# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   9.9301(13)
_cell_length_b                   17.060(2)
_cell_length_c                   10.008(2)
_cell_angle_alpha                90.0
_cell_angle_beta                 109.004(18)
_cell_angle_gamma                90.0
_cell_volume                     1603.0(5)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Mn 0.3368 0.7283 11.2819 5.3409 7.3573 0.3432 3.0193 17.8674 2.2441 83.7543
1.0896 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C35 H35 Cl5 MN2.50 N7.50 
# Dc =      1.81 Fooo =    740.00 Mu =     14.36 M =    437.65
# Found Formula = C30 H30 Cl4 MN2 N6 
# Dc =      1.50 FOOO =    740.00 Mu =     11.52 M =    363.14

_chemical_formula_sum            'C30 H30 Cl4 MN2 N6'
_chemical_formula_moiety         'C30 H30 Cl4 MN2 N6'
_chemical_compound_source        ?
_chemical_formula_weight         726.28


_cell_measurement_reflns_used    2425
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29
_cell_measurement_temperature    150

_exptl_crystal_description       hexagonal
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.162
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_max          0.247

_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    1.152

# Sheldrick geometric approximatio 0.80 0.83 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.83
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            5610
_reflns_number_total             3034
_diffrn_reflns_av_R_equivalents  0.051
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3034 
# Theoretical number of reflections is about 8689 


_diffrn_reflns_theta_min         3.465
_diffrn_reflns_theta_max         29.403
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        25.286
_diffrn_measured_fraction_theta_full 0.975


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -13
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.72
_refine_diff_density_max         0.98


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_number_parameters     190
_oxford_refine_ls_R_factor_ref   0.0526
_refine_ls_wR_factor_ref         0.0648
_refine_ls_goodness_of_fit_ref   0.9233
_refine_ls_shift/su_max          0.0005443
_refine_ls_shift/su_mean         0.0000214


# The values computed from all data 
_oxford_reflns_number_all        3019
_refine_ls_R_factor_all          0.0709
_refine_ls_wR_factor_all         0.0874

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2523
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_gt          0.0711

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 6.08 4.39 3.80 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.2238(3) 0.52431(16) 0.3783(4) 0.0216 1.0000 Uani . . . . . .
C2 C 0.3238(3) 0.4774(2) 0.4627(4) 0.0226 1.0000 Uani . . . . . .
C3 C 0.3438(4) 0.4699(2) 0.6047(5) 0.0333 1.0000 Uani . . . . . .
C4 C 0.2589(4) 0.5119(3) 0.6648(5) 0.0309 1.0000 Uani . . . . . .
C5 C 0.1544(4) 0.5608(2) 0.5762(5) 0.0264 1.0000 Uani . . . . . .
C6 C 0.1406(3) 0.56547(19) 0.4347(4) 0.0201 1.0000 Uani . . . . . .
C7 C 0.0292(3) 0.6175(2) 0.3327(4) 0.0217 1.0000 Uani . . . . . .
N3 N 0.0800(3) 0.64521(16) 0.2197(3) 0.0182 1.0000 Uani . . . . . .
C9 C -0.0385(3) 0.67992(19) 0.1017(4) 0.0217 1.0000 Uani . . . . . .
C10 C -0.1054(3) 0.7476(2) 0.1450(5) 0.0290 1.0000 Uani . . . . . .
C11 C -0.1530(4) 0.7997(2) 0.1921(5) 0.0351 1.0000 Uani . . . . . .
C12 C 0.1973(3) 0.70221(19) 0.2770(4) 0.0209 1.0000 Uani . . . . . .
C13 C 0.3000(3) 0.70239(19) 0.1951(4) 0.0184 1.0000 Uani . . . . . .
C14 C 0.3817(3) 0.76864(19) 0.1943(4) 0.0245 1.0000 Uani . . . . . .
C15 C 0.4843(4) 0.7640(2) 0.1271(5) 0.0271 1.0000 Uani . . . . . .
C16 C 0.5019(4) 0.6945(2) 0.0649(4) 0.0278 1.0000 Uani . . . . . .
C17 C 0.4163(3) 0.6316(2) 0.0700(4) 0.0225 1.0000 Uani . . . . . .
Cl3 Cl 0.34642(8) 0.43283(5) 0.13539(11) 0.0235 1.0000 Uani . . . . . .
Cl1 Cl 0.04960(8) 0.54940(5) -0.12121(10) 0.0201 1.0000 Uani . . . . . .
Mn1 Mn 0.17368(5) 0.53230(3) 0.13962(6) 0.0171 1.0000 Uani . . . . . .
N2 N 0.3179(3) 0.63499(16) 0.1356(3) 0.0189 1.0000 Uani . . . . . .
H21 H 0.3819 0.4490 0.4200 0.0276 1.0000 Uiso . . . . . .
H31 H 0.4164 0.4368 0.6620 0.0415 1.0000 Uiso . . . . . .
H41 H 0.2727 0.5076 0.7635 0.0405 1.0000 Uiso . . . . . .
H51 H 0.0927 0.5906 0.6121 0.0336 1.0000 Uiso . . . . . .
H72 H 0.0069 0.6621 0.3851 0.0274 1.0000 Uiso . . . . . .
H71 H -0.0576 0.5870 0.2880 0.0268 1.0000 Uiso . . . . . .
H91 H -0.0013 0.6974 0.0252 0.0263 1.0000 Uiso . . . . . .
H92 H -0.1114 0.6404 0.0635 0.0267 1.0000 Uiso . . . . . .
H111 H -0.1879 0.8426 0.2306 0.0446 1.0000 Uiso . . . . . .
H122 H 0.1573 0.7542 0.2738 0.0265 1.0000 Uiso . . . . . .
H121 H 0.2499 0.6882 0.3769 0.0270 1.0000 Uiso . . . . . .
H141 H 0.3686 0.8162 0.2386 0.0294 1.0000 Uiso . . . . . .
H151 H 0.5422 0.8077 0.1257 0.0322 1.0000 Uiso . . . . . .
H161 H 0.5699 0.6890 0.0181 0.0329 1.0000 Uiso . . . . . .
H171 H 0.4266 0.5863 0.0259 0.0266 1.0000 Uiso . . . . . .
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
N1 0.0185(13) 0.0210(14) 0.024(2) -0.0029(13) 0.0051(12) -0.0014(10)
C2 0.0168(15) 0.0321(19) 0.016(3) 0.0030(17) 0.0008(13) -0.0027(12)
C3 0.0214(18) 0.039(2) 0.034(3) 0.007(2) 0.0007(16) -0.0037(14)
C4 0.0281(19) 0.039(2) 0.025(3) -0.0018(19) 0.0079(16) -0.0119(15)
C5 0.0272(18) 0.0322(19) 0.022(3) -0.0025(18) 0.0115(15) -0.0103(14)
C6 0.0202(15) 0.0211(16) 0.021(3) -0.0045(15) 0.0092(14) -0.0078(12)
C7 0.0220(15) 0.0233(16) 0.023(3) -0.0031(16) 0.0123(14) -0.0004(13)
N3 0.0151(12) 0.0171(13) 0.021(2) -0.0038(12) 0.0033(11) 0.0003(9)
C9 0.0206(15) 0.0190(15) 0.023(3) -0.0058(15) 0.0043(13) 0.0024(12)
C10 0.0172(15) 0.0222(17) 0.042(3) -0.0015(17) 0.0022(14) 0.0009(12)
C11 0.0248(18) 0.030(2) 0.044(3) -0.0122(19) 0.0022(16) 0.0036(14)
C12 0.0168(14) 0.0173(15) 0.028(2) -0.0042(15) 0.0059(13) -0.0026(11)
C13 0.0149(14) 0.0195(15) 0.018(2) 0.0024(15) 0.0009(12) 0.0000(11)
C14 0.0215(15) 0.0187(16) 0.031(3) -0.0029(16) 0.0062(14) -0.0011(12)
C15 0.0254(17) 0.0255(18) 0.030(3) 0.0026(17) 0.0086(15) -0.0070(13)
C16 0.0200(15) 0.0313(19) 0.034(3) 0.0013(17) 0.0118(15) 0.0001(13)
C17 0.0207(15) 0.0207(16) 0.026(3) -0.0003(15) 0.0071(14) 0.0005(12)
Cl3 0.0186(4) 0.0194(4) 0.0324(7) -0.0018(4) 0.0080(3) 0.0035(3)
Cl1 0.0172(4) 0.0212(4) 0.0208(6) 0.0006(4) 0.0048(3) -0.0025(3)
Mn1 0.0137(3) 0.0148(3) 0.0217(4) -0.0016(2) 0.0041(2) 0.00028(16)
N2 0.0151(12) 0.0210(14) 0.019(2) -0.0025(13) 0.0039(11) -0.0007(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.507(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N3 . Mn1 . 2.388(3) yes
C9 . C10 . 1.467(5) yes
C9 . H91 . 0.997 no
C9 . H92 . 0.971 no
C10 . C11 . 1.175(6) yes
C11 . H111 . 0.945 no
C12 . C13 . 1.502(5) yes
C12 . H122 . 0.968 no
C12 . H121 . 0.994 no
C13 . C14 . 1.393(4) yes
C13 . N2 . 1.333(4) yes
C14 . C15 . 1.394(5) yes
C14 . H141 . 0.953 no
C15 . C16 . 1.377(5) yes
C15 . H151 . 0.944 no
C16 . C17 . 1.379(5) yes
C16 . H161 . 0.942 no
C17 . N2 . 1.345(4) yes
C17 . H171 . 0.913 no
Cl3 . Mn1 . 2.4230(11) yes
Cl1 . Mn1 2_565 2.5742(13) yes
Cl1 . Mn1 . 2.5145(16) yes
Mn1 . N2 . 2.272(3) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 118.7(4) yes
C2 . N1 . Mn1 . 124.1(3) yes
C6 . N1 . Mn1 . 117.1(2) yes
N1 . C2 . C3 . 122.4(4) yes
N1 . C2 . H21 . 117.0 no
C3 . C2 . H21 . 120.7 no
C2 . C3 . C4 . 119.8(4) yes
C2 . C3 . H31 . 120.4 no
C4 . C3 . H31 . 119.8 no
C3 . C4 . C5 . 117.6(4) yes
C3 . C4 . H41 . 120.4 no
C5 . C4 . H41 . 122.0 no
C4 . C5 . C6 . 119.4(4) yes
C4 . C5 . H51 . 120.9 no
C6 . C5 . H51 . 119.7 no
C5 . C6 . N1 . 122.2(3) yes
C5 . C6 . C7 . 122.0(3) yes
N1 . C6 . C7 . 115.9(3) yes
C6 . C7 . N3 . 110.5(3) yes
C6 . C7 . H72 . 109.4 no
N3 . C7 . H72 . 110.9 no
C6 . C7 . H71 . 109.6 no
N3 . C7 . H71 . 106.9 no
H72 . C7 . H71 . 109.5 no
C7 . N3 . C9 . 111.1(3) yes
C7 . N3 . C12 . 109.8(3) yes
C9 . N3 . C12 . 111.3(3) yes
C7 . N3 . Mn1 . 105.66(19) yes
C9 . N3 . Mn1 . 110.3(2) yes
C12 . N3 . Mn1 . 108.41(19) yes
N3 . C9 . C10 . 113.3(3) yes
N3 . C9 . H91 . 109.5 no
C10 . C9 . H91 . 107.9 no
N3 . C9 . H92 . 109.3 no
C10 . C9 . H92 . 108.1 no
H91 . C9 . H92 . 108.7 no
C9 . C10 . C11 . 173.9(5) yes
C10 . C11 . H111 . 177.8 no
N3 . C12 . C13 . 112.2(3) yes
N3 . C12 . H122 . 109.0 no
C13 . C12 . H122 . 108.9 no
N3 . C12 . H121 . 108.7 no
C13 . C12 . H121 . 108.8 no
H122 . C12 . H121 . 109.2 no
C12 . C13 . C14 . 120.3(3) yes
C12 . C13 . N2 . 117.1(3) yes
C14 . C13 . N2 . 122.3(3) yes
C13 . C14 . C15 . 118.4(3) yes
C13 . C14 . H141 . 121.3 no
C15 . C14 . H141 . 120.3 no
C14 . C15 . C16 . 119.2(3) yes
C14 . C15 . H151 . 120.4 no
C16 . C15 . H151 . 120.4 no
C15 . C16 . C17 . 118.8(3) yes
C15 . C16 . H161 . 121.7 no
C17 . C16 . H161 . 119.4 no
C16 . C17 . N2 . 122.7(3) yes
C16 . C17 . H171 . 118.3 no
N2 . C17 . H171 . 119.1 no
Mn1 2_565 Cl1 . Mn1 . 97.52(4) yes
Cl1 . Mn1 . Cl1 2_565 82.48(5) yes
Cl1 . Mn1 . N1 . 163.87(7) yes
Cl1 2_565 Mn1 . N1 . 86.09(8) yes
Cl1 . Mn1 . Cl3 . 99.99(5) yes
Cl1 2_565 Mn1 . Cl3 . 102.57(4) yes
N1 . Mn1 . Cl3 . 93.56(8) yes
Cl1 . Mn1 . N3 . 98.17(8) yes
Cl1 2_565 Mn1 . N3 . 92.30(8) yes
N1 . Mn1 . N3 . 70.89(10) yes
Cl3 . Mn1 . N3 . 157.83(7) yes
Cl1 . Mn1 . N2 . 89.48(8) yes
Cl1 2_565 Mn1 . N2 . 161.76(7) yes
N1 . Mn1 . N2 . 98.09(11) yes
Cl3 . Mn1 . N2 . 94.91(8) yes
N3 . Mn1 . N2 . 72.59(10) yes
Mn1 . N2 . C17 . 122.6(2) yes
Mn1 . N2 . C13 . 118.7(2) yes
C17 . N2 . C13 . 118.6(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/12/11 at 09:46:18
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/12/11 at 09:46:18
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 905065'
#######################################################################
#
#                 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_uc198

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 '[di-mu-bromo-dibromo-bis(N,N-bis((pyridin-2-yl)methyl)prop-2-yn-1-amine)]dimanganese(II)'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 Br4 Mn2 N6'
_chemical_formula_sum            'C30 H30 Br4 Mn2 N6'
_chemical_formula_weight         904.08

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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.1360(4)
_cell_length_b                   17.2803(6)
_cell_length_c                   10.2664(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.062(2)
_cell_angle_gamma                90.00
_cell_volume                     1699.59(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    27213
_cell_measurement_theta_min      0.952034
_cell_measurement_theta_max      25.6792

_exptl_crystal_description       paralelepipedes
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             884
_exptl_absorpt_coefficient_mu    5.474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.624
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'

_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  'Bruker APEX2 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26597
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.79
_reflns_number_total             3268
_reflns_number_gt                2741
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'


_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)+(0.0252P)²+1.1599P] where P=(Fo²+2Fc²)/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_number_reflns         3268
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0578
_refine_ls_wR_factor_gt          0.0545
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Br1 Br 1.05129(3) -0.057041(16) 0.87687(3) 0.04124(9) Uani 1 1 d . . .
Br3 Br 0.64462(3) -0.067707(16) 0.87402(3) 0.04489(9) Uani 1 1 d . . .
Mn1 Mn 0.82369(4) 0.03340(2) 0.85446(4) 0.03258(10) Uani 1 1 d . . .
N1 N 0.6872(2) 0.13701(12) 0.8552(2) 0.0372(5) Uani 1 1 d . . .
N2 N 0.7732(2) 0.02023(13) 0.6234(2) 0.0413(5) Uani 1 1 d . . .
N3 N 0.9201(2) 0.14121(12) 0.7709(2) 0.0374(5) Uani 1 1 d . . .
C1 C 0.5915(3) 0.13720(17) 0.9202(3) 0.0444(7) Uani 1 1 d . . .
H1 H 0.5774 0.0920 0.9629 0.053 Uiso 1 1 calc R . .
C2 C 0.5137(3) 0.20137(18) 0.9260(3) 0.0527(8) Uani 1 1 d . . .
H2 H 0.4473 0.1995 0.9706 0.063 Uiso 1 1 calc R . .
C3 C 0.5362(3) 0.26823(18) 0.8648(3) 0.0570(8) Uani 1 1 d . . .
H3 H 0.4846 0.3124 0.8668 0.068 Uiso 1 1 calc R . .
C4 C 0.6354(3) 0.26949(16) 0.8006(3) 0.0473(7) Uani 1 1 d . . .
H4 H 0.6531 0.3148 0.7603 0.057 Uiso 1 1 calc R . .
C5 C 0.7085(3) 0.20274(15) 0.7965(3) 0.0370(6) Uani 1 1 d . . .
C6 C 0.8085(3) 0.19916(15) 0.7161(3) 0.0422(7) Uani 1 1 d . . .
H6A H 0.7571 0.1867 0.6209 0.051 Uiso 1 1 calc R . .
H6B H 0.8507 0.2497 0.7177 0.051 Uiso 1 1 calc R . .
C7 C 0.9645(3) 0.11036(17) 0.6589(3) 0.0472(7) Uani 1 1 d . . .
H7A H 1.0494 0.0805 0.6974 0.057 Uiso 1 1 calc R . .
H7B H 0.9846 0.1529 0.6066 0.057 Uiso 1 1 calc R . .
C8 C 0.8528(3) 0.05969(16) 0.5646(3) 0.0437(7) Uani 1 1 d . . .
C9 C 0.8353(4) 0.0533(2) 0.4263(3) 0.0569(9) Uani 1 1 d . . .
H9 H 0.8920 0.0814 0.3882 0.068 Uiso 1 1 calc R . .
C11 C 0.6758(3) -0.02680(19) 0.5434(3) 0.0534(8) Uani 1 1 d . . .
H11 H 0.6178 -0.0563 0.5772 0.064 Uiso 1 1 d R . .
C12 C 1.0397(3) 0.17464(17) 0.8816(3) 0.0493(7) Uani 1 1 d . . .
H12A H 1.0066 0.1947 0.9536 0.059 Uiso 1 1 calc R . .
H12B H 1.1064 0.1339 0.9215 0.059 Uiso 1 1 calc R . .
C13 C 1.1107(3) 0.23679(19) 0.8338(4) 0.0631(9) Uani 1 1 d . . .
C14 C 1.1627(4) 0.2854(2) 0.7893(4) 0.0896(14) Uani 1 1 d . . .
H14 H 1.2044 0.3244 0.7537 0.107 Uiso 1 1 calc R . .
C16 C 0.6541(4) -0.0354(2) 0.4046(3) 0.0669(10) Uani 1 1 d . . .
H16 H 0.5865 -0.0702 0.3543 0.080 Uiso 1 1 d R . .
C17 C 0.7343(4) 0.0057(2) 0.3454(3) 0.0673(10) Uani 1 1 d . . .
H17 H 0.7201 0.0019 0.2514 0.081 Uiso 1 1 d R . .

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
Br1 0.04308(17) 0.04571(16) 0.03437(15) 0.00083(11) 0.01188(12) 0.00412(12)
Br3 0.04090(17) 0.03896(16) 0.05624(19) 0.00206(12) 0.01784(13) -0.00613(12)
Mn1 0.0333(2) 0.0315(2) 0.0327(2) 0.00442(15) 0.01036(17) 0.00058(16)
N1 0.0356(12) 0.0362(12) 0.0393(12) 0.0041(9) 0.0114(10) 0.0033(10)
N2 0.0404(13) 0.0485(14) 0.0345(12) 0.0049(10) 0.0115(10) 0.0039(11)
N3 0.0352(12) 0.0364(12) 0.0399(12) 0.0088(9) 0.0114(10) 0.0034(10)
C1 0.0430(16) 0.0452(16) 0.0463(16) 0.0033(12) 0.0164(13) 0.0026(13)
C2 0.0484(18) 0.061(2) 0.0522(18) 0.0019(15) 0.0215(15) 0.0141(15)
C3 0.061(2) 0.0474(18) 0.062(2) 0.0015(15) 0.0185(17) 0.0221(15)
C4 0.0543(19) 0.0355(15) 0.0475(17) 0.0063(12) 0.0102(14) 0.0082(13)
C5 0.0354(15) 0.0360(14) 0.0342(14) 0.0019(11) 0.0038(11) 0.0012(11)
C6 0.0433(16) 0.0370(15) 0.0458(16) 0.0125(12) 0.0141(13) 0.0049(12)
C7 0.0454(17) 0.0468(17) 0.0565(19) 0.0157(14) 0.0265(15) 0.0066(13)
C8 0.0450(17) 0.0488(17) 0.0394(16) 0.0103(12) 0.0167(13) 0.0179(13)
C9 0.062(2) 0.071(2) 0.0458(18) 0.0138(16) 0.0283(17) 0.0262(18)
C11 0.0481(18) 0.066(2) 0.0428(17) -0.0006(15) 0.0101(14) 0.0006(16)
C12 0.0429(17) 0.0439(17) 0.0550(19) 0.0131(13) 0.0076(14) -0.0050(13)
C13 0.0430(19) 0.053(2) 0.080(2) 0.0220(17) 0.0012(17) -0.0066(15)
C14 0.058(2) 0.074(3) 0.116(3) 0.049(2) 0.000(2) -0.020(2)
C16 0.055(2) 0.087(3) 0.047(2) -0.0154(18) 0.0007(17) 0.0098(19)
C17 0.069(2) 0.096(3) 0.0371(18) 0.0043(18) 0.0177(18) 0.033(2)

_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
Br1 Mn1 2.6641(5) 3_757 ?
Br1 Mn1 2.7333(5) . ?
Br3 Mn1 2.5740(5) . ?
Mn1 N1 2.264(2) . ?
Mn1 N2 2.269(2) . ?
Mn1 N3 2.389(2) . ?
Mn1 Br1 2.6641(5) 3_757 ?
N1 C5 1.337(3) . ?
N1 C1 1.344(3) . ?
N2 C11 1.334(4) . ?
N2 C8 1.340(4) . ?
N3 C7 1.465(3) . ?
N3 C6 1.477(3) . ?
N3 C12 1.481(3) . ?
C1 C2 1.374(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.503(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.507(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.377(4) . ?
C9 C17 1.364(5) . ?
C9 H9 0.9300 . ?
C11 C16 1.378(4) . ?
C11 H11 0.9270 . ?
C12 C13 1.464(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.163(5) . ?
C14 H14 0.9300 . ?
C16 C17 1.363(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9299 . ?

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
Mn1 Br1 Mn1 95.880(14) 3_757 . ?
N1 Mn1 N2 98.84(8) . . ?
N1 Mn1 N3 72.95(8) . . ?
N2 Mn1 N3 71.45(8) . . ?
N1 Mn1 Br3 95.11(6) . . ?
N2 Mn1 Br3 95.14(6) . . ?
N3 Mn1 Br3 159.85(5) . . ?
N1 Mn1 Br1 87.70(5) . 3_757 ?
N2 Mn1 Br1 165.10(6) . 3_757 ?
N3 Mn1 Br1 98.05(5) . 3_757 ?
Br3 Mn1 Br1 97.610(15) . 3_757 ?
N1 Mn1 Br1 162.13(6) . . ?
N2 Mn1 Br1 85.78(6) . . ?
N3 Mn1 Br1 92.47(5) . . ?
Br3 Mn1 Br1 101.689(15) . . ?
Br1 Mn1 Br1 84.120(14) 3_757 . ?
C5 N1 C1 118.1(2) . . ?
C5 N1 Mn1 118.75(17) . . ?
C1 N1 Mn1 122.98(18) . . ?
C11 N2 C8 117.8(2) . . ?
C11 N2 Mn1 124.95(19) . . ?
C8 N2 Mn1 117.14(19) . . ?
C7 N3 C6 109.9(2) . . ?
C7 N3 C12 111.1(2) . . ?
C6 N3 C12 111.2(2) . . ?
C7 N3 Mn1 105.33(16) . . ?
C6 N3 Mn1 108.26(15) . . ?
C12 N3 Mn1 110.93(15) . . ?
N1 C1 C2 122.8(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 C6 116.8(2) . . ?
C4 C5 C6 121.1(2) . . ?
N3 C6 C5 112.8(2) . . ?
N3 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
N3 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N3 C7 C8 110.9(2) . . ?
N3 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 122.0(3) . . ?
N2 C8 C7 116.3(2) . . ?
C9 C8 C7 121.7(3) . . ?
C17 C9 C8 119.6(3) . . ?
C17 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N2 C11 C16 122.6(3) . . ?
N2 C11 H11 122.5 . . ?
C16 C11 H11 114.9 . . ?
C13 C12 N3 113.4(2) . . ?
C13 C12 H12A 108.9 . . ?
N3 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
N3 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 176.6(4) . . ?
C13 C14 H14 180.0 . . ?
C17 C16 C11 119.2(3) . . ?
C17 C16 H16 121.8 . . ?
C11 C16 H16 119.0 . . ?
C16 C17 C9 118.8(3) . . ?
C16 C17 H17 120.9 . . ?
C9 C17 H17 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 911104'
#######################################################################
#
#                 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_1

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.2568(3)
_cell_length_b                   18.4512(6)
_cell_length_c                   18.6889(6)
_cell_angle_alpha                90.0
_cell_angle_beta                 95.592(3)
_cell_angle_gamma                90.0
_cell_volume                     3520.0(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1 '
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Mn 0.3368 0.7283 11.2819 5.3409 7.3573 0.3432 3.0193 17.8674 2.2441 83.7543
1.0896 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C30 H28 MN3 N12 
# Dc =      1.26 Fooo =   1560.00 Mu =      7.54 M =    333.24
# Found Formula = C28 H32 MN3 N30 
# Dc =      1.43 FOOO =   1560.00 Mu =      7.70 M =    379.28

_chemical_formula_sum            'C28 H32 MN2 N20'
_chemical_formula_moiety         'C28 H32 MN2 N20'
_chemical_compound_source        ?
_chemical_formula_weight         758.55


_cell_measurement_reflns_used    11318
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29
_cell_measurement_temperature    293

_exptl_crystal_description       'flat lozenge'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_min          0.151
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_max          0.569

_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    0.770

# Sheldrick geometric approximatio 0.78 0.89 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            23027
_reflns_number_total             4407
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4407 
# Theoretical number of reflections is about 9482 


_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         29.223
_diffrn_measured_fraction_theta_max 0.971

_diffrn_reflns_theta_full        25.132
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              25
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.30


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     12
_refine_ls_number_parameters     226
_oxford_refine_ls_R_factor_ref   0.0312
_refine_ls_wR_factor_ref         0.0353
_refine_ls_goodness_of_fit_ref   1.0832
_refine_ls_shift/su_max          0.0008774
_refine_ls_shift/su_mean         0.0000290


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4398
_refine_ls_R_factor_all          0.0462
_refine_ls_wR_factor_all         0.0447

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3649
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_gt          0.0365

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 4.27 1.41 3.41 0.823 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Mn1 Mn 0.28139(2) 0.234370(12) 0.411321(12) 0.0350 1.0000 Uani . . . . . .
N1 N 0.26540(12) 0.31879(7) 0.32063(7) 0.0396 1.0000 Uani . . . . . .
C3 C 0.17233(15) 0.31715(11) 0.26521(9) 0.0484 1.0000 Uani . . . . . .
C4 C 0.15931(19) 0.37108(13) 0.21404(11) 0.0622 1.0000 Uani . . . . . .
C5 C 0.2440(2) 0.42809(13) 0.21960(13) 0.0701 1.0000 Uani . . . . . .
C6 C 0.33856(19) 0.43155(10) 0.27661(11) 0.0565 1.0000 Uani . . . . . .
C7 C 0.34696(15) 0.37578(8) 0.32670(9) 0.0404 1.0000 Uani . . . . . .
C8 C 0.44749(16) 0.37731(8) 0.39027(9) 0.0433 1.0000 Uani . . . . . .
N3 N 0.48748(12) 0.30339(7) 0.41227(7) 0.0362 1.0000 Uani . . . . . .
C10 C 0.55839(16) 0.30243(11) 0.48485(9) 0.0482 1.0000 Uani . . . . . .
C11 C 0.67753(19) 0.34812(13) 0.49067(10) 0.0585 1.0000 Uani . . . . . .
C12 C 0.7698(2) 0.38535(16) 0.49239(14) 0.0803 1.0000 Uani . . . . . .
C13 C 0.56653(14) 0.26914(9) 0.35974(8) 0.0399 1.0000 Uani . . . . . .
C14 C 0.54123(15) 0.18932(8) 0.35806(8) 0.0387 1.0000 Uani . . . . . .
N2 N 0.43146(14) 0.16121(7) 0.37673(8) 0.0445 1.0000 Uani . . . . . .
C16 C 0.4436(2) 0.08756(10) 0.36983(11) 0.0542 1.0000 Uani . . . . . .
C17 C 0.5587(2) 0.07132(10) 0.34533(11) 0.0580 1.0000 Uani . . . . . .
N18 N 0.62145(15) 0.13681(8) 0.33790(8) 0.0490 1.0000 Uani . . . . . .
C19 C 0.7520(2) 0.14531(14) 0.31475(14) 0.0707 1.0000 Uani . . . . . .
N12 N 0.19694(15) 0.31616(7) 0.47973(7) 0.0455 1.0000 Uani . . . . . .
N31 N 0.13496(15) 0.36789(8) 0.45876(8) 0.0472 1.0000 Uani . U . . . .
N32 N 0.0766(2) 0.41755(12) 0.43809(12) 0.0853 1.0000 Uani . U . . . .
N9 N 0.11322(15) 0.17959(9) 0.36186(9) 0.0580 1.0000 Uani . . . . . .
N34 N 0.09380(15) 0.11772(10) 0.35644(11) 0.0624 1.0000 Uani . U . . . .
N35 N 0.0719(3) 0.05739(14) 0.3500(2) 0.1292 1.0000 Uani . U . . . .
H31 H 0.1135 0.2757 0.2623 0.0596 1.0000 Uiso R . . . . .
H41 H 0.0908 0.3673 0.1744 0.0766 1.0000 Uiso R . . . . .
H51 H 0.2393 0.4665 0.1842 0.0844 1.0000 Uiso R . . . . .
H61 H 0.3972 0.4734 0.2808 0.0704 1.0000 Uiso R . . . . .
H82 H 0.4094 0.4009 0.4313 0.0532 1.0000 Uiso R . . . . .
H81 H 0.5241 0.4059 0.3786 0.0533 1.0000 Uiso R . . . . .
H102 H 0.4981 0.3209 0.5194 0.0591 1.0000 Uiso R . . . . .
H101 H 0.5833 0.2505 0.4973 0.0600 1.0000 Uiso R . . . . .
H121 H 0.8466 0.4171 0.4936 0.0964 1.0000 Uiso R . . . . .
H131 H 0.6609 0.2797 0.3717 0.0493 1.0000 Uiso R . . . . .
H132 H 0.5411 0.2907 0.3114 0.0490 1.0000 Uiso R . . . . .
H161 H 0.3765 0.0525 0.3817 0.0669 1.0000 Uiso R . . . . .
H171 H 0.5945 0.0245 0.3352 0.0726 1.0000 Uiso R . . . . .
H192 H 0.7976 0.1000 0.3216 0.1105 1.0000 Uiso R . . . . .
H193 H 0.7981 0.1840 0.3446 0.1097 1.0000 Uiso R . . . . .
H191 H 0.7448 0.1601 0.2642 0.1099 1.0000 Uiso R . . . . .
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
Mn1 0.03440(12) 0.03585(12) 0.03486(12) 0.00158(9) 0.00405(8) -0.00400(9)
N1 0.0331(6) 0.0469(7) 0.0388(6) 0.0063(5) 0.0042(5) 0.0036(5)
C3 0.0344(7) 0.0667(11) 0.0438(8) 0.0052(8) 0.0019(6) 0.0063(7)
C4 0.0445(9) 0.0911(15) 0.0501(10) 0.0198(10) 0.0004(8) 0.0194(10)
C5 0.0599(11) 0.0780(14) 0.0742(13) 0.0378(11) 0.0158(10) 0.0264(11)
C6 0.0552(10) 0.0472(9) 0.0690(12) 0.0213(9) 0.0170(9) 0.0127(8)
C7 0.0384(7) 0.0360(7) 0.0484(8) 0.0064(6) 0.0122(6) 0.0064(6)
C8 0.0436(8) 0.0347(7) 0.0523(9) -0.0013(6) 0.0082(7) -0.0058(6)
N3 0.0338(6) 0.0396(6) 0.0354(6) -0.0006(5) 0.0040(5) -0.0020(5)
C10 0.0424(8) 0.0632(11) 0.0383(8) -0.0010(7) 0.0004(6) -0.0066(7)
C11 0.0493(10) 0.0789(13) 0.0456(9) -0.0029(9) -0.0050(7) -0.0100(9)
C12 0.0596(13) 0.1071(19) 0.0702(14) 0.0037(13) -0.0143(10) -0.0308(13)
C13 0.0361(7) 0.0462(8) 0.0383(7) 0.0018(6) 0.0083(6) -0.0012(6)
C14 0.0395(7) 0.0440(8) 0.0322(7) -0.0014(6) 0.0009(6) 0.0066(6)
N2 0.0461(7) 0.0400(7) 0.0474(7) -0.0057(6) 0.0045(6) -0.0031(5)
C16 0.0631(11) 0.0430(9) 0.0575(10) -0.0092(8) 0.0102(8) -0.0080(8)
C17 0.0750(12) 0.0409(9) 0.0594(11) -0.0046(8) 0.0126(9) 0.0063(8)
N18 0.0508(8) 0.0506(8) 0.0461(8) 0.0005(6) 0.0073(6) 0.0102(6)
C19 0.0618(12) 0.0733(13) 0.0810(15) 0.0037(11) 0.0278(11) 0.0173(10)
N12 0.0564(8) 0.0417(7) 0.0394(7) 0.0070(6) 0.0102(6) 0.0106(6)
N31 0.0509(8) 0.0461(8) 0.0457(7) 0.0090(6) 0.0104(6) 0.0066(6)
N32 0.0976(15) 0.0730(12) 0.0870(14) 0.0284(11) 0.0168(12) 0.0407(11)
N9 0.0497(8) 0.0596(10) 0.0638(10) -0.0062(8) 0.0006(7) -0.0171(7)
N34 0.0440(8) 0.0617(10) 0.0826(12) -0.0230(9) 0.0116(7) -0.0126(7)
N35 0.1001(18) 0.0669(14) 0.219(4) -0.0411(18) 0.006(2) -0.0204(13)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.2562(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 . N12 4_556 2.2307(14) yes
Mn1 . N1 . 2.2960(14) yes
Mn1 . N3 . 2.4664(15) yes
Mn1 . N2 . 2.1916(15) yes
Mn1 . N12 . 2.2088(14) yes
Mn1 . N9 . 2.1310(16) yes
N1 . C3 . 1.339(2) yes
N1 . C7 . 1.342(2) yes
C3 . C4 . 1.378(3) yes
C3 . H31 . 0.972 no
C4 . C5 . 1.362(3) yes
C4 . H41 . 0.974 no
C5 . C6 . 1.371(3) yes
C5 . H51 . 0.969 no
C6 . C7 . 1.388(2) yes
C6 . H61 . 0.977 no
C7 . C8 . 1.496(2) yes
C8 . N3 . 1.471(2) yes
C8 . H82 . 0.994 no
C8 . H81 . 0.989 no
N3 . C10 . 1.476(2) yes
N3 . C13 . 1.4751(19) yes
C10 . C11 . 1.480(3) yes
C10 . H102 . 0.997 no
C10 . H101 . 1.013 no
C11 . C12 . 1.168(3) yes
C12 . H121 . 0.980 no
C13 . C14 . 1.495(2) yes
C13 . H131 . 0.991 no
C13 . H132 . 0.998 no
C14 . N2 . 1.317(2) yes
C14 . N18 . 1.348(2) yes
N2 . C16 . 1.372(2) yes
C16 . C17 . 1.342(3) yes
C16 . H161 . 0.986 no
C17 . N18 . 1.382(3) yes
C17 . H171 . 0.965 no
N18 . C19 . 1.455(3) yes
C19 . H192 . 0.960 no
C19 . H193 . 0.997 no
C19 . H191 . 0.979 no
N12 . N31 . 1.1917(19) yes
N31 . N32 . 1.141(2) yes
N9 . N34 . 1.161(2) yes
N34 . N35 . 1.140(3) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N12 4_556 Mn1 . N1 . 161.98(5) yes
N12 4_556 Mn1 . N3 . 101.55(5) yes
N1 . Mn1 . N3 . 69.79(4) yes
N12 4_556 Mn1 . N2 . 90.08(5) yes
N1 . Mn1 . N2 . 101.64(6) yes
N3 . Mn1 . N2 . 72.19(5) yes
N12 4_556 Mn1 . N12 . 76.53(5) yes
N1 . Mn1 . N12 . 87.71(5) yes
N3 . Mn1 . N12 . 91.56(5) yes
N2 . Mn1 . N12 . 156.63(5) yes
N12 4_556 Mn1 . N9 . 101.66(7) yes
N1 . Mn1 . N9 . 90.28(6) yes
N3 . Mn1 . N9 . 154.83(6) yes
N2 . Mn1 . N9 . 98.16(7) yes
N12 . Mn1 . N9 . 103.22(7) yes
Mn1 . N1 . C3 . 123.37(12) yes
Mn1 . N1 . C7 . 118.05(10) yes
C3 . N1 . C7 . 118.35(15) yes
N1 . C3 . C4 . 122.29(18) yes
N1 . C3 . H31 . 117.0 no
C4 . C3 . H31 . 120.7 no
C3 . C4 . C5 . 119.15(18) yes
C3 . C4 . H41 . 119.4 no
C5 . C4 . H41 . 121.4 no
C4 . C5 . C6 . 119.55(18) yes
C4 . C5 . H51 . 121.6 no
C6 . C5 . H51 . 118.8 no
C5 . C6 . C7 . 118.8(2) yes
C5 . C6 . H61 . 118.9 no
C7 . C6 . H61 . 122.3 no
C6 . C7 . N1 . 121.79(17) yes
C6 . C7 . C8 . 120.95(16) yes
N1 . C7 . C8 . 117.26(13) yes
C7 . C8 . N3 . 110.88(12) yes
C7 . C8 . H82 . 109.2 no
N3 . C8 . H82 . 108.0 no
C7 . C8 . H81 . 109.6 no
N3 . C8 . H81 . 110.5 no
H82 . C8 . H81 . 108.5 no
C8 . N3 . Mn1 . 105.14(9) yes
C8 . N3 . C10 . 111.54(13) yes
Mn1 . N3 . C10 . 110.23(9) yes
C8 . N3 . C13 . 111.56(12) yes
Mn1 . N3 . C13 . 107.48(9) yes
C10 . N3 . C13 . 110.67(12) yes
N3 . C10 . C11 . 112.97(15) yes
N3 . C10 . H102 . 108.0 no
C11 . C10 . H102 . 108.5 no
N3 . C10 . H101 . 108.3 no
C11 . C10 . H101 . 109.5 no
H102 . C10 . H101 . 109.5 no
C10 . C11 . C12 . 177.1(2) yes
C11 . C12 . H121 . 179.3 no
N3 . C13 . C14 . 109.29(12) yes
N3 . C13 . H131 . 110.7 no
C14 . C13 . H131 . 111.3 no
N3 . C13 . H132 . 108.6 no
C14 . C13 . H132 . 110.1 no
H131 . C13 . H132 . 106.8 no
C13 . C14 . N2 . 122.24(13) yes
C13 . C14 . N18 . 127.17(14) yes
N2 . C14 . N18 . 110.59(14) yes
Mn1 . N2 . C14 . 118.59(11) yes
Mn1 . N2 . C16 . 135.27(12) yes
C14 . N2 . C16 . 106.13(15) yes
N2 . C16 . C17 . 110.12(17) yes
N2 . C16 . H161 . 123.9 no
C17 . C16 . H161 . 126.0 no
C16 . C17 . N18 . 105.84(16) yes
C16 . C17 . H171 . 129.1 no
N18 . C17 . H171 . 125.0 no
C17 . N18 . C14 . 107.30(15) yes
C17 . N18 . C19 . 125.08(17) yes
C14 . N18 . C19 . 127.59(17) yes
N18 . C19 . H192 . 108.5 no
N18 . C19 . H193 . 108.1 no
H192 . C19 . H193 . 110.6 no
N18 . C19 . H191 . 109.4 no
H192 . C19 . H191 . 111.1 no
H193 . C19 . H191 . 109.1 no
Mn1 . N12 . Mn1 4_556 103.47(6) yes
Mn1 . N12 . N31 . 125.70(12) yes
Mn1 4_556 N12 . N31 . 129.60(12) yes
N12 . N31 . N32 . 179.21(19) yes
Mn1 . N9 . N34 . 128.95(15) yes
N9 . N34 . N35 . 178.3(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C3 . H31 . N9 . 123.10 0.972 2.571 3.207(3) yes
C10 . H102 . N9 4_556 154.88 0.997 2.593 3.521(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 18/02/14 at 16:45:56
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  82,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 102,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 193,X'S) H   ( 191,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 18/02/14 at 16:45:56
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.010000 = N(21) TO N(22) 
U(IJ)'S  0.0, 0.010000 = N(24) TO N(25) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 911105'
#######################################################################
#
#                 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_import

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 '[di-mu-azido-diazido-bis(N,N?-bis((pyridin-2-yl)methyl)prop-2-yn-1-amine)]dimanganese(II)'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 Mn2 N18, 2(C H4 O)'
_chemical_formula_sum            'C32 H38 Mn2 N18 O2'
_chemical_formula_weight         816.68

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'
Mn Mn 0.3368 0.7283 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0552(2)
_cell_length_b                   10.1744(2)
_cell_length_c                   11.1141(2)
_cell_angle_alpha                85.5500(10)
_cell_angle_beta                 81.6560(10)
_cell_angle_gamma                69.6870(10)
_cell_volume                     949.70(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      25.7

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             422
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'

_exptl_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.

;

_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  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8630
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4352
_reflns_number_gt                3467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_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)+(0.0663P)²+0.0000P] 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         4352
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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
N3 N 0.26269(18) 0.46867(16) 0.26465(14) 0.0203(3) Uani 1 1 d . . .
C7 C 0.1707(2) 0.4854(2) 0.16158(17) 0.0244(4) Uani 1 1 d . . .
H8A H 0.2295 0.5088 0.0880 0.029 Uiso 1 1 calc R . .
H8B H 0.0710 0.5621 0.1768 0.029 Uiso 1 1 calc R . .
C6 C 0.4282(2) 0.3760(2) 0.23292(18) 0.0245(4) Uani 1 1 d . . .
H6A H 0.4905 0.4310 0.1923 0.029 Uiso 1 1 calc R . .
H6B H 0.4309 0.3064 0.1770 0.029 Uiso 1 1 calc R . .
O1 O 0.63653(19) 0.06368(17) 0.12952(15) 0.0356(4) Uani 1 1 d . . .
C16 C 0.5179(3) 0.0019(3) 0.1666(3) 0.0441(6) Uani 1 1 d . . .
Mn1 Mn 0.13940(3) 0.35432(3) 0.42219(2) 0.01940(11) Uani 1 1 d . . .
N7 N 0.11130(19) 0.13501(17) 0.61856(15) 0.0234(4) Uani 1 1 d . . .
C2 C 0.6232(2) 0.1555(2) 0.54380(19) 0.0281(5) Uani 1 1 d . . .
H2 H 0.6622 0.1050 0.6126 0.034 Uiso 1 1 calc R . .
N6 N 0.0970(2) 0.17511(18) 0.51610(15) 0.0260(4) Uani 1 1 d . . .
N9 N 0.10230(19) 0.48345(18) 0.58377(14) 0.0243(4) Uani 1 1 d . . .
C10 C 0.0824(3) 0.2020(2) 0.01565(19) 0.0315(5) Uani 1 1 d . . .
H11 H 0.0693 0.1784 -0.0603 0.038 Uiso 1 1 calc R . .
N10 N 0.18322(19) 0.46188(17) 0.66549(15) 0.0240(4) Uani 1 1 d . . .
N1 N 0.40267(18) 0.26723(17) 0.43301(14) 0.0231(4) Uani 1 1 d . . .
C8 C 0.1377(2) 0.3537(2) 0.14317(17) 0.0224(4) Uani 1 1 d . . .
N2 N 0.11693(18) 0.27534(17) 0.24310(14) 0.0217(4) Uani 1 1 d . . .
N11 N 0.2589(2) 0.4418(2) 0.74428(17) 0.0393(5) Uani 1 1 d . . .
C1 C 0.4648(2) 0.1939(2) 0.53093(18) 0.0270(4) Uani 1 1 d . . .
H1 H 0.3978 0.1682 0.5923 0.032 Uiso 1 1 calc R . .
C14 C 0.2999(3) 0.6942(2) 0.2002(2) 0.0304(5) Uani 1 1 d . . .
C5 C 0.5007(2) 0.3031(2) 0.34447(17) 0.0224(4) Uani 1 1 d . . .
C12 C 0.0796(2) 0.1608(2) 0.22932(18) 0.0253(4) Uani 1 1 d . . .
H13 H 0.0669 0.1053 0.2978 0.030 Uiso 1 1 calc R . .
C9 C 0.1253(3) 0.3172(2) 0.02817(18) 0.0287(5) Uani 1 1 d . . .
H10 H 0.1459 0.3702 -0.0400 0.034 Uiso 1 1 calc R . .
N8 N 0.1239(2) 0.0947(2) 0.71847(17) 0.0386(5) Uani 1 1 d . . .
C11 C 0.0594(2) 0.1220(2) 0.11895(19) 0.0299(5) Uani 1 1 d . . .
H12 H 0.0308 0.0435 0.1135 0.036 Uiso 1 1 calc R . .
C4 C 0.6612(2) 0.2678(2) 0.35221(19) 0.0275(5) Uani 1 1 d . . .
H4 H 0.7267 0.2941 0.2900 0.033 Uiso 1 1 calc R . .
C3 C 0.7230(2) 0.1930(2) 0.45327(19) 0.0288(5) Uani 1 1 d . . .
H3 H 0.8305 0.1684 0.4600 0.035 Uiso 1 1 calc R . .
C13 C 0.2579(3) 0.6066(2) 0.30263(18) 0.0265(4) Uani 1 1 d . . .
H13A H 0.1520 0.6566 0.3416 0.032 Uiso 1 1 calc R . .
H13B H 0.3309 0.5917 0.3622 0.032 Uiso 1 1 calc R . .
C15 C 0.3279(3) 0.7598(2) 0.1131(2) 0.0362(5) Uani 1 1 d . . .
H15 H 0.3499 0.8116 0.0445 0.043 Uiso 1 1 calc R . .
H14A H 0.450(3) 0.039(3) 0.250(2) 0.039(7) Uiso 1 1 d . . .
H14B H 0.444(3) 0.032(3) 0.104(3) 0.058(8) Uiso 1 1 d . . .
H14C H 0.556(3) -0.098(3) 0.167(2) 0.041(7) Uiso 1 1 d . . .
H1O H 0.702(3) 0.026(3) 0.183(2) 0.051(8) Uiso 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
N3 0.0210(8) 0.0208(8) 0.0182(8) 0.0006(6) -0.0025(6) -0.0063(7)
C7 0.0264(10) 0.0271(11) 0.0186(10) 0.0047(8) -0.0052(8) -0.0080(9)
C6 0.0228(10) 0.0250(11) 0.0232(10) 0.0021(8) 0.0006(8) -0.0071(8)
O1 0.0361(9) 0.0345(9) 0.0329(9) 0.0058(7) -0.0038(7) -0.0096(7)
C16 0.0426(15) 0.0458(17) 0.0450(16) 0.0065(13) -0.0061(13) -0.0179(13)
Mn1 0.01825(17) 0.02146(18) 0.01725(17) 0.00064(12) -0.00216(11) -0.00550(12)
N7 0.0215(9) 0.0221(9) 0.0258(9) 0.0007(7) -0.0013(7) -0.0072(7)
C2 0.0262(11) 0.0291(11) 0.0268(11) 0.0022(9) -0.0093(9) -0.0051(9)
N6 0.0293(9) 0.0263(9) 0.0230(9) 0.0046(7) -0.0055(7) -0.0105(7)
N9 0.0207(8) 0.0280(9) 0.0206(8) -0.0036(7) -0.0042(7) -0.0024(7)
C10 0.0348(12) 0.0352(12) 0.0235(11) -0.0079(9) -0.0072(9) -0.0079(10)
N10 0.0223(9) 0.0245(9) 0.0239(9) 0.0005(7) -0.0046(7) -0.0060(7)
N1 0.0206(8) 0.0246(9) 0.0224(8) 0.0015(7) -0.0029(7) -0.0060(7)
C8 0.0211(9) 0.0245(10) 0.0191(9) -0.0001(8) -0.0014(8) -0.0051(8)
N2 0.0206(8) 0.0236(9) 0.0197(8) -0.0002(7) -0.0015(6) -0.0067(7)
N11 0.0390(11) 0.0486(13) 0.0319(11) 0.0031(9) -0.0166(9) -0.0129(10)
C1 0.0221(10) 0.0304(11) 0.0257(11) 0.0048(9) -0.0029(8) -0.0067(9)
C14 0.0327(12) 0.0255(11) 0.0338(12) 0.0008(9) -0.0048(9) -0.0108(9)
C5 0.0222(10) 0.0207(10) 0.0235(10) -0.0026(8) -0.0003(8) -0.0070(8)
C12 0.0236(10) 0.0253(11) 0.0255(10) 0.0001(8) -0.0004(8) -0.0076(8)
C9 0.0342(12) 0.0294(11) 0.0202(10) 0.0021(9) -0.0057(9) -0.0076(9)
N8 0.0447(12) 0.0438(12) 0.0237(10) 0.0071(9) -0.0052(8) -0.0118(10)
C11 0.0303(11) 0.0277(11) 0.0332(12) -0.0075(9) -0.0039(9) -0.0104(9)
C4 0.0225(10) 0.0306(11) 0.0302(11) -0.0024(9) -0.0002(9) -0.0111(9)
C3 0.0185(10) 0.0336(12) 0.0339(12) -0.0065(9) -0.0057(9) -0.0060(9)
C13 0.0306(11) 0.0238(11) 0.0242(10) -0.0002(8) -0.0019(8) -0.0088(9)
C15 0.0429(14) 0.0315(12) 0.0379(13) 0.0051(10) -0.0058(10) -0.0181(11)

_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
N3 C6 1.476(2) . ?
N3 C7 1.478(2) . ?
N3 C13 1.481(3) . ?
N3 Mn1 2.3842(16) . ?
C7 C8 1.504(3) . ?
C7 H8A 0.9700 . ?
C7 H8B 0.9700 . ?
C6 C5 1.508(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O1 C16 1.420(3) . ?
O1 H1O 0.87(3) . ?
C16 H14A 1.05(3) . ?
C16 H14B 0.99(3) . ?
C16 H14C 0.95(3) . ?
Mn1 N6 2.1532(17) . ?
Mn1 N9 2.2245(16) . ?
Mn1 N9 2.2441(16) 2_566 ?
Mn1 N1 2.2545(16) . ?
Mn1 N2 2.2646(16) . ?
N7 N8 1.161(2) . ?
N7 N6 1.189(2) . ?
C2 C3 1.375(3) . ?
C2 C1 1.375(3) . ?
C2 H2 0.9300 . ?
N9 N10 1.209(2) . ?
N9 Mn1 2.2441(16) 2_566 ?
C10 C9 1.379(3) . ?
C10 C11 1.388(3) . ?
C10 H11 0.9300 . ?
N10 N11 1.152(2) . ?
N1 C5 1.344(2) . ?
N1 C1 1.348(2) . ?
C8 N2 1.346(2) . ?
C8 C9 1.388(3) . ?
N2 C12 1.346(3) . ?
C1 H1 0.9300 . ?
C14 C15 1.180(3) . ?
C14 C13 1.479(3) . ?
C5 C4 1.384(3) . ?
C12 C11 1.372(3) . ?
C12 H13 0.9300 . ?
C9 H10 0.9300 . ?
C11 H12 0.9300 . ?
C4 C3 1.381(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15 0.9300 . ?

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
C6 N3 C7 110.72(15) . . ?
C6 N3 C13 110.55(15) . . ?
C7 N3 C13 110.90(15) . . ?
C6 N3 Mn1 108.10(11) . . ?
C7 N3 Mn1 104.84(11) . . ?
C13 N3 Mn1 111.57(11) . . ?
N3 C7 C8 111.54(15) . . ?
N3 C7 H8A 109.3 . . ?
C8 C7 H8A 109.3 . . ?
N3 C7 H8B 109.3 . . ?
C8 C7 H8B 109.3 . . ?
H8A C7 H8B 108.0 . . ?
N3 C6 C5 111.38(16) . . ?
N3 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N3 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C16 O1 H1O 101.1(18) . . ?
O1 C16 H14A 112.8(13) . . ?
O1 C16 H14B 105.8(16) . . ?
H14A C16 H14B 107(2) . . ?
O1 C16 H14C 114.4(15) . . ?
H14A C16 H14C 111(2) . . ?
H14B C16 H14C 106(2) . . ?
N6 Mn1 N9 97.84(6) . . ?
N6 Mn1 N9 105.08(6) . 2_566 ?
N9 Mn1 N9 75.50(6) . 2_566 ?
N6 Mn1 N1 93.54(6) . . ?
N9 Mn1 N1 90.62(6) . . ?
N9 Mn1 N1 157.98(6) 2_566 . ?
N6 Mn1 N2 90.02(6) . . ?
N9 Mn1 N2 163.57(6) . . ?
N9 Mn1 N2 88.55(6) 2_566 . ?
N1 Mn1 N2 103.33(6) . . ?
N6 Mn1 N3 154.43(6) . . ?
N9 Mn1 N3 103.72(6) . . ?
N9 Mn1 N3 93.60(6) 2_566 . ?
N1 Mn1 N3 72.86(5) . . ?
N2 Mn1 N3 72.89(6) . . ?
N8 N7 N6 179.0(2) . . ?
C3 C2 C1 118.91(19) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
N7 N6 Mn1 129.17(14) . . ?
N10 N9 Mn1 128.26(13) . . ?
N10 N9 Mn1 126.62(13) . 2_566 ?
Mn1 N9 Mn1 104.50(6) . 2_566 ?
C9 C10 C11 118.50(19) . . ?
C9 C10 H11 120.7 . . ?
C11 C10 H11 120.7 . . ?
N11 N10 N9 179.3(2) . . ?
C5 N1 C1 118.14(16) . . ?
C5 N1 Mn1 118.59(12) . . ?
C1 N1 Mn1 122.83(13) . . ?
N2 C8 C9 121.75(19) . . ?
N2 C8 C7 117.09(16) . . ?
C9 C8 C7 121.14(18) . . ?
C8 N2 C12 118.03(17) . . ?
C8 N2 Mn1 116.23(13) . . ?
C12 N2 Mn1 125.69(13) . . ?
N1 C1 C2 122.77(19) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C15 C14 C13 175.0(2) . . ?
N1 C5 C4 121.82(18) . . ?
N1 C5 C6 116.24(16) . . ?
C4 C5 C6 121.83(18) . . ?
N2 C12 C11 123.11(19) . . ?
N2 C12 H13 118.4 . . ?
C11 C12 H13 118.4 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H10 120.2 . . ?
C8 C9 H10 120.2 . . ?
C12 C11 C10 118.9(2) . . ?
C12 C11 H12 120.6 . . ?
C10 C11 H12 120.6 . . ?
C3 C4 C5 119.36(19) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C2 C3 C4 119.00(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C14 C13 N3 113.16(17) . . ?
C14 C13 H13A 108.9 . . ?
N3 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
N3 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
C14 C15 H15 180.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.154
_database_code_depnum_ccdc_archive 'CCDC 911106'
