# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_New_Global_Publ_Block
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222

_audit_update_record             
;
2011-11-22 # Formatted by publCIF
;

_publ_section_related_literature ?

# Added by publCIF - use a unique identifier for each data block

#==============================================================================

# SUBMISSION DETAILS

_publ_contact_author_name        
'Verena Kraehmer' # Name of author for correspondence
_publ_contact_author_address     # Address of author for
correspondence

_publ_contact_author_email       kraehmer@chemie.uni-hamburg.de
_publ_contact_author_fax         '+49 40 42838 2893'
_publ_contact_author_phone       '+49 40 42838 3110'

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this
contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for
publication
elsewhere; that all authors concur with and are aware of the submission;
that
all workers involved in the study are listed as authors or given proper
credit
in the acknowledgements; that I have obtained permission for and
acknowledged
the source of any excerpts from other copyright works; and that to the
best of
my knowledge the paper contains no statements which are libellous,
unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
<i>R</i>-3-Boc-Bromalaninemethylester
;
_publ_section_title_footnote     # remove if not required
.

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

# NB if using publCIF, the Author database tool might prove useful
# (see the Tools menu in publCIF)

loop_
_publ_author_address
_publ_author_footnote
_publ_author_email
;
Institut fuer Anorganische und Angewandte Chemie
Universitaet Hamburg
Martin-Luther-King-Platz 6
D-20146 Hamburg
Germany
;
.
;
kraehmer@chemie.uni-hamburg.de
;
;
Institut fuer Anorganische und Angewandte Chemie
Universitaet Hamburg
Martin-Luther-King-Platz 6
D-20146 Hamburg
Germany
;
.
;
rehder@chemie.uni-hamburg.de
;

#==============================================================================

# TEXT

_publ_section_synopsis           .
_publ_section_abstract           
;
(type here to add abstract)
;

_publ_section_comment            
;
(type here to add)
;

_publ_section_acknowledgements   # remove if not required
;
?
;

_publ_section_references         
;
?
;

_publ_section_figure_captions    
;

;

_publ_section_exptl_prep         
;
(type here to add preparation details)
;

_publ_section_exptl_refinement   
;
(type here to add refinement details)
;
_publ_author_name                D.Rehder

#==============================================================================

data_bocbr
_database_code_depnum_ccdc_archive 'CCDC 855090'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
R-3-(t-Butyloxycarbonyl)-Bromalaninemethylester
;
_chemical_name_common            R-3-Boc-Bromalaninemethylester
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H15 Br N O4'
_chemical_formula_sum            'C9 H15 Br N O4'
_chemical_formula_weight         281.13

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'
Br Br -0.2901 2.4595 '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) '
_symmetry_space_group_name_Hall  P2yb

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.3204(19)
_cell_length_b                   5.1021(10)
_cell_length_c                   13.905(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.297(3)
_cell_angle_gamma                90.00
_cell_volume                     627.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    100
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             286
_exptl_absorpt_coefficient_mu    3.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2917
_exptl_absorpt_correction_T_max  0.9083
_exptl_absorpt_process_details   '(SADABS; SHELDRICK, 1995)'

_exptl_special_details           ?

_diffrn_ambient_temperature      153(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_%        0
_diffrn_reflns_number            4033
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         26.99
_reflns_number_total             2583
_reflns_number_gt                2257
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (SHELDRICK, 2008)'
_computing_publication_material  'SHELXTL (SHELDRICK, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack (1983), 1525 Friedel pairs'
_refine_ls_abs_structure_Flack   0.041(14)
_refine_ls_number_reflns         2583
_refine_ls_number_parameters     140
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
Br1 Br 0.08228(5) 0.46481(9) 0.28057(3) 0.04139(16) Uani 1 1 d . . .
O3 O 0.5784(3) 0.6684(6) 0.3131(2) 0.0274(7) Uani 1 1 d . . .
O1 O 0.3228(3) 0.7614(7) 0.0045(2) 0.0353(7) Uani 1 1 d . . .
O4 O 0.4213(3) 0.9929(9) 0.22396(19) 0.0304(7) Uani 1 1 d . . .
O2 O 0.1289(3) 1.0035(7) 0.0210(2) 0.0329(7) Uani 1 1 d . . .
N1 N 0.3621(4) 0.5609(6) 0.1963(2) 0.0230(7) Uani 1 1 d . . .
C3 C 0.3354(5) 0.9452(15) -0.0724(3) 0.0473(13) Uani 1 1 d . . .
H3A H 0.2417 0.9430 -0.1297 0.071 Uiso 1 1 calc R . .
H3B H 0.4203 0.8944 -0.0957 0.071 Uiso 1 1 calc R . .
H3C H 0.3527 1.1220 -0.0435 0.071 Uiso 1 1 calc R . .
C2 C 0.2151(5) 0.8195(9) 0.0461(3) 0.0255(9) Uani 1 1 d . . .
C1 C 0.2113(4) 0.6205(8) 0.1282(3) 0.0240(9) Uani 1 1 d . . .
H1 H 0.1673 0.4540 0.0934 0.029 Uiso 1 1 calc R . .
C9 C 0.1046(5) 0.7237(8) 0.1836(3) 0.0260(9) Uani 1 1 d . . .
H9A H 0.0046 0.7622 0.1340 0.031 Uiso 1 1 calc R . .
H9B H 0.1455 0.8884 0.2194 0.031 Uiso 1 1 calc R . .
C4 C 0.4516(5) 0.7638(9) 0.2434(3) 0.0244(9) Uani 1 1 d . . .
C5 C 0.6883(5) 0.8554(8) 0.3776(3) 0.0271(9) Uani 1 1 d . . .
C7 C 0.6132(5) 1.0220(8) 0.4393(3) 0.0312(11) Uani 1 1 d . . .
H7A H 0.5483 1.1538 0.3952 0.047 Uiso 1 1 calc R . .
H7B H 0.6910 1.1098 0.4940 0.047 Uiso 1 1 calc R . .
H7C H 0.5519 0.9096 0.4681 0.047 Uiso 1 1 calc R . .
C8 C 0.7612(5) 1.0143(11) 0.3132(4) 0.0380(13) Uani 1 1 d . . .
H8A H 0.7857 0.8987 0.2643 0.057 Uiso 1 1 calc R . .
H8B H 0.8539 1.0961 0.3569 0.057 Uiso 1 1 calc R . .
H8C H 0.6909 1.1507 0.2769 0.057 Uiso 1 1 calc R . .
C6 C 0.8057(5) 0.6723(9) 0.4490(3) 0.0340(10) Uani 1 1 d . . .
H6A H 0.7602 0.5836 0.4948 0.051 Uiso 1 1 calc R . .
H6B H 0.8929 0.7755 0.4887 0.051 Uiso 1 1 calc R . .
H6C H 0.8388 0.5415 0.4089 0.051 Uiso 1 1 calc 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 0.0446(3) 0.0484(3) 0.0365(2) 0.0099(3) 0.02049(18) 0.0022(3)
O3 0.0243(15) 0.0180(15) 0.0320(15) -0.0022(12) -0.0024(13) -0.0020(12)
O1 0.0328(17) 0.045(2) 0.0307(15) 0.0058(15) 0.0141(13) 0.0024(15)
O4 0.0280(14) 0.016(2) 0.0399(14) -0.0035(16) 0.0002(11) 0.0007(15)
O2 0.0336(15) 0.028(2) 0.0356(14) 0.0069(15) 0.0086(12) 0.0082(16)
N1 0.0184(16) 0.0208(18) 0.0245(16) -0.0020(12) -0.0007(14) -0.0010(13)
C3 0.040(2) 0.067(4) 0.038(2) 0.019(3) 0.0159(19) -0.001(4)
C2 0.022(2) 0.028(2) 0.024(2) -0.0030(17) 0.0032(17) -0.0047(18)
C1 0.022(2) 0.018(2) 0.031(2) -0.0022(17) 0.0065(17) -0.0027(16)
C9 0.025(2) 0.028(2) 0.024(2) 0.0018(18) 0.0063(17) -0.0008(18)
C4 0.022(2) 0.024(2) 0.027(2) -0.0018(17) 0.0061(17) -0.0011(17)
C5 0.027(2) 0.018(2) 0.034(2) -0.0024(17) 0.0059(19) -0.0042(17)
C7 0.039(2) 0.021(3) 0.032(2) -0.0031(17) 0.0086(19) -0.0043(18)
C8 0.031(2) 0.042(4) 0.043(2) -0.004(2) 0.0136(19) -0.008(2)
C6 0.034(2) 0.025(2) 0.033(2) -0.0009(18) -0.004(2) 0.0006(19)

_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 C9 1.945(4) . ?
O3 C4 1.361(5) . ?
O3 C5 1.479(5) . ?
O1 C2 1.340(5) . ?
O1 C3 1.454(6) . ?
O4 C4 1.213(7) . ?
O2 C2 1.213(5) . ?
N1 C4 1.362(5) . ?
N1 C1 1.459(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 C1 1.536(6) . ?
C1 C9 1.530(6) . ?
C1 H1 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C5 C8 1.518(6) . ?
C5 C7 1.524(6) . ?
C5 C6 1.540(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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
C4 O3 C5 118.8(3) . . ?
C2 O1 C3 114.8(4) . . ?
C4 N1 C1 118.3(3) . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C2 O1 124.4(4) . . ?
O2 C2 C1 123.9(4) . . ?
O1 C2 C1 111.7(4) . . ?
N1 C1 C9 113.1(3) . . ?
N1 C1 C2 112.2(3) . . ?
C9 C1 C2 108.4(3) . . ?
N1 C1 H1 107.6 . . ?
C9 C1 H1 107.6 . . ?
C2 C1 H1 107.6 . . ?
C1 C9 Br1 110.1(3) . . ?
C1 C9 H9A 109.6 . . ?
Br1 C9 H9A 109.6 . . ?
C1 C9 H9B 109.6 . . ?
Br1 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
O4 C4 O3 126.3(4) . . ?
O4 C4 N1 124.1(4) . . ?
O3 C4 N1 109.5(4) . . ?
O3 C5 C8 109.9(3) . . ?
O3 C5 C7 110.4(3) . . ?
C8 C5 C7 113.8(4) . . ?
O3 C5 C6 102.5(3) . . ?
C8 C5 C6 110.2(4) . . ?
C7 C5 C6 109.6(4) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 O2 2.7(6) . . . . ?
C3 O1 C2 C1 -178.6(4) . . . . ?
C4 N1 C1 C9 -68.8(5) . . . . ?
C4 N1 C1 C2 54.2(5) . . . . ?
O2 C2 C1 N1 -136.0(4) . . . . ?
O1 C2 C1 N1 45.3(5) . . . . ?
O2 C2 C1 C9 -10.4(5) . . . . ?
O1 C2 C1 C9 170.9(3) . . . . ?
N1 C1 C9 Br1 -59.8(4) . . . . ?
C2 C1 C9 Br1 175.1(2) . . . . ?
C5 O3 C4 O4 4.2(6) . . . . ?
C5 O3 C4 N1 -176.6(3) . . . . ?
C1 N1 C4 O4 -8.8(6) . . . . ?
C1 N1 C4 O3 172.0(3) . . . . ?
C4 O3 C5 C8 -66.7(5) . . . . ?
C4 O3 C5 C7 59.6(4) . . . . ?
C4 O3 C5 C6 176.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.080


#==============================================================================

data_brala
_database_code_depnum_ccdc_archive 'CCDC 855112'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        R-3-Bromoalaninemethylesterhydrobromide

_chemical_name_common            Bromoalaninemethylester
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C4 H9 Br N O2, Br'
_chemical_formula_sum            'C4 H9 Br2 N O2'
_chemical_formula_weight         262.94

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  P2ac2ab

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.2531(6)
_cell_length_b                   11.8250(13)
_cell_length_c                   13.8956(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     863.17(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    100
_cell_measurement_theta_min      2
_cell_measurement_theta_max      28

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.023
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    9.331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.420
_exptl_absorpt_correction_T_max  0.521
_exptl_absorpt_process_details   '(SADABS; SHELDRICK, 1995)'

_exptl_special_details           ?

_diffrn_ambient_temperature      153(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'
_diffrn_measurement_method       '\f and \w'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10477
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         28.03
_reflns_number_total             2027
_reflns_number_gt                1885
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (SHELDRICK, 2008)'
_computing_publication_material  'SHELXTL (SHELDRICK, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack (1993), 1090 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.010(13)
_refine_ls_number_reflns         2027
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0481
_refine_ls_wR_factor_gt          0.0476
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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
Br2 Br 0.11336(5) 0.42797(3) 0.024133(19) 0.02429(8) Uani 1 1 d . . .
Br1 Br 0.29612(6) 1.07930(3) 0.70526(2) 0.03186(9) Uani 1 1 d . . .
N1 N 0.3978(5) 0.83788(19) 0.59702(16) 0.0224(5) Uani 1 1 d . . .
H11A H 0.3750 0.7630 0.5847 0.034 Uiso 1 1 calc R . .
H11B H 0.5183 0.8662 0.5566 0.034 Uiso 1 1 calc R . .
H11C H 0.2485 0.8753 0.5878 0.034 Uiso 1 1 calc R . .
C1 C 0.4822(6) 0.8528(2) 0.6983(2) 0.0204(6) Uani 1 1 d . . .
H1 H 0.6283 0.8003 0.7097 0.024 Uiso 1 1 calc R . .
C2 C 0.2669(6) 0.8174(2) 0.7640(2) 0.0218(6) Uani 1 1 d . . .
C4 C 0.5738(6) 0.9715(2) 0.7171(2) 0.0238(7) Uani 1 1 d . . .
H4A H 0.7096 0.9910 0.6705 0.029 Uiso 1 1 calc R . .
H4B H 0.6468 0.9760 0.7827 0.029 Uiso 1 1 calc R . .
C3 C 0.1380(7) 0.8081(3) 0.9255(2) 0.0401(9) Uani 1 1 d . . .
H3A H -0.0220 0.8438 0.9056 0.060 Uiso 1 1 calc R . .
H3B H 0.1904 0.8386 0.9880 0.060 Uiso 1 1 calc R . .
H3C H 0.1135 0.7262 0.9309 0.060 Uiso 1 1 calc R . .
O1 O 0.3336(4) 0.83157(17) 0.85457(15) 0.0289(5) Uani 1 1 d . . .
O2 O 0.0662(4) 0.78326(19) 0.73534(15) 0.0325(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br2 0.02578(14) 0.02447(15) 0.02261(14) -0.00126(13) 0.00262(12) 0.00116(14)
Br1 0.03670(18) 0.02006(15) 0.03881(18) -0.00419(15) -0.00706(13) 0.00320(14)
N1 0.0198(12) 0.0207(12) 0.0266(13) -0.0043(10) 0.0017(11) -0.0018(10)
C1 0.0160(14) 0.0224(15) 0.0227(15) -0.0007(12) -0.0006(12) -0.0001(11)
C2 0.0226(16) 0.0156(14) 0.0272(16) 0.0012(12) 0.0013(13) 0.0024(11)
C4 0.0196(16) 0.0232(14) 0.0287(16) -0.0027(13) 0.0006(13) -0.0027(11)
C3 0.040(2) 0.054(2) 0.0269(17) 0.0035(15) 0.0078(17) -0.0023(18)
O1 0.0259(12) 0.0373(13) 0.0235(11) 0.0006(9) -0.0001(9) -0.0027(9)
O2 0.0210(12) 0.0469(14) 0.0295(12) 0.0029(10) 0.0006(9) -0.0100(10)

_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 C4 1.944(3) . ?
N1 C1 1.485(4) . ?
N1 H11A 0.9100 . ?
N1 H11B 0.9100 . ?
N1 H11C 0.9100 . ?
C1 C4 1.507(4) . ?
C1 C2 1.513(4) . ?
C1 H1 1.0000 . ?
C2 O2 1.197(3) . ?
C2 O1 1.318(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 O1 1.450(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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 N1 H11A 109.5 . . ?
C1 N1 H11B 109.5 . . ?
H11A N1 H11B 109.5 . . ?
C1 N1 H11C 109.5 . . ?
H11A N1 H11C 109.5 . . ?
H11B N1 H11C 109.5 . . ?
N1 C1 C4 111.7(2) . . ?
N1 C1 C2 108.4(2) . . ?
C4 C1 C2 113.1(3) . . ?
N1 C1 H1 107.8 . . ?
C4 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
O2 C2 O1 126.5(3) . . ?
O2 C2 C1 123.5(3) . . ?
O1 C2 C1 110.0(2) . . ?
C1 C4 Br1 110.9(2) . . ?
C1 C4 H4A 109.5 . . ?
Br1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
Br1 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 O1 C3 115.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O2 0.3(4) . . . . ?
C4 C1 C2 O2 124.7(3) . . . . ?
N1 C1 C2 O1 -178.8(2) . . . . ?
C4 C1 C2 O1 -54.4(3) . . . . ?
N1 C1 C4 Br1 65.6(3) . . . . ?
C2 C1 C4 Br1 -57.0(3) . . . . ?
O2 C2 O1 C3 -3.1(4) . . . . ?
C1 C2 O1 C3 175.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        28.03
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.089


#==============================================================================

data_vamisal
_database_code_depnum_ccdc_archive 'CCDC 855451'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'[VO(OMe)-(MeOH)-(N-(2-salicylidenamino)phenolat)]'
_chemical_name_common            V-Amisal
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N O5 V'
_chemical_formula_weight         341.23

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'
V V 0.3005 0.5294 '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)/n
_symmetry_space_group_name_Hall  -P2yn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1797(17)
_cell_length_b                   21.233(5)
_cell_length_c                   19.471(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.801(5)
_cell_angle_gamma                90.00
_cell_volume                     2925.0(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7206
_exptl_absorpt_correction_T_max  0.9525
_exptl_absorpt_process_details   '(SADABS; SHELDRICK, 1995)'

_exptl_special_details           ?

_diffrn_ambient_temperature      153(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            18138
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_av_sigmaI/netI    0.1883
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.50
_reflns_number_total             6012
_reflns_number_gt                2778
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (SHELDRICK, 2008)'
_computing_publication_material  'SHELXTL (SHELDRICK, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0260P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6012
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   0.786
_refine_ls_restrained_S_all      0.786
_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
V1 V -0.02228(10) 0.03169(4) 0.14810(4) 0.0200(2) Uani 1 1 d . . .
V2 V 0.48266(11) 0.79481(4) 0.13173(5) 0.0220(2) Uani 1 1 d . . .
O1 O -0.1998(4) 0.07696(14) 0.14383(15) 0.0234(8) Uani 1 1 d . . .
O2 O -0.0814(4) -0.03011(14) 0.21344(16) 0.0230(8) Uani 1 1 d . . .
O3 O 0.1400(4) 0.08551(14) 0.11036(16) 0.0246(8) Uani 1 1 d . . .
O4 O -0.0910(4) -0.01868(14) 0.07619(16) 0.0222(8) Uani 1 1 d . . .
O5 O 0.2580(4) -0.02857(14) 0.1641(2) 0.0279(9) Uani 1 1 d . . .
O6 O 0.3076(4) 0.74844(14) 0.12259(16) 0.0260(8) Uani 1 1 d . . .
O7 O 0.6515(4) 0.74387(14) 0.09388(17) 0.0300(9) Uani 1 1 d . . .
O8 O 0.4171(4) 0.85279(14) 0.19975(17) 0.0243(8) Uani 1 1 d . . .
O9 O 0.4175(4) 0.84806(14) 0.06217(17) 0.0266(9) Uani 1 1 d . . .
O10 O 0.7616(5) 0.85540(15) 0.1557(2) 0.0284(10) Uani 1 1 d . . .
N1 N 0.1147(5) 0.06951(18) 0.2460(2) 0.0227(10) Uani 1 1 d . . .
N2 N 0.6132(5) 0.75349(19) 0.2294(2) 0.0289(11) Uani 1 1 d . . .
C1 C 0.2000(6) 0.1227(2) 0.2549(3) 0.0247(12) Uani 1 1 d . . .
H1 H 0.2373 0.1374 0.3013 0.030 Uiso 1 1 calc R . .
C2 C 0.2427(6) 0.1615(2) 0.1987(3) 0.0217(12) Uani 1 1 d . . .
C3 C 0.3296(6) 0.2202(2) 0.2150(3) 0.0279(13) Uani 1 1 d . . .
H3 H 0.3488 0.2344 0.2620 0.034 Uiso 1 1 calc R . .
C4 C 0.3874(6) 0.2573(2) 0.1653(3) 0.0345(14) Uani 1 1 d . . .
H4 H 0.4441 0.2971 0.1774 0.041 Uiso 1 1 calc R . .
C5 C 0.3622(6) 0.2362(2) 0.0970(3) 0.0311(14) Uani 1 1 d . . .
H5 H 0.4039 0.2617 0.0625 0.037 Uiso 1 1 calc R . .
C6 C 0.2770(6) 0.1785(2) 0.0781(3) 0.0263(13) Uani 1 1 d . . .
H6 H 0.2614 0.1646 0.0310 0.032 Uiso 1 1 calc R . .
C7 C 0.2146(6) 0.1412(2) 0.1287(3) 0.0216(12) Uani 1 1 d . . .
C8 C -0.0243(6) -0.0218(2) 0.2824(3) 0.0187(11) Uani 1 1 d . . .
C9 C -0.0661(6) -0.0638(2) 0.3320(3) 0.0244(12) Uani 1 1 d . . .
H9 H -0.1413 -0.0999 0.3178 0.029 Uiso 1 1 calc R . .
C10 C 0.0004(6) -0.0537(2) 0.4016(3) 0.0280(13) Uani 1 1 d . . .
H10 H -0.0266 -0.0833 0.4352 0.034 Uiso 1 1 calc R . .
C11 C 0.1073(6) -0.0003(2) 0.4230(3) 0.0284(13) Uani 1 1 d . . .
H11 H 0.1511 0.0068 0.4712 0.034 Uiso 1 1 calc R . .
C12 C 0.1498(6) 0.0423(2) 0.3743(3) 0.0259(13) Uani 1 1 d . . .
H12 H 0.2214 0.0790 0.3890 0.031 Uiso 1 1 calc R . .
C13 C 0.0880(6) 0.0314(2) 0.3045(3) 0.0198(11) Uani 1 1 d . . .
C14 C -0.2614(6) -0.0209(2) 0.0276(2) 0.0293(13) Uani 1 1 d . . .
H14A H -0.3280 -0.0603 0.0335 0.044 Uiso 1 1 calc R . .
H14B H -0.2330 -0.0189 -0.0198 0.044 Uiso 1 1 calc R . .
H14C H -0.3415 0.0149 0.0354 0.044 Uiso 1 1 calc R . .
C15 C 0.4477(6) -0.0067(2) 0.1672(3) 0.0303(13) Uani 1 1 d . . .
H15A H 0.4466 0.0386 0.1577 0.046 Uiso 1 1 calc R . .
H15B H 0.5064 -0.0290 0.1323 0.046 Uiso 1 1 calc R . .
H15C H 0.5200 -0.0149 0.2138 0.046 Uiso 1 1 calc R . .
C16 C 0.6924(6) 0.7006(2) 0.2374(3) 0.0299(13) Uani 1 1 d . . .
H16 H 0.7241 0.6841 0.2832 0.036 Uiso 1 1 calc R . .
C17 C 0.7376(6) 0.6638(2) 0.1798(3) 0.0223(12) Uani 1 1 d . . .
C18 C 0.8144(6) 0.6036(2) 0.1956(3) 0.0292(13) Uani 1 1 d . . .
H18 H 0.8258 0.5880 0.2419 0.035 Uiso 1 1 calc R . .
C19 C 0.8724(6) 0.5672(2) 0.1458(3) 0.0293(13) Uani 1 1 d . . .
H19 H 0.9226 0.5264 0.1569 0.035 Uiso 1 1 calc R . .
C20 C 0.8577(6) 0.5904(2) 0.0783(3) 0.0298(13) Uani 1 1 d . . .
H20 H 0.8997 0.5654 0.0434 0.036 Uiso 1 1 calc R . .
C21 C 0.7828(6) 0.6492(2) 0.0614(3) 0.0293(13) Uani 1 1 d . . .
H21 H 0.7747 0.6644 0.0151 0.035 Uiso 1 1 calc R . .
C22 C 0.7189(6) 0.6867(2) 0.1113(3) 0.0216(12) Uani 1 1 d . . .
C23 C 0.4724(6) 0.8440(2) 0.2687(3) 0.0243(12) Uani 1 1 d . . .
C24 C 0.4275(6) 0.8850(2) 0.3181(3) 0.0235(12) Uani 1 1 d . . .
H24 H 0.3538 0.9214 0.3039 0.028 Uiso 1 1 calc R . .
C25 C 0.4883(7) 0.8739(2) 0.3878(3) 0.0300(13) Uani 1 1 d . . .
H25 H 0.4565 0.9023 0.4216 0.036 Uiso 1 1 calc R . .
C26 C 0.5973(7) 0.8205(2) 0.4086(3) 0.0338(14) Uani 1 1 d . . .
H26 H 0.6396 0.8128 0.4568 0.041 Uiso 1 1 calc R . .
C27 C 0.6434(6) 0.7792(2) 0.3601(3) 0.0325(14) Uani 1 1 d . . .
H27 H 0.7172 0.7430 0.3746 0.039 Uiso 1 1 calc R . .
C28 C 0.5825(6) 0.7906(2) 0.2905(3) 0.0238(12) Uani 1 1 d . . .
C29 C 0.2528(7) 0.8505(2) 0.0109(3) 0.0399(15) Uani 1 1 d . . .
H29A H 0.1776 0.8124 0.0137 0.060 Uiso 1 1 calc R . .
H29B H 0.2886 0.8533 -0.0354 0.060 Uiso 1 1 calc R . .
H29C H 0.1780 0.8876 0.0189 0.060 Uiso 1 1 calc R . .
C30 C 0.9488(6) 0.8373(2) 0.1482(3) 0.0395(15) Uani 1 1 d . . .
H30A H 0.9512 0.7921 0.1380 0.059 Uiso 1 1 calc R . .
H30B H 1.0359 0.8462 0.1916 0.059 Uiso 1 1 calc R . .
H30C H 0.9876 0.8611 0.1099 0.059 Uiso 1 1 calc R . .
H31 H 0.261(8) -0.062(2) 0.174(3) 0.059 Uiso 1 1 d . . .
H32 H 0.772(9) 0.881(3) 0.176(3) 0.059 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
V1 0.0161(4) 0.0220(5) 0.0225(5) 0.0001(4) 0.0050(4) -0.0014(4)
V2 0.0180(4) 0.0217(5) 0.0266(6) 0.0025(4) 0.0044(4) 0.0025(4)
O1 0.0173(17) 0.030(2) 0.021(2) 0.0028(16) 0.0005(16) 0.0033(14)
O2 0.0175(17) 0.027(2) 0.025(2) 0.0049(17) 0.0055(16) 0.0003(15)
O3 0.0243(18) 0.023(2) 0.029(2) -0.0024(16) 0.0119(17) -0.0025(14)
O4 0.0131(16) 0.027(2) 0.026(2) -0.0032(16) 0.0007(15) 0.0005(14)
O5 0.0138(16) 0.023(2) 0.048(3) -0.002(2) 0.0082(17) -0.0022(16)
O6 0.0207(17) 0.028(2) 0.027(2) 0.0030(16) -0.0009(16) -0.0018(15)
O7 0.0308(19) 0.019(2) 0.045(2) -0.0002(17) 0.0183(18) 0.0039(15)
O8 0.0196(18) 0.025(2) 0.029(2) -0.0034(17) 0.0058(17) -0.0015(15)
O9 0.0235(18) 0.025(2) 0.030(2) 0.0096(17) 0.0003(17) 0.0022(15)
O10 0.0144(17) 0.025(2) 0.047(3) -0.0023(18) 0.0086(18) 0.0003(16)
N1 0.017(2) 0.025(3) 0.028(3) 0.004(2) 0.007(2) 0.0061(18)
N2 0.013(2) 0.027(3) 0.047(3) 0.003(2) 0.009(2) -0.0039(18)
C1 0.014(2) 0.029(3) 0.032(3) -0.006(3) 0.007(2) 0.003(2)
C2 0.013(2) 0.024(3) 0.028(3) 0.006(2) 0.003(2) 0.007(2)
C3 0.017(3) 0.026(3) 0.040(4) -0.001(3) 0.004(3) 0.000(2)
C4 0.020(3) 0.026(3) 0.060(4) 0.001(3) 0.015(3) 0.002(2)
C5 0.025(3) 0.024(3) 0.047(4) 0.017(3) 0.012(3) 0.006(2)
C6 0.021(3) 0.028(3) 0.030(3) 0.007(3) 0.008(3) 0.004(2)
C7 0.011(2) 0.021(3) 0.033(3) 0.003(2) 0.006(2) 0.004(2)
C8 0.015(2) 0.026(3) 0.018(3) 0.005(2) 0.008(2) 0.007(2)
C9 0.020(3) 0.019(3) 0.037(4) 0.007(3) 0.012(3) 0.005(2)
C10 0.027(3) 0.032(3) 0.027(4) 0.007(3) 0.010(3) 0.000(2)
C11 0.025(3) 0.043(4) 0.018(3) -0.001(3) 0.005(2) 0.006(3)
C12 0.017(3) 0.028(3) 0.034(4) 0.001(3) 0.009(3) 0.001(2)
C13 0.013(2) 0.027(3) 0.021(3) 0.002(3) 0.007(2) 0.005(2)
C14 0.020(3) 0.032(3) 0.033(4) -0.005(3) -0.001(3) -0.002(2)
C15 0.014(3) 0.034(3) 0.042(4) 0.000(3) 0.002(3) -0.005(2)
C16 0.020(3) 0.030(3) 0.039(4) 0.007(3) 0.006(3) -0.007(2)
C17 0.012(2) 0.029(3) 0.027(3) -0.007(3) 0.007(2) -0.008(2)
C18 0.016(3) 0.035(3) 0.037(4) 0.006(3) 0.004(3) -0.005(2)
C19 0.014(3) 0.031(3) 0.044(4) 0.003(3) 0.008(3) 0.000(2)
C20 0.026(3) 0.031(3) 0.034(4) -0.008(3) 0.012(3) 0.002(2)
C21 0.030(3) 0.030(3) 0.030(3) 0.001(3) 0.011(3) 0.002(2)
C22 0.015(2) 0.019(3) 0.033(3) -0.005(2) 0.008(2) -0.005(2)
C23 0.016(3) 0.026(3) 0.033(4) 0.000(3) 0.012(3) -0.004(2)
C24 0.018(3) 0.023(3) 0.031(4) -0.001(2) 0.007(3) 0.001(2)
C25 0.030(3) 0.036(3) 0.028(3) -0.003(3) 0.016(3) 0.000(2)
C26 0.026(3) 0.040(4) 0.034(4) 0.003(3) 0.002(3) -0.002(3)
C27 0.022(3) 0.029(3) 0.048(4) 0.007(3) 0.012(3) 0.004(2)
C28 0.013(3) 0.027(3) 0.033(4) -0.004(3) 0.008(3) -0.005(2)
C29 0.035(3) 0.040(4) 0.044(4) 0.011(3) 0.002(3) 0.006(3)
C30 0.011(3) 0.041(4) 0.068(4) 0.011(3) 0.012(3) 0.002(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
V1 O1 1.587(3) . ?
V1 O4 1.764(3) . ?
V1 O3 1.869(3) . ?
V1 O2 1.925(3) . ?
V1 N1 2.147(4) . ?
V1 O5 2.360(3) . ?
V2 O6 1.583(3) . ?
V2 O9 1.765(3) . ?
V2 O7 1.867(3) . ?
V2 O8 1.924(3) . ?
V2 N2 2.158(4) . ?
V2 O10 2.359(3) . ?
O2 C8 1.347(5) . ?
O3 C7 1.321(5) . ?
O4 C14 1.415(5) . ?
O5 C15 1.430(5) . ?
O5 H31 0.74(5) . ?
O7 C22 1.329(5) . ?
O8 C23 1.347(6) . ?
O9 C29 1.412(5) . ?
O10 C30 1.429(5) . ?
O10 H32 0.67(5) . ?
N1 C1 1.282(5) . ?
N1 C13 1.437(6) . ?
N2 C16 1.256(5) . ?
N2 C28 1.474(6) . ?
C1 C2 1.444(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.406(6) . ?
C2 C7 1.411(6) . ?
C3 C4 1.367(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(6) . ?
C6 H6 0.9500 . ?
C8 C9 1.385(6) . ?
C8 C13 1.411(6) . ?
C9 C10 1.376(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(6) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.448(6) . ?
C16 H16 0.9500 . ?
C17 C22 1.404(6) . ?
C17 C18 1.407(6) . ?
C18 C19 1.360(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(6) . ?
C21 H21 0.9500 . ?
C23 C24 1.376(6) . ?
C23 C28 1.407(6) . ?
C24 C25 1.373(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.370(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.374(6) . ?
C27 H27 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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 O4 102.25(15) . . ?
O1 V1 O3 99.08(14) . . ?
O4 V1 O3 99.63(14) . . ?
O1 V1 O2 100.49(14) . . ?
O4 V1 O2 92.75(14) . . ?
O3 V1 O2 154.01(13) . . ?
O1 V1 N1 93.58(15) . . ?
O4 V1 N1 162.84(14) . . ?
O3 V1 N1 84.16(14) . . ?
O2 V1 N1 77.73(14) . . ?
O1 V1 O5 173.85(15) . . ?
O4 V1 O5 83.85(13) . . ?
O3 V1 O5 78.98(12) . . ?
O2 V1 O5 79.76(12) . . ?
N1 V1 O5 80.45(13) . . ?
O6 V2 O9 102.14(16) . . ?
O6 V2 O7 98.74(15) . . ?
O9 V2 O7 99.98(15) . . ?
O6 V2 O8 101.10(15) . . ?
O9 V2 O8 93.11(15) . . ?
O7 V2 O8 153.32(14) . . ?
O6 V2 N2 93.65(15) . . ?
O9 V2 N2 162.78(15) . . ?
O7 V2 N2 84.18(15) . . ?
O8 V2 N2 76.95(15) . . ?
O6 V2 O10 173.08(15) . . ?
O9 V2 O10 84.72(14) . . ?
O7 V2 O10 78.92(13) . . ?
O8 V2 O10 79.26(12) . . ?
N2 V2 O10 79.67(14) . . ?
C8 O2 V1 120.3(3) . . ?
C7 O3 V1 133.8(3) . . ?
C14 O4 V1 130.1(3) . . ?
C15 O5 V1 127.9(3) . . ?
C15 O5 H31 108(4) . . ?
V1 O5 H31 123(4) . . ?
C22 O7 V2 131.3(3) . . ?
C23 O8 V2 122.2(3) . . ?
C29 O9 V2 130.3(3) . . ?
C30 O10 V2 127.9(3) . . ?
C30 O10 H32 105(5) . . ?
V2 O10 H32 125(6) . . ?
C1 N1 C13 121.0(4) . . ?
C1 N1 V1 125.9(3) . . ?
C13 N1 V1 113.0(3) . . ?
C16 N2 C28 120.3(5) . . ?
C16 N2 V2 126.3(4) . . ?
C28 N2 V2 113.1(3) . . ?
N1 C1 C2 123.9(5) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C7 118.4(5) . . ?
C3 C2 C1 118.5(5) . . ?
C7 C2 C1 122.9(4) . . ?
C4 C3 C2 121.8(5) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
O3 C7 C6 118.8(5) . . ?
O3 C7 C2 121.3(4) . . ?
C6 C7 C2 119.8(5) . . ?
O2 C8 C9 123.0(4) . . ?
O2 C8 C13 118.1(4) . . ?
C9 C8 C13 118.9(5) . . ?
C10 C9 C8 120.4(5) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.2(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C8 120.5(4) . . ?
C12 C13 N1 128.6(4) . . ?
C8 C13 N1 110.8(4) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 122.8(5) . . ?
N2 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C22 C17 C18 119.5(5) . . ?
C22 C17 C16 123.4(5) . . ?
C18 C17 C16 116.9(5) . . ?
C19 C18 C17 121.1(5) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.4(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.9(5) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
O7 C22 C21 119.5(5) . . ?
O7 C22 C17 122.0(4) . . ?
C21 C22 C17 118.4(5) . . ?
O8 C23 C24 123.1(5) . . ?
O8 C23 C28 117.8(4) . . ?
C24 C23 C28 119.1(5) . . ?
C25 C24 C23 120.6(5) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 119.7(5) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 120.5(5) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 119.7(5) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C27 C28 C23 120.5(5) . . ?
C27 C28 N2 129.5(5) . . ?
C23 C28 N2 110.0(5) . . ?
O9 C29 H29A 109.5 . . ?
O9 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O9 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O10 C30 H30A 109.5 . . ?
O10 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O10 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.084