# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_100
_database_code_depnum_ccdc_archive 'CCDC 1047141'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-03-12 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            'C8 H14 Fe Mg N O12'
_chemical_formula_weight         396.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mg Mg 0.0486 0.0363 '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      trigonal
_space_group_IT_number           163
_space_group_name_H-M_alt        'P -3 1 c'
_space_group_name_Hall           '-P 3 2c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   8.2008(2)
_cell_length_b                   8.2008(2)
_cell_length_c                   13.8667(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     807.64(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4102
_cell_measurement_theta_min      2.8660
_cell_measurement_theta_max      28.3004


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             406
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            grey
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_T_min  0.92713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_detector_area_resol_mean 8.4350
_diffrn_reflns_number            7668
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.223
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_full        25.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             516
_reflns_number_gt                429
_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Diamond Version 3.2k Crystal Impact GbR, Bonn, Germany'
_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)+(0.0700P)²+0.3300P] 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         516
_refine_ls_number_parameters     44
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.972
_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 0.3333 0.6667 0.2500 0.0067(4) Uani 0.320(4) 6 d S T P . .
Mg1 Mg 0.3333 0.6667 0.2500 0.0067(4) Uani 0.680(4) 6 d S T P . .
Fe2 Fe 0.0000 1.0000 0.0000 0.0046(3) Uani 0.681(4) 6 d S T P . .
Mg2 Mg 0.0000 1.0000 0.0000 0.0046(3) Uani 0.318(4) 6 d S T P . .
O1 O 0.12126(19) 0.66069(19) 0.16842(9) 0.0175(4) Uani 1 1 d . . . . .
O2 O -0.01090(18) 0.79156(19) 0.08235(9) 0.0147(4) Uani 1 1 d . . . . .
C1 C 0.1288(3) 0.7908(3) 0.11913(12) 0.0156(5) Uani 1 1 d . . . . .
H1 H 0.2468 0.8957 0.1086 0.019 Uiso 1 1 calc R U . . .
N1 N 0.287(2) 0.5588(17) 0.7742(6) 0.042(4) Uiso 0.1667 1 d D . P . .
H1A H 0.3458 0.4927 0.7740 0.051 Uiso 0.1667 1 calc R U P . .
H1B H 0.1636 0.4769 0.7740 0.051 Uiso 0.1667 1 calc R U P . .
C2 C 0.3333 0.6667 0.8650(8) 0.057(2) Uani 0.5 3 d DS TU P . .
H2A H 0.4613 0.7682 0.8625 0.085 Uiso 0.1667 1 calc R U P . .
H2B H 0.3186 0.5853 0.9181 0.085 Uiso 0.1667 1 calc R U P . .
H2C H 0.2505 0.7167 0.8734 0.085 Uiso 0.1667 1 calc R U P . .
C21 C 0.3333 0.6667 0.6857(8) 0.057(2) Uani 0.5 3 d DS TU P . .
H21A H 0.3007 0.7635 0.6918 0.085 Uiso 0.1667 1 calc R U P . .
H21B H 0.2643 0.5849 0.6332 0.085 Uiso 0.1667 1 calc R U P . .
H21C H 0.4659 0.7232 0.6735 0.085 Uiso 0.1667 1 calc R U P . .


_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 O1 2.0546(13) . ?
Fe1 O1 2.0547(13) 4_665 ?
Fe1 O1 2.0547(13) 3_565 ?
Fe1 O1 2.0547(13) 6_565 ?
Fe1 O1 2.0547(13) 2_665 ?
Fe1 O1 2.0547(13) 5 ?
Fe2 O2 2.0202(13) 7_575 ?
Fe2 O2 2.0202(13) 8_455 ?
Fe2 O2 2.0202(13) 2_675 ?
Fe2 O2 2.0202(13) 9_665 ?
Fe2 O2 2.0202(13) 3_465 ?
Fe2 O2 2.0202(13) . ?
O1 C1 1.243(2) . ?
O2 C1 1.257(2) . ?
C1 H1 0.9300 . ?
N1 C21 1.448(9) . ?
N1 C2 1.474(8) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 Fe1 O1 89.14(8) . 4_665 ?
O1 Fe1 O1 92.60(5) . 3_565 ?
O1 Fe1 O1 85.71(7) 4_665 3_565 ?
O1 Fe1 O1 85.71(7) . 6_565 ?
O1 Fe1 O1 92.60(5) 4_665 6_565 ?
O1 Fe1 O1 177.63(8) 3_565 6_565 ?
O1 Fe1 O1 92.60(5) . 2_665 ?
O1 Fe1 O1 177.63(8) 4_665 2_665 ?
O1 Fe1 O1 92.60(5) 3_565 2_665 ?
O1 Fe1 O1 89.14(8) 6_565 2_665 ?
O1 Fe1 O1 177.63(8) . 5 ?
O1 Fe1 O1 92.60(5) 4_665 5 ?
O1 Fe1 O1 89.14(8) 3_565 5 ?
O1 Fe1 O1 92.60(5) 6_565 5 ?
O1 Fe1 O1 85.71(7) 2_665 5 ?
O2 Fe2 O2 91.19(5) 7_575 8_455 ?
O2 Fe2 O2 88.81(5) 7_575 2_675 ?
O2 Fe2 O2 180.00(6) 8_455 2_675 ?
O2 Fe2 O2 91.19(5) 7_575 9_665 ?
O2 Fe2 O2 91.19(5) 8_455 9_665 ?
O2 Fe2 O2 88.81(5) 2_675 9_665 ?
O2 Fe2 O2 88.81(5) 7_575 3_465 ?
O2 Fe2 O2 88.81(5) 8_455 3_465 ?
O2 Fe2 O2 91.19(5) 2_675 3_465 ?
O2 Fe2 O2 180.0 9_665 3_465 ?
O2 Fe2 O2 180.0 7_575 . ?
O2 Fe2 O2 88.81(5) 8_455 . ?
O2 Fe2 O2 91.19(5) 2_675 . ?
O2 Fe2 O2 88.81(5) 9_665 . ?
O2 Fe2 O2 91.19(5) 3_465 . ?
C1 O1 Fe1 127.17(13) . . ?
C1 O2 Fe2 125.35(13) . . ?
O1 C1 O2 124.96(18) . . ?
O1 C1 H1 117.5 . . ?
O2 C1 H1 117.5 . . ?
C21 N1 C2 116.5(10) . . ?
C21 N1 H1A 108.2 . . ?
C2 N1 H1A 108.2 . . ?
C21 N1 H1B 108.2 . . ?
C2 N1 H1B 108.2 . . ?
H1A N1 H1B 107.3 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 2.41 3.161(15) 142.6 11_666
N1 H1A O1 0.89 2.54 3.248(18) 136.8 8_556
N1 H1B O1 0.89 2.18 3.007(17) 155.4 7_566
C2 H2C O2 0.96 2.55 3.422(3) 150.3 9_666

_refine_diff_density_max         0.578
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_190
_database_code_depnum_ccdc_archive 'CCDC 1047142'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-03-12 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            'C8 H14 Fe Mg N O12'
_chemical_formula_weight         396.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mg Mg 0.0486 0.0363 '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      trigonal
_space_group_IT_number           163
_space_group_name_H-M_alt        'P -3 1 c'
_space_group_name_Hall           '-P 3 2c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   8.2067(2)
_cell_length_b                   8.2067(2)
_cell_length_c                   13.8818(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     809.68(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    4448
_cell_measurement_theta_min      2.8596
_cell_measurement_theta_max      28.1861

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             406
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            grey
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_T_min  0.92713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_detector_area_resol_mean 8.4350
_diffrn_reflns_number            7770
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.220
_diffrn_reflns_theta_max         25.659
_diffrn_reflns_theta_full        25.659
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             517
_reflns_number_gt                451
_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Diamond Version 3.2k Crystal Impact GbR, Bonn, Germany'
_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)+(0.0420P)²+0.4600P] 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         517
_refine_ls_number_parameters     46
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.005
_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 0.3333 0.6667 0.2500 0.0092(3) Uani 0.315(4) 6 d S T P . .
Mg1 Mg 0.3333 0.6667 0.2500 0.0092(3) Uani 0.685(4) 6 d S T P . .
Fe2 Fe 0.0000 1.0000 0.0000 0.0073(2) Uani 0.687(4) 6 d S T P . .
Mg2 Mg 0.0000 1.0000 0.0000 0.0073(2) Uani 0.313(4) 6 d S T P . .
O1 O 0.12150(18) 0.66142(19) 0.16846(9) 0.0234(3) Uani 1 1 d . . . . .
O2 O -0.00985(18) 0.79207(17) 0.08225(9) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.1286(3) 0.7907(3) 0.11922(12) 0.0217(4) Uani 1 1 d . . . . .
H1 H 0.2466 0.8955 0.1089 0.026 Uiso 1 1 calc R U . . .
C2 C 0.3333 0.6667 0.8681(9) 0.076(4) Uani 0.5 3 d DS TU P . .
H2A H 0.4641 0.7612 0.8694 0.114 Uiso 0.1667 1 calc R U P . .
H2B H 0.3055 0.5828 0.9217 0.114 Uiso 0.1667 1 calc R U P . .
H2C H 0.2580 0.7258 0.8722 0.114 Uiso 0.1667 1 calc R U P . .
C21 C 0.3333 0.6667 0.6906(11) 0.090(5) Uani 0.5 3 d DS TU P . .
H21A H 0.3224 0.7764 0.7011 0.135 Uiso 0.1667 1 calc R U P . .
H21B H 0.2464 0.5903 0.6413 0.135 Uiso 0.1667 1 calc R U P . .
H21C H 0.4593 0.7043 0.6706 0.135 Uiso 0.1667 1 calc R U P . .
N1 N 0.291(2) 0.5605(19) 0.7783(7) 0.053(4) Uiso 0.1667 1 d D . P . .
H1A H 0.3551 0.4990 0.7781 0.064 Uiso 0.1667 1 calc R U P . .
H1B H 0.1695 0.4747 0.7781 0.064 Uiso 0.1667 1 calc R U P . .


_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 O1 2.0568(12) . ?
Fe1 O1 2.0568(12) 4_665 ?
Fe1 O1 2.0568(12) 6_565 ?
Fe1 O1 2.0568(12) 3_565 ?
Fe1 O1 2.0568(12) 2_665 ?
Fe1 O1 2.0568(12) 5 ?
Fe2 O2 2.0208(12) 7_575 ?
Fe2 O2 2.0208(12) 8_455 ?
Fe2 O2 2.0208(12) 2_675 ?
Fe2 O2 2.0209(12) . ?
Fe2 O2 2.0209(12) 9_665 ?
Fe2 O2 2.0209(12) 3_465 ?
O1 C1 1.239(2) . ?
O2 C1 1.252(2) . ?
C1 H1 0.9300 . ?
C2 N1 1.460(9) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C21 N1 1.435(9) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?

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 Fe1 O1 88.91(8) . 4_665 ?
O1 Fe1 O1 85.90(7) . 6_565 ?
O1 Fe1 O1 92.62(5) 4_665 6_565 ?
O1 Fe1 O1 92.62(5) . 3_565 ?
O1 Fe1 O1 85.90(7) 4_665 3_565 ?
O1 Fe1 O1 177.92(8) 6_565 3_565 ?
O1 Fe1 O1 92.62(5) . 2_665 ?
O1 Fe1 O1 177.92(8) 4_665 2_665 ?
O1 Fe1 O1 88.91(8) 6_565 2_665 ?
O1 Fe1 O1 92.62(5) 3_565 2_665 ?
O1 Fe1 O1 177.92(8) . 5 ?
O1 Fe1 O1 92.62(5) 4_665 5 ?
O1 Fe1 O1 92.62(5) 6_565 5 ?
O1 Fe1 O1 88.91(8) 3_565 5 ?
O1 Fe1 O1 85.90(7) 2_665 5 ?
O2 Fe2 O2 91.22(5) 7_575 8_455 ?
O2 Fe2 O2 88.78(5) 7_575 2_675 ?
O2 Fe2 O2 180.00(6) 8_455 2_675 ?
O2 Fe2 O2 180.0 7_575 . ?
O2 Fe2 O2 88.78(5) 8_455 . ?
O2 Fe2 O2 91.22(5) 2_675 . ?
O2 Fe2 O2 91.22(5) 7_575 9_665 ?
O2 Fe2 O2 91.22(5) 8_455 9_665 ?
O2 Fe2 O2 88.78(5) 2_675 9_665 ?
O2 Fe2 O2 88.78(5) . 9_665 ?
O2 Fe2 O2 88.78(5) 7_575 3_465 ?
O2 Fe2 O2 88.78(5) 8_455 3_465 ?
O2 Fe2 O2 91.22(5) 2_675 3_465 ?
O2 Fe2 O2 91.22(5) . 3_465 ?
O2 Fe2 O2 180.0 9_665 3_465 ?
C1 O1 Fe1 127.46(12) . . ?
C1 O2 Fe2 125.85(12) . . ?
O1 C1 O2 125.40(17) . . ?
O1 C1 H1 117.3 . . ?
O2 C1 H1 117.3 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C21 N1 C2 116.7(13) . . ?
C21 N1 H1A 108.1 . . ?
C2 N1 H1A 108.1 . . ?
C21 N1 H1B 108.1 . . ?
C2 N1 H1B 108.1 . . ?
H1A N1 H1B 107.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 2.43 3.175(15) 140.9 11_666
N1 H1A O1 0.89 2.48 3.211(17) 140.0 8_556
N1 H1B O1 0.89 2.20 3.029(17) 155.0 7_566
C2 H2C O2 0.96 2.53 3.421(3) 153.9 9_666

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_model1
_database_code_depnum_ccdc_archive 'CCDC 1047143'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-03-12 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            'C8 H14 Fe Mg N O12'
_chemical_formula_weight         396.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mg Mg 0.0486 0.0363 '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      trigonal
_space_group_IT_number           163
_space_group_name_H-M_alt        'P -3 1 c'
_space_group_name_Hall           '-P 3 2c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   8.2076(2)
_cell_length_b                   8.2076(2)
_cell_length_c                   13.8988(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     810.85(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3797
_cell_measurement_theta_min      2.8603
_cell_measurement_theta_max      29.3896

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             406
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            grey
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_T_min  0.98913
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_detector_area_resol_mean 8.4350
_diffrn_reflns_number            8337
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         25.656
_diffrn_reflns_theta_full        25.656
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             518
_reflns_number_gt                433
_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;

_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Diamond Version 3.2k Crystal Impact GbR, Bonn, Germany'
_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)+(0.0320P)²+0.1100P] 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         518
_refine_ls_number_parameters     44
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0618
_refine_ls_wR_factor_gt          0.0604
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_restrained_S_all      1.244
_refine_ls_shift/su_max          0.002
_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 0.3333 0.6667 0.2500 0.0157(3) Uani 0.300(3) 6 d S T P . .
Mg1 Mg 0.3333 0.6667 0.2500 0.0157(3) Uani 0.700(4) 6 d S T P . .
Fe2 Fe 0.0000 1.0000 0.0000 0.0134(2) Uani 0.702(3) 6 d S T P . .
Mg2 Mg 0.0000 1.0000 0.0000 0.0134(2) Uani 0.297(4) 6 d S T P . .
O1 O 0.12234(18) 0.6627(2) 0.16840(8) 0.0335(4) Uani 1 1 d . . . . .
O2 O -0.00803(18) 0.79308(17) 0.08205(9) 0.0294(3) Uani 1 1 d . . . . .
C1 C 0.1284(3) 0.7904(3) 0.11959(13) 0.0327(5) Uani 1 1 d . . . . .
H1 H 0.2464 0.8954 0.1097 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3333 0.6667 0.8736(8) 0.105(4) Uani 0.5 3 d DS TU P . .
H2A H 0.4511 0.7824 0.8698 0.158 Uiso 0.1667 1 calc R U P . .
H2B H 0.3390 0.5902 0.9242 0.158 Uiso 0.1667 1 calc R U P . .
H2C H 0.2342 0.6934 0.8867 0.158 Uiso 0.1667 1 calc R U P . .
C21 C 0.3333 0.6667 0.6905(10) 0.105(4) Uani 0.5 3 d DS TU P . .
H21A H 0.3234 0.7773 0.6998 0.158 Uiso 0.1667 1 calc R U P . .
H21B H 0.2434 0.5874 0.6431 0.158 Uiso 0.1667 1 calc R U P . .
H21C H 0.4579 0.7026 0.6689 0.158 Uiso 0.1667 1 calc R U P . .
N1 N 0.296(2) 0.5648(19) 0.7809(7) 0.067(4) Uiso 0.1667 1 d D . P . .
H1A H 0.3543 0.4950 0.7790 0.080 Uiso 0.1667 1 d . U P . .
H1B H 0.1671 0.4706 0.7790 0.080 Uiso 0.1667 1 d . U P . .


_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 O1 2.0566(12) . ?
Fe1 O1 2.0566(12) 4_665 ?
Fe1 O1 2.0566(12) 6_565 ?
Fe1 O1 2.0566(12) 3_565 ?
Fe1 O1 2.0566(12) 2_665 ?
Fe1 O1 2.0566(12) 5 ?
Fe2 O2 2.0192(12) . ?
Fe2 O2 2.0193(12) 8_455 ?
Fe2 O2 2.0193(12) 2_675 ?
Fe2 O2 2.0193(12) 9_665 ?
Fe2 O2 2.0193(12) 7_575 ?
Fe2 O2 2.0193(12) 3_465 ?
O1 C1 1.229(2) . ?
O2 C1 1.245(2) . ?
C1 H1 0.9300 . ?
C2 N1 1.482(9) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C21 N1 1.454(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 H1A 0.9134 . ?
N1 H1B 0.9478 . ?

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 Fe1 O1 88.64(8) . 4_665 ?
O1 Fe1 O1 86.36(7) . 6_565 ?
O1 Fe1 O1 92.51(5) 4_665 6_565 ?
O1 Fe1 O1 92.51(5) . 3_565 ?
O1 Fe1 O1 86.36(7) 4_665 3_565 ?
O1 Fe1 O1 178.42(8) 6_565 3_565 ?
O1 Fe1 O1 92.51(5) . 2_665 ?
O1 Fe1 O1 178.42(8) 4_665 2_665 ?
O1 Fe1 O1 88.64(8) 6_565 2_665 ?
O1 Fe1 O1 92.51(5) 3_565 2_665 ?
O1 Fe1 O1 178.42(8) . 5 ?
O1 Fe1 O1 92.51(5) 4_665 5 ?
O1 Fe1 O1 92.51(5) 6_565 5 ?
O1 Fe1 O1 88.64(8) 3_565 5 ?
O1 Fe1 O1 86.36(7) 2_665 5 ?
O2 Fe2 O2 88.77(5) . 8_455 ?
O2 Fe2 O2 91.23(5) . 2_675 ?
O2 Fe2 O2 180.00(6) 8_455 2_675 ?
O2 Fe2 O2 88.77(5) . 9_665 ?
O2 Fe2 O2 91.23(5) 8_455 9_665 ?
O2 Fe2 O2 88.77(5) 2_675 9_665 ?
O2 Fe2 O2 180.0 . 7_575 ?
O2 Fe2 O2 91.23(5) 8_455 7_575 ?
O2 Fe2 O2 88.77(5) 2_675 7_575 ?
O2 Fe2 O2 91.23(5) 9_665 7_575 ?
O2 Fe2 O2 91.23(5) . 3_465 ?
O2 Fe2 O2 88.77(5) 8_455 3_465 ?
O2 Fe2 O2 91.23(5) 2_675 3_465 ?
O2 Fe2 O2 180.0 9_665 3_465 ?
O2 Fe2 O2 88.77(5) 7_575 3_465 ?
C1 O1 Fe1 128.06(13) . . ?
C1 O2 Fe2 126.86(12) . . ?
O1 C1 O2 126.39(18) . . ?
O1 C1 H1 116.8 . . ?
O2 C1 H1 116.8 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C21 N1 C2 120.2(12) . . ?
C21 N1 H1A 108.0 . . ?
C2 N1 H1A 110.6 . . ?
C21 N1 H1B 106.0 . . ?
C2 N1 H1B 108.5 . . ?
H1A N1 H1B 102.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.91 2.43 3.202(14) 142.2 11_666
N1 H1A O1 0.91 2.48 3.195(17) 135.7 8_556
N1 H1B O1 0.95 2.18 3.058(17) 152.7 7_566

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.044

