# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1486752'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-10-11 downloaded from the CCDC.
;

_exptl_crystal_recrystallization_method 
; 
 
;

#see the bottom part of the file for the full list of the applied restraints. 

#end of refcif 
_cell_length_a                   5.7992(5)
_cell_length_b                   11.4342(9)
_cell_length_c                   24.017(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1592.5(2)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,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 0.0137 0.0067 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'
Fe -0.2674 2.5551 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'
N 0.0241 0.0134 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'
O 0.0389 0.0241 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H19 Fe1 N1 O1 
# Dc =      1.44 Fooo =    720.00 Mu =     52.52 M =    345.22
# Found Formula = C20 H19 Fe1 N1 O1 
# Dc =      1.44 FOOO =    720.00 Mu =     52.52 M =    345.22

_chemical_formula_sum            'C20 H19 Fe1 N1 O1'
_chemical_formula_moiety         'C20 H19 Fe1 N1 O1'
_chemical_compound_source        ?
_chemical_formula_weight         345.22


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_max          0.070

_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    5.252

# Sheldrick geometric approximatio 0.85 0.90 
# No experimental values of Tmin/max available 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_device       Area
_diffrn_detector                 Pilatus300K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Metaljet D2'
_diffrn_source_voltage           70
_diffrn_source_current           2.860
_diffrn_source_power             0.200
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'STOE X-AREA (Stoe & Cie 2011)'
_computing_cell_refinement       'STOE X-AREA (Stoe & Cie 2011)'
_computing_data_reduction        'STOE X-RED (Stoe & Cie 1996)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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      123
_diffrn_reflns_number            8073
_reflns_number_total             2832
_diffrn_reflns_av_R_equivalents  0.056
# Number of reflections without Friedels Law is 2832 
# Number of reflections with Friedels Law is 1728 
# Theoretical number of reflections is about 1481 


_diffrn_reflns_theta_min         3.202
_diffrn_reflns_theta_max         57.314
_diffrn_measured_fraction_theta_max 0.895

_diffrn_reflns_theta_full        52.800
_diffrn_measured_fraction_theta_full 0.976


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_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         -0.56
_refine_diff_density_max         0.28


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     336
_refine_ls_number_parameters     209
_oxford_refine_ls_R_factor_ref   0.0410
_refine_ls_wR_factor_ref         0.0498
_refine_ls_goodness_of_fit_ref   1.0725
_refine_ls_shift/su_max          0.0009632
_refine_ls_shift/su_mean         0.0000823


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2818
_refine_ls_R_factor_all          0.0496
_refine_ls_wR_factor_all         0.0542

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2501
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_gt          0.0511

_refine_ls_abs_structure_Flack   0.000(8)
_refine_ls_abs_structure_details 'Flack (1983), 1104 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.42 0.423 1.02 
;

# start Validation Reply Form
_vrf_PLAT183_1                   
;
PROBLEM: Missing _cell_measurement_reflns_used value ....     Please Do ! 
RESPONSE: The unit cell is refined at the end of the experiment using
all available reflections from the data collection
;
_vrf_PLAT184_1                   
;
PROBLEM: Missing _cell_measurement_theta_min value ......     Please Do ! 
RESPONSE: The unit cell is refined at the end of the experiment using
all available reflections from the data collection
;
_vrf_PLAT185_1                   
;
PROBLEM: Missing _cell_measurement_theta_max value ......     Please Do ! 
RESPONSE: The unit cell is refined at the end of the experiment using
all available reflections from the data collection
;
_vrf_PLAT920_1                   
;
PROBLEM: Theta(Max)  in CIF and FCF Differ by ...........       3.00 Degree
RESPONSE: Checkcif started in some moment to throw this alert, cif and fcf 
have been written together, thus reason of problem unknown
;
# end Validation Reply Form

# 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 0.32186(7) 0.23678(4) 0.799435(19) 0.0285 1.0000 Uani . U . . . .
N1 N 0.4287(5) 0.3436(3) 0.63158(13) 0.0337 1.0000 Uani . U . . . .
O1 O 0.0960(5) 0.3749(3) 0.68009(11) 0.0443 1.0000 Uani . U . . . .
C1 C 0.1114(10) 0.3725(4) 0.82175(18) 0.0639 1.0000 Uani . U . . . .
C2 C 0.0533(6) 0.2723(4) 0.85139(16) 0.0475 1.0000 Uani . U . . . .
C3 C 0.2414(7) 0.2363(4) 0.88173(14) 0.0435 1.0000 Uani . U . . . .
C4 C 0.4250(7) 0.3140(5) 0.87219(19) 0.0578 1.0000 Uani . U . . . .
C5 C 0.3417(12) 0.3999(4) 0.8344(2) 0.0702 1.0000 Uani . U . . . .
C6 C 0.3537(5) 0.2300(3) 0.71531(13) 0.0303 1.0000 Uani . U . . . .
C7 C 0.2037(6) 0.1397(3) 0.73459(14) 0.0332 1.0000 Uani . U . . . .
C8 C 0.3292(7) 0.0676(3) 0.77171(15) 0.0348 1.0000 Uani . U . . . .
C9 C 0.5577(6) 0.1125(3) 0.77575(15) 0.0349 1.0000 Uani . U . . . .
C10 C 0.5718(6) 0.2135(3) 0.74073(13) 0.0317 1.0000 Uani . U . . . .
C11 C 0.2801(6) 0.3213(3) 0.67477(14) 0.0320 1.0000 Uani . U . . . .
C12 C 0.3973(7) 0.4296(3) 0.58987(15) 0.0355 1.0000 Uani . U . . . .
C13 C 0.2268(8) 0.5144(3) 0.58467(17) 0.0444 1.0000 Uani . U . . . .
C14 C 0.2363(9) 0.5890(4) 0.53897(18) 0.0520 1.0000 Uani . U . . . .
C15 C 0.4089(8) 0.5821(4) 0.50009(17) 0.0518 1.0000 Uani . U . . . .
C16 C 0.5797(8) 0.4977(4) 0.50657(17) 0.0513 1.0000 Uani . U . . . .
C17 C 0.5750(7) 0.4214(3) 0.55063(16) 0.0425 1.0000 Uani . U . . . .
C18 C 0.7377(8) 0.3246(4) 0.56717(19) 0.0538 1.0000 Uani . U . . . .
C19 C 0.6066(6) 0.2572(4) 0.61182(14) 0.0419 1.0000 Uani . U . . . .
C20 C 0.4810(11) 0.1504(4) 0.5884(2) 0.0596 1.0000 Uani . U . . . .
H11 H 0.0132 0.4145 0.7957 0.0741 1.0000 Uiso R . . . . .
H21 H -0.0934 0.2307 0.8492 0.0556 1.0000 Uiso R . . . . .
H31 H 0.2545 0.1684 0.9065 0.0495 1.0000 Uiso R . . . . .
H41 H 0.5827 0.3113 0.8876 0.0662 1.0000 Uiso R . . . . .
H51 H 0.4277 0.4677 0.8199 0.0808 1.0000 Uiso R . . . . .
H71 H 0.0422 0.1314 0.7245 0.0386 1.0000 Uiso R . . . . .
H81 H 0.2688 0.0036 0.7939 0.0412 1.0000 Uiso R . . . . .
H91 H 0.6792 0.0855 0.8005 0.0403 1.0000 Uiso R . . . . .
H101 H 0.7007 0.2673 0.7379 0.0355 1.0000 Uiso R . . . . .
H131 H 0.1105 0.5224 0.6106 0.0512 1.0000 Uiso R . . . . .
H141 H 0.1219 0.6467 0.5351 0.0610 1.0000 Uiso R . . . . .
H151 H 0.4147 0.6324 0.4694 0.0599 1.0000 Uiso R . . . . .
H161 H 0.6991 0.4922 0.4810 0.0613 1.0000 Uiso R . . . . .
H181 H 0.7721 0.2741 0.5353 0.0619 1.0000 Uiso R . . . . .
H182 H 0.8794 0.3579 0.5820 0.0624 1.0000 Uiso R . . . . .
H191 H 0.7018 0.2321 0.6437 0.0488 1.0000 Uiso R . . . . .
H201 H 0.3784 0.1763 0.5588 0.0869 1.0000 Uiso R . . . . .
H202 H 0.5878 0.0943 0.5731 0.0867 1.0000 Uiso R . . . . .
H203 H 0.3892 0.1123 0.6168 0.0866 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.6607(16)
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 . C1 . 2.046(4) yes
Fe1 . C2 . 2.036(4) yes
Fe1 . C3 . 2.031(4) yes
Fe1 . C4 . 2.047(4) yes
Fe1 . C5 . 2.049(4) yes
Fe1 . C6 . 2.030(3) yes
Fe1 . C7 . 2.032(3) yes
Fe1 . C8 . 2.046(3) yes
Fe1 . C9 . 2.053(4) yes
Fe1 . C10 . 2.040(3) yes
N1 . C11 . 1.372(5) yes
N1 . C12 . 1.415(5) yes
N1 . C19 . 1.505(4) yes
O1 . C11 . 1.237(4) yes
C1 . C2 . 1.390(7) yes
C1 . C5 . 1.405(8) yes
C1 . H11 . 0.973 no
C2 . C3 . 1.375(6) yes
C2 . H21 . 0.976 no
C3 . C4 . 1.406(7) yes
C3 . H31 . 0.982 no
C4 . C5 . 1.422(8) yes
C4 . H41 . 0.987 no
C5 . H51 . 0.985 no
C6 . C7 . 1.427(5) yes
C6 . C10 . 1.417(5) yes
C6 . C11 . 1.491(5) yes
C7 . C8 . 1.416(5) yes
C7 . H71 . 0.972 no
C8 . C9 . 1.424(5) yes
C8 . H81 . 0.971 no
C9 . C10 . 1.432(5) yes
C9 . H91 . 0.972 no
C10 . H101 . 0.970 no
C12 . C13 . 1.391(6) yes
C12 . C17 . 1.400(6) yes
C13 . C14 . 1.391(6) yes
C13 . H131 . 0.923 no
C14 . C15 . 1.371(7) yes
C14 . H141 . 0.941 no
C15 . C16 . 1.392(7) yes
C15 . H151 . 0.936 no
C16 . C17 . 1.371(6) yes
C16 . H161 . 0.928 no
C17 . C18 . 1.508(6) yes
C18 . C19 . 1.524(6) yes
C18 . H181 . 0.980 no
C18 . H182 . 0.973 no
C19 . C20 . 1.529(7) yes
C19 . H191 . 0.987 no
C20 . H201 . 0.972 no
C20 . H202 . 0.964 no
C20 . H203 . 0.970 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
C1 . Fe1 . C2 . 39.8(2) yes
C1 . Fe1 . C3 . 67.06(17) yes
C2 . Fe1 . C3 . 39.52(17) yes
C1 . Fe1 . C4 . 67.9(2) yes
C2 . Fe1 . C4 . 67.33(16) yes
C3 . Fe1 . C4 . 40.34(19) yes
C1 . Fe1 . C5 . 40.1(2) yes
C2 . Fe1 . C5 . 67.07(19) yes
C3 . Fe1 . C5 . 67.47(17) yes
C4 . Fe1 . C5 . 40.6(2) yes
C1 . Fe1 . C6 . 110.13(15) yes
C2 . Fe1 . C6 . 133.39(14) yes
C3 . Fe1 . C6 . 171.61(15) yes
C4 . Fe1 . C6 . 147.07(17) yes
C5 . Fe1 . C6 . 115.95(16) yes
C1 . Fe1 . C7 . 114.46(18) yes
C2 . Fe1 . C7 . 108.70(15) yes
C3 . Fe1 . C7 . 131.83(15) yes
C4 . Fe1 . C7 . 171.34(19) yes
C5 . Fe1 . C7 . 146.2(2) yes
C1 . Fe1 . C8 . 144.6(2) yes
C2 . Fe1 . C8 . 113.80(16) yes
C3 . Fe1 . C8 . 108.58(15) yes
C4 . Fe1 . C8 . 132.81(19) yes
C5 . Fe1 . C8 . 173.2(2) yes
C1 . Fe1 . C9 . 174.4(2) yes
C2 . Fe1 . C9 . 144.81(18) yes
C3 . Fe1 . C9 . 114.87(15) yes
C4 . Fe1 . C9 . 109.91(17) yes
C5 . Fe1 . C9 . 135.0(2) yes
C1 . Fe1 . C10 . 134.76(18) yes
C2 . Fe1 . C10 . 173.26(16) yes
C3 . Fe1 . C10 . 146.68(15) yes
C4 . Fe1 . C10 . 116.01(15) yes
C5 . Fe1 . C10 . 111.23(17) yes
C6 . Fe1 . C7 . 41.14(13) yes
C6 . Fe1 . C8 . 68.78(14) yes
C7 . Fe1 . C8 . 40.62(14) yes
C6 . Fe1 . C9 . 68.72(14) yes
C7 . Fe1 . C9 . 68.53(14) yes
C8 . Fe1 . C9 . 40.67(15) yes
C6 . Fe1 . C10 . 40.75(13) yes
C7 . Fe1 . C10 . 68.82(14) yes
C8 . Fe1 . C10 . 68.72(14) yes
C9 . Fe1 . C10 . 40.95(14) yes
C11 . N1 . C12 . 125.6(3) yes
C11 . N1 . C19 . 123.2(3) yes
C12 . N1 . C19 . 108.7(3) yes
Fe1 . C1 . C2 . 69.7(2) yes
Fe1 . C1 . C5 . 70.1(2) yes
C2 . C1 . C5 . 107.7(4) yes
Fe1 . C1 . H11 . 123.8 no
C2 . C1 . H11 . 126.5 no
C5 . C1 . H11 . 125.8 no
C1 . C2 . Fe1 . 70.4(2) yes
C1 . C2 . C3 . 109.0(4) yes
Fe1 . C2 . C3 . 70.0(2) yes
C1 . C2 . H21 . 125.8 no
Fe1 . C2 . H21 . 122.5 no
C3 . C2 . H21 . 125.0 no
C2 . C3 . Fe1 . 70.5(2) yes
C2 . C3 . C4 . 109.0(4) yes
Fe1 . C3 . C4 . 70.5(2) yes
C2 . C3 . H31 . 128.3 no
Fe1 . C3 . H31 . 125.1 no
C4 . C3 . H31 . 122.7 no
C3 . C4 . Fe1 . 69.2(2) yes
C3 . C4 . C5 . 106.5(4) yes
Fe1 . C4 . C5 . 69.7(2) yes
C3 . C4 . H41 . 128.3 no
Fe1 . C4 . H41 . 125.2 no
C5 . C4 . H41 . 125.2 no
C4 . C5 . C1 . 107.9(4) yes
C4 . C5 . Fe1 . 69.6(2) yes
C1 . C5 . Fe1 . 69.8(2) yes
C4 . C5 . H51 . 126.6 no
C1 . C5 . H51 . 125.5 no
Fe1 . C5 . H51 . 126.9 no
Fe1 . C6 . C7 . 69.48(19) yes
Fe1 . C6 . C10 . 69.98(18) yes
C7 . C6 . C10 . 108.0(3) yes
Fe1 . C6 . C11 . 126.7(2) yes
C7 . C6 . C11 . 123.0(3) yes
C10 . C6 . C11 . 129.0(3) yes
C6 . C7 . Fe1 . 69.38(19) yes
C6 . C7 . C8 . 108.2(3) yes
Fe1 . C7 . C8 . 70.25(19) yes
C6 . C7 . H71 . 125.3 no
Fe1 . C7 . H71 . 124.7 no
C8 . C7 . H71 . 126.5 no
C7 . C8 . Fe1 . 69.13(18) yes
C7 . C8 . C9 . 108.1(3) yes
Fe1 . C8 . C9 . 69.9(2) yes
C7 . C8 . H81 . 126.8 no
Fe1 . C8 . H81 . 121.8 no
C9 . C8 . H81 . 124.7 no
C8 . C9 . Fe1 . 69.42(19) yes
C8 . C9 . C10 . 107.7(3) yes
Fe1 . C9 . C10 . 69.03(19) yes
C8 . C9 . H91 . 127.0 no
Fe1 . C9 . H91 . 122.2 no
C10 . C9 . H91 . 125.0 no
C9 . C10 . C6 . 108.0(3) yes
C9 . C10 . Fe1 . 70.02(19) yes
C6 . C10 . Fe1 . 69.27(19) yes
C9 . C10 . H101 . 126.7 no
C6 . C10 . H101 . 125.0 no
Fe1 . C10 . H101 . 120.9 no
C6 . C11 . N1 . 116.3(3) yes
C6 . C11 . O1 . 121.8(3) yes
N1 . C11 . O1 . 121.9(3) yes
N1 . C12 . C13 . 129.8(4) yes
N1 . C12 . C17 . 109.6(3) yes
C13 . C12 . C17 . 120.6(3) yes
C12 . C13 . C14 . 118.1(4) yes
C12 . C13 . H131 . 121.8 no
C14 . C13 . H131 . 120.1 no
C13 . C14 . C15 . 122.1(4) yes
C13 . C14 . H141 . 118.7 no
C15 . C14 . H141 . 119.2 no
C14 . C15 . C16 . 118.9(4) yes
C14 . C15 . H151 . 121.8 no
C16 . C15 . H151 . 119.3 no
C15 . C16 . C17 . 120.9(4) yes
C15 . C16 . H161 . 120.2 no
C17 . C16 . H161 . 118.9 no
C12 . C17 . C16 . 119.5(4) yes
C12 . C17 . C18 . 109.4(3) yes
C16 . C17 . C18 . 131.1(4) yes
C17 . C18 . C19 . 104.2(3) yes
C17 . C18 . H181 . 110.7 no
C19 . C18 . H181 . 110.7 no
C17 . C18 . H182 . 109.7 no
C19 . C18 . H182 . 111.2 no
H181 . C18 . H182 . 110.2 no
C18 . C19 . N1 . 103.4(3) yes
C18 . C19 . C20 . 112.5(4) yes
N1 . C19 . C20 . 108.3(3) yes
C18 . C19 . H191 . 114.5 no
N1 . C19 . H191 . 109.2 no
C20 . C19 . H191 . 108.7 no
C19 . C20 . H201 . 108.5 no
C19 . C20 . H202 . 111.4 no
H201 . C20 . H202 . 108.6 no
C19 . C20 . H203 . 111.1 no
H201 . C20 . H203 . 108.4 no
H202 . C20 . H203 . 108.8 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
C19 . H191 . C10 . 126 0.99 2.46 3.142(6) 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_1
_database_code_depnum_ccdc_archive 'CCDC 1486753'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-10-11 downloaded from the CCDC.
;

_exptl_crystal_recrystallization_method 
; 
 
;

#see the bottom part of the file for the full list of the applied restraints. 

#end of refcif 
_cell_length_a                   9.7138(5)
_cell_length_b                   9.7138(5)
_cell_length_c                   33.882(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2768.7(3)

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 32'
_symmetry_space_group_name_Hall  'P 32'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y,x-y,z+2/3
-x+y,-x,z+1/3

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 0.0137 0.0067 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'
Fe -0.2674 2.5551 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'
N 0.0241 0.0134 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'
O 0.0389 0.0241 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            6

# Given Formula = C22 H21 Fe1 N1 O3 
# Dc =      1.45 Fooo =   1260.00 Mu =     46.40 M =    403.26
# Found Formula = C22 H21 Fe1 N1 O3 
# Dc =      1.45 FOOO =   1259.99 Mu =     46.40 M =    403.26

_chemical_formula_sum            'C22 H21 Fe1 N1 O3'
_chemical_formula_moiety         'C22 H21 Fe1 N1 O3'
_chemical_compound_source        ?
_chemical_formula_weight         403.26


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_max          0.110

_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1259.993
_exptl_absorpt_coefficient_mu    4.640

# Sheldrick geometric approximatio 0.72 0.87 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_device       Area
_diffrn_detector                 Pilatus300K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Metaljet D2'
_diffrn_source_voltage           70
_diffrn_source_current           2.860
_diffrn_source_power             0.200
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'STOE X-AREA (Stoe & Cie 2011)'
_computing_cell_refinement       'STOE X-AREA (Stoe & Cie 2011)'
_computing_data_reduction        'STOE X-RED (Stoe & Cie 1996)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      123
_diffrn_reflns_number            17736
_reflns_number_total             5109
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections without Friedels Law is 5109 
# Number of reflections with Friedels Law is 3617 
# Theoretical number of reflections is about 3823 


_diffrn_reflns_theta_min         3.405
_diffrn_reflns_theta_max         57.346
_diffrn_measured_fraction_theta_max 0.948

_diffrn_reflns_theta_full        52.800
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       26
_reflns_limit_h_min              -11
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              -41
_reflns_limit_l_max              26

_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         -0.39
_refine_diff_density_max         0.67


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>1.0\s(I)
_refine_ls_number_reflns         4747
_refine_ls_number_restraints     1
_refine_ls_number_parameters     489
_oxford_refine_ls_R_factor_ref   0.0369
_refine_ls_wR_factor_ref         0.0402
_refine_ls_goodness_of_fit_ref   1.0750
_refine_ls_shift/su_max          0.0003095
_refine_ls_shift/su_mean         0.0000331


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5109
_refine_ls_R_factor_all          0.0399
_refine_ls_wR_factor_all         0.0444

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4478
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_gt          0.0391

_refine_ls_abs_structure_Flack   0.024(6)
_refine_ls_abs_structure_details 'Flack (1983), 1492 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.455 0.276 0.108 
;

# start Validation Reply Form
_vrf_PLAT183_1                   
;
PROBLEM: Missing _cell_measurement_reflns_used value ....     Please Do ! 
RESPONSE: The unit cell is refined at the end of the experiment using
all available reflections from the data collection
;
_vrf_PLAT184_1                   
;
PROBLEM: Missing _cell_measurement_theta_min value ......     Please Do ! 
RESPONSE: The unit cell is refined at the end of the experiment using
all available reflections from the data collection
;
_vrf_PLAT185_1                   
;
PROBLEM: Missing _cell_measurement_theta_max value ......     Please Do ! 
RESPONSE: The unit cell is refined at the end of the experiment using
all available reflections from the data collection
;
# end Validation Reply Form

# 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 0.33686(7) -0.30842(6) 0.37913(4) 0.0274 1.0000 Uani . . . . . .
N1 N 0.2828(4) 0.0102(4) 0.30659(10) 0.0320 1.0000 Uani . . . . . .
O1 O 0.4899(3) -0.0326(4) 0.30312(9) 0.0436 1.0000 Uani . . . . . .
O2 O 0.5007(4) 0.2055(4) 0.36057(9) 0.0483 1.0000 Uani . . . . . .
O3 O 0.6436(4) 0.3866(5) 0.31461(11) 0.0564 1.0000 Uani . . . . . .
C1 C 0.5640(5) -0.1335(5) 0.38937(14) 0.0438 1.0000 Uani . . . . . .
C2 C 0.4711(5) -0.1619(5) 0.42411(14) 0.0417 1.0000 Uani . . . . . .
C3 C 0.4088(5) -0.3221(5) 0.43490(13) 0.0400 1.0000 Uani . . . . . .
C4 C 0.4653(5) -0.3938(5) 0.40738(14) 0.0397 1.0000 Uani . . . . . .
C5 C 0.5610(5) -0.2760(6) 0.37944(15) 0.0437 1.0000 Uani . . . . . .
C6 C 0.2528(4) -0.2358(5) 0.33320(12) 0.0313 1.0000 Uani . . . . . .
C7 C 0.1580(4) -0.2619(4) 0.36795(12) 0.0305 1.0000 Uani . . . . . .
C8 C 0.0942(4) -0.4226(4) 0.37957(14) 0.0344 1.0000 Uani . . . . . .
C9 C 0.1488(4) -0.4960(4) 0.35237(14) 0.0405 1.0000 Uani . . . . . .
C10 C 0.2480(5) -0.3823(5) 0.32425(14) 0.0371 1.0000 Uani . . . . . .
C11 C 0.3487(5) -0.0843(5) 0.31268(11) 0.0330 1.0000 Uani . . . . . .
C12 C 0.1195(5) -0.0352(5) 0.30227(12) 0.0310 1.0000 Uani . . . . . .
C13 C -0.0122(5) -0.1835(6) 0.29801(13) 0.0377 1.0000 Uani . . . . . .
C14 C -0.1585(5) -0.1937(6) 0.29240(15) 0.0430 1.0000 Uani . . . . . .
C15 C -0.1729(5) -0.0584(6) 0.29061(15) 0.0427 1.0000 Uani . . . . . .
C16 C -0.0376(6) 0.0905(6) 0.29332(14) 0.0403 1.0000 Uani . . . . . .
C17 C 0.1080(5) 0.1023(5) 0.29878(12) 0.0323 1.0000 Uani . . . . . .
C18 C 0.2703(5) 0.2478(5) 0.30346(13) 0.0373 1.0000 Uani . . . . . .
C19 C 0.3839(5) 0.1805(5) 0.29687(12) 0.0335 1.0000 Uani . . . . . .
C20 C 0.4401(5) 0.2027(5) 0.25412(11) 0.0327 1.0000 Uani . . . . . .
C21 C 0.5191(7) 0.2586(7) 0.32572(15) 0.0521 1.0000 Uani . . . . . .
C22 C 0.6494(6) 0.3120(6) 0.38565(15) 0.0587 1.0000 Uani . . . . . .
H11 H 0.6194 -0.0338 0.3748 0.0518 1.0000 Uiso R . . . . .
H21 H 0.4510 -0.0837 0.4371 0.0491 1.0000 Uiso R . . . . .
H31 H 0.3361 -0.3724 0.4570 0.0472 1.0000 Uiso R . . . . .
H41 H 0.4356 -0.5047 0.4062 0.0485 1.0000 Uiso R . . . . .
H51 H 0.6138 -0.2916 0.3567 0.0508 1.0000 Uiso R . . . . .
H71 H 0.1419 -0.1806 0.3810 0.0361 1.0000 Uiso R . . . . .
H81 H 0.0223 -0.4735 0.4019 0.0408 1.0000 Uiso R . . . . .
H91 H 0.1284 -0.6073 0.3543 0.0482 1.0000 Uiso R . . . . .
H101 H 0.3038 -0.3985 0.3015 0.0446 1.0000 Uiso R . . . . .
H131 H -0.0050 -0.2741 0.2991 0.0439 1.0000 Uiso R . . . . .
H141 H -0.2466 -0.2926 0.2898 0.0494 1.0000 Uiso R . . . . .
H151 H -0.2726 -0.0651 0.2869 0.0521 1.0000 Uiso R . . . . .
H161 H -0.0439 0.1806 0.2910 0.0458 1.0000 Uiso R . . . . .
H181 H 0.2908 0.3305 0.2844 0.0440 1.0000 Uiso R . . . . .
H182 H 0.2840 0.2929 0.3300 0.0437 1.0000 Uiso R . . . . .
H201 H 0.5046 0.3143 0.2476 0.0475 1.0000 Uiso R . . . . .
H202 H 0.5007 0.1525 0.2502 0.0478 1.0000 Uiso R . . . . .
H203 H 0.3503 0.1567 0.2370 0.0478 1.0000 Uiso R . . . . .
H221 H 0.7139 0.4225 0.3727 0.0946 1.0000 Uiso R . . . . .
H222 H 0.6160 0.3189 0.4139 0.0941 1.0000 Uiso R . . . . .
H223 H 0.7218 0.2704 0.3868 0.0949 1.0000 Uiso R . . . . .
Fe2 Fe 0.02479(6) 0.00356(7) 0.45678(4) 0.0271 1.0000 Uani . . . . . .
N2 N 0.3427(4) -0.0511(4) 0.52921(10) 0.0311 1.0000 Uani . . . . . .
O4 O 0.2989(4) 0.1554(3) 0.53280(9) 0.0423 1.0000 Uani . . . . . .
O5 O 0.7192(5) 0.3087(4) 0.52090(11) 0.0581 1.0000 Uani . . . . . .
O6 O 0.5394(4) 0.1682(4) 0.47579(10) 0.0499 1.0000 Uani . . . . . .
C23 C 0.2002(5) 0.2313(5) 0.44657(14) 0.0438 1.0000 Uani . . . . . .
C24 C 0.1714(5) 0.1374(5) 0.41248(14) 0.0439 1.0000 Uani . . . . . .
C25 C 0.0098(5) 0.0765(5) 0.40116(14) 0.0414 1.0000 Uani . . . . . .
C26 C -0.0590(5) 0.1331(5) 0.42859(15) 0.0418 1.0000 Uani . . . . . .
C27 C 0.0575(6) 0.2282(5) 0.45690(15) 0.0433 1.0000 Uani . . . . . .
C28 C 0.0970(5) -0.0804(4) 0.50278(12) 0.0308 1.0000 Uani . . . . . .
C29 C 0.0712(4) -0.1760(4) 0.46819(12) 0.0303 1.0000 Uani . . . . . .
C30 C -0.0899(4) -0.2397(4) 0.45624(14) 0.0344 1.0000 Uani . . . . . .
C31 C -0.1645(4) -0.1853(4) 0.48336(14) 0.0385 1.0000 Uani . . . . . .
C32 C -0.0502(5) -0.0862(5) 0.51184(14) 0.0363 1.0000 Uani . . . . . .
C33 C 0.2500(5) 0.0180(5) 0.52317(11) 0.0344 1.0000 Uani . . . . . .
C34 C 0.2997(5) -0.2126(5) 0.53376(13) 0.0333 1.0000 Uani . . . . . .
C35 C 0.1499(5) -0.3462(5) 0.53803(13) 0.0364 1.0000 Uani . . . . . .
C36 C 0.1409(6) -0.4924(6) 0.54393(14) 0.0426 1.0000 Uani . . . . . .
C37 C 0.2762(6) -0.5054(5) 0.54627(14) 0.0416 1.0000 Uani . . . . . .
C38 C 0.4248(6) -0.3717(6) 0.54262(14) 0.0403 1.0000 Uani . . . . . .
C39 C 0.4368(5) -0.2237(5) 0.53672(13) 0.0326 1.0000 Uani . . . . . .
C40 C 0.5800(5) -0.0639(5) 0.53259(13) 0.0365 1.0000 Uani . . . . . .
C41 C 0.5141(5) 0.0510(5) 0.53926(12) 0.0328 1.0000 Uani . . . . . .
C42 C 0.5358(5) 0.1077(5) 0.58166(11) 0.0350 1.0000 Uani . . . . . .
C43 C 0.5946(7) 0.1877(7) 0.51040(16) 0.0529 1.0000 Uani . . . . . .
C44 C 0.7739(10) 0.4169(9) 0.4899(2) 0.1196 1.0000 Uani . . . . . .
H231 H 0.2972 0.2817 0.4616 0.0522 1.0000 Uiso R . . . . .
H241 H 0.2475 0.1152 0.3993 0.0498 1.0000 Uiso R . . . . .
H251 H -0.0453 0.0048 0.3788 0.0493 1.0000 Uiso R . . . . .
H261 H -0.1697 0.1105 0.4277 0.0484 1.0000 Uiso R . . . . .
H271 H 0.0443 0.2831 0.4790 0.0503 1.0000 Uiso R . . . . .
H291 H 0.1517 -0.1934 0.4553 0.0350 1.0000 Uiso R . . . . .
H301 H -0.1403 -0.3046 0.4325 0.0397 1.0000 Uiso R . . . . .
H311 H -0.2711 -0.2049 0.4810 0.0456 1.0000 Uiso R . . . . .
H321 H -0.0683 -0.0315 0.5333 0.0424 1.0000 Uiso R . . . . .
H351 H 0.0576 -0.3388 0.5372 0.0445 1.0000 Uiso R . . . . .
H361 H 0.0405 -0.5864 0.5466 0.0511 1.0000 Uiso R . . . . .
H371 H 0.2663 -0.6040 0.5502 0.0487 1.0000 Uiso R . . . . .
H381 H 0.5178 -0.3791 0.5443 0.0474 1.0000 Uiso R . . . . .
H401 H 0.6268 -0.0483 0.5063 0.0444 1.0000 Uiso R . . . . .
H402 H 0.6592 -0.0471 0.5523 0.0442 1.0000 Uiso R . . . . .
H421 H 0.4832 0.1699 0.5849 0.0517 1.0000 Uiso R . . . . .
H422 H 0.6444 0.1687 0.5873 0.0519 1.0000 Uiso R . . . . .
H423 H 0.4855 0.0129 0.5981 0.0514 1.0000 Uiso R . . . . .
H441 H 0.6838 0.4299 0.4812 0.1909 1.0000 Uiso R . . . . .
H442 H 0.8619 0.5179 0.4991 0.1912 1.0000 Uiso R . . . . .
H443 H 0.8060 0.3735 0.4683 0.1914 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       21.1(17)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.3426(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 . C1 . 2.031(4) yes
Fe1 . C2 . 2.047(4) yes
Fe1 . C3 . 2.042(4) yes
Fe1 . C4 . 2.048(4) yes
Fe1 . C5 . 2.039(4) yes
Fe1 . C6 . 2.040(4) yes
Fe1 . C7 . 2.038(3) yes
Fe1 . C8 . 2.042(4) yes
Fe1 . C9 . 2.037(4) yes
Fe1 . C10 . 2.025(4) yes
N1 . C11 . 1.372(4) yes
N1 . C12 . 1.426(5) yes
N1 . C19 . 1.478(5) yes
O1 . C11 . 1.245(5) yes
O2 . C21 . 1.265(6) yes
O2 . C22 . 1.544(6) yes
O3 . C21 . 1.283(7) yes
C1 . C2 . 1.424(7) yes
C1 . C5 . 1.411(7) yes
C1 . H11 . 0.975 no
C2 . C3 . 1.407(6) yes
C2 . H21 . 0.979 no
C3 . C4 . 1.428(7) yes
C3 . H31 . 0.975 no
C4 . C5 . 1.417(6) yes
C4 . H41 . 0.966 no
C5 . H51 . 0.979 no
C6 . C7 . 1.437(5) yes
C6 . C10 . 1.433(5) yes
C6 . C11 . 1.465(6) yes
C7 . C8 . 1.417(5) yes
C7 . H71 . 0.983 no
C8 . C9 . 1.420(6) yes
C8 . H81 . 0.981 no
C9 . C10 . 1.411(7) yes
C9 . H91 . 0.999 no
C10 . H101 . 0.999 no
C12 . C13 . 1.374(6) yes
C12 . C17 . 1.400(6) yes
C13 . C14 . 1.388(6) yes
C13 . H131 . 0.918 no
C14 . C15 . 1.391(7) yes
C14 . H141 . 0.917 no
C15 . C16 . 1.388(7) yes
C15 . H151 . 0.946 no
C16 . C17 . 1.373(6) yes
C16 . H161 . 0.911 no
C17 . C18 . 1.510(6) yes
C18 . C19 . 1.554(5) yes
C18 . H181 . 0.971 no
C18 . H182 . 0.980 no
C19 . C20 . 1.525(5) yes
C19 . C21 . 1.504(6) yes
C20 . H201 . 0.968 no
C20 . H202 . 0.944 no
C20 . H203 . 0.953 no
C22 . H221 . 1.031 no
C22 . H222 . 1.022 no
C22 . H223 . 0.972 no
Fe2 . C23 . 2.037(4) yes
Fe2 . C24 . 2.030(4) yes
Fe2 . C25 . 2.044(4) yes
Fe2 . C26 . 2.045(4) yes
Fe2 . C27 . 2.042(4) yes
Fe2 . C28 . 2.039(4) yes
Fe2 . C29 . 2.045(3) yes
Fe2 . C30 . 2.048(4) yes
Fe2 . C31 . 2.045(4) yes
Fe2 . C32 . 2.034(4) yes
N2 . C33 . 1.381(4) yes
N2 . C34 . 1.416(5) yes
N2 . C41 . 1.490(5) yes
O4 . C33 . 1.216(5) yes
O5 . C43 . 1.245(7) yes
O5 . C44 . 1.390(8) yes
O6 . C43 . 1.263(6) yes
C23 . C24 . 1.411(7) yes
C23 . C27 . 1.415(7) yes
C23 . H231 . 0.963 no
C24 . C25 . 1.425(6) yes
C24 . H241 . 0.975 no
C25 . C26 . 1.407(7) yes
C25 . H251 . 0.988 no
C26 . C27 . 1.417(6) yes
C26 . H261 . 0.984 no
C27 . H271 . 0.965 no
C28 . C29 . 1.438(5) yes
C28 . C32 . 1.436(5) yes
C28 . C33 . 1.477(6) yes
C29 . C30 . 1.424(5) yes
C29 . H291 . 0.982 no
C30 . C31 . 1.425(6) yes
C30 . H301 . 0.988 no
C31 . C32 . 1.422(6) yes
C31 . H311 . 0.958 no
C32 . H321 . 0.968 no
C34 . C35 . 1.390(6) yes
C34 . C39 . 1.393(6) yes
C35 . C36 . 1.393(6) yes
C35 . H351 . 0.936 no
C36 . C37 . 1.384(7) yes
C36 . H361 . 0.950 no
C37 . C38 . 1.382(7) yes
C37 . H371 . 0.923 no
C38 . C39 . 1.397(6) yes
C38 . H381 . 0.943 no
C39 . C40 . 1.485(6) yes
C40 . C41 . 1.555(5) yes
C40 . H401 . 0.978 no
C40 . H402 . 0.969 no
C41 . C42 . 1.515(5) yes
C41 . C43 . 1.514(6) yes
C42 . H421 . 0.973 no
C42 . H422 . 0.936 no
C42 . H423 . 0.973 no
C44 . H441 . 0.991 no
C44 . H442 . 0.976 no
C44 . H443 . 0.970 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
C1 . Fe1 . C2 . 40.86(19) yes
C1 . Fe1 . C3 . 68.43(18) yes
C2 . Fe1 . C3 . 40.25(17) yes
C1 . Fe1 . C4 . 68.41(17) yes
C2 . Fe1 . C4 . 68.20(18) yes
C3 . Fe1 . C4 . 40.86(19) yes
C1 . Fe1 . C5 . 40.56(19) yes
C2 . Fe1 . C5 . 68.23(19) yes
C3 . Fe1 . C5 . 68.4(2) yes
C4 . Fe1 . C5 . 40.56(17) yes
C1 . Fe1 . C6 . 107.23(16) yes
C2 . Fe1 . C6 . 123.58(16) yes
C3 . Fe1 . C6 . 159.64(17) yes
C4 . Fe1 . C6 . 157.92(17) yes
C5 . Fe1 . C6 . 122.14(18) yes
C1 . Fe1 . C7 . 122.45(17) yes
C2 . Fe1 . C7 . 107.55(17) yes
C3 . Fe1 . C7 . 122.96(18) yes
C4 . Fe1 . C7 . 159.43(17) yes
C5 . Fe1 . C7 . 158.48(18) yes
C1 . Fe1 . C8 . 158.27(18) yes
C2 . Fe1 . C8 . 122.20(18) yes
C3 . Fe1 . C8 . 107.30(19) yes
C4 . Fe1 . C8 . 123.21(16) yes
C5 . Fe1 . C8 . 159.61(17) yes
C1 . Fe1 . C9 . 159.59(19) yes
C2 . Fe1 . C9 . 158.05(19) yes
C3 . Fe1 . C9 . 122.45(18) yes
C4 . Fe1 . C9 . 107.51(16) yes
C5 . Fe1 . C9 . 123.45(18) yes
C1 . Fe1 . C10 . 123.1(2) yes
C2 . Fe1 . C10 . 160.14(19) yes
C3 . Fe1 . C10 . 157.83(17) yes
C4 . Fe1 . C10 . 121.58(17) yes
C5 . Fe1 . C10 . 107.0(2) yes
C6 . Fe1 . C7 . 41.27(15) yes
C6 . Fe1 . C8 . 68.94(16) yes
C7 . Fe1 . C8 . 40.65(15) yes
C6 . Fe1 . C9 . 68.59(16) yes
C7 . Fe1 . C9 . 68.46(15) yes
C8 . Fe1 . C9 . 40.74(16) yes
C6 . Fe1 . C10 . 41.29(14) yes
C7 . Fe1 . C10 . 69.39(16) yes
C8 . Fe1 . C10 . 69.04(19) yes
C9 . Fe1 . C10 . 40.66(19) yes
C11 . N1 . C12 . 128.9(3) yes
C11 . N1 . C19 . 120.7(3) yes
C12 . N1 . C19 . 109.7(3) yes
C21 . O2 . C22 . 110.3(4) yes
Fe1 . C1 . C2 . 70.2(2) yes
Fe1 . C1 . C5 . 70.0(2) yes
C2 . C1 . C5 . 107.9(4) yes
Fe1 . C1 . H11 . 125.0 no
C2 . C1 . H11 . 126.3 no
C5 . C1 . H11 . 125.8 no
C1 . C2 . Fe1 . 69.0(2) yes
C1 . C2 . C3 . 108.0(4) yes
Fe1 . C2 . C3 . 69.7(2) yes
C1 . C2 . H21 . 125.2 no
Fe1 . C2 . H21 . 124.8 no
C3 . C2 . H21 . 126.8 no
C2 . C3 . Fe1 . 70.1(2) yes
C2 . C3 . C4 . 108.2(4) yes
Fe1 . C3 . C4 . 69.8(2) yes
C2 . C3 . H31 . 123.9 no
Fe1 . C3 . H31 . 123.8 no
C4 . C3 . H31 . 127.9 no
C3 . C4 . Fe1 . 69.3(2) yes
C3 . C4 . C5 . 107.4(4) yes
Fe1 . C4 . C5 . 69.4(2) yes
C3 . C4 . H41 . 126.6 no
Fe1 . C4 . H41 . 122.0 no
C5 . C4 . H41 . 125.7 no
C4 . C5 . C1 . 108.4(4) yes
C4 . C5 . Fe1 . 70.1(2) yes
C1 . C5 . Fe1 . 69.4(2) yes
C4 . C5 . H51 . 125.8 no
C1 . C5 . H51 . 125.7 no
Fe1 . C5 . H51 . 125.0 no
Fe1 . C6 . C7 . 69.3(2) yes
Fe1 . C6 . C10 . 68.8(2) yes
C7 . C6 . C10 . 107.3(4) yes
Fe1 . C6 . C11 . 123.1(3) yes
C7 . C6 . C11 . 126.6(3) yes
C10 . C6 . C11 . 125.9(4) yes
C6 . C7 . Fe1 . 69.5(2) yes
C6 . C7 . C8 . 108.1(3) yes
Fe1 . C7 . C8 . 69.85(19) yes
C6 . C7 . H71 . 124.8 no
Fe1 . C7 . H71 . 126.2 no
C8 . C7 . H71 . 127.1 no
C7 . C8 . Fe1 . 69.5(2) yes
C7 . C8 . C9 . 107.8(4) yes
Fe1 . C8 . C9 . 69.4(2) yes
C7 . C8 . H81 . 125.4 no
Fe1 . C8 . H81 . 128.2 no
C9 . C8 . H81 . 126.8 no
C8 . C9 . Fe1 . 69.8(2) yes
C8 . C9 . C10 . 109.0(3) yes
Fe1 . C9 . C10 . 69.2(2) yes
C8 . C9 . H91 . 125.4 no
Fe1 . C9 . H91 . 122.9 no
C10 . C9 . H91 . 125.4 no
C6 . C10 . C9 . 107.8(4) yes
C6 . C10 . Fe1 . 69.9(2) yes
C9 . C10 . Fe1 . 70.2(2) yes
C6 . C10 . H101 . 124.6 no
C9 . C10 . H101 . 127.6 no
Fe1 . C10 . H101 . 126.6 no
C6 . C11 . N1 . 117.9(3) yes
C6 . C11 . O1 . 123.2(3) yes
N1 . C11 . O1 . 118.7(4) yes
N1 . C12 . C13 . 130.0(4) yes
N1 . C12 . C17 . 108.7(4) yes
C13 . C12 . C17 . 121.0(4) yes
C12 . C13 . C14 . 118.2(4) yes
C12 . C13 . H131 . 121.6 no
C14 . C13 . H131 . 120.2 no
C13 . C14 . C15 . 121.4(5) yes
C13 . C14 . H141 . 118.3 no
C15 . C14 . H141 . 120.2 no
C14 . C15 . C16 . 119.5(4) yes
C14 . C15 . H151 . 121.6 no
C16 . C15 . H151 . 118.9 no
C15 . C16 . C17 . 119.7(4) yes
C15 . C16 . H161 . 120.8 no
C17 . C16 . H161 . 119.5 no
C12 . C17 . C16 . 120.1(4) yes
C12 . C17 . C18 . 109.9(3) yes
C16 . C17 . C18 . 130.0(4) yes
C17 . C18 . C19 . 102.7(3) yes
C17 . C18 . H181 . 113.0 no
C19 . C18 . H181 . 111.0 no
C17 . C18 . H182 . 111.1 no
C19 . C18 . H182 . 110.7 no
H181 . C18 . H182 . 108.3 no
C18 . C19 . N1 . 103.0(3) yes
C18 . C19 . C20 . 110.8(3) yes
N1 . C19 . C20 . 111.2(3) yes
C18 . C19 . C21 . 108.6(3) yes
N1 . C19 . C21 . 110.1(3) yes
C20 . C19 . C21 . 112.7(4) yes
C19 . C20 . H201 . 111.2 no
C19 . C20 . H202 . 109.4 no
H201 . C20 . H202 . 109.0 no
C19 . C20 . H203 . 109.5 no
H201 . C20 . H203 . 108.3 no
H202 . C20 . H203 . 109.5 no
C19 . C21 . O3 . 117.4(5) yes
C19 . C21 . O2 . 119.4(5) yes
O3 . C21 . O2 . 122.8(4) yes
O2 . C22 . H221 . 110.0 no
O2 . C22 . H222 . 109.7 no
H221 . C22 . H222 . 112.2 no
O2 . C22 . H223 . 111.8 no
H221 . C22 . H223 . 105.0 no
H222 . C22 . H223 . 108.0 no
C23 . Fe2 . C24 . 40.60(19) yes
C23 . Fe2 . C25 . 68.44(18) yes
C24 . Fe2 . C25 . 40.96(18) yes
C23 . Fe2 . C26 . 68.06(17) yes
C24 . Fe2 . C26 . 68.18(19) yes
C25 . Fe2 . C26 . 40.25(19) yes
C23 . Fe2 . C27 . 40.60(19) yes
C24 . Fe2 . C27 . 68.5(2) yes
C25 . Fe2 . C27 . 68.4(2) yes
C26 . Fe2 . C27 . 40.58(17) yes
C23 . Fe2 . C28 . 107.24(16) yes
C24 . Fe2 . C28 . 123.37(17) yes
C25 . Fe2 . C28 . 160.35(17) yes
C26 . Fe2 . C28 . 157.72(18) yes
C27 . Fe2 . C28 . 121.67(18) yes
C23 . Fe2 . C29 . 122.51(16) yes
C24 . Fe2 . C29 . 107.62(17) yes
C25 . Fe2 . C29 . 123.66(18) yes
C26 . Fe2 . C29 . 159.78(17) yes
C27 . Fe2 . C29 . 158.19(17) yes
C23 . Fe2 . C30 . 158.29(18) yes
C24 . Fe2 . C30 . 122.35(19) yes
C25 . Fe2 . C30 . 107.45(19) yes
C26 . Fe2 . C30 . 123.47(16) yes
C27 . Fe2 . C30 . 159.62(17) yes
C23 . Fe2 . C31 . 159.66(19) yes
C24 . Fe2 . C31 . 158.15(19) yes
C25 . Fe2 . C31 . 121.94(18) yes
C26 . Fe2 . C31 . 107.55(16) yes
C27 . Fe2 . C31 . 123.18(18) yes
C23 . Fe2 . C32 . 123.2(2) yes
C24 . Fe2 . C32 . 159.92(19) yes
C25 . Fe2 . C32 . 157.22(17) yes
C26 . Fe2 . C32 . 121.64(17) yes
C27 . Fe2 . C32 . 106.69(19) yes
C28 . Fe2 . C29 . 41.22(15) yes
C28 . Fe2 . C30 . 69.07(16) yes
C29 . Fe2 . C30 . 40.72(15) yes
C28 . Fe2 . C31 . 68.86(16) yes
C29 . Fe2 . C31 . 68.56(14) yes
C30 . Fe2 . C31 . 40.76(16) yes
C28 . Fe2 . C32 . 41.28(14) yes
C29 . Fe2 . C32 . 69.24(15) yes
C30 . Fe2 . C32 . 69.02(18) yes
C31 . Fe2 . C32 . 40.79(18) yes
C33 . N2 . C34 . 130.7(3) yes
C33 . N2 . C41 . 119.6(3) yes
C34 . N2 . C41 . 109.0(3) yes
C43 . O5 . C44 . 108.8(5) yes
Fe2 . C23 . C24 . 69.4(2) yes
Fe2 . C23 . C27 . 69.9(2) yes
C24 . C23 . C27 . 108.3(4) yes
Fe2 . C23 . H231 . 122.5 no
C24 . C23 . H231 . 126.1 no
C27 . C23 . H231 . 125.4 no
C23 . C24 . Fe2 . 70.0(2) yes
C23 . C24 . C25 . 108.0(4) yes
Fe2 . C24 . C25 . 70.1(2) yes
C23 . C24 . H241 . 126.2 no
Fe2 . C24 . H241 . 124.3 no
C25 . C24 . H241 . 125.7 no
C24 . C25 . Fe2 . 69.0(2) yes
C24 . C25 . C26 . 107.5(4) yes
Fe2 . C25 . C26 . 69.9(2) yes
C24 . C25 . H251 . 126.5 no
Fe2 . C25 . H251 . 124.8 no
C26 . C25 . H251 . 126.0 no
C25 . C26 . Fe2 . 69.8(2) yes
C25 . C26 . C27 . 108.7(4) yes
Fe2 . C26 . C27 . 69.6(2) yes
C25 . C26 . H261 . 124.9 no
Fe2 . C26 . H261 . 127.1 no
C27 . C26 . H261 . 126.3 no
C26 . C27 . C23 . 107.5(4) yes
C26 . C27 . Fe2 . 69.8(2) yes
C23 . C27 . Fe2 . 69.5(2) yes
C26 . C27 . H271 . 127.1 no
C23 . C27 . H271 . 125.4 no
Fe2 . C27 . H271 . 126.8 no
Fe2 . C28 . C29 . 69.6(2) yes
Fe2 . C28 . C32 . 69.2(2) yes
C29 . C28 . C32 . 107.5(4) yes
Fe2 . C28 . C33 . 122.3(3) yes
C29 . C28 . C33 . 126.4(3) yes
C32 . C28 . C33 . 125.9(4) yes
C28 . C29 . Fe2 . 69.18(19) yes
C28 . C29 . C30 . 108.1(3) yes
Fe2 . C29 . C30 . 69.8(2) yes
C28 . C29 . H291 . 125.3 no
Fe2 . C29 . H291 . 126.7 no
C30 . C29 . H291 . 126.5 no
C29 . C30 . Fe2 . 69.5(2) yes
C29 . C30 . C31 . 107.9(4) yes
Fe2 . C30 . C31 . 69.5(2) yes
C29 . C30 . H301 . 126.5 no
Fe2 . C30 . H301 . 123.6 no
C31 . C30 . H301 . 125.5 no
C30 . C31 . Fe2 . 69.7(2) yes
C30 . C31 . C32 . 108.6(3) yes
Fe2 . C31 . C32 . 69.2(2) yes
C30 . C31 . H311 . 124.9 no
Fe2 . C31 . H311 . 122.6 no
C32 . C31 . H311 . 126.2 no
C28 . C32 . C31 . 107.8(4) yes
C28 . C32 . Fe2 . 69.6(2) yes
C31 . C32 . Fe2 . 70.0(2) yes
C28 . C32 . H321 . 126.1 no
C31 . C32 . H321 . 126.0 no
Fe2 . C32 . H321 . 125.4 no
C28 . C33 . N2 . 116.4(3) yes
C28 . C33 . O4 . 123.4(3) yes
N2 . C33 . O4 . 120.1(4) yes
N2 . C34 . C35 . 129.6(4) yes
N2 . C34 . C39 . 109.3(4) yes
C35 . C34 . C39 . 121.0(4) yes
C34 . C35 . C36 . 118.0(4) yes
C34 . C35 . H351 . 121.4 no
C36 . C35 . H351 . 120.6 no
C35 . C36 . C37 . 121.5(5) yes
C35 . C36 . H361 . 120.3 no
C37 . C36 . H361 . 118.2 no
C36 . C37 . C38 . 120.1(4) yes
C36 . C37 . H371 . 119.4 no
C38 . C37 . H371 . 120.4 no
C37 . C38 . C39 . 119.4(4) yes
C37 . C38 . H381 . 120.8 no
C39 . C38 . H381 . 119.8 no
C38 . C39 . C34 . 119.9(4) yes
C38 . C39 . C40 . 129.9(4) yes
C34 . C39 . C40 . 110.1(3) yes
C39 . C40 . C41 . 103.3(3) yes
C39 . C40 . H401 . 111.6 no
C41 . C40 . H401 . 110.4 no
C39 . C40 . H402 . 111.1 no
C41 . C40 . H402 . 110.9 no
H401 . C40 . H402 . 109.4 no
C40 . C41 . N2 . 102.3(3) yes
C40 . C41 . C42 . 111.5(3) yes
N2 . C41 . C42 . 111.4(3) yes
C40 . C41 . C43 . 108.6(3) yes
N2 . C41 . C43 . 110.6(3) yes
C42 . C41 . C43 . 112.1(4) yes
C41 . C42 . H421 . 108.1 no
C41 . C42 . H422 . 109.4 no
H421 . C42 . H422 . 111.0 no
C41 . C42 . H423 . 106.7 no
H421 . C42 . H423 . 110.6 no
H422 . C42 . H423 . 110.8 no
C41 . C43 . O6 . 118.3(5) yes
C41 . C43 . O5 . 118.4(5) yes
O6 . C43 . O5 . 123.1(5) yes
O5 . C44 . H441 . 107.1 no
O5 . C44 . H442 . 109.3 no
H441 . C44 . H442 . 110.7 no
O5 . C44 . H443 . 109.0 no
H441 . C44 . H443 . 109.1 no
H442 . C44 . H443 . 111.6 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
C2 . H21 . O6 . 152 0.98 2.52 3.415(7) yes
C15 . H151 . O1 1_455 158 0.95 2.54 3.435(7) yes
C20 . H201 . O5 2_654 122 0.97 2.57 3.192(7) yes
C22 . H222 . O6 . 141 1.02 2.45 3.306(7) yes
C24 . H241 . O2 . 151 0.98 2.53 3.413(7) yes
C37 . H371 . O4 1_545 156 0.92 2.58 3.441(7) yes
C42 . H422 . O3 3_665 121 0.94 2.59 3.173(7) yes


