# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_OH153
_database_code_depnum_ccdc_archive 'CCDC 2370860'
loop_
_audit_author_name
_audit_author_address
'Laure Vendier'
;Laboratoire de Chimie de Coordination CNRS 
France
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, C2 H3 N4, 3(C3 H4 N2)'
_chemical_formula_sum            'C27 H51 N11'
_chemical_formula_weight         529.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 c 1 '
_symmetry_space_group_name_Hall  ' 	P -2yc '

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

_cell_length_a                   9.7821(4)
_cell_length_b                   8.2254(4)
_cell_length_c                   19.3571(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.447(3)
_cell_angle_gamma                90.00
_cell_volume                     1557.01(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7892
_cell_measurement_theta_min      4.5440
_cell_measurement_theta_max      76.7800

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02

_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_min  0.49458
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12397
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.522
_diffrn_reflns_theta_max         66.570
_diffrn_reflns_theta_full        66.570
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.668
_diffrn_reflns_point_group_measured_fraction_full 0.668
_reflns_number_total             3685
_reflns_number_gt                3390
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.336
_reflns_Friedel_fraction_max     0.337
_reflns_Friedel_fraction_full    0.337

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+0.1914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3685
_refine_ls_number_parameters     367
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.009
_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
C1 C 0.7663(3) 0.8742(4) 0.29917(17) 0.0405(7) Uani 1 1 d . . . . .
H1 H 0.862241 0.858433 0.296428 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6751(3) 0.8576(4) 0.24335(16) 0.0401(7) Uani 1 1 d . . . . .
H2 H 0.695025 0.829559 0.197074 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5500(3) 0.8908(3) 0.27018(15) 0.0355(6) Uani 1 1 d . . . . .
H3 H 0.464500 0.890612 0.245757 0.043 Uiso 1 1 calc R U . . .
C4 C 0.8888(3) 1.1725(4) 0.58818(16) 0.0387(7) Uani 1 1 d . . . . .
H4 H 0.920511 1.211379 0.631940 0.046 Uiso 1 1 calc R U . . .
C5 C 0.9700(3) 1.1582(4) 0.53128(18) 0.0397(7) Uani 1 1 d . . . . .
H5 H 1.064601 1.182631 0.528331 0.048 Uiso 1 1 calc R U . . .
C6 C 0.8833(3) 1.1004(3) 0.47963(17) 0.0372(6) Uani 1 1 d . . . . .
H6 H 0.906517 1.077777 0.433251 0.045 Uiso 1 1 calc R U . . .
C7 C 0.2089(4) 0.9010(4) 0.77853(16) 0.0431(7) Uani 1 1 d . . . . .
H7 H 0.258028 0.901387 0.821487 0.052 Uiso 1 1 calc R U . . .
C8 C 0.0691(3) 0.8798(4) 0.77170(17) 0.0424(7) Uani 1 1 d . . . . .
H8 H 0.005895 0.863058 0.807458 0.051 Uiso 1 1 calc R U . . .
C9 C 0.0416(3) 0.8882(4) 0.70162(16) 0.0401(7) Uani 1 1 d . . . . .
H9 H -0.045597 0.878457 0.679253 0.048 Uiso 1 1 calc R U . . .
C10 C 0.2664(3) 0.9844(3) 0.47230(14) 0.0318(6) Uani 1 1 d . . . . .
H10 H 0.178581 0.991073 0.450346 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4221(3) 0.9522(3) 0.54659(14) 0.0290(6) Uani 1 1 d . . . . .
C12 C 0.5529(3) 0.3763(3) 0.40393(14) 0.0283(6) Uani 1 1 d . . . . .
H12A H 0.626939 0.309012 0.424825 0.034 Uiso 1 1 calc R U . . .
H12B H 0.477044 0.302093 0.390503 0.034 Uiso 1 1 calc R U . . .
C13 C 0.6060(3) 0.4543(3) 0.33883(14) 0.0321(6) Uani 1 1 d . . . . .
H13A H 0.688487 0.519564 0.350471 0.039 Uiso 1 1 calc R U . . .
H13B H 0.535639 0.528261 0.318848 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6413(3) 0.3251(4) 0.28604(15) 0.0405(7) Uani 1 1 d . . . . .
H14A H 0.707441 0.247808 0.307439 0.049 Uiso 1 1 calc R U . . .
H14B H 0.557460 0.263531 0.273258 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7019(4) 0.3947(4) 0.22103(17) 0.0424(7) Uani 1 1 d . . . . .
H15A H 0.639784 0.476743 0.201203 0.064 Uiso 1 1 calc R U . . .
H15B H 0.714782 0.307341 0.187401 0.064 Uiso 1 1 calc R U . . .
H15C H 0.790422 0.445103 0.232503 0.064 Uiso 1 1 calc R U . . .
C16 C 0.4563(3) 0.3882(3) 0.51895(15) 0.0295(6) Uani 1 1 d . . . . .
H16A H 0.392003 0.304765 0.500746 0.035 Uiso 1 1 calc R U . . .
H16B H 0.537285 0.330584 0.538481 0.035 Uiso 1 1 calc R U . . .
C17 C 0.3879(3) 0.4779(3) 0.57708(15) 0.0325(6) Uani 1 1 d . . . . .
H17A H 0.301728 0.527954 0.559639 0.039 Uiso 1 1 calc R U . . .
H17B H 0.448688 0.565770 0.594599 0.039 Uiso 1 1 calc R U . . .
C18 C 0.3576(3) 0.3600(4) 0.63544(16) 0.0391(7) Uani 1 1 d . . . . .
H18A H 0.299825 0.270331 0.617032 0.047 Uiso 1 1 calc R U . . .
H18B H 0.444508 0.312275 0.653159 0.047 Uiso 1 1 calc R U . . .
C19 C 0.2851(4) 0.4416(5) 0.69459(17) 0.0508(8) Uani 1 1 d . . . . .
H19A H 0.342449 0.529445 0.713482 0.076 Uiso 1 1 calc R U . . .
H19B H 0.268226 0.361498 0.730865 0.076 Uiso 1 1 calc R U . . .
H19C H 0.197755 0.486551 0.677584 0.076 Uiso 1 1 calc R U . . .
C20 C 0.6131(3) 0.6104(3) 0.48182(14) 0.0282(6) Uani 1 1 d . . . . .
H20A H 0.638539 0.676340 0.441349 0.034 Uiso 1 1 calc R U . . .
H20B H 0.574234 0.685381 0.516179 0.034 Uiso 1 1 calc R U . . .
C21 C 0.7423(3) 0.5361(3) 0.51311(15) 0.0308(6) Uani 1 1 d . . . . .
H21A H 0.778518 0.452814 0.481507 0.037 Uiso 1 1 calc R U . . .
H21B H 0.721767 0.482829 0.557515 0.037 Uiso 1 1 calc R U . . .
C22 C 0.8487(3) 0.6701(4) 0.52508(15) 0.0348(6) Uani 1 1 d . . . . .
H22A H 0.869303 0.721418 0.480281 0.042 Uiso 1 1 calc R U . . .
H22B H 0.810049 0.754669 0.555288 0.042 Uiso 1 1 calc R U . . .
C23 C 0.9807(3) 0.6058(4) 0.55822(17) 0.0405(7) Uani 1 1 d . . . . .
H23A H 0.962263 0.563534 0.604400 0.061 Uiso 1 1 calc R U . . .
H23B H 1.047811 0.694021 0.561986 0.061 Uiso 1 1 calc R U . . .
H23C H 1.017144 0.518346 0.529618 0.061 Uiso 1 1 calc R U . . .
C24 C 0.3835(3) 0.5939(3) 0.43088(14) 0.0286(5) Uani 1 1 d . . . . .
H24A H 0.352239 0.665721 0.468376 0.034 Uiso 1 1 calc R U . . .
H24B H 0.417636 0.664548 0.393667 0.034 Uiso 1 1 calc R U . . .
C25 C 0.2612(3) 0.4997(3) 0.40258(15) 0.0318(6) Uani 1 1 d . . . . .
H25A H 0.231230 0.420272 0.437503 0.038 Uiso 1 1 calc R U . . .
H25B H 0.287451 0.438836 0.360823 0.038 Uiso 1 1 calc R U . . .
C26 C 0.1438(3) 0.6155(4) 0.38432(16) 0.0343(6) Uani 1 1 d . . . . .
H26A H 0.117934 0.676064 0.426222 0.041 Uiso 1 1 calc R U . . .
H26B H 0.174574 0.695394 0.349755 0.041 Uiso 1 1 calc R U . . .
C27 C 0.0194(3) 0.5246(4) 0.35533(19) 0.0447(7) Uani 1 1 d . . . . .
H27A H 0.042832 0.471530 0.311861 0.067 Uiso 1 1 calc R U . . .
H27B H -0.055671 0.601408 0.346838 0.067 Uiso 1 1 calc R U . . .
H27C H -0.008852 0.442194 0.388648 0.067 Uiso 1 1 calc R U . . .
N1 N 0.5708(3) 0.9235(3) 0.33724(13) 0.0341(5) Uani 1 1 d . . . . .
N2 N 0.7035(3) 0.9147(3) 0.35686(14) 0.0409(6) Uani 1 1 d . . . . .
N3 N 0.7603(3) 1.0822(3) 0.50728(12) 0.0328(5) Uani 1 1 d . . . . .
N4 N 0.7602(3) 1.1254(3) 0.57449(13) 0.0367(6) Uani 1 1 d . . . . .
N5 N 0.1603(3) 0.9127(3) 0.67126(14) 0.0366(5) Uani 1 1 d . . . . .
N6 N 0.2661(3) 0.9207(3) 0.71745(13) 0.0419(6) Uani 1 1 d . . . . .
N7 N 0.4846(2) 0.9909(3) 0.48892(12) 0.0304(5) Uani 1 1 d . . . . .
N8 N 0.3801(2) 1.0124(3) 0.43933(12) 0.0311(5) Uani 1 1 d . . . . .
N9 N 0.2843(2) 0.9452(3) 0.54023(12) 0.0319(5) Uani 1 1 d . . . . .
N10 N 0.4939(3) 0.9137(3) 0.60726(12) 0.0329(5) Uani 1 1 d . . . . .
N11 N 0.5020(2) 0.4919(3) 0.45886(12) 0.0282(5) Uani 1 1 d . . . . .
H1B H 0.506(4) 0.952(4) 0.3684(18) 0.037(9) Uiso 1 1 d . . . . .
H3X H 0.682(4) 1.042(4) 0.4908(17) 0.031(8) Uiso 1 1 d . . . . .
H5X H 0.184(5) 0.925(5) 0.624(3) 0.068(13) Uiso 1 1 d . . . . .
H10A H 0.580(4) 0.968(5) 0.6109(19) 0.049(10) Uiso 1 1 d . . . . .
H10B H 0.442(3) 0.922(3) 0.6475(17) 0.028(7) Uiso 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
C1 N2 1.331(4) . ?
C1 C2 1.391(4) . ?
C2 C3 1.369(4) . ?
C3 N1 1.336(4) . ?
C4 N4 1.336(4) . ?
C4 C5 1.379(5) . ?
C5 C6 1.379(4) . ?
C6 N3 1.337(4) . ?
C7 N6 1.331(4) . ?
C7 C8 1.381(5) . ?
C8 C9 1.378(4) . ?
C9 N5 1.330(4) . ?
C10 N8 1.317(4) . ?
C10 N9 1.361(4) . ?
C11 N7 1.325(4) . ?
C11 N9 1.352(4) . ?
C11 N10 1.390(4) . ?
C12 C13 1.518(4) . ?
C12 N11 1.520(3) . ?
C13 C14 1.520(4) . ?
C14 C15 1.517(4) . ?
C16 C17 1.515(4) . ?
C16 N11 1.518(3) . ?
C17 C18 1.524(4) . ?
C18 C19 1.518(4) . ?
C20 C21 1.516(4) . ?
C20 N11 1.518(3) . ?
C21 C22 1.529(4) . ?
C22 C23 1.523(4) . ?
C24 C25 1.516(4) . ?
C24 N11 1.520(3) . ?
C25 C26 1.527(4) . ?
C26 C27 1.523(4) . ?
N1 N2 1.345(4) . ?
N3 N4 1.349(3) . ?
N5 N6 1.352(4) . ?
N7 N8 1.395(3) . ?

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 C1 C2 112.1(3) . . ?
C3 C2 C1 104.4(3) . . ?
N1 C3 C2 107.0(3) . . ?
N4 C4 C5 112.0(3) . . ?
C6 C5 C4 104.6(3) . . ?
N3 C6 C5 106.9(3) . . ?
N6 C7 C8 111.6(3) . . ?
C9 C8 C7 104.9(3) . . ?
N5 C9 C8 106.9(3) . . ?
N8 C10 N9 114.8(3) . . ?
N7 C11 N9 114.4(2) . . ?
N7 C11 N10 122.2(3) . . ?
N9 C11 N10 123.3(3) . . ?
C13 C12 N11 116.2(2) . . ?
C12 C13 C14 110.5(2) . . ?
C15 C14 C13 113.2(3) . . ?
C17 C16 N11 116.1(2) . . ?
C16 C17 C18 109.8(2) . . ?
C19 C18 C17 112.4(3) . . ?
C21 C20 N11 116.2(2) . . ?
C20 C21 C22 109.1(2) . . ?
C23 C22 C21 112.4(2) . . ?
C25 C24 N11 115.7(2) . . ?
C24 C25 C26 110.3(2) . . ?
C27 C26 C25 111.6(2) . . ?
C3 N1 N2 112.7(3) . . ?
C1 N2 N1 103.8(2) . . ?
C6 N3 N4 112.3(3) . . ?
C4 N4 N3 104.1(2) . . ?
C9 N5 N6 112.2(3) . . ?
C7 N6 N5 104.4(3) . . ?
C11 N7 N8 105.3(2) . . ?
C10 N8 N7 104.9(2) . . ?
C11 N9 C10 100.5(2) . . ?
C20 N11 C16 111.0(2) . . ?
C20 N11 C12 111.2(2) . . ?
C16 N11 C12 107.02(19) . . ?
C20 N11 C24 106.47(18) . . ?
C16 N11 C24 110.3(2) . . ?
C12 N11 C24 110.9(2) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_OH184-100K
_database_code_depnum_ccdc_archive 'CCDC 2370861'
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;


_cell_length_a                   10.364(3)
_cell_length_b                   16.490(4)
_cell_length_c                   12.598(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.789(8)
_cell_angle_gamma                90
_cell_volume                     2142.1(10)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Fe 0.3463 0.8444 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805
1.0369 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C14 H25 B1 Fe1 N16 
# Dc =      1.50 Fooo =   1008.00 Mu =      7.44 M =    484.12
# Found Formula = C16 H20 B2 Fe1 N16 
# Dc =      1.59 FOOO =   1056.00 Mu =      7.49 M =    513.91

_chemical_formula_sum            'C16 H20 B2 Fe N16'
_chemical_formula_moiety         'C16 H20 B2 Fe N16'
_chemical_compound_source        .
_chemical_formula_weight         513.91


_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      26.33
_cell_measurement_temperature    100

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'light blue'
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_max          0.110

_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.749

# Sheldrick geometric approximatio 0.95 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            58852
_diffrn_reflns_av_unetI/netI     0.137
_reflns_number_total             4388
_diffrn_reflns_av_R_equivalents  0.093
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4388 
# Theoretical number of reflections is about 8811 


_diffrn_reflns_theta_min         2.041
_diffrn_reflns_theta_max         26.425
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        26.425
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.44
_refine_diff_density_max         0.89


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4388
_oxford_refine_ls_R_factor_ref   0.0438
_refine_ls_R_factor_all          0.0438
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_all         0.0966
_refine_ls_goodness_of_fit_ref   0.9484
_refine_ls_shift/su_max          0.0004922
_refine_ls_shift/su_mean         0.0000418


# Computed with I/sigma = -10 
_oxford_reflns_number_all        4388
_oxford_refine_ls_R_factor_all   0.0438
_oxford_refine_ls_wR_factor_all  0.0966

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3741
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_gt          0.0904


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 3.12P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Fe1 Fe 0.64695(3) 0.657470(18) 0.33460(2) 0.0102 1.0000 Uani . . . . . .
N6 N 0.46970(17) 0.61317(10) 0.30228(14) 0.0115 1.0000 Uani . . . . . .
N3 N 0.64137(17) 0.56365(11) 0.13763(14) 0.0124 1.0000 Uani . . . . . .
N14 N 0.82469(17) 0.70024(11) 0.36819(14) 0.0139 1.0000 Uani . . . . . .
N1 N 0.66800(17) 0.48264(11) 0.30395(15) 0.0137 1.0000 Uani . . . . . .
N13 N 0.84201(17) 0.77072(11) 0.42814(15) 0.0128 1.0000 Uani . . . . . .
N5 N 0.45294(17) 0.54243(10) 0.24302(14) 0.0120 1.0000 Uani . . . . . .
N10 N 0.61857(17) 0.67631(11) 0.48634(15) 0.0126 1.0000 Uani . . . . . .
N9 N 0.65730(17) 0.74791(11) 0.53468(15) 0.0132 1.0000 Uani . . . . . .
N2 N 0.70612(17) 0.54544(11) 0.37120(15) 0.0144 1.0000 Uani . . . . . .
N4 N 0.68084(17) 0.63610(11) 0.18400(14) 0.0125 1.0000 Uani . . . . . .
N11 N 0.62532(18) 0.83191(11) 0.37055(16) 0.0153 1.0000 Uani . . . . . .
N12 N 0.58531(17) 0.77038(11) 0.30152(15) 0.0148 1.0000 Uani . . . . . .
N7 N 0.25892(17) 0.57697(11) 0.28733(15) 0.0159 1.0000 Uani . . . . . .
N15 N 1.03817(18) 0.72723(12) 0.40098(15) 0.0166 1.0000 Uani . . . . . .
C10 C 0.5747(2) 0.67387(14) 0.65759(18) 0.0179 1.0000 Uani . . . . . .
C15 C 0.9451(2) 0.67634(13) 0.35385(18) 0.0145 1.0000 Uani . . . . . .
C3 C 0.7266(2) 0.41341(13) 0.34090(19) 0.0170 1.0000 Uani . . . . . .
C11 C 0.6317(2) 0.74724(14) 0.63739(18) 0.0173 1.0000 Uani . . . . . .
C6 C 0.6898(2) 0.55557(13) 0.04251(17) 0.0153 1.0000 Uani . . . . . .
C8 C 0.3274(2) 0.52331(13) 0.23641(17) 0.0144 1.0000 Uani . . . . . .
C4 C 0.7524(2) 0.67285(13) 0.11490(18) 0.0152 1.0000 Uani . . . . . .
C7 C 0.3509(2) 0.63168(13) 0.32746(17) 0.0131 1.0000 Uani . . . . . .
C16 C 0.9686(2) 0.78417(13) 0.44594(18) 0.0147 1.0000 Uani . . . . . .
N16 N 0.9743(2) 0.60801(13) 0.29903(18) 0.0258 1.0000 Uani . . . . . .
N8 N 0.3226(2) 0.69841(13) 0.38365(17) 0.0234 1.0000 Uani . . . . . .
C14 C 0.5580(2) 0.90008(14) 0.3419(2) 0.0198 1.0000 Uani . . . . . .
B2 B 0.7223(2) 0.81189(15) 0.4683(2) 0.0142 1.0000 Uani . . . . . .
B1 B 0.5733(2) 0.50090(15) 0.20435(19) 0.0125 1.0000 Uani . . . . . .
C9 C 0.5689(2) 0.63156(14) 0.56095(18) 0.0153 1.0000 Uani . . . . . .
C2 C 0.8032(2) 0.43000(15) 0.4334(2) 0.0218 1.0000 Uani . . . . . .
C1 C 0.7874(2) 0.51335(15) 0.45005(18) 0.0201 1.0000 Uani . . . . . .
C12 C 0.4948(2) 0.80201(15) 0.23004(19) 0.0199 1.0000 Uani . . . . . .
C13 C 0.4736(2) 0.88391(15) 0.2529(2) 0.0223 1.0000 Uani . . . . . .
C5 C 0.7609(2) 0.62408(14) 0.02482(18) 0.0172 1.0000 Uani . . . . . .
H101 H 0.5455 0.6562 0.7233 0.0210 1.0000 Uiso . . . . . .
H31 H 0.7161 0.3615 0.3077 0.0198 1.0000 Uiso . . . . . .
H111 H 0.6505 0.7900 0.6876 0.0201 1.0000 Uiso . . . . . .
H61 H 0.6768 0.5099 -0.0043 0.0176 1.0000 Uiso . . . . . .
H81 H 0.2909 0.4768 0.1996 0.0168 1.0000 Uiso . . . . . .
H41 H 0.7918 0.7250 0.1262 0.0181 1.0000 Uiso . . . . . .
H161 H 1.0060 0.8290 0.4863 0.0174 1.0000 Uiso . . . . . .
H141 H 0.5676 0.9511 0.3780 0.0238 1.0000 Uiso . . . . . .
H91 H 0.5346 0.5781 0.5496 0.0179 1.0000 Uiso . . . . . .
H21 H 0.8563 0.3931 0.4768 0.0254 1.0000 Uiso . . . . . .
H11 H 0.8278 0.5433 0.5091 0.0238 1.0000 Uiso . . . . . .
H121 H 0.4509 0.7727 0.1722 0.0242 1.0000 Uiso . . . . . .
H131 H 0.4139 0.9201 0.2148 0.0255 1.0000 Uiso . . . . . .
H51 H 0.8064 0.6359 -0.0360 0.0202 1.0000 Uiso . . . . . .
H1 H 0.7478 0.8642 0.5122 0.0500 1.0000 Uiso . . . . . .
H2 H 0.5547 0.4456 0.1565 0.0500 1.0000 Uiso . . . . . .
H3 H 1.0650 0.5947 0.2979 0.0500 1.0000 Uiso R . . . . .
H4 H 0.3925 0.7352 0.4074 0.0500 1.0000 Uiso R . . . . .
H5 H 0.2366 0.7129 0.4059 0.0500 1.0000 Uiso R . . . . .
H6 H 0.9116 0.5754 0.2809 0.0500 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.14891(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 . N6 . 1.9807(18) yes
Fe1 . N14 . 1.9781(19) yes
Fe1 . N10 . 1.9877(19) yes
Fe1 . N2 . 1.9860(19) yes
Fe1 . N4 . 1.9953(19) yes
Fe1 . N12 . 1.9988(19) yes
N6 . N5 . 1.386(2) yes
N6 . C7 . 1.338(3) yes
N3 . N4 . 1.374(2) yes
N3 . C6 . 1.351(3) yes
N3 . B1 . 1.548(3) yes
N14 . N13 . 1.388(3) yes
N14 . C15 . 1.338(3) yes
N1 . N2 . 1.371(3) yes
N1 . C3 . 1.353(3) yes
N1 . B1 . 1.543(3) yes
N13 . C16 . 1.327(3) yes
N13 . B2 . 1.544(3) yes
N5 . C8 . 1.333(3) yes
N5 . B1 . 1.544(3) yes
N10 . N9 . 1.370(2) yes
N10 . C9 . 1.338(3) yes
N9 . C11 . 1.347(3) yes
N9 . B2 . 1.543(3) yes
N2 . C1 . 1.344(3) yes
N4 . C4 . 1.343(3) yes
N11 . N12 . 1.373(3) yes
N11 . C14 . 1.353(3) yes
N11 . B2 . 1.545(3) yes
N12 . C12 . 1.339(3) yes
N7 . C8 . 1.338(3) yes
N7 . C7 . 1.371(3) yes
N15 . C15 . 1.368(3) yes
N15 . C16 . 1.343(3) yes
C10 . C11 . 1.381(3) yes
C10 . C9 . 1.399(3) yes
C10 . H101 . 0.956 no
C15 . N16 . 1.371(3) yes
C3 . C2 . 1.370(3) yes
C3 . H31 . 0.954 no
C11 . H111 . 0.953 no
C6 . C5 . 1.379(3) yes
C6 . H61 . 0.958 no
C8 . H81 . 0.954 no
C4 . C5 . 1.401(3) yes
C4 . H41 . 0.957 no
C7 . N8 . 1.356(3) yes
C16 . H161 . 0.957 no
N16 . H3 . 0.967 no
N16 . H6 . 0.856 no
N8 . H4 . 0.969 no
N8 . H5 . 0.991 no
C14 . C13 . 1.376(4) yes
C14 . H141 . 0.956 no
B2 . H1 . 1.045 no
B1 . H2 . 1.100 no
C9 . H91 . 0.956 no
C2 . C1 . 1.402(4) yes
C2 . H21 . 0.954 no
C1 . H11 . 0.955 no
C12 . C13 . 1.403(4) yes
C12 . H121 . 0.951 no
C13 . H131 . 0.954 no
C5 . H51 . 0.960 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N6 . Fe1 . N14 . 179.13(8) yes
N6 . Fe1 . N10 . 91.79(8) yes
N14 . Fe1 . N10 . 87.91(8) yes
N6 . Fe1 . N2 . 87.87(8) yes
N14 . Fe1 . N2 . 91.31(8) yes
N10 . Fe1 . N2 . 89.67(8) yes
N6 . Fe1 . N4 . 89.31(8) yes
N14 . Fe1 . N4 . 90.97(8) yes
N10 . Fe1 . N4 . 177.97(7) yes
N2 . Fe1 . N4 . 88.66(7) yes
N6 . Fe1 . N12 . 91.74(8) yes
N14 . Fe1 . N12 . 89.06(8) yes
N10 . Fe1 . N12 . 88.84(8) yes
N2 . Fe1 . N12 . 178.45(8) yes
N4 . Fe1 . N12 . 92.84(8) yes
Fe1 . N6 . N5 . 118.96(13) yes
Fe1 . N6 . C7 . 136.39(15) yes
N5 . N6 . C7 . 104.56(17) yes
N4 . N3 . C6 . 109.97(18) yes
N4 . N3 . B1 . 118.88(17) yes
C6 . N3 . B1 . 130.25(18) yes
Fe1 . N14 . N13 . 118.79(13) yes
Fe1 . N14 . C15 . 136.64(16) yes
N13 . N14 . C15 . 104.42(17) yes
N2 . N1 . C3 . 109.47(18) yes
N2 . N1 . B1 . 118.37(17) yes
C3 . N1 . B1 . 132.15(19) yes
N14 . N13 . C16 . 107.66(17) yes
N14 . N13 . B2 . 118.85(16) yes
C16 . N13 . B2 . 133.21(19) yes
N6 . N5 . C8 . 107.52(17) yes
N6 . N5 . B1 . 118.80(17) yes
C8 . N5 . B1 . 133.60(19) yes
Fe1 . N10 . N9 . 119.81(13) yes
Fe1 . N10 . C9 . 133.95(15) yes
N9 . N10 . C9 . 106.22(17) yes
N10 . N9 . C11 . 110.04(17) yes
N10 . N9 . B2 . 118.22(17) yes
C11 . N9 . B2 . 131.72(19) yes
N1 . N2 . Fe1 . 119.76(14) yes
N1 . N2 . C1 . 106.22(18) yes
Fe1 . N2 . C1 . 133.90(16) yes
N3 . N4 . Fe1 . 118.97(13) yes
N3 . N4 . C4 . 106.07(17) yes
Fe1 . N4 . C4 . 134.27(15) yes
N12 . N11 . C14 . 109.30(19) yes
N12 . N11 . B2 . 118.54(17) yes
C14 . N11 . B2 . 131.8(2) yes
N11 . N12 . Fe1 . 119.12(14) yes
N11 . N12 . C12 . 106.53(19) yes
Fe1 . N12 . C12 . 133.69(16) yes
C8 . N7 . C7 . 103.25(18) yes
C15 . N15 . C16 . 103.10(18) yes
C11 . C10 . C9 . 105.0(2) yes
C11 . C10 . H101 . 127.3 no
C9 . C10 . H101 . 127.7 no
N15 . C15 . N14 . 112.78(19) yes
N15 . C15 . N16 . 122.7(2) yes
N14 . C15 . N16 . 124.5(2) yes
N1 . C3 . C2 . 109.0(2) yes
N1 . C3 . H31 . 125.3 no
C2 . C3 . H31 . 125.7 no
C10 . C11 . N9 . 108.27(19) yes
C10 . C11 . H111 . 126.0 no
N9 . C11 . H111 . 125.7 no
N3 . C6 . C5 . 108.34(19) yes
N3 . C6 . H61 . 125.5 no
C5 . C6 . H61 . 126.1 no
N7 . C8 . N5 . 112.04(19) yes
N7 . C8 . H81 . 124.1 no
N5 . C8 . H81 . 123.8 no
N4 . C4 . C5 . 110.5(2) yes
N4 . C4 . H41 . 124.4 no
C5 . C4 . H41 . 125.2 no
N7 . C7 . N6 . 112.62(19) yes
N7 . C7 . N8 . 123.20(19) yes
N6 . C7 . N8 . 124.2(2) yes
N15 . C16 . N13 . 112.04(19) yes
N15 . C16 . H161 . 124.0 no
N13 . C16 . H161 . 124.0 no
C15 . N16 . H3 . 117.3 no
C15 . N16 . H6 . 116.7 no
H3 . N16 . H6 . 124.5 no
C7 . N8 . H4 . 118.4 no
C7 . N8 . H5 . 126.3 no
H4 . N8 . H5 . 115.3 no
N11 . C14 . C13 . 108.9(2) yes
N11 . C14 . H141 . 125.3 no
C13 . C14 . H141 . 125.8 no
N11 . B2 . N13 . 108.22(18) yes
N11 . B2 . N9 . 107.08(17) yes
N13 . B2 . N9 . 106.63(17) yes
N11 . B2 . H1 . 110.8 no
N13 . B2 . H1 . 111.6 no
N9 . B2 . H1 . 112.2 no
N3 . B1 . N5 . 107.57(17) yes
N3 . B1 . N1 . 106.53(17) yes
N5 . B1 . N1 . 107.34(17) yes
N3 . B1 . H2 . 108.7 no
N5 . B1 . H2 . 116.0 no
N1 . B1 . H2 . 110.2 no
C10 . C9 . N10 . 110.50(19) yes
C10 . C9 . H91 . 125.0 no
N10 . C9 . H91 . 124.5 no
C3 . C2 . C1 . 104.9(2) yes
C3 . C2 . H21 . 127.7 no
C1 . C2 . H21 . 127.5 no
C2 . C1 . N2 . 110.4(2) yes
C2 . C1 . H11 . 125.1 no
N2 . C1 . H11 . 124.4 no
N12 . C12 . C13 . 110.5(2) yes
N12 . C12 . H121 . 124.5 no
C13 . C12 . H121 . 125.0 no
C12 . C13 . C14 . 104.7(2) yes
C12 . C13 . H131 . 127.3 no
C14 . C13 . H131 . 128.0 no
C4 . C5 . C6 . 105.14(19) yes
C4 . C5 . H51 . 127.3 no
C6 . C5 . H51 . 127.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N16 . H3 . N7 1_655 174 0.97 2.05 3.012(3) yes
N8 . H4 . N12 . 125 0.97 2.58 3.234(3) yes
N8 . H5 . N15 1_455 160 0.99 2.06 3.016(3) yes
N16 . H6 . N2 . 130 0.86 2.56 3.182(3) yes


####################################################################### 
# 
# 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_OH184-393K
_database_code_depnum_ccdc_archive 'CCDC 2370862'
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;


_cell_length_a                   10.6457(2)
_cell_length_b                   16.6839(5)
_cell_length_c                   13.0720(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.662(2)
_cell_angle_gamma                90
_cell_volume                     2314.06(10)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0030 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0060 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Fe 0.3460 0.8440 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805
1.0369 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0010 0.0010 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C64 H80 B8 Fe4 N64 
# Dc =      5.90 Fooo =   4224.00 Mu =     27.75 M =   2055.67
# Found Formula = C16 H20 B2 Fe1 N16 
# Dc =      1.48 FOOO =   1056.00 Mu =      6.94 M =    513.92

_chemical_formula_sum            'C16 H20 B2 Fe N16'
_chemical_formula_moiety         'C16 H20 B2 Fe N16'
_chemical_compound_source        .
_chemical_formula_weight         513.92


_cell_measurement_reflns_used    7649
_cell_measurement_theta_min      4.29
_cell_measurement_theta_max      76.39
_cell_measurement_temperature    393

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_max          0.110

_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    5.584

# Sheldrick geometric approximatio 0.95 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)
;
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.99

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_cell_refinement       
; 
 CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)
;
_computing_data_reduction        
; 
 CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      393
_diffrn_reflns_number            18004
_diffrn_reflns_av_unetI/netI     0.048
_reflns_number_total             4588
_diffrn_reflns_av_R_equivalents  0.031
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4588 
# Theoretical number of reflections is about 9845 


_diffrn_reflns_theta_min         4.306
_diffrn_reflns_theta_max         77.509
_diffrn_measured_fraction_theta_max 0.931

_diffrn_reflns_theta_full        66.9692
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.74
_refine_diff_density_max         0.46


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     16
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4321
_oxford_refine_ls_R_factor_ref   0.0572
_refine_ls_R_factor_all          0.0572
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_all         0.1498
_refine_ls_goodness_of_fit_ref   1.0248
_refine_ls_shift/su_max          0.0061984
_refine_ls_shift/su_mean         0.0002847


# Computed with I/sigma = -10 
_oxford_reflns_number_all        4321
_oxford_refine_ls_R_factor_all   0.0572
_oxford_refine_ls_wR_factor_all  0.1498

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3557
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_gt          0.1427


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 1.82P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Fe1 Fe 0.64597(4) 0.65709(3) 0.33801(3) 0.0468 1.0000 Uani . . . . . .
N6 N 0.4608(2) 0.61240(17) 0.3007(2) 0.0488 1.0000 Uani . . . . . .
N3 N 0.6355(2) 0.56134(17) 0.13787(19) 0.0458 1.0000 Uani . . . . . .
N14 N 0.8318(2) 0.70236(19) 0.3723(2) 0.0542 1.0000 Uani . . . . . .
N1 N 0.6559(3) 0.47748(16) 0.2962(2) 0.0483 1.0000 Uani . . . . . .
N13 N 0.8443(2) 0.76951(17) 0.4329(2) 0.0489 1.0000 Uani . . . . . .
N5 N 0.4487(2) 0.54307(16) 0.2428(2) 0.0464 1.0000 Uani . . . . . .
N10 N 0.6187(3) 0.67853(17) 0.4979(2) 0.0508 1.0000 Uani . . . . . .
N9 N 0.6630(3) 0.74903(17) 0.5401(2) 0.0498 1.0000 Uani . . . . . .
N2 N 0.6971(3) 0.53316(19) 0.3679(2) 0.0568 1.0000 Uani . . . . . .
N4 N 0.6816(3) 0.63183(17) 0.1791(2) 0.0499 1.0000 Uani . . . . . .
N11 N 0.6336(3) 0.83579(17) 0.3844(3) 0.0538 1.0000 Uani . . . . . .
N12 N 0.5880(3) 0.78108(18) 0.3134(2) 0.0548 1.0000 Uani . . . . . .
N7 N 0.2586(3) 0.5743(2) 0.2860(2) 0.0581 1.0000 Uani . . . . . .
N15 N 1.0364(3) 0.7266(2) 0.4120(3) 0.0619 1.0000 Uani . . . . . .
C10 C 0.5846(5) 0.6807(3) 0.6638(3) 0.0835 1.0000 Uani . . . . . .
H10 H 0.5580 0.6657 0.7274 0.0986 1.0000 Uiso . . . . . .
C15 C 0.9499(3) 0.6788(2) 0.3627(3) 0.0534 1.0000 Uani D . . . . .
C3 C 0.7091(4) 0.4067(2) 0.3207(3) 0.0627 1.0000 Uani . . . . . .
H31 H 0.6966 0.3593 0.2836 0.0747 1.0000 Uiso . . . . . .
C11 C 0.6425(4) 0.7506(3) 0.6394(3) 0.0672 1.0000 Uani . . . . . .
H111 H 0.6641 0.7923 0.6845 0.0814 1.0000 Uiso . . . . . .
C6 C 0.6774(4) 0.5511(2) 0.0445(3) 0.0564 1.0000 Uani . . . . . .
H61 H 0.6588 0.5077 0.0014 0.0675 1.0000 Uiso . . . . . .
C8 C 0.3284(3) 0.5227(2) 0.2364(3) 0.0536 1.0000 Uani . . . . . .
H8 H 0.2960 0.4779 0.2016 0.0643 1.0000 Uiso . . . . . .
C4 C 0.7513(4) 0.6634(2) 0.1089(3) 0.0633 1.0000 Uani . . . . . .
H41 H 0.7941 0.7118 0.1169 0.0754 1.0000 Uiso . . . . . .
C7 C 0.3445(3) 0.6282(2) 0.3247(2) 0.0470 1.0000 Uani D . . . . .
C16 C 0.9669(3) 0.7816(2) 0.4544(3) 0.0565 1.0000 Uani . . . . . .
H16 H 1.0007 0.8230 0.4952 0.0675 1.0000 Uiso . . . . . .
N16 N 0.9788(3) 0.6122(3) 0.3095(4) 0.0831 1.0000 Uani D . . . . .
H3 H 1.0635(15) 0.600(2) 0.305(4) 0.099(2) 1.0000 Uiso D . . . . .
H6 H 0.914(2) 0.5777(19) 0.287(4) 0.099(2) 1.0000 Uiso D . . . . .
N8 N 0.3149(3) 0.6931(2) 0.3801(3) 0.0680 1.0000 Uani D . . . . .
H4 H 0.3818(19) 0.7302(18) 0.410(3) 0.083(2) 1.0000 Uiso D . . . . .
H5 H 0.2324(17) 0.700(2) 0.397(3) 0.082(2) 1.0000 Uiso D . . . . .
C14 C 0.5746(4) 0.9066(2) 0.3661(4) 0.0693 1.0000 Uani . . . . . .
H14 H 0.5904 0.9535 0.4031 0.0831 1.0000 Uiso . . . . . .
B2 B 0.7279(4) 0.8104(2) 0.4738(3) 0.0519 1.0000 Uani . . . . . .
H2 H 0.7537 0.8573 0.5153 0.0627 1.0000 Uiso . . . . . .
B1 B 0.5664(4) 0.5019(2) 0.2042(3) 0.0474 1.0000 Uani . . . . . .
H1 H 0.5409 0.4544 0.1635 0.0567 1.0000 Uiso . . . . . .
C9 C 0.5730(4) 0.6376(2) 0.5733(3) 0.0665 1.0000 Uani . . . . . .
H9 H 0.5389 0.5863 0.5662 0.0787 1.0000 Uiso . . . . . .
C2 C 0.7846(4) 0.4146(3) 0.4086(3) 0.0742 1.0000 Uani . . . . . .
H21 H 0.8328 0.3755 0.4431 0.0879 1.0000 Uiso . . . . . .
C1 C 0.7736(4) 0.4929(3) 0.4344(3) 0.0710 1.0000 Uani . . . . . .
H11 H 0.8157 0.5161 0.4925 0.0860 1.0000 Uiso . . . . . .
C12 C 0.5020(4) 0.8195(3) 0.2531(3) 0.0686 1.0000 Uani . . . . . .
H12 H 0.4561 0.7968 0.1963 0.0825 1.0000 Uiso . . . . . .
C13 C 0.4888(4) 0.8980(3) 0.2842(4) 0.0811 1.0000 Uani . . . . . .
H13 H 0.4329 0.9365 0.2558 0.0967 1.0000 Uiso . . . . . .
C5 C 0.7520(4) 0.6153(3) 0.0240(3) 0.0652 1.0000 Uani . . . . . .
H51 H 0.7934 0.6245 -0.0349 0.0778 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3953(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 . N6 . 2.127(3) yes
Fe1 . N14 . 2.131(3) yes
Fe1 . N10 . 2.163(3) yes
Fe1 . N2 . 2.166(3) yes
Fe1 . N4 . 2.183(3) yes
Fe1 . N12 . 2.175(3) yes
N6 . N5 . 1.383(4) yes
N6 . C7 . 1.328(4) yes
N3 . N4 . 1.368(4) yes
N3 . C6 . 1.343(4) yes
N3 . B1 . 1.543(5) yes
N14 . N13 . 1.372(4) yes
N14 . C15 . 1.332(4) yes
N1 . N2 . 1.367(4) yes
N1 . C3 . 1.338(5) yes
N1 . B1 . 1.527(5) yes
N13 . C16 . 1.328(4) yes
N13 . B2 . 1.548(5) yes
N5 . C8 . 1.320(4) yes
N5 . B1 . 1.549(4) yes
N10 . N9 . 1.366(4) yes
N10 . C9 . 1.324(5) yes
N9 . C11 . 1.333(5) yes
N9 . B2 . 1.540(5) yes
N2 . C1 . 1.324(5) yes
N4 . C4 . 1.334(5) yes
N11 . N12 . 1.363(4) yes
N11 . C14 . 1.350(5) yes
N11 . B2 . 1.537(5) yes
N12 . C12 . 1.324(5) yes
N7 . C8 . 1.339(5) yes
N7 . C7 . 1.351(4) yes
N15 . C15 . 1.342(5) yes
N15 . C16 . 1.328(5) yes
C10 . H10 . 0.934 no
C10 . C11 . 1.370(6) yes
C10 . C9 . 1.380(6) yes
C15 . N16 . 1.360(5) yes
C3 . H31 . 0.931 no
C3 . C2 . 1.354(6) yes
C11 . H111 . 0.928 no
C6 . H61 . 0.930 no
C6 . C5 . 1.372(6) yes
C8 . H8 . 0.927 no
C4 . H41 . 0.929 no
C4 . C5 . 1.371(6) yes
C7 . N8 . 1.354(5) yes
C16 . H16 . 0.927 no
N16 . H3 . 0.932(14) no
N16 . H6 . 0.930(14) no
N8 . H4 . 0.9996(10) no
N8 . H5 . 0.931(14) no
C14 . H14 . 0.928 no
C14 . C13 . 1.357(7) yes
B2 . H2 . 0.979 no
B1 . H1 . 0.980 no
C9 . H9 . 0.931 no
C2 . H21 . 0.925 no
C2 . C1 . 1.358(7) yes
C1 . H11 . 0.934 no
C12 . H12 . 0.934 no
C12 . C13 . 1.382(7) yes
C13 . H13 . 0.932 no
C5 . H51 . 0.931 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N6 . Fe1 . N14 . 178.89(11) yes
N6 . Fe1 . N10 . 94.88(11) yes
N14 . Fe1 . N10 . 86.16(11) yes
N6 . Fe1 . N2 . 85.50(11) yes
N14 . Fe1 . N2 . 94.86(12) yes
N10 . Fe1 . N2 . 92.01(12) yes
N6 . Fe1 . N4 . 86.77(11) yes
N14 . Fe1 . N4 . 92.21(11) yes
N10 . Fe1 . N4 . 177.15(11) yes
N2 . Fe1 . N4 . 85.79(11) yes
N6 . Fe1 . N12 . 93.03(11) yes
N14 . Fe1 . N12 . 86.65(11) yes
N10 . Fe1 . N12 . 85.82(12) yes
N2 . Fe1 . N12 . 177.28(11) yes
N4 . Fe1 . N12 . 96.42(11) yes
Fe1 . N6 . N5 . 117.53(18) yes
Fe1 . N6 . C7 . 137.8(2) yes
N5 . N6 . C7 . 104.4(3) yes
N4 . N3 . C6 . 109.4(3) yes
N4 . N3 . B1 . 120.2(2) yes
C6 . N3 . B1 . 129.6(3) yes
Fe1 . N14 . N13 . 117.08(19) yes
Fe1 . N14 . C15 . 137.9(2) yes
N13 . N14 . C15 . 104.3(3) yes
N2 . N1 . C3 . 109.3(3) yes
N2 . N1 . B1 . 120.2(3) yes
C3 . N1 . B1 . 130.5(3) yes
N14 . N13 . C16 . 107.1(3) yes
N14 . N13 . B2 . 121.1(2) yes
C16 . N13 . B2 . 131.3(3) yes
N6 . N5 . C8 . 107.2(3) yes
N6 . N5 . B1 . 120.5(2) yes
C8 . N5 . B1 . 132.2(3) yes
Fe1 . N10 . N9 . 117.6(2) yes
Fe1 . N10 . C9 . 136.1(2) yes
N9 . N10 . C9 . 106.2(3) yes
N10 . N9 . C11 . 109.4(3) yes
N10 . N9 . B2 . 120.0(3) yes
C11 . N9 . B2 . 130.6(3) yes
Fe1 . N2 . N1 . 117.6(2) yes
Fe1 . N2 . C1 . 137.3(3) yes
N1 . N2 . C1 . 104.6(3) yes
Fe1 . N4 . N3 . 117.14(19) yes
Fe1 . N4 . C4 . 136.7(3) yes
N3 . N4 . C4 . 105.7(3) yes
N12 . N11 . C14 . 109.3(3) yes
N12 . N11 . B2 . 120.5(3) yes
C14 . N11 . B2 . 129.9(3) yes
Fe1 . N12 . N11 . 117.1(2) yes
Fe1 . N12 . C12 . 136.3(3) yes
N11 . N12 . C12 . 105.8(3) yes
C8 . N7 . C7 . 102.9(3) yes
C15 . N15 . C16 . 103.1(3) yes
H10 . C10 . C11 . 127.6 no
H10 . C10 . C9 . 127.6 no
C11 . C10 . C9 . 104.7(3) yes
N15 . C15 . N14 . 113.3(3) yes
N15 . C15 . N16 . 123.8(3) yes
N14 . C15 . N16 . 123.0(3) yes
N1 . C3 . H31 . 125.8 no
N1 . C3 . C2 . 109.1(4) yes
H31 . C3 . C2 . 125.1 no
C10 . C11 . N9 . 108.8(3) yes
C10 . C11 . H111 . 125.6 no
N9 . C11 . H111 . 125.6 no
N3 . C6 . H61 . 125.5 no
N3 . C6 . C5 . 108.6(3) yes
H61 . C6 . C5 . 125.9 no
N7 . C8 . N5 . 112.2(3) yes
N7 . C8 . H8 . 123.8 no
N5 . C8 . H8 . 124.0 no
N4 . C4 . H41 . 124.1 no
N4 . C4 . C5 . 111.5(4) yes
H41 . C4 . C5 . 124.4 no
N7 . C7 . N6 . 113.3(3) yes
N7 . C7 . N8 . 123.6(3) yes
N6 . C7 . N8 . 123.1(3) yes
N15 . C16 . N13 . 112.2(3) yes
N15 . C16 . H16 . 123.4 no
N13 . C16 . H16 . 124.4 no
C15 . N16 . H3 . 118.4(17) no
C15 . N16 . H6 . 118.4(17) no
H3 . N16 . H6 . 123(3) no
C7 . N8 . H4 . 121.1(16) no
C7 . N8 . H5 . 119.8(17) no
H4 . N8 . H5 . 119(2) no
N11 . C14 . H14 . 125.6 no
N11 . C14 . C13 . 108.7(4) yes
H14 . C14 . C13 . 125.7 no
N13 . B2 . N9 . 108.1(3) yes
N13 . B2 . N11 . 110.5(3) yes
N9 . B2 . N11 . 108.4(3) yes
N13 . B2 . H2 . 110.3 no
N9 . B2 . H2 . 109.8 no
N11 . B2 . H2 . 109.7 no
N5 . B1 . N3 . 109.5(3) yes
N5 . B1 . N1 . 109.4(3) yes
N3 . B1 . N1 . 108.6(3) yes
N5 . B1 . H1 . 109.8 no
N3 . B1 . H1 . 109.7 no
N1 . B1 . H1 . 109.8 no
C10 . C9 . N10 . 110.9(3) yes
C10 . C9 . H9 . 124.8 no
N10 . C9 . H9 . 124.3 no
C3 . C2 . H21 . 127.8 no
C3 . C2 . C1 . 104.4(4) yes
H21 . C2 . C1 . 127.8 no
C2 . C1 . N2 . 112.7(4) yes
C2 . C1 . H11 . 123.7 no
N2 . C1 . H11 . 123.6 no
N12 . C12 . H12 . 124.7 no
N12 . C12 . C13 . 111.4(4) yes
H12 . C12 . C13 . 123.9 no
C12 . C13 . C14 . 104.8(4) yes
C12 . C13 . H13 . 127.8 no
C14 . C13 . H13 . 127.5 no
C6 . C5 . C4 . 104.9(3) yes
C6 . C5 . H51 . 127.7 no
C4 . C5 . H51 . 127.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N16 . H3 . N7 1_655 176(5) 0.932(14) 2.153(15) 3.084(6) yes
N8 . H5 . N15 1_455 171(4) 0.931(14) 2.156(16) 3.079(6) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 6 15 x .
####################################################################### 
# 
# 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_OH184-320K
_database_code_depnum_ccdc_archive 'CCDC 2370864'
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 B2 Fe N16'
_chemical_formula_sum            'C16 H20 B2 Fe N16'
_chemical_formula_weight         513.95

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.5951(7)
_cell_length_b                   16.5995(9)
_cell_length_c                   12.9503(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.867(6)
_cell_angle_gamma                90
_cell_volume                     2269.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    320(2)
_cell_measurement_reflns_used    2592
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      21.86

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            blue

_exptl_crystal_density_diffrn    1.504
_exptl_crystal_F_000             1056

_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_T_max  0.7460

_diffrn_ambient_temperature      320(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'micro-focus tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            23801
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_sigmaI/netI    0.1264
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         29.94
_reflns_number_total             6560
_reflns_number_gt                3194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.8399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6560
_refine_ls_number_parameters     316
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1683
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.64592(5) 0.65727(3) 0.33751(4) 0.03068(16) Uani 1 1 d . . .
N6 N 0.4620(3) 0.61263(16) 0.3007(2) 0.0356(7) Uani 1 1 d . . .
N3 N 0.6362(3) 0.56148(17) 0.1372(2) 0.0339(7) Uani 1 1 d . . .
N14 N 0.8309(3) 0.70239(18) 0.3721(2) 0.0390(7) Uani 1 1 d . . .
N1 N 0.6572(3) 0.47801(17) 0.2968(2) 0.0384(7) Uani 1 1 d . . .
N13 N 0.8436(3) 0.77039(17) 0.4329(2) 0.0360(7) Uani 1 1 d . . .
N5 N 0.4492(3) 0.54287(17) 0.2425(2) 0.0355(7) Uani 1 1 d . . .
N10 N 0.6189(3) 0.67827(17) 0.4962(2) 0.0404(8) Uani 1 1 d . . .
N9 N 0.6618(3) 0.74901(17) 0.5398(2) 0.0381(7) Uani 1 1 d . . .
N2 N 0.6986(3) 0.53514(19) 0.3688(2) 0.0442(8) Uani 1 1 d . . .
N4 N 0.6818(3) 0.63235(17) 0.1794(2) 0.0377(7) Uani 1 1 d . . .
N11 N 0.6324(3) 0.83582(18) 0.3825(3) 0.0422(8) Uani 1 1 d . . .
N12 N 0.5872(3) 0.78041(19) 0.3120(3) 0.0430(8) Uani 1 1 d . . .
N7 N 0.2583(3) 0.5745(2) 0.2865(3) 0.0449(8) Uani 1 1 d . . .
N15 N 1.0373(3) 0.7267(2) 0.4116(3) 0.0465(8) Uani 1 1 d . . .
C10 C 0.5834(5) 0.6798(3) 0.6635(3) 0.0615(13) Uani 1 1 d . . .
H10 H 0.5576 0.6641 0.7273 0.074 Uiso 1 1 calc R . .
C15 C 0.9487(3) 0.6787(2) 0.3621(3) 0.0397(9) Uani 1 1 d . . .
C3 C 0.7122(4) 0.4070(2) 0.3231(4) 0.0525(11) Uani 1 1 d . . .
H3A H 0.7004 0.3592 0.2863 0.063 Uiso 1 1 calc R . .
C11 C 0.6408(4) 0.7504(2) 0.6401(3) 0.0519(11) Uani 1 1 d . . .
H11 H 0.6616 0.7922 0.6861 0.062 Uiso 1 1 calc R . .
C6 C 0.6795(4) 0.5516(2) 0.0435(3) 0.0430(9) Uani 1 1 d . . .
H6A H 0.6621 0.5080 -0.0004 0.052 Uiso 1 1 calc R . .
C8 C 0.3280(4) 0.5224(2) 0.2371(3) 0.0423(9) Uani 1 1 d . . .
H8 H 0.2950 0.4769 0.2027 0.051 Uiso 1 1 calc R . .
C4 C 0.7517(4) 0.6646(2) 0.1090(3) 0.0497(10) Uani 1 1 d . . .
H4A H 0.7940 0.7136 0.1171 0.060 Uiso 1 1 calc R . .
C7 C 0.3449(3) 0.6286(2) 0.3254(3) 0.0357(8) Uani 1 1 d . . .
C16 C 0.9666(3) 0.7821(2) 0.4544(3) 0.0422(9) Uani 1 1 d . . .
H16 H 1.0002 0.8245 0.4949 0.051 Uiso 1 1 calc R . .
N16 N 0.9787(3) 0.6108(2) 0.3081(3) 0.0664(11) Uani 1 1 d D . .
H3 H 1.0650 0.5947 0.2979 0.080 Uiso 1 1 d D . .
H6 H 0.9116 0.5754 0.2809 0.080 Uiso 1 1 d D . .
N8 N 0.3221(2) 0.69719(17) 0.3831(3) 0.0587(10) Uani 1 1 d D . .
H4 H 0.3925 0.7352 0.4074 0.070 Uiso 1 1 d D . .
H5 H 0.2365 0.7129 0.4059 0.070 Uiso 1 1 d D . .
C14 C 0.5722(4) 0.9061(2) 0.3627(4) 0.0569(12) Uani 1 1 d . . .
H14 H 0.5870 0.9534 0.4001 0.068 Uiso 1 1 calc R . .
B2 B 0.7267(4) 0.8114(3) 0.4739(3) 0.0386(10) Uani 1 1 d . . .
H2 H 0.7525 0.8587 0.5159 0.046 Uiso 1 1 calc R . .
B1 B 0.5669(4) 0.5017(2) 0.2038(3) 0.0377(10) Uani 1 1 d . . .
H1 H 0.5415 0.4538 0.1629 0.045 Uiso 1 1 calc R . .
C9 C 0.5722(4) 0.6372(2) 0.5725(3) 0.0494(11) Uani 1 1 d . . .
H9 H 0.5365 0.5861 0.5651 0.059 Uiso 1 1 calc R . .
C2 C 0.7872(5) 0.4167(3) 0.4116(4) 0.0628(13) Uani 1 1 d . . .
H2A H 0.8357 0.3775 0.4476 0.075 Uiso 1 1 calc R . .
C1 C 0.7768(4) 0.4970(3) 0.4377(3) 0.0596(12) Uani 1 1 d . . .
H1A H 0.8190 0.5211 0.4956 0.071 Uiso 1 1 calc R . .
C12 C 0.4991(4) 0.8178(3) 0.2488(4) 0.0581(12) Uani 1 1 d . . .
H12 H 0.4531 0.7941 0.1925 0.070 Uiso 1 1 calc R . .
C13 C 0.4869(4) 0.8970(3) 0.2800(4) 0.0671(14) Uani 1 1 d . . .
H13 H 0.4317 0.9358 0.2503 0.081 Uiso 1 1 calc R . .
C5 C 0.7533(4) 0.6164(3) 0.0233(3) 0.0510(11) Uani 1 1 d . . .
H5A H 0.7953 0.6257 -0.0358 0.061 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
Fe1 N6 2.102(3) . ?
Fe1 N14 2.110(3) . ?
Fe1 N10 2.127(3) . ?
Fe1 N2 2.132(3) . ?
Fe1 N12 2.154(3) . ?
Fe1 N4 2.154(3) . ?
N6 C7 1.334(4) . ?
N6 N5 1.382(4) . ?
N3 C6 1.343(4) . ?
N3 N4 1.368(4) . ?
N3 B1 1.542(5) . ?
N14 C15 1.326(4) . ?
N14 N13 1.376(4) . ?
N1 C3 1.345(5) . ?
N1 N2 1.376(4) . ?
N1 B1 1.524(5) . ?
N13 C16 1.324(4) . ?
N13 B2 1.547(5) . ?
N5 C8 1.325(4) . ?
N5 B1 1.542(5) . ?
N10 C9 1.330(5) . ?
N10 N9 1.364(4) . ?
N9 C11 1.336(5) . ?
N9 B2 1.540(5) . ?
N2 C1 1.326(5) . ?
N4 C4 1.334(5) . ?
N11 C14 1.343(5) . ?
N11 N12 1.355(4) . ?
N11 B2 1.537(6) . ?
N12 C12 1.340(5) . ?
N7 C8 1.334(5) . ?
N7 C7 1.351(5) . ?
N15 C16 1.336(5) . ?
N15 C15 1.351(5) . ?
C10 C11 1.365(6) . ?
C10 C9 1.371(6) . ?
C15 N16 1.377(5) . ?
C3 C2 1.347(6) . ?
C6 C5 1.368(5) . ?
C4 C5 1.370(6) . ?
C7 N8 1.393(4) . ?
C14 C13 1.350(7) . ?
C2 C1 1.383(7) . ?
C12 C13 1.385(7) . ?

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
N6 Fe1 N14 179.16(12) . . ?
N6 Fe1 N10 94.52(12) . . ?
N14 Fe1 N10 86.29(12) . . ?
N6 Fe1 N2 86.02(12) . . ?
N14 Fe1 N2 94.22(12) . . ?
N10 Fe1 N2 91.53(12) . . ?
N6 Fe1 N12 92.84(11) . . ?
N14 Fe1 N12 86.95(12) . . ?
N10 Fe1 N12 86.11(12) . . ?
N2 Fe1 N12 177.29(12) . . ?
N6 Fe1 N4 87.24(11) . . ?
N14 Fe1 N4 91.97(12) . . ?
N10 Fe1 N4 177.02(12) . . ?
N2 Fe1 N4 86.19(12) . . ?
N12 Fe1 N4 96.21(12) . . ?
C7 N6 N5 104.4(3) . . ?
C7 N6 Fe1 137.6(2) . . ?
N5 N6 Fe1 117.7(2) . . ?
C6 N3 N4 109.2(3) . . ?
C6 N3 B1 130.0(3) . . ?
N4 N3 B1 120.0(3) . . ?
C15 N14 N13 104.6(3) . . ?
C15 N14 Fe1 137.6(3) . . ?
N13 N14 Fe1 117.2(2) . . ?
C3 N1 N2 109.0(3) . . ?
C3 N1 B1 130.9(4) . . ?
N2 N1 B1 120.0(3) . . ?
C16 N13 N14 106.7(3) . . ?
C16 N13 B2 131.7(3) . . ?
N14 N13 B2 121.0(3) . . ?
C8 N5 N6 107.0(3) . . ?
C8 N5 B1 132.6(3) . . ?
N6 N5 B1 120.3(3) . . ?
C9 N10 N9 105.4(3) . . ?
C9 N10 Fe1 136.3(3) . . ?
N9 N10 Fe1 118.3(2) . . ?
C11 N9 N10 109.9(3) . . ?
C11 N9 B2 130.3(3) . . ?
N10 N9 B2 119.9(3) . . ?
C1 N2 N1 105.8(3) . . ?
C1 N2 Fe1 136.1(3) . . ?
N1 N2 Fe1 117.6(2) . . ?
C4 N4 N3 105.7(3) . . ?
C4 N4 Fe1 136.5(3) . . ?
N3 N4 Fe1 117.4(2) . . ?
C14 N11 N12 109.0(4) . . ?
C14 N11 B2 130.0(4) . . ?
N12 N11 B2 120.7(3) . . ?
C12 N12 N11 106.6(3) . . ?
C12 N12 Fe1 135.3(3) . . ?
N11 N12 Fe1 117.4(2) . . ?
C8 N7 C7 103.0(3) . . ?
C16 N15 C15 102.2(3) . . ?
C11 C10 C9 105.1(4) . . ?
N14 C15 N15 113.6(3) . . ?
N14 C15 N16 123.5(3) . . ?
N15 C15 N16 122.9(3) . . ?
N1 C3 C2 108.9(4) . . ?
N9 C11 C10 108.4(3) . . ?
N3 C6 C5 108.8(4) . . ?
N5 C8 N7 112.5(3) . . ?
N4 C4 C5 111.4(4) . . ?
N6 C7 N7 113.2(3) . . ?
N6 C7 N8 119.9(3) . . ?
N7 C7 N8 126.9(3) . . ?
N13 C16 N15 112.8(3) . . ?
N11 C14 C13 109.3(4) . . ?
N11 B2 N9 108.2(3) . . ?
N11 B2 N13 109.8(3) . . ?
N9 B2 N13 107.6(3) . . ?
N1 B1 N3 108.1(3) . . ?
N1 B1 N5 109.2(3) . . ?
N3 B1 N5 109.4(3) . . ?
N10 C9 C10 111.3(4) . . ?
C3 C2 C1 105.6(4) . . ?
N2 C1 C2 110.7(4) . . ?
N12 C12 C13 109.8(4) . . ?
C14 C13 C12 105.3(4) . . ?
C6 C5 C4 104.9(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
C11 H11 N7 0.93 2.72 3.634(5) 166.7 4_676
N16 H3 N7 0.973(3) 2.093(3) 3.059(4) 172.2(2) 1_655
N16 H6 N2 0.965(3) 2.697(3) 3.376(5) 127.8(2) .
N8 H4 N10 1.01 2.739(3) 3.369(4) 120.9(2) .
N8 H4 N12 1.01 2.604(3) 3.329(4) 128.9(2) .
N8 H5 N15 1.011(3) 2.131(3) 3.110(4) 162.36(17) 1_455
C2 H2A N15 0.93 2.78 3.693(6) 169.0 3_766

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.94
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_OH184AMB
_database_code_depnum_ccdc_archive 'CCDC 2370863'
_audit_update_record             
;
2024-09-10 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 B2 Fe N16'
_chemical_formula_weight         513.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3460 0.8440 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0010 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.547(3)
_cell_length_b                   16.596(4)
_cell_length_c                   12.943(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.213(10)
_cell_angle_gamma                90
_cell_volume                     2256.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.50

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            blue

_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             1056

_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_T_max  0.7431

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'micro-focus tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            60354
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.001
_diffrn_reflns_theta_max         29.158
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5730
_reflns_number_gt                3909
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+1.8114P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5730
_refine_ls_number_parameters     310
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.096
_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
C1 C 0.7782(9) 0.4885(4) 0.4356(8) 0.0400(12) Uani 0.53 1 d . . P A 1
H1 H 0.822521 0.507900 0.495888 0.048 Uiso 0.53 1 calc R U P A 1
C2 C 0.7836(8) 0.4094(4) 0.4045(6) 0.0400(12) Uani 0.53 1 d . . P A 1
H2 H 0.830386 0.367765 0.437579 0.048 Uiso 0.53 1 calc R U P A 1
C3 C 0.7059(9) 0.4051(8) 0.3153(6) 0.0400(12) Uani 0.53 1 d . . P A 1
H3 H 0.688489 0.359720 0.274381 0.048 Uiso 0.53 1 calc R U P A 1
C1B C 0.7803(10) 0.5133(4) 0.4456(9) 0.0400(12) Uani 0.47 1 d . . P A 2
H1B H 0.817612 0.544468 0.499850 0.048 Uiso 0.47 1 calc R U P A 2
C2B C 0.7978(9) 0.4309(5) 0.4289(6) 0.0400(12) Uani 0.47 1 d . . P A 2
H2B H 0.849065 0.395785 0.470198 0.048 Uiso 0.47 1 calc R U P A 2
C3B C 0.7248(10) 0.4127(9) 0.3402(7) 0.0400(12) Uani 0.47 1 d . . P A 2
H3B H 0.719246 0.361473 0.311055 0.048 Uiso 0.47 1 calc R U P A 2
C4 C 0.7522(3) 0.66576(19) 0.1104(3) 0.0485(8) Uani 1 1 d . . . . .
H4A H 0.794056 0.714929 0.119071 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7547(3) 0.6173(2) 0.0238(2) 0.0517(8) Uani 1 1 d . . . . .
H5A H 0.796897 0.626843 -0.035088 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6816(3) 0.55235(18) 0.0437(2) 0.0424(7) Uani 1 1 d . . . . .
H6A H 0.664839 0.508555 -0.000268 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3459(2) 0.62904(16) 0.3250(2) 0.0349(6) Uani 1 1 d . . . . .
C8 C 0.3280(3) 0.52264(17) 0.2366(2) 0.0393(6) Uani 1 1 d . . . . .
H8 H 0.294378 0.477363 0.201709 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5717(3) 0.63638(18) 0.5698(2) 0.0467(7) Uani 1 1 d . . . . .
H9 H 0.536471 0.585150 0.561581 0.056 Uiso 1 1 calc R U . . .
C10 C 0.5817(3) 0.6789(2) 0.6621(2) 0.0575(9) Uani 1 1 d . . . . .
H10 H 0.555292 0.662907 0.725542 0.069 Uiso 1 1 calc R U . . .
C11 C 0.6389(3) 0.74972(19) 0.6392(2) 0.0489(8) Uani 1 1 d . . . . .
H11 H 0.659424 0.791513 0.685613 0.059 Uiso 1 1 calc R U . . .
C15 C 0.9487(3) 0.67852(17) 0.3607(2) 0.0381(6) Uani 1 1 d . . . . .
C16 C 0.9669(3) 0.78284(17) 0.4524(2) 0.0410(7) Uani 1 1 d . . . . .
H16 H 1.000885 0.825643 0.492139 0.049 Uiso 1 1 calc R U . . .
N1 N 0.6595(2) 0.47897(13) 0.29816(18) 0.0374(5) Uani 1 1 d . . . . .
N2 N 0.7003(2) 0.53688(15) 0.36876(18) 0.0426(6) Uani 1 1 d . . . . .
N3 N 0.6375(2) 0.56193(13) 0.13754(17) 0.0333(5) Uani 1 1 d . . . . .
N4 N 0.6817(2) 0.63282(13) 0.18011(18) 0.0376(5) Uani 1 1 d . . . . .
N5 N 0.4500(2) 0.54272(13) 0.24242(17) 0.0338(5) Uani 1 1 d . . . . .
N6 N 0.4635(2) 0.61249(13) 0.30055(18) 0.0350(5) Uani 1 1 d . . . . .
N7 N 0.2585(2) 0.57466(15) 0.28648(19) 0.0429(6) Uani 1 1 d . . . . .
N8 N 0.3175(2) 0.69497(16) 0.3808(2) 0.0531(7) Uani 1 1 d . . . . .
H4 H 0.392488 0.735220 0.407407 0.064 Uiso 1 1 d . U . . .
H5 H 0.236539 0.712910 0.405920 0.064 Uiso 1 1 d . U . . .
N9 N 0.6608(2) 0.74895(13) 0.53844(17) 0.0356(5) Uani 1 1 d . . . . .
N10 N 0.6187(2) 0.67795(13) 0.49461(17) 0.0365(5) Uani 1 1 d . . . . .
N11 N 0.6309(2) 0.83487(13) 0.3801(2) 0.0399(5) Uani 1 1 d D . . . .
N12 N 0.5867(2) 0.77798(15) 0.30967(18) 0.0414(6) Uani 1 1 d D . . . .
N13 N 0.84342(19) 0.77039(13) 0.43189(17) 0.0345(5) Uani 1 1 d . . . . .
N14 N 0.8298(2) 0.70193(14) 0.37150(18) 0.0377(5) Uani 1 1 d . . . . .
N15 N 1.0376(2) 0.72718(15) 0.4096(2) 0.0443(6) Uani 1 1 d . . . . .
N16 N 0.9781(2) 0.61067(17) 0.3075(2) 0.0617(8) Uani 1 1 d . . . . .
H3C H 1.065042 0.594666 0.297920 0.074 Uiso 1 1 d . U . . .
H6 H 0.911600 0.575430 0.280920 0.074 Uiso 1 1 d . U . . .
Fe1 Fe 0.64634(3) 0.65724(2) 0.33685(3) 0.02820(11) Uani 1 1 d . . . . .
B1 B 0.5683(3) 0.50141(18) 0.2037(3) 0.0355(7) Uani 1 1 d . . . . .
H1C H 0.543251 0.453264 0.163009 0.043 Uiso 1 1 calc R U . . .
B2 B 0.7258(3) 0.81127(19) 0.4723(3) 0.0372(7) Uani 1 1 d . . . . .
H2C H 0.751442 0.858844 0.513983 0.045 Uiso 1 1 calc R U . . .
C12 C 0.4964(9) 0.8259(5) 0.2535(8) 0.0408(11) Uani 0.48 1 d . . P B 1
H12 H 0.445454 0.806737 0.196350 0.049 Uiso 0.48 1 calc R U P B 1
C13 C 0.4885(8) 0.9046(5) 0.2894(6) 0.0408(11) Uani 0.48 1 d . . P B 1
H13 H 0.434898 0.945424 0.262237 0.049 Uiso 0.48 1 calc R U P B 1
C14 C 0.5772(9) 0.9089(6) 0.3741(7) 0.0408(11) Uani 0.48 1 d . . P B 1
H14 H 0.596080 0.952804 0.417395 0.049 Uiso 0.48 1 calc R U P B 1
C13B C 0.4810(7) 0.8838(4) 0.2608(5) 0.0408(11) Uani 0.52 1 d D . P B 2
H13B H 0.423534 0.919121 0.225923 0.049 Uiso 0.52 1 calc R U P B 2
C14B C 0.5623(8) 0.9007(5) 0.3449(5) 0.0408(11) Uani 0.52 1 d D . P B 2
H14B H 0.570565 0.951361 0.375388 0.049 Uiso 0.52 1 calc R U P B 2
C12B C 0.5002(8) 0.8042(4) 0.2370(7) 0.0408(11) Uani 0.52 1 d D . P B 2
H12B H 0.460802 0.775091 0.181654 0.049 Uiso 0.52 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(8) . ?
C1 N2 1.393(9) . ?
C2 C3 1.355(9) . ?
C3 N1 1.331(12) . ?
C1B N2 1.305(12) . ?
C1B C2B 1.399(9) . ?
C2B C3B 1.357(10) . ?
C3B N1 1.382(12) . ?
C4 N4 1.337(4) . ?
C4 C5 1.382(5) . ?
C5 C6 1.363(4) . ?
C6 N3 1.349(3) . ?
C7 N6 1.337(3) . ?
C7 N7 1.352(4) . ?
C7 N8 1.359(4) . ?
C8 N5 1.325(3) . ?
C8 N7 1.336(4) . ?
C9 N10 1.326(4) . ?
C9 C10 1.383(4) . ?
C10 C11 1.365(4) . ?
C11 N9 1.345(4) . ?
C15 N14 1.333(3) . ?
C15 N15 1.351(4) . ?
C15 N16 1.370(4) . ?
C16 N13 1.321(3) . ?
C16 N15 1.338(4) . ?
N1 N2 1.368(3) . ?
N1 B1 1.532(4) . ?
N2 Fe1 2.107(2) . ?
N3 N4 1.363(3) . ?
N3 B1 1.545(4) . ?
N4 Fe1 2.134(2) . ?
N5 N6 1.381(3) . ?
N5 B1 1.547(4) . ?
N6 Fe1 2.080(2) . ?
N9 N10 1.364(3) . ?
N9 B2 1.542(4) . ?
N10 Fe1 2.117(2) . ?
N11 C14 1.352(10) . ?
N11 N12 1.364(3) . ?
N11 C14B 1.365(7) . ?
N11 B2 1.538(4) . ?
N12 C12B 1.323(7) . ?
N12 C12 1.393(9) . ?
N12 Fe1 2.120(3) . ?
N13 N14 1.379(3) . ?
N13 B2 1.547(4) . ?
N14 Fe1 2.082(2) . ?
C12 C13 1.392(9) . ?
C13 C14 1.377(9) . ?
C13B C14B 1.352(7) . ?
C13B C12B 1.376(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N2 114.0(8) . . ?
C3 C2 C1 105.1(6) . . ?
N1 C3 C2 106.2(8) . . ?
N2 C1B C2B 105.1(8) . . ?
C3B C2B C1B 106.0(7) . . ?
C2B C3B N1 112.3(9) . . ?
N4 C4 C5 111.3(3) . . ?
C6 C5 C4 104.7(3) . . ?
N3 C6 C5 108.9(3) . . ?
N6 C7 N7 113.1(2) . . ?
N6 C7 N8 123.0(3) . . ?
N7 C7 N8 123.9(2) . . ?
N5 C8 N7 112.5(2) . . ?
N10 C9 C10 111.3(3) . . ?
C11 C10 C9 104.6(3) . . ?
N9 C11 C10 108.7(3) . . ?
N14 C15 N15 113.3(2) . . ?
N14 C15 N16 123.4(3) . . ?
N15 C15 N16 123.2(2) . . ?
N13 C16 N15 112.7(3) . . ?
C3 N1 N2 116.5(4) . . ?
N2 N1 C3B 100.4(5) . . ?
C3 N1 B1 123.5(4) . . ?
N2 N1 B1 119.9(2) . . ?
C3B N1 B1 139.6(5) . . ?
C1B N2 N1 116.1(4) . . ?
N1 N2 C1 98.1(4) . . ?
C1B N2 Fe1 125.3(4) . . ?
N1 N2 Fe1 118.17(17) . . ?
C1 N2 Fe1 143.3(4) . . ?
C6 N3 N4 109.4(2) . . ?
C6 N3 B1 129.9(2) . . ?
N4 N3 B1 119.9(2) . . ?
C4 N4 N3 105.7(2) . . ?
C4 N4 Fe1 136.0(2) . . ?
N3 N4 Fe1 117.72(16) . . ?
C8 N5 N6 107.1(2) . . ?
C8 N5 B1 132.7(2) . . ?
N6 N5 B1 120.1(2) . . ?
C7 N6 N5 104.4(2) . . ?
C7 N6 Fe1 137.29(18) . . ?
N5 N6 Fe1 118.07(15) . . ?
C8 N7 C7 103.0(2) . . ?
C11 N9 N10 109.5(2) . . ?
C11 N9 B2 131.0(2) . . ?
N10 N9 B2 119.5(2) . . ?
C9 N10 N9 105.9(2) . . ?
C9 N10 Fe1 135.83(19) . . ?
N9 N10 Fe1 118.25(16) . . ?
C14 N11 N12 118.4(4) . . ?
N12 N11 C14B 101.1(4) . . ?
C14 N11 B2 121.0(4) . . ?
N12 N11 B2 120.1(2) . . ?
C14B N11 B2 138.6(4) . . ?
C12B N12 N11 114.8(4) . . ?
N11 N12 C12 97.4(4) . . ?
C12B N12 Fe1 127.2(3) . . ?
N11 N12 Fe1 117.71(17) . . ?
C12 N12 Fe1 143.5(4) . . ?
C16 N13 N14 107.0(2) . . ?
C16 N13 B2 132.1(2) . . ?
N14 N13 B2 120.5(2) . . ?
C15 N14 N13 104.4(2) . . ?
C15 N14 Fe1 137.61(19) . . ?
N13 N14 Fe1 117.55(15) . . ?
C16 N15 C15 102.5(2) . . ?
N6 Fe1 N14 179.37(9) . . ?
N6 Fe1 N2 86.23(9) . . ?
N14 Fe1 N2 93.80(9) . . ?
N6 Fe1 N10 94.01(9) . . ?
N14 Fe1 N10 86.61(9) . . ?
N2 Fe1 N10 91.33(9) . . ?
N6 Fe1 N12 92.57(9) . . ?
N14 Fe1 N12 87.42(9) . . ?
N2 Fe1 N12 177.59(9) . . ?
N10 Fe1 N12 86.67(9) . . ?
N6 Fe1 N4 87.47(9) . . ?
N14 Fe1 N4 91.91(9) . . ?
N2 Fe1 N4 86.50(9) . . ?
N10 Fe1 N4 177.29(9) . . ?
N12 Fe1 N4 95.54(9) . . ?
N1 B1 N3 107.8(2) . . ?
N1 B1 N5 108.4(2) . . ?
N3 B1 N5 109.1(2) . . ?
N11 B2 N9 108.1(2) . . ?
N11 B2 N13 109.5(2) . . ?
N9 B2 N13 107.7(2) . . ?
C13 C12 N12 114.9(7) . . ?
C14 C13 C12 104.9(6) . . ?
N11 C14 C13 104.5(7) . . ?
C14B C13B C12B 106.5(5) . . ?
C13B C14B N11 112.4(6) . . ?
N12 C12B C13B 105.2(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11 N7 0.93 2.74 3.644(4) 165.9 4_676 yes
N16 H3C N7 0.97 2.09 3.054(3) 172.5 1_655 yes
N16 H6 N2 0.95 2.67 3.337(4) 127.5 . yes
N8 H4 N10 1.07 2.72 3.391(4) 120.8 . yes
N8 H4 N12 1.07 2.60 3.359(3) 127.3 . yes
N8 H5 N15 0.99 2.12 3.056(3) 158.5 1_455 yes
C2^a H2^a N15 0.93 2.80 3.695(9) 162.2 3_766 yes

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.064



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

data_OH202
_database_code_depnum_ccdc_archive 'CCDC 2370865'
loop_
_audit_author_name
_audit_author_address
'Laure Vendier'
;Laboratoire de Chimie de Coordination CNRS 
France
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_cell_length_a                   9.6251(18)
_cell_length_b                   18.494(3)
_cell_length_c                   13.335(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.540(6)
_cell_angle_gamma                90
_cell_volume                     2372.9(8)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1 '
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Fe 0.3463 0.8444 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805
1.0369 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C24 H18 B0.50 Fe1 N12 
# Dc =      1.50 Fooo =   1098.00 Mu =      6.77 M =    535.74
# Found Formula = C18 H16 B2 Fe1 N16 
# Dc =      1.49 FOOO =   1088.00 Mu =      6.80 M =    533.90

_chemical_formula_sum            'C18 H16 B2 Fe N16'
_chemical_formula_moiety         'C18 H16 B2 Fe N16'
_chemical_compound_source        .
_chemical_formula_weight         533.90


_cell_measurement_reflns_used    7881
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.88
_cell_measurement_temperature    100

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_max          0.150

_exptl_crystal_density_diffrn    1.494

_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.680

# Sheldrick geometric approximatio 0.95 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            34154
_diffrn_reflns_av_unetI/netI     0.084
_reflns_number_total             3978
_diffrn_reflns_av_R_equivalents  0.066
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3978 
# Theoretical number of reflections is about 8059 


_diffrn_reflns_theta_min         2.202
_diffrn_reflns_theta_max         31.736
_diffrn_measured_fraction_theta_max 0.984

_diffrn_reflns_theta_full        30.784
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.45
_refine_diff_density_max         0.48


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3975
_oxford_refine_ls_R_factor_ref   0.0541
_refine_ls_R_factor_all          0.0541
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_all         0.1210
_refine_ls_goodness_of_fit_ref   0.8531
_refine_ls_shift/su_max          0.0004298
_refine_ls_shift/su_mean         0.0000440


# Computed with I/sigma = -10 
_oxford_reflns_number_all        3978
_oxford_refine_ls_R_factor_all   0.0543
_oxford_refine_ls_wR_factor_all  0.1221

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3086
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_gt          0.1021


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 3.73P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Fe1 Fe 0.2500 0.7500 0.5000 0.0245 1.0000 Uani S . . . . .
N6 N 0.28825(16) 0.73728(7) 0.35732(11) 0.0293 1.0000 Uani . . . . . .
N5 N 0.31205(16) 0.79654(8) 0.29964(11) 0.0329 1.0000 Uani . . . . . .
N8 N 0.2569(3) 0.54925(12) 0.3404(2) 0.0755 1.0000 Uani . . . . . .
N1 N 0.41854(16) 0.87108(8) 0.43544(11) 0.0326 1.0000 Uani . . . . . .
N2 N 0.40734(15) 0.81911(8) 0.50722(11) 0.0314 1.0000 Uani . . . . . .
N4 N 0.12427(15) 0.83084(8) 0.46110(11) 0.0305 1.0000 Uani . . . . . .
C8 C 0.3322(2) 0.77354(13) 0.20588(14) 0.0417 1.0000 Uani . . . . . .
N7 N 0.3241(2) 0.70237(11) 0.19816(12) 0.0462 1.0000 Uani . . . . . .
C7 C 0.29718(19) 0.68231(10) 0.29312(14) 0.0356 1.0000 Uani . . . . . .
C9 C 0.2759(3) 0.60830(12) 0.32183(17) 0.0473 1.0000 Uani . . . . . .
B1 B 0.3103(2) 0.87328(11) 0.34948(15) 0.0342 1.0000 Uani . . . . . .
C3 C 0.5311(2) 0.91258(10) 0.45600(16) 0.0409 1.0000 Uani . . . . . .
C2 C 0.5952(2) 0.88722(13) 0.54223(18) 0.0478 1.0000 Uani . . . . . .
C1 C 0.5142(2) 0.82867(11) 0.57138(15) 0.0404 1.0000 Uani . . . . . .
N3 N 0.16692(16) 0.88142(8) 0.39419(12) 0.0340 1.0000 Uani . . . . . .
C6 C 0.0661(2) 0.93058(11) 0.37833(17) 0.0461 1.0000 Uani . . . . . .
C5 C -0.0447(2) 0.91255(13) 0.43538(19) 0.0511 1.0000 Uani . . . . . .
C4 C -0.0041(2) 0.84989(11) 0.48599(15) 0.0399 1.0000 Uani . . . . . .
H81 H 0.3502 0.8054 0.1509 0.0492 1.0000 Uiso . . . . . .
H31 H 0.5613 0.9527 0.4168 0.0483 1.0000 Uiso . . . . . .
H21 H 0.6772 0.9062 0.5749 0.0564 1.0000 Uiso . . . . . .
H11 H 0.5331 0.7982 0.6290 0.0485 1.0000 Uiso . . . . . .
H61 H 0.0720 0.9715 0.3343 0.0547 1.0000 Uiso . . . . . .
H51 H -0.1323 0.9370 0.4391 0.0599 1.0000 Uiso . . . . . .
H41 H -0.0595 0.8239 0.5322 0.0471 1.0000 Uiso . . . . . .
H1 H 0.3369 0.9142 0.2934 0.0500 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.11061(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 . N4 4_566 1.9836(14) yes
Fe1 . N2 4_566 1.9820(15) yes
Fe1 . N6 4_566 1.9618(14) yes
Fe1 . N6 . 1.9618(14) yes
Fe1 . N2 . 1.9820(15) yes
Fe1 . N4 . 1.9836(14) yes
N6 . N5 . 1.3619(19) yes
N6 . C7 . 1.333(2) yes
N5 . C8 . 1.340(2) yes
N5 . B1 . 1.567(3) yes
N8 . C9 . 1.136(3) yes
N1 . N2 . 1.363(2) yes
N1 . B1 . 1.529(3) yes
N1 . C3 . 1.350(2) yes
N2 . C1 . 1.332(2) yes
N4 . N3 . 1.3637(19) yes
N4 . C4 . 1.336(2) yes
C8 . N7 . 1.323(3) yes
C8 . H81 . 0.960 no
N7 . C7 . 1.351(2) yes
C7 . C9 . 1.437(3) yes
B1 . N3 . 1.525(3) yes
B1 . H1 . 1.098 no
C3 . C2 . 1.373(3) yes
C3 . H31 . 0.958 no
C2 . C1 . 1.396(3) yes
C2 . H21 . 0.958 no
C1 . H11 . 0.966 no
N3 . C6 . 1.343(2) yes
C6 . C5 . 1.368(3) yes
C6 . H61 . 0.961 no
C5 . C4 . 1.392(3) yes
C5 . H51 . 0.959 no
C4 . H41 . 0.955 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N4 4_566 Fe1 . N2 4_566 89.24(6) yes
N4 4_566 Fe1 . N6 4_566 88.04(6) yes
N2 4_566 Fe1 . N6 4_566 87.79(6) yes
N4 4_566 Fe1 . N6 . 91.96(6) yes
N2 4_566 Fe1 . N6 . 92.21(6) yes
N6 4_566 Fe1 . N6 . 179.99 yes
N4 4_566 Fe1 . N2 . 90.76(6) yes
N2 4_566 Fe1 . N2 . 179.99 yes
N6 4_566 Fe1 . N2 . 92.21(6) yes
N6 . Fe1 . N2 . 87.79(6) yes
N4 4_566 Fe1 . N4 . 179.99 yes
N2 4_566 Fe1 . N4 . 90.76(6) yes
N6 4_566 Fe1 . N4 . 91.96(6) yes
N6 . Fe1 . N4 . 88.04(6) yes
N2 . Fe1 . N4 . 89.24(6) yes
Fe1 . N6 . N5 . 119.35(11) yes
Fe1 . N6 . C7 . 136.99(12) yes
N5 . N6 . C7 . 103.66(14) yes
N6 . N5 . C8 . 107.60(15) yes
N6 . N5 . B1 . 119.03(13) yes
C8 . N5 . B1 . 133.36(16) yes
N2 . N1 . B1 . 118.70(14) yes
N2 . N1 . C3 . 109.67(16) yes
B1 . N1 . C3 . 131.62(16) yes
N1 . N2 . Fe1 . 119.70(11) yes
N1 . N2 . C1 . 106.46(15) yes
Fe1 . N2 . C1 . 133.84(13) yes
Fe1 . N4 . N3 . 119.73(11) yes
Fe1 . N4 . C4 . 134.10(12) yes
N3 . N4 . C4 . 106.17(14) yes
N5 . C8 . N7 . 112.26(17) yes
N5 . C8 . H81 . 123.5 no
N7 . C8 . H81 . 124.3 no
C8 . N7 . C7 . 102.28(15) yes
N7 . C7 . N6 . 114.19(17) yes
N7 . C7 . C9 . 122.91(18) yes
N6 . C7 . C9 . 122.88(17) yes
C7 . C9 . N8 . 177.0(3) yes
N5 . B1 . N1 . 106.20(15) yes
N5 . B1 . N3 . 105.98(15) yes
N1 . B1 . N3 . 108.36(15) yes
N5 . B1 . H1 . 109.2 no
N1 . B1 . H1 . 111.2 no
N3 . B1 . H1 . 115.3 no
N1 . C3 . C2 . 108.41(17) yes
N1 . C3 . H31 . 125.7 no
C2 . C3 . H31 . 125.9 no
C3 . C2 . C1 . 104.87(18) yes
C3 . C2 . H21 . 127.0 no
C1 . C2 . H21 . 128.1 no
C2 . C1 . N2 . 110.59(18) yes
C2 . C1 . H11 . 125.4 no
N2 . C1 . H11 . 124.0 no
B1 . N3 . N4 . 118.65(14) yes
B1 . N3 . C6 . 131.54(16) yes
N4 . N3 . C6 . 109.79(15) yes
N3 . C6 . C5 . 108.57(17) yes
N3 . C6 . H61 . 125.1 no
C5 . C6 . H61 . 126.3 no
C6 . C5 . C4 . 105.07(18) yes
C6 . C5 . H51 . 127.9 no
C4 . C5 . H51 . 127.1 no
C5 . C4 . N4 . 110.40(17) yes
C5 . C4 . H41 . 125.3 no
N4 . C4 . H41 . 124.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C4 . H41 . N7 8_465 157 0.96 2.55 3.453(3) yes


####################################################################### 
# 
# 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_OH218-100K
_database_code_depnum_ccdc_archive 'CCDC 2370866'
loop_
_audit_author_name
_audit_author_address
'Laure Vendier'
;Laboratoire de Chimie de Coordination CNRS 
France
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 B2 Fe N16, C H2 Cl2'
_chemical_formula_sum            'C19 H18 B2 Cl2 Fe N16'
_chemical_formula_weight         618.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3640 0.7020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1340 3.1970 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.4188(2)
_cell_length_b                   23.3314(7)
_cell_length_c                   15.4739(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.793(2)
_cell_angle_gamma                90
_cell_volume                     2621.86(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11017
_cell_measurement_theta_min      2.9000
_cell_measurement_theta_max      72.9520

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             1256

_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    6.873
_exptl_absorpt_correction_T_min  0.62970
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            21400
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.479
_diffrn_reflns_theta_max         65.084
_diffrn_reflns_theta_full        65.084
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4449
_reflns_number_gt                3996
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 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-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1112P)²+10.7824P] 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_number_reflns         4449
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2142
_refine_ls_wR_factor_gt          0.2095
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9727(7) 0.5200(2) 0.7082(3) 0.0267(11) Uani 1 1 d . . . . .
H1 H 0.928962 0.506449 0.649788 0.032 Uiso 1 1 calc R U . . .
C2 C 1.1027(8) 0.4920(3) 0.7722(4) 0.0337(13) Uani 1 1 d . . . . .
H2 H 1.164074 0.456947 0.765986 0.040 Uiso 1 1 calc R U . . .
C3 C 1.1225(7) 0.5255(3) 0.8452(4) 0.0320(12) Uani 1 1 d . . . . .
H3 H 1.200909 0.517549 0.900498 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4821(7) 0.6233(2) 0.8241(3) 0.0281(12) Uani 1 1 d . . . . .
H4 H 0.369601 0.622226 0.781755 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4951(8) 0.6231(3) 0.9159(3) 0.0320(13) Uani 1 1 d . . . . .
H5 H 0.397622 0.621951 0.947253 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6829(8) 0.6250(2) 0.9503(3) 0.0299(12) Uani 1 1 d . . . . .
H6 H 0.738722 0.625350 1.011297 0.036 Uiso 1 1 calc R U . . .
C7 C 0.9916(7) 0.7349(2) 0.7232(3) 0.0250(11) Uani 1 1 d . . . . .
C8 C 1.1345(7) 0.7230(2) 0.8523(3) 0.0275(11) Uani 1 1 d . . . . .
H8 H 1.215426 0.727741 0.907930 0.033 Uiso 1 1 calc R U . . .
C9 C 0.9237(7) 0.7597(2) 0.6370(3) 0.0270(11) Uani 1 1 d . . . . .
C10 C 1.0035(7) 0.6314(2) 0.5644(3) 0.0249(11) Uani 1 1 d . . . . .
H10 H 1.114661 0.626083 0.606681 0.030 Uiso 1 1 calc R U . . .
C11 C 0.9931(7) 0.6396(2) 0.4743(3) 0.0271(11) Uani 1 1 d . . . . .
H11 H 1.092074 0.640928 0.443905 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8086(7) 0.6455(2) 0.4390(3) 0.0270(11) Uani 1 1 d . . . . .
H12 H 0.755783 0.651855 0.378439 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4825(7) 0.5262(2) 0.6587(3) 0.0267(11) Uani 1 1 d . . . . .
H13 H 0.519402 0.508335 0.714692 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3469(7) 0.5046(2) 0.5898(4) 0.0295(12) Uani 1 1 d . . . . .
H14 H 0.276106 0.470668 0.589488 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3394(7) 0.5439(2) 0.5225(3) 0.0275(11) Uani 1 1 d . . . . .
H15 H 0.260654 0.541523 0.465843 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5132(7) 0.7398(2) 0.6829(3) 0.0245(11) Uani 1 1 d . . . . .
C17 C 0.3746(7) 0.7398(3) 0.5508(3) 0.0301(12) Uani 1 1 d . . . . .
H17 H 0.298679 0.749975 0.495767 0.036 Uiso 1 1 calc R U . . .
C18 C 0.5810(7) 0.7559(2) 0.7728(4) 0.0299(12) Uani 1 1 d . . . . .
C20 C 0.7244(13) 0.9084(3) 0.6392(4) 0.062(2) Uani 1 1 d . . . . .
H20A H 0.591701 0.915444 0.636283 0.074 Uiso 1 1 calc R U . . .
H20B H 0.735704 0.876480 0.598524 0.074 Uiso 1 1 calc R U . . .
B1 B 0.9779(8) 0.6239(3) 0.8825(4) 0.0251(12) Uani 1 1 d . . . . .
H1A H 1.054932 0.622093 0.943514 0.030 Uiso 1 1 calc R U . . .
B2 B 0.5075(8) 0.6405(3) 0.5040(4) 0.0260(12) Uani 1 1 d . . . . .
H2A H 0.431850 0.644006 0.442822 0.031 Uiso 1 1 calc R U . . .
Cl1 Cl 0.8273(3) 0.97172(9) 0.60412(10) 0.0634(6) Uani 1 1 d . . . . .
Cl2 Cl 0.8290(3) 0.88887(8) 0.74680(11) 0.0619(5) Uani 1 1 d . . . . .
Fe1 Fe 0.74096(10) 0.62942(3) 0.69359(4) 0.0202(3) Uani 1 1 d . . . . .
N1 N 1.0127(6) 0.5723(2) 0.8266(3) 0.0266(10) Uani 1 1 d . . . . .
N2 N 0.9184(6) 0.5686(2) 0.7410(3) 0.0274(10) Uani 1 1 d . . . . .
N3 N 0.7726(6) 0.62608(19) 0.8835(3) 0.0252(9) Uani 1 1 d . . . . .
N4 N 0.6484(6) 0.62533(19) 0.8041(3) 0.0235(9) Uani 1 1 d . . . . .
N5 N 1.0210(6) 0.67860(19) 0.8319(3) 0.0242(9) Uani 1 1 d . . . . .
N6 N 0.9274(5) 0.68585(19) 0.7478(2) 0.0230(9) Uani 1 1 d . . . . .
N7 N 1.1220(6) 0.7600(2) 0.7861(3) 0.0282(10) Uani 1 1 d . . . . .
N8 N 0.8655(7) 0.7791(2) 0.5697(3) 0.0329(11) Uani 1 1 d . . . . .
N9 N 0.7153(6) 0.64061(19) 0.5046(3) 0.0232(9) Uani 1 1 d . . . . .
N10 N 0.8348(6) 0.63214(18) 0.5832(3) 0.0236(9) Uani 1 1 d . . . . .
N11 N 0.4619(5) 0.5861(2) 0.5500(3) 0.0252(9) Uani 1 1 d . . . . .
N12 N 0.5530(6) 0.57508(19) 0.6352(3) 0.0250(9) Uani 1 1 d . . . . .
N13 N 0.4739(6) 0.6920(2) 0.5642(3) 0.0252(9) Uani 1 1 d . . . . .
N14 N 0.5671(5) 0.69142(19) 0.6500(2) 0.0223(9) Uani 1 1 d . . . . .
N15 N 0.3939(6) 0.7717(2) 0.6236(3) 0.0320(10) Uani 1 1 d . . . . .
N16 N 0.6427(7) 0.7673(2) 0.8448(3) 0.0375(12) 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
C1 N2 1.338(7) . ?
C1 C2 1.395(8) . ?
C2 C3 1.358(8) . ?
C3 N1 1.357(7) . ?
C4 N4 1.333(7) . ?
C4 C5 1.405(7) . ?
C5 C6 1.386(8) . ?
C6 N3 1.340(7) . ?
C7 N6 1.325(7) . ?
C7 N7 1.357(6) . ?
C7 C9 1.447(7) . ?
C8 N7 1.327(7) . ?
C8 N5 1.332(7) . ?
C9 N8 1.136(7) . ?
C10 N10 1.341(7) . ?
C10 C11 1.394(7) . ?
C11 C12 1.373(8) . ?
C12 N9 1.346(6) . ?
C13 N12 1.337(7) . ?
C13 C14 1.401(7) . ?
C14 C15 1.379(8) . ?
C15 N11 1.349(7) . ?
C16 N14 1.332(7) . ?
C16 N15 1.360(7) . ?
C16 C18 1.430(7) . ?
C17 N13 1.329(7) . ?
C17 N15 1.335(7) . ?
C18 N16 1.144(7) . ?
C20 Cl2 1.748(7) . ?
C20 Cl1 1.797(9) . ?
B1 N3 1.527(7) . ?
B1 N1 1.533(7) . ?
B1 N5 1.564(7) . ?
B2 N11 1.527(8) . ?
B2 N9 1.540(7) . ?
B2 N13 1.570(7) . ?
Fe1 N12 1.963(4) . ?
Fe1 N14 1.964(4) . ?
Fe1 N6 1.969(4) . ?
Fe1 N4 1.971(4) . ?
Fe1 N2 1.972(5) . ?
Fe1 N10 1.973(4) . ?
N1 N2 1.369(6) . ?
N3 N4 1.376(6) . ?
N5 N6 1.355(5) . ?
N9 N10 1.365(6) . ?
N11 N12 1.378(6) . ?
N13 N14 1.366(5) . ?

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 C1 C2 110.3(5) . . ?
C3 C2 C1 105.2(5) . . ?
C2 C3 N1 109.3(5) . . ?
N4 C4 C5 111.0(5) . . ?
C6 C5 C4 104.1(5) . . ?
N3 C6 C5 108.8(5) . . ?
N6 C7 N7 114.4(4) . . ?
N6 C7 C9 122.1(4) . . ?
N7 C7 C9 123.5(5) . . ?
N7 C8 N5 112.5(4) . . ?
N8 C9 C7 178.1(6) . . ?
N10 C10 C11 110.5(5) . . ?
C12 C11 C10 105.0(4) . . ?
N9 C12 C11 108.4(4) . . ?
N12 C13 C14 111.1(5) . . ?
C15 C14 C13 104.4(5) . . ?
N11 C15 C14 109.0(5) . . ?
N14 C16 N15 114.3(4) . . ?
N14 C16 C18 121.4(5) . . ?
N15 C16 C18 124.3(5) . . ?
N13 C17 N15 112.1(4) . . ?
N16 C18 C16 176.7(6) . . ?
Cl2 C20 Cl1 111.7(4) . . ?
N3 B1 N1 108.4(4) . . ?
N3 B1 N5 106.5(4) . . ?
N1 B1 N5 106.5(4) . . ?
N11 B2 N9 108.4(4) . . ?
N11 B2 N13 106.4(4) . . ?
N9 B2 N13 106.0(4) . . ?
N12 Fe1 N14 87.87(18) . . ?
N12 Fe1 N6 177.69(17) . . ?
N14 Fe1 N6 90.50(18) . . ?
N12 Fe1 N4 91.58(17) . . ?
N14 Fe1 N4 90.74(17) . . ?
N6 Fe1 N4 90.08(17) . . ?
N12 Fe1 N2 93.67(19) . . ?
N14 Fe1 N2 178.10(17) . . ?
N6 Fe1 N2 88.00(18) . . ?
N4 Fe1 N2 88.10(17) . . ?
N12 Fe1 N10 88.02(17) . . ?
N14 Fe1 N10 90.13(17) . . ?
N6 Fe1 N10 90.35(17) . . ?
N4 Fe1 N10 179.03(18) . . ?
N2 Fe1 N10 91.04(17) . . ?
C3 N1 N2 108.6(4) . . ?
C3 N1 B1 132.4(4) . . ?
N2 N1 B1 118.9(4) . . ?
C1 N2 N1 106.6(4) . . ?
C1 N2 Fe1 134.3(3) . . ?
N1 N2 Fe1 119.0(3) . . ?
C6 N3 N4 109.9(4) . . ?
C6 N3 B1 131.4(4) . . ?
N4 N3 B1 118.5(4) . . ?
C4 N4 N3 106.0(4) . . ?
C4 N4 Fe1 134.9(4) . . ?
N3 N4 Fe1 119.0(3) . . ?
C8 N5 N6 107.8(4) . . ?
C8 N5 B1 134.5(4) . . ?
N6 N5 B1 117.7(4) . . ?
C7 N6 N5 103.9(4) . . ?
C7 N6 Fe1 135.9(3) . . ?
N5 N6 Fe1 120.2(3) . . ?
C8 N7 C7 101.5(4) . . ?
C12 N9 N10 110.1(4) . . ?
C12 N9 B2 131.6(4) . . ?
N10 N9 B2 118.2(4) . . ?
C10 N10 N9 105.9(4) . . ?
C10 N10 Fe1 134.2(3) . . ?
N9 N10 Fe1 119.7(3) . . ?
C15 N11 N12 109.5(4) . . ?
C15 N11 B2 131.3(4) . . ?
N12 N11 B2 119.3(4) . . ?
C13 N12 N11 106.0(4) . . ?
C13 N12 Fe1 135.0(4) . . ?
N11 N12 Fe1 118.9(3) . . ?
C17 N13 N14 108.3(4) . . ?
C17 N13 B2 134.3(4) . . ?
N14 N13 B2 117.4(4) . . ?
C16 N14 N13 103.4(4) . . ?
C16 N14 Fe1 136.0(3) . . ?
N13 N14 Fe1 120.5(3) . . ?
C17 N15 C16 101.9(4) . . ?

_refine_diff_density_max         0.727
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.108




####################################################################### 
# 
# 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_Olek070721-OH115
_database_code_depnum_ccdc_archive 'CCDC 2370867'
loop_
_audit_author_name
_audit_author_address
'Laure Vendier'
;Laboratoire de Chimie de Coordination CNRS 
France
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 B N8 O2, C16 H36 N'
_chemical_formula_sum            'C24 H44 B N9 O2'
_chemical_formula_weight         501.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.96420(10)
_cell_length_b                   15.72730(10)
_cell_length_c                   15.0760(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.1220(10)
_cell_angle_gamma                90
_cell_volume                     2834.82(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(8)
_cell_measurement_reflns_used    24848
_cell_measurement_theta_min      2.8340
_cell_measurement_theta_max      71.4660

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_min  0.38043
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      173(8)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_measurement_method       ω-φ
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1978
_diffrn_reflns_number            89937
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.063
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_full        66.596
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5001
_reflns_number_gt                4168
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²+0.4035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5001
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.15188(13) -0.02347(9) 0.19644(11) 0.0445(4) Uani 1 1 d . . . . .
H1 H -0.192684 -0.059866 0.156744 0.053 Uiso 1 1 calc R U . . .
C2 C -0.17701(13) -0.01189(11) 0.28439(12) 0.0501(4) Uani 1 1 d . . . . .
H2 H -0.235855 -0.037283 0.315694 0.060 Uiso 1 1 calc R U . . .
C3 C -0.09828(13) 0.04422(11) 0.31612(11) 0.0473(4) Uani 1 1 d . . . . .
H3 H -0.091849 0.065287 0.375152 0.057 Uiso 1 1 calc R U . . .
C4 C 0.22469(16) 0.07368(9) 0.45249(13) 0.0535(5) Uani 1 1 d . . . . .
H4 H 0.231733 0.064917 0.514798 0.064 Uiso 1 1 calc R U . . .
C5 C 0.31120(14) 0.06218(10) 0.39546(14) 0.0550(5) Uani 1 1 d . . . . .
H5 H 0.385773 0.044875 0.409788 0.066 Uiso 1 1 calc R U . . .
C6 C 0.26466(12) 0.08150(9) 0.31342(12) 0.0451(4) Uani 1 1 d . . . . .
H6 H 0.302120 0.080122 0.258966 0.054 Uiso 1 1 calc R U . . .
C7 C 0.00087(13) 0.25643(9) 0.34622(10) 0.0401(3) Uani 1 1 d . . . . .
H7 H 0.002164 0.228047 0.401871 0.048 Uiso 1 1 calc R U . . .
C8 C -0.01699(11) 0.34509(9) 0.24783(10) 0.0361(3) Uani 1 1 d . . . . .
C9 C 0.30359(11) 0.32733(8) 0.34038(9) 0.0316(3) Uani 1 1 d . . . . .
H9A H 0.311186 0.264768 0.336611 0.038 Uiso 1 1 calc R U . . .
H9B H 0.224026 0.341284 0.327142 0.038 Uiso 1 1 calc R U . . .
C10 C 0.37261(11) 0.36669(9) 0.26911(9) 0.0350(3) Uani 1 1 d . . . . .
H10A H 0.453057 0.357408 0.283627 0.042 Uiso 1 1 calc R U . . .
H10B H 0.358961 0.428746 0.266824 0.042 Uiso 1 1 calc R U . . .
C11 C 0.34247(14) 0.32766(11) 0.17941(11) 0.0485(4) Uani 1 1 d . . . . .
H11A H 0.262404 0.338364 0.164600 0.058 Uiso 1 1 calc R U . . .
H11B H 0.353613 0.265349 0.182736 0.058 Uiso 1 1 calc R U . . .
C12 C 0.41242(14) 0.36355(10) 0.10640(11) 0.0479(4) Uani 1 1 d . . . . .
H12A H 0.392937 0.423420 0.096527 0.072 Uiso 1 1 calc R U . . .
H12B H 0.397646 0.331388 0.051536 0.072 Uiso 1 1 calc R U . . .
H12C H 0.491897 0.359054 0.123935 0.072 Uiso 1 1 calc R U . . .
C13 C 0.31531(11) 0.44927(8) 0.44812(9) 0.0318(3) Uani 1 1 d . . . . .
H13A H 0.335390 0.463733 0.510605 0.038 Uiso 1 1 calc R U . . .
H13B H 0.367589 0.480139 0.410206 0.038 Uiso 1 1 calc R U . . .
C14 C 0.19766(12) 0.48112(9) 0.42676(11) 0.0408(3) Uani 1 1 d . . . . .
H14A H 0.143379 0.446075 0.458675 0.049 Uiso 1 1 calc R U . . .
H14B H 0.180607 0.475218 0.362300 0.049 Uiso 1 1 calc R U . . .
C15 C 0.18552(14) 0.57371(10) 0.45362(11) 0.0469(4) Uani 1 1 d . . . . .
H15A H 0.200387 0.578855 0.518432 0.056 Uiso 1 1 calc R U . . .
H15B H 0.242318 0.607978 0.423585 0.056 Uiso 1 1 calc R U . . .
C16 C 0.07076(15) 0.60932(11) 0.43049(14) 0.0581(5) Uani 1 1 d . . . . .
H16A H 0.057711 0.608373 0.365943 0.087 Uiso 1 1 calc R U . . .
H16B H 0.066253 0.667992 0.451949 0.087 Uiso 1 1 calc R U . . .
H16C H 0.013907 0.574671 0.458598 0.087 Uiso 1 1 calc R U . . .
C17 C 0.45486(10) 0.33663(8) 0.46057(9) 0.0309(3) Uani 1 1 d . . . . .
H17A H 0.502178 0.371620 0.422311 0.037 Uiso 1 1 calc R U . . .
H17B H 0.469587 0.355210 0.522649 0.037 Uiso 1 1 calc R U . . .
C18 C 0.49014(11) 0.24445(9) 0.45249(10) 0.0380(3) Uani 1 1 d . . . . .
H18A H 0.473435 0.224561 0.391121 0.046 Uiso 1 1 calc R U . . .
H18B H 0.446320 0.209228 0.493097 0.046 Uiso 1 1 calc R U . . .
C19 C 0.61393(12) 0.23272(10) 0.47477(10) 0.0410(3) Uani 1 1 d . . . . .
H19A H 0.630620 0.251172 0.536632 0.049 Uiso 1 1 calc R U . . .
H19B H 0.658006 0.268620 0.434979 0.049 Uiso 1 1 calc R U . . .
C20 C 0.64761(15) 0.14001(11) 0.46424(13) 0.0558(4) Uani 1 1 d . . . . .
H20A H 0.607046 0.104894 0.506045 0.084 Uiso 1 1 calc R U . . .
H20B H 0.728255 0.134123 0.476465 0.084 Uiso 1 1 calc R U . . .
H20C H 0.629194 0.121336 0.403423 0.084 Uiso 1 1 calc R U . . .
C21 C 0.25578(10) 0.30290(8) 0.49318(9) 0.0316(3) Uani 1 1 d . . . . .
H21A H 0.177603 0.313418 0.472239 0.038 Uiso 1 1 calc R U . . .
H21B H 0.271423 0.241801 0.483844 0.038 Uiso 1 1 calc R U . . .
C22 C 0.26443(12) 0.32060(9) 0.59167(10) 0.0391(3) Uani 1 1 d . . . . .
H22A H 0.238195 0.379041 0.603621 0.047 Uiso 1 1 calc R U . . .
H22B H 0.343349 0.315953 0.613259 0.047 Uiso 1 1 calc R U . . .
C23 C 0.19331(13) 0.25687(10) 0.63972(10) 0.0444(4) Uani 1 1 d . . . . .
H23A H 0.116487 0.257888 0.612976 0.053 Uiso 1 1 calc R U . . .
H23B H 0.224074 0.199176 0.630908 0.053 Uiso 1 1 calc R U . . .
C24 C 0.18787(16) 0.27372(13) 0.73737(12) 0.0602(5) Uani 1 1 d . . . . .
H24A H 0.263629 0.273099 0.764399 0.090 Uiso 1 1 calc R U . . .
H24B H 0.142727 0.229598 0.764775 0.090 Uiso 1 1 calc R U . . .
H24C H 0.153691 0.329475 0.746754 0.090 Uiso 1 1 calc R U . . .
N1 N -0.03124(9) 0.06468(7) 0.24955(8) 0.0336(3) Uani 1 1 d . . . . .
N2 N -0.06371(10) 0.02241(7) 0.17389(8) 0.0372(3) Uani 1 1 d . . . . .
N3 N 0.15634(9) 0.10285(7) 0.32330(8) 0.0366(3) Uani 1 1 d . . . . .
N4 N 0.13033(11) 0.09841(8) 0.41049(9) 0.0448(3) Uani 1 1 d . . . . .
N5 N 0.02651(9) 0.21919(7) 0.27024(8) 0.0321(3) Uani 1 1 d . . . . .
N6 N 0.01411(9) 0.27734(7) 0.20394(8) 0.0356(3) Uani 1 1 d . . . . .
N7 N -0.02670(11) 0.33774(8) 0.33544(9) 0.0448(3) Uani 1 1 d . . . . .
N8 N -0.03657(10) 0.42517(8) 0.20158(10) 0.0467(3) Uani 1 1 d . . . . .
N9 N 0.33264(8) 0.35427(6) 0.43536(7) 0.0287(2) Uani 1 1 d . . . . .
O1 O -0.05958(11) 0.42233(8) 0.12201(9) 0.0587(3) Uani 1 1 d . . . . .
O2 O -0.02901(12) 0.49027(7) 0.24504(10) 0.0703(4) Uani 1 1 d . . . . .
B1 B 0.06876(13) 0.12615(10) 0.25032(11) 0.0331(3) Uani 1 1 d . . . . .
H1B H 0.1076(12) 0.1260(9) 0.1854(10) 0.036(4) Uiso 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
C1 N2 1.3325(19) . ?
C1 C2 1.382(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.364(2) . ?
C2 H2 0.9500 . ?
C3 N1 1.3468(19) . ?
C3 H3 0.9500 . ?
C4 N4 1.332(2) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(2) . ?
C5 H5 0.9500 . ?
C6 N3 1.3524(18) . ?
C6 H6 0.9500 . ?
C7 N7 1.329(2) . ?
C7 N5 1.3324(18) . ?
C7 H7 0.9500 . ?
C8 N6 1.3151(18) . ?
C8 N7 1.335(2) . ?
C8 N8 1.4544(19) . ?
C9 C10 1.5116(19) . ?
C9 N9 1.5211(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.516(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.516(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.5174(19) . ?
C13 N9 1.5216(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5197(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.512(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.5162(18) . ?
C17 N9 1.5227(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5177(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.523(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.510(2) . ?
C21 N9 1.5224(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5163(19) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.500(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 N2 1.3643(16) . ?
N1 B1 1.5380(18) . ?
N3 N4 1.3638(18) . ?
N3 B1 1.535(2) . ?
N5 N6 1.3588(16) . ?
N5 B1 1.5806(18) . ?
N8 O2 1.2172(18) . ?
N8 O1 1.2216(18) . ?
B1 H1B 1.098(15) . ?

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 C1 C2 112.07(13) . . ?
N2 C1 H1 124.0 . . ?
C2 C1 H1 124.0 . . ?
C3 C2 C1 104.46(14) . . ?
C3 C2 H2 127.8 . . ?
C1 C2 H2 127.8 . . ?
N1 C3 C2 108.40(15) . . ?
N1 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
N4 C4 C5 112.56(16) . . ?
N4 C4 H4 123.7 . . ?
C5 C4 H4 123.7 . . ?
C6 C5 C4 104.11(14) . . ?
C6 C5 H5 127.9 . . ?
C4 C5 H5 127.9 . . ?
N3 C6 C5 108.32(16) . . ?
N3 C6 H6 125.8 . . ?
C5 C6 H6 125.8 . . ?
N7 C7 N5 112.44(13) . . ?
N7 C7 H7 123.8 . . ?
N5 C7 H7 123.8 . . ?
N6 C8 N7 117.65(13) . . ?
N6 C8 N8 120.26(14) . . ?
N7 C8 N8 122.06(13) . . ?
C10 C9 N9 116.32(10) . . ?
C10 C9 H9A 108.2 . . ?
N9 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
N9 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 C11 110.49(12) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 112.17(13) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N9 115.28(10) . . ?
C14 C13 H13A 108.5 . . ?
N9 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
N9 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C13 C14 C15 110.91(12) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 112.86(14) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N9 114.94(10) . . ?
C18 C17 H17A 108.5 . . ?
N9 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
N9 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 C19 111.75(11) . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 110.68(13) . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N9 116.38(10) . . ?
C22 C21 H21A 108.2 . . ?
N9 C21 H21A 108.2 . . ?
C22 C21 H21B 108.2 . . ?
N9 C21 H21B 108.2 . . ?
H21A C21 H21B 107.3 . . ?
C21 C22 C23 109.19(12) . . ?
C21 C22 H22A 109.8 . . ?
C23 C22 H22A 109.8 . . ?
C21 C22 H22B 109.8 . . ?
C23 C22 H22B 109.8 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C22 113.44(13) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C3 N1 N2 110.35(12) . . ?
C3 N1 B1 128.99(12) . . ?
N2 N1 B1 120.66(11) . . ?
C1 N2 N1 104.72(12) . . ?
C6 N3 N4 110.31(13) . . ?
C6 N3 B1 127.71(13) . . ?
N4 N3 B1 121.94(11) . . ?
C4 N4 N3 104.70(14) . . ?
C7 N5 N6 108.31(11) . . ?
C7 N5 B1 130.98(12) . . ?
N6 N5 B1 120.68(11) . . ?
C8 N6 N5 101.56(11) . . ?
C7 N7 C8 100.02(12) . . ?
O2 N8 O1 124.68(14) . . ?
O2 N8 C8 117.58(15) . . ?
O1 N8 C8 117.74(13) . . ?
C9 N9 C13 111.41(10) . . ?
C9 N9 C17 111.60(10) . . ?
C13 N9 C17 106.34(9) . . ?
C9 N9 C21 105.63(9) . . ?
C13 N9 C21 111.14(10) . . ?
C17 N9 C21 110.81(10) . . ?
N3 B1 N1 111.43(12) . . ?
N3 B1 N5 107.42(11) . . ?
N1 B1 N5 109.22(11) . . ?
N3 B1 H1B 109.8(8) . . ?
N1 B1 H1B 110.3(8) . . ?
N5 B1 H1B 108.7(8) . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.039



