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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_schm63_compound_3b

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
4-(2-hydroxyl-5-methylphenyl)-1-phenyl-4H-1,2,4-triazol-1-iumperchlorate
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N3 O, Cl O4'
_chemical_formula_sum            'C15 H14 Cl N3 O5'
_chemical_formula_weight         351.74

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.0904(5)
_cell_length_b                   7.6950(5)
_cell_length_c                   16.3916(13)
_cell_angle_alpha                83.899(6)
_cell_angle_beta                 82.995(7)
_cell_angle_gamma                87.213(6)
_cell_volume                     757.65(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3383
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      29.6

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.285
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 dx = 46 mm, 1 deg., 2 x 2.5 sec., 5 sets, 363 frames
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  
'Agilent, SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'rotation in ω, 1°'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            5946
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         29.880
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3750
_reflns_number_gt                3257
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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)+(0.0538P)²+0.1867P]
 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     SHELXL
_refine_ls_extinction_coef       0.082(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3750
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Cl1 Cl 0.89545(6) 0.85427(4) 0.76386(2) 0.02794(13) Uani 1 1 d . . . . .
O1 O 0.9323(2) 0.96709(16) 0.82586(8) 0.0419(3) Uani 1 1 d . . . . .
O2 O 1.0286(2) 0.69679(17) 0.77530(9) 0.0490(4) Uani 1 1 d . . . . .
O3 O 0.6681(2) 0.81276(19) 0.77403(9) 0.0490(4) Uani 1 1 d . . . . .
O4 O 0.9566(3) 0.9420(2) 0.68387(8) 0.0554(4) Uani 1 1 d . . . . .
N1 N 0.6133(2) 0.55956(14) 0.63317(7) 0.0210(2) Uani 1 1 d . . . . .
N2 N 0.8205(2) 0.48317(17) 0.63528(8) 0.0292(3) Uani 1 1 d . . . . .
C3 C 0.8114(3) 0.3976(2) 0.70833(9) 0.0285(3) Uani 1 1 d . . . . .
H3 H 0.9319 0.3304 0.7286 0.034 Uiso 1 1 calc R U . . .
N4 N 0.6085(2) 0.41586(14) 0.75217(7) 0.0222(3) Uani 1 1 d . . . . .
C5 C 0.4870(3) 0.51965(17) 0.70332(8) 0.0236(3) Uani 1 1 d . . . . .
H5 H 0.3374 0.5578 0.7166 0.028 Uiso 1 1 calc R U . . .
C6 C 0.5432(2) 0.34196(17) 0.83554(8) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.3568(3) 0.24108(17) 0.85150(8) 0.0240(3) Uani 1 1 d . . . . .
O7 O 0.2436(2) 0.21535(14) 0.78714(6) 0.0301(3) Uani 1 1 d D . . . .
H7 H 0.164(3) 0.130(2) 0.8003(13) 0.045 Uiso 1 1 d D U . . .
C8 C 0.2945(3) 0.17314(18) 0.93243(9) 0.0274(3) Uani 1 1 d . . . . .
H8 H 0.1652 0.1067 0.9455 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4209(3) 0.20218(18) 0.99424(9) 0.0281(3) Uani 1 1 d . . . . .
H9 H 0.3757 0.1551 1.0493 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6120(3) 0.29827(18) 0.97795(9) 0.0264(3) Uani 1 1 d . . . . .
C11 C 0.6711(3) 0.36976(18) 0.89711(9) 0.0247(3) Uani 1 1 d . . . . .
H11 H 0.7992 0.4377 0.8841 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7500(3) 0.3241(2) 1.04566(9) 0.0325(4) Uani 1 1 d . . . . .
H12A H 0.6670 0.2886 1.0994 0.049 Uiso 1 1 calc R U . . .
H12B H 0.7851 0.4477 1.0427 0.049 Uiso 1 1 calc R U . . .
H12C H 0.8875 0.2529 1.0389 0.049 Uiso 1 1 calc R U . . .
C13 C 0.5587(2) 0.66468(16) 0.55980(8) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.7236(3) 0.68910(18) 0.49409(9) 0.0277(3) Uani 1 1 d . . . . .
H14 H 0.8683 0.6392 0.4977 0.033 Uiso 1 1 calc R U . . .
C15 C 0.6721(3) 0.7884(2) 0.42275(9) 0.0329(4) Uani 1 1 d . . . . .
H15 H 0.7831 0.8074 0.3771 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4614(3) 0.85979(19) 0.41738(9) 0.0327(4) Uani 1 1 d . . . . .
H16 H 0.4277 0.9269 0.3681 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2998(3) 0.83337(19) 0.48376(10) 0.0323(3) Uani 1 1 d . . . . .
H17 H 0.1550 0.8830 0.4800 0.039 Uiso 1 1 calc R U . . .
C18 C 0.3472(3) 0.73464(19) 0.55619(9) 0.0285(3) Uani 1 1 d . . . . .
H18 H 0.2364 0.7160 0.6020 0.034 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
Cl1 O3 1.4218(13) . ?
Cl1 O4 1.4250(13) . ?
Cl1 O2 1.4333(13) . ?
Cl1 O1 1.4487(12) . ?
N1 C5 1.3194(18) . ?
N1 N2 1.3683(17) . ?
N1 C13 1.4410(17) . ?
N2 C3 1.3001(19) . ?
C3 N4 1.3610(19) . ?
C3 H3 0.9500 . ?
N4 C5 1.3332(18) . ?
N4 C6 1.4399(17) . ?
C5 H5 0.9500 . ?
C6 C11 1.388(2) . ?
C6 C7 1.389(2) . ?
C7 O7 1.3651(17) . ?
C7 C8 1.388(2) . ?
O7 H7 0.830(15) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(2) . ?
C10 C12 1.506(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.377(2) . ?
C13 C14 1.384(2) . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
O3 Cl1 O4 110.69(9) . . ?
O3 Cl1 O2 109.44(9) . . ?
O4 Cl1 O2 109.92(9) . . ?
O3 Cl1 O1 108.88(8) . . ?
O4 Cl1 O1 109.16(9) . . ?
O2 Cl1 O1 108.72(8) . . ?
C5 N1 N2 110.99(11) . . ?
C5 N1 C13 128.99(12) . . ?
N2 N1 C13 120.01(11) . . ?
C3 N2 N1 103.89(12) . . ?
N2 C3 N4 111.80(13) . . ?
N2 C3 H3 124.1 . . ?
N4 C3 H3 124.1 . . ?
C5 N4 C3 106.11(12) . . ?
C5 N4 C6 127.52(12) . . ?
C3 N4 C6 126.34(12) . . ?
N1 C5 N4 107.20(13) . . ?
N1 C5 H5 126.4 . . ?
N4 C5 H5 126.4 . . ?
C11 C6 C7 121.95(13) . . ?
C11 C6 N4 119.14(13) . . ?
C7 C6 N4 118.89(12) . . ?
O7 C7 C8 123.49(14) . . ?
O7 C7 C6 118.44(12) . . ?
C8 C7 C6 118.07(13) . . ?
C7 O7 H7 109.5(15) . . ?
C9 C8 C7 120.07(14) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.97(13) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C11 C10 C9 117.83(14) . . ?
C11 C10 C12 121.11(15) . . ?
C9 C10 C12 121.06(14) . . ?
C6 C11 C10 120.05(14) . . ?
C6 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.18(13) . . ?
C18 C13 N1 120.04(13) . . ?
C14 C13 N1 117.78(13) . . ?
C13 C14 C15 118.27(15) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C16 C15 C14 120.78(15) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.83(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.58(16) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 118.37(15) . . ?
C13 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?

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
C5 N1 N2 C3 0.11(16) . . . . ?
C13 N1 N2 C3 -178.91(12) . . . . ?
N1 N2 C3 N4 0.23(17) . . . . ?
N2 C3 N4 C5 -0.47(17) . . . . ?
N2 C3 N4 C6 -178.55(13) . . . . ?
N2 N1 C5 N4 -0.40(16) . . . . ?
C13 N1 C5 N4 178.51(12) . . . . ?
C3 N4 C5 N1 0.51(15) . . . . ?
C6 N4 C5 N1 178.56(12) . . . . ?
C5 N4 C6 C11 -125.40(15) . . . . ?
C3 N4 C6 C11 52.28(19) . . . . ?
C5 N4 C6 C7 56.24(19) . . . . ?
C3 N4 C6 C7 -126.08(16) . . . . ?
C11 C6 C7 O7 -177.97(12) . . . . ?
N4 C6 C7 O7 0.34(19) . . . . ?
C11 C6 C7 C8 2.6(2) . . . . ?
N4 C6 C7 C8 -179.05(12) . . . . ?
O7 C7 C8 C9 178.71(13) . . . . ?
C6 C7 C8 C9 -1.9(2) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 1.7(2) . . . . ?
C8 C9 C10 C12 -178.36(13) . . . . ?
C7 C6 C11 C10 -1.2(2) . . . . ?
N4 C6 C11 C10 -179.46(12) . . . . ?
C9 C10 C11 C6 -1.0(2) . . . . ?
C12 C10 C11 C6 179.04(13) . . . . ?
C5 N1 C13 C18 -2.0(2) . . . . ?
N2 N1 C13 C18 176.87(13) . . . . ?
C5 N1 C13 C14 179.11(14) . . . . ?
N2 N1 C13 C14 -2.07(18) . . . . ?
C18 C13 C14 C15 0.3(2) . . . . ?
N1 C13 C14 C15 179.24(13) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C14 C13 C18 C17 -0.2(2) . . . . ?
N1 C13 C18 C17 -179.06(13) . . . . ?
C16 C17 C18 C13 0.1(2) . . . . ?

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
C3 H3 O7 0.95 2.33 3.2629(19) 169.1 1_655
C5 H5 O2 0.95 2.28 3.196(2) 162.1 1_455
O7 H7 O1 0.830(15) 1.911(16) 2.7289(17) 168(2) 1_445

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.057


_shelxl_version_number           2013-2


_database_code_depnum_ccdc_archive 'CCDC 1027080'
#######################################################################
#
#                 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_schm68_m_compound_4b

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 4-methyl-2-(1-phenyl-4H-1,2,4-triazol-1-ium-4-yl)phenolate hydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N3 O, H2 O'
_chemical_formula_sum            'C15 H15 N3 O2'
_chemical_formula_weight         269.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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                   19.9626(9)
_cell_length_b                   4.6037(2)
_cell_length_c                   15.3349(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.829(5)
_cell_angle_gamma                90
_cell_volume                     1298.91(11)
_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            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9206
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 dx = 40 mm, 20 sec./deg., 2 deg., 6 sets, 268 frames
;

_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, 2°'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            7555
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.882
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2901
_reflns_number_gt                2770
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.985

_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)+(0.0381P)²+0.4096P]
 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 1299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
 Determination of absolute structure using Bayesian statistics 
 on Bijvoet differences (Hooft, Straver and Spek, 2008): 
 Hooft's y = -0.1(4) (Platon: Spek, 2009).
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2901
_refine_ls_number_parameters     188
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_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
N1 N 0.43111(8) 0.6646(3) 0.65953(10) 0.0159(3) Uani 1 1 d . . . . .
N2 N 0.41083(9) 0.6116(4) 0.73392(11) 0.0215(4) Uani 1 1 d . . . . .
C3 C 0.45667(11) 0.4130(4) 0.78303(14) 0.0211(4) Uani 1 1 d . . . . .
H3 H 0.4566 0.3300 0.8397 0.025 Uiso 1 1 calc R U . . .
N4 N 0.50506(8) 0.3385(3) 0.74278(11) 0.0150(3) Uani 1 1 d . . . . .
C5 C 0.48730(10) 0.5020(4) 0.66483(13) 0.0158(4) Uani 1 1 d . . . . .
H5 H 0.5107 0.5015 0.6214 0.019 Uiso 1 1 calc R U . . .
C6 C 0.39351(10) 0.8748(4) 0.58817(13) 0.0166(4) Uani 1 1 d . . . . .
C7 C 0.33206(10) 1.0092(4) 0.59062(14) 0.0202(4) Uani 1 1 d . . . . .
H7 H 0.3149 0.9631 0.6387 0.024 Uiso 1 1 calc R U . . .
C8 C 0.29625(11) 1.2122(5) 0.52139(15) 0.0236(4) Uani 1 1 d . . . . .
H8 H 0.2542 1.3069 0.5222 0.028 Uiso 1 1 calc R U . . .
C9 C 0.32128(11) 1.2783(4) 0.45097(14) 0.0223(4) Uani 1 1 d . . . . .
H9 H 0.2964 1.4178 0.4039 0.027 Uiso 1 1 calc R U . . .
C10 C 0.38268(11) 1.1401(4) 0.44944(14) 0.0215(4) Uani 1 1 d . . . . .
H10 H 0.3995 1.1836 0.4008 0.026 Uiso 1 1 calc R U . . .
C11 C 0.41954(10) 0.9384(4) 0.51884(14) 0.0197(4) Uani 1 1 d . . . . .
H11 H 0.4620 0.8455 0.5187 0.024 Uiso 1 1 calc R U . . .
C12 C 0.56308(10) 0.1264(4) 0.77436(13) 0.0157(4) Uani 1 1 d . . . . .
C13 C 0.59977(10) 0.0709(4) 0.71511(13) 0.0176(4) Uani 1 1 d . . . . .
H13 H 0.5859 0.1709 0.6565 0.021 Uiso 1 1 calc R U . . .
C14 C 0.65616(10) -0.1283(4) 0.74066(15) 0.0208(4) Uani 1 1 d . . . . .
C15 C 0.67419(10) -0.2706(4) 0.82703(14) 0.0209(4) Uani 1 1 d . . . . .
H15 H 0.7121 -0.4107 0.8456 0.025 Uiso 1 1 calc R U . . .
C16 C 0.63854(10) -0.2138(4) 0.88640(13) 0.0198(4) Uani 1 1 d . . . . .
H16 H 0.6533 -0.3144 0.9450 0.024 Uiso 1 1 calc R U . . .
C17 C 0.58055(10) -0.0104(4) 0.86315(13) 0.0163(4) Uani 1 1 d . . . . .
O18 O 0.54676(7) 0.0393(3) 0.91935(9) 0.0204(3) Uani 1 1 d . . . . .
C19 C 0.69699(12) -0.1858(5) 0.67759(15) 0.0282(5) Uani 1 1 d . . . . .
H19A H 0.6733 -0.0826 0.6175 0.042 Uiso 1 1 calc R U . . .
H19B H 0.6970 -0.3948 0.6655 0.042 Uiso 1 1 calc R U . . .
H19C H 0.7472 -0.1173 0.7089 0.042 Uiso 1 1 calc R U . . .
O1W O 0.54899(9) 0.4593(3) 0.51717(10) 0.0235(3) Uani 1 1 d D . . . .
H1W1 H 0.5473(15) 0.301(4) 0.4871(19) 0.035 Uiso 1 1 d D U . . .
H1W2 H 0.5575(15) 0.605(4) 0.4893(19) 0.035 Uiso 1 1 d D 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
N1 C5 1.325(2) . ?
N1 N2 1.372(2) . ?
N1 C6 1.435(2) . ?
N2 C3 1.306(3) . ?
C3 N4 1.376(2) . ?
C3 H3 0.9500 . ?
N4 C5 1.339(2) . ?
N4 C12 1.447(2) . ?
C5 H5 0.9500 . ?
C6 C11 1.384(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.394(3) . ?
C12 C17 1.416(3) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(3) . ?
C14 C19 1.510(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.423(3) . ?
C16 H16 0.9500 . ?
C17 O18 1.304(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O1W H1W1 0.85(2) . ?
O1W H1W2 0.85(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 111.36(15) . . ?
C5 N1 C6 127.42(16) . . ?
N2 N1 C6 121.22(15) . . ?
C3 N2 N1 103.74(15) . . ?
N2 C3 N4 111.87(17) . . ?
N2 C3 H3 124.1 . . ?
N4 C3 H3 124.1 . . ?
C5 N4 C3 105.75(15) . . ?
C5 N4 C12 125.34(15) . . ?
C3 N4 C12 128.91(16) . . ?
N1 C5 N4 107.29(16) . . ?
N1 C5 H5 126.4 . . ?
N4 C5 H5 126.4 . . ?
C11 C6 C7 121.73(18) . . ?
C11 C6 N1 119.16(16) . . ?
C7 C6 N1 119.10(16) . . ?
C8 C7 C6 118.59(19) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C9 120.59(19) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 119.94(19) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.12(19) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C6 C11 C10 119.02(18) . . ?
C6 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C13 C12 C17 123.34(17) . . ?
C13 C12 N4 117.40(17) . . ?
C17 C12 N4 119.25(16) . . ?
C14 C13 C12 120.77(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 117.50(18) . . ?
C13 C14 C19 121.05(19) . . ?
C15 C14 C19 121.44(18) . . ?
C16 C15 C14 121.90(18) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 122.47(17) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
O18 C17 C12 124.04(17) . . ?
O18 C17 C16 121.94(16) . . ?
C12 C17 C16 114.01(16) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H1W1 O1W H1W2 112(2) . . ?

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
C5 N1 N2 C3 0.0(2) . . . . ?
C6 N1 N2 C3 -179.73(16) . . . . ?
N1 N2 C3 N4 0.0(2) . . . . ?
N2 C3 N4 C5 0.0(2) . . . . ?
N2 C3 N4 C12 -179.06(17) . . . . ?
N2 N1 C5 N4 0.1(2) . . . . ?
C6 N1 C5 N4 179.72(15) . . . . ?
C3 N4 C5 N1 0.0(2) . . . . ?
C12 N4 C5 N1 179.08(15) . . . . ?
C5 N1 C6 C11 -4.9(3) . . . . ?
N2 N1 C6 C11 174.70(18) . . . . ?
C5 N1 C6 C7 175.18(19) . . . . ?
N2 N1 C6 C7 -5.2(2) . . . . ?
C11 C6 C7 C8 0.0(3) . . . . ?
N1 C6 C7 C8 179.90(17) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C7 C6 C11 C10 -0.6(3) . . . . ?
N1 C6 C11 C10 179.47(17) . . . . ?
C9 C10 C11 C6 1.0(3) . . . . ?
C5 N4 C12 C13 -5.4(3) . . . . ?
C3 N4 C12 C13 173.52(18) . . . . ?
C5 N4 C12 C17 173.72(18) . . . . ?
C3 N4 C12 C17 -7.4(3) . . . . ?
C17 C12 C13 C14 0.6(3) . . . . ?
N4 C12 C13 C14 179.72(17) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C12 C13 C14 C19 -178.95(19) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C19 C14 C15 C16 178.19(19) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C13 C12 C17 O18 179.98(17) . . . . ?
N4 C12 C17 O18 0.9(3) . . . . ?
C13 C12 C17 C16 -0.8(3) . . . . ?
N4 C12 C17 C16 -179.88(16) . . . . ?
C15 C16 C17 O18 179.28(18) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?

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
C3 H3 O18 0.95 2.19 2.765(2) 117.6 .
C5 H5 O1W 0.95 2.03 2.974(2) 171.6 .
C11 H11 O1W 0.95 2.49 3.405(2) 161.2 .
C13 H13 O1W 0.95 2.38 3.324(2) 174.6 .
O1W H1W1 O18 0.85(2) 1.88(2) 2.733(2) 177(3) 2_554
O1W H1W2 O18 0.85(2) 1.92(2) 2.744(2) 163(3) 2_564

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.035


_shelxl_version_number           2013-2


_database_code_depnum_ccdc_archive 'CCDC 1027081'
#######################################################################
#
#                 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_schm67_compound_15c

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (4-methyl-2-(1-phenyl-4H-1,2,4-triazol-1-ium-4-yl)phenoxy)tris(perfluorophenyl)borate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H13 B F15 N3 O'
_chemical_formula_sum            'C33 H13 B F15 N3 O'
_chemical_formula_weight         763.27

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   11.777(1)
_cell_length_b                   12.266(1)
_cell_length_c                   12.551(1)
_cell_angle_alpha                76.40(1)
_cell_angle_beta                 64.72(1)
_cell_angle_gamma                64.59(1)
_cell_volume                     1477.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    127
_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    1.715
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8647
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 dx = 40 mm, 20 sec./deg., 2 deg., 6 sets, 254 Frames
;

_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, 2°'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            17419
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.655
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6759
_reflns_number_gt                5594
_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          
;
 Phenyl group disordered, disordered atoms refined isotropically, use of
constraints (EADP) and restaints (SADI) in the refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0371P)²+1.0253P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6759
_refine_ls_number_parameters     474
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.104
_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
N1 N 0.20002(13) -0.04448(12) 0.22206(11) 0.0189(3) Uani 1 1 d . . . . .
N2 N 0.10479(13) 0.00108(13) 0.17108(12) 0.0231(3) Uani 1 1 d . . . . .
C3 C 0.14957(15) 0.07218(14) 0.08365(14) 0.0202(3) Uani 1 1 d . . . . .
H3 H 0.1051 0.1181 0.0306 0.024 Uiso 1 1 calc R U . . .
N4 N 0.26854(12) 0.07297(11) 0.07702(11) 0.0157(2) Uani 1 1 d . . . . .
C5 C 0.29759(15) -0.00228(13) 0.16604(13) 0.0179(3) Uani 1 1 d . . . . .
H5 H 0.3742 -0.0216 0.1852 0.021 Uiso 1 1 calc R U . . .
C6 C 0.18353(16) -0.12385(15) 0.32706(14) 0.0233(3) Uani 1 1 d D . . . .
C7 C 0.1792(4) -0.2331(3) 0.3300(3) 0.0286(9) Uiso 0.649(5) 1 d D . P A 1
H7 H 0.1890 -0.2607 0.2608 0.034 Uiso 0.649(5) 1 calc R U P A 1
C8 C 0.1602(4) -0.3045(3) 0.4353(3) 0.0292(9) Uiso 0.649(5) 1 d D . P A 1
H8 H 0.1579 -0.3815 0.4375 0.035 Uiso 0.649(5) 1 calc R U P A 1
C9 C 0.1448(3) -0.2647(3) 0.5361(3) 0.0252(5) Uiso 0.649(5) 1 d D . P A 1
H9 H 0.1327 -0.3147 0.6073 0.030 Uiso 0.649(5) 1 calc R U P A 1
C10 C 0.1468(4) -0.1531(3) 0.5345(3) 0.0343(8) Uiso 0.649(5) 1 d D . P A 1
H10 H 0.1367 -0.1267 0.6045 0.041 Uiso 0.649(5) 1 calc R U P A 1
C11 C 0.1634(4) -0.0787(3) 0.4314(2) 0.0275(7) Uiso 0.649(5) 1 d D . P A 1
H11 H 0.1615 -0.0003 0.4303 0.033 Uiso 0.649(5) 1 calc R U P A 1
C7' C 0.1499(6) -0.2203(4) 0.3240(4) 0.0173(13) Uiso 0.351(5) 1 d D . P A 2
H7' H 0.1312 -0.2260 0.2594 0.021 Uiso 0.351(5) 1 calc R U P A 2
C8' C 0.1450(6) -0.3058(5) 0.4174(5) 0.0238(15) Uiso 0.351(5) 1 d D . P A 2
H8' H 0.1203 -0.3706 0.4190 0.029 Uiso 0.351(5) 1 calc R U P A 2
C9' C 0.1761(6) -0.2973(5) 0.5087(5) 0.0252(5) Uiso 0.351(5) 1 d D . P A 2
H9' H 0.1760 -0.3580 0.5717 0.030 Uiso 0.351(5) 1 calc R U P A 2
C10' C 0.2079(7) -0.1994(5) 0.5088(5) 0.0371(15) Uiso 0.351(5) 1 d D . P A 2
H10' H 0.2207 -0.1892 0.5750 0.045 Uiso 0.351(5) 1 calc R U P A 2
C11' C 0.2206(7) -0.1176(5) 0.4108(4) 0.0290(13) Uiso 0.351(5) 1 d D . P A 2
H11' H 0.2553 -0.0581 0.4040 0.035 Uiso 0.351(5) 1 calc R U P A 2
C12 C 0.34203(14) 0.14591(13) -0.00411(13) 0.0157(3) Uani 1 1 d . . . . .
C13 C 0.40000(14) 0.19557(13) 0.03908(13) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.46443(15) 0.27148(13) -0.04000(13) 0.0182(3) Uani 1 1 d . . . . .
H14 H 0.5079 0.3050 -0.0154 0.022 Uiso 1 1 calc R U . . .
C15 C 0.46546(15) 0.29842(14) -0.15414(13) 0.0193(3) Uani 1 1 d . . . . .
H15 H 0.5084 0.3516 -0.2055 0.023 Uiso 1 1 calc R U . . .
C16 C 0.40551(16) 0.25001(13) -0.19589(13) 0.0191(3) Uani 1 1 d . . . . .
C17 C 0.34516(15) 0.17110(13) -0.11913(13) 0.0175(3) Uani 1 1 d . . . . .
H17 H 0.3060 0.1343 -0.1454 0.021 Uiso 1 1 calc R U . . .
C18 C 0.40435(19) 0.28359(16) -0.31913(14) 0.0277(4) Uani 1 1 d . . . . .
H18A H 0.3255 0.3575 -0.3187 0.042 Uiso 1 1 calc R U . . .
H18B H 0.3995 0.2177 -0.3464 0.042 Uiso 1 1 calc R U . . .
H18C H 0.4873 0.2974 -0.3723 0.042 Uiso 1 1 calc R U . . .
O19 O 0.38898(10) 0.16830(9) 0.15240(9) 0.0159(2) Uani 1 1 d . . . . .
B20 B 0.36629(17) 0.25950(15) 0.22836(14) 0.0160(3) Uani 1 1 d . . . . .
C21 C 0.50953(15) 0.26103(13) 0.21820(13) 0.0163(3) Uani 1 1 d . . . . .
C22 C 0.63731(15) 0.18256(13) 0.15571(13) 0.0166(3) Uani 1 1 d . . . . .
F22 F 0.65467(9) 0.10001(8) 0.08932(8) 0.0219(2) Uani 1 1 d . . . . .
C23 C 0.75648(15) 0.18249(14) 0.15215(13) 0.0184(3) Uani 1 1 d . . . . .
F23 F 0.87672(9) 0.10553(9) 0.08564(8) 0.0243(2) Uani 1 1 d . . . . .
C24 C 0.75089(16) 0.26507(15) 0.21324(14) 0.0211(3) Uani 1 1 d . . . . .
F24 F 0.86545(10) 0.27010(10) 0.20660(9) 0.0297(2) Uani 1 1 d . . . . .
C25 C 0.62611(17) 0.34333(14) 0.28067(14) 0.0220(3) Uani 1 1 d . . . . .
F25 F 0.61908(11) 0.42356(9) 0.34229(10) 0.0323(2) Uani 1 1 d . . . . .
C26 C 0.51049(15) 0.33844(14) 0.28272(13) 0.0192(3) Uani 1 1 d . . . . .
F26 F 0.39117(9) 0.41612(9) 0.35202(8) 0.0256(2) Uani 1 1 d . . . . .
C27 C 0.26126(15) 0.38840(14) 0.19187(13) 0.0181(3) Uani 1 1 d . . . . .
C28 C 0.28280(16) 0.49470(14) 0.14491(13) 0.0196(3) Uani 1 1 d . . . . .
F28 F 0.39794(10) 0.50605(9) 0.13000(8) 0.0262(2) Uani 1 1 d . . . . .
C29 C 0.19252(18) 0.59546(14) 0.10681(13) 0.0240(3) Uani 1 1 d . . . . .
F29 F 0.21842(12) 0.69752(9) 0.06720(9) 0.0344(3) Uani 1 1 d . . . . .
C30 C 0.07564(18) 0.59202(15) 0.11149(15) 0.0277(4) Uani 1 1 d . . . . .
F30 F -0.01334(12) 0.68994(10) 0.07587(10) 0.0419(3) Uani 1 1 d . . . . .
C31 C 0.04869(17) 0.48875(16) 0.15633(16) 0.0276(4) Uani 1 1 d . . . . .
F31 F -0.06633(11) 0.48457(11) 0.16319(12) 0.0432(3) Uani 1 1 d . . . . .
C32 C 0.13980(16) 0.39137(14) 0.19564(14) 0.0224(3) Uani 1 1 d . . . . .
F32 F 0.10683(10) 0.29238(9) 0.23946(10) 0.0300(2) Uani 1 1 d . . . . .
C33 C 0.30151(15) 0.21090(14) 0.36678(13) 0.0172(3) Uani 1 1 d . . . . .
C34 C 0.36171(15) 0.09227(14) 0.40485(13) 0.0185(3) Uani 1 1 d . . . . .
F34 F 0.46713(9) 0.01320(8) 0.32533(8) 0.0240(2) Uani 1 1 d . . . . .
C35 C 0.32489(16) 0.04661(14) 0.52072(14) 0.0214(3) Uani 1 1 d . . . . .
F35 F 0.38817(11) -0.07006(9) 0.55001(9) 0.0299(2) Uani 1 1 d . . . . .
C36 C 0.22245(18) 0.12255(16) 0.60760(14) 0.0250(3) Uani 1 1 d . . . . .
F36 F 0.18621(12) 0.08179(10) 0.72122(8) 0.0366(3) Uani 1 1 d . . . . .
C37 C 0.15955(17) 0.24110(16) 0.57542(14) 0.0266(4) Uani 1 1 d . . . . .
F37 F 0.06084(12) 0.31714(10) 0.65916(9) 0.0409(3) Uani 1 1 d . . . . .
C38 C 0.19784(16) 0.28276(14) 0.45811(14) 0.0223(3) Uani 1 1 d . . . . .
F38 F 0.12945(10) 0.40052(9) 0.43599(9) 0.0313(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.3160(19) . ?
N1 N2 1.3734(18) . ?
N1 C6 1.436(2) . ?
N2 C3 1.301(2) . ?
C3 N4 1.3717(19) . ?
C3 H3 0.9500 . ?
N4 C5 1.3372(19) . ?
N4 C12 1.4387(18) . ?
C5 H5 0.9500 . ?
C6 C11' 1.327(4) . ?
C6 C7 1.354(3) . ?
C6 C7' 1.413(4) . ?
C6 C11 1.429(3) . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C7' C8' 1.376(5) . ?
C7' H7' 0.9500 . ?
C8' C9' 1.381(5) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.403(5) . ?
C9' H9' 0.9500 . ?
C10' C11' 1.390(5) . ?
C10' H10' 0.9500 . ?
C11' H11' 0.9500 . ?
C12 C17 1.391(2) . ?
C12 C13 1.400(2) . ?
C13 O19 1.3444(17) . ?
C13 C14 1.399(2) . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(2) . ?
C16 C18 1.509(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O19 B20 1.5030(19) . ?
B20 C27 1.645(2) . ?
B20 C21 1.645(2) . ?
B20 C33 1.651(2) . ?
C21 C22 1.382(2) . ?
C21 C26 1.391(2) . ?
C22 F22 1.3547(17) . ?
C22 C23 1.385(2) . ?
C23 F23 1.3442(17) . ?
C23 C24 1.372(2) . ?
C24 F24 1.3431(17) . ?
C24 C25 1.381(2) . ?
C25 F25 1.3442(18) . ?
C25 C26 1.378(2) . ?
C26 F26 1.3549(17) . ?
C27 C28 1.381(2) . ?
C27 C32 1.396(2) . ?
C28 F28 1.3513(18) . ?
C28 C29 1.384(2) . ?
C29 F29 1.3464(19) . ?
C29 C30 1.371(3) . ?
C30 F30 1.3446(19) . ?
C30 C31 1.371(3) . ?
C31 F31 1.343(2) . ?
C31 C32 1.377(2) . ?
C32 F32 1.3548(19) . ?
C33 C34 1.388(2) . ?
C33 C38 1.392(2) . ?
C34 F34 1.3571(17) . ?
C34 C35 1.380(2) . ?
C35 F35 1.3453(18) . ?
C35 C36 1.379(2) . ?
C36 F36 1.3393(18) . ?
C36 C37 1.372(3) . ?
C37 F37 1.3465(19) . ?
C37 C38 1.382(2) . ?
C38 F38 1.3476(19) . ?

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
C5 N1 N2 111.78(13) . . ?
C5 N1 C6 127.50(13) . . ?
N2 N1 C6 120.66(12) . . ?
C3 N2 N1 103.29(12) . . ?
N2 C3 N4 112.06(13) . . ?
N2 C3 H3 124.0 . . ?
N4 C3 H3 124.0 . . ?
C5 N4 C3 105.85(12) . . ?
C5 N4 C12 127.03(13) . . ?
C3 N4 C12 127.00(13) . . ?
N1 C5 N4 107.02(13) . . ?
N1 C5 H5 126.5 . . ?
N4 C5 H5 126.5 . . ?
C11' C6 C7' 122.9(3) . . ?
C7 C6 C11 121.0(2) . . ?
C11' C6 N1 120.9(2) . . ?
C7 C6 N1 122.36(19) . . ?
C7' C6 N1 115.2(2) . . ?
C11 C6 N1 116.51(16) . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 117.9(2) . . ?
C10 C11 H11 121.0 . . ?
C6 C11 H11 121.0 . . ?
C8' C7' C6 118.0(4) . . ?
C8' C7' H7' 121.0 . . ?
C6 C7' H7' 121.0 . . ?
C7' C8' C9' 119.9(5) . . ?
C7' C8' H8' 120.1 . . ?
C9' C8' H8' 120.1 . . ?
C8' C9' C10' 120.2(4) . . ?
C8' C9' H9' 119.9 . . ?
C10' C9' H9' 119.9 . . ?
C11' C10' C9' 119.3(4) . . ?
C11' C10' H10' 120.3 . . ?
C9' C10' H10' 120.3 . . ?
C6 C11' C10' 119.0(4) . . ?
C6 C11' H11' 120.5 . . ?
C10' C11' H11' 120.5 . . ?
C17 C12 C13 122.58(13) . . ?
C17 C12 N4 119.32(13) . . ?
C13 C12 N4 117.95(13) . . ?
O19 C13 C14 124.95(13) . . ?
O19 C13 C12 118.31(13) . . ?
C14 C13 C12 116.74(13) . . ?
C15 C14 C13 120.69(14) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 122.15(14) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C17 C16 C15 117.58(14) . . ?
C17 C16 C18 121.27(14) . . ?
C15 C16 C18 121.14(14) . . ?
C12 C17 C16 120.19(14) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 O19 B20 122.19(11) . . ?
O19 B20 C27 105.73(12) . . ?
O19 B20 C21 112.06(12) . . ?
C27 B20 C21 115.78(12) . . ?
O19 B20 C33 106.62(12) . . ?
C27 B20 C33 112.84(12) . . ?
C21 B20 C33 103.60(12) . . ?
C22 C21 C26 113.45(13) . . ?
C22 C21 B20 125.33(13) . . ?
C26 C21 B20 121.01(13) . . ?
F22 C22 C21 121.16(13) . . ?
F22 C22 C23 114.48(13) . . ?
C21 C22 C23 124.33(14) . . ?
F23 C23 C24 120.25(14) . . ?
F23 C23 C22 120.31(14) . . ?
C24 C23 C22 119.39(14) . . ?
F24 C24 C23 120.30(14) . . ?
F24 C24 C25 120.59(14) . . ?
C23 C24 C25 119.11(14) . . ?
F25 C25 C26 121.04(15) . . ?
F25 C25 C24 119.77(14) . . ?
C26 C25 C24 119.19(14) . . ?
F26 C26 C25 116.42(13) . . ?
F26 C26 C21 119.18(13) . . ?
C25 C26 C21 124.40(14) . . ?
C28 C27 C32 113.39(14) . . ?
C28 C27 B20 128.06(14) . . ?
C32 C27 B20 118.18(13) . . ?
F28 C28 C27 121.38(14) . . ?
F28 C28 C29 114.87(14) . . ?
C27 C28 C29 123.73(15) . . ?
F29 C29 C30 120.06(15) . . ?
F29 C29 C28 119.92(16) . . ?
C30 C29 C28 120.01(15) . . ?
F30 C30 C31 120.42(17) . . ?
F30 C30 C29 120.39(16) . . ?
C31 C30 C29 119.15(15) . . ?
F31 C31 C30 119.88(16) . . ?
F31 C31 C32 121.10(16) . . ?
C30 C31 C32 119.01(16) . . ?
F32 C32 C31 116.07(15) . . ?
F32 C32 C27 119.24(14) . . ?
C31 C32 C27 124.69(15) . . ?
C34 C33 C38 113.34(14) . . ?
C34 C33 B20 120.43(13) . . ?
C38 C33 B20 125.70(13) . . ?
F34 C34 C35 115.59(13) . . ?
F34 C34 C33 119.53(13) . . ?
C35 C34 C33 124.86(14) . . ?
F35 C35 C36 119.78(14) . . ?
F35 C35 C34 121.04(14) . . ?
C36 C35 C34 119.18(15) . . ?
F36 C36 C37 120.65(15) . . ?
F36 C36 C35 120.71(15) . . ?
C37 C36 C35 118.64(14) . . ?
F37 C37 C36 119.52(15) . . ?
F37 C37 C38 120.09(16) . . ?
C36 C37 C38 120.39(15) . . ?
F38 C38 C37 115.65(14) . . ?
F38 C38 C33 120.75(14) . . ?
C37 C38 C33 123.58(15) . . ?

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
C5 N1 N2 C3 -0.43(17) . . . . ?
C6 N1 N2 C3 176.95(14) . . . . ?
N1 N2 C3 N4 0.28(17) . . . . ?
N2 C3 N4 C5 -0.05(18) . . . . ?
N2 C3 N4 C12 -176.29(14) . . . . ?
N2 N1 C5 N4 0.42(17) . . . . ?
C6 N1 C5 N4 -176.75(14) . . . . ?
C3 N4 C5 N1 -0.22(16) . . . . ?
C12 N4 C5 N1 176.02(13) . . . . ?
C5 N1 C6 C11' 34.2(4) . . . . ?
N2 N1 C6 C11' -142.7(4) . . . . ?
C5 N1 C6 C7 -120.8(3) . . . . ?
N2 N1 C6 C7 62.3(3) . . . . ?
C5 N1 C6 C7' -134.7(3) . . . . ?
N2 N1 C6 C7' 48.3(3) . . . . ?
C5 N1 C6 C11 63.0(3) . . . . ?
N2 N1 C6 C11 -114.0(2) . . . . ?
C11' C6 C7 C8 24.4(5) . . . . ?
C7' C6 C7 C8 -115.4(13) . . . . ?
C11 C6 C7 C8 -2.6(5) . . . . ?
N1 C6 C7 C8 -178.7(3) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C6 -2.4(5) . . . . ?
C11' C6 C11 C10 -73.5(6) . . . . ?
C7 C6 C11 C10 3.5(4) . . . . ?
C7' C6 C11 C10 19.6(5) . . . . ?
N1 C6 C11 C10 179.8(2) . . . . ?
C11' C6 C7' C8' 5.4(7) . . . . ?
C7 C6 C7' C8' 50.6(11) . . . . ?
C11 C6 C7' C8' -25.4(7) . . . . ?
N1 C6 C7' C8' 174.1(4) . . . . ?
C6 C7' C8' C9' -1.7(8) . . . . ?
C7' C8' C9' C10' 2.3(9) . . . . ?
C8' C9' C10' C11' -6.2(9) . . . . ?
C7 C6 C11' C10' -20.2(7) . . . . ?
C7' C6 C11' C10' -9.3(7) . . . . ?
C11 C6 C11' C10' 95.2(8) . . . . ?
N1 C6 C11' C10' -177.4(4) . . . . ?
C9' C10' C11' C6 9.6(9) . . . . ?
C5 N4 C12 C17 148.59(15) . . . . ?
C3 N4 C12 C17 -35.9(2) . . . . ?
C5 N4 C12 C13 -35.7(2) . . . . ?
C3 N4 C12 C13 139.77(15) . . . . ?
C17 C12 C13 O19 178.38(13) . . . . ?
N4 C12 C13 O19 2.82(19) . . . . ?
C17 C12 C13 C14 -1.0(2) . . . . ?
N4 C12 C13 C14 -176.58(13) . . . . ?
O19 C13 C14 C15 -177.17(14) . . . . ?
C12 C13 C14 C15 2.2(2) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C14 C15 C16 C17 -0.9(2) . . . . ?
C14 C15 C16 C18 178.16(15) . . . . ?
C13 C12 C17 C16 -1.1(2) . . . . ?
N4 C12 C17 C16 174.37(13) . . . . ?
C15 C16 C17 C12 2.1(2) . . . . ?
C18 C16 C17 C12 -177.00(14) . . . . ?
C14 C13 O19 B20 37.2(2) . . . . ?
C12 C13 O19 B20 -142.12(13) . . . . ?
C13 O19 B20 C27 38.44(16) . . . . ?
C13 O19 B20 C21 -88.55(15) . . . . ?
C13 O19 B20 C33 158.77(12) . . . . ?
O19 B20 C21 C22 -4.9(2) . . . . ?
C27 B20 C21 C22 -126.30(15) . . . . ?
C33 B20 C21 C22 109.62(15) . . . . ?
O19 B20 C21 C26 -179.33(13) . . . . ?
C27 B20 C21 C26 59.30(18) . . . . ?
C33 B20 C21 C26 -64.78(17) . . . . ?
C26 C21 C22 F22 179.18(13) . . . . ?
B20 C21 C22 F22 4.4(2) . . . . ?
C26 C21 C22 C23 -2.6(2) . . . . ?
B20 C21 C22 C23 -177.36(14) . . . . ?
F22 C22 C23 F23 0.7(2) . . . . ?
C21 C22 C23 F23 -177.69(13) . . . . ?
F22 C22 C23 C24 177.97(13) . . . . ?
C21 C22 C23 C24 -0.4(2) . . . . ?
F23 C23 C24 F24 0.4(2) . . . . ?
C22 C23 C24 F24 -176.97(13) . . . . ?
F23 C23 C24 C25 179.83(14) . . . . ?
C22 C23 C24 C25 2.5(2) . . . . ?
F24 C24 C25 F25 -1.5(2) . . . . ?
C23 C24 C25 F25 179.07(14) . . . . ?
F24 C24 C25 C26 177.97(14) . . . . ?
C23 C24 C25 C26 -1.5(2) . . . . ?
F25 C25 C26 F26 -1.6(2) . . . . ?
C24 C25 C26 F26 178.94(14) . . . . ?
F25 C25 C26 C21 177.64(14) . . . . ?
C24 C25 C26 C21 -1.8(2) . . . . ?
C22 C21 C26 F26 -177.06(13) . . . . ?
B20 C21 C26 F26 -2.0(2) . . . . ?
C22 C21 C26 C25 3.7(2) . . . . ?
B20 C21 C26 C25 178.70(15) . . . . ?
O19 B20 C27 C28 -118.98(16) . . . . ?
C21 B20 C27 C28 5.7(2) . . . . ?
C33 B20 C27 C28 124.84(16) . . . . ?
O19 B20 C27 C32 53.51(17) . . . . ?
C21 B20 C27 C32 178.21(13) . . . . ?
C33 B20 C27 C32 -62.66(17) . . . . ?
C32 C27 C28 F28 -177.20(13) . . . . ?
B20 C27 C28 F28 -4.4(2) . . . . ?
C32 C27 C28 C29 1.0(2) . . . . ?
B20 C27 C28 C29 173.76(14) . . . . ?
F28 C28 C29 F29 -4.8(2) . . . . ?
C27 C28 C29 F29 176.90(14) . . . . ?
F28 C28 C29 C30 176.39(14) . . . . ?
C27 C28 C29 C30 -1.9(2) . . . . ?
F29 C29 C30 F30 0.5(2) . . . . ?
C28 C29 C30 F30 179.26(14) . . . . ?
F29 C29 C30 C31 -177.52(15) . . . . ?
C28 C29 C30 C31 1.3(2) . . . . ?
F30 C30 C31 F31 1.0(3) . . . . ?
C29 C30 C31 F31 178.98(15) . . . . ?
F30 C30 C31 C32 -177.88(15) . . . . ?
C29 C30 C31 C32 0.1(3) . . . . ?
F31 C31 C32 F32 0.8(2) . . . . ?
C30 C31 C32 F32 179.67(15) . . . . ?
F31 C31 C32 C27 -179.90(15) . . . . ?
C30 C31 C32 C27 -1.0(3) . . . . ?
C28 C27 C32 F32 179.77(13) . . . . ?
B20 C27 C32 F32 6.2(2) . . . . ?
C28 C27 C32 C31 0.5(2) . . . . ?
B20 C27 C32 C31 -173.07(15) . . . . ?
O19 B20 C33 C34 49.32(17) . . . . ?
C27 B20 C33 C34 164.97(13) . . . . ?
C21 B20 C33 C34 -69.07(16) . . . . ?
O19 B20 C33 C38 -139.60(15) . . . . ?
C27 B20 C33 C38 -24.0(2) . . . . ?
C21 B20 C33 C38 102.01(16) . . . . ?
C38 C33 C34 F34 -177.99(13) . . . . ?
B20 C33 C34 F34 -5.9(2) . . . . ?
C38 C33 C34 C35 0.3(2) . . . . ?
B20 C33 C34 C35 172.42(14) . . . . ?
F34 C34 C35 F35 -2.1(2) . . . . ?
C33 C34 C35 F35 179.58(14) . . . . ?
F34 C34 C35 C36 177.26(14) . . . . ?
C33 C34 C35 C36 -1.1(2) . . . . ?
F35 C35 C36 F36 0.8(2) . . . . ?
C34 C35 C36 F36 -178.53(15) . . . . ?
F35 C35 C36 C37 179.99(15) . . . . ?
C34 C35 C36 C37 0.7(2) . . . . ?
F36 C36 C37 F37 0.3(3) . . . . ?
C35 C36 C37 F37 -178.90(15) . . . . ?
F36 C36 C37 C38 179.67(15) . . . . ?
C35 C36 C37 C38 0.5(3) . . . . ?
F37 C37 C38 F38 -0.8(2) . . . . ?
C36 C37 C38 F38 179.83(15) . . . . ?
F37 C37 C38 C33 178.04(15) . . . . ?
C36 C37 C38 C33 -1.3(3) . . . . ?
C34 C33 C38 F38 179.68(14) . . . . ?
B20 C33 C38 F38 8.1(2) . . . . ?
C34 C33 C38 C37 0.9(2) . . . . ?
B20 C33 C38 C37 -170.71(15) . . . . ?

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
C3 H3 F23 0.95 2.54 3.0499(18) 113.7 1_455
C3 H3 F30 0.95 2.46 3.3280(19) 151.3 2_565
C5 H5 F34 0.95 2.62 3.4544(18) 146.6 .
C7 H7 F29 0.95 2.45 3.391(4) 171.1 1_545
C7' H7' F29 0.95 2.42 3.265(5) 147.5 1_545

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.049


_shelxl_version_number           2013-2




# start Validation Reply Form
_vrf_PLAT201_schm67_compound_15c 
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          5 Report
RESPONSE: disordered carbon atoms of the disordered phenyl group
refined isotropically
;
_database_code_depnum_ccdc_archive 'CCDC 1027082'
#######################################################################
#
#                 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_schm64_compound_16a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
4,4-diethyl-3-phenyl-4JH-benzo[e][1,2,4]triazolo[3,4-c]81,4,2]oxaza-borinin-3-ium-4-uide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 B N3 O1, 0.5(H2 O)'
_chemical_formula_sum            'C18 H21 B N3 O1.50'
_chemical_formula_weight         314.19

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.0122(4)
_cell_length_b                   11.1230(5)
_cell_length_c                   17.8748(9)
_cell_angle_alpha                72.078(4)
_cell_angle_beta                 87.907(4)
_cell_angle_gamma                79.532(4)
_cell_volume                     1676.14(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5167
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      29.94

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 dx = 46 mm, 1 deg., 2 x 10 sec., 6 sets, 385 frames
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  
'Agilent, SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'rotation in ω, 1°'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            13218
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.956
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7704
_reflns_number_gt                6094
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    Shelxtl-Plus
_computing_publication_material  publCIF

_refine_special_details          
;
 data were collected until theta 30 deg., but cutoff at theta 27.5 deg. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0394P)²+0.4454P]
 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     SHELXL
_refine_ls_extinction_coef       0.0072(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7704
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1 O 0.34279(11) 0.31250(8) 0.63584(6) 0.0268(2) Uani 1 1 d . . . . .
B2 B 0.40002(19) 0.17412(14) 0.63389(9) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.50733(16) 0.19656(12) 0.55659(8) 0.0234(3) Uani 1 1 d . . . . .
N4 N 0.62690(13) 0.12903(10) 0.53231(7) 0.0245(3) Uani 1 1 d . . . . .
N5 N 0.67516(14) 0.19332(11) 0.45886(7) 0.0280(3) Uani 1 1 d . . . . .
C6 C 0.58179(16) 0.30189(13) 0.43896(9) 0.0265(3) Uani 1 1 d . . . . .
H6 H 0.5852 0.3688 0.3910 0.032 Uiso 1 1 calc R U . . .
N7 N 0.47764(13) 0.30758(10) 0.49603(7) 0.0238(2) Uani 1 1 d . . . . .
C8 C 0.35566(16) 0.40928(12) 0.49676(8) 0.0246(3) Uani 1 1 d . . . . .
C9 C 0.30719(17) 0.50817(13) 0.42839(9) 0.0294(3) Uani 1 1 d . . . . .
H9 H 0.3540 0.5092 0.3798 0.035 Uiso 1 1 calc R U . . .
C10 C 0.18962(17) 0.60517(14) 0.43230(9) 0.0326(3) Uani 1 1 d . . . . .
H10 H 0.1558 0.6739 0.3862 0.039 Uiso 1 1 calc R U . . .
C11 C 0.12140(17) 0.60212(13) 0.50335(9) 0.0314(3) Uani 1 1 d . . . . .
H11 H 0.0402 0.6686 0.5056 0.038 Uiso 1 1 calc R U . . .
C12 C 0.17035(17) 0.50313(13) 0.57121(9) 0.0287(3) Uani 1 1 d . . . . .
H12 H 0.1224 0.5020 0.6196 0.034 Uiso 1 1 calc R U . . .
C13 C 0.28941(16) 0.40518(12) 0.56892(8) 0.0241(3) Uani 1 1 d . . . . .
C14 C 0.48882(18) 0.09907(13) 0.71601(9) 0.0311(3) Uani 1 1 d . . . . .
H14A H 0.4190 0.1065 0.7591 0.037 Uiso 1 1 calc R U . . .
H14B H 0.5145 0.0069 0.7200 0.037 Uiso 1 1 calc R U . . .
C15 C 0.6337(2) 0.14343(15) 0.72998(10) 0.0402(4) Uani 1 1 d . . . . .
H15A H 0.6771 0.0916 0.7818 0.060 Uiso 1 1 calc R U . . .
H15B H 0.6103 0.2340 0.7278 0.060 Uiso 1 1 calc R U . . .
H15C H 0.7064 0.1331 0.6893 0.060 Uiso 1 1 calc R U . . .
C16 C 0.25685(17) 0.11525(14) 0.61677(9) 0.0303(3) Uani 1 1 d . . . . .
H16A H 0.2155 0.1638 0.5633 0.036 Uiso 1 1 calc R U . . .
H16B H 0.2915 0.0247 0.6185 0.036 Uiso 1 1 calc R U . . .
C17 C 0.13267(19) 0.12142(17) 0.67620(11) 0.0405(4) Uani 1 1 d . . . . .
H17A H 0.0491 0.0848 0.6639 0.061 Uiso 1 1 calc R U . . .
H17B H 0.0963 0.2111 0.6738 0.061 Uiso 1 1 calc R U . . .
H17C H 0.1727 0.0723 0.7292 0.061 Uiso 1 1 calc R U . . .
C18 C 0.70870(16) 0.00304(13) 0.57175(8) 0.0262(3) Uani 1 1 d . . . . .
C19 C 0.63192(18) -0.09670(13) 0.60432(9) 0.0305(3) Uani 1 1 d . . . . .
H19 H 0.5248 -0.0825 0.6025 0.037 Uiso 1 1 calc R U . . .
C20 C 0.7146(2) -0.21859(14) 0.63998(10) 0.0387(4) Uani 1 1 d . . . . .
H20 H 0.6638 -0.2883 0.6634 0.046 Uiso 1 1 calc R U . . .
C21 C 0.8696(2) -0.23839(16) 0.64139(10) 0.0452(5) Uani 1 1 d . . . . .
H21 H 0.9253 -0.3222 0.6650 0.054 Uiso 1 1 calc R U . . .
C22 C 0.9453(2) -0.13771(17) 0.60882(10) 0.0450(4) Uani 1 1 d . . . . .
H22 H 1.0525 -0.1521 0.6106 0.054 Uiso 1 1 calc R U . . .
C23 C 0.86450(18) -0.01545(15) 0.57349(9) 0.0356(4) Uani 1 1 d . . . . .
H23 H 0.9155 0.0545 0.5508 0.043 Uiso 1 1 calc R U . . .
O101 O 0.17719(11) 0.52742(9) 0.81474(6) 0.0294(2) Uani 1 1 d . . . . .
B102 B 0.20750(19) 0.58242(16) 0.88096(10) 0.0278(3) Uani 1 1 d . . . . .
C103 C 0.05091(17) 0.68496(14) 0.87977(8) 0.0291(3) Uani 1 1 d . . . . .
N104 N 0.01199(15) 0.79674(12) 0.89563(8) 0.0359(3) Uani 1 1 d . . . . .
N105 N -0.13704(18) 0.85325(15) 0.87578(9) 0.0505(4) Uani 1 1 d . . . . .
C106 C -0.1876(2) 0.77318(18) 0.84851(11) 0.0485(5) Uani 1 1 d . . . . .
H106 H -0.2878 0.7853 0.8291 0.058 Uiso 1 1 calc R U . . .
N107 N -0.07883(14) 0.66884(12) 0.85107(7) 0.0336(3) Uani 1 1 d . . . . .
C108 C -0.08959(17) 0.55835(15) 0.82837(9) 0.0316(3) Uani 1 1 d . . . . .
C109 C -0.22751(18) 0.52350(18) 0.82252(10) 0.0406(4) Uani 1 1 d . . . . .
H109 H -0.3176 0.5713 0.8357 0.049 Uiso 1 1 calc R U . . .
C110 C -0.23308(19) 0.41882(18) 0.79746(10) 0.0432(4) Uani 1 1 d . . . . .
H110 H -0.3273 0.3948 0.7924 0.052 Uiso 1 1 calc R U . . .
C111 C -0.10077(19) 0.34900(17) 0.77966(10) 0.0398(4) Uani 1 1 d . . . . .
H111 H -0.1046 0.2764 0.7629 0.048 Uiso 1 1 calc R U . . .
C112 C 0.03760(18) 0.38368(15) 0.78598(9) 0.0327(3) Uani 1 1 d . . . . .
H112 H 0.1274 0.3351 0.7733 0.039 Uiso 1 1 calc R U . . .
C113 C 0.04521(16) 0.48939(14) 0.81091(8) 0.0281(3) Uani 1 1 d . . . . .
C114 C 0.22784(19) 0.46622(14) 0.96291(9) 0.0364(4) Uani 1 1 d . . . . .
H11A H 0.2419 0.5009 1.0065 0.044 Uiso 1 1 calc R U . . .
H11B H 0.1348 0.4287 0.9728 0.044 Uiso 1 1 calc R U . . .
C115 C 0.3628(2) 0.36030(17) 0.96240(12) 0.0521(5) Uani 1 1 d . . . . .
H11C H 0.3702 0.2920 1.0129 0.078 Uiso 1 1 calc R U . . .
H11D H 0.4557 0.3964 0.9542 0.078 Uiso 1 1 calc R U . . .
H11E H 0.3488 0.3249 0.9198 0.078 Uiso 1 1 calc R U . . .
C116 C 0.35056(19) 0.65112(16) 0.85334(10) 0.0380(4) Uani 1 1 d . . . . .
H11F H 0.3771 0.6850 0.8953 0.046 Uiso 1 1 calc R U . . .
H11G H 0.4371 0.5853 0.8484 0.046 Uiso 1 1 calc R U . . .
C117 C 0.3307(2) 0.76061(17) 0.77617(12) 0.0567(5) Uani 1 1 d . . . . .
H11H H 0.4240 0.7959 0.7647 0.085 Uiso 1 1 calc R U . . .
H11I H 0.2475 0.8282 0.7806 0.085 Uiso 1 1 calc R U . . .
H11J H 0.3078 0.7282 0.7335 0.085 Uiso 1 1 calc R U . . .
C118 C 0.1021(2) 0.86068(15) 0.93003(10) 0.0374(4) Uani 1 1 d . . . . .
C119 C 0.1940(2) 0.79139(16) 0.99440(11) 0.0444(4) Uani 1 1 d . . . . .
H119 H 0.1979 0.7015 1.0164 0.053 Uiso 1 1 calc R U . . .
C120 C 0.2805(2) 0.85470(18) 1.02656(13) 0.0522(5) Uani 1 1 d . . . . .
H120 H 0.3455 0.8079 1.0705 0.063 Uiso 1 1 calc R U . . .
C121 C 0.2727(2) 0.98553(19) 0.99495(13) 0.0558(5) Uani 1 1 d . . . . .
H121 H 0.3337 1.0285 1.0165 0.067 Uiso 1 1 calc R U . . .
C122 C 0.1763(3) 1.05395(18) 0.93198(13) 0.0600(6) Uani 1 1 d . . . . .
H122 H 0.1691 1.1444 0.9113 0.072 Uiso 1 1 calc R U . . .
C123 C 0.0902(2) 0.99206(16) 0.89880(11) 0.0497(5) Uani 1 1 d . . . . .
H123 H 0.0241 1.0390 0.8553 0.060 Uiso 1 1 calc R U . . .
O1W O 0.42106(13) 0.46857(11) 0.72038(7) 0.0330(3) Uani 1 1 d . . . . .
H1W1 H 0.398(2) 0.4066(19) 0.7035(12) 0.057(6) Uiso 1 1 d . . . . .
H1W2 H 0.340(3) 0.486(2) 0.7526(14) 0.069(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.3520(16) . ?
O1 B2 1.5426(17) . ?
B2 C14 1.606(2) . ?
B2 C16 1.627(2) . ?
B2 C3 1.639(2) . ?
C3 N4 1.3364(17) . ?
C3 N7 1.3590(17) . ?
N4 N5 1.3849(16) . ?
N4 C18 1.4348(17) . ?
N5 C6 1.2966(18) . ?
C6 N7 1.3689(18) . ?
C6 H6 0.9500 . ?
N7 C8 1.4298(17) . ?
C8 C9 1.3897(19) . ?
C8 C13 1.393(2) . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3926(19) . ?
C12 H12 0.9500 . ?
C14 C15 1.531(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.522(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.379(2) . ?
C18 C23 1.382(2) . ?
C19 C20 1.391(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
O101 C113 1.3435(17) . ?
O101 B102 1.5427(19) . ?
B102 C116 1.603(2) . ?
B102 C114 1.618(2) . ?
B102 C103 1.642(2) . ?
C103 N104 1.3418(18) . ?
C103 N107 1.356(2) . ?
N104 N105 1.3840(19) . ?
N104 C118 1.435(2) . ?
N105 C106 1.292(2) . ?
C106 N107 1.366(2) . ?
C106 H106 0.9500 . ?
N107 C108 1.427(2) . ?
C108 C109 1.384(2) . ?
C108 C113 1.394(2) . ?
C109 C110 1.379(2) . ?
C109 H109 0.9500 . ?
C110 C111 1.383(2) . ?
C110 H110 0.9500 . ?
C111 C112 1.389(2) . ?
C111 H111 0.9500 . ?
C112 C113 1.393(2) . ?
C112 H112 0.9500 . ?
C114 C115 1.534(2) . ?
C114 H11A 0.9900 . ?
C114 H11B 0.9900 . ?
C115 H11C 0.9800 . ?
C115 H11D 0.9800 . ?
C115 H11E 0.9800 . ?
C116 C117 1.524(3) . ?
C116 H11F 0.9900 . ?
C116 H11G 0.9900 . ?
C117 H11H 0.9800 . ?
C117 H11I 0.9800 . ?
C117 H11J 0.9800 . ?
C118 C119 1.376(2) . ?
C118 C123 1.380(2) . ?
C119 C120 1.384(3) . ?
C119 H119 0.9500 . ?
C120 C121 1.379(3) . ?
C120 H120 0.9500 . ?
C121 C122 1.380(3) . ?
C121 H121 0.9500 . ?
C122 C123 1.381(3) . ?
C122 H122 0.9500 . ?
C123 H123 0.9500 . ?
O1W H1W1 0.89(2) . ?
O1W H1W2 0.94(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 B2 119.55(10) . . ?
O1 B2 C14 106.04(11) . . ?
O1 B2 C16 108.60(12) . . ?
C14 B2 C16 115.62(12) . . ?
O1 B2 C3 102.34(10) . . ?
C14 B2 C3 114.55(12) . . ?
C16 B2 C3 108.66(11) . . ?
N4 C3 N7 103.40(12) . . ?
N4 C3 B2 136.47(12) . . ?
N7 C3 B2 120.11(11) . . ?
C3 N4 N5 113.28(11) . . ?
C3 N4 C18 128.98(12) . . ?
N5 N4 C18 117.74(11) . . ?
C6 N5 N4 103.50(11) . . ?
N5 C6 N7 111.16(12) . . ?
N5 C6 H6 124.4 . . ?
N7 C6 H6 124.4 . . ?
C3 N7 C6 108.65(11) . . ?
C3 N7 C8 122.60(12) . . ?
C6 N7 C8 128.75(12) . . ?
C9 C8 C13 121.86(13) . . ?
C9 C8 N7 121.12(13) . . ?
C13 C8 N7 117.02(12) . . ?
C10 C9 C8 118.93(14) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C11 C10 C9 120.05(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.64(14) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 120.37(14) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
O1 C13 C12 120.38(13) . . ?
O1 C13 C8 121.41(12) . . ?
C12 C13 C8 118.14(13) . . ?
C15 C14 B2 116.81(13) . . ?
C15 C14 H14A 108.1 . . ?
B2 C14 H14A 108.1 . . ?
C15 C14 H14B 108.1 . . ?
B2 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 B2 112.13(12) . . ?
C17 C16 H16A 109.2 . . ?
B2 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
B2 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 121.70(13) . . ?
C19 C18 N4 119.99(13) . . ?
C23 C18 N4 118.27(13) . . ?
C18 C19 C20 118.64(15) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C21 C20 C19 120.19(16) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.66(15) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 119.87(16) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 118.95(16) . . ?
C18 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C113 O101 B102 120.02(11) . . ?
O101 B102 C116 105.31(12) . . ?
O101 B102 C114 108.14(12) . . ?
C116 B102 C114 116.20(14) . . ?
O101 B102 C103 102.24(11) . . ?
C116 B102 C103 112.81(13) . . ?
C114 B102 C103 110.90(12) . . ?
N104 C103 N107 103.62(13) . . ?
N104 C103 B102 136.30(14) . . ?
N107 C103 B102 119.87(12) . . ?
C103 N104 N105 112.76(14) . . ?
C103 N104 C118 128.91(13) . . ?
N105 N104 C118 118.32(12) . . ?
C106 N105 N104 103.69(13) . . ?
N105 C106 N107 111.44(16) . . ?
N105 C106 H106 124.3 . . ?
N107 C106 H106 124.3 . . ?
C103 N107 C106 108.46(14) . . ?
C103 N107 C108 122.55(12) . . ?
C106 N107 C108 128.98(14) . . ?
C109 C108 C113 121.95(15) . . ?
C109 C108 N107 121.44(14) . . ?
C113 C108 N107 116.60(13) . . ?
C110 C109 C108 119.45(16) . . ?
C110 C109 H109 120.3 . . ?
C108 C109 H109 120.3 . . ?
C109 C110 C111 119.64(16) . . ?
C109 C110 H110 120.2 . . ?
C111 C110 H110 120.2 . . ?
C110 C111 C112 120.83(16) . . ?
C110 C111 H111 119.6 . . ?
C112 C111 H111 119.6 . . ?
C111 C112 C113 120.27(15) . . ?
C111 C112 H112 119.9 . . ?
C113 C112 H112 119.9 . . ?
O101 C113 C112 121.27(13) . . ?
O101 C113 C108 120.82(13) . . ?
C112 C113 C108 117.85(14) . . ?
C115 C114 B102 112.38(14) . . ?
C115 C114 H11A 109.1 . . ?
B102 C114 H11A 109.1 . . ?
C115 C114 H11B 109.1 . . ?
B102 C114 H11B 109.1 . . ?
H11A C114 H11B 107.9 . . ?
C114 C115 H11C 109.5 . . ?
C114 C115 H11D 109.5 . . ?
H11C C115 H11D 109.5 . . ?
C114 C115 H11E 109.5 . . ?
H11C C115 H11E 109.5 . . ?
H11D C115 H11E 109.5 . . ?
C117 C116 B102 115.97(15) . . ?
C117 C116 H11F 108.3 . . ?
B102 C116 H11F 108.3 . . ?
C117 C116 H11G 108.3 . . ?
B102 C116 H11G 108.3 . . ?
H11F C116 H11G 107.4 . . ?
C116 C117 H11H 109.5 . . ?
C116 C117 H11I 109.5 . . ?
H11H C117 H11I 109.5 . . ?
C116 C117 H11J 109.5 . . ?
H11H C117 H11J 109.5 . . ?
H11I C117 H11J 109.5 . . ?
C119 C118 C123 121.57(17) . . ?
C119 C118 N104 119.87(14) . . ?
C123 C118 N104 118.53(16) . . ?
C118 C119 C120 119.01(16) . . ?
C118 C119 H119 120.5 . . ?
C120 C119 H119 120.5 . . ?
C121 C120 C119 120.19(19) . . ?
C121 C120 H120 119.9 . . ?
C119 C120 H120 119.9 . . ?
C120 C121 C122 119.92(19) . . ?
C120 C121 H121 120.0 . . ?
C122 C121 H121 120.0 . . ?
C121 C122 C123 120.58(18) . . ?
C121 C122 H122 119.7 . . ?
C123 C122 H122 119.7 . . ?
C118 C123 C122 118.68(19) . . ?
C118 C123 H123 120.7 . . ?
C122 C123 H123 120.7 . . ?
H1W1 O1W H1W2 104.5(18) . . ?

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
C13 O1 B2 C14 167.13(12) . . . . ?
C13 O1 B2 C16 -68.01(15) . . . . ?
C13 O1 B2 C3 46.77(15) . . . . ?
O1 B2 C3 N4 153.36(15) . . . . ?
C14 B2 C3 N4 39.1(2) . . . . ?
C16 B2 C3 N4 -91.90(19) . . . . ?
O1 B2 C3 N7 -28.57(16) . . . . ?
C14 B2 C3 N7 -142.83(12) . . . . ?
C16 B2 C3 N7 86.17(14) . . . . ?
N7 C3 N4 N5 0.49(15) . . . . ?
B2 C3 N4 N5 178.77(14) . . . . ?
N7 C3 N4 C18 -179.81(12) . . . . ?
B2 C3 N4 C18 -1.5(3) . . . . ?
C3 N4 N5 C6 -0.01(15) . . . . ?
C18 N4 N5 C6 -179.75(12) . . . . ?
N4 N5 C6 N7 -0.49(15) . . . . ?
N4 C3 N7 C6 -0.76(14) . . . . ?
B2 C3 N7 C6 -179.39(12) . . . . ?
N4 C3 N7 C8 179.56(11) . . . . ?
B2 C3 N7 C8 0.93(19) . . . . ?
N5 C6 N7 C3 0.82(16) . . . . ?
N5 C6 N7 C8 -179.53(13) . . . . ?
C3 N7 C8 C9 -165.59(13) . . . . ?
C6 N7 C8 C9 14.8(2) . . . . ?
C3 N7 C8 C13 15.10(19) . . . . ?
C6 N7 C8 C13 -164.51(13) . . . . ?
C13 C8 C9 C10 -0.1(2) . . . . ?
N7 C8 C9 C10 -179.33(13) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
B2 O1 C13 C12 145.13(13) . . . . ?
B2 O1 C13 C8 -37.98(18) . . . . ?
C11 C12 C13 O1 176.26(13) . . . . ?
C11 C12 C13 C8 -0.7(2) . . . . ?
C9 C8 C13 O1 -176.27(12) . . . . ?
N7 C8 C13 O1 3.04(19) . . . . ?
C9 C8 C13 C12 0.7(2) . . . . ?
N7 C8 C13 C12 -179.99(12) . . . . ?
O1 B2 C14 C15 -65.85(16) . . . . ?
C16 B2 C14 C15 173.75(13) . . . . ?
C3 B2 C14 C15 46.22(17) . . . . ?
O1 B2 C16 C17 -55.58(16) . . . . ?
C14 B2 C16 C17 63.42(17) . . . . ?
C3 B2 C16 C17 -166.17(12) . . . . ?
C3 N4 C18 C19 48.6(2) . . . . ?
N5 N4 C18 C19 -131.69(14) . . . . ?
C3 N4 C18 C23 -133.56(16) . . . . ?
N5 N4 C18 C23 46.13(18) . . . . ?
C23 C18 C19 C20 0.3(2) . . . . ?
N4 C18 C19 C20 177.99(13) . . . . ?
C18 C19 C20 C21 -0.9(2) . . . . ?
C19 C20 C21 C22 1.1(3) . . . . ?
C20 C21 C22 C23 -0.7(3) . . . . ?
C19 C18 C23 C22 0.2(2) . . . . ?
N4 C18 C23 C22 -177.62(14) . . . . ?
C21 C22 C23 C18 0.1(3) . . . . ?
C113 O101 B102 C116 -164.91(12) . . . . ?
C113 O101 B102 C114 70.24(16) . . . . ?
C113 O101 B102 C103 -46.84(16) . . . . ?
O101 B102 C103 N104 -149.13(17) . . . . ?
C116 B102 C103 N104 -36.5(2) . . . . ?
C114 B102 C103 N104 95.8(2) . . . . ?
O101 B102 C103 N107 24.48(17) . . . . ?
C116 B102 C103 N107 137.08(15) . . . . ?
C114 B102 C103 N107 -90.60(16) . . . . ?
N107 C103 N104 N105 -1.69(17) . . . . ?
B102 C103 N104 N105 172.61(16) . . . . ?
N107 C103 N104 C118 177.50(15) . . . . ?
B102 C103 N104 C118 -8.2(3) . . . . ?
C103 N104 N105 C106 0.6(2) . . . . ?
C118 N104 N105 C106 -178.65(15) . . . . ?
N104 N105 C106 N107 0.7(2) . . . . ?
N104 C103 N107 C106 2.04(17) . . . . ?
B102 C103 N107 C106 -173.42(14) . . . . ?
N104 C103 N107 C108 -178.24(13) . . . . ?
B102 C103 N107 C108 6.3(2) . . . . ?
N105 C106 N107 C103 -1.8(2) . . . . ?
N105 C106 N107 C108 178.48(16) . . . . ?
C103 N107 C108 C109 159.85(15) . . . . ?
C106 N107 C108 C109 -20.5(3) . . . . ?
C103 N107 C108 C113 -21.4(2) . . . . ?
C106 N107 C108 C113 158.21(16) . . . . ?
C113 C108 C109 C110 -1.1(2) . . . . ?
N107 C108 C109 C110 177.52(15) . . . . ?
C108 C109 C110 C111 1.0(3) . . . . ?
C109 C110 C111 C112 -0.6(3) . . . . ?
C110 C111 C112 C113 0.4(2) . . . . ?
B102 O101 C113 C112 -144.40(14) . . . . ?
B102 O101 C113 C108 38.58(19) . . . . ?
C111 C112 C113 O101 -177.58(14) . . . . ?
C111 C112 C113 C108 -0.5(2) . . . . ?
C109 C108 C113 O101 177.97(14) . . . . ?
N107 C108 C113 O101 -0.7(2) . . . . ?
C109 C108 C113 C112 0.8(2) . . . . ?
N107 C108 C113 C112 -177.85(13) . . . . ?
O101 B102 C114 C115 61.83(17) . . . . ?
C116 B102 C114 C115 -56.26(19) . . . . ?
C103 B102 C114 C115 173.17(14) . . . . ?
O101 B102 C116 C117 60.44(17) . . . . ?
C114 B102 C116 C117 -179.93(13) . . . . ?
C103 B102 C116 C117 -50.26(19) . . . . ?
C103 N104 C118 C119 -44.0(2) . . . . ?
N105 N104 C118 C119 135.19(17) . . . . ?
C103 N104 C118 C123 138.20(18) . . . . ?
N105 N104 C118 C123 -42.7(2) . . . . ?
C123 C118 C119 C120 -2.5(3) . . . . ?
N104 C118 C119 C120 179.74(16) . . . . ?
C118 C119 C120 C121 0.9(3) . . . . ?
C119 C120 C121 C122 1.2(3) . . . . ?
C120 C121 C122 C123 -1.8(3) . . . . ?
C119 C118 C123 C122 1.9(3) . . . . ?
N104 C118 C123 C122 179.72(16) . . . . ?
C121 C122 C123 C118 0.2(3) . . . . ?

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
C6 H6 O1W 0.95 2.24 3.1840(18) 176.5 2_666
C9 H9 O1W 0.95 2.65 3.531(2) 154.5 2_666
O1W H1W1 O1 0.89(2) 1.95(2) 2.8163(15) 162.4(19) .
O1W H1W2 O101 0.94(2) 1.88(2) 2.8266(15) 178(2) .

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.039


_shelxl_version_number           2013-2





#==============================================================================
#_eof # End of Crystallographic Information File

_database_code_depnum_ccdc_archive 'CCDC 1027083'
