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

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#                                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.
#
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#  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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#  data retrieval see:
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data_schm60_compound_26b

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 10,10-diethyl-2-(2-hydroxyethyl)-6,8-dioxo-6,7,8,10-tetrahydro-1H-imidazo-
[2',1:3,4][1,4,2]diazaborolo[1,5-c]pyrimidin-4-iunm-10-uide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 B N4 O3'
_chemical_formula_sum            'C13 H19 B N4 O3'
_chemical_formula_weight         290.13

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   8.6058(4)
_cell_length_b                   7.5126(3)
_cell_length_c                   22.4696(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.873(2)
_cell_angle_gamma                90
_cell_volume                     1439.01(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    85
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9055
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   'SADABS (Shedlrcik, 2008)'

_exptl_special_details           
;
 dx = 40 mm, 120 sec./deg., 1 deg., 8 sets, 711 frames,
11965 refl. postref.
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in φ and ω, 1°'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            23003
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.673
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3291
_reflns_number_gt                2748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  publCif

_refine_special_details          
;
 The ethylhydroxy group is disordered use of constraints (EADP) and 
restrains (DFIX, SADI).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0745P)²+3.7762P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3291
_refine_ls_number_parameters     190
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0906
_refine_ls_wR_factor_ref         0.2201
_refine_ls_wR_factor_gt          0.2091
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.125
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7177(4) 0.6358(5) 0.36511(13) 0.0265(6) Uani 1 1 d . . . . .
N1 N 0.7148(3) 0.7307(3) 0.42986(10) 0.0250(5) Uani 1 1 d . . . . .
C2 C 0.8345(3) 0.8262(4) 0.46082(13) 0.0289(6) Uani 1 1 d . . . . .
O2 O 0.9614(2) 0.8462(3) 0.44256(10) 0.0412(6) Uani 1 1 d . . . . .
N3 N 0.8051(3) 0.8983(3) 0.51473(10) 0.0287(5) Uani 1 1 d D . . . .
H3 H 0.880(3) 0.966(4) 0.5335(14) 0.034 Uiso 1 1 d D U . . .
C4 C 0.6695(3) 0.8796(4) 0.54085(12) 0.0270(6) Uani 1 1 d . . . . .
O4 O 0.6606(3) 0.9477(3) 0.59018(9) 0.0369(5) Uani 1 1 d . . . . .
C5 C 0.5458(3) 0.7830(4) 0.50549(11) 0.0251(6) Uani 1 1 d . . . . .
H5 H 0.4475 0.7641 0.5192 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5753(3) 0.7205(3) 0.45202(11) 0.0216(5) Uani 1 1 d . . . . .
N7 N 0.4699(3) 0.6294(3) 0.40908(10) 0.0238(5) Uani 1 1 d . . . . .
C8 C 0.3117(3) 0.5859(4) 0.40233(14) 0.0337(7) Uani 1 1 d . . . . .
H8 H 0.2381 0.6134 0.4289 0.040 Uiso 1 1 calc R U . . .
C9 C 0.2852(3) 0.4965(5) 0.35018(16) 0.0435(9) Uani 1 1 d . . . . .
H9 H 0.1876 0.4475 0.3329 0.052 Uiso 1 1 calc R U . . .
N10 N 0.4256(3) 0.4879(4) 0.32571(11) 0.0334(6) Uani 1 1 d D . . . .
C11 C 0.5374(3) 0.5710(4) 0.36176(11) 0.0243(6) Uani 1 1 d . . . . .
C12 C 0.4522(4) 0.4016(6) 0.26894(16) 0.0548(11) Uani 1 1 d D . . . .
H12A H 0.3806 0.2985 0.2611 0.066 Uiso 0.641(5) 1 calc R U P A 1
H12B H 0.5613 0.3566 0.2729 0.066 Uiso 0.641(5) 1 calc R U P A 1
H12C H 0.4757 0.2741 0.2770 0.066 Uiso 0.359(5) 1 calc R U P A 2
H12D H 0.5456 0.4560 0.2550 0.066 Uiso 0.359(5) 1 calc R U P A 2
C13 C 0.4236(6) 0.5342(7) 0.2144(2) 0.0450(11) Uiso 0.641(5) 1 d D . P A 1
H13A H 0.4947 0.6379 0.2216 0.054 Uiso 0.641(5) 1 calc R U P A 1
H13B H 0.4452 0.4741 0.1771 0.054 Uiso 0.641(5) 1 calc R U P A 1
O14 O 0.2662(6) 0.5909(7) 0.2080(2) 0.0664(12) Uiso 0.641(5) 1 d D . P A 1
H14 H 0.2492 0.6620 0.1790 0.100 Uiso 0.641(5) 1 calc R U P A 1
C13A C 0.3134(9) 0.4156(10) 0.2183(3) 0.0450(11) Uiso 0.359(5) 1 d D . P A 2
H13C H 0.3223 0.3300 0.1854 0.054 Uiso 0.359(5) 1 calc R U P A 2
H13D H 0.2113 0.4000 0.2332 0.054 Uiso 0.359(5) 1 calc R U P A 2
O14A O 0.3379(12) 0.5955(10) 0.2006(4) 0.0664(12) Uiso 0.359(5) 1 d D . P A 2
H14A H 0.2689 0.6235 0.1720 0.100 Uiso 0.359(5) 1 calc R U P A 2
C15 C 0.8446(3) 0.4776(5) 0.36909(14) 0.0358(7) Uani 1 1 d . . . . .
H15A H 0.8351 0.4183 0.3294 0.043 Uiso 1 1 calc R U . . .
H15B H 0.9505 0.5312 0.3766 0.043 Uiso 1 1 calc R U . . .
C16 C 0.8335(5) 0.3361(6) 0.41641(19) 0.0610(12) Uani 1 1 d . . . . .
H16A H 0.9160 0.2471 0.4146 0.092 Uiso 1 1 calc R U . . .
H16B H 0.7306 0.2782 0.4090 0.092 Uiso 1 1 calc R U . . .
H16C H 0.8468 0.3914 0.4563 0.092 Uiso 1 1 calc R U . . .
C17 C 0.7351(5) 0.7837(5) 0.31457(15) 0.0471(9) Uani 1 1 d . . . . .
H17A H 0.8442 0.8287 0.3211 0.057 Uiso 1 1 calc R U . . .
H17B H 0.7194 0.7242 0.2749 0.057 Uiso 1 1 calc R U . . .
C18 C 0.6268(7) 0.9403(5) 0.31178(19) 0.0686(14) Uani 1 1 d . . . . .
H18A H 0.6481 1.0202 0.2794 0.103 Uiso 1 1 calc R U . . .
H18B H 0.6435 1.0043 0.3501 0.103 Uiso 1 1 calc R U . . .
H18C H 0.5179 0.8990 0.3040 0.103 Uiso 1 1 calc R U . . .


_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
B1 C15 1.608(4) . ?
B1 C17 1.610(5) . ?
B1 C11 1.618(4) . ?
B1 N1 1.623(3) . ?
N1 C6 1.364(3) . ?
N1 C2 1.365(3) . ?
C2 O2 1.227(3) . ?
C2 N3 1.382(3) . ?
N3 C4 1.383(4) . ?
N3 H3 0.880(18) . ?
C4 O4 1.233(3) . ?
C4 C5 1.435(4) . ?
C5 C6 1.346(4) . ?
C5 H5 0.9500 . ?
C6 N7 1.408(3) . ?
N7 C11 1.353(3) . ?
N7 C8 1.388(3) . ?
C8 C9 1.343(4) . ?
C8 H8 0.9500 . ?
C9 N10 1.396(4) . ?
C9 H9 0.9500 . ?
N10 C11 1.326(3) . ?
N10 C12 1.477(4) . ?
C12 C13A 1.536(5) . ?
C12 C13 1.573(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C13 O14 1.409(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O14 H14 0.8400 . ?
C13A O14A 1.432(6) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
O14A H14A 0.8400 . ?
C15 C16 1.516(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.497(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C15 B1 C17 114.9(3) . . ?
C15 B1 C11 114.8(2) . . ?
C17 B1 C11 110.8(3) . . ?
C15 B1 N1 111.6(2) . . ?
C17 B1 N1 110.1(2) . . ?
C11 B1 N1 92.37(19) . . ?
C6 N1 C2 119.0(2) . . ?
C6 N1 B1 115.2(2) . . ?
C2 N1 B1 125.8(2) . . ?
O2 C2 N1 122.6(2) . . ?
O2 C2 N3 121.5(3) . . ?
N1 C2 N3 115.9(2) . . ?
C2 N3 C4 126.8(2) . . ?
C2 N3 H3 116(2) . . ?
C4 N3 H3 117(2) . . ?
O4 C4 N3 120.0(3) . . ?
O4 C4 C5 125.1(3) . . ?
N3 C4 C5 114.9(2) . . ?
C6 C5 C4 117.0(2) . . ?
C6 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
C5 C6 N1 126.1(2) . . ?
C5 C6 N7 126.8(2) . . ?
N1 C6 N7 107.1(2) . . ?
C11 N7 C8 111.0(2) . . ?
C11 N7 C6 113.0(2) . . ?
C8 N7 C6 136.0(2) . . ?
C9 C8 N7 105.1(3) . . ?
C9 C8 H8 127.5 . . ?
N7 C8 H8 127.5 . . ?
C8 C9 N10 108.3(3) . . ?
C8 C9 H9 125.8 . . ?
N10 C9 H9 125.8 . . ?
C11 N10 C9 109.4(2) . . ?
C11 N10 C12 123.3(2) . . ?
C9 N10 C12 127.3(3) . . ?
N10 C11 N7 106.2(2) . . ?
N10 C11 B1 141.4(2) . . ?
N7 C11 B1 112.2(2) . . ?
N10 C12 C13A 114.4(4) . . ?
N10 C12 C13 111.7(3) . . ?
N10 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N10 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N10 C12 H12C 108.7 . . ?
C13A C12 H12C 108.7 . . ?
N10 C12 H12D 108.7 . . ?
C13A C12 H12D 108.7 . . ?
H12C C12 H12D 107.6 . . ?
O14 C13 C12 108.4(4) . . ?
O14 C13 H13A 110.0 . . ?
C12 C13 H13A 110.0 . . ?
O14 C13 H13B 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C13 O14 H14 109.5 . . ?
O14A C13A C12 98.1(5) . . ?
O14A C13A H13C 112.1 . . ?
C12 C13A H13C 112.1 . . ?
O14A C13A H13D 112.1 . . ?
C12 C13A H13D 112.1 . . ?
H13C C13A H13D 109.8 . . ?
C13A O14A H14A 109.5 . . ?
C16 C15 B1 116.7(3) . . ?
C16 C15 H15A 108.1 . . ?
B1 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
B1 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 B1 117.0(3) . . ?
C18 C17 H17A 108.0 . . ?
B1 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
B1 C17 H17B 108.0 . . ?
H17A C17 H17B 107.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C15 B1 N1 C6 -118.9(3) . . . . ?
C17 B1 N1 C6 112.2(3) . . . . ?
C11 B1 N1 C6 -1.0(3) . . . . ?
C15 B1 N1 C2 65.4(4) . . . . ?
C17 B1 N1 C2 -63.5(4) . . . . ?
C11 B1 N1 C2 -176.7(3) . . . . ?
C6 N1 C2 O2 -177.4(3) . . . . ?
B1 N1 C2 O2 -1.9(5) . . . . ?
C6 N1 C2 N3 3.2(4) . . . . ?
B1 N1 C2 N3 178.8(3) . . . . ?
O2 C2 N3 C4 -177.6(3) . . . . ?
N1 C2 N3 C4 1.8(5) . . . . ?
C2 N3 C4 O4 178.1(3) . . . . ?
C2 N3 C4 C5 -3.8(4) . . . . ?
O4 C4 C5 C6 178.7(3) . . . . ?
N3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 N1 4.3(4) . . . . ?
C4 C5 C6 N7 -177.1(3) . . . . ?
C2 N1 C6 C5 -6.5(4) . . . . ?
B1 N1 C6 C5 177.5(3) . . . . ?
C2 N1 C6 N7 174.7(2) . . . . ?
B1 N1 C6 N7 -1.3(3) . . . . ?
C5 C6 N7 C11 -175.1(3) . . . . ?
N1 C6 N7 C11 3.6(3) . . . . ?
C5 C6 N7 C8 6.1(5) . . . . ?
N1 C6 N7 C8 -175.1(3) . . . . ?
C11 N7 C8 C9 1.1(4) . . . . ?
C6 N7 C8 C9 179.9(3) . . . . ?
N7 C8 C9 N10 -0.5(4) . . . . ?
C8 C9 N10 C11 -0.3(4) . . . . ?
C8 C9 N10 C12 179.6(3) . . . . ?
C9 N10 C11 N7 0.9(4) . . . . ?
C12 N10 C11 N7 -178.9(3) . . . . ?
C9 N10 C11 B1 -172.9(4) . . . . ?
C12 N10 C11 B1 7.2(6) . . . . ?
C8 N7 C11 N10 -1.3(3) . . . . ?
C6 N7 C11 N10 179.6(2) . . . . ?
C8 N7 C11 B1 174.5(2) . . . . ?
C6 N7 C11 B1 -4.5(3) . . . . ?
C15 B1 C11 N10 -68.1(5) . . . . ?
C17 B1 C11 N10 64.2(5) . . . . ?
N1 B1 C11 N10 176.7(4) . . . . ?
C15 B1 C11 N7 118.3(3) . . . . ?
C17 B1 C11 N7 -109.4(3) . . . . ?
N1 B1 C11 N7 3.1(3) . . . . ?
C11 N10 C12 C13A -144.4(4) . . . . ?
C9 N10 C12 C13A 35.7(6) . . . . ?
C11 N10 C12 C13 -89.9(4) . . . . ?
C9 N10 C12 C13 90.3(5) . . . . ?
N10 C12 C13 O14 -61.3(5) . . . . ?
C13A C12 C13 O14 43.0(6) . . . . ?
N10 C12 C13A O14A 78.0(7) . . . . ?
C13 C12 C13A O14A -20.5(5) . . . . ?
C17 B1 C15 C16 179.5(3) . . . . ?
C11 B1 C15 C16 -50.2(4) . . . . ?
N1 B1 C15 C16 53.3(4) . . . . ?
C15 B1 C17 C18 -176.0(3) . . . . ?
C11 B1 C17 C18 51.8(4) . . . . ?
N1 B1 C17 C18 -48.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O2 0.880(18) 1.99(2) 2.848(3) 166(3) 3_776
C12 H12A O14 0.99 2.18 3.084(7) 151.3 2_545
O14 H14 O4 0.84 2.20 2.695(5) 118.0 4_575
O14A H14A O4 0.84 2.02 2.748(9) 145.3 4_575

_refine_diff_density_max         1.401
_refine_diff_density_min         -1.198
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-2


# start Validation Reply Form
_vrf_DIFMN02_schm60              
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: in the insotropically refined disordered 
hydroxyethyl group
;
_vrf_DIFMX01_schm60              
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: in the insotropically refined disordered 
hydroxyethyl group
;
_vrf_PLAT097_schm60              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.40 eA-3 
RESPONSE: in the insotropically refined disordered 
hydroxyethyl group
;
_vrf_PLAT098_schm60              
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -1.20 eA-3 
RESPONSE: in the insotropically refined disordered 
hydroxyethyl group
;
_vrf_PLAT201_schm60              
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          2      
RESPONSE: disordered hydroxyethyl group
;
_vrf_PLAT413_schm60              
;
PROBLEM: Short Inter XH3 .. XHn     H18C   ..  H13D    ..       2.03 Ang. 
RESPONSE: due to disorder as well as short intramolecular distances
;
_database_code_depnum_ccdc_archive 'CCDC 976125'
#######################################################################
#
#                 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_schm59_o_compound_26d

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 1-benzyl-10,10-diethyl-6,8-dioxo-6,7,8,10-tetrahydro-1H-imidazo
[2',1:3,4][1,4,2]diazaborolo[1,5-c]pyrimidin-4-ium-10-uide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 B N4 O2'
_chemical_formula_sum            'C18 H21 B N4 O2'
_chemical_formula_weight         336.20

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   35.612(3)
_cell_length_b                   8.829(1)
_cell_length_c                   11.287(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3548.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    182
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9352
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 dx = 60 mm, 140 sec./deg., 0.5 deg., 3 sets, 898 frames,
10883 refl. postref.
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in φ and ω, 0.5°'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            22454
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             7540
_reflns_number_gt                6456
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     0.843
_reflns_Friedel_fraction_full    0.891

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  publCif

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0528P)²+0.8778P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7540
_refine_ls_number_parameters     457
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.74525(9) 0.2835(4) 0.8398(3) 0.0239(7) Uani 1 1 d . . . . .
N1 N 0.70667(7) 0.2569(3) 0.7652(2) 0.0244(6) Uani 1 1 d . . . . .
C2 C 0.69154(9) 0.1194(3) 0.7366(3) 0.0281(7) Uani 1 1 d . . . . .
O2 O 0.70596(7) -0.0007(3) 0.7614(2) 0.0419(6) Uani 1 1 d . . . . .
N3 N 0.65788(7) 0.1253(3) 0.6749(2) 0.0271(6) Uani 1 1 d D . . . .
H3 H 0.6500(9) 0.039(3) 0.649(3) 0.032 Uiso 1 1 d D U . . .
C4 C 0.63853(9) 0.2531(4) 0.6402(3) 0.0269(7) Uani 1 1 d . . . . .
O4 O 0.60861(6) 0.2405(3) 0.5846(2) 0.0329(5) Uani 1 1 d . . . . .
C5 C 0.65578(8) 0.3934(4) 0.6732(3) 0.0262(6) Uani 1 1 d . . . . .
H5 H 0.6447 0.4881 0.6542 0.031 Uiso 1 1 calc R U . . .
C6 C 0.68851(8) 0.3846(3) 0.7325(3) 0.0233(6) Uani 1 1 d . . . . .
N7 N 0.71001(6) 0.5080(3) 0.7714(2) 0.0238(5) Uani 1 1 d . . . . .
C8 C 0.70692(8) 0.6629(3) 0.7652(3) 0.0244(6) Uani 1 1 d . . . . .
H8 H 0.6876 0.7198 0.7278 0.029 Uiso 1 1 calc R U . . .
C9 C 0.73710(8) 0.7171(3) 0.8233(3) 0.0252(6) Uani 1 1 d . . . . .
H9 H 0.7432 0.8207 0.8347 0.030 Uiso 1 1 calc R U . . .
N10 N 0.75766(6) 0.5930(3) 0.8636(2) 0.0243(5) Uani 1 1 d . . . . .
C11 C 0.74127(7) 0.4645(3) 0.8316(3) 0.0244(6) Uani 1 1 d . . . . .
C12 C 0.79286(8) 0.6039(4) 0.9325(3) 0.0301(7) Uani 1 1 d . . . . .
H12A H 0.8007 0.5012 0.9576 0.036 Uiso 1 1 calc R U . . .
H12B H 0.7884 0.6650 1.0046 0.036 Uiso 1 1 calc R U . . .
C13 C 0.82389(8) 0.6759(4) 0.8601(3) 0.0295(7) Uani 1 1 d . . . . .
C14 C 0.84797(8) 0.5856(4) 0.7948(3) 0.0350(8) Uani 1 1 d . . . . .
H14 H 0.8454 0.4785 0.7970 0.042 Uiso 1 1 calc R U . . .
C15 C 0.87587(9) 0.6508(5) 0.7262(4) 0.0437(9) Uani 1 1 d . . . . .
H15 H 0.8926 0.5882 0.6826 0.052 Uiso 1 1 calc R U . . .
C16 C 0.87942(10) 0.8058(5) 0.7211(4) 0.0457(10) Uani 1 1 d . . . . .
H16 H 0.8983 0.8501 0.6730 0.055 Uiso 1 1 calc R U . . .
C17 C 0.85545(9) 0.8973(4) 0.7860(4) 0.0411(9) Uani 1 1 d . . . . .
H17 H 0.8578 1.0043 0.7822 0.049 Uiso 1 1 calc R U . . .
C18 C 0.82802(9) 0.8316(4) 0.8565(3) 0.0343(8) Uani 1 1 d . . . . .
H18 H 0.8120 0.8940 0.9027 0.041 Uiso 1 1 calc R U . . .
C19 C 0.78100(9) 0.2183(4) 0.7689(3) 0.0359(8) Uani 1 1 d . . . . .
H19A H 0.8039 0.2409 0.8155 0.043 Uiso 1 1 calc R U . . .
H19B H 0.7786 0.1067 0.7643 0.043 Uiso 1 1 calc R U . . .
C20 C 0.78661(11) 0.2793(6) 0.6435(4) 0.0534(11) Uani 1 1 d . . . . .
H20A H 0.8091 0.2333 0.6085 0.080 Uiso 1 1 calc R U . . .
H20B H 0.7897 0.3896 0.6464 0.080 Uiso 1 1 calc R U . . .
H20C H 0.7646 0.2543 0.5950 0.080 Uiso 1 1 calc R U . . .
C21 C 0.74115(10) 0.2207(4) 0.9735(3) 0.0367(8) Uani 1 1 d . . . . .
H21A H 0.7398 0.1088 0.9705 0.044 Uiso 1 1 calc R U . . .
H21B H 0.7642 0.2479 1.0180 0.044 Uiso 1 1 calc R U . . .
C22 C 0.70753(12) 0.2785(6) 1.0418(4) 0.0583(12) Uani 1 1 d . . . . .
H22A H 0.7076 0.2348 1.1216 0.087 Uiso 1 1 calc R U . . .
H22B H 0.6844 0.2489 1.0006 0.087 Uiso 1 1 calc R U . . .
H22C H 0.7088 0.3891 1.0473 0.087 Uiso 1 1 calc R U . . .
B1A B 0.50278(10) 0.7793(4) 0.3247(3) 0.0261(7) Uani 1 1 d . . . . .
N1A N 0.54180(7) 0.8068(3) 0.3939(2) 0.0228(5) Uani 1 1 d . . . . .
C2A C 0.55577(9) 0.9456(3) 0.4267(3) 0.0276(7) Uani 1 1 d . . . . .
O2A O 0.54006(6) 1.0635(3) 0.4033(2) 0.0385(6) Uani 1 1 d . . . . .
N3A N 0.58910(7) 0.9433(3) 0.4898(2) 0.0263(6) Uani 1 1 d D . . . .
H3A H 0.5974(9) 1.032(3) 0.511(3) 0.032 Uiso 1 1 d D U . . .
C4A C 0.61050(8) 0.8173(3) 0.5171(3) 0.0249(7) Uani 1 1 d . . . . .
O4A O 0.64058(6) 0.8335(3) 0.5706(2) 0.0329(5) Uani 1 1 d . . . . .
C5A C 0.59455(8) 0.6762(3) 0.4812(3) 0.0237(6) Uani 1 1 d . . . . .
H5A H 0.6069 0.5829 0.4970 0.028 Uiso 1 1 calc R U . . .
C6A C 0.56148(8) 0.6806(3) 0.4242(3) 0.0224(6) Uani 1 1 d . . . . .
N7A N 0.54031(6) 0.5557(3) 0.3859(2) 0.0219(5) Uani 1 1 d . . . . .
C8A C 0.54333(8) 0.4003(3) 0.3939(3) 0.0254(6) Uani 1 1 d . . . . .
H8A H 0.5630 0.3440 0.4297 0.031 Uiso 1 1 calc R U . . .
C9A C 0.51248(8) 0.3453(3) 0.3400(3) 0.0273(6) Uani 1 1 d . . . . .
H9A H 0.5063 0.2414 0.3301 0.033 Uiso 1 1 calc R U . . .
N10A N 0.49131(6) 0.4687(3) 0.3013(2) 0.0252(5) Uani 1 1 d . . . . .
C11A C 0.50814(8) 0.5971(3) 0.3298(2) 0.0229(6) Uani 1 1 d . . . . .
C12A C 0.45551(9) 0.4571(4) 0.2366(3) 0.0308(7) Uani 1 1 d . . . . .
H12C H 0.4599 0.4050 0.1601 0.037 Uiso 1 1 calc R U . . .
H12D H 0.4460 0.5601 0.2192 0.037 Uiso 1 1 calc R U . . .
C13A C 0.42635(8) 0.3715(4) 0.3060(3) 0.0291(7) Uani 1 1 d . . . . .
C14A C 0.42243(9) 0.2165(4) 0.2920(3) 0.0321(7) Uani 1 1 d . . . . .
H14A H 0.4379 0.1640 0.2372 0.039 Uiso 1 1 calc R U . . .
C15A C 0.39573(9) 0.1372(4) 0.3581(4) 0.0429(9) Uani 1 1 d . . . . .
H15A H 0.3933 0.0306 0.3494 0.051 Uiso 1 1 calc R U . . .
C16A C 0.37310(9) 0.2142(5) 0.4356(4) 0.0477(10) Uani 1 1 d . . . . .
H16A H 0.3546 0.1608 0.4796 0.057 Uiso 1 1 calc R U . . .
C17A C 0.37690(9) 0.3672(5) 0.4504(4) 0.0488(10) Uani 1 1 d . . . . .
H17A H 0.3612 0.4192 0.5050 0.059 Uiso 1 1 calc R U . . .
C18A C 0.40337(9) 0.4463(4) 0.3863(4) 0.0399(8) Uani 1 1 d . . . . .
H18A H 0.4059 0.5525 0.3972 0.048 Uiso 1 1 calc R U . . .
C19A C 0.46770(9) 0.8319(4) 0.4039(4) 0.0401(9) Uani 1 1 d . . . . .
H19C H 0.4671 0.9440 0.4052 0.048 Uiso 1 1 calc R U . . .
H19D H 0.4444 0.7969 0.3648 0.048 Uiso 1 1 calc R U . . .
C20A C 0.46753(12) 0.7751(5) 0.5313(4) 0.0503(10) Uani 1 1 d . . . . .
H20D H 0.4452 0.8137 0.5722 0.075 Uiso 1 1 calc R U . . .
H20E H 0.4902 0.8108 0.5720 0.075 Uiso 1 1 calc R U . . .
H20F H 0.4671 0.6641 0.5316 0.075 Uiso 1 1 calc R U . . .
C21A C 0.50425(11) 0.8440(4) 0.1923(3) 0.0423(9) Uani 1 1 d . . . . .
H21C H 0.4807 0.8149 0.1515 0.051 Uiso 1 1 calc R U . . .
H21D H 0.5048 0.9560 0.1964 0.051 Uiso 1 1 calc R U . . .
C22A C 0.53684(14) 0.7920(6) 0.1178(4) 0.0581(12) Uani 1 1 d . . . . .
H22D H 0.5351 0.8376 0.0388 0.087 Uiso 1 1 calc R U . . .
H22E H 0.5363 0.6814 0.1106 0.087 Uiso 1 1 calc R U . . .
H22F H 0.5604 0.8231 0.1553 0.087 Uiso 1 1 calc R U . . .


_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
B1 C11 1.607(5) . ?
B1 C19 1.610(5) . ?
B1 C21 1.615(5) . ?
B1 N1 1.628(4) . ?
N1 C6 1.351(4) . ?
N1 C2 1.367(4) . ?
C2 O2 1.211(4) . ?
C2 N3 1.388(4) . ?
N3 C4 1.379(4) . ?
N3 H3 0.86(2) . ?
C4 O4 1.242(4) . ?
C4 C5 1.432(5) . ?
C5 C6 1.346(4) . ?
C5 H5 0.9500 . ?
C6 N7 1.402(4) . ?
N7 C11 1.359(4) . ?
N7 C8 1.374(4) . ?
C8 C9 1.347(4) . ?
C8 H8 0.9500 . ?
C9 N10 1.394(4) . ?
C9 H9 0.9500 . ?
N10 C11 1.327(4) . ?
N10 C12 1.478(3) . ?
C12 C13 1.514(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.383(5) . ?
C13 C14 1.384(5) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.528(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.512(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
B1A C21A 1.601(5) . ?
B1A C19A 1.604(5) . ?
B1A N1A 1.612(4) . ?
B1A C11A 1.622(5) . ?
N1A C6A 1.360(4) . ?
N1A C2A 1.374(4) . ?
C2A O2A 1.211(4) . ?
C2A N3A 1.384(4) . ?
N3A C4A 1.383(4) . ?
N3A H3A 0.87(2) . ?
C4A O4A 1.238(4) . ?
C4A C5A 1.428(4) . ?
C5A C6A 1.343(4) . ?
C5A H5A 0.9500 . ?
C6A N7A 1.404(4) . ?
N7A C11A 1.359(4) . ?
N7A C8A 1.379(4) . ?
C8A C9A 1.346(4) . ?
C8A H8A 0.9500 . ?
C9A N10A 1.395(4) . ?
C9A H9A 0.9500 . ?
N10A C11A 1.321(4) . ?
N10A C12A 1.473(4) . ?
C12A C13A 1.504(5) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A C14A 1.385(5) . ?
C13A C18A 1.388(5) . ?
C14A C15A 1.397(5) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.370(6) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.369(6) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.378(5) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
C19A C20A 1.523(6) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C21A C22A 1.505(6) . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 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
C11 B1 C19 113.4(3) . . ?
C11 B1 C21 112.8(3) . . ?
C19 B1 C21 114.4(3) . . ?
C11 B1 N1 92.2(2) . . ?
C19 B1 N1 111.0(3) . . ?
C21 B1 N1 110.9(2) . . ?
C6 N1 C2 119.2(3) . . ?
C6 N1 B1 115.1(2) . . ?
C2 N1 B1 125.6(2) . . ?
O2 C2 N1 123.8(3) . . ?
O2 C2 N3 121.0(3) . . ?
N1 C2 N3 115.2(3) . . ?
C4 N3 C2 127.3(3) . . ?
C4 N3 H3 118(2) . . ?
C2 N3 H3 115(2) . . ?
O4 C4 N3 119.9(3) . . ?
O4 C4 C5 125.3(3) . . ?
N3 C4 C5 114.8(3) . . ?
C6 C5 C4 116.8(3) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C5 C6 N1 126.8(3) . . ?
C5 C6 N7 125.7(3) . . ?
N1 C6 N7 107.5(2) . . ?
C11 N7 C8 111.9(2) . . ?
C11 N7 C6 112.6(2) . . ?
C8 N7 C6 135.5(2) . . ?
C9 C8 N7 105.3(3) . . ?
C9 C8 H8 127.3 . . ?
N7 C8 H8 127.3 . . ?
C8 C9 N10 107.4(3) . . ?
C8 C9 H9 126.3 . . ?
N10 C9 H9 126.3 . . ?
C11 N10 C9 110.6(2) . . ?
C11 N10 C12 124.9(2) . . ?
C9 N10 C12 124.5(2) . . ?
N10 C11 N7 104.8(2) . . ?
N10 C11 B1 142.8(3) . . ?
N7 C11 B1 112.5(2) . . ?
N10 C12 C13 111.2(2) . . ?
N10 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N10 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C18 C13 C14 119.4(3) . . ?
C18 C13 C12 120.7(3) . . ?
C14 C13 C12 119.9(3) . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 119.6(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C13 C18 C17 120.5(3) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 B1 115.9(3) . . ?
C20 C19 H19A 108.3 . . ?
B1 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
B1 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 B1 115.6(3) . . ?
C22 C21 H21A 108.4 . . ?
B1 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
B1 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21A B1A C19A 116.2(3) . . ?
C21A B1A N1A 111.7(3) . . ?
C19A B1A N1A 111.0(3) . . ?
C21A B1A C11A 112.5(3) . . ?
C19A B1A C11A 111.1(3) . . ?
N1A B1A C11A 91.8(2) . . ?
C6A N1A C2A 118.5(3) . . ?
C6A N1A B1A 116.3(2) . . ?
C2A N1A B1A 125.2(2) . . ?
O2A C2A N1A 122.7(3) . . ?
O2A C2A N3A 121.4(3) . . ?
N1A C2A N3A 115.9(3) . . ?
C4A N3A C2A 126.8(3) . . ?
C4A N3A H3A 119(2) . . ?
C2A N3A H3A 115(2) . . ?
O4A C4A N3A 119.5(3) . . ?
O4A C4A C5A 125.7(3) . . ?
N3A C4A C5A 114.8(3) . . ?
C6A C5A C4A 117.4(3) . . ?
C6A C5A H5A 121.3 . . ?
C4A C5A H5A 121.3 . . ?
C5A C6A N1A 126.6(3) . . ?
C5A C6A N7A 126.6(3) . . ?
N1A C6A N7A 106.8(3) . . ?
C11A N7A C8A 111.3(2) . . ?
C11A N7A C6A 112.7(2) . . ?
C8A N7A C6A 136.0(2) . . ?
C9A C8A N7A 105.4(3) . . ?
C9A C8A H8A 127.3 . . ?
N7A C8A H8A 127.3 . . ?
C8A C9A N10A 107.5(3) . . ?
C8A C9A H9A 126.3 . . ?
N10A C9A H9A 126.3 . . ?
C11A N10A C9A 110.4(2) . . ?
C11A N10A C12A 125.0(2) . . ?
C9A N10A C12A 124.6(2) . . ?
N10A C11A N7A 105.4(2) . . ?
N10A C11A B1A 142.1(3) . . ?
N7A C11A B1A 112.5(2) . . ?
N10A C12A C13A 112.0(2) . . ?
N10A C12A H12C 109.2 . . ?
C13A C12A H12C 109.2 . . ?
N10A C12A H12D 109.2 . . ?
C13A C12A H12D 109.2 . . ?
H12C C12A H12D 107.9 . . ?
C14A C13A C18A 119.0(3) . . ?
C14A C13A C12A 120.4(3) . . ?
C18A C13A C12A 120.5(3) . . ?
C13A C14A C15A 120.2(3) . . ?
C13A C14A H14A 119.9 . . ?
C15A C14A H14A 119.9 . . ?
C16A C15A C14A 119.6(4) . . ?
C16A C15A H15A 120.2 . . ?
C14A C15A H15A 120.2 . . ?
C17A C16A C15A 120.6(4) . . ?
C17A C16A H16A 119.7 . . ?
C15A C16A H16A 119.7 . . ?
C16A C17A C18A 120.3(4) . . ?
C16A C17A H17A 119.8 . . ?
C18A C17A H17A 119.8 . . ?
C17A C18A C13A 120.3(4) . . ?
C17A C18A H18A 119.8 . . ?
C13A C18A H18A 119.8 . . ?
C20A C19A B1A 115.7(3) . . ?
C20A C19A H19C 108.4 . . ?
B1A C19A H19C 108.4 . . ?
C20A C19A H19D 108.4 . . ?
B1A C19A H19D 108.4 . . ?
H19C C19A H19D 107.4 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C22A C21A B1A 116.0(3) . . ?
C22A C21A H21C 108.3 . . ?
B1A C21A H21C 108.3 . . ?
C22A C21A H21D 108.3 . . ?
B1A C21A H21D 108.3 . . ?
H21C C21A H21D 107.4 . . ?
C21A C22A H22D 109.5 . . ?
C21A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
C21A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 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
C11 B1 N1 C6 -1.2(3) . . . . ?
C19 B1 N1 C6 -117.4(3) . . . . ?
C21 B1 N1 C6 114.2(3) . . . . ?
C11 B1 N1 C2 -179.9(3) . . . . ?
C19 B1 N1 C2 64.0(4) . . . . ?
C21 B1 N1 C2 -64.4(4) . . . . ?
C6 N1 C2 O2 179.4(3) . . . . ?
B1 N1 C2 O2 -2.0(5) . . . . ?
C6 N1 C2 N3 -0.1(4) . . . . ?
B1 N1 C2 N3 178.5(3) . . . . ?
O2 C2 N3 C4 -179.5(3) . . . . ?
N1 C2 N3 C4 0.0(4) . . . . ?
C2 N3 C4 O4 179.7(3) . . . . ?
C2 N3 C4 C5 -0.2(4) . . . . ?
O4 C4 C5 C6 -179.4(3) . . . . ?
N3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 N1 -0.7(4) . . . . ?
C4 C5 C6 N7 179.2(3) . . . . ?
C2 N1 C6 C5 0.5(5) . . . . ?
B1 N1 C6 C5 -178.2(3) . . . . ?
C2 N1 C6 N7 -179.4(2) . . . . ?
B1 N1 C6 N7 1.8(3) . . . . ?
C5 C6 N7 C11 178.4(3) . . . . ?
N1 C6 N7 C11 -1.6(3) . . . . ?
C5 C6 N7 C8 -0.4(5) . . . . ?
N1 C6 N7 C8 179.6(3) . . . . ?
C11 N7 C8 C9 -0.1(3) . . . . ?
C6 N7 C8 C9 178.7(3) . . . . ?
N7 C8 C9 N10 -0.2(3) . . . . ?
C8 C9 N10 C11 0.4(3) . . . . ?
C8 C9 N10 C12 -179.6(3) . . . . ?
C9 N10 C11 N7 -0.4(3) . . . . ?
C12 N10 C11 N7 179.6(3) . . . . ?
C9 N10 C11 B1 -179.8(4) . . . . ?
C12 N10 C11 B1 0.2(6) . . . . ?
C8 N7 C11 N10 0.3(3) . . . . ?
C6 N7 C11 N10 -178.7(2) . . . . ?
C8 N7 C11 B1 179.9(2) . . . . ?
C6 N7 C11 B1 0.8(3) . . . . ?
C19 B1 C11 N10 -66.4(5) . . . . ?
C21 B1 C11 N10 65.7(5) . . . . ?
N1 B1 C11 N10 179.5(4) . . . . ?
C19 B1 C11 N7 114.3(3) . . . . ?
C21 B1 C11 N7 -113.7(3) . . . . ?
N1 B1 C11 N7 0.2(3) . . . . ?
C11 N10 C12 C13 115.3(3) . . . . ?
C9 N10 C12 C13 -64.7(4) . . . . ?
N10 C12 C13 C18 86.7(4) . . . . ?
N10 C12 C13 C14 -92.0(3) . . . . ?
C18 C13 C14 C15 -0.2(5) . . . . ?
C12 C13 C14 C15 178.5(3) . . . . ?
C13 C14 C15 C16 -1.0(5) . . . . ?
C14 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
C14 C13 C18 C17 1.5(5) . . . . ?
C12 C13 C18 C17 -177.2(3) . . . . ?
C16 C17 C18 C13 -1.6(5) . . . . ?
C11 B1 C19 C20 -46.6(4) . . . . ?
C21 B1 C19 C20 -177.9(3) . . . . ?
N1 B1 C19 C20 55.6(4) . . . . ?
C11 B1 C21 C22 49.2(4) . . . . ?
C19 B1 C21 C22 -179.2(3) . . . . ?
N1 B1 C21 C22 -52.7(4) . . . . ?
C21A B1A N1A C6A -114.6(3) . . . . ?
C19A B1A N1A C6A 113.9(3) . . . . ?
C11A B1A N1A C6A 0.5(3) . . . . ?
C21A B1A N1A C2A 67.4(4) . . . . ?
C19A B1A N1A C2A -64.1(4) . . . . ?
C11A B1A N1A C2A -177.5(3) . . . . ?
C6A N1A C2A O2A 180.0(3) . . . . ?
B1A N1A C2A O2A -2.0(5) . . . . ?
C6A N1A C2A N3A -0.5(4) . . . . ?
B1A N1A C2A N3A 177.4(3) . . . . ?
O2A C2A N3A C4A -176.8(3) . . . . ?
N1A C2A N3A C4A 3.7(4) . . . . ?
C2A N3A C4A O4A 177.2(3) . . . . ?
C2A N3A C4A C5A -3.9(4) . . . . ?
O4A C4A C5A C6A 179.8(3) . . . . ?
N3A C4A C5A C6A 1.0(4) . . . . ?
C4A C5A C6A N1A 1.9(4) . . . . ?
C4A C5A C6A N7A -177.1(3) . . . . ?
C2A N1A C6A C5A -2.2(4) . . . . ?
B1A N1A C6A C5A 179.6(3) . . . . ?
C2A N1A C6A N7A 177.0(2) . . . . ?
B1A N1A C6A N7A -1.2(3) . . . . ?
C5A C6A N7A C11A -179.5(3) . . . . ?
N1A C6A N7A C11A 1.3(3) . . . . ?
C5A C6A N7A C8A 2.9(5) . . . . ?
N1A C6A N7A C8A -176.3(3) . . . . ?
C11A N7A C8A C9A 0.8(3) . . . . ?
C6A N7A C8A C9A 178.4(3) . . . . ?
N7A C8A C9A N10A -0.4(3) . . . . ?
C8A C9A N10A C11A 0.0(4) . . . . ?
C8A C9A N10A C12A 179.2(3) . . . . ?
C9A N10A C11A N7A 0.5(3) . . . . ?
C12A N10A C11A N7A -178.8(3) . . . . ?
C9A N10A C11A B1A -176.5(4) . . . . ?
C12A N10A C11A B1A 4.3(6) . . . . ?
C8A N7A C11A N10A -0.8(3) . . . . ?
C6A N7A C11A N10A -179.0(2) . . . . ?
C8A N7A C11A B1A 177.2(2) . . . . ?
C6A N7A C11A B1A -1.0(3) . . . . ?
C21A B1A C11A N10A -68.5(5) . . . . ?
C19A B1A C11A N10A 63.8(5) . . . . ?
N1A B1A C11A N10A 177.1(4) . . . . ?
C21A B1A C11A N7A 114.7(3) . . . . ?
C19A B1A C11A N7A -113.0(3) . . . . ?
N1A B1A C11A N7A 0.3(3) . . . . ?
C11A N10A C12A C13A -122.0(3) . . . . ?
C9A N10A C12A C13A 58.8(4) . . . . ?
N10A C12A C13A C14A -91.7(3) . . . . ?
N10A C12A C13A C18A 87.3(4) . . . . ?
C18A C13A C14A C15A -0.2(5) . . . . ?
C12A C13A C14A C15A 178.9(3) . . . . ?
C13A C14A C15A C16A 1.0(5) . . . . ?
C14A C15A C16A C17A -1.2(6) . . . . ?
C15A C16A C17A C18A 0.6(6) . . . . ?
C16A C17A C18A C13A 0.2(6) . . . . ?
C14A C13A C18A C17A -0.4(5) . . . . ?
C12A C13A C18A C17A -179.5(3) . . . . ?
C21A B1A C19A C20A -177.5(3) . . . . ?
N1A B1A C19A C20A -48.3(4) . . . . ?
C11A B1A C19A C20A 52.2(4) . . . . ?
C19A B1A C21A C22A -178.9(3) . . . . ?
N1A B1A C21A C22A 52.3(4) . . . . ?
C11A B1A C21A C22A -49.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O4A 0.86(2) 2.05(2) 2.899(4) 169(3) 1_545
C8 H8 O4A 0.95 2.64 3.560(4) 163.5 .
C9 H9 O2 0.95 2.22 2.815(4) 119.7 1_565
N3A H3A O4 0.87(2) 2.06(2) 2.917(3) 169(3) 1_565
C8A H8A O4 0.95 2.55 3.469(4) 161.4 .
C9A H9A O2A 0.95 2.14 2.769(4) 122.1 1_545

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 976126'
