# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(1)
_database_code_depnum_ccdc_archive 'CCDC 1040156'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
2-((4-phenylpiperazin-1-yl)methyl)phenylboronic acid 
;
_chemical_formula_moiety         'C17 H21 B N2 O2'
_chemical_formula_sum            'C17 H21 B N2 O2'
_chemical_formula_weight         296.17
_chemical_melting_point          ?
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.3088(2)
_cell_length_b                   6.01200(10)
_cell_length_c                   19.8330(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.6467(14)
_cell_angle_gamma                90.00
_cell_volume                     1503.59(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27518
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.4903
_cell_measurement_theta_min      3.2224
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32627
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.23
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -89.00  -50.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -11.5933  155.0000  -87.0000    0.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega  -86.00  -33.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -11.5933  -45.0000  270.0000    0.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega  -71.00  -33.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -11.5933  128.0000  164.0000    0.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -37.00   16.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -11.5933  -45.0000  150.0000    0.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  5 omega  -87.00  -48.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -11.5933  153.0000   58.0000    0.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -83.00  -11.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -11.5933  147.0000    2.0000    0.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
  7 omega  -39.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -11.5933   45.0000  210.0000    0.0000    0.0000 102

#__ type_ start__ end____ width___ exp.time_
  8 omega  -45.00   13.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -11.5933   77.0000    0.0000    0.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega  -22.00   37.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.9058   77.0000   30.0000    0.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
 10 omega  -14.00   39.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.9058  -45.0000  300.0000    0.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega  -63.00  -28.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.9058  -45.0000   90.0000    0.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 12 omega  -14.00   39.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.9058  -45.0000  240.0000    0.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega  -10.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.9058   77.0000   90.0000    0.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.9058   45.0000  180.0000    0.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
 15 omega  -32.00   46.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.9058  -77.0000  300.0000    0.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
 16 omega   34.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.9058   45.0000  240.0000    0.0000    0.0000 53
;
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_orient_matrix_UB_11      -0.0190870956
_diffrn_orient_matrix_UB_12      -0.0643528659
_diffrn_orient_matrix_UB_13      -0.0315006029
_diffrn_orient_matrix_UB_21      -0.0365442143
_diffrn_orient_matrix_UB_22      -0.0533991089
_diffrn_orient_matrix_UB_23      0.0140037809
_diffrn_orient_matrix_UB_31      -0.0382410698
_diffrn_orient_matrix_UB_32      0.0832099794
_diffrn_orient_matrix_UB_33      -0.0153470939
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3053
_reflns_number_total             3276
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
K. Brandenburg Diamond - Crystal and Molecular Structure Visualization,
Version  3.2i; Crystal Impact GbR: Bonn, Germany.
Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst (1997), 30, 565
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
L. Spek Single-crystal structure validation with the program PLATON J. Appl.
Crystallogr. 36 (2003) 7-13.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.5981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C13(H13), C15(H15), C4(H4), C3(H3), C5(H5), C16(H16),
 C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40466(6) 0.65222(12) 0.51921(4) 0.01692(17) Uani 1 1 d . . .
H1 H 0.3410(14) 0.711(3) 0.5186(9) 0.045(4) Uiso 1 1 d . . .
O2 O 0.58855(5) 0.71675(13) 0.56171(4) 0.01831(17) Uani 1 1 d . . .
H2 H 0.5899(12) 0.604(3) 0.5351(9) 0.037(4) Uiso 1 1 d . . .
N1 N 0.23426(6) 0.84403(13) 0.53695(4) 0.01152(17) Uani 1 1 d . . .
N2 N 0.04813(6) 0.85360(13) 0.41295(4) 0.01318(18) Uani 1 1 d . . .
C12 C -0.02999(7) 0.83889(16) 0.34537(5) 0.0131(2) Uani 1 1 d . . .
C7 C 0.29175(7) 0.87512(16) 0.61352(5) 0.0136(2) Uani 1 1 d . . .
H7A H 0.3152 0.7279 0.6352 0.016 Uiso 1 1 calc R . .
H7B H 0.2422 0.9378 0.6366 0.016 Uiso 1 1 calc R . .
C9 C 0.08758(8) 0.64686(16) 0.45036(5) 0.0162(2) Uani 1 1 d . . .
H9A H 0.1363 0.5740 0.4285 0.019 Uiso 1 1 calc R . .
H9B H 0.0274 0.5448 0.4459 0.019 Uiso 1 1 calc R . .
C10 C 0.13427(8) 1.01356(16) 0.42269(5) 0.0158(2) Uani 1 1 d . . .
H10A H 0.1050 1.1560 0.3997 0.019 Uiso 1 1 calc R . .
H10B H 0.1848 0.9567 0.3994 0.019 Uiso 1 1 calc R . .
C11 C 0.19257(8) 1.05365(16) 0.50114(5) 0.0148(2) Uani 1 1 d . . .
H11A H 0.2517 1.1589 0.5062 0.018 Uiso 1 1 calc R . .
H11B H 0.1435 1.1211 0.5238 0.018 Uiso 1 1 calc R . .
C2 C 0.38741(7) 1.02598(16) 0.62887(5) 0.01249(19) Uani 1 1 d . . .
C14 C -0.17425(8) 0.63830(18) 0.25999(5) 0.0188(2) Uani 1 1 d . . .
H14 H -0.2154 0.5065 0.2473 0.023 Uiso 1 1 calc R . .
C17 C -0.05223(8) 1.01884(17) 0.29794(5) 0.0167(2) Uani 1 1 d . . .
H17 H -0.0105 1.1501 0.3097 0.020 Uiso 1 1 calc R . .
C13 C -0.09231(8) 0.64705(17) 0.32441(5) 0.0163(2) Uani 1 1 d . . .
H13 H -0.0782 0.5208 0.3548 0.020 Uiso 1 1 calc R . .
C8 C 0.14568(8) 0.69152(16) 0.52841(5) 0.0148(2) Uani 1 1 d . . .
H8A H 0.0958 0.7564 0.5509 0.018 Uiso 1 1 calc R . .
H8B H 0.1726 0.5495 0.5528 0.018 Uiso 1 1 calc R . .
C1 C 0.47769(7) 0.97394(16) 0.60911(5) 0.0132(2) Uani 1 1 d . . .
C15 C -0.19691(8) 0.81853(19) 0.21406(5) 0.0189(2) Uani 1 1 d . . .
H15 H -0.2534 0.8128 0.1703 0.023 Uiso 1 1 calc R . .
C4 C 0.47349(8) 1.35744(17) 0.69047(5) 0.0184(2) Uani 1 1 d . . .
H4 H 0.4713 1.4872 0.7173 0.022 Uiso 1 1 calc R . .
C3 C 0.38617(8) 1.21742(17) 0.66806(5) 0.0157(2) Uani 1 1 d . . .
H3 H 0.3242 1.2530 0.6797 0.019 Uiso 1 1 calc R . .
C5 C 0.56363(8) 1.30592(18) 0.67332(5) 0.0195(2) Uani 1 1 d . . .
H5 H 0.6245 1.3986 0.6891 0.023 Uiso 1 1 calc R . .
B1 B 0.48907(8) 0.76968(19) 0.56137(5) 0.0146(2) Uani 1 1 d . . .
C16 C -0.13482(8) 1.00733(18) 0.23375(5) 0.0188(2) Uani 1 1 d . . .
H16 H -0.1489 1.1320 0.2027 0.023 Uiso 1 1 calc R . .
C6 C 0.56466(8) 1.11793(17) 0.63283(5) 0.0170(2) Uani 1 1 d . . .
H6 H 0.6267 1.0858 0.6208 0.020 Uiso 1 1 calc R . .


_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 H1 0.915(18) . ?
O1 B1 1.3636(13) . ?
O2 H2 0.860(17) . ?
O2 B1 1.3595(13) . ?
N1 C7 1.4776(11) . ?
N1 C11 1.4658(12) . ?
N1 C8 1.4600(12) . ?
N2 C12 1.4122(12) . ?
N2 C9 1.4566(12) . ?
N2 C10 1.4612(12) . ?
C12 C17 1.4017(14) . ?
C12 C13 1.4037(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C2 1.5127(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.5168(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5195(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 C1 1.4129(13) . ?
C2 C3 1.3918(13) . ?
C14 H14 0.9500 . ?
C14 C13 1.3904(14) . ?
C14 C15 1.3853(16) . ?
C17 H17 0.9500 . ?
C17 C16 1.3925(14) . ?
C13 H13 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C1 B1 1.5871(14) . ?
C1 C6 1.4007(14) . ?
C15 H15 0.9500 . ?
C15 C16 1.3848(16) . ?
C4 H4 0.9500 . ?
C4 C3 1.3879(14) . ?
C4 C5 1.3826(16) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.3891(15) . ?
C16 H16 0.9500 . ?
C6 H6 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
B1 O1 H1 112.6(11) . . ?
B1 O2 H2 113.1(11) . . ?
C11 N1 C7 112.37(7) . . ?
C8 N1 C7 109.41(7) . . ?
C8 N1 C11 108.49(7) . . ?
C12 N2 C9 117.78(8) . . ?
C12 N2 C10 118.37(8) . . ?
C9 N2 C10 110.76(8) . . ?
C17 C12 N2 121.47(9) . . ?
C17 C12 C13 117.22(9) . . ?
C13 C12 N2 121.24(9) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
N1 C7 C2 114.12(7) . . ?
H7A C7 H7B 107.6 . . ?
C2 C7 H7A 108.7 . . ?
C2 C7 H7B 108.7 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 C8 110.60(8) . . ?
H9A C9 H9B 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
N2 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
N2 C10 C11 111.22(8) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N1 C11 C10 110.49(8) . . ?
N1 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C1 C2 C7 123.17(9) . . ?
C3 C2 C7 116.66(8) . . ?
C3 C2 C1 120.06(9) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C15 C14 C13 121.10(10) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.72(9) . . ?
C16 C17 H17 119.6 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.25(9) . . ?
C14 C13 H13 119.4 . . ?
N1 C8 C9 111.03(8) . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C2 C1 B1 126.06(9) . . ?
C6 C1 C2 117.04(9) . . ?
C6 C1 B1 116.90(9) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 118.09(9) . . ?
C16 C15 H15 121.0 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.27(9) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.48(9) . . ?
C4 C3 H3 119.3 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.61(9) . . ?
C6 C5 H5 120.2 . . ?
O1 B1 C1 123.33(9) . . ?
O2 B1 O1 119.47(9) . . ?
O2 B1 C1 117.17(9) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 C17 121.60(10) . . ?
C15 C16 H16 119.2 . . ?
C1 C6 H6 118.8 . . ?
C5 C6 C1 122.50(9) . . ?
C5 C6 H6 118.8 . . ?

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
N1 C7 C2 C1 -64.42(12) . . . . ?
N1 C7 C2 C3 119.40(9) . . . . ?
N2 C12 C17 C16 -175.17(9) . . . . ?
N2 C12 C13 C14 175.37(9) . . . . ?
N2 C9 C8 N1 -58.47(11) . . . . ?
N2 C10 C11 N1 57.51(11) . . . . ?
C12 N2 C9 C8 -164.01(8) . . . . ?
C12 N2 C10 C11 164.33(8) . . . . ?
C12 C17 C16 C15 -0.71(15) . . . . ?
C7 N1 C11 C10 179.97(7) . . . . ?
C7 N1 C8 C9 -177.39(8) . . . . ?
C7 C2 C1 B1 7.28(14) . . . . ?
C7 C2 C1 C6 -173.84(8) . . . . ?
C7 C2 C3 C4 174.32(8) . . . . ?
C9 N2 C12 C17 -162.94(9) . . . . ?
C9 N2 C12 C13 20.35(13) . . . . ?
C9 N2 C10 C11 -55.21(11) . . . . ?
C10 N2 C12 C17 -25.23(13) . . . . ?
C10 N2 C12 C13 158.06(9) . . . . ?
C10 N2 C9 C8 55.27(11) . . . . ?
C11 N1 C7 C2 -60.97(10) . . . . ?
C11 N1 C8 C9 59.70(10) . . . . ?
C2 C1 B1 O1 17.10(15) . . . . ?
C2 C1 B1 O2 -165.03(9) . . . . ?
C2 C1 C6 C5 -0.74(14) . . . . ?
C14 C15 C16 C17 -0.50(15) . . . . ?
C17 C12 C13 C14 -1.47(14) . . . . ?
C13 C12 C17 C16 1.66(14) . . . . ?
C13 C14 C15 C16 0.70(15) . . . . ?
C8 N1 C7 C2 178.46(8) . . . . ?
C8 N1 C11 C10 -58.93(10) . . . . ?
C1 C2 C3 C4 -1.98(14) . . . . ?
C15 C14 C13 C12 0.31(15) . . . . ?
C4 C5 C6 C1 -1.02(15) . . . . ?
C3 C2 C1 B1 -176.67(9) . . . . ?
C3 C2 C1 C6 2.21(13) . . . . ?
C3 C4 C5 C6 1.31(15) . . . . ?
C5 C4 C3 C2 0.17(14) . . . . ?
B1 C1 C6 C5 178.23(9) . . . . ?
C6 C1 B1 O1 -161.78(9) . . . . ?
C6 C1 B1 O2 16.10(13) . . . . ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(2)
_database_code_depnum_ccdc_archive 'CCDC 1040157'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
2-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)phenylboronic acid 
;
_chemical_formula_moiety         'C18 H23 B N2 O3'
_chemical_formula_sum            'C18 H23 B N2 O3'
_chemical_formula_weight         326.19
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x, -y+1/2, z+1/2'

_cell_length_a                   12.1978(3)
_cell_length_b                   19.2053(5)
_cell_length_c                   15.5424(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.000(3)
_cell_angle_gamma                90.00
_cell_volume                     3621.05(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.9880
_cell_measurement_theta_min      4.2880
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13981
_diffrn_reflns_theta_full        67.09
_diffrn_reflns_theta_max         67.09
_diffrn_reflns_theta_min         3.67
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.9946
_diffrn_measured_fraction_theta_max 0.9946
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   29.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9333   37.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega   57.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9333 -125.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   27.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9333   37.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega -113.00  -87.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00   52.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -53.0000   70.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega   62.00   88.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -53.0000   70.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   88.00  132.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -49.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega  122.00  177.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
  9 omega   90.00  131.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -88.0000 -127.0000 41

#__ type_ start__ end____ width___ exp.time_
 10 omega   25.00   72.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega  128.00  168.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 12 omega   65.00  166.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 13 omega   27.00   67.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 14 omega   51.00   93.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -57.0000 -140.0000 42

#__ type_ start__ end____ width___ exp.time_
 15 omega   59.00  112.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega   34.00   61.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   55.00  164.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000  -30.0000 109

#__ type_ start__ end____ width___ exp.time_
 18 omega   72.00   99.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega    9.00   47.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -88.0000 -127.0000 38

#__ type_ start__ end____ width___ exp.time_
 20 omega   32.00   59.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega   10.00   41.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -49.0000 31

#__ type_ start__ end____ width___ exp.time_
 22 omega   96.00  130.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000 -162.0000 34

#__ type_ start__ end____ width___ exp.time_
 23 omega   15.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9333   37.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 24 omega    7.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9333   77.0000  150.0000 113
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1222561000
_diffrn_orient_matrix_UB_12      0.0011769000
_diffrn_orient_matrix_UB_13      -0.0167594000
_diffrn_orient_matrix_UB_21      -0.0340411000
_diffrn_orient_matrix_UB_22      -0.0058794000
_diffrn_orient_matrix_UB_23      -0.0979802000
_diffrn_orient_matrix_UB_31      -0.0042894000
_diffrn_orient_matrix_UB_32      0.0800112000
_diffrn_orient_matrix_UB_33      -0.0069732000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2777
_reflns_number_total             3226
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
K. Brandenburg Diamond - Crystal and Molecular Structure Visualization,
 Version  3.2i; Crystal Impact GbR: Bonn, Germany.
Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst (1997), 30, 565
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
L. Spek Single-crystal structure validation with the program PLATON J. Appl.
Crystallogr. 36 (2003) 7-13.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0537P)²+1.7724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          SQUEEZE
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.68347(8) 0.48990(5) 1.09891(7) 0.0387(3) Uani 1 1 d . . .
O1 O 0.37245(8) 0.28819(6) 0.78817(6) 0.0393(3) Uani 1 1 d . . .
H1 H 0.4313 0.3005 0.8171 0.059 Uiso 1 1 calc R . .
N2 N 0.58565(9) 0.36956(5) 1.04036(7) 0.0287(3) Uani 1 1 d . . .
N1 N 0.56774(9) 0.31753(5) 0.86535(7) 0.0269(3) Uani 1 1 d . . .
O2 O 0.29281(9) 0.28583(7) 0.64350(7) 0.0509(3) Uani 1 1 d . . .
H2 H 0.2416 0.2685 0.6686 0.076 Uiso 1 1 calc R . .
C17 C 0.61588(12) 0.45897(7) 1.15255(9) 0.0369(4) Uani 1 1 d . . .
C12 C 0.56350(12) 0.39641(7) 1.12159(9) 0.0324(3) Uani 1 1 d . . .
C7 C 0.62195(11) 0.29272(7) 0.79088(9) 0.0308(3) Uani 1 1 d . . .
H7A H 0.6014 0.2435 0.7795 0.037 Uiso 1 1 calc R . .
H7B H 0.7028 0.2946 0.8057 0.037 Uiso 1 1 calc R . .
C11 C 0.60261(11) 0.38954(7) 0.88766(9) 0.0292(3) Uani 1 1 d . . .
H11A H 0.5804 0.4207 0.8381 0.035 Uiso 1 1 calc R . .
H11B H 0.6839 0.3913 0.8994 0.035 Uiso 1 1 calc R . .
C10 C 0.55107(11) 0.41441(7) 0.96605(8) 0.0285(3) Uani 1 1 d . . .
H10A H 0.5739 0.4630 0.9794 0.034 Uiso 1 1 calc R . .
H10B H 0.4698 0.4134 0.9541 0.034 Uiso 1 1 calc R . .
C16 C 0.59701(15) 0.48501(8) 1.23288(10) 0.0465(4) Uani 1 1 d . . .
H16 H 0.6307 0.5275 1.2526 0.056 Uiso 1 1 calc R . .
C8 C 0.59749(12) 0.27232(7) 0.94054(9) 0.0305(3) Uani 1 1 d . . .
H8A H 0.6788 0.2703 0.9523 0.037 Uiso 1 1 calc R . .
H8B H 0.5704 0.2246 0.9270 0.037 Uiso 1 1 calc R . .
C14 C 0.47987(16) 0.38856(9) 1.25667(10) 0.0499(4) Uani 1 1 d . . .
H14 H 0.4347 0.3640 1.2926 0.060 Uiso 1 1 calc R . .
C9 C 0.54935(12) 0.29822(7) 1.02038(9) 0.0315(3) Uani 1 1 d . . .
H9A H 0.4679 0.2968 1.0106 0.038 Uiso 1 1 calc R . .
H9B H 0.5732 0.2675 1.0700 0.038 Uiso 1 1 calc R . .
C13 C 0.49600(13) 0.36256(8) 1.17516(10) 0.0396(4) Uani 1 1 d . . .
H13 H 0.4600 0.3207 1.1557 0.048 Uiso 1 1 calc R . .
C1 C 0.48293(13) 0.33760(7) 0.66833(9) 0.0367(3) Uani 1 1 d . . .
C2 C 0.59201(12) 0.33455(7) 0.70927(9) 0.0338(3) Uani 1 1 d . . .
C3 C 0.67662(15) 0.36823(8) 0.67290(10) 0.0431(4) Uani 1 1 d . . .
H3 H 0.7494 0.3663 0.7013 0.052 Uiso 1 1 calc R . .
C6 C 0.46591(16) 0.37373(9) 0.58977(10) 0.0479(4) Uani 1 1 d . . .
H6 H 0.3938 0.3757 0.5602 0.057 Uiso 1 1 calc R . .
C4 C 0.65699(18) 0.40446(9) 0.59622(11) 0.0554(5) Uani 1 1 d . . .
H4 H 0.7156 0.4278 0.5726 0.066 Uiso 1 1 calc R . .
C15 C 0.52951(16) 0.44985(9) 1.28473(10) 0.0529(5) Uani 1 1 d . . .
H15 H 0.5176 0.4682 1.3398 0.063 Uiso 1 1 calc R . .
C18 C 0.75317(14) 0.54531(8) 1.13336(13) 0.0527(5) Uani 1 1 d . . .
H18A H 0.8029 0.5591 1.0908 0.079 Uiso 1 1 calc R . .
H18B H 0.7966 0.5296 1.1864 0.079 Uiso 1 1 calc R . .
H18C H 0.7077 0.5852 1.1465 0.079 Uiso 1 1 calc R . .
B1 B 0.37880(14) 0.30213(9) 0.70306(11) 0.0378(4) Uani 1 1 d . . .
C5 C 0.55167(19) 0.40667(9) 0.55401(11) 0.0573(5) Uani 1 1 d . . .
H5 H 0.5379 0.4307 0.5006 0.069 Uiso 1 1 calc R . .


_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
O3 C17 1.368(2) . ?
O3 C18 1.4306(18) . ?
O1 H1 0.8400 . ?
O1 B1 1.360(2) . ?
N2 C12 1.4158(18) . ?
N2 C10 1.4668(16) . ?
N2 C9 1.4632(17) . ?
N1 C7 1.4709(17) . ?
N1 C11 1.4776(16) . ?
N1 C8 1.4705(17) . ?
O2 H2 0.8400 . ?
O2 B1 1.3609(19) . ?
C17 C12 1.421(2) . ?
C17 C16 1.386(2) . ?
C12 C13 1.392(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C2 1.5136(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.5059(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C15 1.386(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.512(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.395(2) . ?
C14 C15 1.374(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C13 H13 0.9500 . ?
C1 C2 1.415(2) . ?
C1 C6 1.401(2) . ?
C1 B1 1.585(3) . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
C15 H15 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 H5 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
C17 O3 C18 117.86(13) . . ?
B1 O1 H1 109.5 . . ?
C12 N2 C10 114.98(10) . . ?
C12 N2 C9 116.65(11) . . ?
C9 N2 C10 109.09(10) . . ?
C7 N1 C11 110.23(10) . . ?
C8 N1 C7 109.89(10) . . ?
C8 N1 C11 108.97(10) . . ?
B1 O2 H2 109.5 . . ?
O3 C17 C12 116.05(12) . . ?
O3 C17 C16 124.03(14) . . ?
C16 C17 C12 119.92(16) . . ?
N2 C12 C17 119.27(13) . . ?
C13 C12 N2 122.91(13) . . ?
C13 C12 C17 117.75(13) . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
N1 C7 C2 113.49(11) . . ?
H7A C7 H7B 107.7 . . ?
C2 C7 H7A 108.9 . . ?
C2 C7 H7B 108.9 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 C10 110.64(11) . . ?
H11A C11 H11B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
N2 C10 C11 109.92(10) . . ?
N2 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C17 C16 H16 119.6 . . ?
C17 C16 C15 120.82(16) . . ?
C15 C16 H16 119.6 . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 111.93(11) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.73(17) . . ?
N2 C9 C8 110.33(11) . . ?
N2 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C12 C13 C14 121.64(16) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C2 C1 B1 125.34(13) . . ?
C6 C1 C2 117.34(15) . . ?
C6 C1 B1 117.31(14) . . ?
C1 C2 C7 122.15(13) . . ?
C3 C2 C7 117.66(14) . . ?
C3 C2 C1 120.14(14) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.19(17) . . ?
C4 C3 H3 119.4 . . ?
C1 C6 H6 119.1 . . ?
C5 C6 C1 121.72(17) . . ?
C5 C6 H6 119.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.67(18) . . ?
C5 C4 H4 120.2 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.11(15) . . ?
C14 C15 H15 119.9 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 B1 O2 119.88(16) . . ?
O1 B1 C1 123.03(13) . . ?
O2 B1 C1 117.08(14) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.91(16) . . ?
C4 C5 H5 120.0 . . ?

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
O3 C17 C12 N2 1.47(17) . . . . ?
O3 C17 C12 C13 178.60(11) . . . . ?
O3 C17 C16 C15 -178.35(13) . . . . ?
N2 C12 C13 C14 176.88(13) . . . . ?
N1 C7 C2 C1 -63.16(16) . . . . ?
N1 C7 C2 C3 119.43(13) . . . . ?
N1 C11 C10 N2 60.53(13) . . . . ?
N1 C8 C9 N2 -57.31(14) . . . . ?
C17 C12 C13 C14 -0.1(2) . . . . ?
C17 C16 C15 C14 -0.3(2) . . . . ?
C12 N2 C10 C11 166.26(11) . . . . ?
C12 N2 C9 C8 -169.10(11) . . . . ?
C12 C17 C16 C15 1.6(2) . . . . ?
C7 N1 C11 C10 -177.74(10) . . . . ?
C7 N1 C8 C9 176.52(10) . . . . ?
C7 C2 C3 C4 176.69(14) . . . . ?
C11 N1 C7 C2 -62.33(14) . . . . ?
C11 N1 C8 C9 55.65(14) . . . . ?
C10 N2 C12 C17 -63.39(15) . . . . ?
C10 N2 C12 C13 119.65(14) . . . . ?
C10 N2 C9 C8 58.55(14) . . . . ?
C16 C17 C12 N2 -178.49(12) . . . . ?
C16 C17 C12 C13 -1.36(19) . . . . ?
C8 N1 C7 C2 177.56(11) . . . . ?
C8 N1 C11 C10 -57.07(14) . . . . ?
C9 N2 C12 C17 167.01(11) . . . . ?
C9 N2 C12 C13 -9.96(18) . . . . ?
C9 N2 C10 C11 -60.51(14) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C1 C6 C5 C4 -0.2(2) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C1 B1 O1 26.0(2) . . . . ?
C2 C1 B1 O2 -154.36(14) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C6 C1 C2 C7 -175.49(13) . . . . ?
C6 C1 C2 C3 1.9(2) . . . . ?
C6 C1 B1 O1 -155.36(14) . . . . ?
C6 C1 B1 O2 24.3(2) . . . . ?
C15 C14 C13 C12 1.4(2) . . . . ?
C18 O3 C17 C12 -168.77(12) . . . . ?
C18 O3 C17 C16 11.19(19) . . . . ?
B1 C1 C2 C7 3.1(2) . . . . ?
B1 C1 C2 C3 -179.52(13) . . . . ?
B1 C1 C6 C5 179.87(14) . . . . ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(3)
_database_code_depnum_ccdc_archive 'CCDC 1040158'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
2-((4-(2,3-dichlorophenyl)piperazin-1-yl)methyl)phenylboronic acid
;
_chemical_formula_moiety         'C17 H19 B Cl2 N2 O2'
_chemical_formula_sum            'C17 H19 B Cl2 N2 O2'
_chemical_formula_weight         365.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.9155(4)
_cell_length_b                   10.3130(4)
_cell_length_c                   11.8333(7)
_cell_angle_alpha                88.456(4)
_cell_angle_beta                 72.897(5)
_cell_angle_gamma                69.370(4)
_cell_volume                     860.88(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    3.489
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7576
_diffrn_reflns_theta_full        66.49
_diffrn_reflns_theta_max         66.49
_diffrn_reflns_theta_min         3.92
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2863
_reflns_number_total             3018
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
K. Brandenburg Diamond - Crystal and Molecular Structure Visualization,
 Version  3.2i; Crystal Impact GbR: Bonn, Germany.
Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst (1997), 30, 565
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
L. Spek Single-crystal structure validation with the program PLATON J. Appl.
Crystallogr. 36 (2003) 7-13.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0954P)²+0.2175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1290
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 1.08695(6) -0.03914(5) 0.21830(4) 0.02232(18) Uani 1 d . . .
Cl2 Cl 1.41009(6) -0.31624(5) 0.09565(4) 0.02621(19) Uani 1 d . . .
O1 O 0.12049(19) 0.10218(13) 0.44057(12) 0.0185(3) Uani 1 d . . .
H1 H 0.205(4) 0.124(3) 0.391(3) 0.041(8) Uiso 1 d . . .
O2 O -0.21019(18) 0.18386(15) 0.52700(12) 0.0216(3) Uani 1 d . . .
H2 H -0.188(4) 0.104(3) 0.545(3) 0.039(7) Uiso 1 d . . .
N1 N 0.3700(2) 0.20676(15) 0.32106(13) 0.0147(3) Uani 1 d . . .
N2 N 0.7175(2) 0.00942(15) 0.17514(13) 0.0152(3) Uani 1 d . . .
C1 C -0.0794(3) 0.34995(18) 0.40414(15) 0.0148(4) Uani 1 d . . .
C2 C 0.0626(2) 0.40774(18) 0.36032(15) 0.0153(4) Uani 1 d . . .
C3 C 0.0237(3) 0.52938(19) 0.30253(17) 0.0204(4) Uani 1 d . . .
H3 H 0.1202 0.5671 0.2728 0.025 Uiso 1 calc . . R
C4 C -0.1530(3) 0.59654(19) 0.28748(17) 0.0231(4) Uani 1 d . . .
H4 H -0.1755 0.6778 0.2457 0.028 Uiso 1 calc . . R
C5 C -0.2965(3) 0.54487(19) 0.33346(17) 0.0216(4) Uani 1 d . . .
H5 H -0.4190 0.5918 0.3257 0.026 Uiso 1 calc . . R
C6 C -0.2587(3) 0.42313(18) 0.39125(16) 0.0178(4) Uani 1 d . . .
H6 H -0.3578 0.3884 0.4231 0.021 Uiso 1 calc . . R
C7 C 0.2542(2) 0.34735(18) 0.38167(16) 0.0169(4) Uani 1 d . . .
H7A H 0.3248 0.4104 0.3537 0.020 Uiso 1 calc . . R
H7B H 0.2345 0.3429 0.4681 0.020 Uiso 1 calc . . R
C8 C 0.5348(2) 0.14370(19) 0.36462(16) 0.0174(4) Uani 1 d . . .
H8A H 0.4913 0.1387 0.4515 0.021 Uiso 1 calc . . R
H8B H 0.6142 0.2019 0.3481 0.021 Uiso 1 calc . . R
C9 C 0.6502(3) -0.00069(19) 0.30379(15) 0.0171(4) Uani 1 d . . .
H9A H 0.7596 -0.0442 0.3341 0.021 Uiso 1 calc . . R
H9B H 0.5714 -0.0593 0.3204 0.021 Uiso 1 calc . . R
C10 C 0.5546(2) 0.06748(18) 0.13032(16) 0.0166(4) Uani 1 d . . .
H10A H 0.4788 0.0067 0.1460 0.020 Uiso 1 calc . . R
H10B H 0.5988 0.0732 0.0435 0.020 Uiso 1 calc . . R
C11 C 0.4338(3) 0.21167(19) 0.19223(15) 0.0176(4) Uani 1 d . . .
H11A H 0.5083 0.2732 0.1726 0.021 Uiso 1 calc . . R
H11B H 0.3222 0.2512 0.1633 0.021 Uiso 1 calc . . R
C12 C 0.8676(2) -0.10832(18) 0.10922(15) 0.0154(4) Uani 1 d . . .
C13 C 1.0465(3) -0.14495(18) 0.12660(15) 0.0167(4) Uani 1 d . . .
C14 C 1.1935(3) -0.2651(2) 0.06726(17) 0.0199(4) Uani 1 d . . .
C15 C 1.1714(3) -0.3464(2) -0.01516(18) 0.0240(4) Uani 1 d . . .
H15 H 1.2730 -0.4279 -0.0556 0.029 Uiso 1 calc . . R
C16 C 0.9986(3) -0.3062(2) -0.03711(18) 0.0252(4) Uani 1 d . . .
H16 H 0.9828 -0.3584 -0.0956 0.030 Uiso 1 calc . . R
C17 C 0.8483(3) -0.19039(19) 0.02547(17) 0.0201(4) Uani 1 d . . .
H17 H 0.7295 -0.1663 0.0111 0.024 Uiso 1 calc . . R
B1 B -0.0520(3) 0.2052(2) 0.46134(17) 0.0165(4) Uani 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
Cl1 C13 1.7278(19) . ?
Cl2 C14 1.7384(19) . ?
O1 H1 0.85(3) . ?
O1 B1 1.359(3) . ?
O2 H2 0.81(3) . ?
O2 B1 1.354(2) . ?
N1 C7 1.480(2) . ?
N1 C8 1.473(2) . ?
N1 C11 1.464(2) . ?
N2 C9 1.472(2) . ?
N2 C10 1.464(2) . ?
N2 C12 1.408(2) . ?
C1 C2 1.414(3) . ?
C1 C6 1.404(3) . ?
C1 B1 1.593(3) . ?
C2 C3 1.393(3) . ?
C2 C7 1.518(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.511(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.519(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.407(3) . ?
C12 C17 1.395(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(3) . ?
C17 H17 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
B1 O1 H1 110.8(19) . . ?
B1 O2 H2 112(2) . . ?
C8 N1 C7 110.09(14) . . ?
C11 N1 C7 111.18(14) . . ?
C11 N1 C8 109.88(13) . . ?
C10 N2 C9 109.41(13) . . ?
C12 N2 C9 115.83(14) . . ?
C12 N2 C10 116.72(14) . . ?
C2 C1 B1 125.85(16) . . ?
C6 C1 C2 117.33(16) . . ?
C6 C1 B1 116.74(16) . . ?
C1 C2 C7 122.06(15) . . ?
C3 C2 C1 119.86(16) . . ?
C3 C2 C7 117.94(16) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.37(17) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.86(17) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.10(17) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 H6 118.8 . . ?
C5 C6 C1 122.41(17) . . ?
C5 C6 H6 118.8 . . ?
N1 C7 C2 113.25(14) . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C2 C7 H7A 108.9 . . ?
C2 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
N1 C8 C9 109.67(14) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
N2 C9 C8 108.85(14) . . ?
N2 C9 H9A 109.9 . . ?
N2 C9 H9B 109.9 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 H10A 109.9 . . ?
N2 C10 H10B 109.9 . . ?
N2 C10 C11 108.88(14) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
N1 C11 C10 111.08(14) . . ?
N1 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 N2 119.12(16) . . ?
C17 C12 N2 122.98(16) . . ?
C17 C12 C13 117.90(16) . . ?
C12 C13 Cl1 120.46(14) . . ?
C14 C13 Cl1 119.56(14) . . ?
C14 C13 C12 119.95(17) . . ?
C13 C14 Cl2 119.99(15) . . ?
C15 C14 Cl2 118.74(15) . . ?
C15 C14 C13 121.27(18) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.72(17) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.53(18) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.44(18) . . ?
C16 C17 H17 119.3 . . ?
O1 B1 C1 122.51(16) . . ?
O2 B1 O1 120.07(16) . . ?
O2 B1 C1 117.30(16) . . ?

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
Cl1 C13 C14 Cl2 5.8(2) . . . . ?
Cl1 C13 C14 C15 -174.28(15) . . . . ?
Cl2 C14 C15 C16 179.54(15) . . . . ?
N1 C8 C9 N2 60.80(18) . . . . ?
N2 C10 C11 N1 -58.28(19) . . . . ?
N2 C12 C13 Cl1 -5.3(2) . . . . ?
N2 C12 C13 C14 176.44(16) . . . . ?
N2 C12 C17 C16 -179.48(17) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C7 N1 66.5(2) . . . . ?
C2 C1 C6 C5 2.7(3) . . . . ?
C2 C1 B1 O1 -21.7(3) . . . . ?
C2 C1 B1 O2 162.34(16) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C3 C2 C7 N1 -117.92(18) . . . . ?
C3 C4 C5 C6 -1.9(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C6 C1 C2 C3 -2.7(2) . . . . ?
C6 C1 C2 C7 172.81(16) . . . . ?
C6 C1 B1 O1 155.18(17) . . . . ?
C6 C1 B1 O2 -20.8(2) . . . . ?
C7 N1 C8 C9 179.01(14) . . . . ?
C7 N1 C11 C10 179.31(14) . . . . ?
C7 C2 C3 C4 -175.20(16) . . . . ?
C8 N1 C7 C2 -168.54(14) . . . . ?
C8 N1 C11 C10 57.18(18) . . . . ?
C9 N2 C10 C11 60.51(18) . . . . ?
C9 N2 C12 C13 -66.8(2) . . . . ?
C9 N2 C12 C17 114.08(19) . . . . ?
C10 N2 C9 C8 -62.37(18) . . . . ?
C10 N2 C12 C13 162.13(15) . . . . ?
C10 N2 C12 C17 -17.0(2) . . . . ?
C11 N1 C7 C2 69.45(18) . . . . ?
C11 N1 C8 C9 -58.22(18) . . . . ?
C12 N2 C9 C8 163.18(15) . . . . ?
C12 N2 C10 C11 -165.50(14) . . . . ?
C12 C13 C14 Cl2 -175.97(13) . . . . ?
C12 C13 C14 C15 4.0(3) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -2.6(3) . . . . ?
C15 C16 C17 C12 2.2(3) . . . . ?
C17 C12 C13 Cl1 173.87(13) . . . . ?
C17 C12 C13 C14 -4.4(2) . . . . ?
B1 C1 C2 C3 174.11(16) . . . . ?
B1 C1 C2 C7 -10.4(3) . . . . ?
B1 C1 C6 C5 -174.41(17) . . . . ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(4)
_database_code_depnum_ccdc_archive 'CCDC 1040159'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
2-((4-(4-nitrophenyl)piperazin-1-yl)methyl)phenylboronic acid
;
_chemical_formula_moiety         'C17 H20 B N3 O4'
_chemical_formula_sum            'C17 H20 B N3 O4'
_chemical_formula_weight         341.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.32568(6)
_cell_length_b                   9.10656(10)
_cell_length_c                   18.03844(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.7068(6)
_cell_angle_gamma                90.00
_cell_volume                     1696.05(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    42945
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.1220
_cell_measurement_theta_min      4.2570
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            77017
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.90
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9978
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00  -32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.5498  -45.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
  2 omega  -36.00   17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.5498  -45.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega   31.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   77.0000  300.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega   32.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   45.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
  5 omega  -35.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.5498  -77.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega  -23.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   77.0000  270.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega   31.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   77.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega  -14.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498  -77.0000  210.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   18.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.5498    0.0000   90.0000 61

#__ type_ start__ end____ width___ exp.time_
 10 omega   32.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   45.0000  270.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   31.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   77.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   18.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.5498    0.0000  300.0000 61

#__ type_ start__ end____ width___ exp.time_
 13 omega  -35.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.5498  -77.0000  270.0000 58

#__ type_ start__ end____ width___ exp.time_
 14 omega  -15.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498  -45.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega  -14.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498  -77.0000  330.0000 58

#__ type_ start__ end____ width___ exp.time_
 16 omega  -14.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498  -77.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 17 omega   32.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   45.0000  180.0000 53

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   45.0000  300.0000 53

#__ type_ start__ end____ width___ exp.time_
 19 omega  -38.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.5498   45.0000  180.0000 53

#__ type_ start__ end____ width___ exp.time_
 20 omega -114.00  -58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -70.0000  130.0000 56

#__ type_ start__ end____ width___ exp.time_
 21 omega -115.00  -62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -45.0000  330.0000 53

#__ type_ start__ end____ width___ exp.time_
 22 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  240.0000 58

#__ type_ start__ end____ width___ exp.time_
 23 omega  -62.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000   60.0000 61

#__ type_ start__ end____ width___ exp.time_
 24 omega -114.00  -57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -72.0000   92.0000 57

#__ type_ start__ end____ width___ exp.time_
 25 omega -114.00  -58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -71.0000  188.0000 56

#__ type_ start__ end____ width___ exp.time_
 26 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 27 omega -113.00  -59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -62.0000  348.0000 54

#__ type_ start__ end____ width___ exp.time_
 28 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 29 omega -113.00  -59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -62.0000  198.0000 54

#__ type_ start__ end____ width___ exp.time_
 30 omega -114.00  -58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -71.0000  271.0000 56

#__ type_ start__ end____ width___ exp.time_
 31 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 32 omega -115.00  -62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -45.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 33 omega -114.00  -60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -58.0000   42.0000 54

#__ type_ start__ end____ width___ exp.time_
 34 omega -114.00  -61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -55.0000   23.0000 53

#__ type_ start__ end____ width___ exp.time_
 35 omega -115.00  -62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -45.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 36 omega -114.00  -57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -76.0000   35.0000 57

#__ type_ start__ end____ width___ exp.time_
 37 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 38 omega -115.00  -59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -30.0000   18.0000 56

#__ type_ start__ end____ width___ exp.time_
 39 omega -178.00 -117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  120.0000 61

#__ type_ start__ end____ width___ exp.time_
 40 omega -114.00  -61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -52.0000  230.0000 53

#__ type_ start__ end____ width___ exp.time_
 41 omega -115.00  -62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -45.0000  300.0000 53

#__ type_ start__ end____ width___ exp.time_
 42 omega -115.00  -62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -45.0000  240.0000 53

#__ type_ start__ end____ width___ exp.time_
 43 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  300.0000 58

#__ type_ start__ end____ width___ exp.time_
 44 omega -114.00  -61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -55.0000  127.0000 53

#__ type_ start__ end____ width___ exp.time_
 45 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 46 omega -113.00  -58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -68.0000  278.0000 55

#__ type_ start__ end____ width___ exp.time_
 47 omega -114.00  -57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -75.0000  250.0000 57

#__ type_ start__ end____ width___ exp.time_
 48 omega -114.00  -55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -26.0000  259.0000 59

#__ type_ start__ end____ width___ exp.time_
 49 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 50 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  330.0000 58

#__ type_ start__ end____ width___ exp.time_
 51 omega -122.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  126.0000  194.0000 103

#__ type_ start__ end____ width___ exp.time_
 52 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  270.0000 58

#__ type_ start__ end____ width___ exp.time_
 53 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  180.0000 58

#__ type_ start__ end____ width___ exp.time_
 54 omega -114.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  210.0000 58

#__ type_ start__ end____ width___ exp.time_
 55 omega -114.00  -59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -67.0000  298.0000 55

#__ type_ start__ end____ width___ exp.time_
 56 omega   19.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 57 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 58 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  180.0000 58

#__ type_ start__ end____ width___ exp.time_
 59 omega  119.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   -9.0000  192.0000 58

#__ type_ start__ end____ width___ exp.time_
 60 omega   19.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 61 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  210.0000 58

#__ type_ start__ end____ width___ exp.time_
 62 omega   11.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -17.0000  172.0000 69

#__ type_ start__ end____ width___ exp.time_
 63 omega   15.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  330.0000 58

#__ type_ start__ end____ width___ exp.time_
 64 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 65 omega   12.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -18.0000  329.0000 68

#__ type_ start__ end____ width___ exp.time_
 66 omega   66.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 67 omega   62.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -12.0000  256.0000 59

#__ type_ start__ end____ width___ exp.time_
 68 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  300.0000 58

#__ type_ start__ end____ width___ exp.time_
 69 omega   69.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 70 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 71 omega   14.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   12.0000   68.0000 57

#__ type_ start__ end____ width___ exp.time_
 72 omega   19.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  330.0000 53

#__ type_ start__ end____ width___ exp.time_
 73 omega   66.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 74 omega  115.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  180.0000 53

#__ type_ start__ end____ width___ exp.time_
 75 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  270.0000 58

#__ type_ start__ end____ width___ exp.time_
 76 omega  115.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  330.0000 53

#__ type_ start__ end____ width___ exp.time_
 77 omega   70.00  123.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -54.0000  157.0000 53

#__ type_ start__ end____ width___ exp.time_
 78 omega    8.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   -9.0000  192.0000 59

#__ type_ start__ end____ width___ exp.time_
 79 omega   15.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 80 omega   69.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  270.0000 58

#__ type_ start__ end____ width___ exp.time_
 81 omega   68.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  180.0000 53

#__ type_ start__ end____ width___ exp.time_
 82 omega   68.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  300.0000 53

#__ type_ start__ end____ width___ exp.time_
 83 omega   19.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 84 omega   66.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  300.0000 53

#__ type_ start__ end____ width___ exp.time_
 85 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  330.0000 58

#__ type_ start__ end____ width___ exp.time_
 86 omega   66.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  210.0000 53

#__ type_ start__ end____ width___ exp.time_
 87 omega   66.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 88 omega  115.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 89 omega   57.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  111.0000 52

#__ type_ start__ end____ width___ exp.time_
 90 omega   66.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  270.0000 102

#__ type_ start__ end____ width___ exp.time_
 91 omega   66.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  240.0000 102

#__ type_ start__ end____ width___ exp.time_
 92 omega   69.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 93 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 94 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  240.0000 58

#__ type_ start__ end____ width___ exp.time_
 95 omega   68.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -87.0000  185.0000 62

#__ type_ start__ end____ width___ exp.time_
 96 omega   68.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000   34.0000 64

#__ type_ start__ end____ width___ exp.time_
 97 omega   57.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   24.0000  149.0000 60

#__ type_ start__ end____ width___ exp.time_
 98 omega   44.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   18.0000  211.0000 68

#__ type_ start__ end____ width___ exp.time_
 99 omega  118.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
100 omega    4.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
101 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  210.0000 177

#__ type_ start__ end____ width___ exp.time_
102 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  150.0000 177

#__ type_ start__ end____ width___ exp.time_
103 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  240.0000 177

#__ type_ start__ end____ width___ exp.time_
104 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  270.0000 177

#__ type_ start__ end____ width___ exp.time_
105 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  300.0000 177

#__ type_ start__ end____ width___ exp.time_
106 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000   30.0000 177

#__ type_ start__ end____ width___ exp.time_
107 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000   90.0000 177

#__ type_ start__ end____ width___ exp.time_
108 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  180.0000 177

#__ type_ start__ end____ width___ exp.time_
109 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  330.0000 177

#__ type_ start__ end____ width___ exp.time_
110 omega -178.00  -90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000   60.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1294776000
_diffrn_orient_matrix_UB_12      0.0415273000
_diffrn_orient_matrix_UB_13      0.0359460000
_diffrn_orient_matrix_UB_21      0.0617850000
_diffrn_orient_matrix_UB_22      -0.0206225000
_diffrn_orient_matrix_UB_23      0.0774762000
_diffrn_orient_matrix_UB_31      0.0409232000
_diffrn_orient_matrix_UB_32      0.1627182000
_diffrn_orient_matrix_UB_33      0.0006474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2922
_reflns_number_total             3017
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
K. Brandenburg Diamond - Crystal and Molecular Structure Visualization,
 Version  3.2i; Crystal Impact GbR: Bonn, Germany.
Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst (1997), 30, 565
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
L. Spek Single-crystal structure validation with the program PLATON J. Appl.
Crystallogr. 36 (2003) 7-13.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0533P)²+0.6504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B), C11(H11A,H11B), C7(H7A,H7B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C4(H4), C5(H5), C13(H13), C6(H6), C16(H16), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.29499(8) 0.82205(11) 0.05144(5) 0.0241(2) Uani 1 1 d . . .
H2 H 0.2750(17) 0.733(2) 0.0411(10) 0.039(5) Uiso 1 1 d . . .
O1 O 0.34387(9) 0.72009(10) 0.16809(5) 0.0266(2) Uani 1 1 d . . .
H1 H 0.379(2) 0.745(2) 0.2139(12) 0.058(6) Uiso 1 1 d . . .
O4 O 0.88097(9) 0.02250(11) 0.45221(6) 0.0350(3) Uani 1 1 d . . .
N2 N 0.55847(9) 0.59124(12) 0.37376(6) 0.0207(2) Uani 1 1 d . . .
O3 O 0.69420(9) -0.03987(10) 0.49542(5) 0.0300(2) Uani 1 1 d . . .
N1 N 0.43281(9) 0.82846(11) 0.29579(5) 0.0194(2) Uani 1 1 d . . .
N3 N 0.76627(10) 0.04811(12) 0.46318(6) 0.0233(3) Uani 1 1 d . . .
C17 C 0.74273(12) 0.42396(15) 0.38486(7) 0.0230(3) Uani 1 1 d . . .
H17 H 0.7981 0.4948 0.3632 0.028 Uiso 1 1 calc R . .
C15 C 0.71257(12) 0.18613(14) 0.43831(6) 0.0210(3) Uani 1 1 d . . .
C10 C 0.62711(12) 0.67959(15) 0.31854(8) 0.0266(3) Uani 1 1 d . . .
H10A H 0.6211 0.6301 0.2697 0.032 Uiso 1 1 calc R . .
H10B H 0.7198 0.6857 0.3328 0.032 Uiso 1 1 calc R . .
C12 C 0.60981(11) 0.45748(14) 0.39413(6) 0.0196(3) Uani 1 1 d . . .
C14 C 0.58164(12) 0.21432(14) 0.44770(6) 0.0216(3) Uani 1 1 d . . .
H14 H 0.5272 0.1420 0.4690 0.026 Uiso 1 1 calc R . .
C8 C 0.37053(12) 0.75793(14) 0.35899(7) 0.0220(3) Uani 1 1 d . . .
H8A H 0.2754 0.7585 0.3512 0.026 Uiso 1 1 calc R . .
H8B H 0.3903 0.8143 0.4047 0.026 Uiso 1 1 calc R . .
C4 C 0.50591(12) 1.27804(14) 0.16246(7) 0.0247(3) Uani 1 1 d . . .
H4 H 0.5430 1.3726 0.1694 0.030 Uiso 1 1 calc R . .
C5 C 0.48277(12) 1.22495(14) 0.09151(7) 0.0233(3) Uani 1 1 d . . .
H5 H 0.5029 1.2830 0.0494 0.028 Uiso 1 1 calc R . .
C13 C 0.53127(11) 0.34745(14) 0.42596(7) 0.0216(3) Uani 1 1 d . . .
H13 H 0.4416 0.3661 0.4325 0.026 Uiso 1 1 calc R . .
C6 C 0.42974(11) 1.08552(14) 0.08272(7) 0.0208(3) Uani 1 1 d . . .
H6 H 0.4143 1.0498 0.0339 0.025 Uiso 1 1 calc R . .
C2 C 0.41999(11) 1.05274(14) 0.21490(7) 0.0195(3) Uani 1 1 d . . .
C1 C 0.39808(11) 0.99547(13) 0.14288(7) 0.0189(3) Uani 1 1 d . . .
C11 C 0.57224(12) 0.83375(15) 0.31162(7) 0.0248(3) Uani 1 1 d . . .
H11A H 0.5881 0.8881 0.3584 0.030 Uiso 1 1 calc R . .
H11B H 0.6166 0.8866 0.2712 0.030 Uiso 1 1 calc R . .
C7 C 0.37637(12) 0.97545(14) 0.28458(7) 0.0219(3) Uani 1 1 d . . .
H7A H 0.3993 1.0374 0.3279 0.026 Uiso 1 1 calc R . .
H7B H 0.2808 0.9662 0.2828 0.026 Uiso 1 1 calc R . .
C9 C 0.41671(11) 0.60171(14) 0.36854(7) 0.0216(3) Uani 1 1 d . . .
H9A H 0.3787 0.5601 0.4141 0.026 Uiso 1 1 calc R . .
H9B H 0.3856 0.5423 0.3259 0.026 Uiso 1 1 calc R . .
C16 C 0.79287(12) 0.29069(15) 0.40669(7) 0.0237(3) Uani 1 1 d . . .
H16 H 0.8822 0.2702 0.4002 0.028 Uiso 1 1 calc R . .
C3 C 0.47454(12) 1.19221(14) 0.22333(7) 0.0233(3) Uani 1 1 d . . .
H3 H 0.4906 1.2292 0.2718 0.028 Uiso 1 1 calc R . .
B1 B 0.34236(12) 0.83653(16) 0.12243(8) 0.0199(3) 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
O2 H2 0.85(2) . ?
O2 B1 1.3714(16) . ?
O1 H1 0.93(2) . ?
O1 B1 1.3427(17) . ?
O4 N3 1.2255(14) . ?
N2 C10 1.4694(16) . ?
N2 C12 1.3766(16) . ?
N2 C9 1.4687(15) . ?
O3 N3 1.2429(15) . ?
N1 C8 1.4642(15) . ?
N1 C11 1.4651(15) . ?
N1 C7 1.4729(15) . ?
N3 C15 1.4431(16) . ?
C17 H17 0.9500 . ?
C17 C12 1.4179(17) . ?
C17 C16 1.3751(18) . ?
C15 C14 1.3885(18) . ?
C15 C16 1.3896(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5184(18) . ?
C12 C13 1.4152(17) . ?
C14 H14 0.9500 . ?
C14 C13 1.3744(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5095(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3861(18) . ?
C4 C3 1.3893(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3910(18) . ?
C13 H13 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.4020(17) . ?
C2 C1 1.4155(17) . ?
C2 C7 1.5140(17) . ?
C2 C3 1.3969(18) . ?
C1 B1 1.5990(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C16 H16 0.9500 . ?
C3 H3 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
B1 O2 H2 112.1(12) . . ?
B1 O1 H1 110.9(13) . . ?
C12 N2 C10 118.56(10) . . ?
C12 N2 C9 117.05(10) . . ?
C9 N2 C10 114.18(9) . . ?
C8 N1 C11 107.62(9) . . ?
C8 N1 C7 109.19(9) . . ?
C11 N1 C7 112.52(10) . . ?
O4 N3 O3 122.57(11) . . ?
O4 N3 C15 118.95(11) . . ?
O3 N3 C15 118.48(10) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C12 121.18(12) . . ?
C14 C15 N3 119.61(11) . . ?
C14 C15 C16 120.68(12) . . ?
C16 C15 N3 119.70(11) . . ?
N2 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
N2 C10 C11 112.30(10) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
N2 C12 C17 121.95(11) . . ?
N2 C12 C13 120.93(11) . . ?
C13 C12 C17 117.11(11) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 C15 119.59(12) . . ?
C13 C14 H14 120.2 . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C9 111.16(10) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.62(12) . . ?
C3 C4 H4 120.2 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.13(11) . . ?
C6 C5 H5 120.4 . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.57(11) . . ?
C14 C13 H13 119.2 . . ?
C5 C6 H6 118.6 . . ?
C5 C6 C1 122.74(11) . . ?
C1 C6 H6 118.6 . . ?
C1 C2 C7 123.02(11) . . ?
C3 C2 C1 119.64(11) . . ?
C3 C2 C7 117.13(11) . . ?
C6 C1 C2 117.30(11) . . ?
C6 C1 B1 115.95(10) . . ?
C2 C1 B1 126.74(11) . . ?
N1 C11 C10 110.51(10) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N1 C7 C2 114.53(10) . . ?
N1 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C2 C7 H7A 108.6 . . ?
C2 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N2 C9 C8 112.44(10) . . ?
N2 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C17 C16 C15 119.86(11) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C4 C3 C2 121.55(12) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
O2 B1 C1 115.19(11) . . ?
O1 B1 O2 119.88(12) . . ?
O1 B1 C1 124.88(11) . . ?

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
O4 N3 C15 C14 177.47(11) . . . . ?
O4 N3 C15 C16 -3.93(17) . . . . ?
N2 C10 C11 N1 -54.77(14) . . . . ?
N2 C12 C13 C14 -178.89(11) . . . . ?
O3 N3 C15 C14 -3.02(16) . . . . ?
O3 N3 C15 C16 175.59(11) . . . . ?
N1 C8 C9 N2 54.03(13) . . . . ?
N3 C15 C14 C13 178.13(10) . . . . ?
N3 C15 C16 C17 -178.15(11) . . . . ?
C17 C12 C13 C14 0.65(17) . . . . ?
C15 C14 C13 C12 -0.10(18) . . . . ?
C10 N2 C12 C17 22.07(17) . . . . ?
C10 N2 C12 C13 -158.41(11) . . . . ?
C10 N2 C9 C8 -45.09(14) . . . . ?
C12 N2 C10 C11 -170.18(10) . . . . ?
C12 N2 C9 C8 170.06(10) . . . . ?
C12 C17 C16 C15 0.15(18) . . . . ?
C14 C15 C16 C17 0.43(18) . . . . ?
C8 N1 C11 C10 62.76(13) . . . . ?
C8 N1 C7 C2 -172.54(10) . . . . ?
C4 C5 C6 C1 0.13(18) . . . . ?
C5 C4 C3 C2 0.05(18) . . . . ?
C5 C6 C1 C2 1.10(17) . . . . ?
C5 C6 C1 B1 -178.05(11) . . . . ?
C6 C1 B1 O2 -19.13(15) . . . . ?
C6 C1 B1 O1 158.32(12) . . . . ?
C2 C1 B1 O2 161.80(11) . . . . ?
C2 C1 B1 O1 -20.75(19) . . . . ?
C1 C2 C7 N1 60.42(15) . . . . ?
C1 C2 C3 C4 1.22(18) . . . . ?
C11 N1 C8 C9 -62.62(13) . . . . ?
C11 N1 C7 C2 68.04(13) . . . . ?
C7 N1 C8 C9 174.96(9) . . . . ?
C7 N1 C11 C10 -176.91(10) . . . . ?
C7 C2 C1 C6 172.77(10) . . . . ?
C7 C2 C1 B1 -8.18(18) . . . . ?
C7 C2 C3 C4 -173.61(11) . . . . ?
C9 N2 C10 C11 45.53(15) . . . . ?
C9 N2 C12 C17 165.35(11) . . . . ?
C9 N2 C12 C13 -15.13(16) . . . . ?
C16 C17 C12 N2 178.86(11) . . . . ?
C16 C17 C12 C13 -0.68(18) . . . . ?
C16 C15 C14 C13 -0.46(18) . . . . ?
C3 C4 C5 C6 -0.72(18) . . . . ?
C3 C2 C1 C6 -1.74(16) . . . . ?
C3 C2 C1 B1 177.31(11) . . . . ?
C3 C2 C7 N1 -124.94(11) . . . . ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(5)
_database_code_depnum_ccdc_archive 'CCDC 1040160'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
2-((4-methylpiperazin-1-yl)methyl)phenylboronic acid
;
_chemical_formula_moiety         'C12 H19 B N2 O2, H2 O'
_chemical_formula_sum            'C12 H21 B N2 O3'
_chemical_formula_weight         252.12
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y+1/2, z+1/2'
4 'x+1/2, -y+1/2, z'

_cell_length_a                   12.87751(17)
_cell_length_b                   10.18562(12)
_cell_length_c                   10.36536(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1359.58(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7344
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.1610
_cell_measurement_theta_min      4.2700
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10784
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.21
_diffrn_reflns_theta_min         5.54
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 0.8732
_diffrn_measured_fraction_theta_max 0.8864
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   11.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -10.5498   45.0000  180.0000 53

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   42.0000  286.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega   31.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498   77.0000  210.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.5498  -45.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
  5 omega -140.00 -100.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -90.0000  229.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega -138.00 -101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -99.0000  280.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega   15.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  270.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   60.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
  9 omega   69.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   60.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 11 omega  126.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   90.0000  130.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   15.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  240.0000 58

#__ type_ start__ end____ width___ exp.time_
 13 omega   69.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  285.0000 64

#__ type_ start__ end____ width___ exp.time_
 14 omega   79.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   99.0000   79.0000 51

#__ type_ start__ end____ width___ exp.time_
 15 omega   15.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  210.0000 58

#__ type_ start__ end____ width___ exp.time_
 16 omega  115.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 17 omega   89.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
 18 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  150.0000 177

#__ type_ start__ end____ width___ exp.time_
 19 omega -178.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000    0.0000  330.0000 177
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0321776000
_diffrn_orient_matrix_UB_12      0.1280510000
_diffrn_orient_matrix_UB_13      -0.0683472000
_diffrn_orient_matrix_UB_21      -0.1037735000
_diffrn_orient_matrix_UB_22      -0.0635309000
_diffrn_orient_matrix_UB_23      -0.0394988000
_diffrn_orient_matrix_UB_31      -0.0501154000
_diffrn_orient_matrix_UB_32      0.0494713000
_diffrn_orient_matrix_UB_33      0.1258872000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2143
_reflns_number_total             2186
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
K. Brandenburg Diamond - Crystal and Molecular Structure Visualization,
 Version  3.2i; Crystal Impact GbR: Bonn, Germany.
Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst (1997), 30, 565
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
L. Spek Single-crystal structure validation with the program PLATON J. Appl.
Crystallogr. 36 (2003) 7-13.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0762P)²+0.2887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C4(H4)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.26728(12) 0.56510(15) 0.59835(16) 0.0172(4) Uani 1 1 d . . .
N2 N 0.10711(12) 0.37154(15) 0.56245(16) 0.0181(4) Uani 1 1 d . . .
O2 O 0.46322(9) 0.79031(14) 0.29580(15) 0.0216(3) Uani 1 1 d . . .
H2 H 0.4205 0.8101 0.2378 0.026 Uiso 1 1 calc R . .
O1 O 0.30940(9) 0.70408(12) 0.38486(14) 0.0190(3) Uani 1 1 d . . .
H1 H 0.2893 0.6663 0.4524 0.023 Uiso 1 1 calc R . .
C2 C 0.45447(14) 0.62343(17) 0.62399(19) 0.0183(4) Uani 1 1 d . . .
C7 C 0.34397(15) 0.64136(18) 0.67334(19) 0.0194(4) Uani 1 1 d . . .
H7A H 0.3408 0.6137 0.7648 0.023 Uiso 1 1 calc R . .
H7B H 0.3255 0.7356 0.6693 0.023 Uiso 1 1 calc R . .
C8 C 0.16194(14) 0.58401(18) 0.6513(2) 0.0194(4) Uani 1 1 d . . .
H8A H 0.1452 0.6788 0.6544 0.023 Uiso 1 1 calc R . .
H8B H 0.1586 0.5489 0.7403 0.023 Uiso 1 1 calc R . .
C12 C 0.03222(15) 0.3016(2) 0.4804(2) 0.0259(5) Uani 1 1 d . . .
H12A H 0.0373 0.3345 0.3918 0.039 Uiso 1 1 calc R . .
H12B H -0.0382 0.3163 0.5131 0.039 Uiso 1 1 calc R . .
H12C H 0.0477 0.2074 0.4816 0.039 Uiso 1 1 calc R . .
C3 C 0.52593(15) 0.56761(19) 0.7085(2) 0.0232(5) Uani 1 1 d . . .
H3 H 0.5046 0.5461 0.7937 0.028 Uiso 1 1 calc R . .
C5 C 0.65937(15) 0.57546(18) 0.5475(2) 0.0214(4) Uani 1 1 d . . .
H5 H 0.7283 0.5574 0.5201 0.026 Uiso 1 1 calc R . .
B1 B 0.41416(15) 0.72143(18) 0.3897(2) 0.0168(4) Uani 1 1 d . . .
C10 C 0.21299(14) 0.35099(18) 0.5145(2) 0.0204(4) Uani 1 1 d . . .
H10A H 0.2179 0.3823 0.4242 0.025 Uiso 1 1 calc R . .
H10B H 0.2293 0.2560 0.5154 0.025 Uiso 1 1 calc R . .
C11 C 0.29106(14) 0.42405(18) 0.5971(2) 0.0211(4) Uani 1 1 d . . .
H11A H 0.2891 0.3894 0.6863 0.025 Uiso 1 1 calc R . .
H11B H 0.3619 0.4101 0.5625 0.025 Uiso 1 1 calc R . .
C6 C 0.58954(14) 0.63486(17) 0.4643(2) 0.0182(4) Uani 1 1 d . . .
H6 H 0.6125 0.6598 0.3808 0.022 Uiso 1 1 calc R . .
C1 C 0.48557(13) 0.65953(17) 0.49933(19) 0.0174(4) Uani 1 1 d . . .
C9 C 0.08371(13) 0.51290(18) 0.56623(19) 0.0194(4) Uani 1 1 d . . .
H9A H 0.0128 0.5265 0.6006 0.023 Uiso 1 1 calc R . .
H9B H 0.0863 0.5494 0.4778 0.023 Uiso 1 1 calc R . .
C4 C 0.62778(15) 0.54257(19) 0.6712(2) 0.0257(5) Uani 1 1 d . . .
H4 H 0.6752 0.5033 0.7299 0.031 Uiso 1 1 calc R . .
O3 O 0.34697(15) 0.1086(2) 0.7087(2) 0.0505(5) Uani 1 1 d G . .
H3A H 0.2943 0.1358 0.7504 0.076 Uiso 1 1 d G . .
H3B H 0.4020 0.1296 0.7490 0.076 Uiso 1 1 d G . .


_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 C7 1.477(2) . ?
N1 C8 1.476(2) . ?
N1 C11 1.469(2) . ?
N2 C12 1.470(2) . ?
N2 C10 1.466(2) . ?
N2 C9 1.472(2) . ?
O2 H2 0.8400 . ?
O2 B1 1.356(3) . ?
O1 H1 0.8400 . ?
O1 B1 1.362(2) . ?
C2 C7 1.523(3) . ?
C2 C3 1.392(3) . ?
C2 C1 1.402(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.522(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C5 C4 1.386(3) . ?
B1 C1 1.592(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.516(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C1 1.410(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 H4 0.9500 . ?
O3 H3A 0.8514 . ?
O3 H3B 0.8500 . ?

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
C8 N1 C7 110.49(15) . . ?
C11 N1 C7 112.30(14) . . ?
C11 N1 C8 108.81(13) . . ?
C12 N2 C9 110.79(15) . . ?
C10 N2 C12 110.16(15) . . ?
C10 N2 C9 109.83(13) . . ?
B1 O2 H2 109.5 . . ?
B1 O1 H1 109.5 . . ?
C3 C2 C7 117.07(17) . . ?
C3 C2 C1 119.90(17) . . ?
C1 C2 C7 123.03(16) . . ?
N1 C7 C2 112.63(15) . . ?
N1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C2 C7 H7A 109.1 . . ?
C2 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
N1 C8 C9 109.31(16) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.40(18) . . ?
C4 C5 H5 120.3 . . ?
O2 B1 O1 120.13(18) . . ?
O2 B1 C1 116.63(16) . . ?
O1 B1 C1 123.20(17) . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 C11 110.78(15) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
N1 C11 C10 110.29(15) . . ?
N1 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C1 122.29(19) . . ?
C1 C6 H6 118.9 . . ?
C2 C1 B1 126.63(16) . . ?
C2 C1 C6 117.50(17) . . ?
C6 C1 B1 115.83(17) . . ?
N2 C9 C8 110.21(14) . . ?
N2 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.32(18) . . ?
C5 C4 H4 120.3 . . ?
H3A O3 H3B 109.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C9 N2 60.20(19) . . . . ?
N2 C10 C11 N1 -58.4(2) . . . . ?
O2 B1 C1 C2 157.56(17) . . . . ?
O2 B1 C1 C6 -24.8(2) . . . . ?
O1 B1 C1 C2 -24.8(3) . . . . ?
O1 B1 C1 C6 152.79(17) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C7 N1 C8 C9 175.72(15) . . . . ?
C7 N1 C11 C10 -177.60(15) . . . . ?
C7 C2 C3 C4 177.57(17) . . . . ?
C7 C2 C1 B1 -0.9(3) . . . . ?
C7 C2 C1 C6 -178.49(16) . . . . ?
C8 N1 C7 C2 179.03(14) . . . . ?
C8 N1 C11 C10 59.8(2) . . . . ?
C12 N2 C10 C11 179.23(16) . . . . ?
C12 N2 C9 C8 -179.90(16) . . . . ?
C3 C2 C7 N1 -117.80(18) . . . . ?
C3 C2 C1 B1 178.64(17) . . . . ?
C3 C2 C1 C6 1.1(2) . . . . ?
C5 C6 C1 C2 1.0(3) . . . . ?
C5 C6 C1 B1 -176.83(16) . . . . ?
C10 N2 C9 C8 -58.0(2) . . . . ?
C11 N1 C7 C2 57.3(2) . . . . ?
C11 N1 C8 C9 -60.56(19) . . . . ?
C6 C5 C4 C3 1.2(3) . . . . ?
C1 C2 C7 N1 61.8(2) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
C9 N2 C10 C11 56.93(19) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(6)
_database_code_depnum_ccdc_archive 'CCDC 1040161'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
2-((4-benzhydrylpiperazin-1-yl)methyl)phenylboronic acid
;
_chemical_formula_moiety         'C24 H27 B N2 O2, C3 H6 O'
_chemical_formula_sum            'C27 H33 B N2 O3'
_chemical_formula_weight         444.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   24.60371(16)
_cell_length_b                   11.76829(7)
_cell_length_c                   17.52165(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.8287(6)
_cell_angle_gamma                90.00
_cell_volume                     5061.96(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    92982
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.0174
_cell_measurement_theta_min      3.2049
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            161927
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.50
_diffrn_reflns_theta_min         3.60
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.3347
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -34.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.9488  -77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.9488  -77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   16.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488   37.0000  -30.0000 99

#__ type_ start__ end____ width___ exp.time_
  4 omega   25.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488   37.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega  -32.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488  -49.0000   14.0000 100

#__ type_ start__ end____ width___ exp.time_
  6 omega   15.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488 -125.0000  -90.0000 80

#__ type_ start__ end____ width___ exp.time_
  7 omega   13.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.9488   49.0000  165.0000 102

#__ type_ start__ end____ width___ exp.time_
  8 omega  -37.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.0000  -84.0000  154.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega  -39.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.0000  -81.0000 -132.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega  -39.00  -13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -50.0000  -88.0000  179.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  -44.00  -17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -50.0000  -84.0000   57.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega  -44.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -52.0000  -84.0000  -38.0000 28

#__ type_ start__ end____ width___ exp.time_
 13 omega  -45.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -54.0000  -84.0000   39.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega  -45.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -54.0000  -84.0000 -115.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  -45.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -54.0000  -84.0000  113.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega  -47.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.0000  -82.0000  -69.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega  -47.00  -22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.0000  -82.0000  -27.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega  -46.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.0000  -84.0000 -158.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega  -57.00  -30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -79.0000 -126.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega  -56.00  -30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -79.0000 -104.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   32.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   79.0000   36.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  -68.00  -34.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -68.0000  -77.0000   91.0000 34

#__ type_ start__ end____ width___ exp.time_
 23 omega  -63.00  -37.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -79.0000  167.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   36.00   63.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   76.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega -128.00 -101.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -79.0000  -49.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega  -61.00  -36.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -79.0000  -49.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega -140.00 -113.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -79.0000  167.0000 27

#__ type_ start__ end____ width___ exp.time_
 28 omega  -62.00  -36.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -79.0000   69.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega  -64.00  -38.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -72.0000  -77.0000 -167.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega  -66.00  -40.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -72.0000  -75.0000  -23.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega -126.00  -99.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -72.0000  -75.0000  -23.0000 27

#__ type_ start__ end____ width___ exp.time_
 32 omega  -63.00  -38.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -72.0000  -77.0000   28.0000 25

#__ type_ start__ end____ width___ exp.time_
 33 omega  -66.00  -40.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -77.0000  144.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega  -69.00  -43.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -76.0000  -75.0000 -179.0000 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   42.00   68.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   79.0000   41.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega  -68.00  -42.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -76.0000  -79.0000  132.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega  -71.00  -45.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -75.0000 -144.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega  -72.00  -46.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -80.0000  -79.0000 -121.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega  -73.00  -47.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -80.0000  -73.0000  -84.0000 26

#__ type_ start__ end____ width___ exp.time_
 40 omega  -90.00  -48.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -82.0000  -77.0000   87.0000 42

#__ type_ start__ end____ width___ exp.time_
 41 omega  -74.00  -48.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -82.0000  -77.0000  -52.0000 26

#__ type_ start__ end____ width___ exp.time_
 42 omega  -74.00  -48.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -82.0000  -77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 43 omega  -74.00  -48.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -82.0000  -77.0000  -23.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega  -75.00  -49.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -82.0000  -73.0000  170.0000 26

#__ type_ start__ end____ width___ exp.time_
 45 omega  -77.00  -51.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -84.0000  -77.0000  123.0000 26

#__ type_ start__ end____ width___ exp.time_
 46 omega  -78.00  -52.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -86.0000  -79.0000   67.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega  -79.00  -53.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -86.0000  -73.0000 -103.0000 26

#__ type_ start__ end____ width___ exp.time_
 48 omega  -80.00  -54.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -88.0000  -79.0000   13.0000 26

#__ type_ start__ end____ width___ exp.time_
 49 omega  -82.00  -56.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 50 omega -119.00  -87.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 51 omega  -83.00  -58.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -71.0000  148.0000 25

#__ type_ start__ end____ width___ exp.time_
 52 omega  -82.00  -57.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -73.0000 -151.0000 25

#__ type_ start__ end____ width___ exp.time_
 53 omega  -83.00  -57.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -75.0000   37.0000 26

#__ type_ start__ end____ width___ exp.time_
 54 omega  -84.00  -56.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000   84.0000 28

#__ type_ start__ end____ width___ exp.time_
 55 omega  -84.00  -58.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -75.0000   51.0000 26

#__ type_ start__ end____ width___ exp.time_
 56 omega  -86.00  -59.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -69.0000  -65.0000 27

#__ type_ start__ end____ width___ exp.time_
 57 omega -119.00  -93.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 58 omega  -81.00  -56.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 59 omega  -82.00  -56.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 60 omega   33.00   75.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -18.0000   93.0000 42

#__ type_ start__ end____ width___ exp.time_
 61 omega   11.00   62.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 62 omega   86.00  124.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -67.0000   27.0000 38

#__ type_ start__ end____ width___ exp.time_
 63 omega   70.00  103.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 64 omega   19.00   78.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -67.0000   27.0000 59

#__ type_ start__ end____ width___ exp.time_
 65 omega   71.00  114.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -64.0000 43

#__ type_ start__ end____ width___ exp.time_
 66 omega   33.00   68.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -64.0000 35

#__ type_ start__ end____ width___ exp.time_
 67 omega   69.00   95.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 68 omega   46.00   78.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -21.0000  -73.0000 32

#__ type_ start__ end____ width___ exp.time_
 69 omega   13.00   42.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -21.0000  -73.0000 29

#__ type_ start__ end____ width___ exp.time_
 70 omega  111.00  158.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 71 omega   77.00  102.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 72 omega  143.00  169.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   22.0000   86.0000 26

#__ type_ start__ end____ width___ exp.time_
 73 omega   55.00  125.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   22.0000   86.0000 70

#__ type_ start__ end____ width___ exp.time_
 74 omega  127.00  153.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 75 omega   58.00  138.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   23.0000   24.0000 80

#__ type_ start__ end____ width___ exp.time_
 76 omega   57.00  143.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   24.0000  -40.0000 86

#__ type_ start__ end____ width___ exp.time_
 77 omega   73.00  115.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
 78 omega  100.00  126.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 79 omega   89.00  133.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  178.0000 44

#__ type_ start__ end____ width___ exp.time_
 80 omega   34.00   61.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  178.0000 27

#__ type_ start__ end____ width___ exp.time_
 81 omega   30.00   56.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 82 omega   97.00  123.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000   23.0000 26

#__ type_ start__ end____ width___ exp.time_
 83 omega   37.00   79.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000   23.0000 42

#__ type_ start__ end____ width___ exp.time_
 84 omega  141.00  166.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 85 omega   61.00  109.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 86 omega   98.00  130.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -32.0000 32

#__ type_ start__ end____ width___ exp.time_
 87 omega   15.00   75.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -32.0000 60

#__ type_ start__ end____ width___ exp.time_
 88 omega  110.00  171.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
 89 omega   60.00   86.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 90 omega   29.00  114.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  113.0000 85

#__ type_ start__ end____ width___ exp.time_
 91 omega  126.00  159.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 92 omega   60.00  105.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
 93 omega   60.00   91.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
 94 omega  124.00  171.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
 95 omega  139.00  170.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
 96 omega   60.00  106.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 97 omega  112.00  170.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 98 omega   60.00   85.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 99 omega  146.00  171.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
100 omega   60.00  109.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
101 omega   68.00  132.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
102 omega   61.00   86.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
103 omega  116.00  171.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
104 omega   60.00   89.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
105 omega  120.00  145.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
106 omega   70.00   96.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
107 omega  129.00  154.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
108 omega   74.00   99.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
109 omega  117.00  145.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
110 omega   60.00  105.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
111 omega  142.00  171.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
112 omega   60.00   94.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
113 omega   70.00  103.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
114 omega  120.00  156.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
115 omega  146.00  172.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
116 omega   80.00  116.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   49.0000  -18.0000 36

#__ type_ start__ end____ width___ exp.time_
117 omega  137.00  162.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   49.0000  -18.0000 25

#__ type_ start__ end____ width___ exp.time_
118 omega  105.00  131.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
119 omega   60.00   93.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
120 omega   76.00  167.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
121 omega   84.00  151.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  -30.0000 67

#__ type_ start__ end____ width___ exp.time_
122 omega  116.00  142.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
123 omega   34.00   65.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
124 omega  113.00  153.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
125 omega   43.00   68.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
126 omega   99.00  144.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
127 omega   44.00   88.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -53.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
128 omega   44.00   75.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
129 omega  125.00  156.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
130 omega   56.00   89.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -56.0000   22.0000 33

#__ type_ start__ end____ width___ exp.time_
131 omega   32.00   72.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
132 omega   23.00   49.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -56.0000   22.0000 26

#__ type_ start__ end____ width___ exp.time_
133 omega   21.00   56.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
134 omega   70.00  125.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
135 omega   95.00  122.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
136 omega   19.00   70.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
137 omega   81.00  106.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -18.0000   93.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0333804141
_diffrn_orient_matrix_UB_12      0.1209151251
_diffrn_orient_matrix_UB_13      -0.0014549776
_diffrn_orient_matrix_UB_21      0.0606377145
_diffrn_orient_matrix_UB_22      -0.0412517022
_diffrn_orient_matrix_UB_23      -0.0379427456
_diffrn_orient_matrix_UB_31      -0.0545498747
_diffrn_orient_matrix_UB_32      0.0280909204
_diffrn_orient_matrix_UB_33      -0.0499437003
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                8238
_reflns_number_total             8915
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
K. Brandenburg Diamond - Crystal and Molecular Structure Visualization,
 Version  3.2i; Crystal Impact GbR: Bonn, Germany.
Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst (1997), 30, 565
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
L. Spek Single-crystal structure validation with the program PLATON J. Appl.
Crystallogr. 36 (2003) 7-13.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.00023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         8915
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0397P)²+1.8387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C43-C42 ∼ C63-C42
 with sigma of 0.01
 C44-C43 ∼ C45-C44 ∼ C46-C45 ∼ C47-C46 ∼ C68-C47 ∼ C68-C43
 ∼ C64-C63 ∼ C65-C64
 ∼ C66-C65 ∼ C67-C66 ∼ C74-C67 ∼ C74-C63
 with sigma of 0.002
3. Restrained planarity
 C63, C74, C67, C66, C65, C64
 with sigma of 0.1
 C43, C68, C47, C46, C45, C44
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C63) = Uanis(C43)
Uanis(C64) = Uanis(C44)
Uanis(C65) = Uanis(C45)
Uanis(C66) = Uanis(C46)
Uanis(C67) = Uanis(C47)
Uanis(C74) = Uanis(C68)
5. Others
 Sof(H42A)=Sof(C43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=
 Sof(C47)=Sof(H47)=Sof(C68)=Sof(H68)=1-FVAR(1)
 Sof(H42)=Sof(C63)=Sof(C64)=Sof(H64)=Sof(C65)=Sof(H65)=Sof(C66)=Sof(H66)=
 Sof(C67)=Sof(H67)=Sof(C74)=Sof(H74)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C12(H12), C42(H42), C42(H42A)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C33(H33), C34(H34),
  C35(H35), C36(H36), C44(H44), C45(H45), C46(H46), C47(H47), C50(H50),
 C51(H51), C52(H52), C53(H53), C54(H54), C64(H64), C65(H65), C66(H66), C67(H67),
  C68(H68), C74(H74)
6.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C55(H55A,H55B,H55C), C57(H57A,H57B,
 H57C)
6.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20326(3) 0.59866(7) 0.55803(5) 0.0323(2) Uani 1 1 d . . .
H1 H 0.1753 0.6109 0.5819 0.048 Uiso 1 1 calc R . .
O2 O 0.28969(3) 0.67796(8) 0.54352(6) 0.0398(2) Uani 1 1 d . . .
H2 H 0.2920 0.6180 0.5179 0.060 Uiso 1 1 calc R . .
O3 O 0.30022(3) 0.49004(7) 0.45312(5) 0.03098(19) Uani 1 1 d . . .
H3 H 0.3281 0.4752 0.4299 0.046 Uiso 1 1 calc R . .
O4 O 0.21350(3) 0.41246(8) 0.47056(6) 0.0400(2) Uani 1 1 d . . .
H4 H 0.2119 0.4726 0.4961 0.060 Uiso 1 1 calc R . .
O5 O 0.38666(5) 0.88944(12) 0.35924(8) 0.0741(4) Uani 1 1 d . . .
O6 O 0.89173(4) 0.89535(11) 0.39778(7) 0.0666(4) Uani 1 1 d . . .
N1 N 0.11698(4) 0.65328(8) 0.62636(5) 0.0227(2) Uani 1 1 d . . .
N2 N 0.05327(4) 0.46716(8) 0.68074(5) 0.0240(2) Uani 1 1 d . . .
N3 N 0.38914(4) 0.41659(8) 0.39340(5) 0.0232(2) Uani 1 1 d . . .
N4 N 0.46186(4) 0.57273(8) 0.32453(5) 0.0238(2) Uani 1 1 d . A .
C1 C 0.22944(5) 0.78662(10) 0.62810(7) 0.0282(3) Uani 1 1 d . . .
C2 C 0.17781(5) 0.82345(10) 0.64931(6) 0.0251(2) Uani 1 1 d . . .
C3 C 0.17424(5) 0.91259(10) 0.70087(7) 0.0305(3) Uani 1 1 d . . .
H3A H 0.1395 0.9351 0.7160 0.037 Uiso 1 1 calc R . .
C4 C 0.22014(6) 0.96926(11) 0.73062(8) 0.0392(3) Uani 1 1 d . . .
H4A H 0.2170 1.0298 0.7659 0.047 Uiso 1 1 calc R . .
C5 C 0.27062(6) 0.93677(12) 0.70844(9) 0.0436(3) Uani 1 1 d . . .
H5 H 0.3024 0.9764 0.7274 0.052 Uiso 1 1 calc R . .
C6 C 0.27502(5) 0.84658(11) 0.65869(8) 0.0370(3) Uani 1 1 d . . .
H6 H 0.3102 0.8245 0.6448 0.044 Uiso 1 1 calc R . .
C7 C 0.12463(4) 0.77614(10) 0.61400(7) 0.0259(2) Uani 1 1 d . . .
H7A H 0.0941 0.8176 0.6355 0.031 Uiso 1 1 calc R . .
H7B H 0.1228 0.7910 0.5583 0.031 Uiso 1 1 calc R . .
C8 C 0.06590(4) 0.61472(10) 0.58562(6) 0.0263(2) Uani 1 1 d . . .
H8A H 0.0676 0.6290 0.5302 0.032 Uiso 1 1 calc R . .
H8B H 0.0350 0.6587 0.6037 0.032 Uiso 1 1 calc R . .
C9 C 0.05657(5) 0.48930(10) 0.59885(6) 0.0259(2) Uani 1 1 d . . .
H9A H 0.0223 0.4651 0.5707 0.031 Uiso 1 1 calc R . .
H9B H 0.0869 0.4449 0.5793 0.031 Uiso 1 1 calc R . .
C10 C 0.10528(5) 0.50171(10) 0.71942(6) 0.0262(2) Uani 1 1 d . . .
H10A H 0.1353 0.4579 0.6986 0.031 Uiso 1 1 calc R . .
H10B H 0.1050 0.4848 0.7747 0.031 Uiso 1 1 calc R . .
C11 C 0.11489(5) 0.62731(10) 0.70823(6) 0.0256(2) Uani 1 1 d . . .
H11A H 0.0852 0.6713 0.7296 0.031 Uiso 1 1 calc R . .
H11B H 0.1496 0.6498 0.7358 0.031 Uiso 1 1 calc R . .
C12 C 0.04036(5) 0.34682(10) 0.69504(6) 0.0254(2) Uani 1 1 d . . .
H12 H 0.0680 0.2985 0.6711 0.030 Uiso 1 1 calc R . .
C13 C -0.01577(5) 0.31564(10) 0.65921(6) 0.0251(2) Uani 1 1 d . . .
C14 C -0.02454(5) 0.20685(10) 0.62981(6) 0.0285(3) Uani 1 1 d . . .
H14 H 0.0050 0.1548 0.6295 0.034 Uiso 1 1 calc R . .
C15 C -0.07606(5) 0.17368(11) 0.60082(7) 0.0328(3) Uani 1 1 d . . .
H15 H -0.0817 0.0989 0.5816 0.039 Uiso 1 1 calc R . .
C16 C -0.11908(5) 0.24926(12) 0.59993(7) 0.0340(3) Uani 1 1 d . . .
H16 H -0.1543 0.2264 0.5804 0.041 Uiso 1 1 calc R . .
C17 C -0.11057(5) 0.35871(12) 0.62761(7) 0.0329(3) Uani 1 1 d . . .
H17 H -0.1399 0.4113 0.6262 0.040 Uiso 1 1 calc R . .
C18 C -0.05930(5) 0.39163(11) 0.65742(7) 0.0293(3) Uani 1 1 d . . .
H18 H -0.0538 0.4665 0.6767 0.035 Uiso 1 1 calc R . .
C19 C 0.04358(5) 0.32269(10) 0.78076(7) 0.0283(3) Uani 1 1 d . . .
C20 C 0.07504(5) 0.23323(11) 0.81082(7) 0.0346(3) Uani 1 1 d . . .
H20 H 0.0933 0.1849 0.7775 0.042 Uiso 1 1 calc R . .
C21 C 0.07999(5) 0.21377(13) 0.88943(8) 0.0440(4) Uani 1 1 d . . .
H21 H 0.1016 0.1523 0.9094 0.053 Uiso 1 1 calc R . .
C22 C 0.05370(6) 0.28338(14) 0.93831(8) 0.0459(4) Uani 1 1 d . . .
H22 H 0.0575 0.2707 0.9919 0.055 Uiso 1 1 calc R . .
C23 C 0.02169(6) 0.37206(13) 0.90892(7) 0.0425(3) Uani 1 1 d . . .
H23 H 0.0033 0.4199 0.9425 0.051 Uiso 1 1 calc R . .
C24 C 0.01632(5) 0.39130(11) 0.83060(7) 0.0334(3) Uani 1 1 d . . .
H24 H -0.0061 0.4516 0.8108 0.040 Uiso 1 1 calc R . .
C25 C 0.29829(10) 0.80688(16) 0.35399(12) 0.0761(6) Uani 1 1 d . . .
H25A H 0.3065 0.7846 0.3021 0.114 Uiso 1 1 calc R . .
H25B H 0.2643 0.8505 0.3519 0.114 Uiso 1 1 calc R . .
H25C H 0.2943 0.7387 0.3852 0.114 Uiso 1 1 calc R . .
C26 C 0.34359(7) 0.87816(13) 0.38865(9) 0.0496(4) Uani 1 1 d . . .
C27 C 0.33428(7) 0.93409(14) 0.46254(9) 0.0505(4) Uani 1 1 d . . .
H27A H 0.3667 0.9777 0.4799 0.076 Uiso 1 1 calc R . .
H27B H 0.3270 0.8762 0.5007 0.076 Uiso 1 1 calc R . .
H27C H 0.3029 0.9853 0.4558 0.076 Uiso 1 1 calc R . .
C31 C 0.27442(5) 0.29529(10) 0.39259(6) 0.0283(3) Uani 1 1 d . . .
C32 C 0.32635(5) 0.25085(10) 0.38007(6) 0.0267(2) Uani 1 1 d . . .
C33 C 0.33106(5) 0.15810(11) 0.33180(7) 0.0338(3) Uani 1 1 d . . .
H33 H 0.3662 0.1295 0.3232 0.041 Uiso 1 1 calc R . .
C34 C 0.28574(6) 0.10666(12) 0.29614(7) 0.0401(3) Uani 1 1 d . . .
H34 H 0.2898 0.0440 0.2628 0.048 Uiso 1 1 calc R . .
C35 C 0.23448(6) 0.14699(13) 0.30938(8) 0.0416(3) Uani 1 1 d . . .
H35 H 0.2030 0.1112 0.2860 0.050 Uiso 1 1 calc R . .
C36 C 0.22920(5) 0.23993(12) 0.35685(7) 0.0357(3) Uani 1 1 d . . .
H36 H 0.1937 0.2670 0.3654 0.043 Uiso 1 1 calc R . .
C37 C 0.37791(5) 0.29975(10) 0.41893(6) 0.0273(2) Uani 1 1 d . . .
H37A H 0.3747 0.3000 0.4749 0.033 Uiso 1 1 calc R . .
H37B H 0.4090 0.2503 0.4081 0.033 Uiso 1 1 calc R . .
C38 C 0.43873(4) 0.46042(10) 0.43517(6) 0.0268(2) Uani 1 1 d . . .
H38A H 0.4694 0.4076 0.4285 0.032 Uiso 1 1 calc R . .
H38B H 0.4328 0.4646 0.4904 0.032 Uiso 1 1 calc R . .
C39 C 0.45314(4) 0.57705(10) 0.40644(6) 0.0263(2) Uani 1 1 d . . .
H39A H 0.4233 0.6309 0.4154 0.032 Uiso 1 1 calc R . .
H39B H 0.4866 0.6047 0.4350 0.032 Uiso 1 1 calc R . .
C40 C 0.41061(4) 0.53620(10) 0.28493(6) 0.0247(2) Uani 1 1 d . . .
H40A H 0.4141 0.5366 0.2290 0.030 Uiso 1 1 calc R . .
H40B H 0.3811 0.5894 0.2964 0.030 Uiso 1 1 calc R . .
C41 C 0.39679(4) 0.41805(10) 0.31086(6) 0.0242(2) Uani 1 1 d . . .
H41A H 0.3630 0.3918 0.2824 0.029 Uiso 1 1 calc R . .
H41B H 0.4265 0.3652 0.2996 0.029 Uiso 1 1 calc R . .
C42 C 0.48108(5) 0.68353(10) 0.29784(7) 0.0285(3) Uani 1 1 d D . .
H42 H 0.4546 0.7416 0.3142 0.034 Uiso 0.492(2) 1 calc PR A 1
H42A H 0.4582 0.7458 0.3175 0.034 Uiso 0.508(2) 1 calc PR A 2
C43 C 0.5409(3) 0.6968(5) 0.3310(11) 0.0328(7) Uani 0.508(2) 1 d PD A 2
C44 C 0.56249(13) 0.8025(3) 0.3528(3) 0.0360(8) Uani 0.508(2) 1 d PD A 2
H44 H 0.5389 0.8665 0.3504 0.043 Uiso 0.508(2) 1 calc PR A 2
C45 C 0.61680(13) 0.8186(3) 0.3778(2) 0.0470(9) Uani 0.508(2) 1 d PD A 2
H45 H 0.6298 0.8927 0.3905 0.056 Uiso 0.508(2) 1 calc PR A 2
C46 C 0.65196(14) 0.7261(3) 0.3843(2) 0.0525(11) Uani 0.508(2) 1 d PD A 2
H46 H 0.6893 0.7365 0.4003 0.063 Uiso 0.508(2) 1 calc PR A 2
C47 C 0.63169(16) 0.6180(3) 0.3669(2) 0.0433(8) Uani 0.508(2) 1 d PD A 2
H47 H 0.6547 0.5533 0.3725 0.052 Uiso 0.508(2) 1 calc PR A 2
C49 C 0.47815(5) 0.68638(10) 0.21064(7) 0.0280(3) Uani 1 1 d . A .
C50 C 0.50848(5) 0.61157(11) 0.16897(7) 0.0303(3) Uani 1 1 d . . .
H50 H 0.5338 0.5617 0.1950 0.036 Uiso 1 1 calc R A .
C51 C 0.50200(5) 0.60930(12) 0.08954(7) 0.0355(3) Uani 1 1 d . A .
H51 H 0.5228 0.5577 0.0616 0.043 Uiso 1 1 calc R . .
C52 C 0.46538(6) 0.68186(12) 0.05099(7) 0.0403(3) Uani 1 1 d . . .
H52 H 0.4609 0.6800 -0.0033 0.048 Uiso 1 1 calc R A .
C53 C 0.43536(6) 0.75694(12) 0.09183(8) 0.0423(3) Uani 1 1 d . A .
H53 H 0.4102 0.8070 0.0656 0.051 Uiso 1 1 calc R . .
C54 C 0.44184(5) 0.75948(11) 0.17119(8) 0.0350(3) Uani 1 1 d . . .
H54 H 0.4212 0.8118 0.1988 0.042 Uiso 1 1 calc R A .
C55 C 0.81226(8) 0.78453(15) 0.38172(11) 0.0643(5) Uani 1 1 d . . .
H55A H 0.8302 0.7534 0.3380 0.096 Uiso 1 1 calc R . .
H55B H 0.7766 0.8155 0.3641 0.096 Uiso 1 1 calc R . .
H55C H 0.8074 0.7241 0.4192 0.096 Uiso 1 1 calc R . .
C56 C 0.84627(6) 0.87590(14) 0.41767(9) 0.0481(4) Uani 1 1 d . . .
C57 C 0.82188(7) 0.94264(15) 0.47930(9) 0.0560(4) Uani 1 1 d . . .
H57A H 0.8493 0.9945 0.5028 0.084 Uiso 1 1 calc R . .
H57B H 0.8095 0.8906 0.5182 0.084 Uiso 1 1 calc R . .
H57C H 0.7908 0.9866 0.4573 0.084 Uiso 1 1 calc R . .
C63 C 0.5359(3) 0.7175(5) 0.3331(11) 0.0328(7) Uani 0.492(2) 1 d PD A 1
C64 C 0.54205(13) 0.8304(3) 0.3558(3) 0.0360(8) Uani 0.492(2) 1 d PD A 1
H64 H 0.5121 0.8814 0.3515 0.043 Uiso 0.492(2) 1 calc PR A 1
C65 C 0.59308(12) 0.8666(3) 0.3850(2) 0.0470(9) Uani 0.492(2) 1 d PD A 1
H65 H 0.5984 0.9426 0.4022 0.056 Uiso 0.492(2) 1 calc PR A 1
C66 C 0.63625(14) 0.7900(3) 0.3887(2) 0.0525(11) Uani 0.492(2) 1 d PD A 1
H66 H 0.6713 0.8149 0.4076 0.063 Uiso 0.492(2) 1 calc PR A 1
C67 C 0.62910(18) 0.6778(3) 0.3654(2) 0.0433(8) Uani 0.492(2) 1 d PD A 1
H67 H 0.6592 0.6271 0.3688 0.052 Uiso 0.492(2) 1 calc PR A 1
C68 C 0.5771(2) 0.6062(5) 0.3413(8) 0.0416(13) Uani 0.508(2) 1 d PD A 2
H68 H 0.5638 0.5319 0.3302 0.050 Uiso 0.508(2) 1 calc PR A 2
C74 C 0.5782(2) 0.6389(6) 0.3370(8) 0.0416(13) Uani 0.492(2) 1 d PD A 1
H74 H 0.5727 0.5624 0.3212 0.050 Uiso 0.492(2) 1 calc PR A 1
B1 B 0.24014(5) 0.68249(12) 0.57370(8) 0.0298(3) Uani 1 1 d . . .
B2 B 0.26329(5) 0.40451(12) 0.44162(8) 0.0298(3) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 B1 1.3561(16) . ?
O2 H2 0.8400 . ?
O2 B1 1.3620(16) . ?
O3 H3 0.8400 . ?
O3 B2 1.3620(17) . ?
O4 H4 0.8400 . ?
O4 B2 1.3599(16) . ?
O5 C26 1.216(2) . ?
O6 C56 1.2153(18) . ?
N1 C7 1.4759(14) . ?
N1 C8 1.4747(14) . ?
N1 C11 1.4709(14) . ?
N2 C9 1.4659(14) . ?
N2 C10 1.4651(14) . ?
N2 C12 1.4764(14) . ?
N3 C37 1.4776(15) . ?
N3 C38 1.4736(14) . ?
N3 C41 1.4710(13) . ?
N4 C39 1.4661(13) . ?
N4 C40 1.4626(14) . ?
N4 C42 1.4739(15) . ?
C1 C2 1.4151(16) . ?
C1 C6 1.4010(17) . ?
C1 B1 1.5852(19) . ?
C2 C3 1.3910(17) . ?
C2 C7 1.5155(16) . ?
C3 H3A 0.9500 . ?
C3 C4 1.3832(18) . ?
C4 H4A 0.9500 . ?
C4 C5 1.380(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5139(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5118(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C12 C13 1.5230(16) . ?
C12 C19 1.5254(16) . ?
C13 C14 1.3915(17) . ?
C13 C18 1.3941(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3897(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3818(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3873(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3877(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3894(18) . ?
C19 C24 1.3938(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3936(19) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.3884(18) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 C26 1.491(3) . ?
C26 C27 1.484(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C31 C32 1.4112(16) . ?
C31 C36 1.4004(17) . ?
C31 B2 1.5801(19) . ?
C32 C33 1.3904(17) . ?
C32 C37 1.5130(16) . ?
C33 H33 0.9500 . ?
C33 C34 1.3810(19) . ?
C34 H34 0.9500 . ?
C34 C35 1.382(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.385(2) . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.5122(17) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40 C41 1.5086(16) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42 1.0000 . ?
C42 H42A 1.0000 . ?
C42 C43 1.555(5) . ?
C42 C49 1.5250(16) . ?
C42 C63 1.498(5) . ?
C43 C44 1.3948(16) . ?
C43 C68 1.3931(16) . ?
C44 H44 0.9500 . ?
C44 C45 1.3916(16) . ?
C45 H45 0.9500 . ?
C45 C46 1.3907(16) . ?
C46 H46 0.9500 . ?
C46 C47 1.3925(17) . ?
C47 H47 0.9500 . ?
C47 C68 1.3941(16) . ?
C49 C50 1.3921(17) . ?
C49 C54 1.3905(18) . ?
C50 H50 0.9500 . ?
C50 C51 1.3906(17) . ?
C51 H51 0.9500 . ?
C51 C52 1.384(2) . ?
C52 H52 0.9500 . ?
C52 C53 1.382(2) . ?
C53 H53 0.9500 . ?
C53 C54 1.3894(19) . ?
C54 H54 0.9500 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C55 C56 1.478(3) . ?
C56 C57 1.493(2) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C63 C64 1.3926(17) . ?
C63 C74 1.3913(16) . ?
C64 H64 0.9500 . ?
C64 C65 1.3907(17) . ?
C65 H65 0.9500 . ?
C65 C66 1.3909(17) . ?
C66 H66 0.9500 . ?
C66 C67 1.3899(17) . ?
C67 H67 0.9500 . ?
C67 C74 1.3932(16) . ?
C68 H68 0.9500 . ?
C74 H74 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
B1 O1 H1 109.5 . . ?
B1 O2 H2 109.5 . . ?
B2 O3 H3 109.5 . . ?
B2 O4 H4 109.5 . . ?
C8 N1 C7 110.08(9) . . ?
C11 N1 C7 111.09(9) . . ?
C11 N1 C8 108.91(8) . . ?
C9 N2 C12 111.30(9) . . ?
C10 N2 C9 107.44(8) . . ?
C10 N2 C12 112.27(9) . . ?
C38 N3 C37 109.92(8) . . ?
C41 N3 C37 110.32(9) . . ?
C41 N3 C38 109.15(8) . . ?
C39 N4 C42 110.54(9) . . ?
C40 N4 C39 107.26(8) . . ?
C40 N4 C42 113.22(9) . . ?
C2 C1 B1 125.64(10) . . ?
C6 C1 C2 117.07(11) . . ?
C6 C1 B1 117.29(11) . . ?
C1 C2 C7 123.09(10) . . ?
C3 C2 C1 119.88(11) . . ?
C3 C2 C7 116.87(10) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 C2 121.54(12) . . ?
C4 C3 H3A 119.2 . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 C3 119.20(12) . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.02(12) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.24(12) . . ?
C5 C6 H6 118.9 . . ?
N1 C7 C2 114.52(9) . . ?
N1 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C2 C7 H7A 108.6 . . ?
C2 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C9 111.04(9) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
N2 C9 C8 110.00(9) . . ?
N2 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 C11 110.53(9) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
N1 C11 C10 110.22(9) . . ?
N1 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 H12 108.3 . . ?
N2 C12 C13 111.14(9) . . ?
N2 C12 C19 110.36(9) . . ?
C13 C12 H12 108.3 . . ?
C13 C12 C19 110.31(9) . . ?
C19 C12 H12 108.3 . . ?
C14 C13 C12 119.22(10) . . ?
C14 C13 C18 118.81(11) . . ?
C18 C13 C12 121.93(10) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.59(12) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.18(12) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.73(11) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.20(12) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.47(11) . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C12 120.36(11) . . ?
C20 C19 C24 118.72(11) . . ?
C24 C19 C12 120.90(11) . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.60(13) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.20(14) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.72(12) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.29(14) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.45(13) . . ?
C23 C24 H24 119.8 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
O5 C26 C25 122.52(17) . . ?
O5 C26 C27 120.72(16) . . ?
C27 C26 C25 116.75(15) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C32 C31 B2 125.28(11) . . ?
C36 C31 C32 117.29(11) . . ?
C36 C31 B2 117.40(11) . . ?
C31 C32 C37 121.99(11) . . ?
C33 C32 C31 119.90(11) . . ?
C33 C32 C37 118.09(11) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 C32 121.45(12) . . ?
C34 C33 H33 119.3 . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.46(13) . . ?
C35 C34 H34 120.3 . . ?
C34 C35 H35 120.2 . . ?
C34 C35 C36 119.69(12) . . ?
C36 C35 H35 120.2 . . ?
C31 C36 H36 118.9 . . ?
C35 C36 C31 122.15(12) . . ?
C35 C36 H36 118.9 . . ?
N3 C37 C32 112.69(9) . . ?
N3 C37 H37A 109.1 . . ?
N3 C37 H37B 109.1 . . ?
C32 C37 H37A 109.1 . . ?
C32 C37 H37B 109.1 . . ?
H37A C37 H37B 107.8 . . ?
N3 C38 H38A 109.5 . . ?
N3 C38 H38B 109.5 . . ?
N3 C38 C39 110.93(9) . . ?
H38A C38 H38B 108.0 . . ?
C39 C38 H38A 109.5 . . ?
C39 C38 H38B 109.5 . . ?
N4 C39 C38 110.32(9) . . ?
N4 C39 H39A 109.6 . . ?
N4 C39 H39B 109.6 . . ?
C38 C39 H39A 109.6 . . ?
C38 C39 H39B 109.6 . . ?
H39A C39 H39B 108.1 . . ?
N4 C40 H40A 109.8 . . ?
N4 C40 H40B 109.8 . . ?
N4 C40 C41 109.43(9) . . ?
H40A C40 H40B 108.2 . . ?
C41 C40 H40A 109.8 . . ?
C41 C40 H40B 109.8 . . ?
N3 C41 C40 110.68(9) . . ?
N3 C41 H41A 109.5 . . ?
N3 C41 H41B 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 108.1 . . ?
N4 C42 H42 106.5 . . ?
N4 C42 H42A 109.8 . . ?
N4 C42 C43 106.7(5) . . ?
N4 C42 C49 110.04(9) . . ?
N4 C42 C63 113.8(6) . . ?
C43 C42 H42 116.3 . . ?
C43 C42 H42A 109.8 . . ?
C49 C42 H42 106.5 . . ?
C49 C42 H42A 109.8 . . ?
C49 C42 C43 110.6(8) . . ?
C63 C42 H42 106.5 . . ?
C63 C42 H42A 100.1 . . ?
C63 C42 C49 112.8(8) . . ?
C44 C43 C42 121.7(4) . . ?
C68 C43 C42 123.5(3) . . ?
C68 C43 C44 114.8(5) . . ?
C43 C44 H44 118.4 . . ?
C45 C44 C43 123.2(3) . . ?
C45 C44 H44 118.4 . . ?
C44 C45 H45 120.1 . . ?
C46 C45 C44 119.9(3) . . ?
C46 C45 H45 120.1 . . ?
C45 C46 H46 120.5 . . ?
C45 C46 C47 119.1(3) . . ?
C47 C46 H46 120.5 . . ?
C46 C47 H47 120.5 . . ?
C46 C47 C68 119.0(4) . . ?
C68 C47 H47 120.5 . . ?
C50 C49 C42 121.36(11) . . ?
C54 C49 C42 119.84(11) . . ?
C54 C49 C50 118.66(11) . . ?
C49 C50 H50 119.8 . . ?
C51 C50 C49 120.50(12) . . ?
C51 C50 H50 119.8 . . ?
C50 C51 H51 119.9 . . ?
C52 C51 C50 120.26(13) . . ?
C52 C51 H51 119.9 . . ?
C51 C52 H52 120.2 . . ?
C53 C52 C51 119.66(12) . . ?
C53 C52 H52 120.2 . . ?
C52 C53 H53 119.9 . . ?
C52 C53 C54 120.17(13) . . ?
C54 C53 H53 119.9 . . ?
C49 C54 H54 119.6 . . ?
C53 C54 C49 120.75(13) . . ?
C53 C54 H54 119.6 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C56 C55 H55A 109.5 . . ?
C56 C55 H55B 109.5 . . ?
C56 C55 H55C 109.5 . . ?
O6 C56 C55 121.38(16) . . ?
O6 C56 C57 122.03(17) . . ?
C55 C56 C57 116.59(14) . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C64 C63 C42 116.8(4) . . ?
C74 C63 C42 119.6(3) . . ?
C74 C63 C64 123.5(5) . . ?
C63 C64 H64 120.8 . . ?
C65 C64 C63 118.5(3) . . ?
C65 C64 H64 120.8 . . ?
C64 C65 H65 120.4 . . ?
C64 C65 C66 119.1(3) . . ?
C66 C65 H65 120.4 . . ?
C65 C66 H66 119.3 . . ?
C67 C66 C65 121.4(3) . . ?
C67 C66 H66 119.3 . . ?
C66 C67 H67 119.7 . . ?
C66 C67 C74 120.7(4) . . ?
C74 C67 H67 119.7 . . ?
C43 C68 C47 124.0(5) . . ?
C43 C68 H68 118.0 . . ?
C47 C68 H68 118.0 . . ?
C63 C74 C67 116.9(6) . . ?
C63 C74 H74 121.6 . . ?
C67 C74 H74 121.6 . . ?
O1 B1 O2 119.81(12) . . ?
O1 B1 C1 123.25(11) . . ?
O2 B1 C1 116.92(11) . . ?
O3 B2 C31 122.92(10) . . ?
O4 B2 O3 120.19(12) . . ?
O4 B2 C31 116.86(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C9 N2 59.83(12) . . . . ?
N2 C10 C11 N1 -60.82(12) . . . . ?
N2 C12 C13 C14 145.83(10) . . . . ?
N2 C12 C13 C18 -36.53(14) . . . . ?
N2 C12 C19 C20 -127.69(11) . . . . ?
N2 C12 C19 C24 50.65(14) . . . . ?
N3 C38 C39 N4 -58.93(11) . . . . ?
N4 C40 C41 N3 61.76(11) . . . . ?
N4 C42 C43 C44 -145.9(13) . . . . ?
N4 C42 C43 C68 34.1(12) . . . . ?
N4 C42 C49 C50 -61.99(14) . . . . ?
N4 C42 C49 C54 113.54(12) . . . . ?
N4 C42 C63 C64 -137.5(11) . . . . ?
N4 C42 C63 C74 46.5(13) . . . . ?
C1 C2 C3 C4 2.01(17) . . . . ?
C1 C2 C7 N1 61.60(14) . . . . ?
C2 C1 C6 C5 1.03(19) . . . . ?
C2 C1 B1 O1 -18.68(19) . . . . ?
C2 C1 B1 O2 162.91(11) . . . . ?
C2 C3 C4 C5 0.19(19) . . . . ?
C3 C2 C7 N1 -122.97(11) . . . . ?
C3 C4 C5 C6 -1.7(2) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C6 C1 C2 C3 -2.55(16) . . . . ?
C6 C1 C2 C7 172.75(11) . . . . ?
C6 C1 B1 O1 160.44(12) . . . . ?
C6 C1 B1 O2 -17.96(17) . . . . ?
C7 N1 C8 C9 -178.80(9) . . . . ?
C7 N1 C11 C10 178.23(9) . . . . ?
C7 C2 C3 C4 -173.58(11) . . . . ?
C8 N1 C7 C2 -176.32(9) . . . . ?
C8 N1 C11 C10 56.83(11) . . . . ?
C9 N2 C10 C11 61.57(11) . . . . ?
C9 N2 C12 C13 -63.81(11) . . . . ?
C9 N2 C12 C19 173.48(9) . . . . ?
C10 N2 C9 C8 -60.68(11) . . . . ?
C10 N2 C12 C13 175.71(9) . . . . ?
C10 N2 C12 C19 53.01(12) . . . . ?
C11 N1 C7 C2 62.97(12) . . . . ?
C11 N1 C8 C9 -56.79(12) . . . . ?
C12 N2 C9 C8 176.04(9) . . . . ?
C12 N2 C10 C11 -175.74(9) . . . . ?
C12 C13 C14 C15 176.22(10) . . . . ?
C12 C13 C18 C17 -176.92(10) . . . . ?
C12 C19 C20 C21 177.25(11) . . . . ?
C12 C19 C24 C23 -176.79(11) . . . . ?
C13 C12 C19 C20 109.12(12) . . . . ?
C13 C12 C19 C24 -72.54(13) . . . . ?
C13 C14 C15 C16 0.92(17) . . . . ?
C14 C13 C18 C17 0.74(17) . . . . ?
C14 C15 C16 C17 0.45(17) . . . . ?
C15 C16 C17 C18 -1.21(17) . . . . ?
C16 C17 C18 C13 0.61(17) . . . . ?
C18 C13 C14 C15 -1.50(16) . . . . ?
C19 C12 C13 C14 -91.44(12) . . . . ?
C19 C12 C13 C18 86.21(13) . . . . ?
C19 C20 C21 C22 -0.07(19) . . . . ?
C20 C19 C24 C23 1.58(17) . . . . ?
C20 C21 C22 C23 0.83(19) . . . . ?
C21 C22 C23 C24 -0.38(19) . . . . ?
C22 C23 C24 C19 -0.84(18) . . . . ?
C24 C19 C20 C21 -1.13(17) . . . . ?
C31 C32 C33 C34 -0.89(18) . . . . ?
C31 C32 C37 N3 -66.45(13) . . . . ?
C32 C31 C36 C35 -1.61(18) . . . . ?
C32 C31 B2 O3 25.39(18) . . . . ?
C32 C31 B2 O4 -156.91(11) . . . . ?
C32 C33 C34 C35 -0.91(19) . . . . ?
C33 C32 C37 N3 114.69(11) . . . . ?
C33 C34 C35 C36 1.4(2) . . . . ?
C34 C35 C36 C31 -0.1(2) . . . . ?
C36 C31 C32 C33 2.09(16) . . . . ?
C36 C31 C32 C37 -176.75(10) . . . . ?
C36 C31 B2 O3 -152.67(12) . . . . ?
C36 C31 B2 O4 25.02(16) . . . . ?
C37 N3 C38 C39 176.34(9) . . . . ?
C37 N3 C41 C40 -177.61(9) . . . . ?
C37 C32 C33 C34 178.00(11) . . . . ?
C38 N3 C37 C32 178.13(9) . . . . ?
C38 N3 C41 C40 -56.73(11) . . . . ?
C39 N4 C40 C41 -62.77(11) . . . . ?
C39 N4 C42 C43 72.3(7) . . . . ?
C39 N4 C42 C49 -167.68(9) . . . . ?
C39 N4 C42 C63 64.6(7) . . . . ?
C40 N4 C39 C38 61.61(11) . . . . ?
C40 N4 C42 C43 -167.3(7) . . . . ?
C40 N4 C42 C49 -47.31(12) . . . . ?
C40 N4 C42 C63 -175.1(7) . . . . ?
C41 N3 C37 C32 -61.45(11) . . . . ?
C41 N3 C38 C39 55.21(11) . . . . ?
C42 N4 C39 C38 -174.51(9) . . . . ?
C42 N4 C40 C41 175.01(9) . . . . ?
C42 C43 C44 C45 -175.6(9) . . . . ?
C42 C43 C68 C47 176.3(16) . . . . ?
C42 C49 C50 C51 174.82(11) . . . . ?
C42 C49 C54 C53 -174.77(11) . . . . ?
C42 C63 C64 C65 -176.6(9) . . . . ?
C42 C63 C74 C67 175.6(16) . . . . ?
C43 C42 C49 C50 55.6(2) . . . . ?
C43 C42 C49 C54 -128.9(2) . . . . ?
C43 C42 C63 C64 176(10) . . . . ?
C43 C42 C63 C74 0(8) . . . . ?
C43 C44 C45 C46 -2.0(12) . . . . ?
C44 C43 C68 C47 -3.7(12) . . . . ?
C44 C45 C46 C47 -1.4(6) . . . . ?
C45 C46 C47 C68 2.0(9) . . . . ?
C46 C47 C68 C43 0.6(10) . . . . ?
C49 C42 C43 C44 94.4(14) . . . . ?
C49 C42 C43 C68 -85.5(11) . . . . ?
C49 C42 C63 C64 96.2(14) . . . . ?
C49 C42 C63 C74 -79.8(11) . . . . ?
C49 C50 C51 C52 0.23(18) . . . . ?
C50 C49 C54 C53 0.88(18) . . . . ?
C50 C51 C52 C53 0.21(19) . . . . ?
C51 C52 C53 C54 -0.09(19) . . . . ?
C52 C53 C54 C49 -0.46(19) . . . . ?
C54 C49 C50 C51 -0.76(17) . . . . ?
C63 C42 C43 C44 -10(7) . . . . ?
C63 C42 C43 C68 170(10) . . . . ?
C63 C42 C49 C50 66.3(2) . . . . ?
C63 C42 C49 C54 -118.1(2) . . . . ?
C63 C64 C65 C66 1.5(12) . . . . ?
C64 C63 C74 C67 -0.2(13) . . . . ?
C64 C65 C66 C67 -1.4(7) . . . . ?
C65 C66 C67 C74 0.4(9) . . . . ?
C66 C67 C74 C63 0.4(9) . . . . ?
C68 C43 C44 C45 4.4(15) . . . . ?
C74 C63 C64 C65 -0.8(17) . . . . ?
B1 C1 C2 C3 176.58(11) . . . . ?
B1 C1 C2 C7 -8.12(18) . . . . ?
B1 C1 C6 C5 -178.17(12) . . . . ?
B2 C31 C32 C33 -175.97(11) . . . . ?
B2 C31 C32 C37 5.18(17) . . . . ?
B2 C31 C36 C35 176.61(12) . . . . ?

#=====end of cif
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
