# 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_nitril







_audit_creation_method           SHELXL-97


_chemical_name_systematic        


;                                                                               


 ?                                                                             



;



_chemical_name_common            ?


_chemical_melting_point          ?


_chemical_formula_moiety         ?


_chemical_formula_sum            

'C22 H20 N2 O7'



_chemical_formula_weight         424.40






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'






_symmetry_cell_setting           Monoclinic


_symmetry_space_group_name_H-M   P2(1)/c






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                   7.7428(14)


_cell_length_b                   12.863(2)


_cell_length_c                   20.288(4)


_cell_angle_alpha                90.00


_cell_angle_beta                 92.172(3)


_cell_angle_gamma                90.00


_cell_volume                     2019.1(6)


_cell_formula_units_Z            4


_cell_measurement_temperature    150(2)


_cell_measurement_reflns_used    4520


_cell_measurement_theta_min      2.56


_cell_measurement_theta_max      26.74





_exptl_crystal_description       prizm


_exptl_crystal_colour            colourless


_exptl_crystal_size_max          0.14


_exptl_crystal_size_mid          0.12


_exptl_crystal_size_min          0.10


_exptl_crystal_density_meas      ?


_exptl_crystal_density_diffrn    1.396


_exptl_crystal_density_method    'not measured'


_exptl_crystal_F_000             888


_exptl_absorpt_coefficient_mu    0.105


_exptl_absorpt_correction_type   multi-scan


_exptl_absorpt_correction_T_min  0.9854


_exptl_absorpt_correction_T_max  0.9895


_exptl_absorpt_process_details   sadabs






_exptl_special_details           


;                                                                              



 ?                                                              
               


;







_diffrn_ambient_temperature      150(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  'CCD area detector'


_diffrn_measurement_method       'phi and omega scans'


_diffrn_detector_area_resol_mean ?


_diffrn_standards_number         ?


_diffrn_standards_interval_count ?


_diffrn_standards_interval_time  ?


_diffrn_standards_decay_%        ?


_diffrn_reflns_number            21428


_diffrn_reflns_av_R_equivalents  0.0307


_diffrn_reflns_av_sigmaI/netI    0.0283


_diffrn_reflns_limit_h_min       -10


_diffrn_reflns_limit_h_max       10


_diffrn_reflns_limit_k_min       -17


_diffrn_reflns_limit_k_max       17


_diffrn_reflns_limit_l_min       -27


_diffrn_reflns_limit_l_max       27


_diffrn_reflns_theta_min         2.56


_diffrn_reflns_theta_max         29.00


_reflns_number_total             5285


_reflns_number_gt                3184


_reflns_threshold_expression     >2sigma(I)






_computing_data_collection       'Bruker SMART'


_computing_cell_refinement       'Bruker SMART'


_computing_data_reduction        'Bruker SAINT'


_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'


_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'


_computing_molecular_graphics    'Bruker SHELXTL'


_computing_publication_material  'Bruker SHELXTL'






_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)+(0.0638P)²+0.2279P]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         5285


_refine_ls_number_parameters     289


_refine_ls_number_restraints     0


_refine_ls_R_factor_all          0.0884


_refine_ls_R_factor_gt           0.0475


_refine_ls_wR_factor_ref         0.1359


_refine_ls_wR_factor_gt          0.1127


_refine_ls_goodness_of_fit_ref   1.011


_refine_ls_restrained_S_all      1.011


_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









































































































O1 O 0.3201(2) 0.36729(8) 0.56204(5) 0.0669(4) Uani 1 1 d . . .
O2 O 0.20468(19) 0.48462(8) 0.44960(5) 0.0639(4) Uani 1 1 d . . .
O3 O 0.23594(16) 0.79070(8) 0.58430(5) 0.0525(3) Uani 1 1 d . . .
O4 O 0.02541(15) 0.96831(8) 0.60376(6) 0.0515(3) Uani 1 1 d . . .
O5 O 0.1551(8) 1.0185(4) 0.7463(3) 0.071(2) Uani 0.60 1 d P A 1
O5A O 0.1438(14) 1.0251(7) 0.7445(4) 0.100(4) Uani 0.40 1 d P A 2
O6 O 0.2004(2) 0.75692(9) 0.80620(6) 0.0701(4) Uani 1 1 d . . .
O7 O 0.33516(16) 0.68687(8) 0.68538(5) 0.0548(3) Uani 1 1 d . . .
N1 N 0.4131(2) -0.01822(11) 0.41910(8) 0.0581(4) Uani 1 1 d . . .
N2 N 0.2667(3) 0.14536(13) 0.26292(8) 0.0773(5) Uani 1 1 d . . .
C1 C 0.3046(2) 0.32477(11) 0.50040(7) 0.0465(4) Uani 1 1 d . . .
C2 C 0.3474(2) 0.22160(11) 0.49380(8) 0.0458(4) Uani 1 1 d . . .
H2A H 0.3867 0.1826 0.5312 0.055 Uiso 1 1 calc R . .
C3 C 0.33282(18) 0.17470(11) 0.43212(7) 0.0408(3) Uani 1 1 d . . .
C4 C 0.3769(2) 0.06714(12) 0.42480(8) 0.0447(4) Uani 1 1 d . . .
C5 C 0.2763(2) 0.23232(12) 0.37719(7) 0.0440(4) Uani 1 1 d . . .
C6 C 0.2676(2) 0.18397(13) 0.31310(9) 0.0543(4) Uani 1 1 d . . .
C7 C 0.2335(2) 0.33629(12) 0.38398(8) 0.0498(4) Uani 1 1 d . . .
H7A H 0.1945 0.3757 0.3467 0.060 Uiso 1 1 calc R . .
C8 C 0.2479(2) 0.38182(11) 0.44523(8) 0.0467(4) Uani 1 1 d . . .
C9 C 0.2416(2) 0.53085(11) 0.51056(7) 0.0467(4) Uani 1 1 d . . .
C10 C 0.2194(2) 0.63749(11) 0.51445(8) 0.0460(4) Uani 1 1 d . . .
H10A H 0.1827 0.6761 0.4766 0.055 Uiso 1 1 calc R . .
C11 C 0.2513(2) 0.68687(11) 0.57405(7) 0.0421(3) Uani 1 1 d . . .
C12 C 0.1642(2) 0.85241(11) 0.53255(8) 0.0474(4) Uani 1 1 d . . .
H12A H 0.0467 0.8276 0.5196 0.057 Uiso 1 1 calc R . .
H12B H 0.2370 0.8487 0.4935 0.057 Uiso 1 1 calc R . .
C13 C 0.1571(2) 0.96113(12) 0.55756(9) 0.0494(4) Uani 1 1 d . . .
H13A H 0.2698 0.9804 0.5788 0.059 Uiso 1 1 calc R . .
H13B H 0.1326 1.0096 0.5205 0.059 Uiso 1 1 calc R . .
C14 C 0.0237(3) 1.06541(14) 0.63714(10) 0.0618(5) Uani 1 1 d . A .
H14A H -0.0889 1.0730 0.6582 0.074 Uiso 1 1 calc R . .
H14B H 0.0318 1.1216 0.6040 0.074 Uiso 1 1 calc R . .
C15 C 0.1621(3) 1.08029(15) 0.68783(11) 0.0760(6) Uani 1 1 d . . .
H15A H 0.2739 1.0663 0.6674 0.091 Uiso 1 1 calc R A 1
H15B H 0.1623 1.1544 0.7011 0.091 Uiso 1 1 calc R A 1
C16 C 0.1944(3) 0.91303(13) 0.73979(9) 0.0638(5) Uani 1 1 d . . .
H16A H 0.3108 0.9043 0.7220 0.077 Uiso 1 1 calc R A 1
H16B H 0.1089 0.8786 0.7095 0.077 Uiso 1 1 calc R A 1
C17 C 0.1885(3) 0.86697(14) 0.80755(9) 0.0702(6) Uani 1 1 d . A .
H17A H 0.2852 0.8953 0.8354 0.084 Uiso 1 1 calc R . .
H17B H 0.0790 0.8874 0.8277 0.084 Uiso 1 1 calc R . .
C18 C 0.3678(3) 0.71608(14) 0.79900(9) 0.0636(5) Uani 1 1 d . . .
H18A H 0.4102 0.6855 0.8414 0.076 Uiso 1 1 calc R . .
H18B H 0.4475 0.7728 0.7874 0.076 Uiso 1 1 calc R . .
C19 C 0.3665(3) 0.63435(14) 0.74627(8) 0.0605(5) Uani 1 1 d . . .
H19A H 0.4791 0.5978 0.7464 0.073 Uiso 1 1 calc R . .
H19B H 0.2745 0.5827 0.7536 0.073 Uiso 1 1 calc R . .
C20 C 0.3057(2) 0.62921(11) 0.62987(7) 0.0436(3) Uani 1 1 d . . .
C21 C 0.3269(2) 0.52278(12) 0.62497(8) 0.0493(4) Uani 1 1 d . . .
H21A H 0.3626 0.4831 0.6626 0.059 Uiso 1 1 calc R . .
C22 C 0.2956(2) 0.47489(11) 0.56476(8) 0.0486(4) Uani 1 1 d . . .












_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






































































































O1 C1 1.3661(18) . ?
O1 C22 1.3982(18) . ?
O2 C8 1.3678(18) . ?
O2 C9 1.3921(18) . ?
O3 C11 1.3576(17) . ?
O3 C12 1.4130(18) . ?
O4 C13 1.414(2) . ?
O4 C14 1.421(2) . ?
O5 C16 1.398(6) . ?
O5 C15 1.431(6) . ?
O5A C15 1.362(9) . ?
O5A C16 1.498(10) . ?
O6 C18 1.411(3) . ?
O6 C17 1.419(2) . ?
O7 C20 1.3603(18) . ?
O7 C19 1.4209(19) . ?
N1 C4 1.1402(19) . ?
N2 C6 1.133(2) . ?
C1 C2 1.375(2) . ?
C1 C8 1.395(2) . ?
C2 C3 1.390(2) . ?
C3 C5 1.395(2) . ?
C3 C4 1.434(2) . ?
C5 C7 1.386(2) . ?
C5 C6 1.441(2) . ?
C7 C8 1.374(2) . ?
C9 C22 1.367(2) . ?
C9 C10 1.385(2) . ?
C10 C11 1.380(2) . ?
C11 C20 1.405(2) . ?
C12 C13 1.489(2) . ?
C14 C15 1.470(3) . ?
C16 C17 1.499(3) . ?
C18 C19 1.499(2) . ?
C20 C21 1.383(2) . ?
C21 C22 1.381(2) . ?







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

















































































































































C1 O1 C22 115.16(12) . . ?
C8 O2 C9 115.35(12) . . ?
C11 O3 C12 118.22(12) . . ?
C13 O4 C14 113.16(13) . . ?
C16 O5 C15 116.4(4) . . ?
C15 O5A C16 114.3(6) . . ?
C18 O6 C17 115.73(16) . . ?
C20 O7 C19 118.58(12) . . ?
O1 C1 C2 117.54(13) . . ?
O1 C1 C8 122.53(13) . . ?
C2 C1 C8 119.93(14) . . ?
C1 C2 C3 119.65(14) . . ?
C2 C3 C5 120.06(13) . . ?
C2 C3 C4 120.03(14) . . ?
C5 C3 C4 119.91(13) . . ?
N1 C4 C3 179.54(19) . . ?
C7 C5 C3 120.16(13) . . ?
C7 C5 C6 120.20(14) . . ?
C3 C5 C6 119.62(14) . . ?
N2 C6 C5 177.6(2) . . ?
C8 C7 C5 119.29(14) . . ?
O2 C8 C7 117.31(13) . . ?
O2 C8 C1 121.79(13) . . ?
C7 C8 C1 120.90(14) . . ?
C22 C9 C10 120.71(14) . . ?
C22 C9 O2 122.42(13) . . ?
C10 C9 O2 116.87(13) . . ?
C11 C10 C9 119.17(14) . . ?
O3 C11 C10 124.99(13) . . ?
O3 C11 C20 114.90(13) . . ?
C10 C11 C20 120.10(13) . . ?
O3 C12 C13 107.02(13) . . ?
O4 C13 C12 108.89(13) . . ?
O4 C14 C15 115.35(15) . . ?
O5A C15 O5 4.4(7) . . ?
O5A C15 C14 115.2(5) . . ?
O5 C15 C14 117.3(3) . . ?
O5 C16 O5A 3.1(6) . . ?
O5 C16 C17 106.4(3) . . ?
O5A C16 C17 107.8(4) . . ?
O6 C17 C16 111.85(14) . . ?
O6 C18 C19 110.71(16) . . ?
O7 C19 C18 106.45(14) . . ?
O7 C20 C21 125.64(14) . . ?
O7 C20 C11 114.53(13) . . ?
C21 C20 C11 119.83(14) . . ?
C22 C21 C20 119.19(14) . . ?
C9 C22 C21 120.99(14) . . ?
C9 C22 O1 121.84(14) . . ?
C21 C22 O1 117.17(13) . . ?







_diffrn_measured_fraction_theta_max 0.981


_diffrn_reflns_theta_full        29.00


_diffrn_measured_fraction_theta_full 0.981


_refine_diff_density_max         0.312


_refine_diff_density_min         -0.182


_refine_diff_density_rms         0.036








_database_code_depnum_ccdc_archive 'CCDC 1014940'
