# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2014

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#
#                 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
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#  data retrieval see:
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#  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.
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 Mn N O5'
_chemical_formula_weight         306.17

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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                   7.491(3)
_cell_length_b                   15.386(6)
_cell_length_c                   11.226(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1294.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4297
_cell_measurement_theta_min      2.2454
_cell_measurement_theta_max      27.4816

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5469
_exptl_absorpt_correction_T_max  1.0000
_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  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10207
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2673
_reflns_number_gt                2628
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0415P)^2^+0.9687P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   0.03(2)
_refine_ls_number_reflns         2673
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
Mn Mn 0.47669(4) 0.21766(2) 0.35745(6) 0.02473(11) Uani 1 1 d . . .
C1 C 0.6471(3) 0.39409(16) 0.2743(3) 0.0270(5) Uani 1 1 d . . .
C2 C 0.7612(4) 0.65513(18) 0.0114(3) 0.0316(6) Uani 1 1 d . . .
C3 C 0.5909(3) 0.48003(16) 0.2203(2) 0.0265(5) Uani 1 1 d . . .
C4 C 0.4274(4) 0.51596(19) 0.2554(3) 0.0333(6) Uani 1 1 d . . .
H4A H 0.3547 0.4853 0.3078 0.040 Uiso 1 1 calc R . .
C5 C 0.3714(4) 0.5964(2) 0.2135(3) 0.0403(7) Uani 1 1 d . . .
C6 C 0.4831(4) 0.6411(2) 0.1355(3) 0.0370(7) Uani 1 1 d . . .
H6A H 0.4489 0.6956 0.1082 0.044 Uiso 1 1 calc R . .
C7 C 0.6444(4) 0.60612(17) 0.0973(3) 0.0287(6) Uani 1 1 d . . .
C8 C 0.6988(4) 0.52525(16) 0.1407(3) 0.0290(5) Uani 1 1 d . . .
H8A H 0.8072 0.5017 0.1165 0.035 Uiso 1 1 calc R . .
C9 C 0.1941(5) 0.6342(3) 0.2524(5) 0.0683(13) Uani 1 1 d . . .
H9A H 0.1361 0.5945 0.3058 0.103 Uiso 1 1 calc R . .
H9B H 0.1200 0.6434 0.1838 0.103 Uiso 1 1 calc R . .
H9C H 0.2139 0.6885 0.2922 0.103 Uiso 1 1 calc R . .
C10 C 0.6505(4) 0.1304(2) 0.1444(3) 0.0423(7) Uani 1 1 d . . .
H10A H 0.5741 0.0858 0.1671 0.051 Uiso 1 1 calc R . .
C11 C 0.7246(6) 0.0397(3) -0.0231(4) 0.0707(13) Uani 1 1 d . . .
H11A H 0.6314 0.0047 0.0107 0.106 Uiso 1 1 calc R . .
H11B H 0.8350 0.0082 -0.0210 0.106 Uiso 1 1 calc R . .
H11C H 0.6953 0.0537 -0.1041 0.106 Uiso 1 1 calc R . .
C12 C 0.8771(8) 0.1819(4) 0.0093(5) 0.0828(15) Uani 1 1 d . . .
H12A H 0.8744 0.2310 0.0620 0.124 Uiso 1 1 calc R . .
H12B H 0.8531 0.2008 -0.0706 0.124 Uiso 1 1 calc R . .
H12C H 0.9928 0.1551 0.0125 0.124 Uiso 1 1 calc R . .
O1 O 0.5252(3) 0.34916(14) 0.3194(2) 0.0378(6) Uani 1 1 d . . .
O2 O 0.8103(3) 0.37599(12) 0.2724(2) 0.0356(5) Uani 1 1 d . . .
O3 O 0.7144(3) 0.73122(12) -0.0203(2) 0.0377(5) Uani 1 1 d . . .
O4 O 0.9037(3) 0.62206(15) -0.0242(2) 0.0466(6) Uani 1 1 d . . .
O5 O 0.6574(3) 0.19475(15) 0.2087(2) 0.0452(6) Uani 1 1 d . . .
N N 0.7429(4) 0.1196(2) 0.0455(3) 0.0478(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Mn 0.02603(17) 0.01942(16) 0.0287(2) -0.0007(2) 0.0017(3) -0.00215(11)
C1 0.0269(12) 0.0236(11) 0.0307(14) 0.0039(10) -0.0002(10) -0.0006(9)
C2 0.0366(14) 0.0285(14) 0.0296(15) 0.0089(11) -0.0077(11) -0.0091(11)
C3 0.0264(12) 0.0231(11) 0.0301(14) 0.0052(10) -0.0034(11) -0.0011(9)
C4 0.0290(12) 0.0349(14) 0.0360(17) 0.0087(11) 0.0030(12) 0.0014(11)
C5 0.0367(15) 0.0397(16) 0.0444(18) 0.0117(13) 0.0057(13) 0.0117(12)
C6 0.0444(16) 0.0274(14) 0.0393(18) 0.0080(12) -0.0031(13) 0.0073(12)
C7 0.0316(13) 0.0249(12) 0.0295(14) 0.0060(10) -0.0060(11) -0.0021(10)
C8 0.0250(12) 0.0267(12) 0.0352(14) 0.0064(11) 0.0002(10) 0.0002(10)
C9 0.052(2) 0.070(2) 0.083(3) 0.024(2) 0.026(2) 0.0313(19)
C10 0.0380(16) 0.0413(16) 0.0475(19) -0.0074(15) 0.0056(14) -0.0016(13)
C11 0.070(3) 0.078(3) 0.065(3) -0.036(2) 0.009(2) 0.004(2)
C12 0.099(4) 0.082(3) 0.067(3) 0.006(2) 0.034(3) -0.015(3)
O1 0.0341(10) 0.0243(10) 0.0550(16) 0.0113(8) 0.0086(9) 0.0003(8)
O2 0.0273(9) 0.0294(10) 0.0500(13) 0.0139(9) -0.0024(9) 0.0034(7)
O3 0.0497(13) 0.0262(9) 0.0373(12) 0.0103(8) -0.0160(10) -0.0110(9)
O4 0.0373(12) 0.0476(12) 0.0549(15) 0.0220(12) 0.0117(11) -0.0012(10)
O5 0.0483(13) 0.0415(12) 0.0458(14) -0.0109(10) 0.0119(11) -0.0036(11)
N 0.0489(16) 0.0573(18) 0.0374(17) -0.0119(12) 0.0067(13) 0.0039(14)

_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
Mn O1 2.099(2) . ?
Mn O2 2.131(2) 3_455 ?
Mn O3 2.133(2) 2_665 ?
Mn O4 2.175(2) 4_645 ?
Mn O5 2.178(2) . ?
C1 O1 1.252(3) . ?
C1 O2 1.254(3) . ?
C1 C3 1.514(3) . ?
C2 O4 1.249(4) . ?
C2 O3 1.273(3) . ?
C2 C7 1.505(4) . ?
C3 C8 1.391(4) . ?
C3 C4 1.400(4) . ?
C4 C5 1.389(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(5) . ?
C5 C9 1.514(5) . ?
C6 C7 1.390(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.397(4) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O5 1.227(4) . ?
C10 N 1.319(4) . ?
C10 H10A 0.9300 . ?
C11 N 1.457(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N 1.447(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O2 Mn 2.131(2) 3 ?
O3 Mn 2.133(2) 2_664 ?
O4 Mn 2.175(2) 4_654 ?

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 Mn O2 131.44(9) . 3_455 ?
O1 Mn O3 83.79(8) . 2_665 ?
O2 Mn O3 98.36(9) 3_455 2_665 ?
O1 Mn O4 134.79(9) . 4_645 ?
O2 Mn O4 93.28(9) 3_455 4_645 ?
O3 Mn O4 97.62(10) 2_665 4_645 ?
O1 Mn O5 83.82(9) . . ?
O2 Mn O5 84.87(9) 3_455 . ?
O3 Mn O5 165.89(9) 2_665 . ?
O4 Mn O5 95.89(10) 4_645 . ?
O1 C1 O2 126.5(3) . . ?
O1 C1 C3 116.2(2) . . ?
O2 C1 C3 117.3(2) . . ?
O4 C2 O3 121.4(3) . . ?
O4 C2 C7 119.9(2) . . ?
O3 C2 C7 118.6(3) . . ?
C8 C3 C4 119.4(2) . . ?
C8 C3 C1 122.1(2) . . ?
C4 C3 C1 118.4(2) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 C9 120.6(3) . . ?
C6 C5 C9 121.3(3) . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 C2 120.6(2) . . ?
C8 C7 C2 120.0(3) . . ?
C3 C8 C7 120.0(3) . . ?
C3 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C10 N 125.1(3) . . ?
O5 C10 H10A 117.4 . . ?
N C10 H10A 117.4 . . ?
N C11 H11A 109.5 . . ?
N C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N C12 H12A 109.5 . . ?
N C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 O1 Mn 137.78(19) . . ?
C1 O2 Mn 135.45(18) . 3 ?
C2 O3 Mn 134.73(18) . 2_664 ?
C2 O4 Mn 105.80(18) . 4_654 ?
C10 O5 Mn 123.8(2) . . ?
C10 N C12 121.2(3) . . ?
C10 N C11 120.1(3) . . ?
C12 N C11 118.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 959274'