# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1452830'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-03-09 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            'C34 H39 Cl4 Fe N2'
_chemical_formula_weight         673.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.844(5)
_cell_length_b                   18.268(8)
_cell_length_c                   16.340(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.291(5)
_cell_angle_gamma                90
_cell_volume                     3441(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4081
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      21.05

_exptl_crystal_description       hexagonal
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             1404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.774
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21298
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.767
_diffrn_reflns_theta_max         27.573
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7920
_reflns_number_gt                4008
_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)+(0.1941P)²+7.2337P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7920
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1665
_refine_ls_R_factor_gt           0.1078
_refine_ls_wR_factor_ref         0.3658
_refine_ls_wR_factor_gt          0.3086
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_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
N1 N -0.8577(4) 0.0666(2) -0.2961(2) 0.0492(9) Uani 1 1 d . . . . .
H1A H -0.8038 0.0335 -0.2701 0.059 Uiso 1 1 d R U . . .
N2 N -0.7882(4) -0.0012(2) -0.1458(3) 0.0611(11) Uani 1 1 d . . . . .
C4 C -0.9367(5) 0.0757(3) -0.2372(3) 0.0571(13) Uani 1 1 d . . . . .
H4A H -0.9963 0.0376 -0.2501 0.069 Uiso 1 1 calc R U . . .
C6 C -0.8645(5) 0.0626(3) -0.1463(3) 0.0639(14) Uani 1 1 d . . . . .
H6A H -0.8144 0.1054 -0.1304 0.077 Uiso 1 1 calc R U . . .
C8 C -0.9165(5) 0.0299(3) -0.3776(3) 0.0538(12) Uani 1 1 d . . . . .
H8A H -0.8611 0.0271 -0.4130 0.065 Uiso 1 1 calc R U . . .
H8B H -0.9353 -0.0199 -0.3650 0.065 Uiso 1 1 calc R U . . .
C9 C -1.0234(5) 0.0649(3) -0.4267(3) 0.0576(12) Uani 1 1 d . . . . .
C10 C -0.7030(5) 0.1198(4) -0.3598(4) 0.0686(15) Uani 1 1 d . . . . .
C11 C -0.7884(6) 0.1340(3) -0.3069(4) 0.0709(16) Uani 1 1 d . . . . .
H11A H -0.8411 0.1724 -0.3328 0.085 Uiso 1 1 calc R U . . .
H11B H -0.7471 0.1512 -0.2520 0.085 Uiso 1 1 calc R U . . .
C12 C -0.7792(5) -0.1342(3) -0.1733(4) 0.0667(15) Uani 1 1 d . . . . .
C13 C -0.8506(6) -0.0734(3) -0.1542(4) 0.0729(16) Uani 1 1 d . . . . .
H13A H -0.8736 -0.0840 -0.1022 0.087 Uiso 1 1 calc R U . . .
H13B H -0.9205 -0.0698 -0.1986 0.087 Uiso 1 1 calc R U . . .
C14 C -1.0197(6) 0.1200(4) -0.4818(4) 0.0721(16) Uani 1 1 d . . . . .
H14A H -0.9481 0.1368 -0.4881 0.087 Uiso 1 1 calc R U . . .
C15 C -1.1322(6) 0.0386(4) -0.4211(4) 0.0721(16) Uani 1 1 d . . . . .
H15A H -1.1362 0.0004 -0.3842 0.087 Uiso 1 1 calc R U . . .
C16 C -1.0783(7) 0.1502(5) -0.1815(4) 0.095(2) Uani 1 1 d . . . . .
H16A H -1.1142 0.1981 -0.1829 0.114 Uiso 1 1 calc R U . . .
H16B H -1.1395 0.1146 -0.2006 0.114 Uiso 1 1 calc R U . . .
C17 C -0.7769(6) -0.2015(4) -0.1328(4) 0.0817(19) Uani 1 1 d . . . . .
H17A H -0.8207 -0.2087 -0.0930 0.098 Uiso 1 1 calc R U . . .
C18 C -0.9506(7) 0.0609(5) -0.0878(4) 0.091(2) Uani 1 1 d . . . . .
H18A H -1.0045 0.0206 -0.1038 0.109 Uiso 1 1 calc R U . . .
H18B H -0.9082 0.0530 -0.0302 0.109 Uiso 1 1 calc R U . . .
C20 C -0.6904(6) -0.0022(4) -0.0687(4) 0.0817(19) Uani 1 1 d . . . . .
H20A H -0.7221 0.0038 -0.0194 0.098 Uiso 1 1 calc R U . . .
H20B H -0.6523 -0.0495 -0.0646 0.098 Uiso 1 1 calc R U . . .
C21 C -0.7129(8) -0.1283(4) -0.2318(5) 0.098(2) Uani 1 1 d . . . . .
H21A H -0.7134 -0.0842 -0.2603 0.118 Uiso 1 1 calc R U . . .
C22 C -0.6173(6) 0.0694(5) -0.3400(5) 0.088(2) Uani 1 1 d . . . . .
H22A H -0.6096 0.0419 -0.2911 0.106 Uiso 1 1 calc R U . . .
C23 C -0.7107(7) 0.1612(5) -0.4337(5) 0.090(2) Uani 1 1 d . . . . .
H23A H -0.7678 0.1968 -0.4491 0.108 Uiso 1 1 calc R U . . .
C24 C -0.6319(10) 0.1482(7) -0.4829(6) 0.119(4) Uani 1 1 d . . . . .
H24A H -0.6371 0.1756 -0.5316 0.143 Uiso 1 1 calc R U . . .
C25 C -0.6415(8) -0.2490(4) -0.2055(6) 0.097(2) Uani 1 1 d . . . . .
H25A H -0.5914 -0.2864 -0.2129 0.116 Uiso 1 1 calc R U . . .
C26 C -1.1215(7) 0.1522(4) -0.5295(4) 0.087(2) Uani 1 1 d . . . . .
H26A H -1.1183 0.1915 -0.5649 0.104 Uiso 1 1 calc R U . . .
C27 C -1.2241(7) 0.1240(5) -0.5220(5) 0.092(2) Uani 1 1 d . . . . .
H27A H -1.2922 0.1436 -0.5546 0.110 Uiso 1 1 calc R U . . .
C28 C -0.5218(9) 0.0491(5) -0.1175(5) 0.108(3) Uani 1 1 d . . . . .
H28A H -0.5236 0.0075 -0.1506 0.129 Uiso 1 1 calc R U . . .
C29 C -0.7091(9) -0.2575(4) -0.1521(6) 0.105(3) Uani 1 1 d . . . . .
H29A H -0.7111 -0.3029 -0.1265 0.126 Uiso 1 1 calc R U . . .
C30 C -1.0182(8) 0.1329(5) -0.0935(4) 0.105(3) Uani 1 1 d . . . . .
H30A H -1.0749 0.1294 -0.0593 0.127 Uiso 1 1 calc R U . . .
H30B H -0.9651 0.1723 -0.0713 0.127 Uiso 1 1 calc R U . . .
C31 C -0.5498(9) 0.0982(8) -0.4629(7) 0.125(4) Uani 1 1 d . . . . .
H31A H -0.4986 0.0907 -0.4976 0.150 Uiso 1 1 calc R U . . .
C32 C -0.6455(8) -0.1848(5) -0.2500(6) 0.106(3) Uani 1 1 d . . . . .
H32A H -0.6038 -0.1796 -0.2914 0.127 Uiso 1 1 calc R U . . .
C33 C -0.4363(10) 0.1025(8) -0.1187(8) 0.150(5) Uani 1 1 d . . . . .
H33A H -0.3822 0.0976 -0.1515 0.180 Uiso 1 1 calc R U . . .
C34 C -0.5978(11) 0.1165(6) -0.0174(7) 0.163(6) Uani 1 1 d . . . . .
H34A H -0.6510 0.1215 0.0162 0.196 Uiso 1 1 calc R U . . .
C35 C -0.5108(17) 0.1716(8) -0.0150(13) 0.206(12) Uani 1 1 d . . . . .
H35A H -0.5037 0.2118 0.0207 0.248 Uiso 1 1 calc R U . . .
C36 C -1.2316(6) 0.0669(5) -0.4675(5) 0.089(2) Uani 1 1 d . . . . .
H36A H -1.3033 0.0487 -0.4631 0.107 Uiso 1 1 calc R U . . .
C37 C -0.5396(7) 0.0580(6) -0.3925(7) 0.116(3) Uani 1 1 d . . . . .
H37A H -0.4816 0.0228 -0.3785 0.140 Uiso 1 1 calc R U . . .
C38 C -0.4382(18) 0.1608(9) -0.0692(13) 0.193(10) Uani 1 1 d . . . . .
H38A H -0.3852 0.1979 -0.0717 0.231 Uiso 1 1 calc R U . . .
C39 C -0.6033(8) 0.0560(4) -0.0691(5) 0.099(3) Uani 1 1 d . . . . .
C40 C -0.9983(6) 0.1499(3) -0.2412(4) 0.0689(15) Uani 1 1 d . . . . .
H40A H -0.9413 0.1887 -0.2262 0.083 Uiso 1 1 calc R U . . .
H40B H -1.0426 0.1589 -0.2981 0.083 Uiso 1 1 calc R U . . .
Fe1 Fe -0.78666(10) 0.36005(6) -0.25572(7) 0.0875(4) Uani 1 1 d . . . . .
Cl1 Cl -0.64272(18) 0.28720(15) -0.20773(16) 0.1203(9) Uani 1 1 d . . . . .
Cl2 Cl -0.9114(2) 0.34836(12) -0.17415(13) 0.1004(7) Uani 1 1 d . . . . .
Cl3 Cl -0.8798(3) 0.32649(16) -0.38181(13) 0.1266(9) Uani 1 1 d . . . . .
Cl4 Cl -0.7343(4) 0.47198(17) -0.2542(3) 0.1894(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.497(6) . ?
N1 C11 1.513(7) . ?
N1 C8 1.510(6) . ?
N1 H1A 0.9101 . ?
N2 C6 1.474(7) . ?
N2 C13 1.502(8) . ?
N2 C20 1.503(7) . ?
C4 C40 1.534(8) . ?
C4 C6 1.552(7) . ?
C4 H4A 0.9800 . ?
C6 C18 1.550(9) . ?
C6 H6A 0.9800 . ?
C8 C9 1.479(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.357(8) . ?
C9 C15 1.399(9) . ?
C10 C22 1.353(10) . ?
C10 C23 1.410(9) . ?
C10 C11 1.496(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C21 1.373(10) . ?
C12 C17 1.394(9) . ?
C12 C13 1.473(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C26 1.405(10) . ?
C14 H14A 0.9300 . ?
C15 C36 1.349(10) . ?
C15 H15A 0.9300 . ?
C16 C30 1.485(10) . ?
C16 C40 1.508(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C29 1.380(11) . ?
C17 H17A 0.9300 . ?
C18 C30 1.532(11) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 C39 1.482(11) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C32 1.378(11) . ?
C21 H21A 0.9300 . ?
C22 C37 1.411(12) . ?
C22 H22A 0.9300 . ?
C23 C24 1.385(13) . ?
C23 H23A 0.9300 . ?
C24 C31 1.321(15) . ?
C24 H24A 0.9300 . ?
C25 C29 1.323(12) . ?
C25 C32 1.376(12) . ?
C25 H25A 0.9300 . ?
C26 C27 1.351(11) . ?
C26 H26A 0.9300 . ?
C27 C36 1.386(11) . ?
C27 H27A 0.9300 . ?
C28 C39 1.388(13) . ?
C28 C33 1.409(14) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9300 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C37 1.347(14) . ?
C31 H31A 0.9300 . ?
C32 H32A 0.9300 . ?
C33 C38 1.34(2) . ?
C33 H33A 0.9300 . ?
C34 C39 1.384(12) . ?
C34 C35 1.43(2) . ?
C34 H34A 0.9300 . ?
C35 C38 1.38(3) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?
C37 H37A 0.9300 . ?
C38 H38A 0.9300 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
Fe1 Cl4 2.135(3) . ?
Fe1 Cl1 2.163(3) . ?
Fe1 Cl3 2.189(3) . ?
Fe1 Cl2 2.216(2) . ?

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
C4 N1 C11 114.9(4) . . ?
C4 N1 C8 112.8(4) . . ?
C11 N1 C8 114.2(4) . . ?
C4 N1 H1A 104.4 . . ?
C11 N1 H1A 104.7 . . ?
C8 N1 H1A 104.4 . . ?
C6 N2 C13 113.9(5) . . ?
C6 N2 C20 111.5(5) . . ?
C13 N2 C20 109.5(4) . . ?
N1 C4 C40 115.6(4) . . ?
N1 C4 C6 108.1(4) . . ?
C40 C4 C6 109.3(4) . . ?
N1 C4 H4A 107.9 . . ?
C40 C4 H4A 107.9 . . ?
C6 C4 H4A 107.9 . . ?
N2 C6 C4 109.2(4) . . ?
N2 C6 C18 118.1(5) . . ?
C4 C6 C18 107.3(5) . . ?
N2 C6 H6A 107.2 . . ?
C4 C6 H6A 107.2 . . ?
C18 C6 H6A 107.2 . . ?
C9 C8 N1 116.8(4) . . ?
C9 C8 H8A 108.1 . . ?
N1 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
N1 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C14 C9 C15 118.0(6) . . ?
C14 C9 C8 121.7(5) . . ?
C15 C9 C8 120.2(5) . . ?
C22 C10 C23 117.9(7) . . ?
C22 C10 C11 123.3(6) . . ?
C23 C10 C11 118.8(6) . . ?
C10 C11 N1 112.6(5) . . ?
C10 C11 H11A 109.1 . . ?
N1 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
N1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C21 C12 C17 116.6(7) . . ?
C21 C12 C13 122.4(6) . . ?
C17 C12 C13 121.0(6) . . ?
C12 C13 N2 112.8(5) . . ?
C12 C13 H13A 109.0 . . ?
N2 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
N2 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C9 C14 C26 121.6(6) . . ?
C9 C14 H14A 119.2 . . ?
C26 C14 H14A 119.2 . . ?
C36 C15 C9 122.0(6) . . ?
C36 C15 H15A 119.0 . . ?
C9 C15 H15A 119.0 . . ?
C30 C16 C40 113.2(6) . . ?
C30 C16 H16A 108.9 . . ?
C40 C16 H16A 108.9 . . ?
C30 C16 H16B 108.9 . . ?
C40 C16 H16B 108.9 . . ?
H16A C16 H16B 107.8 . . ?
C29 C17 C12 119.6(7) . . ?
C29 C17 H17A 120.2 . . ?
C12 C17 H17A 120.2 . . ?
C30 C18 C6 110.7(6) . . ?
C30 C18 H18A 109.5 . . ?
C6 C18 H18A 109.5 . . ?
C30 C18 H18B 109.5 . . ?
C6 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C39 C20 N2 113.0(5) . . ?
C39 C20 H20A 109.0 . . ?
N2 C20 H20A 109.0 . . ?
C39 C20 H20B 109.0 . . ?
N2 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C12 C21 C32 122.9(8) . . ?
C12 C21 H21A 118.6 . . ?
C32 C21 H21A 118.6 . . ?
C10 C22 C37 120.9(8) . . ?
C10 C22 H22A 119.6 . . ?
C37 C22 H22A 119.6 . . ?
C24 C23 C10 119.0(9) . . ?
C24 C23 H23A 120.5 . . ?
C10 C23 H23A 120.5 . . ?
C31 C24 C23 122.1(9) . . ?
C31 C24 H24A 118.9 . . ?
C23 C24 H24A 118.9 . . ?
C29 C25 C32 119.7(8) . . ?
C29 C25 H25A 120.1 . . ?
C32 C25 H25A 120.1 . . ?
C27 C26 C14 117.7(7) . . ?
C27 C26 H26A 121.1 . . ?
C14 C26 H26A 121.1 . . ?
C26 C27 C36 122.4(7) . . ?
C26 C27 H27A 118.8 . . ?
C36 C27 H27A 118.8 . . ?
C39 C28 C33 122.7(11) . . ?
C39 C28 H28A 118.6 . . ?
C33 C28 H28A 118.6 . . ?
C25 C29 C17 122.4(7) . . ?
C25 C29 H29A 118.8 . . ?
C17 C29 H29A 118.8 . . ?
C16 C30 C18 111.7(5) . . ?
C16 C30 H30A 109.3 . . ?
C18 C30 H30A 109.3 . . ?
C16 C30 H30B 109.3 . . ?
C18 C30 H30B 109.3 . . ?
H30A C30 H30B 107.9 . . ?
C24 C31 C37 120.4(10) . . ?
C24 C31 H31A 119.8 . . ?
C37 C31 H31A 119.8 . . ?
C21 C32 C25 118.5(9) . . ?
C21 C32 H32A 120.8 . . ?
C25 C32 H32A 120.8 . . ?
C38 C33 C28 115.6(16) . . ?
C38 C33 H33A 122.2 . . ?
C28 C33 H33A 122.2 . . ?
C39 C34 C35 120.7(15) . . ?
C39 C34 H34A 119.7 . . ?
C35 C34 H34A 119.7 . . ?
C38 C35 C34 115.5(16) . . ?
C38 C35 H35A 122.2 . . ?
C34 C35 H35A 122.2 . . ?
C15 C36 C27 118.2(7) . . ?
C15 C36 H36A 120.9 . . ?
C27 C36 H36A 120.9 . . ?
C31 C37 C22 119.7(10) . . ?
C31 C37 H37A 120.1 . . ?
C22 C37 H37A 120.1 . . ?
C33 C38 C35 126.7(19) . . ?
C33 C38 H38A 116.7 . . ?
C35 C38 H38A 116.7 . . ?
C28 C39 C34 118.6(11) . . ?
C28 C39 C20 120.9(7) . . ?
C34 C39 C20 120.4(12) . . ?
C16 C40 C4 109.8(5) . . ?
C16 C40 H40A 109.7 . . ?
C4 C40 H40A 109.7 . . ?
C16 C40 H40B 109.7 . . ?
C4 C40 H40B 109.7 . . ?
H40A C40 H40B 108.2 . . ?
Cl4 Fe1 Cl1 112.48(16) . . ?
Cl4 Fe1 Cl3 111.17(16) . . ?
Cl1 Fe1 Cl3 110.70(10) . . ?
Cl4 Fe1 Cl2 108.52(12) . . ?
Cl1 Fe1 Cl2 107.54(11) . . ?
Cl3 Fe1 Cl2 106.14(11) . . ?

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
C11 N1 C4 C40 38.5(6) . . . . ?
C8 N1 C4 C40 -94.7(5) . . . . ?
C11 N1 C4 C6 -84.2(5) . . . . ?
C8 N1 C4 C6 142.5(4) . . . . ?
C13 N2 C6 C4 -74.1(6) . . . . ?
C20 N2 C6 C4 161.3(5) . . . . ?
C13 N2 C6 C18 48.8(7) . . . . ?
C20 N2 C6 C18 -75.8(7) . . . . ?
N1 C4 C6 N2 -42.7(6) . . . . ?
C40 C4 C6 N2 -169.2(5) . . . . ?
N1 C4 C6 C18 -171.8(5) . . . . ?
C40 C4 C6 C18 61.6(7) . . . . ?
C4 N1 C8 C9 56.3(6) . . . . ?
C11 N1 C8 C9 -77.2(6) . . . . ?
N1 C8 C9 C14 85.5(6) . . . . ?
N1 C8 C9 C15 -98.4(6) . . . . ?
C22 C10 C11 N1 -59.3(8) . . . . ?
C23 C10 C11 N1 121.5(6) . . . . ?
C4 N1 C11 C10 174.6(4) . . . . ?
C8 N1 C11 C10 -52.9(6) . . . . ?
C21 C12 C13 N2 -43.8(8) . . . . ?
C17 C12 C13 N2 136.7(6) . . . . ?
C6 N2 C13 C12 166.6(4) . . . . ?
C20 N2 C13 C12 -67.7(6) . . . . ?
C15 C9 C14 C26 2.6(9) . . . . ?
C8 C9 C14 C26 178.9(6) . . . . ?
C14 C9 C15 C36 -0.9(9) . . . . ?
C8 C9 C15 C36 -177.1(6) . . . . ?
C21 C12 C17 C29 0.5(10) . . . . ?
C13 C12 C17 C29 -180.0(7) . . . . ?
N2 C6 C18 C30 177.2(6) . . . . ?
C4 C6 C18 C30 -58.9(7) . . . . ?
C6 N2 C20 C39 -70.7(8) . . . . ?
C13 N2 C20 C39 162.3(6) . . . . ?
C17 C12 C21 C32 -0.7(12) . . . . ?
C13 C12 C21 C32 179.8(7) . . . . ?
C23 C10 C22 C37 -1.1(10) . . . . ?
C11 C10 C22 C37 179.6(7) . . . . ?
C22 C10 C23 C24 0.7(10) . . . . ?
C11 C10 C23 C24 -179.9(6) . . . . ?
C10 C23 C24 C31 0.0(13) . . . . ?
C9 C14 C26 C27 -3.3(11) . . . . ?
C14 C26 C27 C36 2.2(12) . . . . ?
C32 C25 C29 C17 -6.2(13) . . . . ?
C12 C17 C29 C25 3.0(12) . . . . ?
C40 C16 C30 C18 -53.7(10) . . . . ?
C6 C18 C30 C16 55.3(10) . . . . ?
C23 C24 C31 C37 -0.4(16) . . . . ?
C12 C21 C32 C25 -2.4(14) . . . . ?
C29 C25 C32 C21 5.8(13) . . . . ?
C39 C28 C33 C38 0.3(13) . . . . ?
C39 C34 C35 C38 2.2(19) . . . . ?
C9 C15 C36 C27 -0.2(11) . . . . ?
C26 C27 C36 C15 -0.5(12) . . . . ?
C24 C31 C37 C22 0.1(15) . . . . ?
C10 C22 C37 C31 0.7(13) . . . . ?
C28 C33 C38 C35 4(2) . . . . ?
C34 C35 C38 C33 -5(3) . . . . ?
C33 C28 C39 C34 -2.5(11) . . . . ?
C33 C28 C39 C20 -178.9(6) . . . . ?
C35 C34 C39 C28 1.1(12) . . . . ?
C35 C34 C39 C20 177.6(9) . . . . ?
N2 C20 C39 C28 -77.2(8) . . . . ?
N2 C20 C39 C34 106.4(7) . . . . ?
C30 C16 C40 C4 56.2(8) . . . . ?
N1 C4 C40 C16 177.6(5) . . . . ?
C6 C4 C40 C16 -60.2(7) . . . . ?

_refine_diff_density_max         2.000
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_beta_2
_database_code_depnum_ccdc_archive 'CCDC 1452831'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H39 Cl4 Fe N2'
_chemical_formula_weight         672.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   19.428(3)
_cell_length_b                   14.4576(15)
_cell_length_c                   11.9160(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3347.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2006
_cell_measurement_theta_min      8.36
_cell_measurement_theta_max      65.31

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    6.739
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5522
_exptl_absorpt_correction_T_max  0.7743
_exptl_absorpt_process_details   Experimental

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10182
_diffrn_reflns_av_R_equivalents  0.1551
_diffrn_reflns_av_sigmaI/netI    0.1765
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         8.36
_diffrn_reflns_theta_max         66.37
_reflns_number_total             4539
_reflns_number_gt                2279
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1997P)²+2.6709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.86(2)
_refine_ls_number_reflns         4539
_refine_ls_number_parameters     370
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2161
_refine_ls_R_factor_gt           0.1086
_refine_ls_wR_factor_ref         0.3592
_refine_ls_wR_factor_gt          0.2930
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.07202(14) 0.65524(14) 0.2537(3) 0.0743(8) Uani 1 1 d . . .
Cl4 Cl -0.0010(3) 0.7692(3) 0.2331(4) 0.0904(14) Uani 1 1 d . . .
Cl2 Cl 0.0441(3) 0.5384(3) 0.1498(5) 0.0995(16) Uani 1 1 d . . .
Cl3 Cl 0.0673(3) 0.6077(3) 0.4289(4) 0.0927(15) Uani 1 1 d . . .
C1 C 0.0744(8) -0.1438(9) 0.5125(15) 0.065(4) Uani 1 1 d . . .
H1 H 0.0913 -0.1860 0.4579 0.078 Uiso 1 1 calc R . .
C6 C 0.0794(7) -0.0481(9) 0.4941(15) 0.066(4) Uani 1 1 d . . .
C4 C 0.0277(9) -0.0231(13) 0.6798(17) 0.078(5) Uani 1 1 d . . .
H4 H 0.0106 0.0182 0.7352 0.094 Uiso 1 1 calc R . .
C5 C 0.0560(9) 0.0116(10) 0.5820(18) 0.078(5) Uani 1 1 d . . .
H5 H 0.0600 0.0766 0.5729 0.093 Uiso 1 1 calc R . .
C2 C 0.0443(9) -0.1769(12) 0.6123(15) 0.071(4) Uani 1 1 d . . .
H2 H 0.0376 -0.2415 0.6214 0.085 Uiso 1 1 calc R . .
C3 C 0.0242(9) -0.1176(13) 0.6975(17) 0.081(5) Uani 1 1 d . . .
H3 H 0.0082 -0.1414 0.7671 0.097 Uiso 1 1 calc R . .
C7 C 0.1104(8) -0.0112(10) 0.3894(14) 0.069(4) Uani 1 1 d . . .
H7A H 0.0826 0.0426 0.3651 0.082 Uiso 1 1 calc R . .
H7B H 0.1059 -0.0592 0.3306 0.082 Uiso 1 1 calc R . .
N1 N 0.1841(6) 0.0182(7) 0.3937(10) 0.057(3) Uani 1 1 d . . .
C10 C 0.2961(9) -0.1785(12) 0.5246(18) 0.088(6) Uani 1 1 d . . .
H10A H 0.2694 -0.2311 0.4938 0.106 Uiso 1 1 calc R . .
H10B H 0.3100 -0.1945 0.6021 0.106 Uiso 1 1 calc R . .
C8 C 0.2330(9) -0.0624(9) 0.4067(14) 0.066(4) Uani 1 1 d . . .
H8 H 0.2112 -0.1168 0.3689 0.079 Uiso 1 1 calc R . .
C9 C 0.2511(9) -0.0926(10) 0.5267(13) 0.068(4) Uani 1 1 d . . .
H9A H 0.2758 -0.0420 0.5655 0.081 Uiso 1 1 calc R . .
H9B H 0.2083 -0.1058 0.5689 0.081 Uiso 1 1 calc R . .
C12 C 0.3447(9) -0.1284(12) 0.3352(15) 0.069(4) Uani 1 1 d . . .
H12A H 0.3196 -0.1771 0.2934 0.083 Uiso 1 1 calc R . .
H12B H 0.3874 -0.1137 0.2936 0.083 Uiso 1 1 calc R . .
C11 C 0.3623(10) -0.1627(11) 0.4506(18) 0.085(5) Uani 1 1 d . . .
H11A H 0.3926 -0.1171 0.4881 0.102 Uiso 1 1 calc R . .
H11B H 0.3880 -0.2216 0.4443 0.102 Uiso 1 1 calc R . .
C13 C 0.2999(8) -0.0419(10) 0.3444(13) 0.059(4) Uani 1 1 d . . .
H13 H 0.3260 0.0040 0.3906 0.071 Uiso 1 1 calc R . .
N2 N 0.2840(6) 0.0039(7) 0.2344(11) 0.061(3) Uani 1 1 d . . .
C14 C 0.2552(9) -0.0609(9) 0.1434(15) 0.069(4) Uani 1 1 d . . .
H14A H 0.2934 -0.0974 0.1109 0.083 Uiso 1 1 calc R . .
H14B H 0.2224 -0.1047 0.1783 0.083 Uiso 1 1 calc R . .
C15 C 0.2201(9) -0.0104(10) 0.0531(15) 0.067(4) Uani 1 1 d . . .
C18 C 0.1481(11) 0.0843(11) -0.1161(14) 0.070(5) Uani 1 1 d . . .
H18 H 0.1243 0.1163 -0.1739 0.084 Uiso 1 1 calc R . .
C17 C 0.1190(11) 0.0706(11) -0.0141(17) 0.077(5) Uani 1 1 d . . .
H17 H 0.0741 0.0942 -0.0011 0.092 Uiso 1 1 calc R . .
C16 C 0.1512(9) 0.0249(11) 0.0699(15) 0.073(5) Uani 1 1 d . . .
H16 H 0.1286 0.0160 0.1398 0.087 Uiso 1 1 calc R . .
C19 C 0.2161(12) 0.0489(14) -0.1338(15) 0.084(6) Uani 1 1 d . . .
H19 H 0.2376 0.0565 -0.2048 0.101 Uiso 1 1 calc R . .
C20 C 0.2498(9) 0.0050(11) -0.0509(15) 0.068(4) Uani 1 1 d . . .
H20 H 0.2953 -0.0161 -0.0641 0.082 Uiso 1 1 calc R . .
C27 C 0.3136(9) 0.2208(11) 0.2579(17) 0.077(5) Uani 1 1 d . . .
H27 H 0.2769 0.2199 0.2053 0.092 Uiso 1 1 calc R . .
C22 C 0.3546(8) 0.1426(9) 0.2598(14) 0.063(4) Uani 1 1 d . . .
C21 C 0.3445(8) 0.0614(10) 0.1909(14) 0.067(4) Uani 1 1 d . . .
H21A H 0.3869 0.0234 0.1916 0.081 Uiso 1 1 calc R . .
H21B H 0.3355 0.0805 0.1125 0.081 Uiso 1 1 calc R . .
C26 C 0.3185(12) 0.2932(12) 0.316(2) 0.091(6) Uani 1 1 d . . .
H26 H 0.2897 0.3451 0.3028 0.109 Uiso 1 1 calc R . .
C23 C 0.4049(9) 0.1448(12) 0.3455(16) 0.070(4) Uani 1 1 d . . .
H23 H 0.4339 0.0925 0.3548 0.084 Uiso 1 1 calc R . .
C24 C 0.4137(9) 0.2189(12) 0.4160(16) 0.081(5) Uani 1 1 d . . .
H24 H 0.4492 0.2185 0.4708 0.097 Uiso 1 1 calc R . .
C25 C 0.3698(14) 0.2949(14) 0.406(2) 0.115(8) Uani 1 1 d . . .
H25 H 0.3732 0.3460 0.4558 0.138 Uiso 1 1 calc R . .
C30 C 0.1441(9) 0.2072(11) 0.3287(14) 0.069(4) Uani 1 1 d . . .
H30 H 0.1577 0.1665 0.2702 0.083 Uiso 1 1 calc R . .
C31 C 0.1100(10) 0.2886(11) 0.3005(19) 0.088(6) Uani 1 1 d . . .
H31 H 0.1001 0.3037 0.2246 0.106 Uiso 1 1 calc R . .
C29 C 0.1588(8) 0.1836(9) 0.4363(15) 0.064(4) Uani 1 1 d . . .
C28 C 0.1978(8) 0.0941(9) 0.4687(14) 0.061(4) Uani 1 1 d . . .
H28A H 0.2478 0.1068 0.4689 0.074 Uiso 1 1 calc R . .
H28B H 0.1844 0.0758 0.5458 0.074 Uiso 1 1 calc R . .
C32 C 0.0911(10) 0.3471(11) 0.388(2) 0.086(6) Uani 1 1 d . . .
H32 H 0.0699 0.4047 0.3713 0.103 Uiso 1 1 calc R . .
C34 C 0.1357(9) 0.2408(11) 0.5245(17) 0.083(6) Uani 1 1 d . . .
H34 H 0.1425 0.2240 0.6008 0.099 Uiso 1 1 calc R . .
C33 C 0.1021(9) 0.3238(12) 0.495(2) 0.083(6) Uani 1 1 d . . .
H33 H 0.0869 0.3642 0.5531 0.100 Uiso 1 1 calc R . .
Cl1 Cl 0.1748(3) 0.7090(4) 0.2158(6) 0.115(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 Cl2 2.163(5) . ?
Fe1 Cl4 2.187(5) . ?
Fe1 Cl1 2.189(6) . ?
Fe1 Cl3 2.199(5) . ?
C1 C6 1.404(19) . ?
C1 C2 1.41(2) . ?
C6 C5 1.43(2) . ?
C6 C7 1.48(2) . ?
C4 C3 1.38(2) . ?
C4 C5 1.38(3) . ?
C2 C3 1.39(3) . ?
C7 N1 1.495(19) . ?
N1 C28 1.440(17) . ?
N1 C8 1.513(18) . ?
C10 C9 1.52(2) . ?
C10 C11 1.58(3) . ?
C8 C13 1.53(2) . ?
C8 C9 1.54(2) . ?
C12 C11 1.50(2) . ?
C12 C13 1.53(2) . ?
C13 N2 1.499(19) . ?
N2 C21 1.531(18) . ?
N2 C14 1.54(2) . ?
C14 C15 1.47(2) . ?
C15 C20 1.38(2) . ?
C15 C16 1.45(2) . ?
C18 C17 1.35(2) . ?
C18 C19 1.43(3) . ?
C17 C16 1.35(2) . ?
C19 C20 1.34(2) . ?
C27 C26 1.26(3) . ?
C27 C22 1.38(2) . ?
C22 C23 1.41(2) . ?
C22 C21 1.45(2) . ?
C26 C25 1.46(3) . ?
C23 C24 1.37(2) . ?
C24 C25 1.40(3) . ?
C30 C29 1.36(2) . ?
C30 C31 1.39(2) . ?
C31 C32 1.39(3) . ?
C29 C34 1.41(2) . ?
C29 C28 1.549(19) . ?
C32 C33 1.34(3) . ?
C34 C33 1.41(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
Cl2 Fe1 Cl4 111.2(2) . . ?
Cl2 Fe1 Cl1 112.8(3) . . ?
Cl4 Fe1 Cl1 107.5(2) . . ?
Cl2 Fe1 Cl3 106.8(2) . . ?
Cl4 Fe1 Cl3 108.4(2) . . ?
Cl1 Fe1 Cl3 110.2(2) . . ?
C6 C1 C2 119.7(15) . . ?
C1 C6 C5 117.2(16) . . ?
C1 C6 C7 120.9(15) . . ?
C5 C6 C7 121.9(13) . . ?
C3 C4 C5 120.4(18) . . ?
C4 C5 C6 121.7(15) . . ?
C3 C2 C1 121.7(16) . . ?
C4 C3 C2 119.0(18) . . ?
C6 C7 N1 117.5(13) . . ?
C28 N1 C7 114.5(12) . . ?
C28 N1 C8 114.0(12) . . ?
C7 N1 C8 112.7(11) . . ?
C9 C10 C11 111.1(13) . . ?
N1 C8 C13 109.6(11) . . ?
N1 C8 C9 117.3(12) . . ?
C13 C8 C9 108.3(14) . . ?
C10 C9 C8 110.4(14) . . ?
C11 C12 C13 109.6(15) . . ?
C12 C11 C10 111.9(14) . . ?
N2 C13 C8 109.7(12) . . ?
N2 C13 C12 114.6(14) . . ?
C8 C13 C12 111.1(12) . . ?
C13 N2 C21 112.2(11) . . ?
C13 N2 C14 115.0(10) . . ?
C21 N2 C14 111.8(12) . . ?
C15 C14 N2 112.5(11) . . ?
C20 C15 C16 116.9(16) . . ?
C20 C15 C14 122.9(16) . . ?
C16 C15 C14 120.2(16) . . ?
C17 C18 C19 117.7(15) . . ?
C16 C17 C18 122.8(19) . . ?
C17 C16 C15 119.8(17) . . ?
C20 C19 C18 120.6(17) . . ?
C19 C20 C15 122.1(17) . . ?
C26 C27 C22 129(2) . . ?
C27 C22 C23 113.0(16) . . ?
C27 C22 C21 125.2(16) . . ?
C23 C22 C21 121.5(14) . . ?
C22 C21 N2 110.7(12) . . ?
C27 C26 C25 118.0(19) . . ?
C24 C23 C22 123.2(17) . . ?
C23 C24 C25 119(2) . . ?
C24 C25 C26 118(2) . . ?
C29 C30 C31 122.7(17) . . ?
C32 C31 C30 117(2) . . ?
C30 C29 C34 119.3(15) . . ?
C30 C29 C28 123.2(14) . . ?
C34 C29 C28 117.4(15) . . ?
N1 C28 C29 113.0(13) . . ?
C33 C32 C31 121.3(17) . . ?
C33 C34 C29 117.6(18) . . ?
C32 C33 C34 121.6(16) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        66.37
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.106
####################################################################### 
# 
# 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 1452832'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H38 N2'
_chemical_formula_weight         474.66

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   17.33(3)
_cell_length_b                   11.523(17)
_cell_length_c                   14.65(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.739(17)
_cell_angle_gamma                90.00
_cell_volume                     2802(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8177
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3185
_reflns_number_gt                1893
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0805P)²+0.2354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3185
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.07600(6) 0.47642(10) -0.32313(9) 0.0512(3) Uani 1 1 d . . .
C1 C -0.04583(8) 0.58646(12) -0.27496(11) 0.0501(4) Uani 1 1 d . . .
H1 H -0.0721 0.5960 -0.2245 0.060 Uiso 1 1 calc R . .
C2 C -0.04497(10) 0.45240(13) -0.40499(12) 0.0590(4) Uani 1 1 d . . .
H2A H 0.0125 0.4680 -0.3868 0.071 Uiso 1 1 calc R . .
H2B H -0.0708 0.5044 -0.4569 0.071 Uiso 1 1 calc R . .
C3 C -0.20113(8) 0.47216(14) -0.27147(12) 0.0572(4) Uani 1 1 d . . .
C4 C -0.05947(9) 0.32955(14) -0.43901(12) 0.0577(4) Uani 1 1 d . . .
C5 C -0.16449(8) 0.47023(15) -0.35304(12) 0.0628(4) Uani 1 1 d . . .
H5A H -0.1810 0.3995 -0.3893 0.075 Uiso 1 1 calc R . .
H5B H -0.1856 0.5352 -0.3949 0.075 Uiso 1 1 calc R . .
C6 C -0.06618(10) 0.69585(13) -0.33754(13) 0.0669(5) Uani 1 1 d . . .
H6A H -0.0371 0.6938 -0.3851 0.080 Uiso 1 1 calc R . .
H6B H -0.1234 0.6966 -0.3706 0.080 Uiso 1 1 calc R . .
C7 C -0.02036(11) 0.23947(16) -0.38200(14) 0.0735(5) Uani 1 1 d . . .
H7A H 0.0148 0.2555 -0.3222 0.088 Uiso 1 1 calc R . .
C8 C -0.18371(10) 0.38750(15) -0.20293(14) 0.0725(5) Uani 1 1 d . . .
H8A H -0.1471 0.3295 -0.2055 0.087 Uiso 1 1 calc R . .
C9 C -0.04405(11) 0.80596(14) -0.27838(16) 0.0833(6) Uani 1 1 d . . .
H9A H -0.0551 0.8730 -0.3202 0.100 Uiso 1 1 calc R . .
H9B H -0.0770 0.8120 -0.2352 0.100 Uiso 1 1 calc R . .
C10 C -0.25601(10) 0.55670(16) -0.26493(15) 0.0785(6) Uani 1 1 d . . .
H10A H -0.2686 0.6156 -0.3102 0.094 Uiso 1 1 calc R . .
C11 C -0.11140(11) 0.30310(18) -0.52721(14) 0.0798(6) Uani 1 1 d . . .
H11A H -0.1379 0.3626 -0.5668 0.096 Uiso 1 1 calc R . .
C12 C -0.21992(13) 0.3869(2) -0.12944(16) 0.0902(6) Uani 1 1 d . . .
H12A H -0.2074 0.3290 -0.0832 0.108 Uiso 1 1 calc R . .
C13 C -0.27391(12) 0.4717(2) -0.12573(18) 0.0976(8) Uani 1 1 d . . .
H13A H -0.2981 0.4717 -0.0767 0.117 Uiso 1 1 calc R . .
C14 C -0.08525(19) 0.1019(2) -0.5011(3) 0.1162(10) Uani 1 1 d . . .
H14A H -0.0937 0.0256 -0.5221 0.139 Uiso 1 1 calc R . .
C15 C -0.29239(13) 0.5556(2) -0.19303(19) 0.0996(7) Uani 1 1 d . . .
H15A H -0.3298 0.6126 -0.1907 0.119 Uiso 1 1 calc R . .
C16 C -0.12447(15) 0.1897(3) -0.5574(2) 0.1086(9) Uani 1 1 d . . .
H16A H -0.1603 0.1731 -0.6166 0.130 Uiso 1 1 calc R . .
C17 C -0.03294(15) 0.12588(18) -0.4128(2) 0.1018(8) Uani 1 1 d . . .
H17A H -0.0062 0.0658 -0.3741 0.122 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.472(2) . ?
N1 C2 1.475(2) . ?
N1 C5 1.470(3) . ?
C1 C6 1.539(3) . ?
C1 C1 1.546(4) 2_554 ?
C1 H1 0.9800 . ?
C2 C4 1.498(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.370(3) . ?
C3 C10 1.384(3) . ?
C3 C5 1.506(3) . ?
C4 C11 1.379(3) . ?
C4 C7 1.381(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.522(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C17 1.381(3) . ?
C7 H7A 0.9300 . ?
C8 C12 1.394(3) . ?
C8 H8A 0.9300 . ?
C9 C9 1.514(4) 2_554 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.375(3) . ?
C10 H10A 0.9300 . ?
C11 C16 1.378(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.365(3) . ?
C12 H12A 0.9300 . ?
C13 C15 1.352(3) . ?
C13 H13A 0.9300 . ?
C14 C16 1.357(4) . ?
C14 C17 1.377(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?

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 N1 C2 112.90(12) . . ?
C1 N1 C5 112.37(11) . . ?
C2 N1 C5 109.99(14) . . ?
N1 C1 C6 115.54(16) . . ?
N1 C1 C1 113.67(8) . 2_554 ?
C6 C1 C1 108.05(10) . 2_554 ?
N1 C1 H1 106.3 . . ?
C6 C1 H1 106.3 . . ?
C1 C1 H1 106.3 2_554 . ?
N1 C2 C4 112.48(12) . . ?
N1 C2 H2A 109.1 . . ?
C4 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C4 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C8 C3 C10 117.48(18) . . ?
C8 C3 C5 121.11(16) . . ?
C10 C3 C5 121.36(18) . . ?
C11 C4 C7 118.33(18) . . ?
C11 C4 C2 121.48(16) . . ?
C7 C4 C2 120.19(17) . . ?
N1 C5 C3 113.88(15) . . ?
N1 C5 H5A 108.8 . . ?
C3 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
C3 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C9 C6 C1 111.51(18) . . ?
C9 C6 H6A 109.3 . . ?
C1 C6 H6A 109.3 . . ?
C9 C6 H6B 109.3 . . ?
C1 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C17 C7 C4 120.7(2) . . ?
C17 C7 H7A 119.6 . . ?
C4 C7 H7A 119.6 . . ?
C3 C8 C12 121.1(2) . . ?
C3 C8 H8A 119.4 . . ?
C12 C8 H8A 119.4 . . ?
C9 C9 C6 111.20(12) 2_554 . ?
C9 C9 H9A 109.4 2_554 . ?
C6 C9 H9A 109.4 . . ?
C9 C9 H9B 109.4 2_554 . ?
C6 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C15 C10 C3 121.5(2) . . ?
C15 C10 H10A 119.3 . . ?
C3 C10 H10A 119.3 . . ?
C4 C11 C16 120.9(2) . . ?
C4 C11 H11A 119.6 . . ?
C16 C11 H11A 119.6 . . ?
C13 C12 C8 119.6(2) . . ?
C13 C12 H12A 120.2 . . ?
C8 C12 H12A 120.2 . . ?
C15 C13 C12 120.3(2) . . ?
C15 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C16 C14 C17 120.1(2) . . ?
C16 C14 H14A 120.0 . . ?
C17 C14 H14A 120.0 . . ?
C13 C15 C10 120.1(2) . . ?
C13 C15 H15A 120.0 . . ?
C10 C15 H15A 120.0 . . ?
C14 C16 C11 120.3(2) . . ?
C14 C16 H16A 119.9 . . ?
C11 C16 H16A 119.9 . . ?
C14 C17 C7 119.7(2) . . ?
C14 C17 H17A 120.1 . . ?
C7 C17 H17A 120.1 . . ?

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
C2 N1 C1 C6 59.33(18) . . . . ?
C5 N1 C1 C6 -65.77(16) . . . . ?
C2 N1 C1 C1 -66.4(2) . . . 2_554 ?
C5 N1 C1 C1 168.46(15) . . . 2_554 ?
C1 N1 C2 C4 166.40(12) . . . . ?
C5 N1 C2 C4 -67.21(16) . . . . ?
N1 C2 C4 C11 113.3(2) . . . . ?
N1 C2 C4 C7 -67.0(2) . . . . ?
C1 N1 C5 C3 -63.72(18) . . . . ?
C2 N1 C5 C3 169.59(14) . . . . ?
C8 C3 C5 N1 -60.6(2) . . . . ?
C10 C3 C5 N1 121.94(17) . . . . ?
N1 C1 C6 C9 171.17(12) . . . . ?
C1 C1 C6 C9 -60.24(19) 2_554 . . . ?
C11 C4 C7 C17 0.1(2) . . . . ?
C2 C4 C7 C17 -179.67(15) . . . . ?
C10 C3 C8 C12 -0.1(2) . . . . ?
C5 C3 C8 C12 -177.57(15) . . . . ?
C1 C6 C9 C9 56.3(2) . . . 2_554 ?
C8 C3 C10 C15 -0.6(3) . . . . ?
C5 C3 C10 C15 176.91(16) . . . . ?
C7 C4 C11 C16 0.5(3) . . . . ?
C2 C4 C11 C16 -179.68(16) . . . . ?
C3 C8 C12 C13 0.2(3) . . . . ?
C8 C12 C13 C15 0.2(3) . . . . ?
C12 C13 C15 C10 -0.9(3) . . . . ?
C3 C10 C15 C13 1.1(3) . . . . ?
C17 C14 C16 C11 0.9(4) . . . . ?
C4 C11 C16 C14 -1.0(3) . . . . ?
C16 C14 C17 C7 -0.2(3) . . . . ?
C4 C7 C17 C14 -0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.067
