# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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 1493390'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H54 Br2 Fe N6 O2'
_chemical_formula_weight         914.60

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   17.7707(11)
_cell_length_b                   10.0076(8)
_cell_length_c                   25.4393(16)
_cell_angle_alpha                90
_cell_angle_beta                 108.204(3)
_cell_angle_gamma                90
_cell_volume                     4297.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    33054
_cell_measurement_theta_min      1.237
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             1888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.253
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33054
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.237
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7560
_reflns_number_gt                5883
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0980P)²+15.6741P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7560
_refine_ls_number_parameters     493
_refine_ls_number_restraints     65
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1791
_refine_ls_wR_factor_gt          0.1657
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.63333(4) 1.00895(6) 0.36547(3) 0.01529(18) Uani 1 1 d . . . . .
Br1 Br 0.60814(4) 1.01414(6) 0.26669(2) 0.0419(2) Uani 1 1 d . . . . .
Br4 Br 0.19180(3) 0.98889(5) 0.06307(2) 0.02760(17) Uani 1 1 d . . . . .
O1 O 0.2333(3) 0.9491(5) 0.43134(18) 0.0511(12) Uani 1 1 d . . . . .
N1 N 0.5617(2) 1.1960(4) 0.37085(15) 0.0182(8) Uani 1 1 d . . . . .
N2 N 0.7183(2) 1.2042(4) 0.45577(15) 0.0163(8) Uani 1 1 d . . . . .
N3 N 0.8046(2) 1.1447(4) 0.41831(15) 0.0170(8) Uani 1 1 d . . . . .
N4 N 0.7097(2) 0.8173(4) 0.38138(15) 0.0193(8) Uani 1 1 d . . . . .
N5 N 0.5968(2) 0.8105(4) 0.44503(15) 0.0178(8) Uani 1 1 d . . . . .
N6 N 0.4841(2) 0.8684(4) 0.39054(15) 0.0170(8) Uani 1 1 d . . . . .
C1 C 0.7287(3) 1.1210(4) 0.41686(18) 0.0160(9) Uani 1 1 d . . . . .
C2 C 0.8398(3) 1.2416(5) 0.45739(19) 0.0216(10) Uani 1 1 d . . . . .
H2A H 0.8923 1.2749 0.4658 0.026 Uiso 1 1 calc R U . . .
C3 C 0.7854(3) 1.2790(5) 0.48107(19) 0.0208(10) Uani 1 1 d . . . . .
H3A H 0.7916 1.3437 0.5094 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6431(3) 1.2167(5) 0.46742(18) 0.0194(10) Uani 1 1 d . . . . .
H4A H 0.6499 1.2788 0.4988 0.023 Uiso 1 1 calc R U . . .
H4B H 0.6279 1.1283 0.4785 0.023 Uiso 1 1 calc R U . . .
C5 C 0.5776(3) 1.2674(5) 0.41798(18) 0.0185(10) Uani 1 1 d . . . . .
C6 C 0.5351(3) 1.3791(5) 0.4228(2) 0.0253(11) Uani 1 1 d . . . . .
H6A H 0.5487 1.4282 0.4564 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4718(3) 1.4190(5) 0.3775(2) 0.0276(11) Uani 1 1 d . . . . .
H7A H 0.4411 1.4953 0.3798 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4546(3) 1.3459(5) 0.3294(2) 0.0274(11) Uani 1 1 d . . . . .
H8A H 0.4114 1.3704 0.2981 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5009(3) 1.2362(5) 0.3272(2) 0.0216(10) Uani 1 1 d . . . . .
H9A H 0.4893 1.1874 0.2936 0.026 Uiso 1 1 calc R U . . .
C10 C 0.8401(3) 1.0897(5) 0.37927(19) 0.0194(10) Uani 1 1 d . . . . .
C11 C 0.8228(3) 1.1503(5) 0.3275(2) 0.0230(10) Uani 1 1 d . . . . .
C12 C 0.8558(3) 1.0930(6) 0.2895(2) 0.0294(12) Uani 1 1 d . . . . .
H12A H 0.8443 1.1320 0.2538 0.035 Uiso 1 1 calc R U . . .
C13 C 0.9040(3) 0.9829(6) 0.3018(2) 0.0325(13) Uani 1 1 d . . . . .
C14 C 0.9218(3) 0.9282(5) 0.3546(2) 0.0313(13) Uani 1 1 d . . . . .
H14A H 0.9560 0.8529 0.3638 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8909(3) 0.9805(5) 0.3947(2) 0.0258(11) Uani 1 1 d . . . . .
C16 C 0.9090(3) 0.9177(6) 0.4505(2) 0.0362(13) Uani 1 1 d . . . . .
H16A H 0.9245 0.9871 0.4790 0.054 Uiso 1 1 calc R U . . .
H16B H 0.9524 0.8537 0.4559 0.054 Uiso 1 1 calc R U . . .
H16C H 0.8618 0.8712 0.4532 0.054 Uiso 1 1 calc R U . . .
C17 C 0.7713(3) 1.2713(5) 0.3117(2) 0.0294(12) Uani 1 1 d . . . . .
H17A H 0.7550 1.3005 0.3433 0.044 Uiso 1 1 calc R U . . .
H17B H 0.7243 1.2496 0.2806 0.044 Uiso 1 1 calc R U . . .
H17C H 0.8010 1.3432 0.3010 0.044 Uiso 1 1 calc R U . . .
C18 C 0.9365(3) 0.9229(7) 0.2594(3) 0.0452(16) Uani 1 1 d . . . . .
H18A H 0.8977 0.9326 0.2226 0.068 Uiso 1 1 calc R U . . .
H18B H 0.9476 0.8279 0.2676 0.068 Uiso 1 1 calc R U . . .
H18C H 0.9856 0.9689 0.2604 0.068 Uiso 1 1 calc R U . . .
C19 C 0.5631(3) 0.8940(5) 0.40234(18) 0.0173(9) Uani 1 1 d . . . . .
C20 C 0.4708(3) 0.7710(5) 0.42537(19) 0.0217(10) Uani 1 1 d . . . . .
H20A H 0.4207 0.7368 0.4250 0.026 Uiso 1 1 calc R U . . .
C21 C 0.5418(3) 0.7338(5) 0.45970(19) 0.0211(10) Uani 1 1 d . . . . .
H21A H 0.5521 0.6684 0.4881 0.025 Uiso 1 1 calc R U . . .
C22 C 0.6830(3) 0.7984(5) 0.46938(18) 0.0190(10) Uani 1 1 d . . . . .
H22A H 0.6953 0.7375 0.5016 0.023 Uiso 1 1 calc R U . . .
H22B H 0.7058 0.8871 0.4826 0.023 Uiso 1 1 calc R U . . .
C23 C 0.7202(3) 0.7452(5) 0.42787(19) 0.0187(10) Uani 1 1 d . . . . .
C24 C 0.7644(3) 0.6297(5) 0.4384(2) 0.0277(11) Uani 1 1 d . . . . .
H24A H 0.7701 0.5802 0.4713 0.033 Uiso 1 1 calc R U . . .
C25 C 0.8006(3) 0.5864(6) 0.4003(2) 0.0331(13) Uani 1 1 d . . . . .
H25A H 0.8319 0.5075 0.4070 0.040 Uiso 1 1 calc R U . . .
C26 C 0.7904(3) 0.6596(5) 0.3526(2) 0.0297(12) Uani 1 1 d . . . . .
H26A H 0.8143 0.6322 0.3258 0.036 Uiso 1 1 calc R U . . .
C27 C 0.7447(3) 0.7736(5) 0.3449(2) 0.0236(11) Uani 1 1 d . . . . .
H27A H 0.7375 0.8238 0.3120 0.028 Uiso 1 1 calc R U . . .
C28 C 0.4227(3) 0.9310(5) 0.34647(19) 0.0180(10) Uani 1 1 d . . . . .
C29 C 0.4075(3) 0.8814(5) 0.29265(19) 0.0204(10) Uani 1 1 d . . . . .
C30 C 0.3471(3) 0.9420(5) 0.2507(2) 0.0231(11) Uani 1 1 d . . . . .
H30A H 0.3353 0.9100 0.2139 0.028 Uiso 1 1 calc R U . . .
C31 C 0.3040(3) 1.0479(5) 0.2615(2) 0.0247(11) Uani 1 1 d . . . . .
C32 C 0.3212(3) 1.0929(5) 0.3154(2) 0.0229(11) Uani 1 1 d . . . . .
H32A H 0.2914 1.1651 0.3229 0.028 Uiso 1 1 calc R U . . .
C33 C 0.3803(3) 1.0367(5) 0.3587(2) 0.0205(10) Uani 1 1 d . . . . .
C34 C 0.3987(3) 1.0895(5) 0.4173(2) 0.0274(11) Uani 1 1 d . . . . .
H34A H 0.3775 1.1802 0.4162 0.041 Uiso 1 1 calc R U . . .
H34B H 0.4562 1.0910 0.4351 0.041 Uiso 1 1 calc R U . . .
H34C H 0.3742 1.0312 0.4383 0.041 Uiso 1 1 calc R U . . .
C35 C 0.4540(3) 0.7658(5) 0.2806(2) 0.0263(11) Uani 1 1 d . . . . .
H35A H 0.4276 0.7324 0.2431 0.039 Uiso 1 1 calc R U . . .
H35B H 0.4570 0.6942 0.3074 0.039 Uiso 1 1 calc R U . . .
H35C H 0.5076 0.7957 0.2834 0.039 Uiso 1 1 calc R U . . .
C36 C 0.2372(3) 1.1102(6) 0.2155(2) 0.0372(14) Uani 1 1 d . . . . .
H36A H 0.2404 1.2078 0.2188 0.056 Uiso 1 1 calc R U . . .
H36B H 0.1862 1.0797 0.2183 0.056 Uiso 1 1 calc R U . . .
H36C H 0.2419 1.0835 0.1796 0.056 Uiso 1 1 calc R U . . .
C37 C 0.1830(9) 1.0606(14) 0.4083(6) 0.050(3) Uiso 0.5 1 d D U P A 1
H37A H 0.2152 1.1393 0.4055 0.060 Uiso 0.5 1 calc R U P A 1
H37B H 0.1501 1.0842 0.4320 0.060 Uiso 0.5 1 calc R U P A 1
C38 C 0.1312(14) 1.0190(17) 0.3518(7) 0.047(7) Uiso 0.5 1 d D U P A 1
H38A H 0.1487 1.0617 0.3225 0.056 Uiso 0.5 1 calc R U P A 1
H38B H 0.0752 1.0428 0.3462 0.056 Uiso 0.5 1 calc R U P A 1
C39 C 0.1418(8) 0.8679(13) 0.3516(6) 0.045(3) Uiso 0.5 1 d D U P A 1
H39A H 0.1005 0.8208 0.3631 0.054 Uiso 0.5 1 calc R U P A 1
H39B H 0.1414 0.8350 0.3148 0.054 Uiso 0.5 1 calc R U P A 1
C40 C 0.2218(11) 0.853(2) 0.3937(9) 0.061(8) Uiso 0.5 1 d D U P A 1
H40A H 0.2257 0.7648 0.4119 0.073 Uiso 0.5 1 calc R U P A 1
H40B H 0.2631 0.8581 0.3752 0.073 Uiso 0.5 1 calc R U P A 1
C37A C 0.1585(9) 1.0195(15) 0.4192(5) 0.046(3) Uiso 0.5 1 d D U P A 2
H37C H 0.1659 1.1076 0.4378 0.055 Uiso 0.5 1 calc R U P A 2
H37D H 0.1198 0.9670 0.4313 0.055 Uiso 0.5 1 calc R U P A 2
C38A C 0.1315(12) 1.0356(17) 0.3579(6) 0.039(6) Uiso 0.5 1 d D U P A 2
H38C H 0.1578 1.1125 0.3465 0.046 Uiso 0.5 1 calc R U P A 2
H38D H 0.0734 1.0478 0.3434 0.046 Uiso 0.5 1 calc R U P A 2
C39A C 0.1567(8) 0.9033(14) 0.3381(5) 0.041(3) Uiso 0.5 1 d D U P A 2
H39C H 0.1124 0.8386 0.3288 0.050 Uiso 0.5 1 calc R U P A 2
H39D H 0.1734 0.9178 0.3049 0.050 Uiso 0.5 1 calc R U P A 2
C40A C 0.2245(8) 0.8526(15) 0.3851(6) 0.027(4) Uiso 0.5 1 d D U P A 2
H40C H 0.2130 0.7619 0.3960 0.032 Uiso 0.5 1 calc R U P A 2
H40D H 0.2735 0.8493 0.3745 0.032 Uiso 0.5 1 calc R U P A 2
O2 O 0.5240(5) 0.9073(9) 0.0776(4) 0.036(2) Uiso 0.5 1 d D U P B 1
C41 C 0.4678(7) 0.8049(12) 0.0864(6) 0.043(3) Uiso 0.5 1 d D U P B 1
H41A H 0.4264 0.7829 0.0512 0.051 Uiso 0.5 1 calc R U P B 1
H41B H 0.4961 0.7220 0.1025 0.051 Uiso 0.5 1 calc R U P B 1
C42 C 0.4334(10) 0.8702(16) 0.1253(7) 0.055(5) Uiso 0.5 1 d D U P B 1
H42A H 0.4635 0.8460 0.1638 0.066 Uiso 0.5 1 calc R U P B 1
H42B H 0.3776 0.8419 0.1179 0.066 Uiso 0.5 1 calc R U P B 1
C43 C 0.4376(10) 1.0159(14) 0.1169(7) 0.050(4) Uiso 0.5 1 d D U P B 1
H43A H 0.4628 1.0615 0.1526 0.061 Uiso 0.5 1 calc R U P B 1
H43B H 0.3839 1.0535 0.1000 0.061 Uiso 0.5 1 calc R U P B 1
C44 C 0.4863(13) 1.0331(16) 0.0789(10) 0.088(7) Uiso 0.5 1 d D U P B 1
H44A H 0.4523 1.0581 0.0414 0.106 Uiso 0.5 1 calc R U P B 1
H44B H 0.5265 1.1040 0.0929 0.106 Uiso 0.5 1 calc R U P B 1
O2A O 0.5046(6) 0.8859(10) 0.0612(4) 0.043(3) Uiso 0.5 1 d D U P C 2
C41A C 0.4995(9) 0.8289(14) 0.1146(6) 0.057(4) Uiso 0.5 1 d D U P C 2
H41C H 0.4808 0.7352 0.1093 0.068 Uiso 0.5 1 calc R U P C 2
H41D H 0.5520 0.8310 0.1433 0.068 Uiso 0.5 1 calc R U P C 2
C42A C 0.4424(9) 0.9134(15) 0.1312(6) 0.049(4) Uiso 0.5 1 d D U P C 2
H42C H 0.4549 0.9151 0.1719 0.059 Uiso 0.5 1 calc R U P C 2
H42D H 0.3876 0.8806 0.1144 0.059 Uiso 0.5 1 calc R U P C 2
C43A C 0.4526(11) 1.0491(15) 0.1094(6) 0.056(5) Uiso 0.5 1 d D U P C 2
H43C H 0.4038 1.1033 0.1020 0.067 Uiso 0.5 1 calc R U P C 2
H43D H 0.4975 1.0978 0.1353 0.067 Uiso 0.5 1 calc R U P C 2
C44A C 0.4694(7) 1.0146(11) 0.0568(5) 0.032(3) Uiso 0.5 1 d D U P C 2
H44C H 0.4195 1.0157 0.0255 0.038 Uiso 0.5 1 calc R U P C 2
H44D H 0.5056 1.0819 0.0494 0.038 Uiso 0.5 1 calc R U P C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C1 2.110(5) . ?
Fe1 C19 2.120(5) . ?
Fe1 N1 2.292(4) . ?
Fe1 N4 2.312(4) . ?
Fe1 Br1 2.4114(9) . ?
O1 C40 1.33(2) . ?
O1 C37 1.435(15) . ?
O1 C37A 1.449(14) . ?
O1 C40A 1.492(16) . ?
N1 C9 1.346(6) . ?
N1 C5 1.348(6) . ?
N2 C1 1.349(6) . ?
N2 C3 1.384(6) . ?
N2 C4 1.462(6) . ?
N3 C1 1.360(6) . ?
N3 C2 1.389(6) . ?
N3 C10 1.441(6) . ?
N4 C27 1.340(6) . ?
N4 C23 1.348(6) . ?
N5 C19 1.353(6) . ?
N5 C21 1.381(6) . ?
N5 C22 1.467(6) . ?
N6 C19 1.365(6) . ?
N6 C20 1.387(6) . ?
N6 C28 1.440(6) . ?
C2 C3 1.343(7) . ?
C4 C5 1.510(6) . ?
C5 C6 1.376(7) . ?
C6 C7 1.394(7) . ?
C7 C8 1.375(8) . ?
C8 C9 1.383(7) . ?
C10 C11 1.393(7) . ?
C10 C15 1.394(7) . ?
C11 C12 1.401(7) . ?
C11 C17 1.495(7) . ?
C12 C13 1.370(8) . ?
C13 C14 1.394(8) . ?
C13 C18 1.498(8) . ?
C14 C15 1.401(8) . ?
C15 C16 1.493(8) . ?
C20 C21 1.344(7) . ?
C22 C23 1.507(6) . ?
C23 C24 1.377(7) . ?
C24 C25 1.389(7) . ?
C25 C26 1.380(8) . ?
C26 C27 1.378(7) . ?
C28 C33 1.390(7) . ?
C28 C29 1.401(6) . ?
C29 C30 1.393(7) . ?
C29 C35 1.507(7) . ?
C30 C31 1.384(8) . ?
C31 C32 1.383(7) . ?
C31 C36 1.517(7) . ?
C32 C33 1.382(7) . ?
C33 C34 1.516(7) . ?
C37 C38 1.504(14) . ?
C38 C39 1.523(16) . ?
C39 C40 1.495(14) . ?
C37A C38A 1.489(14) . ?
C38A C39A 1.532(15) . ?
C39A C40A 1.495(12) . ?
O2 C44 1.431(15) . ?
O2 C41 1.495(12) . ?
C41 C42 1.469(14) . ?
C42 C43 1.479(18) . ?
C43 C44 1.495(15) . ?
O2A C44A 1.420(12) . ?
O2A C41A 1.502(13) . ?
C41A C42A 1.479(14) . ?
C42A C43A 1.499(19) . ?
C43A C44A 1.498(14) . ?

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
C1 Fe1 C19 118.95(17) . . ?
C1 Fe1 N1 83.26(15) . . ?
C19 Fe1 N1 90.11(15) . . ?
C1 Fe1 N4 91.05(15) . . ?
C19 Fe1 N4 82.36(15) . . ?
N1 Fe1 N4 166.95(13) . . ?
C1 Fe1 Br1 119.07(12) . . ?
C19 Fe1 Br1 121.97(12) . . ?
N1 Fe1 Br1 96.83(10) . . ?
N4 Fe1 Br1 96.20(10) . . ?
C40 O1 C37 109.4(9) . . ?
C37A O1 C40A 106.4(7) . . ?
C9 N1 C5 117.8(4) . . ?
C9 N1 Fe1 120.8(3) . . ?
C5 N1 Fe1 121.3(3) . . ?
C1 N2 C3 112.3(4) . . ?
C1 N2 C4 123.0(4) . . ?
C3 N2 C4 124.6(4) . . ?
C1 N3 C2 111.3(4) . . ?
C1 N3 C10 123.9(4) . . ?
C2 N3 C10 124.3(4) . . ?
C27 N4 C23 117.8(4) . . ?
C27 N4 Fe1 121.6(3) . . ?
C23 N4 Fe1 120.6(3) . . ?
C19 N5 C21 112.8(4) . . ?
C19 N5 C22 122.1(4) . . ?
C21 N5 C22 125.0(4) . . ?
C19 N6 C20 111.1(4) . . ?
C19 N6 C28 124.5(4) . . ?
C20 N6 C28 124.4(4) . . ?
N2 C1 N3 103.5(4) . . ?
N2 C1 Fe1 121.0(3) . . ?
N3 C1 Fe1 135.1(3) . . ?
C3 C2 N3 106.8(4) . . ?
C2 C3 N2 106.1(4) . . ?
N2 C4 C5 112.0(3) . . ?
N1 C5 C6 122.8(4) . . ?
N1 C5 C4 117.1(4) . . ?
C6 C5 C4 120.1(4) . . ?
C5 C6 C7 118.9(5) . . ?
C8 C7 C6 118.6(5) . . ?
C7 C8 C9 119.3(5) . . ?
N1 C9 C8 122.5(5) . . ?
C11 C10 C15 122.6(4) . . ?
C11 C10 N3 118.0(4) . . ?
C15 C10 N3 119.3(4) . . ?
C10 C11 C12 117.2(5) . . ?
C10 C11 C17 122.9(4) . . ?
C12 C11 C17 119.9(5) . . ?
C13 C12 C11 122.6(5) . . ?
C12 C13 C14 118.2(5) . . ?
C12 C13 C18 120.9(6) . . ?
C14 C13 C18 121.0(5) . . ?
C13 C14 C15 122.2(5) . . ?
C10 C15 C14 117.1(5) . . ?
C10 C15 C16 121.7(5) . . ?
C14 C15 C16 121.2(5) . . ?
N5 C19 N6 103.2(4) . . ?
N5 C19 Fe1 121.1(3) . . ?
N6 C19 Fe1 135.4(3) . . ?
C21 C20 N6 107.2(4) . . ?
C20 C21 N5 105.7(4) . . ?
N5 C22 C23 111.2(4) . . ?
N4 C23 C24 122.2(4) . . ?
N4 C23 C22 117.1(4) . . ?
C24 C23 C22 120.6(4) . . ?
C23 C24 C25 119.2(5) . . ?
C26 C25 C24 119.0(5) . . ?
C27 C26 C25 118.3(5) . . ?
N4 C27 C26 123.5(5) . . ?
C33 C28 C29 122.4(4) . . ?
C33 C28 N6 119.2(4) . . ?
C29 C28 N6 118.3(4) . . ?
C30 C29 C28 117.4(4) . . ?
C30 C29 C35 121.2(4) . . ?
C28 C29 C35 121.3(4) . . ?
C31 C30 C29 121.5(4) . . ?
C32 C31 C30 118.7(5) . . ?
C32 C31 C36 120.6(5) . . ?
C30 C31 C36 120.6(5) . . ?
C33 C32 C31 122.4(5) . . ?
C32 C33 C28 117.4(4) . . ?
C32 C33 C34 121.2(4) . . ?
C28 C33 C34 121.3(4) . . ?
O1 C37 C38 107.0(10) . . ?
C37 C38 C39 103.8(11) . . ?
C40 C39 C38 100.8(11) . . ?
O1 C40 C39 110.0(12) . . ?
O1 C37A C38A 104.5(10) . . ?
C37A C38A C39A 102.7(10) . . ?
C40A C39A C38A 106.0(9) . . ?
O1 C40A C39A 105.7(9) . . ?
C44 O2 C41 105.1(9) . . ?
C42 C41 O2 103.5(10) . . ?
C41 C42 C43 106.9(10) . . ?
C42 C43 C44 105.8(10) . . ?
O2 C44 C43 106.4(11) . . ?
C44A O2A C41A 105.4(9) . . ?
C42A C41A O2A 106.3(10) . . ?
C41A C42A C43A 103.9(10) . . ?
C44A C43A C42A 101.7(10) . . ?
O2A C44A C43A 110.1(9) . . ?

_refine_diff_density_max         0.788
_refine_diff_density_min         -2.401
_refine_diff_density_rms         0.127

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1493391'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H37 Br Fe N4 Si2'
_chemical_formula_weight         573.51

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'
Si Si 0.0817 0.0704 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9454(9)
_cell_length_b                   16.0770(11)
_cell_length_c                   19.4063(19)
_cell_angle_alpha                65.934(4)
_cell_angle_beta                 84.261(6)
_cell_angle_gamma                89.170(4)
_cell_volume                     2817.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    34932
_cell_measurement_theta_min      2.059
_cell_measurement_theta_max      27.603

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    2.057
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5696
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34932
_diffrn_reflns_av_unetI/netI     0.1692
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.059
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             12901
_reflns_number_gt                6521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12901
_refine_ls_number_parameters     595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1795
_refine_ls_R_factor_gt           0.0855
_refine_ls_wR_factor_ref         0.2367
_refine_ls_wR_factor_gt          0.2007
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe -0.48737(11) -0.22838(7) 0.32508(6) 0.0202(3) Uani 1 1 d . . . . .
Fe2 Fe 0.04999(11) 0.27019(7) 0.33210(6) 0.0212(3) Uani 1 1 d . . . . .
Br1 Br -0.51288(9) -0.38051(5) 0.42976(5) 0.0296(2) Uani 1 1 d . . . . .
Br2 Br 0.05852(9) 0.12204(5) 0.44048(5) 0.0305(2) Uani 1 1 d . . . . .
Si1 Si -0.6830(2) -0.28565(14) 0.23666(13) 0.0247(5) Uani 1 1 d . . . . .
Si2 Si -0.5652(2) -0.09344(14) 0.16414(13) 0.0248(5) Uani 1 1 d . . . . .
Si3 Si 0.2569(2) 0.21160(14) 0.23075(13) 0.0256(5) Uani 1 1 d . . . . .
Si4 Si 0.1737(2) 0.40918(14) 0.16892(12) 0.0239(5) Uani 1 1 d . . . . .
N1 N -0.2617(6) -0.1674(4) 0.3875(4) 0.0253(15) Uani 1 1 d . . . . .
N2 N -0.1710(6) -0.1687(4) 0.2832(4) 0.0251(15) Uani 1 1 d . . . . .
N3 N -0.5572(6) -0.1501(4) 0.3879(3) 0.0203(14) Uani 1 1 d . . . . .
N4 N -0.5959(6) -0.1960(4) 0.2404(3) 0.0247(15) Uani 1 1 d . . . . .
N5 N -0.2571(7) 0.3261(5) 0.3011(4) 0.0324(17) Uani 1 1 d . . . . .
N6 N -0.1968(6) 0.3297(4) 0.4019(4) 0.0273(16) Uani 1 1 d . . . . .
N7 N 0.1010(6) 0.3498(4) 0.3933(3) 0.0224(14) Uani 1 1 d . . . . .
N8 N 0.1704(6) 0.3020(4) 0.2391(3) 0.0236(15) Uani 1 1 d . . . . .
C1 C -0.2888(8) -0.1879(5) 0.3287(4) 0.0240(17) Uani 1 1 d . . . . .
C2 C -0.0723(8) -0.1377(6) 0.3128(5) 0.038(2) Uani 1 1 d . . . . .
H2A H 0.0179 -0.1198 0.2907 0.045 Uiso 1 1 calc R U . . .
C3 C -0.1276(8) -0.1375(5) 0.3783(5) 0.0292(19) Uani 1 1 d . . . . .
H3A H -0.0840 -0.1204 0.4121 0.035 Uiso 1 1 calc R U . . .
C4 C -0.3554(8) -0.1886(6) 0.4567(4) 0.031(2) Uani 1 1 d . . . . .
H4A H -0.3112 -0.1704 0.4921 0.038 Uiso 1 1 calc R U . . .
H4B H -0.3726 -0.2553 0.4816 0.038 Uiso 1 1 calc R U . . .
C5 C -0.4909(8) -0.1416(5) 0.4426(4) 0.0228(17) Uani 1 1 d . . . . .
C6 C -0.5447(9) -0.1024(5) 0.4900(5) 0.032(2) Uani 1 1 d . . . . .
H6A H -0.4965 -0.1006 0.5293 0.038 Uiso 1 1 calc R U . . .
C7 C -0.6710(9) -0.0657(5) 0.4784(5) 0.035(2) Uani 1 1 d . . . . .
H7A H -0.7110 -0.0374 0.5096 0.042 Uiso 1 1 calc R U . . .
C8 C -0.7398(9) -0.0704(5) 0.4209(5) 0.032(2) Uani 1 1 d . . . . .
H8A H -0.8256 -0.0437 0.4114 0.039 Uiso 1 1 calc R U . . .
C9 C -0.6811(8) -0.1142(5) 0.3781(4) 0.0286(19) Uani 1 1 d . . . . .
H9A H -0.7297 -0.1194 0.3402 0.034 Uiso 1 1 calc R U . . .
C10 C -0.1507(7) -0.1812(5) 0.2133(5) 0.0245(18) Uani 1 1 d . . . . .
C11 C -0.1226(8) -0.1057(5) 0.1456(5) 0.0254(18) Uani 1 1 d . . . . .
C12 C -0.1036(8) -0.1199(6) 0.0784(5) 0.034(2) Uani 1 1 d . . . . .
H12A H -0.0819 -0.0691 0.0314 0.040 Uiso 1 1 calc R U . . .
C13 C -0.1157(8) -0.2069(6) 0.0788(5) 0.033(2) Uani 1 1 d . . . . .
C14 C -0.1422(8) -0.2799(6) 0.1484(5) 0.034(2) Uani 1 1 d . . . . .
H14A H -0.1493 -0.3393 0.1494 0.041 Uiso 1 1 calc R U . . .
C15 C -0.1592(8) -0.2703(5) 0.2177(5) 0.0260(18) Uani 1 1 d . . . . .
C16 C -0.1820(8) -0.3534(5) 0.2903(5) 0.033(2) Uani 1 1 d . . . . .
H16A H -0.1363 -0.3448 0.3295 0.049 Uiso 1 1 calc R U . . .
H16B H -0.1456 -0.4063 0.2827 0.049 Uiso 1 1 calc R U . . .
H16C H -0.2792 -0.3634 0.3063 0.049 Uiso 1 1 calc R U . . .
C17 C -0.1105(8) -0.0089(5) 0.1392(5) 0.034(2) Uani 1 1 d . . . . .
H17A H -0.1532 -0.0056 0.1857 0.051 Uiso 1 1 calc R U . . .
H17B H -0.1557 0.0321 0.0958 0.051 Uiso 1 1 calc R U . . .
H17C H -0.0148 0.0095 0.1319 0.051 Uiso 1 1 calc R U . . .
C18 C -0.1005(10) -0.2211(7) 0.0063(5) 0.052(3) Uani 1 1 d . . . . .
H18A H -0.0771 -0.2844 0.0175 0.077 Uiso 1 1 calc R U . . .
H18B H -0.0286 -0.1801 -0.0289 0.077 Uiso 1 1 calc R U . . .
H18C H -0.1858 -0.2080 -0.0169 0.077 Uiso 1 1 calc R U . . .
C19 C -0.4579(8) -0.1065(6) 0.0828(4) 0.038(2) Uani 1 1 d . . . . .
H19A H -0.5146 -0.1302 0.0560 0.058 Uiso 1 1 calc R U . . .
H19B H -0.3856 -0.1490 0.1028 0.058 Uiso 1 1 calc R U . . .
H19C H -0.4182 -0.0470 0.0476 0.058 Uiso 1 1 calc R U . . .
C20 C -0.7220(8) -0.0325(6) 0.1266(5) 0.037(2) Uani 1 1 d . . . . .
H20A H -0.7887 -0.0382 0.1691 0.056 Uiso 1 1 calc R U . . .
H20B H -0.7596 -0.0596 0.0954 0.056 Uiso 1 1 calc R U . . .
H20C H -0.6994 0.0321 0.0956 0.056 Uiso 1 1 calc R U . . .
C21 C -0.4727(9) -0.0141(5) 0.1930(5) 0.036(2) Uani 1 1 d . . . . .
H21A H -0.5335 0.0035 0.2274 0.054 Uiso 1 1 calc R U . . .
H21B H -0.4415 0.0404 0.1478 0.054 Uiso 1 1 calc R U . . .
H21C H -0.3947 -0.0447 0.2188 0.054 Uiso 1 1 calc R U . . .
C22 C -0.7747(10) -0.2544(6) 0.1507(5) 0.047(3) Uani 1 1 d . . . . .
H22A H -0.8491 -0.2146 0.1527 0.070 Uiso 1 1 calc R U . . .
H22B H -0.8109 -0.3098 0.1489 0.070 Uiso 1 1 calc R U . . .
H22C H -0.7122 -0.2224 0.1052 0.070 Uiso 1 1 calc R U . . .
C23 C -0.5656(8) -0.3777(5) 0.2357(5) 0.035(2) Uani 1 1 d . . . . .
H23A H -0.5218 -0.4021 0.2828 0.053 Uiso 1 1 calc R U . . .
H23B H -0.4966 -0.3524 0.1922 0.053 Uiso 1 1 calc R U . . .
H23C H -0.6171 -0.4267 0.2316 0.053 Uiso 1 1 calc R U . . .
C24 C -0.8143(8) -0.3339(5) 0.3201(5) 0.031(2) Uani 1 1 d . . . . .
H24A H -0.8794 -0.2870 0.3186 0.047 Uiso 1 1 calc R U . . .
H24B H -0.7707 -0.3542 0.3671 0.047 Uiso 1 1 calc R U . . .
H24C H -0.8616 -0.3859 0.3181 0.047 Uiso 1 1 calc R U . . .
C25 C -0.1502(8) 0.3070(5) 0.3431(4) 0.0239(17) Uani 1 1 d . . . . .
C26 C -0.3642(8) 0.3562(6) 0.3338(5) 0.040(2) Uani 1 1 d . . . . .
H26A H -0.4494 0.3725 0.3146 0.048 Uiso 1 1 calc R U . . .
C27 C -0.3282(8) 0.3587(6) 0.3974(5) 0.039(2) Uani 1 1 d . . . . .
H27A H -0.3816 0.3766 0.4321 0.047 Uiso 1 1 calc R U . . .
C28 C -0.1210(8) 0.3109(6) 0.4673(4) 0.031(2) Uani 1 1 d . . . . .
H28A H -0.1102 0.2443 0.4928 0.037 Uiso 1 1 calc R U . . .
H28B H -0.1754 0.3300 0.5037 0.037 Uiso 1 1 calc R U . . .
C29 C 0.0180(8) 0.3572(5) 0.4496(4) 0.0217(17) Uani 1 1 d . . . . .
C30 C 0.0610(8) 0.3971(5) 0.4948(5) 0.0289(19) Uani 1 1 d . . . . .
H30A H 0.0020 0.3994 0.5356 0.035 Uiso 1 1 calc R U . . .
C31 C 0.1916(8) 0.4336(5) 0.4799(5) 0.0300(19) Uani 1 1 d . . . . .
H31A H 0.2227 0.4614 0.5104 0.036 Uiso 1 1 calc R U . . .
C32 C 0.2759(8) 0.4296(5) 0.4209(4) 0.0253(18) Uani 1 1 d . . . . .
H32A H 0.3650 0.4554 0.4092 0.030 Uiso 1 1 calc R U . . .
C33 C 0.2273(8) 0.3867(5) 0.3791(4) 0.0269(18) Uani 1 1 d . . . . .
H33A H 0.2854 0.3830 0.3386 0.032 Uiso 1 1 calc R U . . .
C34 C -0.2603(7) 0.3128(5) 0.2318(4) 0.0245(18) Uani 1 1 d . . . . .
C35 C -0.2573(8) 0.2230(5) 0.2356(4) 0.0248(18) Uani 1 1 d . . . . .
C36 C -0.2624(8) 0.2125(6) 0.1690(5) 0.0295(19) Uani 1 1 d . . . . .
H36A H -0.2564 0.1530 0.1700 0.035 Uiso 1 1 calc R U . . .
C37 C -0.2758(8) 0.2845(6) 0.1014(5) 0.033(2) Uani 1 1 d . . . . .
C38 C -0.2813(8) 0.3723(6) 0.0989(5) 0.036(2) Uani 1 1 d . . . . .
H38A H -0.2906 0.4223 0.0520 0.044 Uiso 1 1 calc R U . . .
C39 C -0.2734(8) 0.3889(5) 0.1644(5) 0.031(2) Uani 1 1 d . . . . .
C40 C -0.2489(9) 0.1417(5) 0.3093(5) 0.035(2) Uani 1 1 d . . . . .
H40A H -0.2694 0.0860 0.3028 0.053 Uiso 1 1 calc R U . . .
H40B H -0.3144 0.1470 0.3485 0.053 Uiso 1 1 calc R U . . .
H40C H -0.1575 0.1390 0.3247 0.053 Uiso 1 1 calc R U . . .
C41 C -0.2785(9) 0.4841(5) 0.1584(6) 0.042(2) Uani 1 1 d . . . . .
H41A H -0.2556 0.4855 0.2059 0.063 Uiso 1 1 calc R U . . .
H41B H -0.3698 0.5069 0.1489 0.063 Uiso 1 1 calc R U . . .
H41C H -0.2136 0.5228 0.1164 0.063 Uiso 1 1 calc R U . . .
C42 C -0.2875(10) 0.2697(7) 0.0298(5) 0.048(3) Uani 1 1 d . . . . .
H42A H -0.2612 0.2076 0.0381 0.071 Uiso 1 1 calc R U . . .
H42B H -0.2277 0.3136 -0.0121 0.071 Uiso 1 1 calc R U . . .
H42C H -0.3811 0.2784 0.0172 0.071 Uiso 1 1 calc R U . . .
C43 C 0.0785(8) 0.4890(5) 0.2029(5) 0.032(2) Uani 1 1 d . . . . .
H43A H -0.0090 0.4607 0.2295 0.049 Uiso 1 1 calc R U . . .
H43B H 0.0638 0.5458 0.1594 0.049 Uiso 1 1 calc R U . . .
H43C H 0.1308 0.5022 0.2376 0.049 Uiso 1 1 calc R U . . .
C44 C 0.3497(8) 0.4609(6) 0.1355(5) 0.040(2) Uani 1 1 d . . . . .
H44A H 0.3919 0.4403 0.0975 0.060 Uiso 1 1 calc R U . . .
H44B H 0.4036 0.4418 0.1787 0.060 Uiso 1 1 calc R U . . .
H44C H 0.3451 0.5275 0.1128 0.060 Uiso 1 1 calc R U . . .
C45 C 0.0942(9) 0.4147(6) 0.0836(5) 0.039(2) Uani 1 1 d . . . . .
H45A H 0.0088 0.3792 0.0999 0.058 Uiso 1 1 calc R U . . .
H45B H 0.1555 0.3896 0.0547 0.058 Uiso 1 1 calc R U . . .
H45C H 0.0767 0.4783 0.0515 0.058 Uiso 1 1 calc R U . . .
C46 C 0.3802(8) 0.1674(5) 0.3024(5) 0.034(2) Uani 1 1 d . . . . .
H46A H 0.3340 0.1538 0.3530 0.050 Uiso 1 1 calc R U . . .
H46B H 0.4523 0.2135 0.2910 0.050 Uiso 1 1 calc R U . . .
H46C H 0.4193 0.1118 0.3011 0.050 Uiso 1 1 calc R U . . .
C47 C 0.1359(9) 0.1165(5) 0.2436(5) 0.036(2) Uani 1 1 d . . . . .
H47A H 0.0871 0.0941 0.2945 0.055 Uiso 1 1 calc R U . . .
H47B H 0.1862 0.0667 0.2374 0.055 Uiso 1 1 calc R U . . .
H47C H 0.0711 0.1390 0.2056 0.055 Uiso 1 1 calc R U . . .
C48 C 0.3574(9) 0.2403(6) 0.1361(5) 0.044(2) Uani 1 1 d . . . . .
H48A H 0.4249 0.2885 0.1270 0.067 Uiso 1 1 calc R U . . .
H48B H 0.2965 0.2616 0.0960 0.067 Uiso 1 1 calc R U . . .
H48C H 0.4031 0.1859 0.1360 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N4 1.943(6) . ?
Fe1 C1 2.105(8) . ?
Fe1 N3 2.146(6) . ?
Fe1 Br1 2.4567(13) . ?
Fe2 N8 1.945(6) . ?
Fe2 C25 2.084(8) . ?
Fe2 N7 2.166(6) . ?
Fe2 Br2 2.4592(13) . ?
Si1 N4 1.722(6) . ?
Si1 C22 1.864(9) . ?
Si1 C24 1.874(8) . ?
Si1 C23 1.877(8) . ?
Si2 N4 1.714(6) . ?
Si2 C21 1.872(8) . ?
Si2 C20 1.877(8) . ?
Si2 C19 1.898(8) . ?
Si3 N8 1.734(6) . ?
Si3 C46 1.858(9) . ?
Si3 C47 1.879(8) . ?
Si3 C48 1.882(9) . ?
Si4 N8 1.704(6) . ?
Si4 C43 1.873(8) . ?
Si4 C45 1.875(8) . ?
Si4 C44 1.885(8) . ?
N1 C1 1.363(9) . ?
N1 C3 1.393(10) . ?
N1 C4 1.474(10) . ?
N2 C1 1.352(9) . ?
N2 C2 1.378(10) . ?
N2 C10 1.445(10) . ?
N3 C9 1.351(10) . ?
N3 C5 1.358(9) . ?
N5 C25 1.359(10) . ?
N5 C26 1.368(10) . ?
N5 C34 1.450(9) . ?
N6 C25 1.371(9) . ?
N6 C27 1.379(10) . ?
N6 C28 1.464(10) . ?
N7 C29 1.345(9) . ?
N7 C33 1.351(9) . ?
C2 C3 1.335(11) . ?
C4 C5 1.529(11) . ?
C5 C6 1.376(10) . ?
C6 C7 1.379(12) . ?
C7 C8 1.393(12) . ?
C8 C9 1.377(11) . ?
C10 C11 1.384(10) . ?
C10 C15 1.404(10) . ?
C11 C12 1.407(11) . ?
C11 C17 1.515(10) . ?
C12 C13 1.402(11) . ?
C13 C14 1.384(12) . ?
C13 C18 1.509(11) . ?
C14 C15 1.408(11) . ?
C15 C16 1.494(11) . ?
C26 C27 1.334(12) . ?
C28 C29 1.520(10) . ?
C29 C30 1.380(10) . ?
C30 C31 1.388(11) . ?
C31 C32 1.373(11) . ?
C32 C33 1.381(10) . ?
C34 C39 1.395(11) . ?
C34 C35 1.415(10) . ?
C35 C36 1.377(11) . ?
C35 C40 1.503(11) . ?
C36 C37 1.367(11) . ?
C37 C38 1.394(12) . ?
C37 C42 1.517(11) . ?
C38 C39 1.409(11) . ?
C39 C41 1.488(11) . ?

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 C1 130.5(3) . . ?
N4 Fe1 N3 107.1(3) . . ?
C1 Fe1 N3 88.0(3) . . ?
N4 Fe1 Br1 120.29(18) . . ?
C1 Fe1 Br1 102.9(2) . . ?
N3 Fe1 Br1 98.18(16) . . ?
N8 Fe2 C25 127.7(3) . . ?
N8 Fe2 N7 110.8(2) . . ?
C25 Fe2 N7 88.2(3) . . ?
N8 Fe2 Br2 121.86(19) . . ?
C25 Fe2 Br2 103.3(2) . . ?
N7 Fe2 Br2 94.98(16) . . ?
N4 Si1 C22 114.2(4) . . ?
N4 Si1 C24 110.1(3) . . ?
C22 Si1 C24 106.1(4) . . ?
N4 Si1 C23 111.1(3) . . ?
C22 Si1 C23 105.6(4) . . ?
C24 Si1 C23 109.5(4) . . ?
N4 Si2 C21 109.5(3) . . ?
N4 Si2 C20 114.1(3) . . ?
C21 Si2 C20 105.2(4) . . ?
N4 Si2 C19 111.7(4) . . ?
C21 Si2 C19 108.2(4) . . ?
C20 Si2 C19 107.9(4) . . ?
N8 Si3 C46 110.9(3) . . ?
N8 Si3 C47 110.6(4) . . ?
C46 Si3 C47 109.0(4) . . ?
N8 Si3 C48 114.5(4) . . ?
C46 Si3 C48 105.8(4) . . ?
C47 Si3 C48 105.7(4) . . ?
N8 Si4 C43 110.9(3) . . ?
N8 Si4 C45 113.1(4) . . ?
C43 Si4 C45 106.2(4) . . ?
N8 Si4 C44 113.1(4) . . ?
C43 Si4 C44 105.4(4) . . ?
C45 Si4 C44 107.6(4) . . ?
C1 N1 C3 110.6(6) . . ?
C1 N1 C4 123.7(6) . . ?
C3 N1 C4 124.9(6) . . ?
C1 N2 C2 111.5(7) . . ?
C1 N2 C10 124.0(6) . . ?
C2 N2 C10 124.4(7) . . ?
C9 N3 C5 117.1(6) . . ?
C9 N3 Fe1 118.3(5) . . ?
C5 N3 Fe1 124.3(5) . . ?
Si2 N4 Si1 123.1(4) . . ?
Si2 N4 Fe1 119.2(3) . . ?
Si1 N4 Fe1 115.1(3) . . ?
C25 N5 C26 111.8(7) . . ?
C25 N5 C34 124.5(7) . . ?
C26 N5 C34 123.7(7) . . ?
C25 N6 C27 112.5(7) . . ?
C25 N6 C28 122.2(7) . . ?
C27 N6 C28 124.6(7) . . ?
C29 N7 C33 118.3(6) . . ?
C29 N7 Fe2 123.4(5) . . ?
C33 N7 Fe2 118.0(5) . . ?
Si4 N8 Si3 124.1(4) . . ?
Si4 N8 Fe2 120.6(3) . . ?
Si3 N8 Fe2 114.9(3) . . ?
N2 C1 N1 104.1(6) . . ?
N2 C1 Fe1 137.0(6) . . ?
N1 C1 Fe1 118.7(5) . . ?
C3 C2 N2 107.1(7) . . ?
C2 C3 N1 106.7(7) . . ?
N1 C4 C5 114.2(6) . . ?
N3 C5 C6 124.0(7) . . ?
N3 C5 C4 116.3(6) . . ?
C6 C5 C4 119.4(7) . . ?
C5 C6 C7 117.6(8) . . ?
C6 C7 C8 119.8(8) . . ?
C9 C8 C7 118.8(8) . . ?
N3 C9 C8 122.5(8) . . ?
C11 C10 C15 123.0(7) . . ?
C11 C10 N2 119.0(7) . . ?
C15 C10 N2 118.0(7) . . ?
C10 C11 C12 117.7(7) . . ?
C10 C11 C17 124.3(7) . . ?
C12 C11 C17 118.0(7) . . ?
C13 C12 C11 121.9(8) . . ?
C14 C13 C12 117.7(8) . . ?
C14 C13 C18 120.8(8) . . ?
C12 C13 C18 121.5(8) . . ?
C13 C14 C15 123.1(8) . . ?
C10 C15 C14 116.5(7) . . ?
C10 C15 C16 124.0(7) . . ?
C14 C15 C16 119.4(7) . . ?
N5 C25 N6 102.2(6) . . ?
N5 C25 Fe2 137.1(6) . . ?
N6 C25 Fe2 120.2(5) . . ?
C27 C26 N5 108.1(8) . . ?
C26 C27 N6 105.4(7) . . ?
N6 C28 C29 115.6(6) . . ?
N7 C29 C30 121.7(7) . . ?
N7 C29 C28 117.4(6) . . ?
C30 C29 C28 120.6(7) . . ?
C29 C30 C31 119.1(8) . . ?
C32 C31 C30 119.9(7) . . ?
C31 C32 C33 118.0(7) . . ?
N7 C33 C32 122.9(7) . . ?
C39 C34 C35 122.5(7) . . ?
C39 C34 N5 118.6(7) . . ?
C35 C34 N5 118.8(7) . . ?
C36 C35 C34 117.5(7) . . ?
C36 C35 C40 120.8(7) . . ?
C34 C35 C40 121.7(7) . . ?
C37 C36 C35 122.5(8) . . ?
C36 C37 C38 119.2(8) . . ?
C36 C37 C42 120.9(8) . . ?
C38 C37 C42 119.8(8) . . ?
C37 C38 C39 121.7(8) . . ?
C34 C39 C38 116.6(7) . . ?
C34 C39 C41 124.0(8) . . ?
C38 C39 C41 119.4(8) . . ?

_refine_diff_density_max         2.879
_refine_diff_density_min         -1.008
_refine_diff_density_rms         0.209

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1493392'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 Br2 Fe N3'
_chemical_formula_weight         493.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.9641(7)
_cell_length_b                   10.4299(6)
_cell_length_c                   16.3971(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.354(3)
_cell_angle_gamma                90
_cell_volume                     1918.35(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14265
_cell_measurement_theta_min      2.360
_cell_measurement_theta_max      24.999

_exptl_crystal_description       yellow
_exptl_crystal_colour            prism
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    4.956
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14265
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.360
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3379
_reflns_number_gt                2728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+1.6599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3379
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.49387(4) -0.22614(4) 0.33554(3) 0.01907(13) Uani 1 1 d . . . . .
Br1 Br 0.31390(3) -0.14930(3) 0.35219(3) 0.03146(12) Uani 1 1 d . . . . .
Br2 Br 0.48396(3) -0.34559(4) 0.20822(2) 0.03210(12) Uani 1 1 d . . . . .
N1 N 0.6966(2) -0.0900(3) 0.46740(17) 0.0203(6) Uani 1 1 d . . . . .
N2 N 0.6796(2) -0.0044(2) 0.34569(17) 0.0182(6) Uani 1 1 d . . . . .
N3 N 0.5904(2) -0.3505(3) 0.44178(17) 0.0190(6) Uani 1 1 d . . . . .
C1 C 0.6267(3) -0.0906(3) 0.3823(2) 0.0189(7) Uani 1 1 d . . . . .
C2 C 0.7810(3) 0.0478(3) 0.4065(2) 0.0248(8) Uani 1 1 d . . . . .
H2A H 0.8334 0.1088 0.3960 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7905(3) -0.0057(3) 0.4836(2) 0.0243(8) Uani 1 1 d . . . . .
H3A H 0.8502 0.0115 0.5383 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6660(3) -0.1619(3) 0.5338(2) 0.0243(8) Uani 1 1 d . . . . .
H4A H 0.5875 -0.1320 0.5339 0.029 Uiso 1 1 calc R U . . .
H4B H 0.7259 -0.1426 0.5916 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6609(3) -0.3047(3) 0.5199(2) 0.0199(7) Uani 1 1 d . . . . .
C6 C 0.7230(3) -0.3858(4) 0.5875(2) 0.0277(8) Uani 1 1 d . . . . .
H6A H 0.7714 -0.3514 0.6420 0.033 Uiso 1 1 calc R U . . .
C7 C 0.7138(3) -0.5169(3) 0.5750(2) 0.0284(8) Uani 1 1 d . . . . .
H7A H 0.7548 -0.5737 0.6210 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6446(3) -0.5641(3) 0.4953(2) 0.0253(8) Uani 1 1 d . . . . .
H8A H 0.6385 -0.6538 0.4847 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5841(3) -0.4786(3) 0.4307(2) 0.0211(7) Uani 1 1 d . . . . .
H9A H 0.5356 -0.5117 0.3758 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6298(3) 0.0421(3) 0.2573(2) 0.0173(7) Uani 1 1 d . . . . .
C11 C 0.6763(3) -0.0017(3) 0.1959(2) 0.0198(7) Uani 1 1 d . . . . .
C12 C 0.6343(3) 0.0561(3) 0.1140(2) 0.0227(8) Uani 1 1 d . . . . .
H12A H 0.6662 0.0298 0.0711 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5479(3) 0.1503(3) 0.0937(2) 0.0227(8) Uani 1 1 d . . . . .
C14 C 0.5005(3) 0.1874(3) 0.1560(2) 0.0228(8) Uani 1 1 d . . . . .
H14A H 0.4391 0.2502 0.1417 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5410(3) 0.1345(3) 0.2395(2) 0.0184(7) Uani 1 1 d . . . . .
C16 C 0.4873(3) 0.1778(4) 0.3058(2) 0.0299(9) Uani 1 1 d . . . . .
H16A H 0.5512 0.1948 0.3613 0.045 Uiso 1 1 calc R U . . .
H16B H 0.4350 0.1104 0.3139 0.045 Uiso 1 1 calc R U . . .
H16C H 0.4409 0.2562 0.2853 0.045 Uiso 1 1 calc R U . . .
C17 C 0.7681(3) -0.1068(3) 0.2169(2) 0.0265(8) Uani 1 1 d . . . . .
H17A H 0.7422 -0.1779 0.2452 0.040 Uiso 1 1 calc R U . . .
H17B H 0.8446 -0.0737 0.2560 0.040 Uiso 1 1 calc R U . . .
H17C H 0.7773 -0.1375 0.1630 0.040 Uiso 1 1 calc R U . . .
C18 C 0.5067(4) 0.2148(4) 0.0051(2) 0.0358(10) Uani 1 1 d . . . . .
H18A H 0.5447 0.1732 -0.0321 0.054 Uiso 1 1 calc R U . . .
H18B H 0.5290 0.3057 0.0120 0.054 Uiso 1 1 calc R U . . .
H18C H 0.4199 0.2072 -0.0217 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C1 2.065(3) . ?
Fe1 N3 2.157(3) . ?
Fe1 Br2 2.3984(6) . ?
Fe1 Br1 2.4004(6) . ?
N1 C1 1.354(4) . ?
N1 C3 1.377(4) . ?
N1 C4 1.469(4) . ?
N2 C1 1.354(4) . ?
N2 C2 1.386(4) . ?
N2 C10 1.445(4) . ?
N3 C9 1.347(4) . ?
N3 C5 1.352(4) . ?
C2 C3 1.350(5) . ?
C4 C5 1.505(5) . ?
C5 C6 1.386(5) . ?
C6 C7 1.382(5) . ?
C7 C8 1.373(5) . ?
C8 C9 1.381(5) . ?
C10 C11 1.386(5) . ?
C10 C15 1.388(4) . ?
C11 C12 1.396(5) . ?
C11 C17 1.505(5) . ?
C12 C13 1.381(5) . ?
C13 C14 1.386(5) . ?
C13 C18 1.519(5) . ?
C14 C15 1.397(5) . ?
C15 C16 1.512(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Fe1 N3 89.13(11) . . ?
C1 Fe1 Br2 118.52(10) . . ?
N3 Fe1 Br2 103.96(7) . . ?
C1 Fe1 Br1 109.52(10) . . ?
N3 Fe1 Br1 111.01(8) . . ?
Br2 Fe1 Br1 119.85(2) . . ?
C1 N1 C3 111.8(3) . . ?
C1 N1 C4 122.5(3) . . ?
C3 N1 C4 125.4(3) . . ?
C1 N2 C2 111.6(3) . . ?
C1 N2 C10 125.1(3) . . ?
C2 N2 C10 122.8(3) . . ?
C9 N3 C5 117.7(3) . . ?
C9 N3 Fe1 119.9(2) . . ?
C5 N3 Fe1 122.4(2) . . ?
N2 C1 N1 103.7(3) . . ?
N2 C1 Fe1 135.0(2) . . ?
N1 C1 Fe1 120.4(2) . . ?
C3 C2 N2 106.2(3) . . ?
C2 C3 N1 106.6(3) . . ?
N1 C4 C5 113.6(3) . . ?
N3 C5 C6 121.8(3) . . ?
N3 C5 C4 118.1(3) . . ?
C6 C5 C4 120.0(3) . . ?
C7 C6 C5 119.5(3) . . ?
C8 C7 C6 119.1(3) . . ?
C7 C8 C9 118.7(3) . . ?
N3 C9 C8 123.2(3) . . ?
C11 C10 C15 123.1(3) . . ?
C11 C10 N2 119.2(3) . . ?
C15 C10 N2 117.6(3) . . ?
C10 C11 C12 117.1(3) . . ?
C10 C11 C17 121.3(3) . . ?
C12 C11 C17 121.6(3) . . ?
C13 C12 C11 121.9(3) . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 C18 120.9(3) . . ?
C14 C13 C18 120.1(3) . . ?
C13 C14 C15 121.4(3) . . ?
C10 C15 C14 117.4(3) . . ?
C10 C15 C16 122.7(3) . . ?
C14 C15 C16 119.8(3) . . ?

_refine_diff_density_max         1.058
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1493393'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H36 Fe N6'
_chemical_formula_weight         608.56

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   23.229(2)
_cell_length_b                   9.3929(6)
_cell_length_c                   32.344(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.287(6)
_cell_angle_gamma                90
_cell_volume                     6700.7(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    24279
_cell_measurement_theta_min      1.326
_cell_measurement_theta_max      24.998

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             2560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.483
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24279
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.326
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5906
_reflns_number_gt                4336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+5.4037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5906
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe -0.08773(2) 0.24788(4) 0.13451(2) 0.02877(14) Uani 1 1 d . . . . .
N1 N -0.02605(10) 0.3960(2) 0.13404(7) 0.0282(5) Uani 1 1 d . . . . .
N2 N 0.02671(9) 0.1921(2) 0.20745(6) 0.0243(5) Uani 1 1 d . . . . .
N3 N -0.04412(9) 0.0684(2) 0.22046(7) 0.0291(5) Uani 1 1 d . . . . .
N4 N -0.17527(11) 0.2718(3) 0.13071(8) 0.0464(7) Uani 1 1 d . . . . .
N5 N -0.16209(13) 0.0456(3) 0.06812(9) 0.0567(8) Uani 1 1 d . . . . .
N6 N -0.07384(13) 0.0633(3) 0.05763(8) 0.0505(7) Uani 1 1 d . . . . .
C1 C -0.03411(11) 0.1644(3) 0.19161(8) 0.0259(6) Uani 1 1 d . . . . .
C2 C 0.00914(12) 0.0364(3) 0.25293(9) 0.0348(7) Uani 1 1 d . . . . .
H2A H 0.0136 -0.0272 0.2766 0.042 Uiso 1 1 calc R U . . .
C3 C 0.05318(12) 0.1118(3) 0.24477(8) 0.0326(6) Uani 1 1 d . . . . .
H3A H 0.0949 0.1107 0.2614 0.039 Uiso 1 1 calc R U . . .
C4 C 0.05957(12) 0.2873(3) 0.18953(8) 0.0260(6) Uani 1 1 d . . . . .
H4A H 0.1025 0.2856 0.2018 0.031 Uiso 1 1 calc R U . . .
C5 C 0.03591(12) 0.3818(3) 0.15619(8) 0.0259(6) Uani 1 1 d . . . . .
C6 C 0.07716(13) 0.4725(3) 0.14270(9) 0.0347(7) Uani 1 1 d . . . . .
H6A H 0.1196 0.4633 0.1566 0.042 Uiso 1 1 calc R U . . .
C7 C 0.05664(15) 0.5695(3) 0.11092(10) 0.0449(8) Uani 1 1 d . . . . .
H7A H 0.0846 0.6269 0.1023 0.054 Uiso 1 1 calc R U . . .
C8 C -0.00624(15) 0.5864(3) 0.09029(9) 0.0453(8) Uani 1 1 d . . . . .
H8A H -0.0215 0.6564 0.0684 0.054 Uiso 1 1 calc R U . . .
C9 C -0.04405(14) 0.4991(3) 0.10282(9) 0.0390(7) Uani 1 1 d . . . . .
H9A H -0.0864 0.5103 0.0888 0.047 Uiso 1 1 calc R U . . .
C10 C -0.10439(12) 0.0195(3) 0.21792(9) 0.0338(7) Uani 1 1 d . . . . .
C11 C -0.13563(13) 0.0954(3) 0.24127(9) 0.0377(7) Uani 1 1 d . . . . .
C12 C -0.19366(13) 0.0493(4) 0.23798(10) 0.0472(8) Uani 1 1 d . . . . .
H12A H -0.2160 0.0994 0.2534 0.057 Uiso 1 1 calc R U . . .
C13 C -0.22002(13) -0.0668(4) 0.21314(11) 0.0497(9) Uani 1 1 d . . . . .
C14 C -0.18763(14) -0.1382(4) 0.19014(10) 0.0511(9) Uani 1 1 d . . . . .
H14A H -0.2057 -0.2179 0.1728 0.061 Uiso 1 1 calc R U . . .
C15 C -0.12922(13) -0.0965(3) 0.19169(9) 0.0383(7) Uani 1 1 d . . . . .
C16 C -0.09563(15) -0.1710(3) 0.16518(10) 0.0507(8) Uani 1 1 d . . . . .
H16A H -0.0535 -0.1868 0.1831 0.076 Uiso 1 1 calc R U . . .
H16B H -0.0965 -0.1121 0.1400 0.076 Uiso 1 1 calc R U . . .
H16C H -0.1150 -0.2628 0.1551 0.076 Uiso 1 1 calc R U . . .
C17 C -0.10745(15) 0.2225(3) 0.26843(11) 0.0485(8) Uani 1 1 d . . . . .
H17A H -0.1379 0.2702 0.2788 0.073 Uiso 1 1 calc R U . . .
H17B H -0.0925 0.2890 0.2508 0.073 Uiso 1 1 calc R U . . .
H17C H -0.0736 0.1912 0.2935 0.073 Uiso 1 1 calc R U . . .
C18 C -0.28408(15) -0.1132(5) 0.20988(13) 0.0761(13) Uani 1 1 d . . . . .
H18A H -0.2936 -0.2027 0.1936 0.114 Uiso 1 1 calc R U . . .
H18B H -0.3129 -0.0396 0.1948 0.114 Uiso 1 1 calc R U . . .
H18C H -0.2870 -0.1273 0.2392 0.114 Uiso 1 1 calc R U . . .
C19 C -0.10734(14) 0.1143(3) 0.08283(9) 0.0403(7) Uani 1 1 d . . . . .
C20 C -0.1070(2) -0.0388(4) 0.02850(13) 0.0806(14) Uani 1 1 d . . . . .
H20A H -0.0940 -0.0914 0.0080 0.097 Uiso 1 1 calc R U . . .
C21 C -0.1609(2) -0.0479(4) 0.03525(15) 0.0886(15) Uani 1 1 d . . . . .
H21A H -0.1932 -0.1088 0.0199 0.106 Uiso 1 1 calc R U . . .
C22 C -0.21267(16) 0.0698(4) 0.08344(13) 0.0656(12) Uani 1 1 d . . . . .
H22A H -0.2456 0.0053 0.0732 0.079 Uiso 1 1 calc R U . . .
C23 C -0.21965(15) 0.1743(4) 0.11096(12) 0.0563(9) Uani 1 1 d . . . . .
C24 C -0.27827(16) 0.1831(5) 0.12033(15) 0.0763(13) Uani 1 1 d . . . . .
H24A H -0.3094 0.1152 0.1084 0.092 Uiso 1 1 calc R U . . .
C25 C -0.28665(19) 0.2889(6) 0.14604(16) 0.0849(15) Uani 1 1 d . . . . .
H25A H -0.3240 0.2942 0.1522 0.102 Uiso 1 1 calc R U . . .
C26 C -0.24225(18) 0.3903(5) 0.16373(14) 0.0781(13) Uani 1 1 d . . . . .
H26A H -0.2491 0.4665 0.1809 0.094 Uiso 1 1 calc R U . . .
C27 C -0.18904(16) 0.3766(4) 0.15561(11) 0.0571(9) Uani 1 1 d . . . . .
H27A H -0.1585 0.4453 0.1682 0.069 Uiso 1 1 calc R U . . .
C28 C -0.01540(16) 0.1186(3) 0.05935(9) 0.0476(8) Uani 1 1 d . . . . .
C29 C -0.01194(19) 0.2282(4) 0.03073(11) 0.0592(10) Uani 1 1 d . . . . .
C30 C 0.0439(2) 0.2845(4) 0.03412(13) 0.0703(12) Uani 1 1 d . . . . .
H30A H 0.0465 0.3580 0.0146 0.084 Uiso 1 1 calc R U . . .
C31 C 0.0965(2) 0.2381(4) 0.06494(13) 0.0686(12) Uani 1 1 d . . . . .
C32 C 0.09194(17) 0.1292(4) 0.09240(11) 0.0571(9) Uani 1 1 d . . . . .
H32A H 0.1279 0.0951 0.1133 0.069 Uiso 1 1 calc R U . . .
C33 C 0.03683(16) 0.0674(3) 0.09074(10) 0.0481(8) Uani 1 1 d . . . . .
C34 C 0.03387(17) -0.0463(3) 0.12239(12) 0.0596(10) Uani 1 1 d . . . . .
H34A H 0.0743 -0.0872 0.1355 0.089 Uiso 1 1 calc R U . . .
H34B H 0.0058 -0.1210 0.1071 0.089 Uiso 1 1 calc R U . . .
H34C H 0.0196 -0.0050 0.1452 0.089 Uiso 1 1 calc R U . . .
C35 C -0.0698(2) 0.2810(5) -0.00283(12) 0.0885(15) Uani 1 1 d . . . . .
H35A H -0.0604 0.3623 -0.0186 0.133 Uiso 1 1 calc R U . . .
H35B H -0.0988 0.3104 0.0119 0.133 Uiso 1 1 calc R U . . .
H35C H -0.0875 0.2042 -0.0234 0.133 Uiso 1 1 calc R U . . .
C36 C 0.1575(2) 0.3069(6) 0.06896(16) 0.0997(16) Uani 1 1 d . . . . .
H36A H 0.1894 0.2597 0.0921 0.150 Uiso 1 1 calc R U . . .
H36B H 0.1561 0.4081 0.0760 0.150 Uiso 1 1 calc R U . . .
H36C H 0.1661 0.2972 0.0413 0.150 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N1 2.001(2) . ?
Fe1 N4 2.011(3) . ?
Fe1 C19 2.024(3) . ?
Fe1 C1 2.033(2) . ?
N1 C9 1.366(3) . ?
N1 C5 1.398(3) . ?
N2 C1 1.368(3) . ?
N2 C3 1.393(3) . ?
N2 C4 1.412(3) . ?
N3 C1 1.370(3) . ?
N3 C2 1.381(3) . ?
N3 C10 1.451(3) . ?
N4 C27 1.372(4) . ?
N4 C23 1.377(4) . ?
N5 C19 1.371(4) . ?
N5 C21 1.386(5) . ?
N5 C22 1.429(5) . ?
N6 C19 1.377(4) . ?
N6 C20 1.395(4) . ?
N6 C28 1.438(4) . ?
C2 C3 1.337(4) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C4 C5 1.372(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.448(4) . ?
C6 C7 1.344(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.411(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.353(4) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C15 1.390(4) . ?
C10 C11 1.396(4) . ?
C11 C12 1.388(4) . ?
C11 C17 1.505(4) . ?
C12 C13 1.378(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(5) . ?
C13 C18 1.522(4) . ?
C14 C15 1.398(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.501(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C21 1.339(6) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C22 C23 1.368(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.487(5) . ?
C24 C25 1.348(7) . ?
C24 H24A 0.9500 . ?
C25 C26 1.388(7) . ?
C25 H25A 0.9500 . ?
C26 C27 1.348(5) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 C33 1.400(4) . ?
C28 C29 1.404(5) . ?
C29 C30 1.373(6) . ?
C29 C35 1.521(5) . ?
C30 C31 1.382(6) . ?
C30 H30A 0.9500 . ?
C31 C32 1.380(5) . ?
C31 C36 1.526(6) . ?
C32 C33 1.392(5) . ?
C32 H32A 0.9500 . ?
C33 C34 1.495(5) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
N1 Fe1 N4 129.38(10) . . ?
N1 Fe1 C19 113.64(11) . . ?
N4 Fe1 C19 93.31(12) . . ?
N1 Fe1 C1 92.23(9) . . ?
N4 Fe1 C1 114.72(10) . . ?
C19 Fe1 C1 115.22(11) . . ?
C9 N1 C5 118.3(2) . . ?
C9 N1 Fe1 116.40(18) . . ?
C5 N1 Fe1 123.62(16) . . ?
C1 N2 C3 110.2(2) . . ?
C1 N2 C4 126.5(2) . . ?
C3 N2 C4 123.4(2) . . ?
C1 N3 C2 111.0(2) . . ?
C1 N3 C10 122.5(2) . . ?
C2 N3 C10 126.3(2) . . ?
C27 N4 C23 118.1(3) . . ?
C27 N4 Fe1 117.5(2) . . ?
C23 N4 Fe1 123.3(3) . . ?
C19 N5 C21 108.9(3) . . ?
C19 N5 C22 125.3(3) . . ?
C21 N5 C22 125.7(3) . . ?
C19 N6 C20 110.1(3) . . ?
C19 N6 C28 123.6(2) . . ?
C20 N6 C28 126.1(3) . . ?
N2 C1 N3 104.3(2) . . ?
N2 C1 Fe1 122.23(17) . . ?
N3 C1 Fe1 133.35(18) . . ?
C3 C2 N3 107.0(2) . . ?
C3 C2 H2A 126.5 . . ?
N3 C2 H2A 126.5 . . ?
C2 C3 N2 107.5(2) . . ?
C2 C3 H3A 126.2 . . ?
N2 C3 H3A 126.2 . . ?
C5 C4 N2 126.7(2) . . ?
C5 C4 H4A 116.7 . . ?
N2 C4 H4A 116.7 . . ?
C4 C5 N1 124.0(2) . . ?
C4 C5 C6 118.6(2) . . ?
N1 C5 C6 117.5(2) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C9 C8 C7 117.6(3) . . ?
C9 C8 H8A 121.2 . . ?
C7 C8 H8A 121.2 . . ?
C8 C9 N1 125.0(3) . . ?
C8 C9 H9A 117.5 . . ?
N1 C9 H9A 117.5 . . ?
C15 C10 C11 123.0(3) . . ?
C15 C10 N3 119.4(3) . . ?
C11 C10 N3 117.6(3) . . ?
C12 C11 C10 117.1(3) . . ?
C12 C11 C17 121.8(3) . . ?
C10 C11 C17 121.1(3) . . ?
C13 C12 C11 122.3(3) . . ?
C13 C12 H12A 118.8 . . ?
C11 C12 H12A 118.8 . . ?
C12 C13 C14 118.6(3) . . ?
C12 C13 C18 120.9(3) . . ?
C14 C13 C18 120.5(3) . . ?
C13 C14 C15 122.0(3) . . ?
C13 C14 H14A 119.0 . . ?
C15 C14 H14A 119.0 . . ?
C10 C15 C14 117.0(3) . . ?
C10 C15 C16 121.6(3) . . ?
C14 C15 C16 121.4(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N5 C19 N6 105.4(3) . . ?
N5 C19 Fe1 121.5(2) . . ?
N6 C19 Fe1 133.0(2) . . ?
C21 C20 N6 106.3(4) . . ?
C21 C20 H20A 126.9 . . ?
N6 C20 H20A 126.9 . . ?
C20 C21 N5 109.2(3) . . ?
C20 C21 H21A 125.4 . . ?
N5 C21 H21A 125.4 . . ?
C23 C22 N5 128.2(3) . . ?
C23 C22 H22A 115.9 . . ?
N5 C22 H22A 115.9 . . ?
C22 C23 N4 123.7(3) . . ?
C22 C23 C24 118.4(4) . . ?
N4 C23 C24 117.9(4) . . ?
C25 C24 C23 119.0(4) . . ?
C25 C24 H24A 120.5 . . ?
C23 C24 H24A 120.5 . . ?
C24 C25 C26 121.8(4) . . ?
C24 C25 H25A 119.1 . . ?
C26 C25 H25A 119.1 . . ?
C27 C26 C25 117.5(5) . . ?
C27 C26 H26A 121.2 . . ?
C25 C26 H26A 121.2 . . ?
C26 C27 N4 125.4(4) . . ?
C26 C27 H27A 117.3 . . ?
N4 C27 H27A 117.3 . . ?
C33 C28 C29 120.9(3) . . ?
C33 C28 N6 119.8(3) . . ?
C29 C28 N6 119.2(3) . . ?
C30 C29 C28 118.6(4) . . ?
C30 C29 C35 122.2(4) . . ?
C28 C29 C35 119.3(4) . . ?
C29 C30 C31 122.3(4) . . ?
C29 C30 H30A 118.8 . . ?
C31 C30 H30A 118.8 . . ?
C32 C31 C30 118.0(4) . . ?
C32 C31 C36 121.0(4) . . ?
C30 C31 C36 121.0(4) . . ?
C31 C32 C33 122.7(4) . . ?
C31 C32 H32A 118.7 . . ?
C33 C32 H32A 118.7 . . ?
C32 C33 C28 117.5(3) . . ?
C32 C33 C34 120.7(3) . . ?
C28 C33 C34 121.7(3) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C29 C35 H35A 109.5 . . ?
C29 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C29 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C3 N2 C1 N3 1.2(3) . . . . ?
C4 N2 C1 N3 -178.9(2) . . . . ?
C3 N2 C1 Fe1 -174.65(18) . . . . ?
C4 N2 C1 Fe1 5.3(3) . . . . ?
C2 N3 C1 N2 -0.7(3) . . . . ?
C10 N3 C1 N2 174.5(2) . . . . ?
C2 N3 C1 Fe1 174.5(2) . . . . ?
C10 N3 C1 Fe1 -10.4(4) . . . . ?
C1 N3 C2 C3 -0.1(3) . . . . ?
C10 N3 C2 C3 -175.0(3) . . . . ?
N3 C2 C3 N2 0.9(3) . . . . ?
C1 N2 C3 C2 -1.3(3) . . . . ?
C4 N2 C3 C2 178.7(2) . . . . ?
C1 N2 C4 C5 8.4(4) . . . . ?
C3 N2 C4 C5 -171.7(2) . . . . ?
N2 C4 C5 N1 -1.2(4) . . . . ?
N2 C4 C5 C6 179.1(2) . . . . ?
C9 N1 C5 C4 176.9(2) . . . . ?
Fe1 N1 C5 C4 -18.6(3) . . . . ?
C9 N1 C5 C6 -3.4(3) . . . . ?
Fe1 N1 C5 C6 161.17(17) . . . . ?
C4 C5 C6 C7 -178.5(3) . . . . ?
N1 C5 C6 C7 1.8(4) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C6 C7 C8 C9 -2.0(4) . . . . ?
C7 C8 C9 N1 0.2(5) . . . . ?
C5 N1 C9 C8 2.5(4) . . . . ?
Fe1 N1 C9 C8 -163.2(2) . . . . ?
C1 N3 C10 C15 87.1(3) . . . . ?
C2 N3 C10 C15 -98.5(3) . . . . ?
C1 N3 C10 C11 -90.9(3) . . . . ?
C2 N3 C10 C11 83.5(3) . . . . ?
C15 C10 C11 C12 0.9(4) . . . . ?
N3 C10 C11 C12 178.9(2) . . . . ?
C15 C10 C11 C17 -178.5(3) . . . . ?
N3 C10 C11 C17 -0.6(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C17 C11 C12 C13 179.9(3) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C11 C12 C13 C18 -179.3(3) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C18 C13 C14 C15 178.6(3) . . . . ?
C11 C10 C15 C14 -1.5(4) . . . . ?
N3 C10 C15 C14 -179.4(2) . . . . ?
C11 C10 C15 C16 176.7(3) . . . . ?
N3 C10 C15 C16 -1.2(4) . . . . ?
C13 C14 C15 C10 0.8(4) . . . . ?
C13 C14 C15 C16 -177.4(3) . . . . ?
C21 N5 C19 N6 1.4(4) . . . . ?
C22 N5 C19 N6 -176.9(3) . . . . ?
C21 N5 C19 Fe1 -174.6(2) . . . . ?
C22 N5 C19 Fe1 7.0(4) . . . . ?
C20 N6 C19 N5 -1.7(4) . . . . ?
C28 N6 C19 N5 173.4(3) . . . . ?
C20 N6 C19 Fe1 173.7(3) . . . . ?
C28 N6 C19 Fe1 -11.2(5) . . . . ?
C19 N6 C20 C21 1.3(4) . . . . ?
C28 N6 C20 C21 -173.7(3) . . . . ?
N6 C20 C21 N5 -0.4(5) . . . . ?
C19 N5 C21 C20 -0.7(5) . . . . ?
C22 N5 C21 C20 177.6(3) . . . . ?
C19 N5 C22 C23 8.5(5) . . . . ?
C21 N5 C22 C23 -169.5(4) . . . . ?
N5 C22 C23 N4 -3.8(6) . . . . ?
N5 C22 C23 C24 176.5(3) . . . . ?
C27 N4 C23 C22 176.3(3) . . . . ?
Fe1 N4 C23 C22 -15.8(4) . . . . ?
C27 N4 C23 C24 -4.1(4) . . . . ?
Fe1 N4 C23 C24 163.9(2) . . . . ?
C22 C23 C24 C25 -177.5(4) . . . . ?
N4 C23 C24 C25 2.8(5) . . . . ?
C23 C24 C25 C26 0.5(6) . . . . ?
C24 C25 C26 C27 -2.4(6) . . . . ?
C25 C26 C27 N4 1.0(6) . . . . ?
C23 N4 C27 C26 2.3(5) . . . . ?
Fe1 N4 C27 C26 -166.4(3) . . . . ?
C19 N6 C28 C33 85.0(4) . . . . ?
C20 N6 C28 C33 -100.7(4) . . . . ?
C19 N6 C28 C29 -92.0(4) . . . . ?
C20 N6 C28 C29 82.3(4) . . . . ?
C33 C28 C29 C30 0.0(5) . . . . ?
N6 C28 C29 C30 177.0(3) . . . . ?
C33 C28 C29 C35 -179.9(3) . . . . ?
N6 C28 C29 C35 -2.9(4) . . . . ?
C28 C29 C30 C31 -0.7(5) . . . . ?
C35 C29 C30 C31 179.2(4) . . . . ?
C29 C30 C31 C32 1.4(5) . . . . ?
C29 C30 C31 C36 -177.6(4) . . . . ?
C30 C31 C32 C33 -1.3(5) . . . . ?
C36 C31 C32 C33 177.6(3) . . . . ?
C31 C32 C33 C28 0.7(5) . . . . ?
C31 C32 C33 C34 -177.4(3) . . . . ?
C29 C28 C33 C32 0.0(4) . . . . ?
N6 C28 C33 C32 -176.9(3) . . . . ?
C29 C28 C33 C34 178.1(3) . . . . ?
N6 C28 C33 C34 1.2(4) . . . . ?

_refine_diff_density_max         0.571
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.063

# SQUEEZE RESULTS (Version = 201115)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.019 0.250 186 37 ' '
2 0.500 -0.020 0.750 186 37 ' '
3 0.000 0.519 0.250 186 37 ' '
4 0.000 0.480 0.750 186 37 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1493394'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H26 Br Fe N3'
_chemical_formula_weight         504.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0411(16)
_cell_length_b                   10.612(2)
_cell_length_c                   14.202(3)
_cell_angle_alpha                103.803(7)
_cell_angle_beta                 96.614(8)
_cell_angle_gamma                91.387(8)
_cell_volume                     1167.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15205
_cell_measurement_theta_min      1.979
_cell_measurement_theta_max      24.996

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.373
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5117
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15205
_diffrn_reflns_av_unetI/netI     0.1031
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.979
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             3992
_reflns_number_gt                2326
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3992
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.35135(9) 0.44355(6) 0.72691(5) 0.0345(2) Uani 1 1 d . . . . .
Br1 Br 0.50616(7) 0.34874(5) 0.59038(4) 0.0456(2) Uani 1 1 d . . . . .
N1 N 0.1649(5) 0.5519(4) 0.6608(3) 0.0356(11) Uani 1 1 d . . . . .
N2 N -0.0050(5) 0.3383(4) 0.7265(3) 0.0366(11) Uani 1 1 d . . . . .
N3 N 0.1554(6) 0.1796(4) 0.7230(3) 0.0373(11) Uani 1 1 d . . . . .
C1 C 0.4712(7) 0.5676(5) 0.8521(4) 0.0438(14) Uani 1 1 d . . . . .
H1A H 0.5218 0.5180 0.8979 0.053 Uiso 1 1 calc R U . . .
H1B H 0.5607 0.6219 0.8362 0.053 Uiso 1 1 calc R U . . .
C2 C 0.3378(7) 0.6509(5) 0.8962(4) 0.0393(14) Uani 1 1 d . . . . .
C3 C 0.2404(7) 0.6161(5) 0.9619(4) 0.0463(15) Uani 1 1 d . . . . .
H3A H 0.2624 0.5384 0.9822 0.056 Uiso 1 1 calc R U . . .
C4 C 0.1122(8) 0.6909(6) 0.9990(4) 0.0570(17) Uani 1 1 d . . . . .
H4A H 0.0496 0.6646 1.0445 0.068 Uiso 1 1 calc R U . . .
C5 C 0.0758(8) 0.8033(6) 0.9697(5) 0.0574(17) Uani 1 1 d . . . . .
H5A H -0.0126 0.8543 0.9941 0.069 Uiso 1 1 calc R U . . .
C6 C 0.1689(8) 0.8402(5) 0.9052(5) 0.0556(17) Uani 1 1 d . . . . .
H6A H 0.1446 0.9177 0.8851 0.067 Uiso 1 1 calc R U . . .
C7 C 0.2979(7) 0.7670(5) 0.8685(4) 0.0459(15) Uani 1 1 d . . . . .
H7A H 0.3607 0.7954 0.8240 0.055 Uiso 1 1 calc R U . . .
C8 C 0.1615(6) 0.3120(5) 0.7311(4) 0.0342(13) Uani 1 1 d . . . . .
C9 C -0.0075(7) 0.1301(5) 0.7139(4) 0.0472(15) Uani 1 1 d . . . . .
H9A H -0.0418 0.0416 0.7064 0.057 Uiso 1 1 calc R U . . .
C10 C -0.1093(7) 0.2298(5) 0.7176(4) 0.0465(15) Uani 1 1 d . . . . .
H10A H -0.2280 0.2261 0.7146 0.056 Uiso 1 1 calc R U . . .
C11 C -0.0621(7) 0.4729(5) 0.7386(4) 0.0431(14) Uani 1 1 d . . . . .
H11A H -0.0235 0.5230 0.8062 0.052 Uiso 1 1 calc R U . . .
H11B H -0.1862 0.4693 0.7299 0.052 Uiso 1 1 calc R U . . .
C12 C -0.0005(7) 0.5441(4) 0.6686(4) 0.0369(14) Uani 1 1 d . . . . .
C13 C -0.1154(7) 0.6043(5) 0.6148(4) 0.0454(15) Uani 1 1 d . . . . .
H13A H -0.2320 0.5958 0.6194 0.055 Uiso 1 1 calc R U . . .
C14 C -0.0580(8) 0.6763(5) 0.5549(4) 0.0463(15) Uani 1 1 d . . . . .
H14A H -0.1348 0.7187 0.5184 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1098(8) 0.6863(5) 0.5483(4) 0.0453(15) Uani 1 1 d . . . . .
H15A H 0.1515 0.7363 0.5080 0.054 Uiso 1 1 calc R U . . .
C16 C 0.2181(7) 0.6221(5) 0.6018(4) 0.0412(14) Uani 1 1 d . . . . .
H16A H 0.3345 0.6279 0.5965 0.049 Uiso 1 1 calc R U . . .
C17 C 0.3034(6) 0.1067(4) 0.7345(4) 0.0348(13) Uani 1 1 d . . . . .
C18 C 0.3882(7) 0.1235(5) 0.8281(4) 0.0397(14) Uani 1 1 d . . . . .
C19 C 0.5284(7) 0.0526(5) 0.8394(4) 0.0451(15) Uani 1 1 d . . . . .
H19A H 0.5891 0.0642 0.9026 0.054 Uiso 1 1 calc R U . . .
C20 C 0.5814(8) -0.0324(5) 0.7632(5) 0.0522(16) Uani 1 1 d . . . . .
C21 C 0.4955(8) -0.0471(5) 0.6709(5) 0.0504(17) Uani 1 1 d . . . . .
H21A H 0.5329 -0.1071 0.6175 0.061 Uiso 1 1 calc R U . . .
C22 C 0.3564(8) 0.0227(5) 0.6538(4) 0.0461(15) Uani 1 1 d . . . . .
C23 C 0.2671(9) 0.0104(5) 0.5520(4) 0.066(2) Uani 1 1 d . . . . .
H23A H 0.1479 -0.0124 0.5507 0.100 Uiso 1 1 calc R U . . .
H23B H 0.3164 -0.0576 0.5055 0.100 Uiso 1 1 calc R U . . .
H23C H 0.2792 0.0934 0.5338 0.100 Uiso 1 1 calc R U . . .
C24 C 0.3325(7) 0.2146(5) 0.9173(4) 0.0474(15) Uani 1 1 d . . . . .
H24A H 0.2097 0.2131 0.9107 0.071 Uiso 1 1 calc R U . . .
H24B H 0.3771 0.3032 0.9227 0.071 Uiso 1 1 calc R U . . .
H24C H 0.3747 0.1864 0.9761 0.071 Uiso 1 1 calc R U . . .
C25 C 0.7324(8) -0.1138(6) 0.7795(6) 0.078(2) Uani 1 1 d . . . . .
H25A H 0.8179 -0.0605 0.8285 0.118 Uiso 1 1 calc R U . . .
H25B H 0.7795 -0.1439 0.7178 0.118 Uiso 1 1 calc R U . . .
H25C H 0.6963 -0.1889 0.8023 0.118 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C8 2.060(5) . ?
Fe1 C1 2.061(5) . ?
Fe1 N1 2.174(4) . ?
Fe1 Br1 2.4511(10) . ?
N1 C16 1.342(6) . ?
N1 C12 1.350(6) . ?
N2 C8 1.371(6) . ?
N2 C10 1.380(7) . ?
N2 C11 1.489(6) . ?
N3 C9 1.380(7) . ?
N3 C8 1.382(6) . ?
N3 C17 1.450(6) . ?
C1 C2 1.504(7) . ?
C2 C3 1.393(8) . ?
C2 C7 1.413(7) . ?
C3 C4 1.391(7) . ?
C4 C5 1.382(7) . ?
C5 C6 1.367(8) . ?
C6 C7 1.386(7) . ?
C9 C10 1.348(7) . ?
C11 C12 1.502(7) . ?
C12 C13 1.395(7) . ?
C13 C14 1.380(8) . ?
C14 C15 1.367(8) . ?
C15 C16 1.387(7) . ?
C17 C22 1.391(7) . ?
C17 C18 1.391(7) . ?
C18 C19 1.385(7) . ?
C18 C24 1.520(7) . ?
C19 C20 1.351(7) . ?
C20 C21 1.381(8) . ?
C20 C25 1.535(8) . ?
C21 C22 1.387(8) . ?
C22 C23 1.513(8) . ?

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
C8 Fe1 C1 121.9(2) . . ?
C8 Fe1 N1 88.29(18) . . ?
C1 Fe1 N1 107.66(17) . . ?
C8 Fe1 Br1 108.34(13) . . ?
C1 Fe1 Br1 120.87(16) . . ?
N1 Fe1 Br1 102.64(11) . . ?
C16 N1 C12 118.7(5) . . ?
C16 N1 Fe1 116.8(4) . . ?
C12 N1 Fe1 124.3(3) . . ?
C8 N2 C10 113.1(4) . . ?
C8 N2 C11 122.1(4) . . ?
C10 N2 C11 124.5(4) . . ?
C9 N3 C8 111.4(4) . . ?
C9 N3 C17 124.9(4) . . ?
C8 N3 C17 123.3(5) . . ?
C2 C1 Fe1 105.7(3) . . ?
C3 C2 C7 115.9(5) . . ?
C3 C2 C1 122.9(5) . . ?
C7 C2 C1 121.1(5) . . ?
C4 C3 C2 122.4(5) . . ?
C5 C4 C3 120.1(6) . . ?
C6 C5 C4 119.0(5) . . ?
C5 C6 C7 121.4(5) . . ?
C6 C7 C2 121.2(6) . . ?
N2 C8 N3 102.1(4) . . ?
N2 C8 Fe1 124.2(4) . . ?
N3 C8 Fe1 132.9(4) . . ?
C10 C9 N3 107.8(5) . . ?
C9 C10 N2 105.6(5) . . ?
N2 C11 C12 114.2(4) . . ?
N1 C12 C13 121.1(5) . . ?
N1 C12 C11 119.8(5) . . ?
C13 C12 C11 119.1(5) . . ?
C14 C13 C12 119.2(6) . . ?
C15 C14 C13 119.7(5) . . ?
C14 C15 C16 118.6(5) . . ?
N1 C16 C15 122.7(5) . . ?
C22 C17 C18 121.9(5) . . ?
C22 C17 N3 120.2(5) . . ?
C18 C17 N3 117.8(4) . . ?
C19 C18 C17 117.9(5) . . ?
C19 C18 C24 119.3(5) . . ?
C17 C18 C24 122.8(5) . . ?
C20 C19 C18 122.0(6) . . ?
C19 C20 C21 119.1(5) . . ?
C19 C20 C25 120.4(6) . . ?
C21 C20 C25 120.5(6) . . ?
C20 C21 C22 122.1(5) . . ?
C21 C22 C17 116.9(5) . . ?
C21 C22 C23 122.0(5) . . ?
C17 C22 C23 121.1(5) . . ?

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1493395'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H33 Fe N3'
_chemical_formula_weight         515.46

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2244(9)
_cell_length_b                   9.8456(10)
_cell_length_c                   15.6959(14)
_cell_angle_alpha                94.162(4)
_cell_angle_beta                 104.009(4)
_cell_angle_gamma                96.291(4)
_cell_volume                     1367.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    21621
_cell_measurement_theta_min      2.092
_cell_measurement_theta_max      27.494

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.576
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6808
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21621
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.092
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6226
_reflns_number_gt                4338
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+0.3400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6226
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.16271(3) 0.31236(3) 0.25624(2) 0.02326(10) Uani 1 1 d . . . . .
N1 N 0.25191(19) 0.30091(18) 0.13765(11) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.45377(19) 0.50039(17) 0.27524(11) 0.0240(4) Uani 1 1 d . . . . .
N3 N 0.32208(19) 0.61202(17) 0.34222(11) 0.0246(4) Uani 1 1 d . . . . .
C1 C -0.0626(2) 0.3536(2) 0.23692(15) 0.0295(5) Uani 1 1 d . . . . .
H1A H -0.1147 0.2977 0.2733 0.035 Uiso 1 1 calc R U . . .
H1B H -0.0648 0.4518 0.2544 0.035 Uiso 1 1 calc R U . . .
C2 C -0.1373(2) 0.3188(2) 0.14346(15) 0.0258(5) Uani 1 1 d . . . . .
C3 C -0.2018(2) 0.1840(2) 0.10877(15) 0.0301(5) Uani 1 1 d . . . . .
H3A H -0.2024 0.1147 0.1478 0.036 Uiso 1 1 calc R U . . .
C4 C -0.2647(3) 0.1494(2) 0.01893(16) 0.0345(6) Uani 1 1 d . . . . .
H4A H -0.3084 0.0575 -0.0023 0.041 Uiso 1 1 calc R U . . .
C5 C -0.2641(3) 0.2478(2) -0.03988(15) 0.0322(5) Uani 1 1 d . . . . .
H5A H -0.3060 0.2238 -0.1014 0.039 Uiso 1 1 calc R U . . .
C6 C -0.2020(3) 0.3806(2) -0.00781(15) 0.0317(5) Uani 1 1 d . . . . .
H6A H -0.2011 0.4489 -0.0475 0.038 Uiso 1 1 calc R U . . .
C7 C -0.1409(2) 0.4154(2) 0.08140(15) 0.0298(5) Uani 1 1 d . . . . .
H7A H -0.0996 0.5081 0.1017 0.036 Uiso 1 1 calc R U . . .
C8 C 0.1854(3) 0.1095(2) 0.28234(16) 0.0336(6) Uani 1 1 d . . . . .
H8A H 0.1486 0.0916 0.3353 0.040 Uiso 1 1 calc R U . . .
H8B H 0.1206 0.0470 0.2320 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3403(3) 0.0775(2) 0.29709(15) 0.0299(5) Uani 1 1 d . . . . .
C10 C 0.4411(3) 0.0952(2) 0.38104(17) 0.0387(6) Uani 1 1 d . . . . .
H10A H 0.4055 0.1208 0.4311 0.046 Uiso 1 1 calc R U . . .
C11 C 0.5899(3) 0.0767(3) 0.3929(2) 0.0484(7) Uani 1 1 d . . . . .
H11A H 0.6554 0.0905 0.4506 0.058 Uiso 1 1 calc R U . . .
C12 C 0.6456(3) 0.0380(3) 0.3213(2) 0.0542(8) Uani 1 1 d . . . . .
H12A H 0.7491 0.0276 0.3294 0.065 Uiso 1 1 calc R U . . .
C13 C 0.5479(3) 0.0149(3) 0.2382(2) 0.0476(7) Uani 1 1 d . . . . .
H13A H 0.5838 -0.0148 0.1890 0.057 Uiso 1 1 calc R U . . .
C14 C 0.3992(3) 0.0344(2) 0.22600(16) 0.0351(6) Uani 1 1 d . . . . .
H14A H 0.3342 0.0185 0.1682 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3243(2) 0.4842(2) 0.30233(13) 0.0227(5) Uani 1 1 d . . . . .
C16 C 0.4447(2) 0.7031(2) 0.33838(15) 0.0310(5) Uani 1 1 d . . . . .
H16A H 0.4660 0.7972 0.3610 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5283(2) 0.6323(2) 0.29635(15) 0.0289(5) Uani 1 1 d . . . . .
H17A H 0.6204 0.6665 0.2838 0.035 Uiso 1 1 calc R U . . .
C18 C 0.5044(2) 0.3884(2) 0.22812(14) 0.0269(5) Uani 1 1 d . . . . .
H18A H 0.5152 0.3108 0.2649 0.032 Uiso 1 1 calc R U . . .
H18B H 0.6049 0.4203 0.2194 0.032 Uiso 1 1 calc R U . . .
C19 C 0.3976(2) 0.3384(2) 0.13944(14) 0.0243(5) Uani 1 1 d . . . . .
C20 C 0.4508(3) 0.3255(2) 0.06452(15) 0.0337(6) Uani 1 1 d . . . . .
H20A H 0.5535 0.3556 0.0673 0.040 Uiso 1 1 calc R U . . .
C21 C 0.3534(3) 0.2685(3) -0.01449(16) 0.0420(7) Uani 1 1 d . . . . .
H21A H 0.3878 0.2587 -0.0667 0.050 Uiso 1 1 calc R U . . .
C22 C 0.2056(3) 0.2261(3) -0.01605(15) 0.0365(6) Uani 1 1 d . . . . .
H22A H 0.1368 0.1843 -0.0691 0.044 Uiso 1 1 calc R U . . .
C23 C 0.1585(3) 0.2450(2) 0.06024(14) 0.0285(5) Uani 1 1 d . . . . .
H23A H 0.0557 0.2175 0.0582 0.034 Uiso 1 1 calc R U . . .
C24 C 0.2014(2) 0.6523(2) 0.37861(13) 0.0222(5) Uani 1 1 d . . . . .
C25 C 0.1978(2) 0.6257(2) 0.46374(14) 0.0270(5) Uani 1 1 d . . . . .
C26 C 0.0844(3) 0.6742(2) 0.49719(14) 0.0313(5) Uani 1 1 d . . . . .
H26A H 0.0787 0.6559 0.5550 0.038 Uiso 1 1 calc R U . . .
C27 C -0.0200(3) 0.7481(2) 0.44919(15) 0.0310(5) Uani 1 1 d . . . . .
C28 C -0.0142(2) 0.7699(2) 0.36388(15) 0.0291(5) Uani 1 1 d . . . . .
H28A H -0.0869 0.8189 0.3299 0.035 Uiso 1 1 calc R U . . .
C29 C 0.0952(2) 0.7222(2) 0.32645(14) 0.0250(5) Uani 1 1 d . . . . .
C30 C 0.0989(3) 0.7448(2) 0.23367(14) 0.0336(6) Uani 1 1 d . . . . .
H30A H 0.0054 0.7782 0.2038 0.050 Uiso 1 1 calc R U . . .
H30B H 0.1085 0.6580 0.2021 0.050 Uiso 1 1 calc R U . . .
H30C H 0.1851 0.8129 0.2344 0.050 Uiso 1 1 calc R U . . .
C31 C 0.3141(3) 0.5511(3) 0.51941(15) 0.0393(6) Uani 1 1 d . . . . .
H31A H 0.3273 0.4688 0.4846 0.059 Uiso 1 1 calc R U . . .
H31B H 0.2805 0.5243 0.5712 0.059 Uiso 1 1 calc R U . . .
H31C H 0.4102 0.6116 0.5388 0.059 Uiso 1 1 calc R U . . .
C32 C -0.1353(3) 0.8074(3) 0.48947(18) 0.0468(7) Uani 1 1 d . . . . .
H32A H -0.1475 0.7578 0.5397 0.070 Uiso 1 1 calc R U . . .
H32B H -0.2320 0.7981 0.4452 0.070 Uiso 1 1 calc R U . . .
H32C H -0.1012 0.9048 0.5096 0.070 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C15 2.087(2) . ?
Fe1 C8 2.090(2) . ?
Fe1 C1 2.115(2) . ?
Fe1 N1 2.2105(17) . ?
N1 C23 1.347(3) . ?
N1 C19 1.347(3) . ?
N2 C15 1.358(3) . ?
N2 C17 1.379(3) . ?
N2 C18 1.464(3) . ?
N3 C15 1.369(3) . ?
N3 C16 1.381(3) . ?
N3 C24 1.447(3) . ?
C1 C2 1.459(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.406(3) . ?
C2 C7 1.407(3) . ?
C3 C4 1.390(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.376(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.379(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C9 1.464(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.403(3) . ?
C9 C14 1.412(3) . ?
C10 C11 1.374(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.390(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.376(4) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C16 C17 1.346(3) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.510(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.383(3) . ?
C20 C21 1.382(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.375(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.376(3) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 C25 1.387(3) . ?
C24 C29 1.395(3) . ?
C25 C26 1.392(3) . ?
C25 C31 1.505(3) . ?
C26 C27 1.381(3) . ?
C26 H26A 0.9500 . ?
C27 C28 1.384(3) . ?
C27 C32 1.510(3) . ?
C28 C29 1.390(3) . ?
C28 H28A 0.9500 . ?
C29 C30 1.497(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
C15 Fe1 C8 126.81(9) . . ?
C15 Fe1 C1 114.40(8) . . ?
C8 Fe1 C1 112.16(9) . . ?
C15 Fe1 N1 86.05(7) . . ?
C8 Fe1 N1 95.42(8) . . ?
C1 Fe1 N1 116.38(8) . . ?
C23 N1 C19 117.73(18) . . ?
C23 N1 Fe1 118.57(14) . . ?
C19 N1 Fe1 123.54(14) . . ?
C15 N2 C17 112.48(17) . . ?
C15 N2 C18 122.54(18) . . ?
C17 N2 C18 124.97(18) . . ?
C15 N3 C16 111.93(18) . . ?
C15 N3 C24 124.98(17) . . ?
C16 N3 C24 122.94(17) . . ?
C2 C1 Fe1 107.70(14) . . ?
C2 C1 H1A 110.2 . . ?
Fe1 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
Fe1 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C3 C2 C7 115.6(2) . . ?
C3 C2 C1 121.9(2) . . ?
C7 C2 C1 122.4(2) . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
C6 C7 C2 122.5(2) . . ?
C6 C7 H7A 118.8 . . ?
C2 C7 H7A 118.8 . . ?
C9 C8 Fe1 113.76(16) . . ?
C9 C8 H8A 108.8 . . ?
Fe1 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
Fe1 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C14 116.1(2) . . ?
C10 C9 C8 122.5(2) . . ?
C14 C9 C8 121.3(2) . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 H10A 119.1 . . ?
C9 C10 H10A 119.1 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C9 121.8(2) . . ?
C13 C14 H14A 119.1 . . ?
C9 C14 H14A 119.1 . . ?
N2 C15 N3 102.64(17) . . ?
N2 C15 Fe1 121.53(14) . . ?
N3 C15 Fe1 133.98(15) . . ?
C17 C16 N3 106.56(19) . . ?
C17 C16 H16A 126.7 . . ?
N3 C16 H16A 126.7 . . ?
C16 C17 N2 106.39(19) . . ?
C16 C17 H17A 126.8 . . ?
N2 C17 H17A 126.8 . . ?
N2 C18 C19 112.94(16) . . ?
N2 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N2 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
N1 C19 C20 122.1(2) . . ?
N1 C19 C18 117.36(18) . . ?
C20 C19 C18 120.5(2) . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H20A 120.3 . . ?
C19 C20 H20A 120.3 . . ?
C22 C21 C20 118.7(2) . . ?
C22 C21 H21A 120.7 . . ?
C20 C21 H21A 120.7 . . ?
C21 C22 C23 119.1(2) . . ?
C21 C22 H22A 120.4 . . ?
C23 C22 H22A 120.4 . . ?
N1 C23 C22 122.9(2) . . ?
N1 C23 H23A 118.6 . . ?
C22 C23 H23A 118.6 . . ?
C25 C24 C29 122.4(2) . . ?
C25 C24 N3 119.99(19) . . ?
C29 C24 N3 117.52(18) . . ?
C24 C25 C26 117.4(2) . . ?
C24 C25 C31 121.8(2) . . ?
C26 C25 C31 120.8(2) . . ?
C27 C26 C25 122.2(2) . . ?
C27 C26 H26A 118.9 . . ?
C25 C26 H26A 118.9 . . ?
C26 C27 C28 118.5(2) . . ?
C26 C27 C32 120.9(2) . . ?
C28 C27 C32 120.6(2) . . ?
C27 C28 C29 121.9(2) . . ?
C27 C28 H28A 119.0 . . ?
C29 C28 H28A 119.0 . . ?
C28 C29 C24 117.5(2) . . ?
C28 C29 C30 121.4(2) . . ?
C24 C29 C30 121.1(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 C31 H31A 109.5 . . ?
C25 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C25 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 C1 C2 C3 84.7(2) . . . . ?
Fe1 C1 C2 C7 -91.0(2) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 -176.0(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C1 C2 C7 C6 175.3(2) . . . . ?
Fe1 C8 C9 C10 89.4(2) . . . . ?
Fe1 C8 C9 C14 -86.7(2) . . . . ?
C14 C9 C10 C11 2.3(3) . . . . ?
C8 C9 C10 C11 -174.0(2) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C13 -1.7(4) . . . . ?
C11 C12 C13 C14 2.2(4) . . . . ?
C12 C13 C14 C9 -0.4(4) . . . . ?
C10 C9 C14 C13 -1.8(3) . . . . ?
C8 C9 C14 C13 174.6(2) . . . . ?
C17 N2 C15 N3 -0.6(2) . . . . ?
C18 N2 C15 N3 -179.93(17) . . . . ?
C17 N2 C15 Fe1 165.94(14) . . . . ?
C18 N2 C15 Fe1 -13.4(3) . . . . ?
C16 N3 C15 N2 0.8(2) . . . . ?
C24 N3 C15 N2 176.44(18) . . . . ?
C16 N3 C15 Fe1 -163.12(17) . . . . ?
C24 N3 C15 Fe1 12.5(3) . . . . ?
C15 N3 C16 C17 -0.8(2) . . . . ?
C24 N3 C16 C17 -176.52(19) . . . . ?
N3 C16 C17 N2 0.4(2) . . . . ?
C15 N2 C17 C16 0.1(3) . . . . ?
C18 N2 C17 C16 179.46(19) . . . . ?
C15 N2 C18 C19 63.5(3) . . . . ?
C17 N2 C18 C19 -115.8(2) . . . . ?
C23 N1 C19 C20 2.3(3) . . . . ?
Fe1 N1 C19 C20 177.73(16) . . . . ?
C23 N1 C19 C18 -174.37(18) . . . . ?
Fe1 N1 C19 C18 1.0(3) . . . . ?
N2 C18 C19 N1 -53.6(3) . . . . ?
N2 C18 C19 C20 129.6(2) . . . . ?
N1 C19 C20 C21 -2.1(3) . . . . ?
C18 C19 C20 C21 174.5(2) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C20 C21 C22 C23 1.7(4) . . . . ?
C19 N1 C23 C22 -0.5(3) . . . . ?
Fe1 N1 C23 C22 -176.14(17) . . . . ?
C21 C22 C23 N1 -1.5(4) . . . . ?
C15 N3 C24 C25 84.5(3) . . . . ?
C16 N3 C24 C25 -100.4(2) . . . . ?
C15 N3 C24 C29 -98.0(2) . . . . ?
C16 N3 C24 C29 77.1(3) . . . . ?
C29 C24 C25 C26 -1.3(3) . . . . ?
N3 C24 C25 C26 176.14(18) . . . . ?
C29 C24 C25 C31 -179.5(2) . . . . ?
N3 C24 C25 C31 -2.1(3) . . . . ?
C24 C25 C26 C27 -1.1(3) . . . . ?
C31 C25 C26 C27 177.2(2) . . . . ?
C25 C26 C27 C28 2.4(3) . . . . ?
C25 C26 C27 C32 -175.9(2) . . . . ?
C26 C27 C28 C29 -1.4(3) . . . . ?
C32 C27 C28 C29 176.9(2) . . . . ?
C27 C28 C29 C24 -0.8(3) . . . . ?
C27 C28 C29 C30 179.1(2) . . . . ?
C25 C24 C29 C28 2.2(3) . . . . ?
N3 C24 C29 C28 -175.29(18) . . . . ?
C25 C24 C29 C30 -177.7(2) . . . . ?
N3 C24 C29 C30 4.8(3) . . . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1493396'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Fe N3 O3'
_chemical_formula_weight         417.24

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'

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

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

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

_cell_length_a                   15.764(2)
_cell_length_b                   8.8282(10)
_cell_length_c                   16.118(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.981(6)
_cell_angle_gamma                90
_cell_volume                     1962.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    24729
_cell_measurement_theta_min      1.483
_cell_measurement_theta_max      27.593

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.795
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6948
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24729
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.483
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4536
_reflns_number_gt                3381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+0.0928P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4536
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.82280(2) 0.86634(3) 0.53381(2) 0.02225(12) Uani 1 1 d . . . . .
O1 O 0.90992(16) 1.15215(18) 0.62389(13) 0.0518(6) Uani 1 1 d . . . . .
O2 O 0.73984(16) 1.0624(2) 0.36683(12) 0.0533(6) Uani 1 1 d . . . . .
O3 O 0.63501(15) 0.8410(2) 0.52492(15) 0.0538(6) Uani 1 1 d . . . . .
N1 N 0.86353(14) 0.70256(19) 0.46768(11) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.87360(13) 0.58010(19) 0.63624(12) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.94132(13) 0.75423(19) 0.73997(12) 0.0233(4) Uani 1 1 d . . . . .
C1 C 0.88414(18) 1.0309(3) 0.59312(15) 0.0306(5) Uani 1 1 d . . . . .
C2 C 0.77212(19) 0.9812(2) 0.43129(16) 0.0332(6) Uani 1 1 d . . . . .
C3 C 0.70920(19) 0.8396(3) 0.52656(17) 0.0333(6) Uani 1 1 d . . . . .
C4 C 0.88379(15) 0.7339(2) 0.64489(14) 0.0210(4) Uani 1 1 d . . . . .
C5 C 0.96537(18) 0.6156(2) 0.78790(15) 0.0279(5) Uani 1 1 d . . . . .
H5A H 1.0045 0.6011 0.8543 0.033 Uiso 1 1 calc R U . . .
C6 C 0.92293(17) 0.5074(2) 0.72262(15) 0.0263(5) Uani 1 1 d . . . . .
H6A H 0.9261 0.4013 0.7335 0.032 Uiso 1 1 calc R U . . .
C7 C 0.81660(18) 0.5082(2) 0.54427(14) 0.0275(5) Uani 1 1 d . . . . .
H7A H 0.7478 0.5388 0.5173 0.033 Uiso 1 1 calc R U . . .
H7B H 0.8202 0.3968 0.5523 0.033 Uiso 1 1 calc R U . . .
C8 C 0.85282(16) 0.5519(2) 0.47744(14) 0.0262(5) Uani 1 1 d . . . . .
C9 C 0.87207(17) 0.4432(2) 0.42672(15) 0.0312(6) Uani 1 1 d . . . . .
H9A H 0.8651 0.3387 0.4361 0.037 Uiso 1 1 calc R U . . .
C10 C 0.90131(18) 0.4878(3) 0.36275(16) 0.0354(6) Uani 1 1 d . . . . .
H10A H 0.9130 0.4149 0.3260 0.042 Uiso 1 1 calc R U . . .
C11 C 0.91339(19) 0.6398(3) 0.35290(16) 0.0337(6) Uani 1 1 d . . . . .
H11A H 0.9338 0.6736 0.3094 0.040 Uiso 1 1 calc R U . . .
C12 C 0.89552(18) 0.7424(3) 0.40694(15) 0.0304(5) Uani 1 1 d . . . . .
H12A H 0.9063 0.8468 0.4011 0.036 Uiso 1 1 calc R U . . .
C13 C 0.97327(17) 0.8969(2) 0.78890(14) 0.0243(5) Uani 1 1 d . . . . .
C14 C 0.9165(2) 0.9647(3) 0.82223(16) 0.0344(6) Uani 1 1 d . . . . .
C15 C 0.9522(2) 1.0977(3) 0.87511(18) 0.0415(7) Uani 1 1 d . . . . .
H15A H 0.9153 1.1459 0.8998 0.050 Uiso 1 1 calc R U . . .
C16 C 1.0394(2) 1.1610(3) 0.89254(16) 0.0366(6) Uani 1 1 d . . . . .
C17 C 1.09196(18) 1.0923(2) 0.85470(15) 0.0313(6) Uani 1 1 d . . . . .
H17A H 1.1505 1.1377 0.8640 0.038 Uiso 1 1 calc R U . . .
C18 C 1.06079(17) 0.9577(2) 0.80325(14) 0.0270(5) Uani 1 1 d . . . . .
C19 C 1.11935(19) 0.8837(3) 0.76363(18) 0.0359(6) Uani 1 1 d . . . . .
H19A H 1.0779 0.8652 0.6956 0.054 Uiso 1 1 calc R U . . .
H19B H 1.1453 0.7872 0.7962 0.054 Uiso 1 1 calc R U . . .
H19C H 1.1730 0.9505 0.7732 0.054 Uiso 1 1 calc R U . . .
C20 C 0.8193(2) 0.9010(4) 0.8007(2) 0.0544(8) Uani 1 1 d . . . . .
H20A H 0.8257 0.7922 0.8145 0.082 Uiso 1 1 calc R U . . .
H20B H 0.7728 0.9172 0.7335 0.082 Uiso 1 1 calc R U . . .
H20C H 0.7963 0.9521 0.8400 0.082 Uiso 1 1 calc R U . . .
C21 C 1.0778(2) 1.3029(3) 0.95189(19) 0.0547(9) Uani 1 1 d . . . . .
H21A H 1.0272 1.3472 0.9630 0.082 Uiso 1 1 calc R U . . .
H21B H 1.0969 1.3762 0.9183 0.082 Uiso 1 1 calc R U . . .
H21C H 1.1342 1.2773 1.0128 0.082 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C1 1.751(2) . ?
Fe1 C3 1.753(3) . ?
Fe1 C2 1.766(2) . ?
Fe1 C4 1.957(2) . ?
Fe1 N1 2.0742(18) . ?
O1 C1 1.167(3) . ?
O2 C2 1.157(3) . ?
O3 C3 1.157(3) . ?
N1 C12 1.347(3) . ?
N1 C8 1.360(3) . ?
N2 C4 1.367(3) . ?
N2 C6 1.381(3) . ?
N2 C7 1.455(3) . ?
N3 C4 1.362(2) . ?
N3 C5 1.398(3) . ?
N3 C13 1.441(3) . ?
C5 C6 1.336(3) . ?
C7 C8 1.494(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.375(4) . ?
C10 C11 1.376(3) . ?
C11 C12 1.377(3) . ?
C13 C14 1.384(3) . ?
C13 C18 1.391(3) . ?
C14 C15 1.398(3) . ?
C14 C20 1.506(4) . ?
C15 C16 1.380(4) . ?
C16 C17 1.385(4) . ?
C16 C21 1.513(3) . ?
C17 C18 1.395(3) . ?
C18 C19 1.502(4) . ?

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
C1 Fe1 C3 115.11(12) . . ?
C1 Fe1 C2 85.07(10) . . ?
C3 Fe1 C2 91.75(12) . . ?
C1 Fe1 C4 95.72(9) . . ?
C3 Fe1 C4 90.79(10) . . ?
C2 Fe1 C4 176.72(11) . . ?
C1 Fe1 N1 129.24(10) . . ?
C3 Fe1 N1 115.62(10) . . ?
C2 Fe1 N1 91.82(9) . . ?
C4 Fe1 N1 85.21(8) . . ?
C12 N1 C8 116.79(19) . . ?
C12 N1 Fe1 120.62(14) . . ?
C8 N1 Fe1 122.41(15) . . ?
C4 N2 C6 112.22(16) . . ?
C4 N2 C7 121.43(16) . . ?
C6 N2 C7 126.36(17) . . ?
C4 N3 C5 111.16(17) . . ?
C4 N3 C13 126.59(17) . . ?
C5 N3 C13 122.23(17) . . ?
O1 C1 Fe1 168.5(2) . . ?
O2 C2 Fe1 176.8(2) . . ?
O3 C3 Fe1 171.4(2) . . ?
N3 C4 N2 103.11(16) . . ?
N3 C4 Fe1 135.63(15) . . ?
N2 C4 Fe1 121.26(14) . . ?
C6 C5 N3 107.01(18) . . ?
C5 C6 N2 106.51(17) . . ?
N2 C7 C8 111.04(18) . . ?
N1 C8 C9 122.3(2) . . ?
N1 C8 C7 116.61(19) . . ?
C9 C8 C7 121.1(2) . . ?
C10 C9 C8 119.5(2) . . ?
C9 C10 C11 118.7(2) . . ?
C10 C11 C12 119.1(2) . . ?
N1 C12 C11 123.4(2) . . ?
C14 C13 C18 123.0(2) . . ?
C14 C13 N3 118.1(2) . . ?
C18 C13 N3 118.9(2) . . ?
C13 C14 C15 117.0(2) . . ?
C13 C14 C20 121.7(2) . . ?
C15 C14 C20 121.2(3) . . ?
C16 C15 C14 122.1(3) . . ?
C15 C16 C17 118.8(2) . . ?
C15 C16 C21 121.2(3) . . ?
C17 C16 C21 120.0(3) . . ?
C16 C17 C18 121.4(2) . . ?
C13 C18 C17 117.5(2) . . ?
C13 C18 C19 121.73(19) . . ?
C17 C18 C19 120.7(2) . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1493397'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 Fe N3 O4'
_chemical_formula_weight         445.25

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.7951(11)
_cell_length_b                   13.2320(10)
_cell_length_c                   12.3477(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.594(4)
_cell_angle_gamma                90
_cell_volume                     2083.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19431
_cell_measurement_theta_min      2.218
_cell_measurement_theta_max      27.482

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.757
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19431
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.218
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4755
_reflns_number_gt                3689
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.7965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4755
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.19105(2) 0.12934(2) 0.78982(2) 0.01594(8) Uani 1 1 d . . . . .
O1 O 0.27197(12) 0.32660(11) 0.86494(12) 0.0317(3) Uani 1 1 d . . . . .
O2 O 0.02623(11) 0.13089(12) 0.94304(12) 0.0320(3) Uani 1 1 d . . . . .
O3 O 0.15786(13) 0.20614(12) 0.56647(12) 0.0383(4) Uani 1 1 d . . . . .
O4 O 0.40310(12) 0.06378(12) 0.87250(14) 0.0428(4) Uani 1 1 d . . . . .
N1 N 0.02977(12) -0.01019(12) 0.67700(12) 0.0200(3) Uani 1 1 d . . . . .
N2 N 0.17233(12) -0.09166(12) 0.71887(13) 0.0197(3) Uani 1 1 d . . . . .
N3 N -0.23210(14) 0.09481(14) 0.69492(15) 0.0323(4) Uani 1 1 d . . . . .
C1 C 0.23914(15) 0.24950(14) 0.83676(15) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.09112(15) 0.12989(14) 0.88373(15) 0.0205(4) Uani 1 1 d . . . . .
C3 C 0.17246(15) 0.17635(15) 0.65424(16) 0.0236(4) Uani 1 1 d . . . . .
C4 C 0.31912(16) 0.07907(14) 0.83732(17) 0.0248(4) Uani 1 1 d . . . . .
C5 C 0.12838(14) 0.00172(14) 0.72735(14) 0.0174(4) Uani 1 1 d . . . . .
C6 C 0.10272(15) -0.15925(15) 0.66561(17) 0.0253(4) Uani 1 1 d . . . . .
H6A H 0.1157 -0.2284 0.6508 0.030 Uiso 1 1 calc R U . . .
C7 C 0.01393(15) -0.10828(16) 0.63917(16) 0.0259(4) Uani 1 1 d . . . . .
H7A H -0.0481 -0.1343 0.6017 0.031 Uiso 1 1 calc R U . . .
C8 C -0.05288(14) 0.06584(15) 0.66473(16) 0.0229(4) Uani 1 1 d . . . . .
H8A H -0.0777 0.0711 0.5869 0.027 Uiso 1 1 calc R U . . .
H8B H -0.0231 0.1322 0.6879 0.027 Uiso 1 1 calc R U . . .
C9 C -0.14578(14) 0.04329(14) 0.72949(15) 0.0196(4) Uani 1 1 d . . . . .
C10 C -0.14186(15) -0.02181(15) 0.81750(16) 0.0222(4) Uani 1 1 d . . . . .
H10A H -0.0792 -0.0573 0.8396 0.027 Uiso 1 1 calc R U . . .
C11 C -0.23108(16) -0.03422(15) 0.87278(16) 0.0257(4) Uani 1 1 d . . . . .
H11A H -0.2304 -0.0781 0.9337 0.031 Uiso 1 1 calc R U . . .
C12 C -0.32088(16) 0.01806(16) 0.83803(18) 0.0305(5) Uani 1 1 d . . . . .
H12A H -0.3834 0.0105 0.8739 0.037 Uiso 1 1 calc R U . . .
C13 C -0.31737(16) 0.08139(17) 0.7501(2) 0.0371(6) Uani 1 1 d . . . . .
H13A H -0.3791 0.1179 0.7269 0.045 Uiso 1 1 calc R U . . .
C14 C 0.27493(14) -0.12328(13) 0.76389(16) 0.0195(4) Uani 1 1 d . . . . .
C15 C 0.28379(15) -0.16156(14) 0.86921(16) 0.0218(4) Uani 1 1 d . . . . .
C16 C 0.38203(16) -0.19531(14) 0.91067(17) 0.0256(4) Uani 1 1 d . . . . .
H16A H 0.3906 -0.2200 0.9831 0.031 Uiso 1 1 calc R U . . .
C17 C 0.46790(15) -0.19371(15) 0.84833(18) 0.0261(4) Uani 1 1 d . . . . .
C18 C 0.45548(15) -0.15464(14) 0.74372(17) 0.0255(5) Uani 1 1 d . . . . .
H18A H 0.5142 -0.1529 0.7013 0.031 Uiso 1 1 calc R U . . .
C19 C 0.35936(15) -0.11780(14) 0.69902(16) 0.0229(4) Uani 1 1 d . . . . .
C20 C 0.34743(17) -0.07081(17) 0.58728(17) 0.0320(5) Uani 1 1 d . . . . .
H20A H 0.2947 -0.1084 0.5415 0.048 Uiso 1 1 calc R U . . .
H20B H 0.4148 -0.0732 0.5547 0.048 Uiso 1 1 calc R U . . .
H20C H 0.3250 -0.0003 0.5931 0.048 Uiso 1 1 calc R U . . .
C21 C 0.19000(16) -0.16792(16) 0.93593(18) 0.0289(5) Uani 1 1 d . . . . .
H21A H 0.1554 -0.1019 0.9365 0.043 Uiso 1 1 calc R U . . .
H21D H 0.2132 -0.1876 1.0105 0.043 Uiso 1 1 calc R U . . .
H21B H 0.1406 -0.2184 0.9041 0.043 Uiso 1 1 calc R U . . .
C22 C 0.57217(17) -0.23671(18) 0.8938(2) 0.0378(6) Uani 1 1 d . . . . .
H22D H 0.6286 -0.2090 0.8535 0.057 Uiso 1 1 calc R U . . .
H22A H 0.5710 -0.3105 0.8866 0.057 Uiso 1 1 calc R U . . .
H22B H 0.5843 -0.2185 0.9707 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C3 1.784(2) . ?
Fe1 C1 1.785(2) . ?
Fe1 C2 1.7935(19) . ?
Fe1 C4 1.822(2) . ?
Fe1 C5 1.9976(19) . ?
O1 C1 1.147(2) . ?
O2 C2 1.150(2) . ?
O3 C3 1.154(2) . ?
O4 C4 1.144(2) . ?
N1 C5 1.370(2) . ?
N1 C7 1.389(3) . ?
N1 C8 1.459(2) . ?
N2 C5 1.365(2) . ?
N2 C6 1.390(2) . ?
N2 C14 1.446(2) . ?
N3 C9 1.338(2) . ?
N3 C13 1.344(3) . ?
C6 C7 1.339(3) . ?
C8 C9 1.515(3) . ?
C9 C10 1.384(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.375(3) . ?
C14 C15 1.392(3) . ?
C14 C19 1.397(3) . ?
C15 C16 1.392(3) . ?
C15 C21 1.511(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.389(3) . ?
C17 C22 1.516(3) . ?
C18 C19 1.395(3) . ?
C19 C20 1.510(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
C3 Fe1 C1 90.61(9) . . ?
C3 Fe1 C2 123.85(9) . . ?
C1 Fe1 C2 91.81(9) . . ?
C3 Fe1 C4 118.58(9) . . ?
C1 Fe1 C4 86.72(8) . . ?
C2 Fe1 C4 117.57(9) . . ?
C3 Fe1 C5 85.02(8) . . ?
C1 Fe1 C5 174.72(8) . . ?
C2 Fe1 C5 88.18(8) . . ?
C4 Fe1 C5 97.97(8) . . ?
C5 N1 C7 111.37(16) . . ?
C5 N1 C8 126.96(16) . . ?
C7 N1 C8 121.64(16) . . ?
C5 N2 C6 111.49(16) . . ?
C5 N2 C14 126.82(15) . . ?
C6 N2 C14 121.57(16) . . ?
C9 N3 C13 116.99(18) . . ?
O1 C1 Fe1 178.20(18) . . ?
O2 C2 Fe1 179.16(18) . . ?
O3 C3 Fe1 178.31(17) . . ?
O4 C4 Fe1 168.53(17) . . ?
N2 C5 N1 103.36(15) . . ?
N2 C5 Fe1 129.77(13) . . ?
N1 C5 Fe1 126.80(13) . . ?
C7 C6 N2 106.88(17) . . ?
C6 C7 N1 106.90(17) . . ?
N1 C8 C9 113.73(15) . . ?
N3 C9 C10 122.98(17) . . ?
N3 C9 C8 113.19(16) . . ?
C10 C9 C8 123.81(16) . . ?
C9 C10 C11 118.74(18) . . ?
C12 C11 C10 119.05(19) . . ?
C13 C12 C11 118.17(19) . . ?
N3 C13 C12 124.1(2) . . ?
C15 C14 C19 123.07(18) . . ?
C15 C14 N2 117.91(16) . . ?
C19 C14 N2 118.98(17) . . ?
C14 C15 C16 117.64(17) . . ?
C14 C15 C21 121.39(18) . . ?
C16 C15 C21 120.97(18) . . ?
C17 C16 C15 121.43(19) . . ?
C18 C17 C16 118.92(18) . . ?
C18 C17 C22 121.07(18) . . ?
C16 C17 C22 120.0(2) . . ?
C17 C18 C19 121.99(18) . . ?
C18 C19 C14 116.92(19) . . ?
C18 C19 C20 121.79(18) . . ?
C14 C19 C20 121.26(18) . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.057

