# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_dm_mna4b

_audit_creation_date             2013-04-03T23:00:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H16 Mn N2 O6'
_chemical_formula_sum            'C14 H16 Mn N2 O6'
_chemical_formula_weight         363.23
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   10.869(5)
_cell_length_b                   12.130(5)
_cell_length_c                   13.783(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.75(2)
_cell_angle_gamma                90
_cell_volume                     1608.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     1.5418
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.5
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.974
_exptl_absorpt_correction_T_min  0.28132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_number            22994
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.6
_diffrn_reflns_theta_max         71.3
_diffrn_reflns_theta_full        71.3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             3093
_reflns_number_gt                2776
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0477P)²+1.2931P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00086(17)
_refine_ls_number_reflns         3093
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Mn1 Mn 0.72766(3) 0.00169(2) 0.16402(2) 0.02804(12) Uani 1 1 d . . .
O18 O 0.46108(18) -0.40996(16) 0.39350(15) 0.0649(5) Uani 1 1 d . . .
O19 O 0.66523(17) -0.38009(13) 0.53713(12) 0.0482(4) Uani 1 1 d . . .
O28 O 0.81789(17) 0.39737(12) -0.18909(12) 0.0466(4) Uani 1 1 d . . .
O29 O 0.98147(17) 0.27856(13) -0.17528(13) 0.0482(4) Uani 1 1 d . . .
O30 O 0.93086(16) -0.08289(13) 0.22948(14) 0.0489(4) Uani 1 1 d . . .
H30A H 0.9442 -0.1384 0.21 0.073 Uiso 1 1 d R . .
H30B H 1.0011 -0.0423 0.2522 0.073 Uiso 1 1 d R . .
N11 N 0.66678(18) -0.11601(14) 0.26131(13) 0.0376(4) Uani 1 1 d . . .
N21 N 0.79246(19) 0.11597(14) 0.06346(14) 0.0410(4) Uani 1 1 d . . .
C12 C 0.7582(2) -0.1429(2) 0.36397(18) 0.0493(6) Uani 1 1 d . . .
H12 H 0.8438 -0.1072 0.396 0.059 Uiso 1 1 calc R . .
C13 C 0.7317(2) -0.22099(19) 0.42473(17) 0.0461(5) Uani 1 1 d . . .
H13 H 0.7982 -0.2371 0.496 0.055 Uiso 1 1 calc R . .
C14 C 0.6055(2) -0.27488(16) 0.37852(15) 0.0330(4) Uani 1 1 d . . .
C15 C 0.5107(2) -0.24790(18) 0.27266(18) 0.0425(5) Uani 1 1 d . . .
H15 H 0.4247 -0.2828 0.2387 0.051 Uiso 1 1 calc R . .
C16 C 0.5449(2) -0.16832(19) 0.21746(17) 0.0427(5) Uani 1 1 d . . .
H16 H 0.4797 -0.1504 0.1463 0.051 Uiso 1 1 calc R . .
C17 C 0.5737(2) -0.36304(15) 0.44194(16) 0.0335(4) Uani 1 1 d . . .
C22 C 0.8437(3) 0.07151(19) 0.0011(2) 0.0496(6) Uani 1 1 d . . .
H22 H 0.8559 -0.0045 0.0034 0.06 Uiso 1 1 calc R . .
C23 C 0.8794(3) 0.13213(19) -0.0664(2) 0.0489(6) Uani 1 1 d . . .
H23 H 0.9169 0.0973 -0.1068 0.059 Uiso 1 1 calc R . .
C24 C 0.8594(2) 0.24447(17) -0.07391(16) 0.0358(4) Uani 1 1 d . . .
C25 C 0.8054(3) 0.29126(18) -0.01003(18) 0.0450(5) Uani 1 1 d . . .
H25 H 0.7894 0.3668 -0.0126 0.054 Uiso 1 1 calc R . .
C26 C 0.7757(3) 0.22457(18) 0.05739(18) 0.0470(5) Uani 1 1 d . . .
H26 H 0.742 0.2576 0.1012 0.056 Uiso 1 1 calc R . .
C27 C 0.8894(2) 0.31235(16) -0.15262(15) 0.0350(4) Uani 1 1 d . . .
O31 O 1.1450(3) 0.0564(2) 0.3154(4) 0.1521(17) Uani 1 1 d . . .
H31 H 1.0969 0.1226 0.3215 0.228 Uiso 1 1 d R . .
C32 C 1.2634(5) 0.0889(4) 0.3212(5) 0.1255(19) Uani 1 1 d D . .
H32A H 1.3049 0.1418 0.3805 0.151 Uiso 1 1 calc R . .
H32B H 1.2431 0.1277 0.2538 0.151 Uiso 1 1 calc R . .
C33 C 1.3630(6) 0.0077(4) 0.3375(6) 0.147(2) Uani 1 1 d D . .
H33A H 1.3743 0.0011 0.2727 0.221 Uiso 1 1 calc R . .
H33B H 1.3328 -0.0616 0.3525 0.221 Uiso 1 1 calc R . .
H33C H 1.4501 0.028 0.3984 0.221 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Mn1 O18 2.1144(18) 2_655 ?
Mn1 O19 2.1423(15) 4 ?
Mn1 O28 2.1705(15) 4_566 ?
Mn1 O30 2.2111(17) . ?
Mn1 N11 2.2584(16) . ?
Mn1 N21 2.2908(18) . ?
O18 C17 1.227(3) . ?
O18 Mn1 2.1144(18) 2_645 ?
O19 C17 1.240(2) . ?
O19 Mn1 2.1423(15) 4_556 ?
O28 C27 1.248(2) . ?
O28 Mn1 2.1705(15) 4_565 ?
O29 C27 1.248(2) . ?
O30 H30A 0.7639 . ?
O30 H30B 0.8374 . ?
N11 C16 1.333(3) . ?
N11 C12 1.337(3) . ?
N21 C26 1.327(3) . ?
N21 C22 1.337(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.93 . ?
C13 C14 1.379(3) . ?
C13 H13 0.93 . ?
C14 C15 1.377(3) . ?
C14 C17 1.519(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C22 C23 1.376(3) . ?
C22 H22 0.93 . ?
C23 C24 1.376(3) . ?
C23 H23 0.93 . ?
C24 C25 1.387(3) . ?
C24 C27 1.514(3) . ?
C25 C26 1.379(3) . ?
C25 H25 0.93 . ?
C26 H26 0.93 . ?
O31 C32 1.312(4) . ?
O31 H31 0.9829 . ?
C32 C33 1.403(6) . ?
C32 H32A 0.97 . ?
C32 H32B 0.97 . ?
C33 H33A 0.96 . ?
C33 H33B 0.96 . ?
C33 H33C 0.96 . ?

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
O18 Mn1 O19 99.19(7) 2_655 4 ?
O18 Mn1 O28 90.11(7) 2_655 4_566 ?
O19 Mn1 O28 169.63(6) 4 4_566 ?
O18 Mn1 O30 176.93(7) 2_655 . ?
O19 Mn1 O30 83.69(6) 4 . ?
O28 Mn1 O30 87.10(7) 4_566 . ?
O18 Mn1 N11 92.39(8) 2_655 . ?
O19 Mn1 N11 88.88(7) 4 . ?
O28 Mn1 N11 86.15(6) 4_566 . ?
O30 Mn1 N11 88.71(7) . . ?
O18 Mn1 N21 89.11(8) 2_655 . ?
O19 Mn1 N21 89.57(7) 4 . ?
O28 Mn1 N21 95.18(7) 4_566 . ?
O30 Mn1 N21 89.86(7) . . ?
N11 Mn1 N21 178.00(6) . . ?
C17 O18 Mn1 170.58(16) . 2_645 ?
C17 O19 Mn1 140.48(14) . 4_556 ?
C27 O28 Mn1 140.20(13) . 4_565 ?
Mn1 O30 H30A 125.6 . . ?
Mn1 O30 H30B 116.3 . . ?
H30A O30 H30B 111.2 . . ?
C16 N11 C12 117.13(17) . . ?
C16 N11 Mn1 122.39(13) . . ?
C12 N11 Mn1 120.24(14) . . ?
C26 N21 C22 116.48(18) . . ?
C26 N21 Mn1 124.55(14) . . ?
C22 N21 Mn1 118.86(14) . . ?
N11 C12 C13 123.2(2) . . ?
N11 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
C12 C13 C14 119.26(19) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 117.98(18) . . ?
C15 C14 C17 121.22(17) . . ?
C13 C14 C17 120.79(18) . . ?
C14 C15 C16 119.25(19) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N11 C16 C15 123.21(19) . . ?
N11 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
O18 C17 O19 127.14(19) . . ?
O18 C17 C14 116.73(18) . . ?
O19 C17 C14 116.13(17) . . ?
N21 C22 C23 123.5(2) . . ?
N21 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
C22 C23 C24 119.7(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 117.15(19) . . ?
C23 C24 C27 120.88(19) . . ?
C25 C24 C27 121.91(18) . . ?
C26 C25 C24 119.3(2) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
N21 C26 C25 123.8(2) . . ?
N21 C26 H26 118.1 . . ?
C25 C26 H26 118.1 . . ?
O28 C27 O29 126.31(18) . . ?
O28 C27 C24 115.90(17) . . ?
O29 C27 C24 117.79(17) . . ?
C32 O31 H31 107.1 . . ?
O31 C32 C33 117.4(4) . . ?
O31 C32 H32A 107.9 . . ?
C33 C32 H32A 107.9 . . ?
O31 C32 H32B 107.9 . . ?
C33 C32 H32B 107.9 . . ?
H32A C32 H32B 107.2 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
O18 Mn1 N11 C16 50.48(18) 2_655 . . . ?
O19 Mn1 N11 C16 -48.67(18) 4 . . . ?
O28 Mn1 N11 C16 140.43(18) 4_566 . . . ?
O30 Mn1 N11 C16 -132.39(18) . . . . ?
N21 Mn1 N11 C16 -87.8(18) . . . . ?
O18 Mn1 N11 C12 -135.22(19) 2_655 . . . ?
O19 Mn1 N11 C12 125.62(19) 4 . . . ?
O28 Mn1 N11 C12 -45.27(18) 4_566 . . . ?
O30 Mn1 N11 C12 41.91(19) . . . . ?
N21 Mn1 N11 C12 86.5(18) . . . . ?
O18 Mn1 N21 C26 43.40(19) 2_655 . . . ?
O19 Mn1 N21 C26 142.59(19) 4 . . . ?
O28 Mn1 N21 C26 -46.6(2) 4_566 . . . ?
O30 Mn1 N21 C26 -133.71(19) . . . . ?
N11 Mn1 N21 C26 -18E1(7) . . . . ?
O18 Mn1 N21 C22 -132.64(18) 2_655 . . . ?
O19 Mn1 N21 C22 -33.44(18) 4 . . . ?
O28 Mn1 N21 C22 137.33(18) 4_566 . . . ?
O30 Mn1 N21 C22 50.26(18) . . . . ?
N11 Mn1 N21 C22 5.7(19) . . . . ?
C16 N11 C12 C13 0.1(4) . . . . ?
Mn1 N11 C12 C13 -174.5(2) . . . . ?
N11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C12 C13 C14 C17 178.7(2) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C17 C14 C15 C16 -179.02(19) . . . . ?
C12 N11 C16 C15 -0.4(3) . . . . ?
Mn1 N11 C16 C15 174.06(17) . . . . ?
C14 C15 C16 N11 0.5(4) . . . . ?
Mn1 O18 C17 O19 19.3(13) 2_645 . . . ?
Mn1 O18 C17 C14 -161.2(10) 2_645 . . . ?
Mn1 O19 C17 O18 17.3(4) 4_556 . . . ?
Mn1 O19 C17 C14 -162.24(16) 4_556 . . . ?
C15 C14 C17 O18 1.3(3) . . . . ?
C13 C14 C17 O18 -177.3(2) . . . . ?
C15 C14 C17 O19 -179.1(2) . . . . ?
C13 C14 C17 O19 2.2(3) . . . . ?
C26 N21 C22 C23 0.4(4) . . . . ?
Mn1 N21 C22 C23 176.8(2) . . . . ?
N21 C22 C23 C24 -1.6(4) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C22 C23 C24 C27 -176.2(2) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C27 C24 C25 C26 177.8(2) . . . . ?
C22 N21 C26 C25 1.3(4) . . . . ?
Mn1 N21 C26 C25 -174.80(18) . . . . ?
C24 C25 C26 N21 -1.8(4) . . . . ?
Mn1 O28 C27 O29 32.2(4) 4_565 . . . ?
Mn1 O28 C27 C24 -147.45(17) 4_565 . . . ?
C23 C24 C27 O28 150.5(2) . . . . ?
C25 C24 C27 O28 -26.8(3) . . . . ?
C23 C24 C27 O29 -29.2(3) . . . . ?
C25 C24 C27 O29 153.6(2) . . . . ?

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
O30 H30A O29 0.76 2.03 2.786(2) 169 3_755
O30 H30B O31 0.84 1.84 2.666(3) 171.2 .
O31 H31 O29 0.98 1.75 2.719(3) 167.8 4_566

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 938235'
