# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1x2B_ap91_1b
_database_code_depnum_ccdc_archive 'CCDC 1568422'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;
_audit_creation_date             2013-07-03
_audit_creation_method           
;
  Olex2 1.2
  (compiled Nov  5 2012 18:25:38, GUI svn.r4372)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(B H3 O3), C12 H20 N2 O3'
_chemical_formula_sum            'C12 H26 B2 N2 O9'
_chemical_formula_weight         363.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H26N2O9B2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.0629(4)
_cell_length_b                   7.9863(4)
_cell_length_c                   17.6846(9)
_cell_angle_alpha                79.301(5)
_cell_angle_beta                 80.217(5)
_cell_angle_gamma                68.622(5)
_cell_volume                     907.03(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2884
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.6070
_cell_measurement_theta_min      2.7586
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.507
_exptl_crystal_size_mid          0.3695
_exptl_crystal_size_min          0.1711
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10266
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.76
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9964
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   44.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429   77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   -2.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -77.0000  150.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00    0.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -77.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega  -37.00   -5.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -57.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -17.00  100.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679   19.0000 -180.0000 117

#__ type_ start__ end____ width___ exp.time_
  6 omega    6.00   73.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -109.0000   98.0000 67

#__ type_ start__ end____ width___ exp.time_
  7 omega  -99.00   -1.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -38.0000  -30.0000 98

#__ type_ start__ end____ width___ exp.time_
  8 omega  -42.00  -10.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  -57.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   56.00  103.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  179.0000  -60.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0459460000
_diffrn_orient_matrix_UB_12      -0.0417415000
_diffrn_orient_matrix_UB_13      0.0332300000
_diffrn_orient_matrix_UB_21      -0.0730081000
_diffrn_orient_matrix_UB_22      -0.0027246000
_diffrn_orient_matrix_UB_23      -0.0223432000
_diffrn_orient_matrix_UB_31      0.0658532000
_diffrn_orient_matrix_UB_32      -0.0866909000
_diffrn_orient_matrix_UB_33      -0.0091497000
_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                3067
_reflns_number_total             3945
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
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.
;
_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.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0397
_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)+(0.0398P)²+0.1429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0965
_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:
  {H2A,H2B} of C2, {H3A,H3B} of C3, {H7A,H7B} of C7, {H6A,H6B} of C6, {H8A,
  H8B} of C8, {H5A,H5B} of C5, {H10A,H10B} of C10, {H12A,H12B} of C12, {H4A,
  H4B} of C4, {H11A,H11B} of C11
 At 1.5 times of:
  H9 of O9, H5 of O5, H4 of O4, H6 of O6, H7 of O7
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B), C6(H6A,H6B), C7(H7A,H7B), C3(H3A,H3B), C2(H2A,H2B),
 C10(H10A,H10B), C12(H12A,H12B), C4(H4A,H4B), C11(H11A,H11B)
2.b Idealised tetrahedral OH refined as rotating group:
 O6(H6), O7(H7), O4(H4), O9(H9), O5(H5)
;
_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
O6 O 0.23813(14) 0.48082(14) 0.28514(5) 0.0252(2) Uani 1 1 d . . .
H6 H 0.3510 0.4586 0.3014 0.038 Uiso 1 1 calc R . .
O7 O 0.57508(14) 1.40138(14) -0.64473(5) 0.0260(2) Uani 1 1 d . . .
H7 H 0.5919 1.3487 -0.5994 0.039 Uiso 1 1 calc R . .
O4 O 0.08252(15) 0.59902(15) 0.16950(5) 0.0298(3) Uani 1 1 d . . .
H4 H -0.0137 0.5759 0.1992 0.045 Uiso 1 1 calc R . .
O9 O 0.91775(14) 1.37256(14) -0.64068(5) 0.0262(2) Uani 1 1 d . . .
H9 H 1.0101 1.4064 -0.6681 0.039 Uiso 1 1 calc R . .
O1 O 0.39609(16) 0.76404(15) 0.03029(6) 0.0306(3) Uani 1 1 d . . .
O5 O 0.42182(15) 0.58009(14) 0.17202(5) 0.0266(2) Uani 1 1 d . . .
H5 H 0.4037 0.6288 0.1262 0.040 Uiso 1 1 calc R . .
O2 O 0.48552(15) 1.00057(14) -0.23245(5) 0.0268(2) Uani 1 1 d . . .
O8 O 0.75867(15) 1.51177(14) -0.75463(6) 0.0255(2) Uani 1 1 d . . .
O3 O 0.59323(16) 1.22353(15) -0.50536(6) 0.0312(3) Uani 1 1 d . . .
N1 N 0.25217(18) 0.89926(16) -0.08158(6) 0.0241(3) Uani 1 1 d . . .
N2 N 0.42690(18) 1.10713(16) -0.39838(6) 0.0238(3) Uani 1 1 d . . .
C1 C 0.2862(2) 0.7728(2) -0.01934(8) 0.0234(3) Uani 1 1 d . . .
C5 C 0.3482(2) 1.0374(2) -0.10022(8) 0.0256(3) Uani 1 1 d . . .
H5A H 0.3839 1.0581 -0.0518 0.031 Uiso 1 1 calc R . .
H5B H 0.2478 1.1525 -0.1218 0.031 Uiso 1 1 calc R . .
C8 C 0.6086(2) 0.9777(2) -0.36591(8) 0.0259(3) Uani 1 1 d . . .
H8A H 0.7290 0.9748 -0.4043 0.031 Uiso 1 1 calc R . .
H8B H 0.5972 0.8555 -0.3575 0.031 Uiso 1 1 calc R . .
C6 C 0.5383(2) 0.9896(2) -0.15715(8) 0.0267(3) Uani 1 1 d . . .
H6A H 0.6123 1.0742 -0.1581 0.032 Uiso 1 1 calc R . .
H6B H 0.6300 0.8651 -0.1408 0.032 Uiso 1 1 calc R . .
C7 C 0.6459(2) 1.0167(2) -0.29086(8) 0.0270(3) Uani 1 1 d . . .
H7A H 0.7789 0.9299 -0.2754 0.032 Uiso 1 1 calc R . .
H7B H 0.6509 1.1409 -0.2974 0.032 Uiso 1 1 calc R . .
C9 C 0.4332(2) 1.21547(19) -0.46567(8) 0.0237(3) Uani 1 1 d . . .
C3 C 0.0259(2) 0.7465(2) -0.08139(8) 0.0305(3) Uani 1 1 d . . .
H3A H 0.0088 0.6611 -0.1115 0.037 Uiso 1 1 calc R . .
H3B H -0.1097 0.8161 -0.0564 0.037 Uiso 1 1 calc R . .
C2 C 0.1750(2) 0.6455(2) -0.02118(8) 0.0282(3) Uani 1 1 d . . .
H2A H 0.1008 0.6220 0.0301 0.034 Uiso 1 1 calc R . .
H2B H 0.2710 0.5286 -0.0369 0.034 Uiso 1 1 calc R . .
C10 C 0.2177(2) 1.3233(2) -0.48353(8) 0.0280(3) Uani 1 1 d . . .
H10A H 0.2043 1.3277 -0.5387 0.034 Uiso 1 1 calc R . .
H10B H 0.1757 1.4488 -0.4714 0.034 Uiso 1 1 calc R . .
B2 B 0.7508(2) 1.4280(2) -0.67954(9) 0.0204(3) Uani 1 1 d . . .
C12 C 0.2189(2) 1.1183(2) -0.36461(8) 0.0290(3) Uani 1 1 d . . .
H12A H 0.1749 1.1863 -0.3195 0.035 Uiso 1 1 calc R . .
H12B H 0.2095 0.9959 -0.3481 0.035 Uiso 1 1 calc R . .
C4 C 0.1269(2) 0.8734(2) -0.13316(8) 0.0296(3) Uani 1 1 d . . .
H4A H 0.2123 0.8169 -0.1784 0.036 Uiso 1 1 calc R . .
H4B H 0.0233 0.9900 -0.1516 0.036 Uiso 1 1 calc R . .
B1 B 0.2469(2) 0.5529(2) 0.20879(9) 0.0210(3) Uani 1 1 d . . .
C11 C 0.0899(2) 1.2200(2) -0.43117(9) 0.0336(4) Uani 1 1 d . . .
H11A H 0.0665 1.1342 -0.4592 0.040 Uiso 1 1 calc R . .
H11B H -0.0440 1.3047 -0.4117 0.040 Uiso 1 1 calc R . .
H8 H 0.652(3) 1.540(2) -0.7769(11) 0.045(5) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 H6 0.8400 . ?
O6 B1 1.3665(17) . ?
O7 H7 0.8400 . ?
O7 B2 1.3594(18) . ?
O4 H4 0.8400 . ?
O4 B1 1.3541(18) . ?
O9 H9 0.8400 . ?
O9 B2 1.3567(18) . ?
O1 C1 1.2437(17) . ?
O5 H5 0.8400 . ?
O5 B1 1.3664(18) . ?
O2 C6 1.4219(16) . ?
O2 C7 1.4232(16) . ?
O8 B2 1.3735(18) . ?
O8 H8 0.85(2) . ?
O3 C9 1.2413(17) . ?
N1 C1 1.3378(17) . ?
N1 C5 1.4558(19) . ?
N1 C4 1.4613(19) . ?
N2 C8 1.4516(18) . ?
N2 C9 1.3396(17) . ?
N2 C12 1.4660(18) . ?
C1 C2 1.502(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.508(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.503(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.505(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.528(2) . ?
C3 C4 1.528(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.526(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.531(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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 O6 H6 109.5 . . ?
B2 O7 H7 109.5 . . ?
B1 O4 H4 109.5 . . ?
B2 O9 H9 109.5 . . ?
B1 O5 H5 109.5 . . ?
C6 O2 C7 111.55(11) . . ?
B2 O8 H8 116.2(13) . . ?
C1 N1 C5 123.20(12) . . ?
C1 N1 C4 113.33(12) . . ?
C5 N1 C4 123.17(11) . . ?
C8 N2 C12 122.94(11) . . ?
C9 N2 C8 123.27(12) . . ?
C9 N2 C12 113.50(12) . . ?
O1 C1 N1 124.13(14) . . ?
O1 C1 C2 126.91(13) . . ?
N1 C1 C2 108.95(12) . . ?
N1 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
N1 C5 C6 114.03(12) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
N2 C8 H8A 108.5 . . ?
N2 C8 H8B 108.5 . . ?
N2 C8 C7 114.89(12) . . ?
H8A C8 H8B 107.5 . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
O2 C6 C5 110.17(12) . . ?
O2 C6 H6A 109.6 . . ?
O2 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
O2 C7 C8 109.39(12) . . ?
O2 C7 H7A 109.8 . . ?
O2 C7 H7B 109.8 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
O3 C9 N2 124.35(13) . . ?
O3 C9 C10 126.81(12) . . ?
N2 C9 C10 108.84(12) . . ?
H3A C3 H3B 109.0 . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C4 C3 C2 103.86(12) . . ?
C1 C2 C3 103.74(12) . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C9 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
C9 C10 C11 103.89(12) . . ?
H10A C10 H10B 109.0 . . ?
C11 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
O7 B2 O8 119.56(13) . . ?
O9 B2 O7 120.52(12) . . ?
O9 B2 O8 119.92(13) . . ?
N2 C12 H12A 111.1 . . ?
N2 C12 H12B 111.1 . . ?
N2 C12 C11 103.27(11) . . ?
H12A C12 H12B 109.1 . . ?
C11 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
N1 C4 C3 102.83(11) . . ?
N1 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
O4 B1 O6 120.38(13) . . ?
O4 B1 O5 119.77(12) . . ?
O5 B1 O6 119.85(13) . . ?
C10 C11 C12 104.22(13) . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C12 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6 O7 0.84 1.86 2.6860(14) 169.4 1_546 yes
O7 H7 O3 0.84 1.77 2.6045(13) 170.0 . yes
O4 H4 O8 0.84 1.87 2.7000(14) 167.2 1_446 yes
O9 H9 O6 0.84 1.92 2.7541(13) 170.4 1_664 yes
O5 H5 O1 0.84 1.83 2.6583(13) 167.5 . yes
O8 H8 O5 0.85(2) 1.89(2) 2.7350(14) 175.0(18) 1_564 yes

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
O1 C1 C2 C3 166.26(14) . . . . ?
O3 C9 C10 C11 163.03(15) . . . . ?
N1 C1 C2 C3 -14.92(15) . . . . ?
N1 C5 C6 O2 72.05(15) . . . . ?
N2 C8 C7 O2 65.02(16) . . . . ?
N2 C9 C10 C11 -17.38(16) . . . . ?
N2 C12 C11 C10 -22.81(16) . . . . ?
C1 N1 C5 C6 95.87(15) . . . . ?
C1 N1 C4 C3 18.19(16) . . . . ?
C5 N1 C1 O1 2.9(2) . . . . ?
C5 N1 C1 C2 -176.00(12) . . . . ?
C5 N1 C4 C3 -167.94(13) . . . . ?
C8 N2 C9 O3 -3.7(2) . . . . ?
C8 N2 C9 C10 176.75(13) . . . . ?
C8 N2 C12 C11 -160.98(13) . . . . ?
C6 O2 C7 C8 164.93(12) . . . . ?
C7 O2 C6 C5 160.47(12) . . . . ?
C9 N2 C8 C7 114.94(15) . . . . ?
C9 N2 C12 C11 13.12(17) . . . . ?
C9 C10 C11 C12 24.43(15) . . . . ?
C2 C3 C4 N1 -25.91(15) . . . . ?
C12 N2 C8 C7 -71.53(18) . . . . ?
C12 N2 C9 O3 -177.73(14) . . . . ?
C12 N2 C9 C10 2.67(17) . . . . ?
C4 N1 C1 O1 176.73(14) . . . . ?
C4 N1 C1 C2 -2.13(16) . . . . ?
C4 N1 C5 C6 -77.40(17) . . . . ?
C4 C3 C2 C1 25.01(15) . . . . ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-8 -8 -14 0.1110 -7.9864 -8.0055 -13.9623 0.2371 0.9168 0.2958
8 8 14 0.1110 7.9864 8.0055 13.9623 -0.2371 -0.9168 -0.2958
0 -10 -10 0.1932 -0.0022 -10.0110 -9.9558 0.0871 0.2499 0.9588
-2 9 8 0.2266 -1.9942 9.0110 7.9603 -0.0200 -0.0568 -0.9853
-5 -2 -23 0.0854 -4.9903 -2.0111 -22.9714 -0.4501 0.8831 0.0559
5 1 23 0.0820 4.9901 1.0106 22.9748 0.4920 -0.8804 0.0308
3 5 24 0.0771 2.9948 5.0149 23.9593 0.4492 -0.7676 -0.4567
9 8 -1 0.1297 8.9849 7.9951 -1.0214 -0.7805 -0.6549 -0.0921
-3 1 22 0.1231 -2.9947 1.0171 21.9719 0.8253 -0.2751 -0.4864

####################################################################### 
# 
# 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_1xC6_15srv191
_database_code_depnum_ccdc_archive 'CCDC 1568423'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;
_audit_creation_date             2015-07-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H8 B2 O4, C12 H20 N2 O3'
_chemical_formula_sum            'C18 H28 B2 N2 O7'
_chemical_formula_weight         406.04
_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      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                   10.0731(4)
_cell_length_b                   10.2343(4)
_cell_length_c                   12.1312(5)
_cell_angle_alpha                112.5470(10)
_cell_angle_beta                 111.5550(10)
_cell_angle_gamma                94.5390(10)
_cell_volume                     1038.42(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6631
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.01
_cell_measurement_theta_min      2.23
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9606
_exptl_absorpt_correction_T_min  0.7497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0651 before and 0.0523 after correction.
The Ratio of minimum to maximum transmission is 0.7804.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (5 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18453
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.02
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'SMART 6K'
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                4790
_reflns_number_total             6065
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6065
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.064
_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)+(0.1000P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1682
_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,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H20C(0.5) H20D(0.5) H20A(0.5) H20B(0.5) C21A(0.5) H21A(0.5)
 H21B(0.5) C21B(0.5) H21C(0.5) H21D(0.5) H22C(0.5) H22D(0.5) H22A(0.5) H22B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C20(H20C,H20D), C20(H20A,
 H20B), C21A(H21A,H21B), C21B(H21C,H21D), C22(H22C,H22D), C22(H22A,H22B)
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O -0.14071(11) 0.30747(12) 0.89369(10) 0.0296(2) Uani 1 d . . .
O2 O -0.08153(11) 0.20251(12) 1.04680(10) 0.0286(2) Uani 1 d . . .
O3 O 0.56739(11) 0.24686(13) 0.86282(10) 0.0304(2) Uani 1 d . . .
O4 O 0.66656(10) 0.26334(13) 1.07148(10) 0.0317(2) Uani 1 d . . .
C1 C 0.10607(13) 0.25124(14) 0.96714(12) 0.0213(2) Uani 1 d . . .
C2 C 0.15896(14) 0.32684(16) 0.91056(14) 0.0258(3) Uani 1 d . . .
C3 C 0.29684(14) 0.32693(16) 0.91068(14) 0.0266(3) Uani 1 d . . .
C4 C 0.38978(13) 0.25574(14) 0.97112(12) 0.0222(2) Uani 1 d . . .
C5 C 0.33776(14) 0.18166(14) 1.02905(13) 0.0232(3) Uani 1 d . . .
C6 C 0.19770(14) 0.17767(14) 1.02525(13) 0.0231(2) Uani 1 d . . .
B1 B -0.04880(15) 0.25339(16) 0.96906(13) 0.0218(3) Uani 1 d . . .
B2 B 0.54427(16) 0.25550(17) 0.96924(14) 0.0244(3) Uani 1 d . . .
H1 H -0.229(3) 0.302(3) 0.893(3) 0.072(8) Uiso 1 d . . .
H2 H -0.164(3) 0.218(2) 1.055(2) 0.051(6) Uiso 1 d . . .
H2A H 0.098(2) 0.379(2) 0.8679(19) 0.037(5) Uiso 1 d . . .
H3 H 0.486(3) 0.218(3) 0.788(3) 0.070(7) Uiso 1 d . . .
H3A H 0.3284(19) 0.3821(19) 0.8681(17) 0.029(4) Uiso 1 d . . .
H4 H 0.663(3) 0.284(3) 1.146(2) 0.055(6) Uiso 1 d . . .
H5 H 0.4007(19) 0.1291(19) 1.0724(17) 0.028(4) Uiso 1 d . . .
H6 H 0.162(2) 0.121(2) 1.0622(18) 0.031(4) Uiso 1 d . . .
O11 O 0.68039(10) 0.43710(11) 0.60979(9) 0.0252(2) Uani 1 d . . .
O12 O 0.71079(12) 0.33777(12) 0.31724(10) 0.0321(2) Uani 1 d . . .
O13 O 0.34601(12) 0.13140(12) 0.61636(10) 0.0329(2) Uani 1 d . . .
N1 N 0.88702(12) 0.32809(13) 0.49516(11) 0.0261(2) Uani 1 d . . .
N2 N 0.38964(12) 0.24940(12) 0.50179(11) 0.0241(2) Uani 1 d B . .
C11 C 0.83613(15) 0.47918(18) 0.68384(13) 0.0300(3) Uani 1 d . . .
C12 C 0.90738(15) 0.47455(16) 0.59259(13) 0.0289(3) Uani 1 d . . .
C13 C 0.79128(15) 0.27147(15) 0.36757(13) 0.0254(3) Uani 1 d . . .
C14 C 0.7978(2) 0.11675(18) 0.29761(17) 0.0422(4) Uani 1 d . . .
H14A H 0.8055 0.0995 0.2143 0.051 Uiso 1 calc . . R
H14B H 0.7090 0.0460 0.2769 0.051 Uiso 1 calc . . R
C15 C 0.9351(2) 0.1031(2) 0.3948(2) 0.0516(5) Uani 1 d . . .
H15A H 1.0182 0.1128 0.3711 0.062 Uiso 1 calc . . R
H15B H 0.9174 0.0071 0.3958 0.062 Uiso 1 calc . . R
C16 C 0.9689(2) 0.2274(2) 0.52924(18) 0.0462(4) Uani 1 d . . .
H16A H 0.9343 0.1915 0.5815 0.055 Uiso 1 calc . . R
H16B H 1.0761 0.2748 0.5803 0.055 Uiso 1 calc . . R
C17 C 0.60837(16) 0.43726(16) 0.69103(13) 0.0270(3) Uani 1 d . . .
C18 C 0.44357(15) 0.39692(15) 0.60912(13) 0.0260(3) Uani 1 d . . .
C19 C 0.34727(14) 0.13116(15) 0.51444(13) 0.0253(3) Uani 1 d B . .
C20 C 0.30147(16) -0.00215(15) 0.38402(14) 0.0297(3) Uani 1 d . . .
H20C H 0.1926 -0.0379 0.3359 0.036 Uiso 0.50 calc A 2 R
H20D H 0.3429 -0.0820 0.3980 0.036 Uiso 0.50 calc A 2 R
H20A H 0.3772 -0.0584 0.3890 0.036 Uiso 0.50 calc A 1 R
H20B H 0.2061 -0.0669 0.3584 0.036 Uiso 0.50 calc A 1 R
C21A C 0.2876(4) 0.0600(3) 0.2881(3) 0.0331(6) Uiso 0.50 d B 1 .
H21A H 0.1833 0.0571 0.2393 0.040 Uiso 0.50 calc B 1 R
H21B H 0.3240 0.0036 0.2234 0.040 Uiso 0.50 calc B 1 R
C21B C 0.3662(3) 0.0524(3) 0.3063(3) 0.0268(5) Uiso 0.50 d B 2 .
H21C H 0.4632 0.0312 0.3173 0.032 Uiso 0.50 calc B 2 R
H21D H 0.2982 0.0067 0.2109 0.032 Uiso 0.50 calc B 2 R
C22 C 0.38141(17) 0.21726(16) 0.37058(13) 0.0299(3) Uani 1 d . . .
H22C H 0.4720 0.2724 0.3779 0.036 Uiso 0.50 calc B 2 R
H22D H 0.2949 0.2425 0.3187 0.036 Uiso 0.50 calc B 2 R
H22A H 0.4807 0.2255 0.3720 0.036 Uiso 0.50 calc B 1 R
H22B H 0.3334 0.2835 0.3368 0.036 Uiso 0.50 calc B 1 R
H11A H 0.868(2) 0.416(2) 0.7258(19) 0.035(5) Uiso 1 d . . .
H11B H 0.869(2) 0.580(2) 0.7556(19) 0.037(5) Uiso 1 d . . .
H12A H 0.8648(18) 0.5322(18) 0.5436(17) 0.023(4) Uiso 1 d . . .
H12B H 1.015(2) 0.5210(19) 0.6490(17) 0.027(4) Uiso 1 d . . .
H17A H 0.6321(18) 0.3696(19) 0.7278(17) 0.027(4) Uiso 1 d . . .
H17B H 0.638(2) 0.535(2) 0.764(2) 0.038(5) Uiso 1 d . . .
H18A H 0.4197(19) 0.4628(19) 0.5705(18) 0.030(4) Uiso 1 d . . .
H18B H 0.390(2) 0.403(2) 0.6648(18) 0.032(4) Uiso 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 B1 1.3590(17) . ?
O1 H1 0.88(3) . ?
O2 B1 1.3590(17) . ?
O2 H2 0.89(2) . ?
O3 B2 1.3659(17) . ?
O3 H3 0.89(3) . ?
O4 B2 1.3593(17) . ?
O4 H4 0.86(2) . ?
C1 C2 1.4015(18) . ?
C1 C6 1.3981(17) . ?
C1 B1 1.5704(18) . ?
C2 C3 1.3883(18) . ?
C2 H2A 0.98(2) . ?
C3 C4 1.3993(18) . ?
C3 H3A 1.002(18) . ?
C4 C5 1.3997(18) . ?
C4 B2 1.5649(18) . ?
C5 C6 1.3915(17) . ?
C5 H5 0.997(18) . ?
C6 H6 0.976(19) . ?
O11 C11 1.4194(17) . ?
O11 C17 1.4220(16) . ?
O12 C13 1.2376(17) . ?
O13 C19 1.2403(16) . ?
N1 C12 1.4494(18) . ?
N1 C13 1.3373(17) . ?
N1 C16 1.457(2) . ?
N2 C18 1.4535(17) . ?
N2 C19 1.3337(17) . ?
N2 C22 1.4649(17) . ?
C11 C12 1.5138(19) . ?
C11 H11A 0.97(2) . ?
C11 H11B 0.99(2) . ?
C12 H12A 1.004(17) . ?
C12 H12B 0.999(18) . ?
C13 C14 1.503(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.510(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.526(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5094(19) . ?
C17 H17A 0.959(18) . ?
C17 H17B 0.97(2) . ?
C18 H18A 0.958(18) . ?
C18 H18B 0.999(19) . ?
C19 C20 1.5119(19) . ?
C20 H20C 0.9900 . ?
C20 H20D 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21A 1.497(3) . ?
C20 C21B 1.556(3) . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C21A C22 1.521(3) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C21B C22 1.530(3) . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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 115.2(17) . . ?
B1 O2 H2 115.3(14) . . ?
B2 O3 H3 115.2(17) . . ?
B2 O4 H4 117.9(16) . . ?
C2 C1 B1 121.03(11) . . ?
C6 C1 C2 117.74(11) . . ?
C6 C1 B1 121.21(11) . . ?
C1 C2 H2A 120.6(11) . . ?
C3 C2 C1 121.08(12) . . ?
C3 C2 H2A 118.3(11) . . ?
C2 C3 C4 121.19(12) . . ?
C2 C3 H3A 117.6(10) . . ?
C4 C3 H3A 121.2(10) . . ?
C3 C4 C5 117.75(11) . . ?
C3 C4 B2 120.60(11) . . ?
C5 C4 B2 121.62(11) . . ?
C4 C5 H5 119.9(10) . . ?
C6 C5 C4 121.05(12) . . ?
C6 C5 H5 119.0(10) . . ?
C1 C6 H6 119.5(10) . . ?
C5 C6 C1 121.15(12) . . ?
C5 C6 H6 119.3(10) . . ?
O1 B1 O2 124.33(12) . . ?
O1 B1 C1 117.69(11) . . ?
O2 B1 C1 117.97(11) . . ?
O3 B2 C4 122.27(12) . . ?
O4 B2 O3 113.97(12) . . ?
O4 B2 C4 123.76(12) . . ?
C11 O11 C17 110.88(10) . . ?
C12 N1 C16 122.27(12) . . ?
C13 N1 C12 124.02(12) . . ?
C13 N1 C16 113.70(13) . . ?
C18 N2 C22 122.59(11) . . ?
C19 N2 C18 123.41(11) . . ?
C19 N2 C22 113.98(11) . . ?
O11 C11 C12 108.81(11) . . ?
O11 C11 H11A 111.0(11) . . ?
O11 C11 H11B 110.7(11) . . ?
C12 C11 H11A 111.2(11) . . ?
C12 C11 H11B 108.3(11) . . ?
H11A C11 H11B 106.8(16) . . ?
N1 C12 C11 113.85(12) . . ?
N1 C12 H12A 107.6(10) . . ?
N1 C12 H12B 109.2(10) . . ?
C11 C12 H12A 109.6(10) . . ?
C11 C12 H12B 107.4(10) . . ?
H12A C12 H12B 109.1(14) . . ?
O12 C13 N1 124.53(13) . . ?
O12 C13 C14 126.36(13) . . ?
N1 C13 C14 109.11(12) . . ?
C13 C14 H14A 110.9 . . ?
C13 C14 H14B 110.9 . . ?
C13 C14 C15 104.26(14) . . ?
H14A C14 H14B 108.9 . . ?
C15 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
C14 C15 H15A 110.6 . . ?
C14 C15 H15B 110.6 . . ?
C14 C15 C16 105.52(14) . . ?
H15A C15 H15B 108.8 . . ?
C16 C15 H15A 110.6 . . ?
C16 C15 H15B 110.6 . . ?
N1 C16 C15 103.38(13) . . ?
N1 C16 H16A 111.1 . . ?
N1 C16 H16B 111.1 . . ?
C15 C16 H16A 111.1 . . ?
C15 C16 H16B 111.1 . . ?
H16A C16 H16B 109.1 . . ?
O11 C17 C18 108.85(11) . . ?
O11 C17 H17A 112.4(10) . . ?
O11 C17 H17B 109.3(11) . . ?
C18 C17 H17A 109.0(10) . . ?
C18 C17 H17B 108.9(12) . . ?
H17A C17 H17B 108.3(15) . . ?
N2 C18 C17 112.21(11) . . ?
N2 C18 H18A 107.6(11) . . ?
N2 C18 H18B 107.9(11) . . ?
C17 C18 H18A 109.2(11) . . ?
C17 C18 H18B 111.0(11) . . ?
H18A C18 H18B 108.8(15) . . ?
O13 C19 N2 125.44(13) . . ?
O13 C19 C20 126.09(13) . . ?
N2 C19 C20 108.47(11) . . ?
C19 C20 H20C 110.9 . . ?
C19 C20 H20D 110.9 . . ?
C19 C20 H20A 111.0 . . ?
C19 C20 H20B 111.0 . . ?
C19 C20 C21B 104.38(14) . . ?
H20C C20 H20D 108.9 . . ?
H20C C20 H20A 129.4 . . ?
H20C C20 H20B 27.5 . . ?
H20D C20 H20A 27.7 . . ?
H20D C20 H20B 84.1 . . ?
H20A C20 H20B 109.0 . . ?
C21A C20 C19 103.93(16) . . ?
C21A C20 H20C 84.9 . . ?
C21A C20 H20D 133.8 . . ?
C21A C20 H20A 111.0 . . ?
C21A C20 H20B 111.0 . . ?
C21A C20 C21B 28.69(14) . . ?
C21B C20 H20C 110.9 . . ?
C21B C20 H20D 110.9 . . ?
C21B C20 H20A 84.7 . . ?
C21B C20 H20B 133.3 . . ?
C20 C21A H21A 110.5 . . ?
C20 C21A H21B 110.5 . . ?
C20 C21A C22 106.0(2) . . ?
H21A C21A H21B 108.7 . . ?
C22 C21A H21A 110.5 . . ?
C22 C21A H21B 110.5 . . ?
C20 C21B H21C 111.2 . . ?
C20 C21B H21D 111.2 . . ?
H21C C21B H21D 109.1 . . ?
C22 C21B C20 102.69(18) . . ?
C22 C21B H21C 111.2 . . ?
C22 C21B H21D 111.2 . . ?
N2 C22 C21A 102.28(15) . . ?
N2 C22 C21B 104.24(14) . . ?
N2 C22 H22C 110.9 . . ?
N2 C22 H22D 110.9 . . ?
N2 C22 H22A 111.3 . . ?
N2 C22 H22B 111.3 . . ?
C21A C22 C21B 28.79(14) . . ?
C21A C22 H22C 134.9 . . ?
C21A C22 H22D 85.5 . . ?
C21A C22 H22A 111.3 . . ?
C21A C22 H22B 111.3 . . ?
C21B C22 H22C 110.9 . . ?
C21B C22 H22D 110.9 . . ?
C21B C22 H22A 84.4 . . ?
C21B C22 H22B 132.9 . . ?
H22C C22 H22D 108.9 . . ?
H22C C22 H22A 27.9 . . ?
H22C C22 H22B 84.4 . . ?
H22D C22 H22A 129.2 . . ?
H22D C22 H22B 27.1 . . ?
H22A C22 H22B 109.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.88(3) 1.94(3) 2.8097(14) 168(3) 1_455
O2 H2 O4 0.89(2) 1.86(2) 2.7534(13) 176(2) 1_455
O3 H3 O13 0.89(3) 1.83(3) 2.6986(15) 166(2) .
O4 H4 O12 0.86(2) 1.79(3) 2.6260(14) 164(2) 1_556

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 C12 C11 O11 -68.81(16) . . . . ?
N2 C18 C17 O11 63.45(15) . . . . ?
C11 C12 N1 C13 103.64(15) . . . . ?
C11 C12 N1 C16 -75.22(17) . . . . ?
C12 N1 C13 O12 1.2(2) . . . . ?
C12 C11 O11 C17 178.96(12) . . . . ?
C13 C14 C15 C16 19.3(2) . . . . ?
C14 C13 N1 C12 -178.57(13) . . . . ?
C14 C13 N1 C16 0.38(17) . . . . ?
C14 C15 C16 N1 -19.0(2) . . . . ?
C15 C14 C13 O12 167.52(15) . . . . ?
C15 C14 C13 N1 -12.68(18) . . . . ?
C16 N1 C13 O12 -179.82(14) . . . . ?
C17 C18 N2 C19 88.70(15) . . . . ?
C17 C18 N2 C22 -89.36(15) . . . . ?
C18 N2 C19 O13 1.2(2) . . . . ?
C18 C17 O11 C11 178.10(11) . . . . ?
C19 C20 C21A C22 22.1(2) . . . . ?
C19 C20 C21B C22 -23.7(2) . . . . ?
C20 C19 N2 C18 -178.80(11) . . . . ?
C20 C19 N2 C22 -0.58(16) . . . . ?
C20 C21A C22 N2 -22.1(2) . . . . ?
C20 C21A C22 C21B 75.1(3) . . . . ?
C20 C21B C22 N2 23.2(2) . . . . ?
C20 C21B C22 C21A -66.4(3) . . . . ?
C21A C20 C19 O13 166.21(18) . . . . ?
C21A C20 C19 N2 -13.81(19) . . . . ?
C21A C20 C21B C22 69.1(3) . . . . ?
C21A C22 N2 C18 -167.38(17) . . . . ?
C21A C22 N2 C19 14.39(19) . . . . ?
C21B C20 C19 O13 -164.19(16) . . . . ?
C21B C20 C19 N2 15.80(17) . . . . ?
C21B C20 C21A C22 -72.4(3) . . . . ?
C21B C22 N2 C18 163.09(15) . . . . ?
C21B C22 N2 C19 -15.14(18) . . . . ?
C22 N2 C19 O13 179.40(13) . . . . ?

####################################################################### 
# 
# 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_22xC6_ap71_3
_database_code_depnum_ccdc_archive 'CCDC 1568425'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;
_audit_creation_date             2014-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H7 B O3, 2(C6 H11 N O)'
_chemical_formula_sum            'C18 H29 B N2 O5'
_chemical_formula_weight         364.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H33BN2O5
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.4207(3)
_cell_length_b                   26.1612(11)
_cell_length_c                   11.4892(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.522(4)
_cell_angle_gamma                90
_cell_volume                     1926.22(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.6172
_cell_measurement_theta_min      1.7722
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.3181
_exptl_crystal_size_mid          0.1605
_exptl_crystal_size_min          0.1042
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1271
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28141
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.939
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   -3.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -84.00   -9.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  126.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
  3 omega  -98.00  -50.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  148.0000   15.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega  -94.00  -36.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867 -178.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega    4.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8117   77.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
  6 omega  -40.00   -2.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8117  -57.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega  -46.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8117  -19.0000   30.0000 117

#__ type_ start__ end____ width___ exp.time_
  8 omega  -95.00   -5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
  9 omega  -52.00  -27.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867   38.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega  -99.00   -1.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -38.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
 11 omega   35.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8117  178.0000  120.0000 68

#__ type_ start__ end____ width___ exp.time_
 12 omega   -3.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8117   77.0000  -60.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0165159000
_diffrn_orient_matrix_UB_12      -0.0266707000
_diffrn_orient_matrix_UB_13      0.0066437000
_diffrn_orient_matrix_UB_21      0.0553666000
_diffrn_orient_matrix_UB_22      0.0043601000
_diffrn_orient_matrix_UB_23      0.0544278000
_diffrn_orient_matrix_UB_31      -0.0944387000
_diffrn_orient_matrix_UB_32      -0.0021115000
_diffrn_orient_matrix_UB_33      0.0286144000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2422
_reflns_number_total             3771
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1791
_refine_special_details          
;
 ?
;
_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:
 C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B), C8(H8A,H8B), C12(H12A,H12B),
 C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C15(H15), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.0465(3) 0.08858(8) 0.47945(16) 0.0276(5) Uani 1 1 d . . . . .
O5 O 0.3456(3) 0.16060(8) -0.03694(18) 0.0284(5) Uani 1 1 d . . . . .
O4 O -0.2590(3) 0.08481(9) 0.35744(17) 0.0331(6) Uani 1 1 d . . . . .
C17 C 0.3660(4) 0.13935(10) 0.1628(2) 0.0230(6) Uani 1 1 d . . . . .
H17 H 0.5087 0.1492 0.1674 0.028 Uiso 1 1 calc R . . . .
C18 C 0.2739(4) 0.12280(10) 0.2621(2) 0.0228(6) Uani 1 1 d . . . . .
H18 H 0.3545 0.1220 0.3342 0.027 Uiso 1 1 calc R . . . .
C15 C 0.0442(4) 0.12526(10) 0.0495(2) 0.0235(6) Uani 1 1 d . . . . .
H15 H -0.0349 0.1256 -0.0231 0.028 Uiso 1 1 calc R . . . .
C13 C 0.0644(4) 0.10726(10) 0.2585(2) 0.0230(6) Uani 1 1 d . . . . .
C16 C 0.2509(4) 0.14155(10) 0.0563(2) 0.0225(6) Uani 1 1 d . . . . .
C14 C -0.0458(4) 0.10856(10) 0.1497(2) 0.0224(6) Uani 1 1 d . . . . .
H14 H -0.1872 0.0976 0.1440 0.027 Uiso 1 1 calc R . . . .
B1 B -0.0500(5) 0.09228(12) 0.3698(3) 0.0219(7) Uani 1 1 d . . . . .
O2 O 0.4765(3) 0.08005(7) 0.53466(15) 0.0247(5) Uani 1 1 d . . . . .
N2 N 0.3808(4) 0.06604(10) 0.71653(19) 0.0232(6) Uani 1 1 d . . . . .
C11 C 0.5940(4) 0.05133(11) 0.9040(2) 0.0253(7) Uani 1 1 d . . . . .
H11A H 0.6282 0.0881 0.8982 0.030 Uiso 1 1 calc R . . . .
H11B H 0.5712 0.0438 0.9867 0.030 Uiso 1 1 calc R . . . .
C9 C 0.8408(4) 0.03015(11) 0.7434(2) 0.0249(7) Uani 1 1 d . . . . .
H9A H 0.9682 0.0102 0.7300 0.030 Uiso 1 1 calc R . . . .
H9B H 0.8762 0.0668 0.7363 0.030 Uiso 1 1 calc R . . . .
C10 C 0.7787(5) 0.02005(11) 0.8672(2) 0.0276(7) Uani 1 1 d . . . . .
H10A H 0.7447 -0.0167 0.8744 0.033 Uiso 1 1 calc R . . . .
H10B H 0.9003 0.0273 0.9219 0.033 Uiso 1 1 calc R . . . .
C7 C 0.5027(4) 0.05617(10) 0.6298(2) 0.0220(6) Uani 1 1 d . . . . .
C8 C 0.6727(4) 0.01666(11) 0.6478(2) 0.0238(6) Uani 1 1 d . . . . .
H8A H 0.7404 0.0119 0.5734 0.029 Uiso 1 1 calc R . . . .
H8B H 0.6084 -0.0163 0.6677 0.029 Uiso 1 1 calc R . . . .
C12 C 0.3925(4) 0.04077(11) 0.8307(2) 0.0246(7) Uani 1 1 d . . . . .
H12A H 0.3787 0.0034 0.8188 0.029 Uiso 1 1 calc R . . . .
H12B H 0.2731 0.0522 0.8747 0.029 Uiso 1 1 calc R . . . .
O1 O 0.1103(3) 0.15193(7) 0.76485(16) 0.0276(5) Uani 1 1 d . . . . .
N1 N -0.1189(4) 0.17325(10) 0.6189(2) 0.0303(6) Uani 1 1 d . . . . .
C1 C -0.0242(5) 0.18237(11) 0.7227(2) 0.0247(7) Uani 1 1 d . . . . .
C4 C -0.4710(5) 0.24377(12) 0.7269(3) 0.0345(8) Uani 1 1 d . . . . .
H4A H -0.4402 0.2788 0.7003 0.041 Uiso 1 1 calc R . . . .
H4B H -0.6101 0.2445 0.7596 0.041 Uiso 1 1 calc R . . . .
C3 C -0.3098(5) 0.22923(13) 0.8235(3) 0.0355(8) Uani 1 1 d . . . . .
H3A H -0.3435 0.1947 0.8521 0.043 Uiso 1 1 calc R . . . .
H3B H -0.3213 0.2534 0.8892 0.043 Uiso 1 1 calc R . . . .
C2 C -0.0833(5) 0.22920(11) 0.7884(3) 0.0312(7) Uani 1 1 d . . . . .
H2A H -0.0611 0.2596 0.7394 0.037 Uiso 1 1 calc R . . . .
H2B H 0.0106 0.2323 0.8596 0.037 Uiso 1 1 calc R . . . .
C5 C -0.4813(5) 0.20830(13) 0.6214(3) 0.0397(8) Uani 1 1 d . . . . .
H5A H -0.5941 0.2202 0.5653 0.048 Uiso 1 1 calc R . . . .
H5B H -0.5189 0.1736 0.6472 0.048 Uiso 1 1 calc R . . . .
C6 C -0.2786(5) 0.20496(13) 0.5584(3) 0.0389(8) Uani 1 1 d . . . . .
H6A H -0.3102 0.1908 0.4793 0.047 Uiso 1 1 calc R . . . .
H6B H -0.2223 0.2399 0.5494 0.047 Uiso 1 1 calc R . . . .
H1 H -0.075(5) 0.1423(14) 0.583(3) 0.051(10) Uiso 1 1 d . . . . .
H2 H 0.284(6) 0.0901(14) 0.705(3) 0.047(10) Uiso 1 1 d . . . . .
H3 H 0.188(6) 0.0909(15) 0.488(3) 0.070(13) Uiso 1 1 d . . . . .
H4 H -0.316(7) 0.0800(16) 0.426(4) 0.082(15) Uiso 1 1 d . . . . .
H5 H 0.254(6) 0.1604(15) -0.100(3) 0.062(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 B1 1.373(4) . ?
O3 H3 0.91(4) . ?
O5 C16 1.359(3) . ?
O5 H5 0.91(4) . ?
O4 B1 1.355(4) . ?
O4 H4 0.90(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(4) . ?
C17 C16 1.391(4) . ?
C18 H18 0.9500 . ?
C18 C13 1.404(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(4) . ?
C15 C14 1.389(4) . ?
C13 C14 1.399(4) . ?
C13 B1 1.563(4) . ?
C14 H14 0.9500 . ?
O2 C7 1.261(3) . ?
N2 C7 1.330(3) . ?
N2 C12 1.467(3) . ?
N2 H2 0.89(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.522(4) . ?
C11 C12 1.524(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(4) . ?
C9 C8 1.533(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C7 C8 1.508(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O1 C1 1.250(3) . ?
N1 C1 1.327(4) . ?
N1 C6 1.461(4) . ?
N1 H1 0.96(4) . ?
C1 C2 1.500(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.519(4) . ?
C4 C5 1.525(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.533(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.530(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 O3 H3 119(2) . . ?
C16 O5 H5 109(2) . . ?
B1 O4 H4 113(3) . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C13 121.6(3) . . ?
C13 C18 H18 119.2 . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.6(3) . . ?
C18 C13 B1 123.2(2) . . ?
C14 C13 C18 116.7(2) . . ?
C14 C13 B1 120.0(3) . . ?
O5 C16 C17 118.0(3) . . ?
O5 C16 C15 122.6(3) . . ?
C17 C16 C15 119.3(2) . . ?
C15 C14 C13 122.3(3) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
O3 B1 C13 124.1(3) . . ?
O4 B1 O3 118.3(3) . . ?
O4 B1 C13 117.6(3) . . ?
C7 N2 C12 125.6(3) . . ?
C7 N2 H2 117(2) . . ?
C12 N2 H2 117(2) . . ?
H11A C11 H11B 107.7 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C10 C11 C12 113.5(2) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C10 C9 C8 114.6(2) . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C11 C10 C9 114.8(2) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
O2 C7 N2 120.0(3) . . ?
O2 C7 C8 121.0(2) . . ?
N2 C7 C8 119.0(2) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 C9 114.3(2) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N2 C12 C11 114.0(2) . . ?
N2 C12 H12A 108.7 . . ?
N2 C12 H12B 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C1 N1 C6 126.6(3) . . ?
C1 N1 H1 114(2) . . ?
C6 N1 H1 119(2) . . ?
O1 C1 N1 120.1(3) . . ?
O1 C1 C2 121.1(3) . . ?
N1 C1 C2 118.9(3) . . ?
H4A C4 H4B 107.5 . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C3 C4 C5 115.0(3) . . ?
C5 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C4 C3 C2 115.0(3) . . ?
H3A C3 H3B 107.5 . . ?
C2 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C1 C2 C3 114.0(2) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.6 . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C4 C5 C6 114.5(3) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
N1 C6 C5 113.5(3) . . ?
N1 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?

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
C18 C13 B1 O3 -5.8(4) . . . . ?
C18 C13 B1 O4 171.0(3) . . . . ?
C14 C13 B1 O3 178.1(3) . . . . ?
C14 C13 B1 O4 -5.0(4) . . . . ?
C11 C10 C9 C8 -62.8(3) . . . . ?
C11 C12 N2 C7 65.6(4) . . . . ?
C9 C10 C11 C12 62.1(3) . . . . ?
C9 C8 C7 O2 116.2(3) . . . . ?
C9 C8 C7 N2 -63.1(3) . . . . ?
C10 C11 C12 N2 -78.3(3) . . . . ?
C10 C9 C8 C7 79.3(3) . . . . ?
C8 C7 N2 C12 -1.5(4) . . . . ?
C12 N2 C7 O2 179.2(2) . . . . ?
C1 C2 C3 C4 -79.4(3) . . . . ?
C4 C5 C6 N1 76.6(4) . . . . ?
C3 C4 C5 C6 -60.6(4) . . . . ?
C3 C2 C1 O1 -115.1(3) . . . . ?
C3 C2 C1 N1 64.1(4) . . . . ?
C2 C1 N1 C6 0.7(4) . . . . ?
C2 C3 C4 C5 61.4(4) . . . . ?
C5 C6 N1 C1 -64.5(4) . . . . ?
C6 N1 C1 O1 179.9(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 36 3 0.0396 -1.0082 36.0108 2.9940 -0.9572 0.2641 0.1048
6 24 -6 0.0774 5.9883 24.0103 -6.0095 -0.5814 0.1092 -0.7882
0 -37 -2 0.0557 0.0093 -37.0117 -1.9930 0.9740 -0.2693 0.0202
-6 -3 12 0.0648 -5.9909 -2.9997 12.0065 0.0608 0.3087 0.9157
2 4 -16 0.0742 1.9896 3.9908 -16.0050 -0.1799 -0.7436 -0.6543
8 2 -7 0.0938 7.9933 2.0064 -7.0065 0.0320 0.0700 -0.9596
5 -6 12 0.1157 5.0068 -5.9845 12.0004 0.3220 0.9043 -0.1168
-7 5 -8 0.1854 -7.0038 4.9846 -7.9983 -0.3018 -0.8014 0.4220

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2xB(OH)3_15srv189
_database_code_depnum_ccdc_archive 'CCDC 1568424'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;
_audit_creation_date             2015-07-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'B H3 O3, C6 H11 N O'
_chemical_formula_sum            'C6 H14 B N O4'
_chemical_formula_weight         174.99
_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/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                   6.9008(3)
_cell_length_b                   18.7679(8)
_cell_length_c                   7.4385(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.3340(14)
_cell_angle_gamma                90.00
_cell_volume                     897.37(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.89
_cell_measurement_theta_min      3.13
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0673 before and 0.0372 after correction.
The Ratio of minimum to maximum transmission is 0.9671.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19366
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.17
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2218
_reflns_number_total             2628
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.056
_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)+(0.0470P)²+0.1900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0903
_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    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.59418(9) 0.08124(3) 0.06364(10) 0.01691(14) Uani 1 d . . .
O2 O 0.92245(10) 0.09766(3) 0.03819(10) 0.01694(15) Uani 1 d . . .
O3 O 0.76309(10) -0.01626(3) -0.01621(10) 0.01823(15) Uani 1 d . . .
B1 B 0.76075(14) 0.05431(5) 0.02922(13) 0.01327(18) Uani 1 d . . .
H1A H 0.602(2) 0.1268(9) 0.093(2) 0.046(4) Uiso 1 d . . .
H2 H 1.022(2) 0.0746(8) 0.027(2) 0.038(4) Uiso 1 d . . .
H3 H 0.649(3) -0.0373(8) -0.029(2) 0.044(4) Uiso 1 d . . .
O4 O 0.57595(11) 0.21347(4) 0.14259(12) 0.02583(18) Uani 1 d . . .
N1 N 0.86158(12) 0.25481(4) 0.09818(12) 0.01850(17) Uani 1 d . . .
C1 C 0.69482(14) 0.26392(4) 0.14613(13) 0.01724(18) Uani 1 d . . .
C2 C 0.64953(15) 0.33693(5) 0.20538(14) 0.01867(18) Uani 1 d . . .
C3 C 0.59863(16) 0.39316(5) 0.04497(15) 0.0234(2) Uani 1 d . . .
C4 C 0.78878(18) 0.42390(5) 0.01481(16) 0.0257(2) Uani 1 d . . .
C5 C 0.91773(17) 0.37005(5) -0.04724(15) 0.0253(2) Uani 1 d . . .
C6 C 1.01074(15) 0.31020(5) 0.09657(15) 0.02132(19) Uani 1 d . . .
H1 H 0.886(2) 0.2119(7) 0.0704(19) 0.028(3) Uiso 1 d . . .
H2A H 0.769(2) 0.3517(7) 0.3151(19) 0.026(3) Uiso 1 d . . .
H2B H 0.530(2) 0.3313(6) 0.2457(18) 0.023(3) Uiso 1 d . . .
H3A H 0.504(2) 0.3728(7) -0.0768(19) 0.029(3) Uiso 1 d . . .
H3B H 0.521(2) 0.4336(7) 0.0803(19) 0.032(3) Uiso 1 d . . .
H4A H 0.879(2) 0.4472(7) 0.139(2) 0.030(3) Uiso 1 d . . .
H4B H 0.742(2) 0.4618(8) -0.087(2) 0.037(4) Uiso 1 d . . .
H5A H 0.834(2) 0.3488(7) -0.172(2) 0.032(3) Uiso 1 d . . .
H5B H 1.036(2) 0.3946(8) -0.0635(19) 0.034(3) Uiso 1 d . . .
H6A H 1.116(2) 0.2854(7) 0.0651(18) 0.023(3) Uiso 1 d . . .
H6B H 1.078(2) 0.3296(7) 0.2281(19) 0.026(3) Uiso 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 B1 1.3625(11) . ?
O1 H1A 0.879(17) . ?
O2 B1 1.3628(10) . ?
O2 H2 0.841(15) . ?
O3 B1 1.3685(11) . ?
O3 H3 0.852(16) . ?
O4 C1 1.2468(11) . ?
N1 C1 1.3339(11) . ?
N1 C6 1.4660(12) . ?
N1 H1 0.863(14) . ?
C1 C2 1.5066(12) . ?
C2 C3 1.5348(13) . ?
C2 H2A 0.965(13) . ?
C2 H2B 0.980(12) . ?
C3 C4 1.5229(15) . ?
C3 H3A 0.982(13) . ?
C3 H3B 1.019(14) . ?
C4 C5 1.5249(14) . ?
C4 H4A 1.004(14) . ?
C4 H4B 1.003(15) . ?
C5 C6 1.5226(14) . ?
C5 H5A 0.984(14) . ?
C5 H5B 0.982(15) . ?
C6 H6A 0.960(13) . ?
C6 H6B 0.987(13) . ?

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 H1A 115.4(10) . . ?
B1 O2 H2 111.8(10) . . ?
B1 O3 H3 112.5(10) . . ?
O1 B1 O2 120.07(8) . . ?
O1 B1 O3 119.47(8) . . ?
O2 B1 O3 120.45(8) . . ?
C1 N1 C6 126.01(8) . . ?
C1 N1 H1 116.6(9) . . ?
C6 N1 H1 117.4(9) . . ?
O4 C1 N1 121.47(8) . . ?
O4 C1 C2 119.47(8) . . ?
N1 C1 C2 119.06(8) . . ?
C1 C2 C3 114.27(8) . . ?
C1 C2 H2A 107.7(8) . . ?
C1 C2 H2B 106.1(7) . . ?
C3 C2 H2A 110.1(8) . . ?
C3 C2 H2B 109.4(7) . . ?
H2A C2 H2B 109.0(10) . . ?
C2 C3 H3A 109.7(8) . . ?
C2 C3 H3B 107.7(8) . . ?
C4 C3 C2 114.16(8) . . ?
C4 C3 H3A 109.5(8) . . ?
C4 C3 H3B 108.7(8) . . ?
H3A C3 H3B 106.8(11) . . ?
C3 C4 C5 114.98(8) . . ?
C3 C4 H4A 107.9(7) . . ?
C3 C4 H4B 109.0(8) . . ?
C5 C4 H4A 109.4(8) . . ?
C5 C4 H4B 107.6(8) . . ?
H4A C4 H4B 107.8(11) . . ?
C4 C5 H5A 110.4(8) . . ?
C4 C5 H5B 109.2(8) . . ?
C6 C5 C4 114.81(8) . . ?
C6 C5 H5A 108.6(8) . . ?
C6 C5 H5B 106.0(8) . . ?
H5A C5 H5B 107.5(11) . . ?
N1 C6 C5 114.27(8) . . ?
N1 C6 H6A 104.7(8) . . ?
N1 C6 H6B 109.4(7) . . ?
C5 C6 H6A 110.5(8) . . ?
C5 C6 H6B 110.5(7) . . ?
H6A C6 H6B 107.2(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O4 0.879(17) 1.692(17) 2.5638(9) 171.0(15) .
O2 H2 O3 0.841(15) 1.868(15) 2.7070(9) 174.5(14) 3_755
O3 H3 O1 0.852(16) 1.805(17) 2.6565(9) 178.4(15) 3_655
N1 H1 O2 0.863(14) 2.183(14) 3.0349(10) 169.4(12) .

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 C1 C2 C3 -115.43(10) . . . . ?
N1 C1 C2 C3 64.45(12) . . . . ?
C1 N1 C6 C5 -63.19(12) . . . . ?
C1 C2 C3 C4 -79.74(10) . . . . ?
C2 C3 C4 C5 62.10(12) . . . . ?
C3 C4 C5 C6 -61.34(12) . . . . ?
C4 C5 C6 N1 76.46(11) . . . . ?
C6 N1 C1 O4 179.76(9) . . . . ?
C6 N1 C1 C2 -0.11(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ap68_13a
_database_code_depnum_ccdc_archive 'CCDC 1568426'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;
_audit_creation_date             2014-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H7 B O3'
_chemical_formula_sum            'C6 H7 B O3'
_chemical_formula_weight         137.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H7BO3
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'
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                   14.3765(4)
_cell_length_b                   5.04525(19)
_cell_length_c                   17.3563(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.695(3)
_cell_angle_gamma                90.00
_cell_volume                     1258.81(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3477
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.6500
_cell_measurement_theta_min      1.8248
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             576.000
_exptl_crystal_recrystallization_method 
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.4094
_exptl_crystal_size_mid          0.1855
_exptl_crystal_size_min          0.1143
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15899
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.35
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 16.1511
_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  -27.00   42.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  -57.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega   43.00  103.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -178.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega   12.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -100.0000  150.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega   37.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -100.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   25.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679   77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679   38.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
  7 omega  -46.00   71.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  -19.0000   90.0000 117

#__ type_ start__ end____ width___ exp.time_
  8 omega  -99.00   -1.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -38.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
  9 omega -102.00  -63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429 -178.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
 10 omega    7.00   96.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679   57.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
 11 omega   -3.00   97.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679   77.0000  150.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0187688000
_diffrn_orient_matrix_UB_12      -0.1069538000
_diffrn_orient_matrix_UB_13      0.0216623000
_diffrn_orient_matrix_UB_21      -0.0229261000
_diffrn_orient_matrix_UB_22      -0.0912438000
_diffrn_orient_matrix_UB_23      -0.0248938000
_diffrn_orient_matrix_UB_31      0.0394272000
_diffrn_orient_matrix_UB_32      -0.0020303000
_diffrn_orient_matrix_UB_33      -0.0241371000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2036
_reflns_number_total             2475
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.088
_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)+(0.0516P)²+1.0331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1255
_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
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C2(H2), C3(H3A), C5(H5), C11(H11), C12(H12), C6(H6)
2.b Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6A), O1(H1), O2(H2A)
;
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.17239(10) 0.1971(3) 0.23738(9) 0.0231(4) Uani 1 1 d . . . . .
H5 H 0.207040 0.330910 0.235207 0.035 Uiso 1 1 calc GR . . . .
O6 O 0.19155(10) -0.2584(3) 0.21834(9) 0.0230(4) Uani 1 1 d . . . . .
H6 H 0.140183 -0.230537 0.196217 0.034 Uiso 1 1 calc GR . . . .
O4 O 0.57280(10) 0.0222(3) 0.41451(9) 0.0217(4) Uani 1 1 d . . . . .
O1 O 1.02595(10) 0.7602(3) 0.63785(10) 0.0270(4) Uani 1 1 d . . . . .
H1 H 0.990314 0.891562 0.633989 0.041 Uiso 1 1 calc GR . . . .
O3 O 0.66137(10) 0.5246(3) 0.41548(9) 0.0228(4) Uani 1 1 d . . . . .
C9 C 0.38926(13) -0.2074(4) 0.28149(11) 0.0157(4) Uani 1 1 d . . . . .
H9 H 0.378095 -0.346893 0.245801 0.019 Uiso 1 1 calc R . . . .
C8 C 0.47366(13) -0.1985(4) 0.32112(11) 0.0170(4) Uani 1 1 d . . . . .
H8 H 0.520155 -0.327881 0.311644 0.020 Uiso 1 1 calc R . . . .
C2 C 0.82460(13) 0.3283(4) 0.56918(11) 0.0165(4) Uani 1 1 d . . . . .
H2 H 0.832686 0.190549 0.605986 0.020 Uiso 1 1 calc R . . . .
C7 C 0.48951(13) 0.0014(4) 0.37477(11) 0.0162(4) Uani 1 1 d . . . . .
C3 C 0.74719(13) 0.3230(4) 0.52081(11) 0.0174(4) Uani 1 1 d . . . . .
H3A H 0.701882 0.187155 0.525604 0.021 Uiso 1 1 calc R . . . .
C5 C 0.80181(13) 0.7208(4) 0.45922(11) 0.0182(4) Uani 1 1 d . . . . .
H5A H 0.794632 0.853893 0.420903 0.022 Uiso 1 1 calc R . . . .
O2 O 1.00572(10) 0.3048(3) 0.65715(9) 0.0248(4) Uani 1 1 d . . . . .
H2A H 1.058558 0.327989 0.677221 0.037 Uiso 1 1 calc GR . . . .
C10 C 0.32013(13) -0.0161(4) 0.29274(11) 0.0156(4) Uani 1 1 d . . . . .
C1 C 0.89134(13) 0.5303(4) 0.56550(11) 0.0160(4) Uani 1 1 d . . . . .
C11 C 0.33893(13) 0.1826(4) 0.34715(11) 0.0171(4) Uani 1 1 d . . . . .
H11 H 0.293355 0.315302 0.355868 0.021 Uiso 1 1 calc R . . . .
C12 C 0.42200(13) 0.1920(4) 0.38875(11) 0.0174(4) Uani 1 1 d . . . . .
H12 H 0.432504 0.326546 0.426147 0.021 Uiso 1 1 calc R . . . .
C4 C 0.73679(13) 0.5189(4) 0.46533(11) 0.0166(4) Uani 1 1 d . . . . .
C6 C 0.87730(13) 0.7262(4) 0.50956(12) 0.0170(4) Uani 1 1 d . . . . .
H6A H 0.920824 0.867251 0.505963 0.020 Uiso 1 1 calc R . . . .
B2 B 0.22565(15) -0.0253(4) 0.24732(13) 0.0155(5) Uani 1 1 d . . . . .
B1 B 0.97717(15) 0.5333(5) 0.62189(13) 0.0175(5) Uani 1 1 d . . . . .
H3 H 0.6369(18) 0.372(6) 0.4183(15) 0.035(7) Uiso 1 1 d . . . . .
H4 H 0.602(2) -0.132(7) 0.4138(17) 0.050(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 H5 0.8400 . ?
O5 B2 1.368(3) . ?
O6 H6 0.8400 . ?
O6 B2 1.368(3) . ?
O4 C7 1.379(2) . ?
O4 H4 0.88(3) . ?
O1 H1 0.8400 . ?
O1 B1 1.369(3) . ?
O3 C4 1.379(2) . ?
O3 H3 0.85(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.388(3) . ?
C9 C10 1.401(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.390(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C2 C1 1.402(3) . ?
C7 C12 1.390(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.387(3) . ?
C5 H5A 0.9500 . ?
C5 C4 1.387(3) . ?
C5 C6 1.385(3) . ?
O2 H2A 0.8400 . ?
O2 B1 1.366(3) . ?
C10 C11 1.402(3) . ?
C10 B2 1.563(3) . ?
C1 C6 1.399(3) . ?
C1 B1 1.566(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 H12 0.9500 . ?
C6 H6A 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
B2 O5 H5 109.5 . . ?
B2 O6 H6 109.5 . . ?
C7 O4 H4 109.8(19) . . ?
B1 O1 H1 109.5 . . ?
C4 O3 H3 105.6(18) . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.75(18) . . ?
C10 C9 H9 119.1 . . ?
C9 C8 H8 120.3 . . ?
C9 C8 C7 119.38(18) . . ?
C7 C8 H8 120.3 . . ?
C3 C2 H2 119.0 . . ?
C3 C2 C1 122.08(19) . . ?
C1 C2 H2 119.0 . . ?
O4 C7 C8 121.66(17) . . ?
O4 C7 C12 117.66(18) . . ?
C8 C7 C12 120.67(17) . . ?
C2 C3 H3A 120.5 . . ?
C2 C3 C4 119.08(18) . . ?
C4 C3 H3A 120.5 . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C6 C5 C4 119.34(18) . . ?
B1 O2 H2A 109.5 . . ?
C9 C10 C11 117.10(17) . . ?
C9 C10 B2 121.55(17) . . ?
C11 C10 B2 121.35(17) . . ?
C2 C1 B1 120.87(18) . . ?
C6 C1 C2 116.90(17) . . ?
C6 C1 B1 122.23(18) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.15(18) . . ?
C12 C11 H11 118.9 . . ?
C7 C12 H12 120.5 . . ?
C11 C12 C7 118.93(18) . . ?
C11 C12 H12 120.5 . . ?
O3 C4 C3 121.84(18) . . ?
O3 C4 C5 117.53(18) . . ?
C3 C4 C5 120.61(18) . . ?
C5 C6 C1 121.95(18) . . ?
C5 C6 H6A 119.0 . . ?
C1 C6 H6A 119.0 . . ?
O5 B2 C10 121.40(18) . . ?
O6 B2 O5 117.48(17) . . ?
O6 B2 C10 121.08(18) . . ?
O1 B1 C1 122.16(19) . . ?
O2 B1 O1 117.69(18) . . ?
O2 B1 C1 120.16(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O6 0.84 2.10 2.781(2) 137.4 1_565 yes
O6 H6 O1 0.84 1.92 2.746(2) 165.3 4_465 yes
O1 H1 O2 0.84 2.13 2.784(2) 134.0 1_565 yes
O2 H2A O5 0.84 1.93 2.757(2) 165.8 4_666 yes
O3 H3 O4 0.85(3) 1.99(3) 2.836(2) 174(3) . yes
O4 H4 O3 0.88(3) 1.93(3) 2.815(2) 177(3) 1_545 yes

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
C9 C10 B2 O5 -157.46(19) . . . . ?
C9 C10 B2 O6 24.9(3) . . . . ?
C2 C1 B1 O1 -158.25(19) . . . . ?
C2 C1 B1 O2 21.7(3) . . . . ?
C11 C10 B2 O5 23.2(3) . . . . ?
C11 C10 B2 O6 -154.44(19) . . . . ?
C6 C1 B1 O1 21.8(3) . . . . ?
C6 C1 B1 O2 -158.32(19) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 7 2 0.1975 -1.9986 6.9995 2.0001 -0.7428 -0.6426 -0.1413
18 1 12 0.0308 17.9996 1.0000 11.9997 0.4908 -0.8026 0.4180
-16 -1 -14 0.0793 -15.9997 -1.0000 -13.9997 -0.4966 0.8066 -0.2909
16 1 -15 0.0478 15.9989 1.0001 -15.0004 -0.1316 -0.0846 0.9908
-1 -7 0 0.1803 -1.0012 -6.9995 0.0000 0.7298 0.6616 -0.0253
-16 0 15 0.0590 -15.9987 -0.0002 15.0004 0.0247 -0.0066 -0.9928

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 700 Series'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perflourotether oil'
_olex2_submission_special_instructions 'No special instructions were received'

