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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_ARC_CCOM_sb

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H27 Cl N4 O9 V'
_chemical_formula_sum            'C26 H27 Cl N4 O9 V'
_chemical_formula_weight         625.91

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 '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'

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

_cell_length_a                   9.4205(5)
_cell_length_b                   11.9369(11)
_cell_length_c                   13.5029(11)
_cell_angle_alpha                68.758(8)
_cell_angle_beta                 77.535(5)
_cell_angle_gamma                84.902(6)
_cell_volume                     1381.80(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             646
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7471
_exptl_absorpt_correction_T_max  0.9038
_exptl_absorpt_process_details   SADABS

_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 Smart CCD Area Detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19241
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0561
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         27.47
_reflns_number_total             6319
_reflns_number_gt                4427
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 > 2σ(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)+(0.0503P)²+0.8166P] 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         6319
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
V1 V 0.42269(5) 0.13967(4) 0.78312(4) 0.03689(16) Uani 1 1 d . . .
Cl1 Cl 0.85479(9) 0.46086(8) 0.77288(6) 0.0537(2) Uani 1 1 d . . .
O1 O 0.3051(2) 0.05166(19) 0.87593(16) 0.0524(6) Uani 1 1 d . . .
O2 O 0.3838(2) 0.28311(19) 0.82313(17) 0.0479(5) Uani 1 1 d . . .
O3 O 0.5342(2) 0.02707(18) 0.71675(16) 0.0453(5) Uani 1 1 d . . .
O4 O 0.7176(4) 0.2953(3) 1.1583(2) 0.0838(10) Uani 1 1 d . . .
O5 O 0.8768(4) 0.3364(3) 0.7950(3) 0.1006(10) Uani 1 1 d . . .
O6 O 0.8710(4) 0.4818(3) 0.8673(3) 0.1036(11) Uani 1 1 d . . .
O7 O 0.9541(4) 0.5261(4) 0.6834(3) 0.1409(17) Uani 1 1 d . . .
O8 O 0.7085(3) 0.4940(3) 0.7577(2) 0.0792(8) Uani 1 1 d . . .
O9 O 0.6127(4) 0.1179(3) 0.3459(2) 0.1023(12) Uani 1 1 d . . .
H9A H 0.5366 0.0846 0.3536 0.154 Uiso 1 1 calc R . .
N1 N 0.5437(2) 0.2788(2) 0.62375(18) 0.0369(5) Uani 1 1 d . . .
N2 N 0.2821(3) 0.1913(2) 0.66909(19) 0.0388(6) Uani 1 1 d . . .
N3 N 0.6040(3) 0.1099(2) 0.85571(18) 0.0378(6) Uani 1 1 d . . .
N4 N 0.3498(4) 0.3939(3) 1.0360(2) 0.0558(8) Uani 1 1 d . . .
C1 C 0.6741(3) 0.3250(3) 0.6088(3) 0.0450(7) Uani 1 1 d . . .
H1 H 0.7203 0.3032 0.6675 0.054 Uiso 1 1 calc R . .
C2 C 0.7433(4) 0.4036(3) 0.5103(3) 0.0529(8) Uani 1 1 d . . .
H2 H 0.8337 0.4346 0.5028 0.064 Uiso 1 1 calc R . .
C3 C 0.6756(4) 0.4346(3) 0.4238(3) 0.0563(9) Uani 1 1 d . . .
H3 H 0.7205 0.4865 0.3562 0.068 Uiso 1 1 calc R . .
C4 C 0.5405(4) 0.3887(3) 0.4374(2) 0.0498(8) Uani 1 1 d . . .
H4 H 0.4933 0.4091 0.3793 0.060 Uiso 1 1 calc R . .
C5 C 0.4762(3) 0.3113(2) 0.5393(2) 0.0376(6) Uani 1 1 d . . .
C6 C 0.3282(3) 0.2623(2) 0.5647(2) 0.0382(6) Uani 1 1 d . . .
C7 C 0.2405(4) 0.2884(3) 0.4894(3) 0.0526(8) Uani 1 1 d . . .
H7 H 0.2741 0.3369 0.4178 0.063 Uiso 1 1 calc R . .
C8 C 0.1018(4) 0.2416(3) 0.5217(3) 0.0613(10) Uani 1 1 d . . .
H8 H 0.0415 0.2584 0.4718 0.074 Uiso 1 1 calc R . .
C9 C 0.0543(4) 0.1711(3) 0.6266(3) 0.0599(10) Uani 1 1 d . . .
H9 H -0.0386 0.1390 0.6495 0.072 Uiso 1 1 calc R . .
C10 C 0.1457(3) 0.1484(3) 0.6977(3) 0.0523(8) Uani 1 1 d . . .
H10 H 0.1123 0.1008 0.7696 0.063 Uiso 1 1 calc R . .
C11 C 0.6524(3) -0.0215(3) 0.7566(2) 0.0431(7) Uani 1 1 d . . .
C12 C 0.7329(4) -0.1138(3) 0.7279(3) 0.0548(9) Uani 1 1 d . . .
H12 H 0.7048 -0.1420 0.6793 0.066 Uiso 1 1 calc R . .
C13 C 0.8530(4) -0.1625(3) 0.7716(3) 0.0638(10) Uani 1 1 d . . .
H13 H 0.9055 -0.2237 0.7523 0.077 Uiso 1 1 calc R . .
C14 C 0.8966(4) -0.1217(3) 0.8434(3) 0.0642(10) Uani 1 1 d . . .
H14 H 0.9784 -0.1555 0.8720 0.077 Uiso 1 1 calc R . .
C15 C 0.8199(4) -0.0310(3) 0.8734(3) 0.0540(9) Uani 1 1 d . . .
H15 H 0.8498 -0.0039 0.9221 0.065 Uiso 1 1 calc R . .
C16 C 0.6972(3) 0.0199(3) 0.8302(2) 0.0408(7) Uani 1 1 d . . .
C17 C 0.6298(3) 0.1608(3) 0.9196(2) 0.0419(7) Uani 1 1 d . . .
H17 H 0.7160 0.1400 0.9453 0.050 Uiso 1 1 calc R . .
C18 C 0.5357(3) 0.2472(3) 0.9541(2) 0.0412(7) Uani 1 1 d . . .
C19 C 0.4143(3) 0.2980(3) 0.9074(2) 0.0413(7) Uani 1 1 d . . .
C20 C 0.3165(4) 0.3714(3) 0.9536(3) 0.0469(8) Uani 1 1 d . . .
C21 C 0.1790(4) 0.4195(3) 0.9168(3) 0.0638(10) Uani 1 1 d . . .
H21A H 0.1289 0.4664 0.9586 0.096 Uiso 1 1 calc R . .
H21B H 0.1188 0.3540 0.9265 0.096 Uiso 1 1 calc R . .
H21C H 0.2001 0.4692 0.8415 0.096 Uiso 1 1 calc R . .
C22 C 0.4702(4) 0.3543(3) 1.0771(3) 0.0549(9) Uani 1 1 d . . .
H22 H 0.4875 0.3769 1.1325 0.066 Uiso 1 1 calc R . .
C23 C 0.5667(4) 0.2815(3) 1.0380(2) 0.0471(8) Uani 1 1 d . . .
C24 C 0.7035(4) 0.2403(3) 1.0843(3) 0.0628(10) Uani 1 1 d . . .
H24A H 0.7013 0.1537 1.1207 0.075 Uiso 1 1 calc R . .
H24B H 0.7877 0.2592 1.0254 0.075 Uiso 1 1 calc R . .
C25 C 0.8041(5) 0.1181(4) 0.4352(4) 0.0869(14) Uani 1 1 d . . .
H25A H 0.8358 0.0769 0.5024 0.130 Uiso 1 1 calc R . .
H25B H 0.7894 0.2018 0.4251 0.130 Uiso 1 1 calc R . .
H25C H 0.8767 0.1094 0.3764 0.130 Uiso 1 1 calc R . .
C26 C 0.6692(5) 0.0672(4) 0.4378(4) 0.0793(12) Uani 1 1 d . . .
H26A H 0.6849 -0.0180 0.4508 0.095 Uiso 1 1 calc R . .
H26B H 0.5978 0.0748 0.4986 0.095 Uiso 1 1 calc R . .
H4A H 0.291(4) 0.433(3) 1.063(3) 0.055(12) Uiso 1 1 d . . .
H4B H 0.682(6) 0.245(5) 1.228(4) 0.13(2) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
V1 O1 1.598(2) . ?
V1 O2 1.957(2) . ?
V1 O3 1.982(2) . ?
V1 N3 2.089(2) . ?
V1 N2 2.134(2) . ?
V1 N1 2.319(2) . ?
Cl1 O7 1.379(3) . ?
Cl1 O5 1.411(3) . ?
Cl1 O6 1.426(3) . ?
Cl1 O8 1.437(3) . ?
O2 C19 1.306(3) . ?
O3 C11 1.336(4) . ?
O4 C24 1.412(4) . ?
O4 H4B 0.92(5) . ?
O9 C26 1.369(4) . ?
O9 H9A 0.8200 . ?
N1 C1 1.336(4) . ?
N1 C5 1.344(3) . ?
N2 C10 1.349(4) . ?
N2 C6 1.353(3) . ?
N3 C17 1.292(4) . ?
N3 C16 1.419(4) . ?
N4 C20 1.338(4) . ?
N4 C22 1.343(5) . ?
N4 H4A 0.80(3) . ?
C1 C2 1.381(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.482(4) . ?
C6 C7 1.378(4) . ?
C7 C8 1.384(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.358(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.366(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.405(4) . ?
C11 C16 1.409(4) . ?
C12 C13 1.374(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.399(4) . ?
C15 H15 0.9300 . ?
C17 C18 1.439(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.409(4) . ?
C18 C23 1.427(4) . ?
C19 C20 1.417(4) . ?
C20 C21 1.482(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.358(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.519(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.445(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 99.32(11) . . ?
O1 V1 O3 101.12(11) . . ?
O2 V1 O3 157.83(9) . . ?
O1 V1 N3 102.47(10) . . ?
O2 V1 N3 86.82(9) . . ?
O3 V1 N3 80.48(9) . . ?
O1 V1 N2 92.88(10) . . ?
O2 V1 N2 95.20(9) . . ?
O3 V1 N2 92.28(9) . . ?
N3 V1 N2 164.00(9) . . ?
O1 V1 N1 164.91(10) . . ?
O2 V1 N1 81.43(9) . . ?
O3 V1 N1 81.08(8) . . ?
N3 V1 N1 92.62(8) . . ?
N2 V1 N1 72.07(8) . . ?
O7 Cl1 O5 110.8(3) . . ?
O7 Cl1 O6 111.0(3) . . ?
O5 Cl1 O6 106.4(2) . . ?
O7 Cl1 O8 110.97(19) . . ?
O5 Cl1 O8 109.90(19) . . ?
O6 Cl1 O8 107.64(18) . . ?
C19 O2 V1 126.92(19) . . ?
C11 O3 V1 114.84(19) . . ?
C24 O4 H4B 109(3) . . ?
C26 O9 H9A 109.5 . . ?
C1 N1 C5 118.5(2) . . ?
C1 N1 V1 125.9(2) . . ?
C5 N1 V1 115.57(18) . . ?
C10 N2 C6 117.6(2) . . ?
C10 N2 V1 120.7(2) . . ?
C6 N2 V1 121.62(19) . . ?
C17 N3 C16 122.2(3) . . ?
C17 N3 V1 126.5(2) . . ?
C16 N3 V1 111.24(18) . . ?
C20 N4 C22 125.1(3) . . ?
C20 N4 H4A 116(3) . . ?
C22 N4 H4A 119(3) . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.5(3) . . ?
N1 C5 C6 115.0(2) . . ?
C4 C5 C6 123.5(3) . . ?
N2 C6 C7 121.5(3) . . ?
N2 C6 C5 115.1(2) . . ?
C7 C6 C5 123.4(3) . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 123.4(3) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
O3 C11 C12 121.8(3) . . ?
O3 C11 C16 119.3(3) . . ?
C12 C11 C16 118.9(3) . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 119.9(3) . . ?
C15 C16 N3 126.6(3) . . ?
C11 C16 N3 113.5(3) . . ?
N3 C17 C18 125.2(3) . . ?
N3 C17 H17 117.4 . . ?
C18 C17 H17 117.4 . . ?
C19 C18 C23 119.5(3) . . ?
C19 C18 C17 121.6(3) . . ?
C23 C18 C17 118.9(3) . . ?
O2 C19 C18 124.9(3) . . ?
O2 C19 C20 116.4(3) . . ?
C18 C19 C20 118.8(3) . . ?
N4 C20 C19 117.6(3) . . ?
N4 C20 C21 119.7(3) . . ?
C19 C20 C21 122.7(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 C23 120.2(3) . . ?
N4 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 118.5(3) . . ?
C22 C23 C24 119.1(3) . . ?
C18 C23 C24 122.4(3) . . ?
O4 C24 C23 112.1(3) . . ?
O4 C24 H24A 109.2 . . ?
C23 C24 H24A 109.2 . . ?
O4 C24 H24B 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O9 C26 C25 115.2(4) . . ?
O9 C26 H26A 108.5 . . ?
C25 C26 H26A 108.5 . . ?
O9 C26 H26B 108.5 . . ?
C25 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 974426'
