# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_19087_0ma
_database_code_depnum_ccdc_archive 'CCDC 1951267'
loop_
_audit_author_name
_audit_author_address
'Carta Veronica'
;Indiana University
United States of America
;
_audit_update_record             
;
2019-09-03 deposited with the CCDC.	2020-01-14 downloaded from the CCDC.
;
_audit_creation_date             2019-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
dbeagan@iu.edu
vcarta@iu.edu
caulton@indiana.edu
_chemical_name_common            ?
_chemical_name_systematic        (DIM)Fe(NO)2
_chemical_formula_moiety         'C22 H28 Fe N4 O2'
_chemical_formula_sum            'C22 H28 Fe N4 O2'
_chemical_formula_weight         436.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.5520(15)
_cell_length_b                   14.0826(9)
_cell_length_c                   18.3080(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4525.3(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2638
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.81
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.694
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex 3 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_preparation       synthesized
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1110
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28523
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.061
_diffrn_reflns_theta_max         25.061
_diffrn_reflns_theta_min         2.162
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2493
_reflns_number_total             4007
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+3.3576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C20(H20), C3(H3), C6(H6)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C22(H22A,H22B,H22C), C13(H13A,H13B,
 H13C), C8(H8A,H8B,H8C), C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.71749(3) 0.42600(3) 0.41208(3) 0.01955(14) Uani 1 1 d . . . . .
N3 N 0.65518(14) 0.30414(17) 0.41864(15) 0.0176(6) Uani 1 1 d . . . . .
N4 N 0.75632(14) 0.36632(18) 0.50487(15) 0.0175(6) Uani 1 1 d . . . . .
O2 O 0.65945(16) 0.61165(18) 0.43536(16) 0.0471(8) Uani 1 1 d . . . . .
N2 N 0.67673(16) 0.5296(2) 0.42896(16) 0.0264(7) Uani 1 1 d . . . . .
N1 N 0.77898(17) 0.4223(2) 0.34412(16) 0.0297(7) Uani 1 1 d . . . . .
O1 O 0.82438(16) 0.4279(2) 0.29587(16) 0.0583(9) Uani 1 1 d . . . . .
C14 C 0.80796(18) 0.4128(2) 0.55447(18) 0.0169(7) Uani 1 1 d . . . . .
C10 C 0.67551(18) 0.2443(2) 0.46821(18) 0.0181(8) Uani 1 1 d . . . . .
C21 C 0.77737(19) 0.4641(2) 0.61220(18) 0.0197(8) Uani 1 1 d . . . . .
C2 C 0.52329(19) 0.3133(2) 0.3767(2) 0.0237(8) Uani 1 1 d . . . . .
C9 C 0.59724(18) 0.2776(2) 0.36645(19) 0.0186(8) Uani 1 1 d . . . . .
C12 C 0.73351(18) 0.2814(2) 0.51979(19) 0.0195(8) Uani 1 1 d . . . . .
C4 C 0.4835(2) 0.2261(2) 0.2682(2) 0.0287(9) Uani 1 1 d . . . . .
C15 C 0.88623(19) 0.4071(2) 0.54249(19) 0.0208(8) Uani 1 1 d . . . . .
C7 C 0.61578(19) 0.2192(2) 0.3075(2) 0.0238(9) Uani 1 1 d . . . . .
C18 C 0.9052(2) 0.5020(2) 0.6516(2) 0.0264(9) Uani 1 1 d . . . . .
C17 C 0.93361(19) 0.4527(2) 0.5922(2) 0.0261(9) Uani 1 1 d . . . . .
H17 H 0.987190 0.449881 0.585175 0.031 Uiso 1 1 calc R . . . .
C20 C 0.8269(2) 0.5073(2) 0.6608(2) 0.0254(9) Uani 1 1 d . . . . .
H20 H 0.806839 0.541333 0.701263 0.030 Uiso 1 1 calc R . . . .
C3 C 0.46797(19) 0.2857(2) 0.3265(2) 0.0293(9) Uani 1 1 d . . . . .
H3 H 0.417480 0.308711 0.332449 0.035 Uiso 1 1 calc R . . . .
C11 C 0.64419(19) 0.1465(2) 0.4787(2) 0.0280(9) Uani 1 1 d . . . . .
H11A H 0.602769 0.135537 0.443798 0.042 Uiso 1 1 calc GR . . . .
H11B H 0.624637 0.140022 0.528589 0.042 Uiso 1 1 calc GR . . . .
H11C H 0.684661 0.099686 0.470566 0.042 Uiso 1 1 calc GR . . . .
C16 C 0.9181(2) 0.3525(2) 0.4787(2) 0.0318(10) Uani 1 1 d . . . . .
H16A H 0.903400 0.285616 0.482782 0.048 Uiso 1 1 calc GR . . . .
H16B H 0.973771 0.357668 0.478594 0.048 Uiso 1 1 calc GR . . . .
H16C H 0.897818 0.378814 0.433054 0.048 Uiso 1 1 calc GR . . . .
C22 C 0.69179(19) 0.4707(2) 0.6222(2) 0.0272(9) Uani 1 1 d . . . . .
H22A H 0.668984 0.500502 0.579068 0.041 Uiso 1 1 calc GR . . . .
H22B H 0.680411 0.509011 0.665543 0.041 Uiso 1 1 calc GR . . . .
H22C H 0.670645 0.406802 0.628501 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.7586(2) 0.2238(2) 0.5847(2) 0.0317(9) Uani 1 1 d . . . . .
H13A H 0.783134 0.165284 0.567836 0.048 Uiso 1 1 calc GR . . . .
H13B H 0.714145 0.207841 0.614684 0.048 Uiso 1 1 calc GR . . . .
H13C H 0.794812 0.260798 0.613854 0.048 Uiso 1 1 calc GR . . . .
C6 C 0.5578(2) 0.1944(2) 0.2597(2) 0.0295(9) Uani 1 1 d . . . . .
H6 H 0.569380 0.154112 0.219557 0.035 Uiso 1 1 calc R . . . .
C8 C 0.69716(19) 0.1854(3) 0.2959(2) 0.0366(10) Uani 1 1 d . . . . .
H8A H 0.731704 0.240072 0.296578 0.055 Uiso 1 1 calc GR . . . .
H8B H 0.700989 0.153054 0.248689 0.055 Uiso 1 1 calc GR . . . .
H8C H 0.711242 0.141285 0.335074 0.055 Uiso 1 1 calc GR . . . .
C1 C 0.5050(2) 0.3783(3) 0.4392(2) 0.0391(10) Uani 1 1 d . . . . .
H1A H 0.519560 0.347796 0.485249 0.059 Uiso 1 1 calc GR . . . .
H1B H 0.450230 0.391702 0.439617 0.059 Uiso 1 1 calc GR . . . .
H1C H 0.533321 0.437822 0.433564 0.059 Uiso 1 1 calc GR . . . .
C19 C 0.9586(2) 0.5492(3) 0.7058(2) 0.0435(11) Uani 1 1 d . . . . .
H19A H 0.998215 0.503992 0.720455 0.065 Uiso 1 1 calc GR . . . .
H19B H 0.929690 0.569176 0.748932 0.065 Uiso 1 1 calc GR . . . .
H19C H 0.982308 0.604734 0.682993 0.065 Uiso 1 1 calc GR . . . .
C5 C 0.4219(2) 0.1984(3) 0.2151(2) 0.0477(12) Uani 1 1 d . . . . .
H5A H 0.382250 0.162478 0.240763 0.072 Uiso 1 1 calc GR . . . .
H5B H 0.443792 0.158888 0.176326 0.072 Uiso 1 1 calc GR . . . .
H5C H 0.399530 0.255676 0.193571 0.072 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N3 2.038(2) . ?
Fe1 N4 2.014(3) . ?
Fe1 N2 1.654(3) . ?
Fe1 N1 1.648(3) . ?
N3 C10 1.289(4) . ?
N3 C9 1.445(4) . ?
N4 C14 1.441(4) . ?
N4 C12 1.290(4) . ?
O2 N2 1.201(3) . ?
N1 O1 1.192(3) . ?
C14 C21 1.388(4) . ?
C14 C15 1.393(4) . ?
C10 C12 1.484(4) . ?
C10 C11 1.496(4) . ?
C21 C20 1.385(4) . ?
C21 C22 1.516(5) . ?
C2 C9 1.404(4) . ?
C2 C3 1.392(5) . ?
C2 C1 1.501(5) . ?
C9 C7 1.395(5) . ?
C12 C13 1.505(4) . ?
C4 C3 1.384(5) . ?
C4 C6 1.387(5) . ?
C4 C5 1.506(5) . ?
C15 C17 1.390(5) . ?
C15 C16 1.507(5) . ?
C7 C6 1.388(5) . ?
C7 C8 1.521(5) . ?
C18 C17 1.384(5) . ?
C18 C20 1.387(5) . ?
C18 C19 1.516(5) . ?
C17 H17 0.9500 . ?
C20 H20 0.9500 . ?
C3 H3 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Fe1 N3 77.32(11) . . ?
N2 Fe1 N3 119.97(12) . . ?
N2 Fe1 N4 110.91(12) . . ?
N1 Fe1 N3 111.68(13) . . ?
N1 Fe1 N4 113.71(12) . . ?
N1 Fe1 N2 116.87(14) . . ?
C10 N3 Fe1 116.3(2) . . ?
C10 N3 C9 119.4(3) . . ?
C9 N3 Fe1 123.8(2) . . ?
C14 N4 Fe1 123.70(19) . . ?
C12 N4 Fe1 117.4(2) . . ?
C12 N4 C14 118.9(3) . . ?
O2 N2 Fe1 167.6(3) . . ?
O1 N1 Fe1 174.3(3) . . ?
C21 C14 N4 118.2(3) . . ?
C21 C14 C15 122.1(3) . . ?
C15 C14 N4 119.7(3) . . ?
N3 C10 C12 114.1(3) . . ?
N3 C10 C11 126.2(3) . . ?
C12 C10 C11 119.7(3) . . ?
C14 C21 C22 120.5(3) . . ?
C20 C21 C14 118.3(3) . . ?
C20 C21 C22 121.2(3) . . ?
C9 C2 C1 121.1(3) . . ?
C3 C2 C9 117.2(3) . . ?
C3 C2 C1 121.6(3) . . ?
C2 C9 N3 118.1(3) . . ?
C7 C9 N3 120.0(3) . . ?
C7 C9 C2 122.0(3) . . ?
N4 C12 C10 113.9(3) . . ?
N4 C12 C13 125.2(3) . . ?
C10 C12 C13 120.9(3) . . ?
C3 C4 C6 117.8(3) . . ?
C3 C4 C5 120.9(3) . . ?
C6 C4 C5 121.2(4) . . ?
C14 C15 C16 121.1(3) . . ?
C17 C15 C14 117.4(3) . . ?
C17 C15 C16 121.4(3) . . ?
C9 C7 C8 120.8(3) . . ?
C6 C7 C9 117.7(3) . . ?
C6 C7 C8 121.5(3) . . ?
C17 C18 C20 118.6(3) . . ?
C17 C18 C19 120.8(3) . . ?
C20 C18 C19 120.6(3) . . ?
C15 C17 H17 118.9 . . ?
C18 C17 C15 122.1(3) . . ?
C18 C17 H17 118.9 . . ?
C21 C20 C18 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C18 C20 H20 119.3 . . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.7(3) . . ?
C4 C3 H3 118.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C6 C7 122.5(4) . . ?
C4 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 N3 C10 C12 9.1(4) . . . . ?
Fe1 N3 C10 C11 -173.3(3) . . . . ?
Fe1 N3 C9 C2 -85.4(3) . . . . ?
Fe1 N3 C9 C7 93.8(3) . . . . ?
Fe1 N4 C14 C21 92.5(3) . . . . ?
Fe1 N4 C14 C15 -86.0(3) . . . . ?
Fe1 N4 C12 C10 -5.4(4) . . . . ?
Fe1 N4 C12 C13 177.4(3) . . . . ?
N3 Fe1 N2 O2 -166.6(12) . . . . ?
N3 C10 C12 N4 -2.5(4) . . . . ?
N3 C10 C12 C13 174.8(3) . . . . ?
N3 C9 C7 C6 178.8(3) . . . . ?
N3 C9 C7 C8 -2.0(5) . . . . ?
N4 Fe1 N2 O2 106.3(13) . . . . ?
N4 C14 C21 C20 178.7(3) . . . . ?
N4 C14 C21 C22 -0.1(4) . . . . ?
N4 C14 C15 C17 -179.6(3) . . . . ?
N4 C14 C15 C16 -0.4(5) . . . . ?
N1 Fe1 N2 O2 -26.3(13) . . . . ?
C14 N4 C12 C10 175.0(3) . . . . ?
C14 N4 C12 C13 -2.2(5) . . . . ?
C14 C21 C20 C18 1.6(5) . . . . ?
C14 C15 C17 C18 0.1(5) . . . . ?
C10 N3 C9 C2 102.4(4) . . . . ?
C10 N3 C9 C7 -78.5(4) . . . . ?
C21 C14 C15 C17 2.0(5) . . . . ?
C21 C14 C15 C16 -178.9(3) . . . . ?
C2 C9 C7 C6 -2.0(5) . . . . ?
C2 C9 C7 C8 177.1(3) . . . . ?
C9 N3 C10 C12 -178.1(3) . . . . ?
C9 N3 C10 C11 -0.5(5) . . . . ?
C9 C2 C3 C4 -0.3(5) . . . . ?
C9 C7 C6 C4 0.6(5) . . . . ?
C12 N4 C14 C21 -87.9(4) . . . . ?
C12 N4 C14 C15 93.5(4) . . . . ?
C15 C14 C21 C20 -2.8(5) . . . . ?
C15 C14 C21 C22 178.4(3) . . . . ?
C17 C18 C20 C21 0.4(5) . . . . ?
C20 C18 C17 C15 -1.2(5) . . . . ?
C3 C2 C9 N3 -179.0(3) . . . . ?
C3 C2 C9 C7 1.9(5) . . . . ?
C3 C4 C6 C7 0.8(5) . . . . ?
C11 C10 C12 N4 179.7(3) . . . . ?
C11 C10 C12 C13 -3.0(5) . . . . ?
C16 C15 C17 C18 -179.1(3) . . . . ?
C22 C21 C20 C18 -179.6(3) . . . . ?
C6 C4 C3 C2 -1.0(5) . . . . ?
C8 C7 C6 C4 -178.5(3) . . . . ?
C1 C2 C9 N3 0.9(5) . . . . ?
C1 C2 C9 C7 -178.2(3) . . . . ?
C1 C2 C3 C4 179.8(3) . . . . ?
C19 C18 C17 C15 178.7(3) . . . . ?
C19 C18 C20 C21 -179.5(3) . . . . ?
C5 C4 C3 C2 -179.8(3) . . . . ?
C5 C4 C6 C7 179.6(3) . . . . ?

_olex2_date_sample_data_collection 2019-06-29
_olex2_date_sample_submission    2019-06-26
_olex2_submission_original_sample_id dmb_22
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Solvent Diffusion'
####################################################################### 
# 
# 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_19088_0ma
_database_code_depnum_ccdc_archive 'CCDC 1951269'
loop_
_audit_author_name
_audit_author_address
'Carta Veronica'
;Indiana University
United States of America
;
_audit_update_record             
;
2019-09-03 deposited with the CCDC.	2020-01-14 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
dbeagan@iu.edu
vcarta@iu.edu
caulton@indiana.edu
_chemical_name_common            ?
_chemical_name_systematic        (DIM)Fe(NO3)2(MeCN)
_chemical_formula_moiety         'C24 H31 Fe N5 O6, 2(C2 H3 N)'
_chemical_formula_sum            'C28 H37 Fe N7 O6'
_chemical_formula_weight         623.49
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

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

_cell_length_a                   17.0228(4)
_cell_length_b                   11.6142(4)
_cell_length_c                   15.9579(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3154.98(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex3 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_preparation       synthesized
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38729
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.078
_diffrn_reflns_theta_max         25.078
_diffrn_reflns_theta_min         2.123
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5084
_reflns_number_total             5587
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     349
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0664
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 Fe1, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Fe1, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Fe1, O5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O1 \\sim Fe1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O4 \\sim Fe1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C20(H20), C17(H17), C3(H3)
5.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C22(H22A,H22B,
 H22C), C13(H13A,H13B,H13C), C24(H24A,H24B,H24C), C1(H1A,H1B,H1C), C26(H26A,
 H26B,H26C), C19(H19A,H19B,H19C), C5(H5A,H5B,H5C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.65715(2) 0.51729(3) 0.41037(3) 0.02072(11) Uani 1 1 d . U . . .
O2 O 0.67218(11) 0.3549(2) 0.34386(15) 0.0334(5) Uani 1 1 d . U . . .
O1 O 0.56033(13) 0.43478(19) 0.32741(15) 0.0372(6) Uani 1 1 d . U . . .
O4 O 0.75265(13) 0.63031(19) 0.47945(16) 0.0406(6) Uani 1 1 d . U . . .
O5 O 0.77480(12) 0.4571(2) 0.44254(16) 0.0396(6) Uani 1 1 d . U . . .
O3 O 0.58698(15) 0.2779(2) 0.25866(17) 0.0490(7) Uani 1 1 d . U . . .
O6 O 0.86834(12) 0.5568(2) 0.50096(16) 0.0423(6) Uani 1 1 d . U . . .
N1 N 0.56759(13) 0.64391(19) 0.44605(15) 0.0190(5) Uani 1 1 d . U . . .
N2 N 0.60593(12) 0.4528(2) 0.52519(15) 0.0197(5) Uani 1 1 d . U . . .
N4 N 0.60561(15) 0.3533(2) 0.30792(17) 0.0305(6) Uani 1 1 d . U . . .
N3 N 0.68038(15) 0.6187(2) 0.29905(18) 0.0317(6) Uani 1 1 d . U . . .
N5 N 0.80088(15) 0.5484(2) 0.47535(17) 0.0310(6) Uani 1 1 d . U . . .
C7 C 0.48628(15) 0.7344(2) 0.33719(19) 0.0210(6) Uani 1 1 d . U . . .
C10 C 0.52975(14) 0.6232(2) 0.51342(18) 0.0192(6) Uani 1 1 d . U . . .
C8 C 0.43147(16) 0.6322(3) 0.3361(2) 0.0258(7) Uani 1 1 d . U . . .
H8A H 0.404331 0.626568 0.390095 0.039 Uiso 1 1 calc GR . . . .
H8B H 0.461756 0.561697 0.326256 0.039 Uiso 1 1 calc GR . . . .
H8C H 0.392745 0.641922 0.291205 0.039 Uiso 1 1 calc GR . . . .
C12 C 0.55147(16) 0.5137(2) 0.55897(18) 0.0193(6) Uani 1 1 d . U . . .
C6 C 0.47593(16) 0.8240(3) 0.28006(19) 0.0257(7) Uani 1 1 d . U . . .
H6 H 0.435135 0.817965 0.239683 0.031 Uiso 1 1 calc R . . . .
C14 C 0.63232(16) 0.3466(2) 0.56402(18) 0.0207(6) Uani 1 1 d . U . . .
C21 C 0.69467(16) 0.3490(2) 0.62058(19) 0.0237(6) Uani 1 1 d . U . . .
C15 C 0.59728(16) 0.2425(3) 0.54129(19) 0.0230(7) Uani 1 1 d . U . . .
C23 C 0.67447(16) 0.6743(3) 0.2410(2) 0.0280(7) Uani 1 1 d . U . . .
C9 C 0.54787(14) 0.7433(2) 0.39504(18) 0.0201(6) Uani 1 1 d . U . . .
C20 C 0.72299(17) 0.2456(3) 0.6516(2) 0.0294(7) Uani 1 1 d . U . . .
H20 H 0.765679 0.246926 0.689935 0.035 Uiso 1 1 calc R . . . .
C2 C 0.59508(15) 0.8421(2) 0.3989(2) 0.0256(7) Uani 1 1 d . U . . .
C11 C 0.46687(16) 0.6980(3) 0.5499(2) 0.0292(7) Uani 1 1 d . U . . .
H11A H 0.464188 0.770449 0.518553 0.044 Uiso 1 1 calc GR . . . .
H11B H 0.479059 0.714286 0.608745 0.044 Uiso 1 1 calc GR . . . .
H11C H 0.416192 0.658275 0.546312 0.044 Uiso 1 1 calc GR . . . .
N7 N 0.6307(2) 0.7280(3) 0.6738(3) 0.0531(9) Uani 1 1 d . U . . .
C16 C 0.52669(16) 0.2369(3) 0.4833(2) 0.0313(7) Uani 1 1 d . U . . .
H16A H 0.501934 0.312983 0.480127 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.488770 0.180906 0.505018 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.543796 0.213314 0.427203 0.047 Uiso 1 1 calc GR . . . .
C18 C 0.69150(18) 0.1411(3) 0.6289(2) 0.0293(7) Uani 1 1 d . U . . .
C22 C 0.73045(17) 0.4600(3) 0.6517(2) 0.0326(8) Uani 1 1 d . U . . .
H22A H 0.712254 0.524063 0.616702 0.049 Uiso 1 1 calc GR . . . .
H22B H 0.787841 0.454860 0.648623 0.049 Uiso 1 1 calc GR . . . .
H22C H 0.714479 0.473253 0.709890 0.049 Uiso 1 1 calc GR . . . .
C13 C 0.50826(18) 0.4833(3) 0.63699(19) 0.0279(7) Uani 1 1 d . U . . .
H13A H 0.523493 0.405827 0.655090 0.042 Uiso 1 1 calc GR . . . .
H13B H 0.451606 0.485227 0.626154 0.042 Uiso 1 1 calc GR . . . .
H13C H 0.521222 0.538863 0.681094 0.042 Uiso 1 1 calc GR . . . .
C4 C 0.52296(18) 0.9217(3) 0.2799(2) 0.0303(7) Uani 1 1 d . U . . .
C17 C 0.62774(17) 0.1417(3) 0.5743(2) 0.0264(7) Uani 1 1 d . U . . .
H17 H 0.604279 0.070404 0.559186 0.032 Uiso 1 1 calc R . . . .
C3 C 0.58089(17) 0.9292(3) 0.3410(2) 0.0291(7) Uani 1 1 d . U . . .
H3 H 0.612219 0.996775 0.343364 0.035 Uiso 1 1 calc R . . . .
C24 C 0.6663(2) 0.7455(3) 0.1662(2) 0.0372(8) Uani 1 1 d . U . . .
H24A H 0.665868 0.696224 0.116396 0.056 Uiso 1 1 calc GR . . . .
H24B H 0.710555 0.799277 0.162865 0.056 Uiso 1 1 calc GR . . . .
H24C H 0.617003 0.788876 0.169243 0.056 Uiso 1 1 calc GR . . . .
C1 C 0.65889(18) 0.8543(3) 0.4626(2) 0.0371(8) Uani 1 1 d . U . . .
H1A H 0.639620 0.828194 0.517298 0.056 Uiso 1 1 calc GR . . . .
H1B H 0.674777 0.935190 0.466441 0.056 Uiso 1 1 calc GR . . . .
H1C H 0.704105 0.807349 0.445918 0.056 Uiso 1 1 calc GR . . . .
C27 C 0.62540(19) 0.7383(3) 0.7431(3) 0.0398(8) Uani 1 1 d . U . . .
C26 C 0.7867(2) 0.1592(3) 0.4184(3) 0.0590(11) Uani 1 1 d . U . . .
H26A H 0.802393 0.171460 0.359960 0.088 Uiso 1 1 calc GR . . . .
H26B H 0.794410 0.230408 0.450204 0.088 Uiso 1 1 calc GR . . . .
H26C H 0.731146 0.137068 0.420410 0.088 Uiso 1 1 calc GR . . . .
C19 C 0.7243(2) 0.0298(3) 0.6636(3) 0.0467(10) Uani 1 1 d . U . . .
H19A H 0.780997 0.037811 0.672231 0.070 Uiso 1 1 calc GR . . . .
H19B H 0.714223 -0.032903 0.623912 0.070 Uiso 1 1 calc GR . . . .
H19C H 0.698784 0.012328 0.717197 0.070 Uiso 1 1 calc GR . . . .
C5 C 0.5124(3) 1.0135(3) 0.2148(3) 0.0468(10) Uani 1 1 d . U . . .
H5A H 0.533643 0.986574 0.161224 0.070 Uiso 1 1 calc GR . . . .
H5B H 0.540372 1.083321 0.232270 0.070 Uiso 1 1 calc GR . . . .
H5C H 0.456386 1.030759 0.208457 0.070 Uiso 1 1 calc GR . . . .
C25 C 0.8339(2) 0.0687(4) 0.4544(4) 0.0657(13) Uani 1 1 d . U . . .
C28 C 0.6187(3) 0.7519(6) 0.8327(3) 0.0907(19) Uani 1 1 d . U . . .
H28A H 0.592125 0.824693 0.845232 0.136 Uiso 1 1 calc GR . . . .
H28B H 0.671304 0.752413 0.857716 0.136 Uiso 1 1 calc GR . . . .
H28C H 0.588288 0.687796 0.855879 0.136 Uiso 1 1 calc GR . . . .
N6 N 0.8694(3) -0.0034(4) 0.4832(5) 0.114(2) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O2 2.179(2) . ?
Fe1 O1 2.321(2) . ?
Fe1 O4 2.362(2) . ?
Fe1 O5 2.183(2) . ?
Fe1 N1 2.193(2) . ?
Fe1 N2 2.163(2) . ?
Fe1 N3 2.168(3) . ?
O2 N4 1.270(3) . ?
O1 N4 1.260(3) . ?
O4 N5 1.258(3) . ?
O5 N5 1.264(3) . ?
O3 N4 1.219(3) . ?
O6 N5 1.223(3) . ?
N1 C10 1.276(3) . ?
N1 C9 1.452(4) . ?
N2 C12 1.284(4) . ?
N2 C14 1.452(4) . ?
N3 C23 1.135(4) . ?
C7 C8 1.510(4) . ?
C7 C6 1.395(4) . ?
C7 C9 1.401(4) . ?
C10 C12 1.511(4) . ?
C10 C11 1.497(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C12 C13 1.488(4) . ?
C6 H6 0.9500 . ?
C6 C4 1.389(4) . ?
C14 C21 1.393(4) . ?
C14 C15 1.396(4) . ?
C21 C20 1.385(4) . ?
C21 C22 1.510(4) . ?
C15 C16 1.518(4) . ?
C15 C17 1.385(4) . ?
C23 C24 1.458(5) . ?
C9 C2 1.403(4) . ?
C20 H20 0.9500 . ?
C20 C18 1.376(4) . ?
C2 C3 1.391(4) . ?
C2 C1 1.494(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N7 C27 1.115(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C17 1.391(4) . ?
C18 C19 1.513(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C4 C3 1.390(5) . ?
C4 C5 1.499(5) . ?
C17 H17 0.9500 . ?
C3 H3 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C27 C28 1.442(6) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C26 C25 1.442(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C25 N6 1.131(6) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Fe1 O1 56.51(7) . . ?
O2 Fe1 O4 128.85(8) . . ?
O2 Fe1 O5 74.30(8) . . ?
O2 Fe1 N1 142.02(8) . . ?
O1 Fe1 O4 169.80(8) . . ?
O5 Fe1 O1 130.80(8) . . ?
O5 Fe1 O4 55.73(8) . . ?
O5 Fe1 N1 142.34(9) . . ?
N1 Fe1 O1 86.06(8) . . ?
N1 Fe1 O4 89.12(8) . . ?
N2 Fe1 O2 99.23(9) . . ?
N2 Fe1 O1 93.10(9) . . ?
N2 Fe1 O4 94.27(9) . . ?
N2 Fe1 O5 93.42(9) . . ?
N2 Fe1 N1 74.46(9) . . ?
N2 Fe1 N3 162.92(9) . . ?
N3 Fe1 O2 92.83(10) . . ?
N3 Fe1 O1 83.48(9) . . ?
N3 Fe1 O4 87.42(9) . . ?
N3 Fe1 O5 101.50(10) . . ?
N3 Fe1 N1 88.59(9) . . ?
N4 O2 Fe1 97.37(17) . . ?
N4 O1 Fe1 90.95(17) . . ?
N5 O4 Fe1 90.28(17) . . ?
N5 O5 Fe1 98.65(17) . . ?
C10 N1 Fe1 116.28(18) . . ?
C10 N1 C9 120.4(2) . . ?
C9 N1 Fe1 123.24(17) . . ?
C12 N2 Fe1 117.1(2) . . ?
C12 N2 C14 120.8(2) . . ?
C14 N2 Fe1 122.07(17) . . ?
O1 N4 O2 115.0(3) . . ?
O3 N4 O2 122.3(3) . . ?
O3 N4 O1 122.7(3) . . ?
C23 N3 Fe1 164.3(2) . . ?
O4 N5 O5 115.3(3) . . ?
O6 N5 O4 122.4(3) . . ?
O6 N5 O5 122.3(3) . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 C9 118.0(3) . . ?
C9 C7 C8 121.9(3) . . ?
N1 C10 C12 116.2(2) . . ?
N1 C10 C11 125.4(3) . . ?
C11 C10 C12 118.5(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C12 C10 116.0(3) . . ?
N2 C12 C13 125.3(3) . . ?
C13 C12 C10 118.8(2) . . ?
C7 C6 H6 118.7 . . ?
C4 C6 C7 122.6(3) . . ?
C4 C6 H6 118.7 . . ?
C21 C14 N2 119.7(2) . . ?
C21 C14 C15 120.7(3) . . ?
C15 C14 N2 119.5(2) . . ?
C14 C21 C22 122.5(3) . . ?
C20 C21 C14 118.6(3) . . ?
C20 C21 C22 118.8(3) . . ?
C14 C15 C16 122.2(3) . . ?
C17 C15 C14 118.3(3) . . ?
C17 C15 C16 119.5(3) . . ?
N3 C23 C24 179.6(4) . . ?
C7 C9 N1 118.9(2) . . ?
C7 C9 C2 121.2(3) . . ?
C2 C9 N1 119.6(2) . . ?
C21 C20 H20 118.8 . . ?
C18 C20 C21 122.3(3) . . ?
C18 C20 H20 118.8 . . ?
C9 C2 C1 121.6(3) . . ?
C3 C2 C9 117.8(3) . . ?
C3 C2 C1 120.6(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C18 C17 117.7(3) . . ?
C20 C18 C19 120.9(3) . . ?
C17 C18 C19 121.4(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C4 C3 117.3(3) . . ?
C6 C4 C5 120.9(3) . . ?
C3 C4 C5 121.8(3) . . ?
C15 C17 C18 122.3(3) . . ?
C15 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C2 C3 H3 118.5 . . ?
C4 C3 C2 123.0(3) . . ?
C4 C3 H3 118.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N7 C27 C28 179.8(5) . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N6 C25 C26 178.5(5) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11B O3 0.98 2.64 3.466(4) 141.6 2_665 yes
C13 H13B O6 0.98 2.50 3.256(4) 134.0 3_465 yes
C24 H24A O6 0.98 2.52 3.480(5) 165.9 4_654 yes
C26 H26B O5 0.98 2.66 3.487(4) 142.8 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O2 N4 O1 -3.8(3) . . . . ?
Fe1 O2 N4 O3 176.6(3) . . . . ?
Fe1 O1 N4 O2 3.5(3) . . . . ?
Fe1 O1 N4 O3 -176.9(3) . . . . ?
Fe1 O4 N5 O5 -2.1(3) . . . . ?
Fe1 O4 N5 O6 177.6(3) . . . . ?
Fe1 O5 N5 O4 2.3(3) . . . . ?
Fe1 O5 N5 O6 -177.4(3) . . . . ?
Fe1 N1 C10 C12 -0.5(3) . . . . ?
Fe1 N1 C10 C11 179.4(2) . . . . ?
Fe1 N1 C9 C7 92.7(3) . . . . ?
Fe1 N1 C9 C2 -81.4(3) . . . . ?
Fe1 N2 C12 C10 0.3(3) . . . . ?
Fe1 N2 C12 C13 179.0(2) . . . . ?
Fe1 N2 C14 C21 87.8(3) . . . . ?
Fe1 N2 C14 C15 -89.2(3) . . . . ?
N1 C10 C12 N2 0.1(4) . . . . ?
N1 C10 C12 C13 -178.7(2) . . . . ?
N1 C9 C2 C3 171.3(3) . . . . ?
N1 C9 C2 C1 -8.5(4) . . . . ?
N2 C14 C21 C20 -174.8(3) . . . . ?
N2 C14 C21 C22 7.5(4) . . . . ?
N2 C14 C15 C16 -6.1(4) . . . . ?
N2 C14 C15 C17 175.0(3) . . . . ?
C7 C6 C4 C3 -1.5(4) . . . . ?
C7 C6 C4 C5 177.0(3) . . . . ?
C7 C9 C2 C3 -2.7(4) . . . . ?
C7 C9 C2 C1 177.6(3) . . . . ?
C10 N1 C9 C7 -83.8(3) . . . . ?
C10 N1 C9 C2 102.1(3) . . . . ?
C8 C7 C6 C4 177.9(3) . . . . ?
C8 C7 C9 N1 10.2(4) . . . . ?
C8 C7 C9 C2 -175.8(3) . . . . ?
C12 N2 C14 C21 -91.0(3) . . . . ?
C12 N2 C14 C15 91.9(3) . . . . ?
C6 C7 C9 N1 -170.4(2) . . . . ?
C6 C7 C9 C2 3.6(4) . . . . ?
C6 C4 C3 C2 2.5(5) . . . . ?
C14 N2 C12 C10 179.2(2) . . . . ?
C14 N2 C12 C13 -2.1(4) . . . . ?
C14 C21 C20 C18 -0.3(5) . . . . ?
C14 C15 C17 C18 0.0(5) . . . . ?
C21 C14 C15 C16 176.9(3) . . . . ?
C21 C14 C15 C17 -2.1(4) . . . . ?
C21 C20 C18 C17 -1.6(5) . . . . ?
C21 C20 C18 C19 179.6(3) . . . . ?
C15 C14 C21 C20 2.2(4) . . . . ?
C15 C14 C21 C22 -175.5(3) . . . . ?
C9 N1 C10 C12 176.3(2) . . . . ?
C9 N1 C10 C11 -3.8(4) . . . . ?
C9 C7 C6 C4 -1.5(4) . . . . ?
C9 C2 C3 C4 -0.5(5) . . . . ?
C20 C18 C17 C15 1.8(5) . . . . ?
C11 C10 C12 N2 -179.8(3) . . . . ?
C11 C10 C12 C13 1.4(4) . . . . ?
C16 C15 C17 C18 -179.0(3) . . . . ?
C22 C21 C20 C18 177.4(3) . . . . ?
C1 C2 C3 C4 179.3(3) . . . . ?
C19 C18 C17 C15 -179.5(3) . . . . ?
C5 C4 C3 C2 -175.9(3) . . . . ?

_olex2_date_sample_data_collection 2019-06-29
_olex2_date_sample_submission    2019-05-26
_olex2_submission_original_sample_id dmb_23
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_19051_0m
_database_code_depnum_ccdc_archive 'CCDC 1951270'
loop_
_audit_author_name
_audit_author_address
'Carta Veronica'
;Indiana University
United States of America
;
_audit_update_record             
;
2019-09-03 deposited with the CCDC.	2020-01-14 downloaded from the CCDC.
;
_audit_creation_date             2019-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
dbeagan@iu.edu
vcarta@iu.edu
caulton@indiana.edu
_chemical_name_common            ?
_chemical_name_systematic        (Bpin)2bpy
_chemical_formula_moiety         '0.5(C22 H32 B2 N2 O4)'
_chemical_formula_sum            'C11 H16 B N O2'
_chemical_formula_weight         205.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.5143(6)
_cell_length_b                   10.6792(9)
_cell_length_c                   16.5422(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.808(5)
_cell_angle_gamma                90
_cell_volume                     1137.23(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7792
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex3, (Bruker,2016)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_preparation       synthesized
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            22487
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.278
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER APEX DUO'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2692
_reflns_number_total             4619
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Apex3, (Bruker,2016)'
_computing_data_collection       'Apex3, (Bruker,2007)'
_computing_data_reduction        'Apex3, (Bruker,2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         4619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1765
_refine_special_details          'non-merohedral twinning'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.559(2)
 0.441(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2163(3) 0.76591(15) 0.91191(10) 0.0422(5) Uani 1 1 d . . . . .
O2 O -0.0951(2) 0.86420(13) 0.83625(9) 0.0502(5) Uani 1 1 d . . . . .
O3 O 0.1952(2) 0.98583(14) 0.87039(9) 0.0547(5) Uani 1 1 d . . . . .
C4 C 0.4446(3) 0.55160(17) 0.98423(11) 0.0376(5) Uani 1 1 d . . . . .
C5 C 0.5311(4) 0.67527(19) 0.98118(13) 0.0489(6) Uani 1 1 d . . . . .
H5 H 0.669423 0.687241 1.003764 0.059 Uiso 1 1 calc R . . . .
C6 C 0.2254(3) 0.54795(19) 0.94933(12) 0.0438(6) Uani 1 1 d . . . . .
H6 H 0.153799 0.472712 0.949972 0.053 Uiso 1 1 calc R . . . .
C7 C 0.1239(3) 0.64840(19) 0.91655(12) 0.0440(6) Uani 1 1 d . . . . .
H7 H -0.016286 0.639995 0.895584 0.053 Uiso 1 1 calc R . . . .
C8 C 0.4242(4) 0.7733(2) 0.94786(13) 0.0517(6) Uani 1 1 d . . . . .
H8 H 0.490987 0.850337 0.948544 0.062 Uiso 1 1 calc R . . . .
B9 B 0.1059(4) 0.8709(2) 0.87321(15) 0.0425(6) Uani 1 1 d . . . . .
C10 C -0.1342(4) 0.9818(2) 0.79015(13) 0.0468(6) Uani 1 1 d . . . . .
C11 C 0.0277(3) 1.0715(2) 0.83792(13) 0.0493(6) Uani 1 1 d . . . . .
C12 C -0.3573(4) 1.0200(2) 0.78883(16) 0.0693(8) Uani 1 1 d . . . . .
H12A H -0.446716 0.961448 0.756468 0.104 Uiso 1 1 calc GR . . . .
H12B H -0.378618 1.102181 0.765508 0.104 Uiso 1 1 calc GR . . . .
H12C H -0.388715 1.020770 0.843660 0.104 Uiso 1 1 calc GR . . . .
C13 C -0.0502(4) 1.1298(2) 0.91189(15) 0.0759(8) Uani 1 1 d . . . . .
H13A H -0.115608 1.066494 0.940356 0.114 Uiso 1 1 calc GR . . . .
H13B H -0.148755 1.194562 0.893871 0.114 Uiso 1 1 calc GR . . . .
H13C H 0.064957 1.164860 0.947947 0.114 Uiso 1 1 calc GR . . . .
C14 C 0.1135(4) 1.1704(2) 0.78774(17) 0.0772(9) Uani 1 1 d . . . . .
H14A H 0.213227 1.220251 0.822507 0.116 Uiso 1 1 calc GR . . . .
H14B H 0.002436 1.223013 0.762375 0.116 Uiso 1 1 calc GR . . . .
H14C H 0.179573 1.131213 0.746279 0.116 Uiso 1 1 calc GR . . . .
C15 C -0.0900(4) 0.9546(2) 0.70403(15) 0.0809(9) Uani 1 1 d . . . . .
H15A H 0.052256 0.929444 0.706468 0.121 Uiso 1 1 calc GR . . . .
H15B H -0.115083 1.028647 0.671103 0.121 Uiso 1 1 calc GR . . . .
H15C H -0.179499 0.888530 0.680272 0.121 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlateditions 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
N1 C7 1.399(2) . ?
N1 C8 1.395(3) . ?
N1 B9 1.430(3) . ?
O2 B9 1.360(3) . ?
O2 C10 1.471(2) . ?
O3 B9 1.362(3) . ?
O3 C11 1.462(2) . ?
C4 C4 1.375(4) 3_667 ?
C4 C5 1.440(3) . ?
C4 C6 1.457(3) . ?
C5 C8 1.329(3) . ?
C6 C7 1.331(3) . ?
C10 C11 1.549(3) . ?
C10 C12 1.507(3) . ?
C10 C15 1.524(3) . ?
C11 C13 1.527(3) . ?
C11 C14 1.503(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
C7 N1 B9 122.5(2) . . ?
C8 N1 C7 115.17(17) . . ?
C8 N1 B9 122.37(19) . . ?
B9 O2 C10 105.44(17) . . ?
B9 O3 C11 106.15(17) . . ?
C4 C4 C5 124.3(2) 3_667 . ?
C4 C4 C6 123.7(2) 3_667 . ?
C5 C4 C6 112.07(17) . . ?
C8 C5 C4 123.6(2) . . ?
C7 C6 C4 122.40(19) . . ?
C6 C7 N1 123.6(2) . . ?
C5 C8 N1 123.0(2) . . ?
O2 B9 N1 122.9(2) . . ?
O2 B9 O3 114.79(19) . . ?
O3 B9 N1 122.3(2) . . ?
O2 C10 C11 102.32(16) . . ?
O2 C10 C12 109.19(18) . . ?
O2 C10 C15 106.22(16) . . ?
C12 C10 C11 114.82(19) . . ?
C12 C10 C15 111.0(2) . . ?
C15 C10 C11 112.57(18) . . ?
O3 C11 C10 102.22(17) . . ?
O3 C11 C13 106.34(18) . . ?
O3 C11 C14 108.85(17) . . ?
C13 C11 C10 112.16(18) . . ?
C14 C11 C10 115.76(19) . . ?
C14 C11 C13 110.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C10 C11 O3 29.60(19) . . . . ?
O2 C10 C11 C13 -83.9(2) . . . . ?
O2 C10 C11 C14 147.73(19) . . . . ?
C4 C4 C5 C8 177.5(2) 3_667 . . . ?
C4 C4 C6 C7 -177.5(2) 3_667 . . . ?
C4 C5 C8 N1 -0.3(4) . . . . ?
C4 C6 C7 N1 0.4(3) . . . . ?
C5 C4 C6 C7 2.0(3) . . . . ?
C6 C4 C5 C8 -2.1(3) . . . . ?
C7 N1 C8 C5 2.8(3) . . . . ?
C7 N1 B9 O2 -1.7(3) . . . . ?
C7 N1 B9 O3 178.54(18) . . . . ?
C8 N1 C7 C6 -2.8(3) . . . . ?
C8 N1 B9 O2 178.37(19) . . . . ?
C8 N1 B9 O3 -1.4(3) . . . . ?
B9 N1 C7 C6 177.2(2) . . . . ?
B9 N1 C8 C5 -177.3(2) . . . . ?
B9 O2 C10 C11 -25.1(2) . . . . ?
B9 O2 C10 C12 -147.21(19) . . . . ?
B9 O2 C10 C15 93.1(2) . . . . ?
B9 O3 C11 C10 -23.7(2) . . . . ?
B9 O3 C11 C13 94.1(2) . . . . ?
B9 O3 C11 C14 -146.6(2) . . . . ?
C10 O2 B9 N1 -168.3(2) . . . . ?
C10 O2 B9 O3 11.4(2) . . . . ?
C11 O3 B9 N1 -171.5(2) . . . . ?
C11 O3 B9 O2 8.8(2) . . . . ?
C12 C10 C11 O3 147.75(18) . . . . ?
C12 C10 C11 C13 34.2(3) . . . . ?
C12 C10 C11 C14 -94.1(2) . . . . ?
C15 C10 C11 O3 -84.00(19) . . . . ?
C15 C10 C11 C13 162.47(18) . . . . ?
C15 C10 C11 C14 34.1(3) . . . . ?

_olex2_date_sample_data_collection 2019-05-03
_olex2_date_sample_submission    2019-05-03
_olex2_submission_original_sample_id dmb_19
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.559(2)
2 0.441(2)

