# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_snd3_abs

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H18 Fe N3 O6'
_chemical_formula_moiety         'C21 H18 Fe N3 O6'
_chemical_formula_weight         464.24
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   31.2431(16)
_cell_length_b                   8.2932(4)
_cell_length_c                   15.2316(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.7590(10)
_cell_angle_gamma                90.0000
_cell_volume                     3942.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7856
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      14.18
_cell_measurement_temperature    153
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.190
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1912.00
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      153
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7738
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2820
_reflns_number_gt                2678
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0747
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         2820
_refine_ls_number_parameters     280
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0418P)²+4.7979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.520
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Fe Fe 0.3463 0.8444
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.11914(2) 0.25554(3) 0.86518(2) 0.02173(12) Uani 1.0 8 d . . .
O1 O 0.08079(4) 0.44007(15) 0.86398(10) 0.0346(4) Uani 1.0 8 d . . .
O2 O 0.11323(4) 0.20426(17) 0.73929(8) 0.0297(3) Uani 1.0 8 d . . .
O3 O 0.16634(4) 0.09882(15) 0.87588(8) 0.0273(3) Uani 1.0 8 d . . .
O4 O 0.01296(5) 0.5222(2) 0.85554(19) 0.0839(8) Uani 1.0 8 d . . .
O5 O 0.13916(6) 0.24380(17) 0.60743(10) 0.0458(5) Uani 1.0 8 d . . .
O6 O 0.21769(5) -0.0191(2) 0.95987(10) 0.0442(4) Uani 1.0 8 d . . .
N1 N 0.05858(5) 0.13507(18) 0.87764(10) 0.0255(4) Uani 1.0 8 d . . .
N2 N 0.16580(5) 0.41921(18) 0.81357(9) 0.0213(4) Uani 1.0 8 d . . .
N3 N 0.13223(5) 0.23814(18) 1.01115(10) 0.0263(4) Uani 1.0 8 d . . .
C1 C 0.02617(7) 0.2421(3) 0.86677(16) 0.0342(6) Uani 1.0 8 d . . .
C2 C -0.01617(7) 0.1966(3) 0.86152(17) 0.0420(6) Uani 1.0 8 d . . .
C3 C -0.02591(7) 0.0344(3) 0.86605(16) 0.0402(6) Uani 1.0 8 d . . .
C4 C 0.00685(7) -0.0750(3) 0.87738(14) 0.0334(5) Uani 1.0 8 d . . .
C5 C 0.04935(6) -0.0233(3) 0.88411(12) 0.0266(5) Uani 1.0 8 d . . .
C6 C 0.08543(7) -0.1396(3) 0.89988(14) 0.0339(5) Uani 1.0 8 d . . .
C7 C 0.03955(7) 0.4166(3) 0.86071(18) 0.0454(6) Uani 1.0 8 d . . .
C8 C 0.19053(6) 0.5314(3) 0.85422(12) 0.0243(4) Uani 1.0 8 d . . .
C9 C 0.22353(6) 0.6044(3) 0.81066(13) 0.0332(5) Uani 1.0 8 d . . .
C10 C 0.23167(6) 0.5595(3) 0.72614(14) 0.0353(5) Uani 1.0 8 d . . .
C11 C 0.20509(6) 0.4478(3) 0.68374(12) 0.0302(5) Uani 1.0 8 d . . .
C12 C 0.17221(6) 0.3819(3) 0.72863(11) 0.0238(4) Uani 1.0 8 d . . .
C13 C 0.18190(6) 0.5738(3) 0.94676(13) 0.0327(5) Uani 1.0 8 d . . .
C14 C 0.13968(7) 0.2675(3) 0.68578(13) 0.0290(5) Uani 1.0 8 d . . .
C15 C 0.16494(6) 0.1351(3) 1.02897(12) 0.0282(5) Uani 1.0 8 d . . .
C16 C 0.17857(7) 0.0902(3) 1.11255(14) 0.0410(6) Uani 1.0 8 d . . .
C17 C 0.15717(9) 0.1494(3) 1.18276(14) 0.0496(7) Uani 1.0 8 d . . .
C18 C 0.12438(10) 0.2550(3) 1.16617(15) 0.0479(7) Uani 1.0 8 d . . .
C19 C 0.11170(7) 0.3013(3) 1.08015(14) 0.0363(5) Uani 1.0 8 d . . .
C20 C 0.07613(8) 0.4172(3) 1.06391(17) 0.0530(7) Uani 1.0 8 d . . .
C21 C 0.18571(6) 0.0646(3) 0.95070(13) 0.0286(5) Uani 1.0 8 d . . .
H2 H -0.0382 0.2751 0.8550 0.0503 Uiso 1.0 8 d . . .
H3 H -0.0549 -0.0008 0.8614 0.0483 Uiso 1.0 8 d . . .
H4 H 0.0006 -0.1868 0.8806 0.0401 Uiso 1.0 8 d . . .
H6A H 0.0751 -0.2496 0.8890 0.0407 Uiso 1.0 8 d . . .
H6B H 0.0966 -0.1303 0.9609 0.0407 Uiso 1.0 8 d . . .
H6C H 0.1083 -0.1150 0.8601 0.0407 Uiso 1.0 8 d . . .
H9 H 0.2405 0.6854 0.8394 0.0399 Uiso 1.0 8 d . . .
H10 H 0.2552 0.6047 0.6973 0.0424 Uiso 1.0 8 d . . .
H11 H 0.2095 0.4172 0.6248 0.0362 Uiso 1.0 8 d . . .
H13A H 0.1509 0.5763 0.9538 0.0392 Uiso 1.0 8 d . . .
H13B H 0.1941 0.6800 0.9609 0.0392 Uiso 1.0 8 d . . .
H13C H 0.1950 0.4928 0.9865 0.0392 Uiso 1.0 8 d . . .
H16 H 0.2023 0.0197 1.1218 0.0492 Uiso 1.0 8 d . . .
H17 H 0.1651 0.1175 1.2412 0.0596 Uiso 1.0 8 d . . .
H18 H 0.1097 0.2984 1.2139 0.0574 Uiso 1.0 8 d . . .
H20A H 0.0517 0.3619 1.0346 0.0636 Uiso 1.0 8 d . . .
H20B H 0.0856 0.5049 1.0263 0.0636 Uiso 1.0 8 d . . .
H20C H 0.0675 0.4618 1.1200 0.0636 Uiso 1.0 8 d . . .



#==============================================================================
_computing_data_collection       Unknown
_computing_cell_refinement       Unknown
_computing_data_reduction        Unknown
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Fe1 O1 1.9431(14) yes . .
Fe1 O2 1.9641(13) yes . .
Fe1 O3 1.9666(14) yes . .
Fe1 N1 2.1561(17) yes . .
Fe1 N2 2.1670(16) yes . .
Fe1 N3 2.2459(16) yes . .
O1 C7 1.302(3) yes . .
O2 C14 1.299(3) yes . .
O3 C21 1.296(3) yes . .
O4 C7 1.207(3) yes . .
O5 C14 1.209(3) yes . .
O6 C21 1.219(3) yes . .
N1 C1 1.351(3) yes . .
N1 C5 1.350(3) yes . .
N2 C8 1.342(3) yes . .
N2 C12 1.354(3) yes . .
N3 C15 1.350(3) yes . .
N3 C19 1.362(3) yes . .
C1 C2 1.374(3) yes . .
C1 C7 1.510(3) yes . .
C2 C3 1.382(4) yes . .
C3 C4 1.372(3) yes . .
C4 C5 1.394(3) yes . .
C5 C6 1.494(3) yes . .
C8 C9 1.391(3) yes . .
C8 C13 1.490(3) yes . .
C9 C10 1.375(3) yes . .
C10 C11 1.383(3) yes . .
C11 C12 1.374(3) yes . .
C12 C14 1.515(3) yes . .
C15 C16 1.374(3) yes . .
C15 C21 1.503(3) yes . .
C16 C17 1.378(4) yes . .
C17 C18 1.362(4) yes . .
C18 C19 1.404(4) yes . .
C19 C20 1.481(4) yes . .
C2 H2 0.949(3) no . .
C3 H3 0.951(3) no . .
C4 H4 0.949(2) no . .
C6 H6A 0.979(2) no . .
C6 H6B 0.980(2) no . .
C6 H6C 0.980(3) no . .
C9 H9 0.950(2) no . .
C10 H10 0.951(2) no . .
C11 H11 0.9494(19) no . .
C13 H13A 0.9798(19) no . .
C13 H13B 0.980(2) no . .
C13 H13C 0.980(2) no . .
C16 H16 0.950(3) no . .
C17 H17 0.950(3) no . .
C18 H18 0.949(3) no . .
C20 H20A 0.980(3) no . .
C20 H20B 0.980(3) no . .
C20 H20C 0.981(3) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 Fe1 O2 97.61(7) yes . . .
O1 Fe1 O3 168.78(6) yes . . .
O1 Fe1 N1 79.77(6) yes . . .
O1 Fe1 N2 85.90(6) yes . . .
O1 Fe1 N3 98.21(6) yes . . .
O2 Fe1 O3 88.43(6) yes . . .
O2 Fe1 N1 86.79(6) yes . . .
O2 Fe1 N2 79.32(6) yes . . .
O2 Fe1 N3 163.07(6) yes . . .
O3 Fe1 N1 110.13(6) yes . . .
O3 Fe1 N2 85.94(6) yes . . .
O3 Fe1 N3 77.02(6) yes . . .
N1 Fe1 N2 158.55(6) yes . . .
N1 Fe1 N3 90.11(6) yes . . .
N2 Fe1 N3 107.80(6) yes . . .
Fe1 O1 C7 119.42(13) yes . . .
Fe1 O2 C14 119.49(12) yes . . .
Fe1 O3 C21 122.30(12) yes . . .
Fe1 N1 C1 109.92(13) yes . . .
Fe1 N1 C5 130.46(13) yes . . .
C1 N1 C5 119.14(17) yes . . .
Fe1 N2 C8 130.51(12) yes . . .
Fe1 N2 C12 109.67(12) yes . . .
C8 N2 C12 119.39(16) yes . . .
Fe1 N3 C15 109.86(12) yes . . .
Fe1 N3 C19 132.00(13) yes . . .
C15 N3 C19 117.94(17) yes . . .
N1 C1 C2 122.76(19) yes . . .
N1 C1 C7 115.40(18) yes . . .
C2 C1 C7 121.84(19) yes . . .
C1 C2 C3 118.5(2) yes . . .
C2 C3 C4 119.0(2) yes . . .
C3 C4 C5 120.53(19) yes . . .
N1 C5 C4 119.99(18) yes . . .
N1 C5 C6 118.53(17) yes . . .
C4 C5 C6 121.48(18) yes . . .
O1 C7 O4 124.8(2) yes . . .
O1 C7 C1 114.68(18) yes . . .
O4 C7 C1 120.5(2) yes . . .
N2 C8 C9 120.34(17) yes . . .
N2 C8 C13 118.28(17) yes . . .
C9 C8 C13 121.38(17) yes . . .
C8 C9 C10 120.24(18) yes . . .
C9 C10 C11 118.96(19) yes . . .
C10 C11 C12 118.70(18) yes . . .
N2 C12 C11 122.20(17) yes . . .
N2 C12 C14 115.31(17) yes . . .
C11 C12 C14 122.45(17) yes . . .
O2 C14 O5 125.09(19) yes . . .
O2 C14 C12 114.62(16) yes . . .
O5 C14 C12 120.28(19) yes . . .
N3 C15 C16 123.75(18) yes . . .
N3 C15 C21 116.01(16) yes . . .
C16 C15 C21 120.21(18) yes . . .
C15 C16 C17 118.8(2) yes . . .
C16 C17 C18 118.3(2) yes . . .
C17 C18 C19 121.7(3) yes . . .
N3 C19 C18 119.5(2) yes . . .
N3 C19 C20 119.88(19) yes . . .
C18 C19 C20 120.6(3) yes . . .
O3 C21 O6 124.82(19) yes . . .
O3 C21 C15 114.28(16) yes . . .
O6 C21 C15 120.89(18) yes . . .
C1 C2 H2 120.6(3) no . . .
C3 C2 H2 120.8(3) no . . .
C2 C3 H3 120.4(3) no . . .
C4 C3 H3 120.5(3) no . . .
C3 C4 H4 119.9(3) no . . .
C5 C4 H4 119.6(2) no . . .
C5 C6 H6A 109.51(19) no . . .
C5 C6 H6B 109.48(18) no . . .
C5 C6 H6C 109.48(18) no . . .
H6A C6 H6B 109.4(2) no . . .
H6A C6 H6C 109.5(2) no . . .
H6B C6 H6C 109.5(2) no . . .
C8 C9 H9 119.9(2) no . . .
C10 C9 H9 119.9(2) no . . .
C9 C10 H10 120.5(2) no . . .
C11 C10 H10 120.5(2) no . . .
C10 C11 H11 120.6(2) no . . .
C12 C11 H11 120.67(19) no . . .
C8 C13 H13A 109.48(17) no . . .
C8 C13 H13B 109.51(18) no . . .
C8 C13 H13C 109.47(18) no . . .
H13A C13 H13B 109.5(2) no . . .
H13A C13 H13C 109.4(2) no . . .
H13B C13 H13C 109.50(18) no . . .
C15 C16 H16 120.6(3) no . . .
C17 C16 H16 120.6(3) no . . .
C16 C17 H17 120.9(3) no . . .
C18 C17 H17 120.9(3) no . . .
C17 C18 H18 119.3(3) no . . .
C19 C18 H18 119.1(3) no . . .
C19 C20 H20A 109.5(3) no . . .
C19 C20 H20B 109.5(3) no . . .
C19 C20 H20C 109.6(3) no . . .
H20A C20 H20B 109.4(3) no . . .
H20A C20 H20C 109.4(3) no . . .
H20B C20 H20C 109.4(3) no . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Fe1 C6 3.490(2) no . .
Fe1 C13 3.481(2) no . .
O1 C8 3.521(3) no . .
O1 C13 3.524(3) no . .
O1 C19 3.577(3) no . .
O1 C20 3.062(3) no . .
O2 C1 3.432(3) no . .
O2 C5 3.583(3) no . .
O2 C7 3.497(3) no . .
O3 C6 3.244(3) no . .
O3 C12 3.258(3) no . .
O3 C14 3.287(3) no . .
O4 N1 3.522(3) no . .
O4 C2 2.852(3) no . .
O5 N2 3.524(2) no . .
O5 C11 2.868(3) no . .
O6 N3 3.534(3) no . .
O6 C16 2.828(3) no . .
N1 C3 2.766(3) no . .
N2 C10 2.762(3) no . .
N3 C13 3.356(3) no . .
N3 C17 2.790(3) no . .
C1 C4 2.704(3) no . .
C2 C5 2.751(3) no . .
C7 C20 3.247(4) no . .
C8 C11 2.747(3) no . .
C9 C12 2.710(3) no . .
C15 C18 2.686(4) no . .
C16 C19 2.752(3) no . .
O1 C6 3.531(3) no . 1_565
O2 C2 3.333(3) no . 2_556
O2 C3 3.403(3) no . 2_556
O2 C17 3.368(3) no . 4_554
O3 C17 3.590(3) no . 4_554
O4 O4 3.277(4) no . 2_556
O4 C4 3.364(3) no . 1_565
O4 C20 3.136(4) no . 3_567
O5 C13 3.221(3) no . 4_564
O5 C15 3.470(3) no . 4_554
O5 C16 3.031(3) no . 4_554
O5 C17 3.494(3) no . 4_554
O5 C20 3.478(3) no . 4_564
O6 C10 3.374(3) no . 6_546
O6 C11 3.345(3) no . 6_546
O6 C13 3.559(3) no . 1_545
O6 C13 3.412(3) no . 7_557
C1 C2 3.497(4) no . 2_556
C2 O2 3.333(3) no . 2_556
C2 C1 3.497(4) no . 2_556
C2 C2 3.591(4) no . 2_556
C3 O2 3.403(3) no . 2_556
C4 O4 3.364(3) no . 1_545
C6 O1 3.531(3) no . 1_545
C9 C17 3.446(4) no . 4_564
C10 O6 3.374(3) no . 6_556
C10 C17 3.396(4) no . 4_564
C11 O6 3.345(3) no . 6_556
C11 C18 3.527(4) no . 4_564
C12 C18 3.474(3) no . 4_564
C13 O5 3.221(3) no . 4_565
C13 O6 3.559(3) no . 1_565
C13 O6 3.412(3) no . 7_557
C14 C16 3.414(3) no . 4_554
C14 C17 3.501(4) no . 4_554
C15 O5 3.470(3) no . 4_555
C16 O5 3.031(3) no . 4_555
C16 C14 3.414(3) no . 4_555
C17 O2 3.368(3) no . 4_555
C17 O3 3.590(3) no . 4_555
C17 O5 3.494(3) no . 4_555
C17 C9 3.446(4) no . 4_565
C17 C10 3.396(4) no . 4_565
C17 C14 3.501(4) no . 4_555
C18 C11 3.527(4) no . 4_565
C18 C12 3.474(3) no . 4_565
C20 O4 3.136(4) no . 3_567
C20 O5 3.478(3) no . 4_565

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1000597'
