chemical sense; it is 
most likely due to twinning present in the structure (see comment 
to the PLAT083 alert below).
;
_vrf_PLAT480_yuto_znh_2_0m       
;
PROBLEM: 
Long H...A H-Bond Reported H2 ..CL1 . 2.98 Ang.


RESPONSE: 
indication of week hydrogen bonding
;
_vrf_PLAT905_yuto_znh_2_0m       
;
PROBLEM: 
Negative K value in the Analysis of Variance ... -0.408 Report

RESPONSE: 
checked; the place for the negative value of K is only in the 
lowest-intensity bin in the table, being most probably due to 
non optimal background treatment. All the other K values are 
close to 1 (as expected).  
;
_vrf_PLAT083_yuto_znh_2_0m       
;
PROBLEM: 
SHELXL Second Parameter in WGHT Unusually Large 7.77 Why ?

RESPONSE: 
no twin law was detected with TwinRotMat routine from 
PLATON (Spek, 2009); however twinning was identified upon 
inspection of the diffraction pattern in RLATT (Bruker, 2013); 
treatment for non-merohedrally twinned crystal data was performed 
using CELL_NOW (2 domains)/ TWINABS/ BASF / HKLF5 (Bruker 2014), 
but the models obtained were worse than the present model and 
therefore the twinning treatment was not retained.    
;
_vrf_PLAT605_yuto_znh_2_0m       
;
PROBLEM: 
Largest Solvent Accessible VOID in the Structure 183 A**3

RESPONSE:
Disordered co-crystallized solvent was removed using SQUEEZE routine 
(PLATON (Spek, 2009)) as implemented in OLEX2 (Dolomanov et al., 2009). 
As a result, an improvement of the R1 factor with 6.2 % was obtained. 
It can be estimated that one methanol molecule or 1.5 water molecules 
could fit. This estimation is based on calculated solvent accessible 
voids of 1600 A3 per unit cell, containing 260 electrons (Z = 16), 
as well as on the insights obtained from the attempts to model the 
disordered solvent and the identity of the solvents used for 
crystallization (methanol/ diethylether).
;

_vrf_PLAT868_yuto_znh_2_0m       
;
PROBLEM: 
ALERTS Due to the Use of _smtbx_masks Suppressed

RESPONSE:
Disordered co-crystallized solvent was removed using SQUEEZE routine 
(PLATON (Spek, 2009)) as implemented in OLEX2 (Dolomanov et al., 2009). 
As a result, an improvement of the R1 factor with 6.2 % was obtained. 
It can be estimated that one methanol molecule or 1.5 water molecules 
could fit. This estimation is based on calculated solvent accessible 
voids of 1600 A3 per unit cell, containing 260 electrons (Z = 16), 
as well as on the insights obtained from the attempts to model the 
disordered solvent and the identity of the solvents used for 
crystallization (methanol/ diethylether).
;
_audit_creation_date             2018-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 Cl2 N4 Zn'
_chemical_formula_sum            'C14 H16 Cl2 N4 Zn'
_chemical_formula_weight         376.58
_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'
Zn Zn 0.2839 1.4301 '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           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   8.6064(12)
_cell_length_b                   28.201(4)
_cell_length_c                   29.216(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7090.8(17)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    6380
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.404
_cell_measurement_theta_min      2.571
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    1.685
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.1926 before and 0.0549 after correction. The Ratio 
of minimum to maximum transmission is 0.7567. The λ/2 correction 
factor is 0.00150.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3072
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal 
sample, which was mounted on a loop fiber. Data were collected using 
a Bruker SMART APEX II Charged-Coupled Device (CCD) Area Detector 
diffractometer. The crystal-to-detector distance was 6.0 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            19628
_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         27.474
_diffrn_reflns_theta_min         2.007
_diffrn_ambient_temperature      100
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode with a mirror focussing unit'
_diffrn_source_target            ?
_diffrn_source_type              ?
_diffrn_standards_number         ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1633
_reflns_number_total             2041
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+7.7733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.875000 0.375000 0.57218(2) 0.02599(12) Uani 1 2 d S T P . .
Cl1 Cl 0.86820(6) 0.31342(2) 0.62817(2) 0.03133(14) Uani 1 1 d . . . . .
N1 N 0.89547(18) 0.42360(6) 0.51678(5) 0.0263(3) Uani 1 1 d . . . . .
N2 N 0.62556(19) 0.38514(6) 0.54827(6) 0.0275(4) Uani 1 1 d . . . . .
H2 H 0.567(2) 0.3866(7) 0.5725(7) 0.018(5) Uiso 1 1 d . . . . .
C1 C 1.0327(2) 0.42865(7) 0.49592(7) 0.0300(4) Uani 1 1 d . . . . .
C2 C 1.0458(3) 0.45529(8) 0.45627(7) 0.0366(5) Uani 1 1 d . . . . .
H2A H 1.143587 0.459153 0.441666 0.044 Uiso 1 1 calc R . . . .
C3 C 0.9136(3) 0.47618(8) 0.43834(7) 0.0375(5) Uani 1 1 d . . . . .
H3 H 0.920516 0.495795 0.411982 0.045 Uiso 1 1 calc R . . . .
C4 C 0.7709(3) 0.46829(7) 0.45913(7) 0.0351(5) Uani 1 1 d . . . . .
H4 H 0.678208 0.480919 0.446369 0.042 Uiso 1 1 calc R . . . .
C5 C 0.7667(2) 0.44169(7) 0.49876(7) 0.0297(4) Uani 1 1 d . . . . .
C6 C 0.6201(2) 0.43176(8) 0.52551(7) 0.0326(5) Uani 1 1 d . . . . .
H6A H 0.605572 0.456811 0.548860 0.039 Uiso 1 1 calc R . . . .
H6B H 0.529842 0.432745 0.504521 0.039 Uiso 1 1 calc R . . . .
C7 C 0.5804(2) 0.34529(8) 0.51882(7) 0.0324(5) Uani 1 1 d . . . . .
H7A H 0.508292 0.356976 0.494935 0.039 Uiso 1 1 calc R . . . .
H7B H 0.523849 0.321589 0.537465 0.039 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 Cl1 2.3864(6) . ?
Zn1 Cl1 2.3864(6) 2_655 ?
Zn1 N1 2.1283(16) 2_655 ?
Zn1 N1 2.1282(16) . ?
Zn1 N2 2.2756(17) 2_655 ?
Zn1 N2 2.2756(16) . ?
N1 C1 1.337(2) . ?
N1 C5 1.329(2) . ?
N2 H2 0.87(2) . ?
N2 C6 1.474(3) . ?
N2 C7 1.468(3) . ?
C1 C2 1.385(3) . ?
C1 C7 1.514(3) 2_655 ?
C2 H2A 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 C6 1.511(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 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
Cl1 Zn1 Cl1 93.46(3) . 2_655 ?
N1 Zn1 Cl1 92.90(5) . 2_655 ?
N1 Zn1 Cl1 172.74(5) 2_655 2_655 ?
N1 Zn1 Cl1 172.74(5) . . ?
N1 Zn1 Cl1 92.90(5) 2_655 . ?
N1 Zn1 N1 80.97(9) . 2_655 ?
N1 Zn1 N2 76.67(6) . 2_655 ?
N1 Zn1 N2 76.67(6) 2_655 . ?
N1 Zn1 N2 76.33(6) 2_655 2_655 ?
N1 Zn1 N2 76.33(6) . . ?
N2 Zn1 Cl1 106.18(4) 2_655 2_655 ?
N2 Zn1 Cl1 98.17(5) 2_655 . ?
N2 Zn1 Cl1 98.17(5) . 2_655 ?
N2 Zn1 Cl1 106.18(4) . . ?
N2 Zn1 N2 144.25(9) . 2_655 ?
C1 N1 Zn1 119.23(13) . . ?
C5 N1 Zn1 118.66(13) . . ?
C5 N1 C1 121.03(17) . . ?
Zn1 N2 H2 107.9(13) . . ?
C6 N2 Zn1 106.30(11) . . ?
C6 N2 H2 107.7(13) . . ?
C7 N2 Zn1 109.50(12) . . ?
C7 N2 H2 111.0(13) . . ?
C7 N2 C6 114.19(17) . . ?
N1 C1 C2 120.70(19) . . ?
N1 C1 C7 116.03(17) . 2_655 ?
C2 C1 C7 123.26(18) . 2_655 ?
C1 C2 H2A 120.6 . . ?
C3 C2 C1 118.74(19) . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.56(19) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.52(19) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.29(19) . . ?
N1 C5 C6 114.86(17) . . ?
C4 C5 C6 123.83(18) . . ?
N2 C6 C5 111.84(16) . . ?
N2 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C1 113.22(16) . 2_655 ?
N2 C7 H7A 108.9 . . ?
N2 C7 H7B 108.9 . . ?
C1 C7 H7A 108.9 2_655 . ?
C1 C7 H7B 108.9 2_655 . ?
H7A C7 H7B 107.7 . . ?

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
N2 H2 Cl1 0.87(2) 2.64(2) 3.4101(18) 147.7(16) 12_455 yes
N2 H2 Cl1 0.87(2) 2.98(2) 3.6209(18) 132.1(15) 11 yes
C7 H7B Cl1 0.99 2.76 3.576(2) 139.9 11 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
Zn1 N1 C1 C2 171.79(15) . . . . ?
Zn1 N1 C1 C7 -9.6(2) . . . 2_655 ?
Zn1 N1 C5 C4 -171.29(15) . . . . ?
Zn1 N1 C5 C6 10.1(2) . . . . ?
Zn1 N2 C6 C5 37.11(19) . . . . ?
Zn1 N2 C7 C1 -24.8(2) . . . 2_655 ?
N1 C1 C2 C3 -0.7(3) . . . . ?
N1 C5 C6 N2 -33.2(2) . . . . ?
C1 N1 C5 C4 -3.2(3) . . . . ?
C1 N1 C5 C6 178.17(18) . . . . ?
C1 C2 C3 C4 -2.9(3) . . . . ?
C2 C3 C4 C5 3.4(3) . . . . ?
C3 C4 C5 N1 -0.4(3) . . . . ?
C3 C4 C5 C6 178.0(2) . . . . ?
C4 C5 C6 N2 148.2(2) . . . . ?
C5 N1 C1 C2 3.8(3) . . . . ?
C5 N1 C1 C7 -177.54(18) . . . 2_655 ?
C6 N2 C7 C1 94.2(2) . . . 2_655 ?
C7 N2 C6 C5 -83.7(2) . . . . ?
C7 C1 C2 C3 -179.3(2) 2_655 . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.901 -0.125 0.375 200.0 32.8 ?
2 -0.859 0.125 0.625 200.0 31.7 ?
3 0.124 0.125 0.125 200.0 31.7 ?
4 -0.539 0.375 0.875 200.0 32.8 ?
5 0.105 0.375 0.375 200.0 32.8 ?
6 -0.541 0.625 0.125 200.0 31.7 ?
7 0.124 0.625 0.625 200.0 31.7 ?
8 0.105 0.875 0.875 200.0 32.8 ?

_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_yuto_feh_3_0m
_database_code_depnum_ccdc_archive 'CCDC 1892442'
loop_
_audit_author_name
_audit_author_address
'Mihaela Cibian'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-01-21 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
_vrf_PLAT094_yuto_feh_3_0m       
;
PROBLEM: 
Ratio of Maximum / Minimum Residual Density .... 2.33 Report

RESPONSE: 
checked; the four highest residual electron density peaks (0.93, 0.78, 0.75, 
0.71 eA-3) do not make chemical sense; they are localized on the bonds 
involving the Fe atoms, the heaviest atoms in the structure and they 
can therefore be attributed to Fourier transform truncation errors.
;
_vrf_PLAT341_yuto_feh_3_0m       
;
PROBLEM: 
Low Bond Precision on C-C Bonds ............... 0.00608 Ang

RESPONSE: 
mediocre overall quality of the data set as result of the poor quality 
of the crystal
;
_vrf_PLAT420_yuto_feh_3_0m       
;
PROBLEM: 
D-H Without Acceptor N6 --H6 ... Please Check

RESPONSE: 
checked; the H6 atom (from the secondary amine group -(N6H6)-) is 
not implicated in H bonding in the structure obtained after applying 
the SQUEEZE routine (PLATON (Spek, 2009)) (see comment to PLAT606 alert below); 
the attempts to model the disordered solvent (before applying the SQUEEZE 
routine) indicate that the H6 atom might be implicated in H bonding with 
the O atom of one of the squeezed disordered methanol molecules.  
;
_vrf_PLAT480_yuto_feh_3_0m       
;
PROBLEM: 
Long H...A H-Bond Reported H4A ..CL4 . 2.87 Ang.
Long H...A H-Bond Reported H9 ..CL1 . 2.94 Ang.
Long H...A H-Bond Reported H11 ..CL1 . 2.85 Ang.
Long H...A H-Bond Reported H18 ..CL4 . 2.96 Ang.

RESPONSE: 
indication of week hydrogen bonding
;
_vrf_PLAT906_yuto_feh_3_0m       
;
PROBLEM: 
Large K Value in the Analysis of Variance ...... 3.343 Check

RESPONSE: 
checked; the place for the high values of K is in the lowest-intensity 
bin in the table; the large K value is most probably due to overestimated Fo, 
as most of area detector integration programs are slightly underestimating 
the background; thus the high value of Fo/Fc; this is most obvious in the 
weakest intensities, since the small addition to Fo becomes insignificant 
in the ratio when Fo is large.  
;
_vrf_PLAT911_yuto_feh_3_0m       
;
PROBLEM: 
Missing # FCF Refl Between THmin & STh/L= 0.600 13 Report

RESPONSE: 
overflow
;
_vrf_PLAT975_yuto_feh_3_0m       
;
PROBLEM: 
Check Calcd Resid. Dens. 0.76A From O1 0.40 eA-3

RESPONSE: 
checked; the residual electron density peak does not make chemical sense 
and it is localized on a bond involving the O1 atom and the Fe1 atom, 
the heaviest atom in the structure; it can therefore be attributed to 
Fourier transform truncation errors.
;
_vrf_PLAT154_yuto_feh_3_0m       
;
PROBLEM: 
The sus on the Cell Angles are Equal .......... 0.002 Degree

RESPONSE:
checked; the error values on the cell angles found in the *.P4P file
are 0.0019, 0.0018, and 0.0019 for alpha, beta and gamma, respectively. 
;

_vrf_PLAT606_yuto_feh_3_0m       
;
PROBLEM: 
VERY LARGE Solvent Accessible VOID(S) in Structure

RESPONSE:
Disordered co-crystallized solvent was removed using SQUEEZE routine 
(PLATON (Spek, 2009)) as implemented in OLEX2 (Dolomanov et al., 2009). 
As a result, an improvement of the R1 factor with 9.6 % was obtained. 
The presence of three co-crystallized methanol molecules is estimated based 
on the volumes of the accessible voids (472 Ang3 per unit cell), 
the corresponding calculated number of electrons (108 electrons) (Z=2), 
the insights obtained from the attempts to model the disordered solvent, 
and the identity of crystallization solvents (methanol/ diethylether).
;

_vrf_PLAT868_yuto_feh_3_0m       
;
PROBLEM: 
ALERTS Due to the Use of _smtbx_masks Suppressed

RESPONSE:
Disordered co-crystallized solvent was removed using SQUEEZE routine 
(PLATON (Spek, 2009)) as implemented in OLEX2 (Dolomanov et al., 2009). 
As a result, an improvement of the R1 factor with 9.6 % was obtained. 
The presence of three co-crystallized methanol molecules is estimated based 
on the volumes of the accessible voids (472 Ang3 per unit cell), 
the corresponding calculated number of electrons (108 electrons) (Z=2), 
the insights obtained from the attempts to model the disordered solvent, 
and the identity of crystallization solvents (methanol/ diethylether).
;
_audit_creation_date             2018-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H32 Cl2 Fe2 N8 O, 2(Cl)'
_chemical_formula_sum            'C28 H32 Cl4 Fe2 N8 O'
_chemical_formula_weight         750.11
_chemical_melting_point          ?
_exptl_crystal_recrystallization_method 
'slow diffusion of diethylether into a solution of the compound in methanol'
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'
Fe Fe 0.3463 0.8444 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1131(16)
_cell_length_b                   11.477(2)
_cell_length_c                   18.784(3)
_cell_angle_alpha                98.812(2)
_cell_angle_beta                 92.127(2)
_cell_angle_gamma                91.893(2)
_cell_volume                     1938.6(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8331
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.111
_cell_measurement_theta_min      2.238
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. 
wR2(int) was 0.0805 before and 0.0503 after correction. The Ratio 
of minimum to maximum transmission is 0.7501. The λ/2 correction 
factor is 0.00150.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker SMART APEX II Charged-Coupled Device (CCD) Area Detector 
diffractometer. The crystal-to-detector distance was 6.0 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22027
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.170
_diffrn_reflns_theta_min         1.098
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode with a mirror focussing unit'
_diffrn_standards_number         ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6793
_reflns_number_total             8518
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         8518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.058
_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)+(0.0765P)²+3.2975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1645
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C13(H13A,H13B), C14(H14A,H14B), C20(H20A,H20B),
 C21(H21A,H21B), C27(H27A,H27B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4A), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17),
 C18(H18), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.25286(5) 0.41906(5) 0.34116(3) 0.02784(15) Uani 1 1 d . . . . .
Fe2 Fe 0.21143(5) 0.18913(5) 0.19620(3) 0.02787(15) Uani 1 1 d . . . . .
Cl1 Cl 0.21799(10) 0.31904(9) 0.43852(5) 0.0352(2) Uani 1 1 d . . . . .
Cl2 Cl 0.15022(12) 0.31484(9) 0.11640(6) 0.0421(2) Uani 1 1 d . . . . .
O1 O 0.2654(3) 0.2956(3) 0.27232(15) 0.0369(6) Uani 1 1 d . . . . .
N1 N 0.2581(3) 0.5422(3) 0.26747(17) 0.0309(7) Uani 1 1 d . . . . .
N2 N 0.0274(3) 0.4841(3) 0.33956(17) 0.0298(7) Uani 1 1 d . . . . .
H2 H -0.040(5) 0.420(4) 0.337(2) 0.042(13) Uiso 1 1 d . . . . .
N3 N 0.2695(3) 0.5795(3) 0.41724(17) 0.0289(7) Uani 1 1 d . . . . .
N4 N 0.4892(3) 0.4768(3) 0.34383(18) 0.0309(7) Uani 1 1 d . . . . .
H4 H 0.544(6) 0.417(5) 0.347(3) 0.048(14) Uiso 1 1 d . . . . .
N5 N 0.2565(3) 0.0493(3) 0.25575(17) 0.0310(7) Uani 1 1 d . . . . .
N6 N 0.4277(3) 0.1276(3) 0.15780(18) 0.0310(7) Uani 1 1 d . . . . .
H6 H 0.492(4) 0.185(4) 0.150(2) 0.022(9) Uiso 1 1 d . . . . .
N7 N 0.1572(3) 0.0394(3) 0.11446(17) 0.0290(7) Uani 1 1 d . . . . .
N8 N -0.0080(3) 0.1262(3) 0.22404(18) 0.0323(7) Uani 1 1 d . . . . .
H8 H -0.051(6) 0.190(5) 0.238(3) 0.046(14) Uiso 1 1 d . . . . .
C1 C 0.3879(4) 0.5749(4) 0.2446(2) 0.0356(9) Uani 1 1 d . . . . .
C2 C 0.3964(5) 0.6497(5) 0.1945(3) 0.0479(12) Uani 1 1 d . . . . .
H2A H 0.4889 0.6721 0.1780 0.057 Uiso 1 1 calc R . . . .
C3 C 0.2679(5) 0.6922(5) 0.1683(3) 0.0514(12) Uani 1 1 d . . . . .
H3 H 0.2716 0.7425 0.1326 0.062 Uiso 1 1 calc R . . . .
C4 C 0.1341(5) 0.6610(4) 0.1941(2) 0.0418(10) Uani 1 1 d . . . . .
H4A H 0.0456 0.6916 0.1778 0.050 Uiso 1 1 calc R . . . .
C5 C 0.1322(4) 0.5851(4) 0.2439(2) 0.0339(9) Uani 1 1 d . . . . .
C6 C -0.0053(4) 0.5357(4) 0.2732(2) 0.0350(9) Uani 1 1 d . . . . .
H6A H -0.0753 0.5996 0.2841 0.042 Uiso 1 1 calc R . . . .
H6B H -0.0527 0.4742 0.2360 0.042 Uiso 1 1 calc R . . . .
C7 C 0.0040(4) 0.5644(4) 0.4085(2) 0.0340(8) Uani 1 1 d . . . . .
H7A H -0.0361 0.5176 0.4439 0.041 Uiso 1 1 calc R . . . .
H7B H -0.0692 0.6229 0.3995 0.041 Uiso 1 1 calc R . . . .
C8 C 0.1448(4) 0.6288(3) 0.4399(2) 0.0307(8) Uani 1 1 d . . . . .
C9 C 0.1483(5) 0.7284(4) 0.4924(2) 0.0370(9) Uani 1 1 d . . . . .
H9 H 0.0604 0.7635 0.5088 0.044 Uiso 1 1 calc R . . . .
C10 C 0.2858(5) 0.7749(4) 0.5202(2) 0.0396(9) Uani 1 1 d . . . . .
H10 H 0.2919 0.8417 0.5571 0.047 Uiso 1 1 calc R . . . .
C11 C 0.4131(4) 0.7249(4) 0.4944(2) 0.0347(9) Uani 1 1 d . . . . .
H11 H 0.5068 0.7574 0.5125 0.042 Uiso 1 1 calc R . . . .
C12 C 0.4007(4) 0.6269(3) 0.4421(2) 0.0305(8) Uani 1 1 d . . . . .
C13 C 0.5320(4) 0.5633(4) 0.4093(2) 0.0361(9) Uani 1 1 d . . . . .
H13A H 0.6042 0.6222 0.3964 0.043 Uiso 1 1 calc R . . . .
H13B H 0.5801 0.5215 0.4456 0.043 Uiso 1 1 calc R . . . .
C14 C 0.5181(4) 0.5176(4) 0.2749(2) 0.0407(10) Uani 1 1 d . . . . .
H14A H 0.5449 0.4495 0.2394 0.049 Uiso 1 1 calc R . . . .
H14B H 0.6029 0.5749 0.2820 0.049 Uiso 1 1 calc R . . . .
C15 C 0.1504(4) 0.0065(4) 0.2928(2) 0.0363(9) Uani 1 1 d . . . . .
C16 C 0.1762(5) -0.0820(5) 0.3334(3) 0.0506(12) Uani 1 1 d . . . . .
H16 H 0.1007 -0.1116 0.3601 0.061 Uiso 1 1 calc R . . . .
C17 C 0.3152(6) -0.1257(5) 0.3339(3) 0.0577(14) Uani 1 1 d . . . . .
H17 H 0.3355 -0.1874 0.3608 0.069 Uiso 1 1 calc R . . . .
C18 C 0.4252(5) -0.0815(5) 0.2960(3) 0.0513(12) Uani 1 1 d . . . . .
H18 H 0.5218 -0.1100 0.2980 0.062 Uiso 1 1 calc R . . . .
C19 C 0.3921(4) 0.0053(4) 0.2549(2) 0.0363(9) Uani 1 1 d . . . . .
C20 C 0.5004(4) 0.0638(4) 0.2120(2) 0.0374(9) Uani 1 1 d . . . . .
H20A H 0.5647 0.1204 0.2453 0.045 Uiso 1 1 calc R . . . .
H20B H 0.5632 0.0032 0.1868 0.045 Uiso 1 1 calc R . . . .
C21 C 0.4094(4) 0.0587(4) 0.0843(2) 0.0340(9) Uani 1 1 d . . . . .
H21A H 0.4899 0.0030 0.0765 0.041 Uiso 1 1 calc R . . . .
H21B H 0.4162 0.1131 0.0483 0.041 Uiso 1 1 calc R . . . .
C22 C 0.2637(4) -0.0094(3) 0.0730(2) 0.0308(8) Uani 1 1 d . . . . .
C23 C 0.2344(4) -0.1108(4) 0.0231(2) 0.0342(9) Uani 1 1 d . . . . .
H23 H 0.3093 -0.1445 -0.0063 0.041 Uiso 1 1 calc R . . . .
C24 C 0.0937(5) -0.1615(4) 0.0171(2) 0.0385(9) Uani 1 1 d . . . . .
H24 H 0.0708 -0.2303 -0.0170 0.046 Uiso 1 1 calc R . . . .
C25 C -0.0143(4) -0.1111(4) 0.0616(2) 0.0358(9) Uani 1 1 d . . . . .
H25 H -0.1111 -0.1454 0.0583 0.043 Uiso 1 1 calc R . . . .
C26 C 0.0219(4) -0.0108(4) 0.1103(2) 0.0307(8) Uani 1 1 d . . . . .
C27 C -0.0853(4) 0.0544(4) 0.1602(2) 0.0337(8) Uani 1 1 d . . . . .
H27A H -0.1429 0.1066 0.1335 0.040 Uiso 1 1 calc R . . . .
H27B H -0.1546 -0.0033 0.1765 0.040 Uiso 1 1 calc R . . . .
C28 C 0.0048(4) 0.0650(4) 0.2883(2) 0.0388(9) Uani 1 1 d . . . . .
H28A H -0.0761 0.0046 0.2858 0.047 Uiso 1 1 calc R . . . .
H28B H -0.0053 0.1229 0.3325 0.047 Uiso 1 1 calc R . . . .
Cl3 Cl 0.75483(9) 0.29546(9) 0.30699(6) 0.0368(2) Uani 1 1 d . . . . .
Cl4 Cl 0.76368(12) 0.78339(12) 0.21290(8) 0.0604(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 Cl1 2.3294(11) . ?
Fe1 O1 1.776(3) . ?
Fe1 N1 2.125(3) . ?
Fe1 N2 2.209(3) . ?
Fe1 N3 2.149(3) . ?
Fe1 N4 2.229(3) . ?
Fe2 Cl2 2.3007(12) . ?
Fe2 O1 1.775(3) . ?
Fe2 N5 2.134(3) . ?
Fe2 N6 2.224(3) . ?
Fe2 N7 2.152(3) . ?
Fe2 N8 2.212(3) . ?
N1 C1 1.335(5) . ?
N1 C5 1.350(5) . ?
N2 H2 0.94(5) . ?
N2 C6 1.485(5) . ?
N2 C7 1.497(5) . ?
N3 C8 1.340(5) . ?
N3 C12 1.335(5) . ?
N4 H4 0.87(5) . ?
N4 C13 1.488(5) . ?
N4 C14 1.473(5) . ?
N5 C15 1.335(5) . ?
N5 C19 1.350(5) . ?
N6 H6 0.90(4) . ?
N6 C20 1.490(5) . ?
N6 C21 1.483(5) . ?
N7 C22 1.350(5) . ?
N7 C26 1.338(5) . ?
N8 H8 0.85(5) . ?
N8 C27 1.486(5) . ?
N8 C28 1.489(5) . ?
C1 C2 1.370(6) . ?
C1 C14 1.510(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.385(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(6) . ?
C4 H4A 0.9500 . ?
C4 C5 1.372(6) . ?
C5 C6 1.514(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.513(5) . ?
C8 C9 1.388(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.396(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.374(6) . ?
C12 C13 1.523(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.382(6) . ?
C15 C28 1.512(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.378(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(6) . ?
C19 C20 1.502(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.509(5) . ?
C22 C23 1.389(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.397(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.379(6) . ?
C26 C27 1.514(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 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
O1 Fe1 Cl1 98.88(10) . . ?
O1 Fe1 N1 93.39(13) . . ?
O1 Fe1 N2 109.49(13) . . ?
O1 Fe1 N3 170.60(13) . . ?
O1 Fe1 N4 96.02(13) . . ?
N1 Fe1 Cl1 166.42(9) . . ?
N1 Fe1 N2 75.80(12) . . ?
N1 Fe1 N3 81.08(12) . . ?
N1 Fe1 N4 76.45(12) . . ?
N2 Fe1 Cl1 94.51(9) . . ?
N2 Fe1 N4 143.05(13) . . ?
N3 Fe1 Cl1 87.50(9) . . ?
N3 Fe1 N2 76.65(12) . . ?
N3 Fe1 N4 75.36(12) . . ?
N4 Fe1 Cl1 107.80(9) . . ?
O1 Fe2 Cl2 98.93(10) . . ?
O1 Fe2 N5 90.76(13) . . ?
O1 Fe2 N6 101.62(13) . . ?
O1 Fe2 N7 170.76(13) . . ?
O1 Fe2 N8 102.77(13) . . ?
N5 Fe2 Cl2 170.30(10) . . ?
N5 Fe2 N6 76.32(12) . . ?
N5 Fe2 N7 80.03(12) . . ?
N5 Fe2 N8 75.84(12) . . ?
N6 Fe2 Cl2 101.87(9) . . ?
N7 Fe2 Cl2 90.28(9) . . ?
N7 Fe2 N6 75.61(12) . . ?
N7 Fe2 N8 75.83(12) . . ?
N8 Fe2 Cl2 101.46(9) . . ?
N8 Fe2 N6 142.90(13) . . ?
Fe2 O1 Fe1 158.64(18) . . ?
C1 N1 Fe1 118.7(3) . . ?
C1 N1 C5 121.0(3) . . ?
C5 N1 Fe1 120.3(3) . . ?
Fe1 N2 H2 109(3) . . ?
C6 N2 Fe1 111.3(2) . . ?
C6 N2 H2 104(3) . . ?
C6 N2 C7 114.7(3) . . ?
C7 N2 Fe1 109.6(2) . . ?
C7 N2 H2 108(3) . . ?
C8 N3 Fe1 118.2(3) . . ?
C12 N3 Fe1 120.5(3) . . ?
C12 N3 C8 121.3(3) . . ?
Fe1 N4 H4 110(3) . . ?
C13 N4 Fe1 112.1(2) . . ?
C13 N4 H4 104(3) . . ?
C14 N4 Fe1 107.8(2) . . ?
C14 N4 H4 108(3) . . ?
C14 N4 C13 115.0(3) . . ?
C15 N5 Fe2 119.7(3) . . ?
C15 N5 C19 121.2(3) . . ?
C19 N5 Fe2 119.1(3) . . ?
Fe2 N6 H6 115(3) . . ?
C20 N6 Fe2 109.8(2) . . ?
C20 N6 H6 107(2) . . ?
C21 N6 Fe2 110.1(2) . . ?
C21 N6 H6 100(2) . . ?
C21 N6 C20 114.5(3) . . ?
C22 N7 Fe2 119.4(2) . . ?
C26 N7 Fe2 119.4(3) . . ?
C26 N7 C22 120.9(3) . . ?
Fe2 N8 H8 103(3) . . ?
C27 N8 Fe2 110.7(2) . . ?
C27 N8 H8 113(3) . . ?
C27 N8 C28 114.1(3) . . ?
C28 N8 Fe2 110.2(2) . . ?
C28 N8 H8 106(3) . . ?
N1 C1 C2 120.8(4) . . ?
N1 C1 C14 114.7(4) . . ?
C2 C1 C14 124.4(4) . . ?
C1 C2 H2A 120.5 . . ?
C1 C2 C3 118.9(4) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 C3 118.6(4) . . ?
C5 C4 H4A 120.7 . . ?
N1 C5 C4 120.7(4) . . ?
N1 C5 C6 114.1(3) . . ?
C4 C5 C6 125.0(3) . . ?
N2 C6 C5 111.9(3) . . ?
N2 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
N2 C7 C8 112.1(3) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
N3 C8 C7 115.7(3) . . ?
N3 C8 C9 120.8(4) . . ?
C9 C8 C7 123.4(3) . . ?
C8 C9 H9 121.2 . . ?
C8 C9 C10 117.6(4) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.3(4) . . ?
C12 C11 H11 120.8 . . ?
N3 C12 C11 121.2(3) . . ?
N3 C12 C13 115.1(3) . . ?
C11 C12 C13 123.6(3) . . ?
N4 C13 C12 112.3(3) . . ?
N4 C13 H13A 109.1 . . ?
N4 C13 H13B 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
N4 C14 C1 112.9(3) . . ?
N4 C14 H14A 109.0 . . ?
N4 C14 H14B 109.0 . . ?
C1 C14 H14A 109.0 . . ?
C1 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N5 C15 C16 121.4(4) . . ?
N5 C15 C28 114.8(3) . . ?
C16 C15 C28 123.8(4) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 C15 117.7(4) . . ?
C17 C16 H16 121.2 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.6(4) . . ?
C19 C18 H18 120.7 . . ?
N5 C19 C18 119.9(4) . . ?
N5 C19 C20 115.1(3) . . ?
C18 C19 C20 124.9(4) . . ?
N6 C20 C19 112.7(3) . . ?
N6 C20 H20A 109.1 . . ?
N6 C20 H20B 109.1 . . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
N6 C21 H21A 109.2 . . ?
N6 C21 H21B 109.2 . . ?
N6 C21 C22 111.8(3) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
N7 C22 C21 114.0(3) . . ?
N7 C22 C23 120.8(3) . . ?
C23 C22 C21 125.1(3) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 C22 118.7(4) . . ?
C24 C23 H23 120.7 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.6(4) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 120.5 . . ?
C26 C25 C24 119.0(4) . . ?
C26 C25 H25 120.5 . . ?
N7 C26 C25 121.0(4) . . ?
N7 C26 C27 114.6(3) . . ?
C25 C26 C27 124.3(3) . . ?
N8 C27 C26 111.5(3) . . ?
N8 C27 H27A 109.3 . . ?
N8 C27 H27B 109.3 . . ?
C26 C27 H27A 109.3 . . ?
C26 C27 H27B 109.3 . . ?
H27A C27 H27B 108.0 . . ?
N8 C28 C15 111.8(3) . . ?
N8 C28 H28A 109.3 . . ?
N8 C28 H28B 109.3 . . ?
C15 C28 H28A 109.3 . . ?
C15 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?

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
N2 H2 Cl3 0.94(5) 2.31(5) 3.219(4) 162(4) 1_455
N4 H4 Cl3 0.87(5) 2.48(5) 3.269(3) 150(4) .
N8 H8 Cl3 0.85(5) 2.47(5) 3.236(3) 150(4) 1_455
C2 H2A Cl4 0.95 2.78 3.618(5) 147.2 .
C4 H4A Cl4 0.95 2.87 3.707(4) 147.6 1_455
C9 H9 Cl1 0.95 2.94 3.680(4) 136.0 2_566
C11 H11 Cl1 0.95 2.85 3.624(4) 139.3 2_666
C18 H18 Cl4 0.95 2.96 3.780(5) 145.4 1_545
C20 H20A Cl3 0.99 2.70 3.669(4) 166.2 .
C27 H27B Cl4 0.99 2.73 3.648(4) 154.7 1_445

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
Fe1 N1 C1 C2 176.9(4) . . . . ?
Fe1 N1 C1 C14 0.4(5) . . . . ?
Fe1 N1 C5 C4 -177.4(3) . . . . ?
Fe1 N1 C5 C6 -1.2(5) . . . . ?
Fe1 N2 C6 C5 -27.9(4) . . . . ?
Fe1 N2 C7 C8 30.2(4) . . . . ?
Fe1 N3 C8 C7 -0.1(4) . . . . ?
Fe1 N3 C8 C9 175.9(3) . . . . ?
Fe1 N3 C12 C11 -175.5(3) . . . . ?
Fe1 N3 C12 C13 3.5(5) . . . . ?
Fe1 N4 C13 C12 -22.5(4) . . . . ?
Fe1 N4 C14 C1 33.3(4) . . . . ?
Fe2 N5 C15 C16 -178.4(4) . . . . ?
Fe2 N5 C15 C28 -0.3(5) . . . . ?
Fe2 N5 C19 C18 176.9(4) . . . . ?
Fe2 N5 C19 C20 1.3(5) . . . . ?
Fe2 N6 C20 C19 28.8(4) . . . . ?
Fe2 N6 C21 C22 -33.2(4) . . . . ?
Fe2 N7 C22 C21 -6.8(4) . . . . ?
Fe2 N7 C22 C23 175.7(3) . . . . ?
Fe2 N7 C26 C25 -176.0(3) . . . . ?
Fe2 N7 C26 C27 6.6(4) . . . . ?
Fe2 N8 C27 C26 31.1(4) . . . . ?
Fe2 N8 C28 C15 -30.1(4) . . . . ?
Cl1 Fe1 O1 Fe2 105.0(5) . . . . ?
Cl2 Fe2 O1 Fe1 54.6(5) . . . . ?
N1 Fe1 O1 Fe2 -69.1(5) . . . . ?
N1 C1 C2 C3 0.7(8) . . . . ?
N1 C1 C14 N4 -23.7(6) . . . . ?
N1 C5 C6 N2 19.8(5) . . . . ?
N2 Fe1 O1 Fe2 7.0(5) . . . . ?
N2 C7 C8 N3 -20.7(5) . . . . ?
N2 C7 C8 C9 163.3(4) . . . . ?
N3 C8 C9 C10 0.2(6) . . . . ?
N3 C12 C13 N4 13.2(5) . . . . ?
N4 Fe1 O1 Fe2 -145.8(5) . . . . ?
N5 Fe2 O1 Fe1 -125.1(5) . . . . ?
N5 C15 C16 C17 -0.7(8) . . . . ?
N5 C15 C28 N8 20.8(5) . . . . ?
N5 C19 C20 N6 -20.8(5) . . . . ?
N6 Fe2 O1 Fe1 158.8(5) . . . . ?
N6 C21 C22 N7 27.0(5) . . . . ?
N6 C21 C22 C23 -155.6(4) . . . . ?
N7 C22 C23 C24 -0.6(6) . . . . ?
N7 C26 C27 N8 -25.4(5) . . . . ?
N8 Fe2 O1 Fe1 -49.4(5) . . . . ?
C1 N1 C5 C4 1.9(6) . . . . ?
C1 N1 C5 C6 178.1(4) . . . . ?
C1 C2 C3 C4 1.6(8) . . . . ?
C2 C1 C14 N4 159.9(4) . . . . ?
C2 C3 C4 C5 -2.1(8) . . . . ?
C3 C4 C5 N1 0.4(7) . . . . ?
C3 C4 C5 C6 -175.4(5) . . . . ?
C4 C5 C6 N2 -164.2(4) . . . . ?
C5 N1 C1 C2 -2.4(7) . . . . ?
C5 N1 C1 C14 -178.9(4) . . . . ?
C6 N2 C7 C8 -95.8(4) . . . . ?
C7 N2 C6 C5 97.2(4) . . . . ?
C7 C8 C9 C10 176.0(4) . . . . ?
C8 N3 C12 C11 3.1(6) . . . . ?
C8 N3 C12 C13 -177.9(3) . . . . ?
C8 C9 C10 C11 1.8(6) . . . . ?
C9 C10 C11 C12 -1.4(6) . . . . ?
C10 C11 C12 N3 -1.1(6) . . . . ?
C10 C11 C12 C13 -179.9(4) . . . . ?
C11 C12 C13 N4 -167.9(4) . . . . ?
C12 N3 C8 C7 -178.7(3) . . . . ?
C12 N3 C8 C9 -2.7(6) . . . . ?
C13 N4 C14 C1 -92.6(4) . . . . ?
C14 N4 C13 C12 101.1(4) . . . . ?
C14 C1 C2 C3 176.8(5) . . . . ?
C15 N5 C19 C18 -3.4(6) . . . . ?
C15 N5 C19 C20 -179.0(4) . . . . ?
C15 C16 C17 C18 1.0(9) . . . . ?
C16 C15 C28 N8 -161.1(4) . . . . ?
C16 C17 C18 C19 -2.4(9) . . . . ?
C17 C18 C19 N5 3.6(7) . . . . ?
C17 C18 C19 C20 178.7(5) . . . . ?
C18 C19 C20 N6 163.9(4) . . . . ?
C19 N5 C15 C16 1.9(7) . . . . ?
C19 N5 C15 C28 -180.0(4) . . . . ?
C20 N6 C21 C22 91.1(4) . . . . ?
C21 N6 C20 C19 -95.6(4) . . . . ?
C21 C22 C23 C24 -177.8(4) . . . . ?
C22 N7 C26 C25 -2.7(6) . . . . ?
C22 N7 C26 C27 180.0(3) . . . . ?
C22 C23 C24 C25 -0.8(6) . . . . ?
C23 C24 C25 C26 0.5(6) . . . . ?
C24 C25 C26 N7 1.3(6) . . . . ?
C24 C25 C26 C27 178.4(4) . . . . ?
C25 C26 C27 N8 157.4(4) . . . . ?
C26 N7 C22 C21 179.8(3) . . . . ?
C26 N7 C22 C23 2.3(6) . . . . ?
C27 N8 C28 C15 95.2(4) . . . . ?
C28 N8 C27 C26 -93.9(4) . . . . ?
C28 C15 C16 C17 -178.6(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.092 0.000 0.500 171.2 28.9 ?
2 -0.641 0.500 1.000 300.7 79.2 ?

_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_yuto_ni_0m
_database_code_depnum_ccdc_archive 'CCDC 1892443'
loop_
_audit_author_name
_audit_author_address
'Mihaela Cibian'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-01-21 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
_vrf_PLAT094_yuto_ni_0m          
;
PROBLEM: 
Ratio of Maximum / Minimum Residual Density .... 2.49 Report

RESPONSE: 
checked; the six highest residual electron density peaks (1.46, 
1.32, 1.22, 0.83, 0.76, 0.74 eA-3) do not make chemical sense; 
they are localized next to the Ni and Cl atoms, the heaviest atoms 
in the structure, and they can therefore be attributed to Fourier 
transform truncation errors; poor overall quality of the data set 
as result of the poor quality of the crystal 
;
_vrf_PLAT250_yuto_ni_0m          
;
PROBLEM: 
Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.2 Note

RESPONSE: 
poor overall quality of the data set as result of the poor quality 
of the crystal 
;
_vrf_PLAT480_yuto_ni_0m          
;
PROBLEM: 
Long H...A H-Bond Reported H2 ..CL3 . 2.94 Ang.

RESPONSE: 
indication of week hydrogen bonding
;
_vrf_PLAT304_yuto_ni_0m          
;
PROBLEM: 
Non-Integer Number of Atoms in ...... Resd 2 0.25 Check
Non-Integer Number of Atoms in ...... Resd 3 0.25 Check

RESPONSE:
checked; Cl anions (not coordinated to the metal centre) placed on 
high symmetry positions 
;
_vrf_PLAT605_yuto_ni_0m          
;
PROBLEM: 
Largest Solvent Accessible VOID in the Structure 156 A**3

RESPONSE:
Disordered co-crystallized solvent was removed using SQUEEZE routine 
(PLATON (Spek, 2009)) as implemented in OLEX2 (Dolomanov et al., 2009). 
As a result, an improvement of the R1 factor with 5.7 % was obtained. 
The presence of 1.5 co-crystallized methanol molecules can be estimated 
based on the volumes of calculated accessible voids (328 Ang3 per 
unit cell), containing 57 electrons (Z=2), as well as on the insights 
obtained from the attempts to model the disordered solvent, 
and the identity of the solvents used for crystallization 
(methanol/ diethylether).
;

_vrf_PLAT868_yuto_ni_0m          
;
PROBLEM: 
ALERTS Due to the Use of _smtbx_masks Suppressed

RESPONSE:
Disordered co-crystallized solvent was removed using SQUEEZE routine 
(PLATON (Spek, 2009)) as implemented in OLEX2 (Dolomanov et al., 2009). 
As a result, an improvement of the R1 factor with 5.7 % was obtained. 
The presence of 1.5 co-crystallized methanol molecules can be estimated 
based on the volumes of calculated accessible voids (328 Ang3 per 
unit cell), containing 57 electrons (Z=2), as well as on the insights 
obtained from the attempts to model the disordered solvent, 
and the identity of the solvents used for crystallization 
(methanol/ diethylether).
;
_audit_creation_date             2018-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H32 Cl2 N8 Ni2, 2(Cl)'
_chemical_formula_sum            'C28 H32 Cl4 N8 Ni2'
_chemical_formula_weight         739.83
_chemical_melting_point          ?
_exptl_crystal_recrystallization_method 
'slow diffusion of diethylether into a solution of the compound in methanol'
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'

_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.178(5)
_cell_length_b                   8.837(3)
_cell_length_c                   12.505(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.309(3)
_cell_angle_gamma                90
_cell_volume                     1756.3(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3992
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.342
_cell_measurement_theta_min      2.498
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.786
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. 
wR2(int) was 0.1270 before and 0.0708 after correction. The Ratio 
of minimum to maximum transmission is 0.6424. The λ/2 correction 
factor is 0.00150.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker SMART APEX II Charged-Coupled Device (CCD) Area Detector 
diffractometer. The crystal-to-detector distance was 6.0 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10269
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         1.760
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode with a mirror focussing unit'
_diffrn_standards_number         ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1587
_reflns_number_total             2150
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.456
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.040
_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)+(0.0985P)²+1.3695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1644
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.52700(4) 0.500000 0.37922(5) 0.0309(2) Uani 1 2 d S T P . .
N1 N 0.4635(3) 0.500000 0.2072(4) 0.0312(9) Uani 1 2 d S T P . .
C1 C 0.4476(3) 0.3671(4) 0.1517(3) 0.0341(8) Uani 1 1 d . . . . .
Cl1 Cl 0.60171(9) 0.500000 0.58543(10) 0.0360(3) Uani 1 2 d S T P . .
N2 N 0.5354(2) 0.2630(4) 0.3446(3) 0.0374(8) Uani 1 1 d . . . . .
H2 H 0.523(3) 0.202(7) 0.383(4) 0.072(18) Uiso 1 1 d . . . . .
C2 C 0.4101(3) 0.3640(4) 0.0314(3) 0.0412(9) Uani 1 1 d . . . . .
H2A H 0.397878 0.270730 -0.009441 0.049 Uiso 1 1 calc R . . . .
N3 N 0.6351(3) 0.500000 0.3526(4) 0.0340(10) Uani 1 2 d S T P . .
C3 C 0.3914(4) 0.500000 -0.0264(5) 0.0442(14) Uani 1 2 d S T P . .
H3 H 0.364922 0.499999 -0.108342 0.053 Uiso 1 2 calc RS T P . .
C4 C 0.4695(3) 0.2306(4) 0.2295(3) 0.0450(10) Uani 1 1 d . . . . .
H4A H 0.418229 0.194128 0.239589 0.054 Uiso 1 1 calc R . . . .
H4B H 0.489386 0.148745 0.192043 0.054 Uiso 1 1 calc R . . . .
C5 C 0.6220(3) 0.2287(4) 0.3552(4) 0.0485(11) Uani 1 1 d . . . . .
H5A H 0.619941 0.154291 0.294975 0.058 Uiso 1 1 calc R . . . .
H5B H 0.652811 0.181553 0.431460 0.058 Uiso 1 1 calc R . . . .
C6 C 0.6698(3) 0.3673(4) 0.3430(3) 0.0396(9) Uani 1 1 d . . . . .
C7 C 0.7454(3) 0.3637(5) 0.3261(4) 0.0477(11) Uani 1 1 d . . . . .
H7 H 0.770580 0.270139 0.319674 0.057 Uiso 1 1 calc R . . . .
C8 C 0.7830(4) 0.500000 0.3190(5) 0.0491(15) Uani 1 2 d S T P . .
H8 H 0.835211 0.499999 0.309143 0.059 Uiso 1 2 calc RS T P . .
Cl2 Cl 0.500000 0.000000 0.500000 0.0322(4) Uani 1 4 d S T P . .
Cl3 Cl 0.500000 0.000000 0.000000 0.0709(8) Uani 1 4 d S T P . .


_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 2.009(4) . ?
Ni1 Cl1 2.4050(15) . ?
Ni1 Cl1 2.4136(15) 5_666 ?
Ni1 N2 2.155(3) 6_565 ?
Ni1 N2 2.155(3) . ?
Ni1 N3 2.007(4) . ?
N1 C1 1.339(4) . ?
N1 C1 1.339(4) 6_565 ?
C1 C2 1.394(5) . ?
C1 C4 1.505(5) . ?
N2 H2 0.80(6) . ?
N2 C4 1.483(5) . ?
N2 C5 1.474(6) . ?
C2 H2A 0.9500 . ?
C2 C3 1.377(5) . ?
N3 C6 1.342(4) . ?
N3 C6 1.342(4) 6_565 ?
C3 H3 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.514(6) . ?
C6 C7 1.393(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(5) . ?
C8 H8 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
N1 Ni1 Cl1 179.44(12) . . ?
N1 Ni1 Cl1 91.92(13) . 5_666 ?
N1 Ni1 N2 80.54(9) . 6_565 ?
N1 Ni1 N2 80.54(9) . . ?
Cl1 Ni1 Cl1 87.52(5) . 5_666 ?
N2 Ni1 Cl1 99.94(9) . 5_666 ?
N2 Ni1 Cl1 99.94(9) 6_565 5_666 ?
N2 Ni1 Cl1 99.56(9) . . ?
N2 Ni1 Cl1 99.56(9) 6_565 . ?
N2 Ni1 N2 152.88(16) 6_565 . ?
N3 Ni1 N1 89.01(17) . . ?
N3 Ni1 Cl1 91.56(13) . . ?
N3 Ni1 Cl1 179.08(13) . 5_666 ?
N3 Ni1 N2 80.21(10) . . ?
N3 Ni1 N2 80.21(10) . 6_565 ?
C1 N1 Ni1 118.4(2) . . ?
C1 N1 Ni1 118.4(2) 6_565 . ?
C1 N1 C1 122.7(4) 6_565 . ?
N1 C1 C2 119.8(3) . . ?
N1 C1 C4 114.6(3) . . ?
C2 C1 C4 125.5(3) . . ?
Ni1 Cl1 Ni1 92.48(5) . 5_666 ?
Ni1 N2 H2 119(4) . . ?
C4 N2 Ni1 107.3(2) . . ?
C4 N2 H2 100(4) . . ?
C5 N2 Ni1 108.9(2) . . ?
C5 N2 H2 107(4) . . ?
C5 N2 C4 114.8(3) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 H2A 121.0 . . ?
C6 N3 Ni1 119.1(2) . . ?
C6 N3 Ni1 119.1(2) 6_565 . ?
C6 N3 C6 121.9(5) . 6_565 ?
C2 C3 C2 121.7(5) 6_565 . ?
C2 C3 H3 119.2 . . ?
C2 C3 H3 119.2 6_565 . ?
C1 C4 H4A 109.1 . . ?
C1 C4 H4B 109.1 . . ?
N2 C4 C1 112.6(3) . . ?
N2 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N2 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
N2 C5 C6 113.1(3) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
N3 C6 C5 114.9(4) . . ?
N3 C6 C7 120.4(4) . . ?
C7 C6 C5 124.7(4) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 C6 118.3(4) . . ?
C8 C7 H7 120.9 . . ?
C7 C8 C7 120.8(6) 6_565 . ?
C7 C8 H8 119.6 6_565 . ?
C7 C8 H8 119.6 . . ?

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
N2 H2 Cl2 0.80(6) 2.43(6) 3.232(3) 173(5) . yes
C2 H2A Cl3 0.95 2.94 3.653(4) 132.6 . yes
C4 H4B Cl3 0.99 2.80 3.715(4) 153.3 . 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 N1 C1 C2 -174.5(3) . . . . ?
Ni1 N1 C1 C4 8.1(5) . . . . ?
Ni1 N2 C4 C1 27.3(4) . . . . ?
Ni1 N2 C5 C6 -20.9(4) . . . . ?
Ni1 N3 C6 C5 -0.6(5) . . . . ?
Ni1 N3 C6 C7 -179.1(3) . . . . ?
N1 C1 C2 C3 0.6(6) . . . . ?
N1 C1 C4 N2 -24.5(5) . . . . ?
C1 N1 C1 C2 -2.3(8) 6_565 . . . ?
C1 N1 C1 C4 -179.7(3) 6_565 . . . ?
C1 C2 C3 C2 1.2(9) . . . 6_565 ?
N2 C5 C6 N3 15.2(5) . . . . ?
N2 C5 C6 C7 -166.4(4) . . . . ?
C2 C1 C4 N2 158.3(4) . . . . ?
N3 C6 C7 C8 -0.3(6) . . . . ?
C4 C1 C2 C3 177.6(5) . . . . ?
C4 N2 C5 C6 99.5(4) . . . . ?
C5 N2 C4 C1 -94.0(4) . . . . ?
C5 C6 C7 C8 -178.6(4) . . . . ?
C6 N3 C6 C5 -179.6(3) 6_565 . . . ?
C6 N3 C6 C7 2.0(8) 6_565 . . . ?
C6 C7 C8 C7 -1.3(8) . . . 6_565 ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 -0.767 0.000 163.9 28.6 ?
2 0.750 -0.486 0.000 163.9 28.6 ?

_olex2_submission_special_instructions 'No special instructions were received'
