# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_dd564a
_database_code_depnum_ccdc_archive 'CCDC 1025818'
_audit_update_record             
;
2014-09-24 deposited with the CCDC.
2015-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Br4 Cl Fe N3 O3'
_chemical_formula_weight         760.32

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   13.314(6)
_cell_length_b                   14.720(6)
_cell_length_c                   13.228(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.192(6)
_cell_angle_gamma                90.00
_cell_volume                     2543.2(18)
_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       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1468
_exptl_absorpt_coefficient_mu    7.009
_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  ?
_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            8389
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         21.80
_reflns_number_total             2956
_reflns_number_gt                1883
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0565P)²+2.1100P] 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         2956
_refine_ls_number_parameters     292
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.015
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.90827(10) 0.42558(9) 0.09139(10) 0.0428(4) Uani 1 1 d . A .
Br1 Br 1.41033(8) 0.19974(8) 0.22321(9) 0.0730(4) Uani 1 1 d . . .
Br2 Br 1.05463(9) 0.20343(8) -0.09010(8) 0.0657(4) Uani 1 1 d . . .
Br3 Br 0.68849(9) 0.36256(8) -0.22542(9) 0.0695(4) Uani 1 1 d . A .
Br4 Br 0.40139(9) 0.62306(9) -0.14513(10) 0.0829(5) Uani 1 1 d . A .
Cl1 Cl 0.8564(2) 0.31755(18) 0.1868(2) 0.0657(8) Uani 1 1 d . . .
O1 O 1.0063(5) 0.3667(4) 0.0286(4) 0.0504(18) Uani 1 1 d . . .
O2 O 0.8114(5) 0.4402(4) -0.0324(4) 0.0468(17) Uani 1 1 d . . .
N1 N 1.0340(6) 0.4829(5) 0.1905(5) 0.048(2) Uani 1 1 d . . .
N2 N 0.8454(6) 0.5436(5) 0.1408(6) 0.048(2) Uani 1 1 d . . .
C1 C 1.0932(7) 0.3296(6) 0.0755(7) 0.041(2) Uani 1 1 d . A .
C2 C 1.1319(8) 0.2549(7) 0.0322(7) 0.046(3) Uani 1 1 d . . .
C3 C 1.2262(7) 0.2152(7) 0.0746(7) 0.049(3) Uani 1 1 d . . .
H3 H 1.2509 0.1661 0.0426 0.059 Uiso 1 1 calc R . .
C4 C 1.2812(7) 0.2501(7) 0.1643(8) 0.054(3) Uani 1 1 d . . .
C5 C 1.2462(7) 0.3243(7) 0.2121(7) 0.044(3) Uani 1 1 d . A .
H5 H 1.2850 0.3479 0.2725 0.053 Uiso 1 1 calc R . .
C6 C 1.1513(7) 0.3633(6) 0.1682(6) 0.039(2) Uani 1 1 d . . .
C7 C 1.1205(7) 0.4445(7) 0.2170(7) 0.045(3) Uani 1 1 d . A .
H7 H 1.1671 0.4699 0.2710 0.054 Uiso 1 1 calc R . .
C8 C 1.0149(9) 0.5729(7) 0.2367(8) 0.066(3) Uani 1 1 d . A 1
H8A H 1.0550 0.5776 0.3060 0.080 Uiso 0.650(16) 1 calc PR B 1
H8B H 1.0350 0.6219 0.1957 0.080 Uiso 0.650(16) 1 calc PR B 1
C9 C 0.9049(9) 0.5800(8) 0.2390(8) 0.065(3) Uani 1 1 d . A 1
H9 H 0.8871 0.6441 0.2455 0.078 Uiso 0.650(16) 1 calc PR B 1
C10A C 0.8888(15) 0.5303(14) 0.3313(13) 0.108(8) Uani 0.650(16) 1 d P A 1
H10A H 0.8177 0.5329 0.3356 0.161 Uiso 0.650(16) 1 calc PR B 1
H10B H 0.9291 0.5577 0.3917 0.161 Uiso 0.650(16) 1 calc PR B 1
H10C H 0.9091 0.4681 0.3268 0.161 Uiso 0.650(16) 1 calc PR B 1
H8 H 1.0304 0.6222 0.2012 0.129 Uiso 0.350(16) 1 d PR B 2
H9A H 0.8795 0.6395 0.2568 0.129 Uiso 0.350(16) 1 d PR B 2
H9B H 0.8839 0.5402 0.3021 0.129 Uiso 0.350(16) 1 d PR B 2
C10B C 1.069(2) 0.5836(18) 0.354(2) 0.056(10) Uiso 0.350(16) 1 d P B 2
H10D H 1.1411 0.5809 0.3567 0.084 Uiso 0.350(16) 1 d PR B 2
H10E H 1.0486 0.5345 0.3937 0.084 Uiso 0.350(16) 1 d PR B 2
H10F H 1.0517 0.6404 0.3826 0.084 Uiso 0.350(16) 1 d PR B 2
C11 C 0.7627(8) 0.5826(7) 0.1002(7) 0.053(3) Uani 1 1 d . A .
H11 H 0.7439 0.6338 0.1334 0.063 Uiso 1 1 calc R . .
C12 C 0.6951(7) 0.5544(6) 0.0069(7) 0.042(2) Uani 1 1 d . . .
C13 C 0.6007(8) 0.5959(7) -0.0230(8) 0.056(3) Uani 1 1 d . A .
H13 H 0.5834 0.6434 0.0168 0.067 Uiso 1 1 calc R . .
C14 C 0.5324(7) 0.5701(8) -0.1080(9) 0.058(3) Uani 1 1 d . . .
C15 C 0.5592(7) 0.5011(7) -0.1708(8) 0.056(3) Uani 1 1 d . A .
H15 H 0.5142 0.4840 -0.2306 0.067 Uiso 1 1 calc R . .
C16 C 0.6524(7) 0.4592(6) -0.1432(7) 0.040(2) Uani 1 1 d . . .
C17 C 0.7230(7) 0.4832(6) -0.0536(7) 0.040(2) Uani 1 1 d . A .
O3 O 0.6996(11) -0.0375(8) 0.0543(9) 0.166(6) Uani 1 1 d . B 1
C20 C 0.6473(15) 0.0209(16) 0.0275(15) 0.170(8) Uani 1 1 d DU B 1
H20B H 0.5803 0.0071 0.0327 0.204 Uiso 1 1 d R B 1
N3B N 0.6520(14) 0.1012(13) -0.0231(18) 0.104(8) Uiso 0.650(16) 1 d PD B 1
C21B C 0.5638(17) 0.1552(16) -0.045(2) 0.151(11) Uiso 0.650(16) 1 d PD B 1
H21D H 0.5137 0.1324 -0.0081 0.227 Uiso 0.650(16) 1 calc PR B 1
H21E H 0.5364 0.1536 -0.1177 0.227 Uiso 0.650(16) 1 calc PR B 1
H21F H 0.5809 0.2167 -0.0241 0.227 Uiso 0.650(16) 1 calc PR B 1
C22B C 0.7465(15) 0.1378(17) -0.035(2) 0.142(10) Uiso 0.650(16) 1 d PD B 1
H22D H 0.8007 0.0972 -0.0060 0.213 Uiso 0.650(16) 1 calc PR B 1
H22E H 0.7567 0.1956 -0.0014 0.213 Uiso 0.650(16) 1 calc PR B 1
H22F H 0.7464 0.1456 -0.1075 0.213 Uiso 0.650(16) 1 calc PR B 1
N3 N 0.690(3) 0.0913(19) -0.018(3) 0.115(16) Uiso 0.350(16) 1 d PD B 2
C21 C 0.636(4) 0.1728(19) -0.039(4) 0.18(3) Uiso 0.350(16) 1 d PD B 2
H21A H 0.6756 0.2152 -0.0699 0.269 Uiso 0.350(16) 1 calc PR B 2
H21B H 0.6227 0.1977 0.0242 0.269 Uiso 0.350(16) 1 calc PR B 2
H21C H 0.5722 0.1614 -0.0853 0.269 Uiso 0.350(16) 1 calc PR B 2
C22 C 0.771(3) 0.073(4) -0.067(4) 0.23(4) Uiso 0.350(16) 1 d PD B 2
H22A H 0.7827 0.1248 -0.1080 0.349 Uiso 0.350(16) 1 calc PR B 2
H22B H 0.7547 0.0212 -0.1115 0.349 Uiso 0.350(16) 1 calc PR B 2
H22C H 0.8316 0.0609 -0.0168 0.349 Uiso 0.350(16) 1 calc PR B 2


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Fe O1 1.888(6) . ?
Fe O2 1.890(6) . ?
Fe N2 2.087(8) . ?
Fe N1 2.093(7) . ?
Fe Cl1 2.222(3) . ?
Br1 C4 1.895(10) . ?
Br2 C2 1.898(9) . ?
Br3 C16 1.908(9) . ?
Br4 C14 1.887(10) . ?
O1 C1 1.320(10) . ?
O2 C17 1.317(10) . ?
N1 C7 1.270(11) . ?
N1 C8 1.501(11) . ?
N2 C11 1.266(11) . ?
N2 C9 1.484(12) . ?
C1 C2 1.384(12) . ?
C1 C6 1.408(12) . ?
C2 C3 1.400(13) . ?
C3 C4 1.367(12) . ?
C4 C5 1.387(12) . ?
C5 C6 1.407(12) . ?
C6 C7 1.454(12) . ?
C8 C9 1.475(14) . ?
C9 C10A 1.474(18) . ?
C11 C12 1.440(13) . ?
C12 C13 1.385(13) . ?
C12 C17 1.412(12) . ?
C13 C14 1.357(14) . ?
C14 C15 1.401(13) . ?
C15 C16 1.370(12) . ?
C16 C17 1.407(12) . ?
O3 C20 1.12(2) . ?
C20 N3B 1.37(2) . ?
N3B C21B 1.401(15) . ?
N3B C22B 1.407(15) . ?
N3 C22 1.386(17) . ?
N3 C21 1.400(17) . ?

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
O1 Fe O2 94.9(3) . . ?
O1 Fe N2 150.8(3) . . ?
O2 Fe N2 85.9(3) . . ?
O1 Fe N1 85.6(3) . . ?
O2 Fe N1 145.6(3) . . ?
N2 Fe N1 77.8(3) . . ?
O1 Fe Cl1 103.8(2) . . ?
O2 Fe Cl1 109.8(2) . . ?
N2 Fe Cl1 103.3(2) . . ?
N1 Fe Cl1 103.4(2) . . ?
C1 O1 Fe 127.0(6) . . ?
C17 O2 Fe 132.1(6) . . ?
C7 N1 C8 119.8(8) . . ?
C7 N1 Fe 124.4(6) . . ?
C8 N1 Fe 115.7(6) . . ?
C11 N2 C9 118.7(8) . . ?
C11 N2 Fe 127.9(7) . . ?
C9 N2 Fe 113.4(6) . . ?
O1 C1 C2 119.8(8) . . ?
O1 C1 C6 123.1(8) . . ?
C2 C1 C6 117.1(9) . . ?
C1 C2 C3 122.9(9) . . ?
C1 C2 Br2 119.0(7) . . ?
C3 C2 Br2 118.1(8) . . ?
C4 C3 C2 118.6(9) . . ?
C3 C4 C5 121.3(9) . . ?
C3 C4 Br1 120.0(8) . . ?
C5 C4 Br1 118.6(8) . . ?
C4 C5 C6 119.2(9) . . ?
C5 C6 C1 120.8(9) . . ?
C5 C6 C7 117.5(8) . . ?
C1 C6 C7 121.5(8) . . ?
N1 C7 C6 124.3(8) . . ?
C9 C8 N1 108.6(9) . . ?
C8 C9 C10A 106.7(11) . . ?
C8 C9 N2 108.6(9) . . ?
C10A C9 N2 114.1(12) . . ?
N2 C11 C12 125.4(9) . . ?
C13 C12 C17 119.4(9) . . ?
C13 C12 C11 119.9(9) . . ?
C17 C12 C11 120.7(9) . . ?
C14 C13 C12 122.5(10) . . ?
C13 C14 C15 119.2(9) . . ?
C13 C14 Br4 122.5(10) . . ?
C15 C14 Br4 118.3(9) . . ?
C16 C15 C14 119.4(9) . . ?
C15 C16 C17 122.3(9) . . ?
C15 C16 Br3 120.0(8) . . ?
C17 C16 Br3 117.7(7) . . ?
O2 C17 C16 118.8(9) . . ?
O2 C17 C12 124.0(8) . . ?
C16 C17 C12 117.2(9) . . ?
O3 C20 N3B 137(2) . . ?
C20 N3B C21B 118.5(13) . . ?
C20 N3B C22B 121.0(13) . . ?
C21B N3B C22B 119.4(16) . . ?
C22 N3 C21 120(2) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        21.80
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.112
