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

####################################################################### 
# 
# 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_73herbm
_database_code_depnum_ccdc_archive 'CCDC 1024934'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 B2 O4, 2(C5 H9 N O2)'
_chemical_formula_sum            'C16 H26 B2 N2 O8'
_chemical_formula_weight         396.01

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.8940(11)
_cell_length_b                   7.6323(12)
_cell_length_c                   9.9174(15)
_cell_angle_alpha                79.286(2)
_cell_angle_beta                 71.221(2)
_cell_angle_gamma                81.683(2)
_cell_volume                     483.41(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2840
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.19

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             210
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4711
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1696
_reflns_number_gt                1575
_reflns_threshold_expression     >2sigma(I)

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

_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.
 
 Due to the absence of heavy atoms, the data have been merged for the 
 refinement.
 O-H and N-H hydrogens have been located from iterative examination of 
 difference Fourier maps following least squares refinements of the 
 previous models with the following restraints:
 DFIX 0.84 0.01 for O-H and DFIX 0.86 0.01 for N-H
 Isotropic displacement parameters of these H atoms were set to
 Uiso=1.5Ueq(C) or  1.5Ueq (O,N).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0515P)²+0.0401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1696
_refine_ls_number_parameters     277
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7776(7) 0.4117(7) 0.5124(6) 0.0374(12) Uani 1 1 d . . .
B2 B 0.0870(7) 0.1400(6) 1.0205(5) 0.0307(10) Uani 1 1 d . . .
O1 O 0.7351(4) 0.5293(5) 0.4038(4) 0.0559(9) Uani 1 1 d D . .
H1' H 0.841(5) 0.559(8) 0.336(5) 0.084 Uiso 1 1 d D . .
O2 O 0.9748(4) 0.3538(4) 0.5121(3) 0.0476(8) Uani 1 1 d D . .
H2' H 1.071(6) 0.414(6) 0.459(5) 0.071 Uiso 1 1 d D . .
O3 O 0.1158(4) 0.0877(4) 1.1507(3) 0.0464(8) Uani 1 1 d D . .
H3' H 0.007(5) 0.068(7) 1.218(4) 0.070 Uiso 1 1 d D . .
O4 O -0.0891(4) 0.1294(5) 0.9940(3) 0.0587(10) Uani 1 1 d D . .
H4' H -0.187(6) 0.091(8) 1.064(4) 0.088 Uiso 1 1 d D . .
C1 C 0.5962(6) 0.3438(6) 0.6471(5) 0.0322(9) Uani 1 1 d . . .
C2 C 0.6337(6) 0.2401(5) 0.7698(5) 0.0375(10) Uani 1 1 d . . .
H2 H 0.7687 0.2104 0.7715 0.045 Uiso 1 1 calc R . .
C3 C 0.4746(6) 0.1812(5) 0.8882(5) 0.0349(10) Uani 1 1 d . . .
H3 H 0.5048 0.1161 0.9693 0.042 Uiso 1 1 calc R . .
C4 C 0.2701(6) 0.2164(5) 0.8898(4) 0.0327(10) Uani 1 1 d . . .
C5 C 0.2326(6) 0.3201(5) 0.7672(4) 0.0343(10) Uani 1 1 d . . .
H5 H 0.0979 0.3456 0.7641 0.041 Uiso 1 1 calc R . .
C6 C 0.3911(6) 0.3855(5) 0.6505(5) 0.0348(10) Uani 1 1 d . . .
H6 H 0.3603 0.4588 0.5726 0.042 Uiso 1 1 calc R . .
N1 N 1.6048(4) 0.6520(4) 0.1347(3) 0.0408(9) Uani 1 1 d D . .
H1A H 1.586(8) 0.571(5) 0.209(3) 0.061 Uiso 1 1 d D . .
H1B H 1.631(7) 0.748(4) 0.157(5) 0.061 Uiso 1 1 d D . .
N2 N 0.2241(4) 1.0347(5) 0.4184(3) 0.0406(9) Uani 1 1 d D . .
H2A H 0.268(7) 1.026(7) 0.3281(13) 0.061 Uiso 1 1 d D . .
H2B H 0.139(6) 1.129(4) 0.433(5) 0.061 Uiso 1 1 d D . .
O5 O 1.0653(5) 0.6287(5) 0.1892(4) 0.0638(11) Uani 1 1 d . . .
O6 O 1.2838(5) 0.4911(5) 0.3065(3) 0.0572(9) Uani 1 1 d . . .
O7 O 0.7690(5) 1.0366(6) 0.3615(4) 0.0631(11) Uani 1 1 d . . .
O8 O 0.5935(4) 0.9848(4) 0.2214(3) 0.0408(7) Uani 1 1 d . . .
C7 C 1.2364(7) 0.5968(6) 0.2067(5) 0.0403(10) Uani 1 1 d . . .
C8 C 1.4085(6) 0.6974(6) 0.0985(4) 0.0346(9) Uani 1 1 d . . .
H8 H 1.3696 0.8260 0.0992 0.042 Uiso 1 1 calc R . .
C9 C 1.4612(8) 0.6604(8) -0.0547(6) 0.0578(14) Uani 1 1 d . . .
H9A H 1.4259 0.5422 -0.0558 0.069 Uiso 1 1 calc R . .
H9B H 1.3873 0.7486 -0.1087 0.069 Uiso 1 1 calc R . .
C10 C 1.6883(8) 0.6718(8) -0.1178(6) 0.0573(14) Uani 1 1 d . . .
H10A H 1.7203 0.7951 -0.1515 0.069 Uiso 1 1 calc R . .
H10B H 1.7457 0.6033 -0.1971 0.069 Uiso 1 1 calc R . .
C11 C 1.7669(8) 0.5922(9) 0.0069(6) 0.0688(16) Uani 1 1 d . . .
H11A H 1.7849 0.4626 0.0159 0.083 Uiso 1 1 calc R . .
H11B H 1.8974 0.6361 -0.0046 0.083 Uiso 1 1 calc R . .
C12 C 0.6097(6) 1.0215(5) 0.3349(5) 0.0353(10) Uani 1 1 d . . .
C13 C 0.4144(6) 1.0480(5) 0.4586(4) 0.0349(9) Uani 1 1 d . . .
H13 H 0.4069 1.1672 0.4843 0.042 Uiso 1 1 calc R . .
C14 C 0.4003(7) 0.9103(7) 0.5924(5) 0.0452(11) Uani 1 1 d . . .
H14A H 0.4938 0.8047 0.5692 0.054 Uiso 1 1 calc R . .
H14B H 0.4339 0.9596 0.6646 0.054 Uiso 1 1 calc R . .
C15 C 0.1806(7) 0.8647(7) 0.6457(5) 0.0498(12) Uani 1 1 d . . .
H15A H 0.0926 0.9513 0.7042 0.060 Uiso 1 1 calc R . .
H15B H 0.1689 0.7462 0.7020 0.060 Uiso 1 1 calc R . .
C16 C 0.1252(8) 0.8720(7) 0.5094(6) 0.0596(13) Uani 1 1 d . . .
H16A H 0.1819 0.7653 0.4649 0.071 Uiso 1 1 calc R . .
H16B H -0.0227 0.8866 0.5274 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.032(3) 0.039(3) 0.043(3) -0.001(2) -0.016(2) -0.0078(19)
B2 0.029(2) 0.032(2) 0.031(3) -0.0011(18) -0.012(2) -0.0013(18)
O1 0.0252(16) 0.079(2) 0.050(2) 0.0231(17) -0.0113(14) -0.0058(15)
O2 0.0297(16) 0.060(2) 0.0472(19) 0.0144(15) -0.0134(14) -0.0087(13)
O3 0.0258(16) 0.076(2) 0.0327(19) 0.0017(15) -0.0070(13) -0.0086(15)
O4 0.0338(18) 0.100(3) 0.0369(18) 0.0171(17) -0.0101(14) -0.0271(17)
C1 0.029(2) 0.036(2) 0.033(2) -0.0087(17) -0.0103(17) -0.0019(16)
C2 0.027(2) 0.043(2) 0.042(3) 0.004(2) -0.013(2) -0.0047(17)
C3 0.030(2) 0.040(2) 0.033(2) 0.0045(18) -0.0127(19) -0.0038(17)
C4 0.034(2) 0.031(2) 0.035(2) -0.0019(17) -0.0133(19) -0.0083(18)
C5 0.020(2) 0.042(2) 0.037(2) -0.0027(19) -0.0079(19) 0.0020(17)
C6 0.032(2) 0.037(2) 0.031(2) 0.0008(17) -0.0093(19) 0.0001(17)
N1 0.0369(19) 0.049(2) 0.038(2) -0.0023(17) -0.0126(17) -0.0095(16)
N2 0.0288(18) 0.058(2) 0.034(2) -0.0103(18) -0.0115(16) 0.0084(16)
O5 0.0334(18) 0.100(3) 0.048(2) 0.0202(19) -0.0131(15) -0.0129(18)
O6 0.0419(18) 0.077(2) 0.044(2) 0.0174(17) -0.0115(15) -0.0153(16)
O7 0.0329(17) 0.123(3) 0.0366(19) -0.0119(19) -0.0079(14) -0.0242(17)
O8 0.0364(16) 0.0557(18) 0.0285(15) -0.0068(13) -0.0058(12) -0.0076(13)
C7 0.031(2) 0.055(3) 0.030(2) -0.001(2) -0.0049(19) -0.0055(19)
C8 0.031(2) 0.035(2) 0.036(2) -0.0028(17) -0.0082(17) -0.0029(16)
C9 0.051(3) 0.079(4) 0.044(3) -0.005(3) -0.013(3) -0.018(3)
C10 0.047(3) 0.081(4) 0.046(3) -0.024(3) -0.006(2) -0.015(3)
C11 0.043(3) 0.100(4) 0.059(3) -0.031(3) -0.004(2) 0.008(3)
C12 0.034(2) 0.039(2) 0.030(3) 0.0010(18) -0.0100(19) -0.0046(18)
C13 0.038(2) 0.036(2) 0.034(2) -0.0091(17) -0.0128(17) -0.0039(17)
C14 0.037(2) 0.069(3) 0.027(2) -0.001(2) -0.009(2) -0.004(2)
C15 0.038(2) 0.059(3) 0.040(3) 0.002(2) -0.003(2) 0.000(2)
C16 0.049(3) 0.070(3) 0.061(3) 0.000(3) -0.019(3) -0.015(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.349(6) . ?
B1 O2 1.366(6) . ?
B1 C1 1.572(6) . ?
B2 O4 1.339(6) . ?
B2 O3 1.349(6) . ?
B2 C4 1.578(6) . ?
C1 C6 1.395(5) . ?
C1 C2 1.399(6) . ?
C2 C3 1.379(5) . ?
C3 C4 1.392(5) . ?
C4 C5 1.399(6) . ?
C5 C6 1.383(6) . ?
N1 C8 1.486(5) . ?
N1 C11 1.490(6) . ?
N2 C16 1.501(6) . ?
N2 C13 1.510(5) . ?
O5 C7 1.230(5) . ?
O6 C7 1.254(5) . ?
O7 C12 1.234(5) . ?
O8 C12 1.251(5) . ?
C7 C8 1.512(6) . ?
C8 C9 1.515(6) . ?
C9 C10 1.496(7) . ?
C10 C11 1.500(7) . ?
C12 C13 1.519(6) . ?
C13 C14 1.518(6) . ?
C14 C15 1.504(6) . ?
C15 C16 1.509(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 O2 122.1(4) . . ?
O1 B1 C1 119.5(4) . . ?
O2 B1 C1 118.3(4) . . ?
O4 B2 O3 123.7(4) . . ?
O4 B2 C4 117.2(4) . . ?
O3 B2 C4 119.1(3) . . ?
C6 C1 C2 117.0(4) . . ?
C6 C1 B1 121.6(4) . . ?
C2 C1 B1 121.3(3) . . ?
C3 C2 C1 121.4(4) . . ?
C2 C3 C4 121.8(4) . . ?
C3 C4 C5 116.8(4) . . ?
C3 C4 B2 122.5(3) . . ?
C5 C4 B2 120.6(3) . . ?
C6 C5 C4 121.5(3) . . ?
C5 C6 C1 121.4(4) . . ?
C8 N1 C11 108.4(4) . . ?
C16 N2 C13 107.7(3) . . ?
O5 C7 O6 126.9(4) . . ?
O5 C7 C8 117.1(4) . . ?
O6 C7 C8 115.9(4) . . ?
N1 C8 C7 111.8(3) . . ?
N1 C8 C9 104.7(3) . . ?
C7 C8 C9 115.0(3) . . ?
C10 C9 C8 105.5(4) . . ?
C9 C10 C11 102.8(4) . . ?
N1 C11 C10 104.4(4) . . ?
O7 C12 O8 127.7(4) . . ?
O7 C12 C13 114.1(4) . . ?
O8 C12 C13 118.2(4) . . ?
N2 C13 C14 104.9(3) . . ?
N2 C13 C12 111.9(3) . . ?
C14 C13 C12 114.2(3) . . ?
C15 C14 C13 105.1(3) . . ?
C14 C15 C16 103.7(4) . . ?
N2 C16 C15 101.7(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
O1 B1 C1 C6 7.5(6) . . . . ?
O2 B1 C1 C6 -174.8(4) . . . . ?
O1 B1 C1 C2 -171.8(4) . . . . ?
O2 B1 C1 C2 5.8(6) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
B1 C1 C2 C3 179.7(4) . . . . ?
C1 C2 C3 C4 2.2(6) . . . . ?
C2 C3 C4 C5 -2.1(6) . . . . ?
C2 C3 C4 B2 176.1(4) . . . . ?
O4 B2 C4 C3 -158.1(4) . . . . ?
O3 B2 C4 C3 21.2(6) . . . . ?
O4 B2 C4 C5 20.0(6) . . . . ?
O3 B2 C4 C5 -160.7(4) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
B2 C4 C5 C6 -178.8(4) . . . . ?
C4 C5 C6 C1 3.1(6) . . . . ?
C2 C1 C6 C5 -3.0(6) . . . . ?
B1 C1 C6 C5 177.7(4) . . . . ?
C11 N1 C8 C7 125.7(4) . . . . ?
C11 N1 C8 C9 0.5(5) . . . . ?
O5 C7 C8 N1 177.9(4) . . . . ?
O6 C7 C8 N1 -1.0(5) . . . . ?
O5 C7 C8 C9 -63.0(5) . . . . ?
O6 C7 C8 C9 118.2(5) . . . . ?
N1 C8 C9 C10 -23.2(5) . . . . ?
C7 C8 C9 C10 -146.3(4) . . . . ?
C8 C9 C10 C11 36.7(5) . . . . ?
C8 N1 C11 C10 22.1(6) . . . . ?
C9 C10 C11 N1 -35.9(6) . . . . ?
C16 N2 C13 C14 -10.1(4) . . . . ?
C16 N2 C13 C12 114.3(4) . . . . ?
O7 C12 C13 N2 177.9(4) . . . . ?
O8 C12 C13 N2 -3.3(5) . . . . ?
O7 C12 C13 C14 -63.1(5) . . . . ?
O8 C12 C13 C14 115.7(4) . . . . ?
N2 C13 C14 C15 -15.8(4) . . . . ?
C12 C13 C14 C15 -138.6(4) . . . . ?
C13 C14 C15 C16 35.7(5) . . . . ?
C13 N2 C16 C15 31.6(5) . . . . ?
C14 C15 C16 N2 -41.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_?
_database_code_depnum_ccdc_archive 'CCDC 1024935'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;

loop_
_audit_conform_dict_name
_audit_conform_dict_version
_audit_conform_dict_location
cif_core.dic . ftp://ftp.iucr.org/pub/cif_core.dic
cif_pd.dic . ftp://ftp.iucr.org/pub/cif_pd.dic

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            
'cocrystal (I) of 4-iodophenylboronic acid with L-proline (1:1)'
_chemical_formula_moiety         'C6 H6 B I O2, C5 H9 N O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C11 H15 B I N O4'
_chemical_formula_weight         362.95
_chemical_melting_point          ?
_chemical_compound_source        'see text'
_chemical_properties_physical    moisture-sensitive
_exptl_crystal_recrystallization_method 
'Solvent assisted grinding: methanol, ethanol, acetonitrile, acet., acetone-water, 2-propanol and THF'

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'
I I -0.3257 6.8362 ' 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'

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   13.493(6)
_cell_length_b                   7.8123(33)
_cell_length_c                   6.5850(27)
_cell_angle_alpha                90
_cell_angle_beta                 100.2942(21)
_cell_angle_gamma                90
_cell_volume                     683.0(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'Not Measured'
_cell_special_details            
; ?
;

_pd_spec_size_axial              10 # perpendicular to 
# equatorial plane
_pd_spec_size_equat              10 # parallel to 
# scattering vector 
# in transmission
_pd_spec_size_thick              ? # perpendicular to 
# scattering vector 
# in transmission

_pd_spec_mounting                'Packed between thin slides of cellophane'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   flat_sheet
_pd_char_particle_morphology     'white powder (visual)'
_pd_char_colour                  white

_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             293

_exptl_absorpt_coefficient_mu    18.470
_exptl_absorpt_correction_type   ? # include if applicable
_exptl_absorpt_process_details   ? # include if applicable
_exptl_absorpt_correction_T_min  ? # include if applicable
_exptl_absorpt_correction_T_max  ? # include if applicable

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_pd_instr_location               
; ?
;
_pd_calibration_special_details  
; ?
;
_diffrn_ambient_temperature      293
_diffrn_source                   X-ray
_diffrn_source_target            ?
_diffrn_source_type              'Bruker AXS'
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_measurement_device_type  'Bruker D8 ADVANCE'
_diffrn_detector                 'position sensitive detector'
_diffrn_detector_type            LynxEye
_pd_meas_scan_method             cont
_pd_meas_special_details         
;  ?
;

_diffrn_radiation_wavelength     1.5406
_diffrn_radiation_monochromator  'Ge (111)'

_pd_meas_number_of_points        2253
_pd_meas_2theta_range_min        5.0
_pd_meas_2theta_range_max        48.84969
_pd_meas_2theta_range_inc        0.01947

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?


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

# 8. REFINEMENT DATA

_pd_proc_ls_special_details      
; A Rietveld refinement with GSAS was performed to the best solution obtained 
from the simulating annealing implemented in TOPAS. The molecular units of 
4-iodophenyl boronic acid and L-proline where represented as rigid bodies and 
were allowed to refine freely. Preferred orientation of the crystallites was 
described with a spherical harmonics function of 6th order.
;

_pd_proc_ls_profile_function     
;
CW Profile function number 3 with  19 terms
 Pseudovoigt profile coefficients as parameterized in
 P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83.
 Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994).
 J. Appl. Cryst.,27,892-900.
 #1(GU)   =   77.511 #2(GV)   =  -19.629 #3(GW)   =    4.809
 #4(GP)   =    0.000 #5(LX)   =    0.929 #6(LY)   =   18.577
 #7(S/L)  =   0.0199 #8(H/L)  =   0.0260
 #9(trns) =     9.83 #10(shft)=   1.1413
 #11(stec)=     0.00 #12(ptec)=     0.00 #13(sfec)=     0.00
 #14(L11) =    0.000 #15(L22) =    0.000 #16(L33) =    0.000
 #17(L12) =    0.000 #18(L13) =    0.000 #19(L23) =    0.000
 Peak tails are ignored  where the intensity is below 0.0010 times the peak
   Aniso. broadening axis   0.0   0.0   1.0
;
_pd_proc_ls_peak_cutoff          0.00100
_pd_proc_ls_background_function  
;   GSAS Background function number 1 with 14 terms.
 Shifted Chebyshev function of 1st kind
      1:    673.793     2:   -399.624     3:    126.654     4:   -31.8702    
      5:    21.8503     6:   -42.8202     7:    45.9706     8:   -23.0519    
      9:    14.9235    10:    11.1692    11:   -10.2477    12:    4.01710    
     13:    1.99611    14:    2.98150    
;
_pd_proc_ls_pref_orient_corr     
; ?
;

_pd_proc_ls_prof_R_factor        0.0456
_pd_proc_ls_prof_wR_factor       0.0615
_pd_proc_ls_prof_wR_expected     0.0323
_refine_ls_R_I_factor            ?
_refine_ls_R_Fsqd_factor         0.06190
_refine_ls_R_factor_all          ?

_refine_special_details          
; ?
;

_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_goodness_of_fit_all   1.95
_refine_ls_restrained_S_all      ?
_refine_ls_shift/su_max          0.02
_refine_ls_shift/su_mean         0.00

_pd_proc_2theta_range_min        5.0007
_pd_proc_2theta_range_max        48.85039
_pd_proc_2theta_range_inc        0.019
_pd_proc_wavelength              ?
_pd_block_diffractogram_id       ?
_pd_proc_info_excluded_regions   '31.6-31.8 and 45.3-45.6, impurity present'
_pd_proc_info_data_reduction     ?

_computing_data_collection       ?
_computing_cell_refinement       Topas
_computing_data_reduction        Topas
_computing_structure_solution    Topas
_computing_structure_refinement  GSAS
_computing_molecular_graphics    'Mercury 3.3.2'
_computing_publication_material  'GSAS, WINGX and Platon'


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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I Uiso 1.04654(13) 0.174(2) 0.8045(5) 1.000 0.076(3) . . . .
O1 O Uiso 0.5878(5) 0.469(2) 0.1059(17) 1.000 0.076(3) . . . .
O2 O Uiso 0.6612(4) 0.280(3) -0.1199(8) 1.000 0.076(3) . . . .
C1 C Uiso 0.7553(4) 0.317(2) 0.2479(9) 1.000 0.076(3) . . . .
C2 C Uiso 0.8338(3) 0.210(3) 0.2083(5) 1.000 0.076(3) . . . .
C3 C Uiso 0.91714(18) 0.172(3) 0.3623(4) 1.000 0.076(3) . . . .
O3 O Uiso 0.4367(9) 0.524(2) 0.8368(19) 1.000 0.076(3) . . . .
O4 O Uiso 0.5322(6) 0.398(2) 0.621(2) 1.000 0.076(3) . . . .
C4 C Uiso 0.9205(2) 0.243(2) 0.5583(5) 1.000 0.076(3) . . . .
C5 C Uiso 0.8450(3) 0.3518(19) 0.6041(10) 1.000 0.076(3) . . . .
C6 C Uiso 0.7630(4) 0.390(2) 0.4465(12) 1.000 0.076(3) . . . .
N1 N Uiso 0.4031(8) 0.463(2) 0.2748(19) 1.000 0.076(3) . . . .
B1 B Uiso 0.6633(4) 0.356(3) 0.0745(11) 1.000 0.076(3) . . . .
C7 C Uiso 0.4507(7) 0.471(2) 0.6577(19) 1.000 0.076(3) . . . .
C8 C Uiso 0.3652(7) 0.4950(17) 0.4760(18) 1.000 0.076(3) . . . .
C9 C Uiso 0.2776(5) 0.3654(14) 0.4762(13) 1.000 0.076(3) . . . .
C10 C Uiso 0.2500(5) 0.3052(12) 0.2498(11) 1.000 0.076(3) . . . .
C11 C Uiso 0.3513(6) 0.303(2) 0.1757(17) 1.000 0.076(3) . . . .
H1' H Uiso 0.5420(6) 0.488(2) 0.0040(18) 1.000 0.0800 . . . .
H2 H Uiso 0.8307(2) 0.164(3) 0.0769(4) 1.000 0.0800 . . . .
H2' H Uiso 0.6208(4) 0.321(3) -0.2199(10) 1.000 0.0800 . . . .
H3 H Uiso 0.96793(11) 0.100(3) 0.3337(6) 1.000 0.0800 . . . .
H5 H Uiso 0.8476(4) 0.3942(17) 0.7369(12) 1.000 0.0800 . . . .
H6 H Uiso 0.7111(5) 0.4589(17) 0.4745(16) 1.000 0.0800 . . . .
H1A H Uiso 0.4675(8) 0.450(3) 0.298(2) 1.000 0.0800 . . . .
H1B H Uiso 0.3876(11) 0.551(2) 0.198(2) 1.000 0.0800 . . . .
H8 H Uiso 0.3412(9) 0.6135(16) 0.474(2) 1.000 0.0800 . . . .
H9A H Uiso 0.3008(6) 0.2693(17) 0.5655(12) 1.000 0.0800 . . . .
H9B H Uiso 0.2216(6) 0.4181(15) 0.5269(16) 1.000 0.0800 . . . .
H10A H Uiso 0.2185(3) 0.1932(10) 0.2397(10) 1.000 0.0800 . . . .
H10B H Uiso 0.2035(7) 0.3839(10) 0.1678(14) 1.000 0.0800 . . . .
H11A H Uiso 0.3920(3) 0.206(2) 0.231(2) 1.000 0.0800 . . . .
H11B H Uiso 0.3482(8) 0.310(2) 0.0276(17) 1.000 0.0800 . . . .

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

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.197(7) . . yes
O1 B1 1.391(19) . . yes
O2 B1 1.407(16) . . yes
O1 H1' 0.840(15) . . no
O2 H2' 0.840(15) . . no
C1 B1 1.559(10) . . yes
C1 C2 1.410(18) . . no
C1 C6 1.413(13) . . no
C2 C3 1.405(8) . . no
O3 C7 1.295(18) . . yes
C3 C4 1.398(12) . . no
C4 C5 1.400(14) . . no
O4 C7 1.299(15) . . yes
C5 C6 1.407(10) . . no
N1 C11 1.52(2) . . yes
N1 C8 1.524(17) . . yes
C2 H2 0.931(13) . . no
C3 H3 0.93(2) . . no
C5 H5 0.930(12) . . no
C6 H6 0.928(14) . . no
N1 H1A 0.861(16) . . no
N1 H1B 0.86(2) . . no
C7 C8 1.518(16) . . no
C8 C9 1.557(14) . . no
C9 C10 1.544(11) . . no
C10 C11 1.531(11) . . no
C8 H8 0.980(18) . . no
C9 H9A 0.970(15) . . no
C9 H9B 0.971(12) . . no
C10 H10A 0.970(12) . . no
C10 H10B 0.971(12) . . no
C11 H11A 0.968(19) . . no
C11 H11B 0.970(16) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 H1' 116.6(15) . . . no
B1 O2 H2' 117(2) . . . no
C2 C1 B1 120.4(8) . . . yes
C6 C1 B1 121.1(10) . . . yes
C2 C1 C6 118.5(6) . . . no
C1 C2 C3 121.5(9) . . . no
C2 C3 C4 118.2(12) . . . no
I1 C4 C3 118.5(8) . . . yes
C3 C4 C5 122.3(6) . . . no
I1 C4 C5 119.2(5) . . . yes
C4 C5 C6 118.4(7) . . . no
C1 C6 C5 121.0(9) . . . no
O2 B1 C1 117.9(12) . . . yes
O1 B1 O2 120.5(9) . . . yes
O1 B1 C1 121.6(10) . . . yes
C8 N1 C11 107.9(10) . . . yes
C1 C2 H2 119.4(10) . . . no
C3 C2 H2 119.1(15) . . . no
C4 C3 H3 121.5(6) . . . no
C2 C3 H3 120.3(10) . . . no
C4 C5 H5 120.8(8) . . . no
C6 C5 H5 120.7(10) . . . no
C1 C6 H6 119.0(10) . . . no
C5 C6 H6 119.9(11) . . . no
C8 N1 H1B 107.3(16) . . . no
C11 N1 H1A 111(2) . . . no
C8 N1 H1A 110.5(14) . . . no
H1A N1 H1B 109(2) . . . no
C11 N1 H1B 111.2(15) . . . no
O3 C7 C8 117.7(10) . . . yes
O3 C7 O4 125.2(12) . . . yes
O4 C7 C8 117.2(11) . . . yes
N1 C8 C7 109.8(9) . . . yes
N1 C8 C9 105.5(9) . . . yes
C7 C8 C9 112.9(10) . . . no
C8 C9 C10 104.5(7) . . . no
C9 C10 C11 103.7(6) . . . no
N1 C11 C10 102.8(9) . . . yes
N1 C8 H8 107.7(13) . . . no
C7 C8 H8 109.3(13) . . . no
C9 C8 H8 111.4(11) . . . no
C8 C9 H9A 109.9(9) . . . no
C8 C9 H9B 111.3(12) . . . no
C10 C9 H9A 110.2(11) . . . no
C10 C9 H9B 113.1(9) . . . no
H9A C9 H9B 107.8(11) . . . no
C9 C10 H10A 111.6(8) . . . no
C9 C10 H10B 111.4(9) . . . no
C11 C10 H10A 111.9(9) . . . no
C11 C10 H10B 110.8(10) . . . no
H10A C10 H10B 107.6(9) . . . no
N1 C11 H11A 107.2(12) . . . no
N1 C11 H11B 108.6(15) . . . no
C10 C11 H11A 111.6(12) . . . no
C10 C11 H11B 116.0(10) . . . no
H11A C11 H11B 110.0(16) . . . no

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
C6 C1 C2 C3 2(2) . . . . no
B1 C1 C2 C3 -179.6(16) . . . . no
C2 C1 C6 C5 -3(2) . . . . no
B1 C1 C6 C5 178.6(13) . . . . no
C2 C1 B1 O1 -176.2(15) . . . . no
C2 C1 B1 O2 1(2) . . . . no
C6 C1 B1 O1 3(2) . . . . no
C6 C1 B1 O2 179.4(15) . . . . no
C1 C2 C3 C4 0(3) . . . . no
C2 C3 C4 I1 176.9(13) . . . . no
C2 C3 C4 C5 -1(2) . . . . no
I1 C4 C5 C6 -177.8(10) . . . . no
C3 C4 C5 C6 0(2) . . . . no
C4 C5 C6 C1 1.7(18) . . . . no
C8 N1 C11 C10 29.8(12) . . . . no
C11 N1 C8 C7 113.6(11) . . . . no
C11 N1 C8 C9 -8.4(12) . . . . no
O3 C7 C8 N1 167.4(14) . . . . no
O3 C7 C8 C9 -75.2(16) . . . . no
O4 C7 C8 N1 -12.9(18) . . . . no
O4 C7 C8 C9 104.5(14) . . . . no
N1 C8 C9 C10 -16.3(11) . . . . no
C7 C8 C9 C10 -136.3(9) . . . . no
C8 C9 C10 C11 34.8(10) . . . . no
C9 C10 C11 N1 -39.6(11) . . . . no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1' O3 0.840(15) 1.659(16) 2.488(16) 168.7(13) 1_554 yes
O1 H1' O4 0.840(15) 2.599(18) 3.195(17) 129.0(12) 1_554 yes
N1 H1A O1 0.861(16) 2.234(15) 2.905(14) 134.8(15) 1_555 yes
N1 H1A O4 0.861(16) 2.188(19) 2.659(17) 114.2(13) 1_555 yes
N1 H1B O2 0.86(2) 1.94(3) 2.76(3) 158.4(16) 2_655 yes
O2 H2' O4 0.840(15) 1.562(16) 2.394(16) 169.9(9) 1_554 yes
C2 H2 O2 0.931(13) 2.583(13) 2.932(9) 102.7(12) 1_555 yes
C11 H11B O3 0.970(16) 2.517(19) 3.195(18) 126.9(13) 1_554 yes

#===END
####################################################################### 
# 
# 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_jud1einm
_database_code_depnum_ccdc_archive 'CCDC 1024936'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 B2 O4, 2(C6 H6 N2 O)'
_chemical_formula_sum            'C18 H20 B2 N4 O6'
_chemical_formula_weight         410.00

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.8693(13)
_cell_length_b                   5.1027(8)
_cell_length_c                   23.951(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.465(3)
_cell_angle_gamma                90.00
_cell_volume                     961.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4568
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      28.23

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8671
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1690
_reflns_number_gt                1498
_reflns_threshold_expression     >2sigma(I)

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

_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.
 OH and NH hydrogens have been located from iterative examination of 
 difference Fourier maps following least squares refinements of the 
 previous models with the following restraints
 DFIX 0.84 0.01 for OH and DFIX 0.86 0.01 for NH
 Isotropic displacement parameters of these H atoms were set to
 Uiso=1.5Ueq(C) or  1.5Ueq (O,N).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0654P)²+0.1997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1690
_refine_ls_number_parameters     148
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.1377(2) 0.4214(3) 0.11587(6) 0.0365(4) Uani 1 1 d . . .
N1 N 0.23020(16) 0.1236(2) 0.24938(5) 0.0428(3) Uani 1 1 d . . .
N2 N 0.4259(2) 0.2519(3) 0.44939(5) 0.0464(4) Uani 1 1 d D . .
H2A H 0.460(2) 0.227(4) 0.4832(3) 0.070 Uiso 1 1 d D . .
H2B H 0.412(3) 0.4090(15) 0.4372(8) 0.070 Uiso 1 1 d D . .
O1 O 0.13321(15) 0.1780(2) 0.13858(4) 0.0471(3) Uani 1 1 d D . .
H1' H 0.164(2) 0.176(4) 0.1723(2) 0.071 Uiso 1 1 d D . .
O2 O 0.20097(15) 0.6217(2) 0.14723(4) 0.0481(3) Uani 1 1 d D . .
H2' H 0.192(3) 0.7731(16) 0.1338(8) 0.072 Uiso 1 1 d D . .
O3 O 0.45810(15) -0.17981(19) 0.43323(4) 0.0451(3) Uani 1 1 d . . .
C1 C 0.06620(18) 0.4633(3) 0.05484(5) 0.0345(3) Uani 1 1 d . . .
C2 C -0.04770(19) 0.2867(3) 0.03106(5) 0.0393(4) Uani 1 1 d . . .
H2 H -0.0812 0.1410 0.0515 0.047 Uiso 1 1 calc R . .
H3 H -0.1887 0.2000 -0.0370 0.047 Uiso 1 1 d R . .
C3 C -0.11269(19) 0.3222(3) -0.02243(6) 0.0400(4) Uani 1 1 d . . .
C7 C 0.3375(2) -0.0670(3) 0.26425(6) 0.0446(4) Uani 1 1 d . . .
H8 H 0.3714 -0.1860 0.2371 0.054 Uiso 1 1 calc R . .
C8 C 0.40055(19) -0.0969(3) 0.31773(6) 0.0399(4) Uani 1 1 d . . .
H5 H 0.4747 -0.2332 0.3263 0.048 Uiso 1 1 calc R . .
C9 C 0.35173(17) 0.0795(3) 0.35856(5) 0.0328(3) Uani 1 1 d . . .
C10 C 0.2408(2) 0.2771(3) 0.34374(6) 0.0432(4) Uani 1 1 d . . .
H7 H 0.2049 0.3987 0.3701 0.052 Uiso 1 1 calc R . .
C11 C 0.1836(2) 0.2915(3) 0.28897(6) 0.0465(4) Uani 1 1 d . . .
H6 H 0.1087 0.4254 0.2794 0.056 Uiso 1 1 calc R . .
C12 C 0.41726(18) 0.0415(3) 0.41728(5) 0.0347(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.0462(9) 0.0365(9) 0.0265(8) -0.0001(6) -0.0064(6) 0.0036(7)
N1 0.0576(8) 0.0432(7) 0.0273(6) 0.0030(5) -0.0117(5) -0.0035(6)
N2 0.0805(9) 0.0307(6) 0.0279(6) -0.0007(5) -0.0165(6) 0.0008(6)
O1 0.0771(8) 0.0385(6) 0.0255(5) 0.0038(4) -0.0174(5) -0.0026(5)
O2 0.0738(8) 0.0381(6) 0.0321(6) -0.0012(4) -0.0194(5) 0.0021(5)
O3 0.0743(7) 0.0312(6) 0.0298(5) 0.0025(4) -0.0124(5) 0.0033(5)
C1 0.0444(8) 0.0343(7) 0.0247(6) 0.0010(5) -0.0047(5) 0.0058(6)
C2 0.0532(9) 0.0367(8) 0.0278(7) 0.0070(6) -0.0052(6) -0.0041(6)
C3 0.0491(8) 0.0392(8) 0.0316(7) 0.0016(6) -0.0107(6) -0.0058(6)
C7 0.0636(10) 0.0426(8) 0.0275(7) -0.0042(6) -0.0053(6) 0.0040(7)
C8 0.0533(9) 0.0359(7) 0.0304(7) -0.0005(6) -0.0068(6) 0.0057(6)
C9 0.0422(7) 0.0307(7) 0.0255(7) 0.0025(5) -0.0046(5) -0.0050(5)
C10 0.0556(9) 0.0426(8) 0.0312(7) -0.0035(6) -0.0045(6) 0.0099(7)
C11 0.0559(9) 0.0451(9) 0.0382(8) 0.0042(6) -0.0138(7) 0.0103(7)
C12 0.0478(8) 0.0309(7) 0.0254(7) 0.0027(5) -0.0057(5) -0.0019(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.3567(19) . ?
B1 O2 1.3601(19) . ?
B1 C1 1.5766(18) . ?
N1 C11 1.332(2) . ?
N1 C7 1.3344(19) . ?
N2 C12 1.3222(18) . ?
O3 C12 1.2339(16) . ?
C1 C2 1.390(2) . ?
C1 C3 1.393(2) 3_565 ?
C2 C3 1.3874(19) . ?
C3 C1 1.393(2) 3_565 ?
C7 C8 1.378(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.378(2) . ?
C9 C12 1.5066(17) . ?
C10 C11 1.385(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 O2 118.50(12) . . ?
O1 B1 C1 119.04(12) . . ?
O2 B1 C1 122.45(12) . . ?
C11 N1 C7 117.15(12) . . ?
C2 C1 C3 116.91(12) . 3_565 ?
C2 C1 B1 121.08(12) . . ?
C3 C1 B1 122.00(12) 3_565 . ?
C3 C2 C1 121.70(13) . . ?
C2 C3 C1 121.39(13) . 3_565 ?
N1 C7 C8 123.42(13) . . ?
C7 C8 C9 118.96(13) . . ?
C10 C9 C8 118.18(12) . . ?
C10 C9 C12 123.08(12) . . ?
C8 C9 C12 118.71(12) . . ?
C9 C10 C11 118.86(13) . . ?
N1 C11 C10 123.43(14) . . ?
O3 C12 N2 123.42(11) . . ?
O3 C12 C9 119.56(11) . . ?
N2 C12 C9 117.02(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
O1 B1 C1 C2 21.1(2) . . . . ?
O2 B1 C1 C2 -157.64(15) . . . . ?
O1 B1 C1 C3 -159.34(15) . . . 3_565 ?
O2 B1 C1 C3 22.0(2) . . . 3_565 ?
C3 C1 C2 C3 -0.2(2) 3_565 . . . ?
B1 C1 C2 C3 179.46(14) . . . . ?
C1 C2 C3 C1 0.2(3) . . . 3_565 ?
C11 N1 C7 C8 0.0(2) . . . . ?
N1 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C7 C8 C9 C12 178.32(13) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C12 C9 C10 C11 -178.09(14) . . . . ?
C7 N1 C11 C10 0.1(2) . . . . ?
C9 C10 C11 N1 0.0(3) . . . . ?
C10 C9 C12 O3 151.86(15) . . . . ?
C8 C9 C12 O3 -26.0(2) . . . . ?
C10 C9 C12 N2 -27.4(2) . . . . ?
C8 C9 C12 N2 154.71(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_?
_database_code_depnum_ccdc_archive 'CCDC 1024937'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;

loop_
_audit_conform_dict_name
_audit_conform_dict_version
_audit_conform_dict_location
cif_core.dic . ftp://ftp.iucr.org/pub/cif_core.dic
cif_pd.dic . ftp://ftp.iucr.org/pub/cif_pd.dic

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            
'cocrystal (II) of 4-iodophenylboronic acid with L-proline (1:1)'
_chemical_formula_moiety         'C6 H6 B I O2, C5 H9 N O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C11 H15 B I N O4'
_chemical_formula_weight         362.95
_chemical_melting_point          ?
_chemical_compound_source        'see text'
_chemical_properties_physical    ?
_exptl_crystal_recrystallization_method 'Solvent assisted grinding: water'

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'
I I -0.3257 6.8362 ' 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'

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   26.560(11)
_cell_length_b                   7.8526(34)
_cell_length_c                   6.5921(28)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1374.9(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'Not Measured'
_cell_special_details            
; ?
;

_pd_spec_size_axial              10 # perpendicular to 
# equatorial plane
_pd_spec_size_equat              10 # parallel to 
# scattering vector 
# in transmission
_pd_spec_size_thick              ? # perpendicular to 
# scattering vector 
# in transmission

_pd_spec_mounting                'Packed between thin slides of cellophane'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   flat_sheet
_pd_char_particle_morphology     'white powder (visual)'
_pd_char_colour                  white

_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             293

_exptl_absorpt_coefficient_mu    18.366
_exptl_absorpt_correction_type   ? # include if applicable
_exptl_absorpt_process_details   ? # include if applicable
_exptl_absorpt_correction_T_min  ? # include if applicable
_exptl_absorpt_correction_T_max  ? # include if applicable

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_pd_instr_location               
; ?
;
_pd_calibration_special_details  
; ?
;
_diffrn_ambient_temperature      293
_diffrn_source                   X-ray
_diffrn_source_target            ?
_diffrn_source_type              'Bruker AXS'
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_measurement_device_type  'Bruker D8 ADVANCE'
_diffrn_detector                 'position sensitive detector'
_diffrn_detector_type            LynxEye
_pd_meas_scan_method             cont
_pd_meas_special_details         
;  ?
;

_diffrn_radiation_wavelength     1.5406
_diffrn_radiation_monochromator  'Ge (111)'

_pd_meas_number_of_points        2253
_pd_meas_2theta_range_min        5.0
_pd_meas_2theta_range_max        48.84969
_pd_meas_2theta_range_inc        0.019

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?


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

# 8. REFINEMENT DATA

_pd_proc_ls_special_details      
; A Rietveld refinement with GSAS was performed to the best solution obtained 
from the simulating annealing implemented in TOPAS. The molecular units of 
4-iodophenyl boronic acid and L-proline where represented as rigid bodies and 
were allowed to refine freely. Preferred orientation of the crystallites was 
described with a spherical harmonics function of 8th order.
;

_pd_proc_ls_profile_function     
;
CW Profile function number 3 with  19 terms
 Pseudovoigt profile coefficients as parameterized in
 P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83.
 Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994).
 J. Appl. Cryst.,27,892-900.
 #1(GU)   =    0.000 #2(GV)   =   10.244 #3(GW)   =    3.414
 #4(GP)   =    0.000 #5(LX)   =    0.000 #6(LY)   =   27.576
 #7(S/L)  =   0.0203 #8(H/L)  =   0.0200
 #9(trns) =    -2.72 #10(shft)=   2.1504
 #11(stec)=     0.00 #12(ptec)=     0.00 #13(sfec)=     0.00
 #14(L11) =    0.000 #15(L22) =    0.000 #16(L33) =    0.000
 #17(L12) =    0.000 #18(L13) =    0.000 #19(L23) =    0.000
 Peak tails are ignored  where the intensity is below 0.0010 times the peak
   Aniso. broadening axis   0.0   0.0   1.0
;
_pd_proc_ls_peak_cutoff          0.00100
_pd_proc_ls_background_function  
;   GSAS Background function number 1 with 14 terms.
 Shifted Chebyshev function of 1st kind
      1:    692.740     2:   -403.135     3:    102.680     4:   -18.2640    
      5:    23.7502     6:   -59.3174     7:    45.8724     8:   -22.1376    
      9:    15.5991    10:    13.4833    11:   -6.03485    12:   -2.43802    
     13:   -3.67884    14:    10.3540 
;
_pd_proc_ls_pref_orient_corr     
; ?
;

_pd_proc_ls_prof_R_factor        0.0491
_pd_proc_ls_prof_wR_factor       0.0662
_pd_proc_ls_prof_wR_expected     0.0320
_refine_ls_R_I_factor            ?
_refine_ls_R_Fsqd_factor         0.06323
_refine_ls_R_factor_all          ?

_refine_special_details          
; ?
;

_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     47
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_goodness_of_fit_all   2.09
_refine_ls_restrained_S_all      ?
_refine_ls_shift/su_max          0.19
_refine_ls_shift/su_mean         0.02

_pd_proc_2theta_range_min        5.0007
_pd_proc_2theta_range_max        48.85039
_pd_proc_2theta_range_inc        0.019
_pd_proc_wavelength              ?
_pd_block_diffractogram_id       ?
_pd_proc_info_excluded_regions   '31.6-31.8 and 45.3-45.6 impurity present'
_pd_proc_info_data_reduction     ?

_computing_data_collection       ?
_computing_cell_refinement       Topas
_computing_data_reduction        Topas
_computing_structure_solution    Topas
_computing_structure_refinement  GSAS
_computing_molecular_graphics    'Mercury 3.3.2'
_computing_publication_material  'GSAS, WINGX and Platon'


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


# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I Uiso 0.77722(5) 0.7472(5) 0.8427(4) 1.000 0.053(3) . . . .
O1 O Uiso 0.5442(2) 1.0368(7) 0.335(2) 1.000 0.053(3) . . . .
O2 O Uiso 0.5805(2) 0.8585(16) 0.0703(13) 1.000 0.053(3) . . . .
C1 C Uiso 0.63010(15) 0.8936(8) 0.4007(13) 1.000 0.053(3) . . . .
C2 C Uiso 0.67190(14) 0.8040(12) 0.3214(7) 1.000 0.053(3) . . . .
C3 C Uiso 0.71407(10) 0.7661(10) 0.4417(5) 1.000 0.053(3) . . . .
O3 O Uiso 0.5301(2) 0.5726(19) 0.404(2) 1.000 0.053(3) . . . .
O4 O Uiso 0.48399(15) 0.4599(14) 0.6688(17) 1.000 0.053(3) . . . .
C4 C Uiso 0.71384(7) 0.8176(5) 0.6449(7) 1.000 0.053(3) . . . .
C5 C Uiso 0.67392(8) 0.9104(5) 0.7286(12) 1.000 0.053(3) . . . .
C6 C Uiso 0.63225(11) 0.9476(4) 0.6048(15) 1.000 0.053(3) . . . .
N1 N Uiso 0.5531(2) 0.525(2) 0.9531(19) 1.000 0.053(3) . . . .
B1 B Uiso 0.58271(19) 0.9301(11) 0.2661(16) 1.000 0.053(3) . . . .
C7 C Uiso 0.52437(16) 0.5282(13) 0.5919(19) 1.000 0.053(3) . . . .
C8 C Uiso 0.56875(16) 0.5557(15) 0.734(2) 1.000 0.053(3) . . . .
C9 C Uiso 0.61321(15) 0.4312(15) 0.692(2) 1.000 0.053(3) . . . .
C10 C Uiso 0.6303(3) 0.3720(19) 0.905(3) 1.000 0.053(3) . . . .
C11 C Uiso 0.5818(3) 0.370(3) 1.031(2) 1.000 0.053(3) . . . .
H1' H Uiso 0.5208(2) 1.0561(9) 0.253(2) 1.000 0.0650 . . . .
H2 H Uiso 0.67170(17) 0.7691(16) 0.1866(6) 1.000 0.0650 . . . .
H2' H Uiso 0.5595(3) 0.9010(18) -0.0104(16) 1.000 0.0650 . . . .
H3 H Uiso 0.74097(10) 0.7060(12) 0.3865(4) 1.000 0.0650 . . . .
H5 H Uiso 0.67417(7) 0.9446(7) 0.8637(13) 1.000 0.0650 . . . .
H6 H Uiso 0.60495(12) 1.0063(4) 0.6588(18) 1.000 0.0650 . . . .
H1A H Uiso 0.5211(2) 0.510(3) 0.9598(19) 1.000 0.0650 . . . .
H1B H Uiso 0.5615(2) 0.613(3) 1.022(2) 1.000 0.0650 . . . .
H8 H Uiso 0.5798(2) 0.6744(14) 0.723(3) 1.000 0.0650 . . . .
H9A H Uiso 0.60187(14) 0.3358(16) 0.611(3) 1.000 0.0650 . . . .
H9B H Uiso 0.63976(14) 0.4900(18) 0.619(2) 1.000 0.0650 . . . .
H10A H Uiso 0.6461(3) 0.2606(19) 0.902(3) 1.000 0.0650 . . . .
H10B H Uiso 0.6545(3) 0.451(2) 0.963(2) 1.000 0.0650 . . . .
H11A H Uiso 0.5615(4) 0.270(3) 1.004(3) 1.000 0.0650 . . . .
H11B H Uiso 0.5866(4) 0.382(4) 1.176(2) 1.000 0.0650 . . . .

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

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.200(4) . . yes
O1 B1 1.398(10) . . yes
O2 B1 1.409(14) . . yes
O1 H1' 0.838(13) . . no
O2 H2' 0.840(13) . . no
C1 B1 1.566(9) . . yes
C1 C2 1.415(8) . . no
C1 C6 1.412(13) . . no
C2 C3 1.404(6) . . no
O3 C7 1.296(18) . . yes
C3 C4 1.399(6) . . no
C4 C5 1.400(5) . . no
O4 C7 1.302(10) . . yes
C5 C6 1.406(8) . . no
N1 C11 1.53(2) . . yes
N1 C8 1.522(18) . . yes
C2 H2 0.930(7) . . no
C3 H3 0.930(7) . . no
C5 H5 0.930(11) . . no
C6 H6 0.930(7) . . no
N1 H1A 0.859(8) . . no
N1 H1B 0.86(2) . . no
C7 C8 1.521(12) . . no
C8 C9 1.558(12) . . no
C9 C10 1.55(2) . . no
C10 C11 1.533(16) . . no
C8 H8 0.980(16) . . no
C9 H9A 0.968(19) . . no
C9 H9B 0.971(13) . . no
C10 H10A 0.97(2) . . no
C10 H10B 0.972(18) . . no
C11 H11A 0.97(3) . . no
C11 H11B 0.969(19) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 H1' 116.2(14) . . . no
B1 O2 H2' 116.7(13) . . . no
C2 C1 B1 120.8(7) . . . yes
C6 C1 B1 121.2(5) . . . yes
C2 C1 C6 118.0(5) . . . no
C1 C2 C3 121.5(5) . . . no
C2 C3 C4 118.4(4) . . . no
I1 C4 C3 119.4(3) . . . yes
C3 C4 C5 122.1(4) . . . no
I1 C4 C5 118.5(4) . . . yes
C4 C5 C6 118.4(6) . . . no
C1 C6 C5 121.5(5) . . . no
O2 B1 C1 118.6(6) . . . yes
O1 B1 O2 120.4(8) . . . yes
O1 B1 C1 120.9(9) . . . yes
C8 N1 C11 108.0(9) . . . yes
C1 C2 H2 119.7(7) . . . no
C3 C2 H2 118.8(7) . . . no
C4 C3 H3 121.6(3) . . . no
C2 C3 H3 119.9(4) . . . no
C4 C5 H5 121.5(5) . . . no
C6 C5 H5 120.1(5) . . . no
C1 C6 H6 118.8(9) . . . no
C5 C6 H6 119.6(11) . . . no
C8 N1 H1B 107.7(16) . . . no
C11 N1 H1A 112(2) . . . no
C8 N1 H1A 109.9(13) . . . no
H1A N1 H1B 109.9(19) . . . no
C11 N1 H1B 109.6(15) . . . no
O3 C7 C8 117.4(7) . . . yes
O3 C7 O4 125.4(9) . . . yes
O4 C7 C8 117.2(11) . . . yes
N1 C8 C7 110.5(6) . . . yes
N1 C8 C9 106.0(9) . . . yes
C7 C8 C9 112.9(10) . . . no
C8 C9 C10 104.5(10) . . . no
C9 C10 C11 104.4(8) . . . no
N1 C11 C10 103.3(13) . . . yes
N1 C8 H8 107.6(16) . . . no
C7 C8 H8 108.8(13) . . . no
C9 C8 H8 110.9(7) . . . no
C8 C9 H9A 110.4(7) . . . no
C8 C9 H9B 109.9(12) . . . no
C10 C9 H9A 111.1(15) . . . no
C10 C9 H9B 112.3(9) . . . no
H9A C9 H9B 108.7(17) . . . no
C9 C10 H10A 112(2) . . . no
C9 C10 H10B 111.1(16) . . . no
C11 C10 H10A 111.4(17) . . . no
C11 C10 H10B 110.4(17) . . . no
H10A C10 H10B 107.3(14) . . . no
N1 C11 H11A 107.9(14) . . . no
N1 C11 H11B 109(2) . . . no
C10 C11 H11A 112.1(18) . . . no
C10 C11 H11B 115.0(12) . . . no
H11A C11 H11B 110(3) . . . no

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
C6 C1 C2 C3 1.3(11) . . . . no
B1 C1 C2 C3 -178.2(7) . . . . no
C2 C1 C6 C5 -1.6(8) . . . . no
B1 C1 C6 C5 177.8(5) . . . . no
C2 C1 B1 O1 -171.8(7) . . . . no
C2 C1 B1 O2 5.8(11) . . . . no
C6 C1 B1 O1 8.8(10) . . . . no
C6 C1 B1 O2 -173.7(7) . . . . no
C1 C2 C3 C4 0.7(11) . . . . no
C2 C3 C4 I1 176.4(5) . . . . no
C2 C3 C4 C5 -2.4(9) . . . . no
I1 C4 C5 C6 -176.7(3) . . . . no
C3 C4 C5 C6 2.0(6) . . . . no
C4 C5 C6 C1 0.0(6) . . . . no
C8 N1 C11 C10 28.1(14) . . . . no
C11 N1 C8 C7 114.8(10) . . . . no
C11 N1 C8 C9 -7.9(12) . . . . no
O3 C7 C8 N1 170.6(12) . . . . no
O3 C7 C8 C9 -70.8(14) . . . . no
O4 C7 C8 N1 -10.3(14) . . . . no
O4 C7 C8 C9 108.3(11) . . . . no
N1 C8 C9 C10 -15.3(10) . . . . no
C7 C8 C9 C10 -136.4(10) . . . . no
C8 C9 C10 C11 32.8(14) . . . . no
C9 C10 C11 N1 -37.4(15) . . . . no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1' O3 0.838(13) 1.708(13) 2.541(13) 173.0(10) 4_655 yes
N1 H1A O4 0.859(8) 2.192(16) 2.673(13) 115.1(13) 1_555 yes
N1 H1A O1 0.859(8) 2.210(13) 2.939(11) 142.7(15) 4_646 yes
N1 H1B O2 0.86(2) 2.02(3) 2.826(19) 156.9(17) 1_556 yes
O2 H2' O4 0.840(13) 1.624(13) 2.460(12) 173.0(16) 4_655 yes
C11 H11B O3 0.969(19) 2.60(2) 3.24(2) 123.4(18) 1_556 yes

#===END
####################################################################### 
# 
# 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_po1funm
_database_code_depnum_ccdc_archive 'CCDC 1024938'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 B I O2, C6 H6 N2 O'
_chemical_formula_sum            'C12 H12 B I N2 O3'
_chemical_formula_weight         369.95

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1113(7)
_cell_length_b                   11.2936(16)
_cell_length_c                   12.0927(17)
_cell_angle_alpha                76.589(2)
_cell_angle_beta                 84.831(2)
_cell_angle_gamma                78.494(2)
_cell_volume                     664.67(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2671
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      26.82

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    2.413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5736
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2321
_reflns_number_gt                2124
_reflns_threshold_expression     >2sigma(I)

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

_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.
 OH and NH hydrogens have been located from iterative examination of 
 difference Fourier maps following least squares refinements of the 
 previous models with the following restraints
 DFIX 0.84 0.01 for OH and DFIX 0.86 0.01 for NH
 Isotropic displacement parameters of these H atoms were set to
 Uiso=1.5Ueq(C) or  1.5Ueq (O,N).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0379P)²+0.1488P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2321
_refine_ls_number_parameters     184
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.49801(6) 0.47603(2) -0.34617(2) 0.02577(12) Uani 1 1 d . . .
B1 B 0.6776(8) 0.2476(4) 0.1889(4) 0.0154(9) Uani 1 1 d . . .
N1 N 0.9047(6) 0.1935(3) 0.4637(3) 0.0174(7) Uani 1 1 d . . .
N2 N 0.7690(6) 0.0215(3) 0.8856(3) 0.0173(7) Uani 1 1 d D . .
H2A H 0.778(8) 0.000(4) 0.9584(5) 0.026 Uiso 1 1 d D . .
H2B H 0.614(4) 0.048(4) 0.858(3) 0.026 Uiso 1 1 d D . .
O1 O 0.9140(5) 0.2455(3) 0.2320(2) 0.0193(6) Uani 1 1 d D . .
H1' H 0.913(9) 0.222(4) 0.3032(4) 0.029 Uiso 1 1 d D . .
O2 O 0.4759(5) 0.2071(3) 0.2605(2) 0.0184(6) Uani 1 1 d D . .
H2' H 0.327(4) 0.216(4) 0.233(4) 0.028 Uiso 1 1 d D . .
O3 O 1.1933(5) 0.0533(3) 0.8641(2) 0.0194(6) Uani 1 1 d . . .
C1 C 0.6421(7) 0.2979(3) 0.0571(3) 0.0155(8) Uani 1 1 d . . .
C2 C 0.7951(8) 0.3827(4) -0.0058(3) 0.0205(9) Uani 1 1 d . . .
H2 H 0.9236 0.4060 0.0303 0.025 Uiso 1 1 calc R . .
C3 C 0.7593(8) 0.4330(4) -0.1211(3) 0.0203(9) Uani 1 1 d . . .
H3 H 0.8618 0.4896 -0.1616 0.024 Uiso 1 1 calc R . .
C4 C 0.5700(8) 0.3978(3) -0.1742(3) 0.0177(8) Uani 1 1 d . . .
C5 C 0.4188(8) 0.3117(4) -0.1148(3) 0.0207(9) Uani 1 1 d . . .
H5 H 0.2955 0.2862 -0.1519 0.025 Uiso 1 1 calc R . .
C6 C 0.4539(8) 0.2645(4) -0.0002(3) 0.0192(9) Uani 1 1 d . . .
H6 H 0.3487 0.2089 0.0399 0.023 Uiso 1 1 calc R . .
C7 C 1.0718(8) 0.2301(4) 0.5223(3) 0.0201(9) Uani 1 1 d . . .
H7 H 1.1754 0.2869 0.4831 0.024 Uiso 1 1 calc R . .
C8 C 1.0976(7) 0.1880(4) 0.6372(3) 0.0171(8) Uani 1 1 d . . .
H8 H 1.2185 0.2151 0.6742 0.021 Uiso 1 1 calc R . .
C9 C 0.9425(7) 0.1046(3) 0.6983(3) 0.0142(8) Uani 1 1 d . . .
C10 C 0.7665(7) 0.0672(4) 0.6386(3) 0.0177(8) Uani 1 1 d . . .
H10 H 0.6586 0.0115 0.6760 0.021 Uiso 1 1 calc R . .
C11 C 0.7541(7) 0.1139(4) 0.5224(3) 0.0189(9) Uani 1 1 d . . .
H11 H 0.6347 0.0886 0.4832 0.023 Uiso 1 1 calc R . .
C12 C 0.9777(7) 0.0576(3) 0.8236(3) 0.0150(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0403(2) 0.02403(18) 0.01053(16) 0.00016(11) -0.00573(12) -0.00275(12)
B1 0.018(2) 0.012(2) 0.017(2) -0.0039(18) -0.0011(18) -0.0015(17)
N1 0.0146(16) 0.0209(18) 0.0139(18) -0.0008(14) 0.0012(13) -0.0011(14)
N2 0.0127(16) 0.0269(19) 0.0104(17) 0.0019(15) -0.0037(14) -0.0052(14)
O1 0.0157(14) 0.0311(16) 0.0104(14) -0.0015(13) -0.0010(11) -0.0057(12)
O2 0.0136(13) 0.0270(15) 0.0126(15) 0.0019(12) -0.0022(11) -0.0060(12)
O3 0.0126(13) 0.0329(16) 0.0127(14) -0.0014(12) -0.0017(11) -0.0076(11)
C1 0.0122(18) 0.017(2) 0.016(2) -0.0015(16) -0.0006(15) -0.0014(15)
C2 0.017(2) 0.027(2) 0.017(2) -0.0011(18) -0.0064(17) -0.0068(17)
C3 0.022(2) 0.023(2) 0.013(2) 0.0056(17) -0.0012(17) -0.0101(17)
C4 0.025(2) 0.016(2) 0.010(2) -0.0020(16) -0.0016(16) 0.0005(16)
C5 0.025(2) 0.023(2) 0.016(2) -0.0038(18) -0.0060(17) -0.0078(17)
C6 0.025(2) 0.019(2) 0.014(2) -0.0021(17) 0.0037(17) -0.0062(17)
C7 0.020(2) 0.023(2) 0.016(2) 0.0027(17) -0.0004(17) -0.0090(17)
C8 0.0148(19) 0.024(2) 0.014(2) -0.0027(17) -0.0038(16) -0.0073(16)
C9 0.0121(18) 0.018(2) 0.010(2) -0.0006(16) -0.0014(15) -0.0009(15)
C10 0.0131(19) 0.020(2) 0.019(2) -0.0022(17) -0.0009(16) -0.0047(15)
C11 0.016(2) 0.026(2) 0.015(2) -0.0054(18) -0.0024(16) -0.0046(17)
C12 0.015(2) 0.0150(19) 0.014(2) -0.0050(16) -0.0013(16) 0.0005(15)

_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
I1 C4 2.096(4) . ?
B1 O1 1.352(5) . ?
B1 O2 1.366(5) . ?
B1 C1 1.577(6) . ?
N1 C11 1.336(5) . ?
N1 C7 1.337(5) . ?
N2 C12 1.324(5) . ?
O3 C12 1.233(4) . ?
C1 C6 1.391(5) . ?
C1 C2 1.401(6) . ?
C2 C3 1.392(6) . ?
C3 C4 1.375(5) . ?
C4 C5 1.391(6) . ?
C5 C6 1.378(6) . ?
C7 C8 1.370(5) . ?
C8 C9 1.389(5) . ?
C9 C10 1.385(5) . ?
C9 C12 1.500(5) . ?
C10 C11 1.384(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 O2 119.3(4) . . ?
O1 B1 C1 118.9(4) . . ?
O2 B1 C1 121.8(3) . . ?
C11 N1 C7 117.2(3) . . ?
C6 C1 C2 117.5(4) . . ?
C6 C1 B1 122.2(4) . . ?
C2 C1 B1 120.3(3) . . ?
C3 C2 C1 121.5(4) . . ?
C4 C3 C2 119.0(4) . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 I1 120.4(3) . . ?
C5 C4 I1 118.7(3) . . ?
C6 C5 C4 119.3(4) . . ?
C5 C6 C1 121.8(4) . . ?
N1 C7 C8 123.1(4) . . ?
C7 C8 C9 119.8(3) . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 C12 123.5(4) . . ?
C8 C9 C12 118.9(3) . . ?
C11 C10 C9 118.8(4) . . ?
N1 C11 C10 123.5(3) . . ?
O3 C12 N2 123.2(4) . . ?
O3 C12 C9 120.1(3) . . ?
N2 C12 C9 116.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 B1 C1 C6 156.7(4) . . . . ?
O2 B1 C1 C6 -23.8(6) . . . . ?
O1 B1 C1 C2 -25.9(5) . . . . ?
O2 B1 C1 C2 153.7(4) . . . . ?
C6 C1 C2 C3 0.6(6) . . . . ?
B1 C1 C2 C3 -177.0(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C2 C3 C4 I1 177.6(3) . . . . ?
C3 C4 C5 C6 2.2(6) . . . . ?
I1 C4 C5 C6 -176.5(3) . . . . ?
C4 C5 C6 C1 -2.0(6) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
B1 C1 C6 C5 178.1(3) . . . . ?
C11 N1 C7 C8 1.4(6) . . . . ?
N1 C7 C8 C9 -1.0(6) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C7 C8 C9 C12 178.7(3) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C12 C9 C10 C11 -178.4(3) . . . . ?
C7 N1 C11 C10 -1.1(6) . . . . ?
C9 C10 C11 N1 0.4(6) . . . . ?
C10 C9 C12 O3 151.8(4) . . . . ?
C8 C9 C12 O3 -26.6(5) . . . . ?
C10 C9 C12 N2 -27.8(5) . . . . ?
C8 C9 C12 N2 153.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.002
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.139
####################################################################### 
# 
# 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_poli3x
_database_code_depnum_ccdc_archive 'CCDC 1024939'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 B I O2, C6 H6 N2 O'
_chemical_formula_sum            'C12 H12 B I N2 O3'
_chemical_formula_weight         369.95

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

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

_cell_length_a                   34.686(8)
_cell_length_b                   4.0087(9)
_cell_length_c                   10.092(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1403.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4976
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.79

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8977
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2439
_reflns_number_gt                2230
_reflns_threshold_expression     >2sigma(I)

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

_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.
 Due to bad crystal quality, SIMU, DELU and ISOR instructions have been
 used for the refinement of the heavy atoms (simu 0.01 I1 > C12,
 delu 0.005 I1 > C12, ISOR 0.005 I1 > C12)
 OH and NH hydrogens have been located from iterative examination of 
 difference Fourier maps following least squares refinements of the 
 previous models with the following restraints
 DFIX 0.84 0.01 for OH and DFIX 0.86 0.01 for NH
 Isotropic displacement parameters of these H atoms were set to
 Uiso=1.5Ueq(C) or  1.5Ueq (O,N).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0584P)²+1.2096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_number_reflns         2439
_refine_ls_number_parameters     184
_refine_ls_number_restraints     270
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.458910(12) 0.09400(10) 0.8599(5) 0.01825(17) Uani 1 1 d U . .
B1 B 0.6394(2) 0.5224(19) 0.8731(14) 0.0125(16) Uani 1 1 d U . .
N1 N 0.6566(2) 0.2683(19) 0.5082(9) 0.0163(14) Uani 1 1 d U . .
N2 N 0.7584(2) -0.272(2) 0.2599(3) 0.0120(16) Uani 1 1 d DU . .
H2A H 0.7829(5) -0.31(2) 0.259(9) 0.018 Uiso 1 1 d D . .
H2B H 0.748(2) -0.22(2) 0.184(4) 0.018 Uiso 1 1 d D . .
O1 O 0.65537(18) 0.6537(16) 0.9854(8) 0.0184(14) Uani 1 1 d DU . .
H1' H 0.6789(7) 0.61(2) 0.977(10) 0.028 Uiso 1 1 d D . .
O2 O 0.6636(2) 0.4946(17) 0.7628(7) 0.0162(13) Uani 1 1 d DU . .
H2' H 0.652(2) 0.40(2) 0.701(6) 0.024 Uiso 1 1 d D . .
O3 O 0.76486(18) -0.1679(15) 0.4791(7) 0.0122(13) Uani 1 1 d U . .
C1 C 0.59578(18) 0.4257(16) 0.8694(15) 0.0121(13) Uani 1 1 d U . .
C2 C 0.5789(2) 0.261(2) 0.7579(9) 0.0159(15) Uani 1 1 d U . .
H2 H 0.5947 0.2078 0.6838 0.019 Uiso 1 1 calc R . .
C3 C 0.5402(2) 0.176(2) 0.7550(10) 0.0165(15) Uani 1 1 d U . .
H3 H 0.5294 0.0717 0.6790 0.020 Uiso 1 1 calc R . .
C4 C 0.51718(17) 0.2462(17) 0.8672(14) 0.0137(13) Uani 1 1 d U . .
C5 C 0.5322(2) 0.405(2) 0.9746(10) 0.0159(15) Uani 1 1 d U . .
H5 H 0.5162 0.4567 1.0483 0.019 Uiso 1 1 calc R . .
C6 C 0.5715(2) 0.493(2) 0.9759(10) 0.0137(15) Uani 1 1 d U . .
H6 H 0.5817 0.6008 1.0519 0.016 Uiso 1 1 calc R . .
C7 C 0.6914(3) 0.131(2) 0.4954(10) 0.0118(16) Uani 1 1 d U . .
H7 H 0.7071 0.1170 0.5722 0.014 Uiso 1 1 calc R . .
C8 C 0.70633(19) 0.0043(16) 0.3757(11) 0.0124(14) Uani 1 1 d U . .
C9 C 0.6845(3) 0.058(2) 0.2625(10) 0.0128(16) Uani 1 1 d U . .
H9 H 0.6939 -0.0094 0.1782 0.015 Uiso 1 1 calc R . .
C10 C 0.6477(3) 0.217(2) 0.2743(10) 0.0158(16) Uani 1 1 d U . .
H10 H 0.6323 0.2553 0.1981 0.019 Uiso 1 1 calc R . .
C11 C 0.6353(2) 0.311(2) 0.3970(8) 0.0106(16) Uani 1 1 d U . .
H11 H 0.6105 0.4105 0.4049 0.013 Uiso 1 1 calc R . .
C12 C 0.7460(2) -0.1474(17) 0.3764(11) 0.0109(14) Uani 1 1 d U . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0102(2) 0.0150(2) 0.0296(3) 0.0036(4) 0.0003(5) -0.00162(19)
B1 0.015(2) 0.011(3) 0.011(3) -0.001(3) 0.005(3) 0.000(2)
N1 0.013(3) 0.022(3) 0.013(3) -0.005(3) -0.006(2) -0.001(2)
N2 0.013(3) 0.014(3) 0.009(3) -0.001(3) 0.000(3) -0.008(3)
O1 0.013(3) 0.028(3) 0.015(3) -0.007(2) 0.004(2) -0.002(2)
O2 0.010(3) 0.027(3) 0.012(3) -0.004(2) -0.001(2) -0.004(3)
O3 0.011(3) 0.017(3) 0.008(2) 0.001(2) -0.001(2) 0.003(2)
C1 0.012(2) 0.013(2) 0.011(3) 0.000(3) 0.000(2) 0.003(2)
C2 0.014(3) 0.021(3) 0.012(3) -0.003(3) 0.005(2) -0.001(3)
C3 0.015(3) 0.019(3) 0.016(3) 0.000(3) -0.002(2) -0.003(3)
C4 0.010(2) 0.013(2) 0.018(3) 0.001(3) 0.002(3) -0.001(2)
C5 0.012(2) 0.017(3) 0.018(3) -0.003(3) 0.004(2) 0.001(3)
C6 0.011(2) 0.017(3) 0.013(3) -0.002(3) 0.002(2) 0.000(3)
C7 0.011(3) 0.014(3) 0.011(3) -0.001(3) -0.004(2) -0.004(2)
C8 0.011(2) 0.017(2) 0.009(3) 0.003(3) -0.002(2) -0.003(2)
C9 0.012(3) 0.016(3) 0.010(3) 0.005(3) 0.002(2) -0.002(3)
C10 0.013(3) 0.023(3) 0.012(3) 0.001(3) 0.001(3) 0.001(3)
C11 0.008(3) 0.012(3) 0.012(3) 0.002(2) -0.001(2) 0.001(2)
C12 0.013(2) 0.015(3) 0.005(3) 0.004(3) 0.002(2) -0.002(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.112(6) . ?
B1 O1 1.366(14) . ?
B1 O2 1.398(14) . ?
B1 C1 1.564(10) . ?
N1 C7 1.331(12) . ?
N1 C11 1.356(10) . ?
N2 C12 1.349(12) . ?
O3 C12 1.229(11) . ?
C1 C6 1.392(14) . ?
C1 C2 1.430(14) . ?
C2 C3 1.385(12) . ?
C3 C4 1.415(15) . ?
C4 C5 1.360(14) . ?
C5 C6 1.408(11) . ?
C7 C8 1.410(13) . ?
C8 C9 1.387(13) . ?
C8 C12 1.504(9) . ?
C9 C10 1.431(13) . ?
C10 C11 1.365(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 O2 116.7(7) . . ?
O1 B1 C1 120.5(10) . . ?
O2 B1 C1 122.8(10) . . ?
C7 N1 C11 117.8(8) . . ?
C6 C1 C2 116.7(6) . . ?
C6 C1 B1 121.3(10) . . ?
C2 C1 B1 122.0(10) . . ?
C3 C2 C1 121.8(8) . . ?
C2 C3 C4 118.8(8) . . ?
C5 C4 C3 121.0(7) . . ?
C5 C4 I1 121.9(8) . . ?
C3 C4 I1 117.0(7) . . ?
C4 C5 C6 119.7(8) . . ?
C1 C6 C5 122.0(8) . . ?
N1 C7 C8 124.4(8) . . ?
C9 C8 C7 116.7(7) . . ?
C9 C8 C12 124.4(9) . . ?
C7 C8 C12 118.6(8) . . ?
C8 C9 C10 119.1(8) . . ?
C11 C10 C9 118.7(8) . . ?
N1 C11 C10 122.9(8) . . ?
O3 C12 N2 122.7(7) . . ?
O3 C12 C8 121.2(8) . . ?
N2 C12 C8 116.0(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
O1 B1 C1 C6 4.7(12) . . . . ?
O2 B1 C1 C6 -172.4(8) . . . . ?
O1 B1 C1 C2 -174.3(8) . . . . ?
O2 B1 C1 C2 8.6(12) . . . . ?
C6 C1 C2 C3 0.9(13) . . . . ?
B1 C1 C2 C3 -180.0(8) . . . . ?
C1 C2 C3 C4 -1.8(13) . . . . ?
C2 C3 C4 C5 2.3(13) . . . . ?
C2 C3 C4 I1 -177.7(7) . . . . ?
C3 C4 C5 C6 -1.8(13) . . . . ?
I1 C4 C5 C6 178.2(6) . . . . ?
C2 C1 C6 C5 -0.4(13) . . . . ?
B1 C1 C6 C5 -179.5(8) . . . . ?
C4 C5 C6 C1 0.9(13) . . . . ?
C11 N1 C7 C8 -4.8(13) . . . . ?
N1 C7 C8 C9 6.5(12) . . . . ?
N1 C7 C8 C12 -179.4(7) . . . . ?
C7 C8 C9 C10 -3.9(11) . . . . ?
C12 C8 C9 C10 -177.6(7) . . . . ?
C8 C9 C10 C11 0.2(13) . . . . ?
C7 N1 C11 C10 0.6(13) . . . . ?
C9 C10 C11 N1 1.7(14) . . . . ?
C9 C8 C12 O3 175.1(7) . . . . ?
C7 C8 C12 O3 1.5(11) . . . . ?
C9 C8 C12 N2 -8.1(10) . . . . ?
C7 C8 C12 N2 178.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.001
_refine_diff_density_min         -2.226
_refine_diff_density_rms         0.158
####################################################################### 
# 
# 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_?
_database_code_depnum_ccdc_archive 'CCDC 1024940'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;

loop_
_audit_conform_dict_name
_audit_conform_dict_version
_audit_conform_dict_location
cif_core.dic . ftp://ftp.iucr.org/pub/cif_core.dic
cif_pd.dic . ftp://ftp.iucr.org/pub/cif_pd.dic

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            
'cocrystal of phenylboronic acid with L-proline (1:1)'
_chemical_formula_moiety         'C6 H7 B O2, C5 H9 N O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C11 H16 B1 N1 O4'
_chemical_formula_weight         237.06
_chemical_melting_point          ?
_chemical_compound_source        'see text'
_chemical_properties_physical    
'transforms into the hydrate form, moisture-sensitive'
_exptl_crystal_recrystallization_method 
'solvent assisted grinding: ethanol, chloroform, acetonitrile, acetone and THF'

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'

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   12.179(5)
_cell_length_b                   9.055(4)
_cell_length_c                   5.6453(22)
_cell_angle_alpha                90
_cell_angle_beta                 95.1941(18)
_cell_angle_gamma                90
_cell_volume                     620.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'Not Measured'
_cell_special_details            
; ?
;

_pd_spec_size_axial              10 # perpendicular to 
# equatorial plane
_pd_spec_size_equat              10 # parallel to 
# scattering vector 
# in transmission
_pd_spec_size_thick              ? # perpendicular to 
# scattering vector 
# in transmission

_pd_spec_mounting                'Packed between thin slides of cellophane'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   flat_sheet
_pd_char_particle_morphology     'white powder (visual)'
_pd_char_colour                  white

_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             293

_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_type   ? # include if applicable
_exptl_absorpt_process_details   ? # include if applicable
_exptl_absorpt_correction_T_min  ? # include if applicable
_exptl_absorpt_correction_T_max  ? # include if applicable

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_pd_instr_location               
; ?
;
_pd_calibration_special_details  
; ?
;
_diffrn_ambient_temperature      293
_diffrn_source                   X-ray
_diffrn_source_target            ?
_diffrn_source_type              'Bruker AXS'
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_measurement_device_type  'Bruker D8 ADVANCE'
_diffrn_detector                 'position sensitive detector'
_diffrn_detector_type            LynxEye
_pd_meas_scan_method             cont
_pd_meas_special_details         
;  ?
;

_diffrn_radiation_wavelength     1.5406
_diffrn_radiation_monochromator  'Ge (111)'

_pd_meas_number_of_points        2253
_pd_meas_2theta_range_min        5.0
_pd_meas_2theta_range_max        48.85545
_pd_meas_2theta_range_inc        0.01947

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?


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

# 8. REFINEMENT DATA

_pd_proc_ls_special_details      
; A Rietveld refinement with GSAS was performed to the best solution obtained 
from the simulating annealing implemented in TOPAS. The molecular units of 
phenylboronic acid and L-proline where represented as rigid bodies and 
were allowed to refine freely. Preferred orientation of the crystallites was 
described with a spherical harmonics function of 4th order.
;

_pd_proc_ls_profile_function     
;
CW Profile function number 3 with  19 terms
 Pseudovoigt profile coefficients as parameterized in
 P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83.
 Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994).
 J. Appl. Cryst.,27,892-900.
 #1(GU)   =   47.073 #2(GV)   =    5.534 #3(GW)   =    2.252
 #4(GP)   =    0.000 #5(LX)   =    0.000 #6(LY)   =   14.555
 #7(S/L)  =   0.0220 #8(H/L)  =   0.0232
 #9(trns) =    -1.66 #10(shft)=   1.4144
 #11(stec)=     0.00 #12(ptec)=     0.00 #13(sfec)=     0.00
 #14(L11) =    0.000 #15(L22) =    0.000 #16(L33) =    0.000
 #17(L12) =    0.000 #18(L13) =    0.000 #19(L23) =    0.000
 Peak tails are ignored  where the intensity is below 0.0010 times the peak
   Aniso. broadening axis   0.0   0.0   1.0
;
_pd_proc_ls_peak_cutoff          0.00100
_pd_proc_ls_background_function  
;   GSAS Background function number 1 with 10 terms.
 Shifted Chebyshev function of 1st kind
      1:    924.510     2:   -656.274     3:    211.103     4:   -76.3364    
      5:    87.7017     6:   -89.5386     7:    65.1972     8:   -27.9137    
      9:    15.1611    10:   -10.5593      
;
_pd_proc_ls_pref_orient_corr     
; ?
;

_pd_proc_ls_prof_R_factor        0.0576
_pd_proc_ls_prof_wR_factor       0.0795
_pd_proc_ls_prof_wR_expected     0.0271
_refine_ls_R_I_factor            ?
_refine_ls_R_Fsqd_factor         0.11395
_refine_ls_R_factor_all          ?

_refine_special_details          
; ?
;

_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_goodness_of_fit_all   2.97
_refine_ls_restrained_S_all      ?
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.00

_pd_proc_2theta_range_min        5.0007
_pd_proc_2theta_range_max        48.85615
_pd_proc_2theta_range_inc        0.01947
_pd_proc_wavelength              ?
_pd_block_diffractogram_id       ?
_pd_proc_info_excluded_regions   
'EXAMPLE 20 to 21 degrees unreliable due to beam dump'
_pd_proc_info_data_reduction     ?

_computing_data_collection       ?
_computing_cell_refinement       Topas
_computing_data_reduction        Topas
_computing_structure_solution    Topas
_computing_structure_refinement  GSAS
_computing_molecular_graphics    'Mercury 3.3.2'
_computing_publication_material  'GSAS, WINGX and Platon'


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


# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uiso 0.2933(6) 0.2624(19) 0.8722(16) 1.000 0.061(3) . . . .
O2 O Uiso 0.3194(6) -0.0001(18) 0.7795(11) 1.000 0.061(3) . . . .
C1 C Uiso 0.1633(4) 0.1414(12) 0.5472(9) 1.000 0.061(3) . . . .
C2 C Uiso 0.1514(2) 0.0362(8) 0.3616(5) 1.000 0.061(3) . . . .
C3 C Uiso 0.06378(12) 0.0437(4) 0.1832(3) 1.000 0.061(3) . . . .
O3 O Uiso 0.4298(4) 0.2405(10) 0.2451(17) 1.000 0.061(3) . . . .
C4 C Uiso -0.0149(4) 0.1570(5) 0.1876(10) 1.000 0.061(3) . . . .
O4 O Uiso 0.49748(4) 0.0239(14) 0.1029(11) 1.000 0.061(3) . . . .
C5 C Uiso -0.0057(6) 0.2618(10) 0.3721(17) 1.000 0.061(3) . . . .
C6 C Uiso 0.0825(6) 0.2534(12) 0.5498(15) 1.000 0.061(3) . . . .
B1 B Uiso 0.2621(5) 0.1337(16) 0.7435(10) 1.000 0.061(3) . . . .
N1 N Uiso 0.6332(2) -0.0351(15) 0.5083(17) 1.000 0.061(3) . . . .
C7 C Uiso 0.49064(17) 0.1215(12) 0.2686(10) 1.000 0.061(3) . . . .
C8 C Uiso 0.5518(2) 0.0953(14) 0.5138(11) 1.000 0.061(3) . . . .
C9 C Uiso 0.6215(3) 0.2272(16) 0.6228(17) 1.000 0.061(3) . . . .
C10 C Uiso 0.7173(3) 0.1514(19) 0.7783(14) 1.000 0.061(3) . . . .
C11 C Uiso 0.7454(3) 0.0144(18) 0.6327(17) 1.000 0.061(3) . . . .
H1' H Uiso 0.3398(7) 0.252(2) 0.9903(16) 1.000 0.0720 . . . .
H2 H Uiso 0.2037(3) -0.0387(10) 0.3598(8) 1.000 0.0720 . . . .
H2' H Uiso 0.3764(7) -0.001(2) 0.8751(13) 1.000 0.0720 . . . .
H3 H Uiso 0.05650(11) -0.0266(3) 0.0626(3) 1.000 0.0720 . . . .
H4 H Uiso -0.0725(4) 0.1621(5) 0.0679(12) 1.000 0.0720 . . . .
H5 H Uiso -0.0576(9) 0.3368(12) 0.377(2) 1.000 0.0720 . . . .
H6 H Uiso 0.0879(8) 0.3226(15) 0.672(2) 1.000 0.0720 . . . .
H1A H Uiso 0.6403(2) -0.0662(15) 0.3666(19) 1.000 0.0720 . . . .
H1B H Uiso 0.6085(4) -0.1096(15) 0.582(2) 1.000 0.0720 . . . .
H8 H Uiso 0.4967(3) 0.0665(15) 0.6212(9) 1.000 0.0720 . . . .
H9A H Uiso 0.6490(4) 0.2869(15) 0.498(2) 1.000 0.0720 . . . .
H9B H Uiso 0.5781(4) 0.2897(18) 0.718(2) 1.000 0.0720 . . . .
H10A H Uiso 0.7807(4) 0.216(2) 0.8083(17) 1.000 0.0720 . . . .
H10B H Uiso 0.6931(4) 0.121(2) 0.9300(13) 1.000 0.0720 . . . .
H11A H Uiso 0.79306(17) 0.0389(18) 0.5098(17) 1.000 0.0720 . . . .
H11B H Uiso 0.7769(4) -0.0673(19) 0.727(2) 1.000 0.0720 . . . .


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


# 10. MOLECULAR GEOMETRY (PLATON)

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.41(2) . . yes
O2 B1 1.404(19) . . yes
O1 H1' 0.840(12) . . no
O2 H2' 0.840(11) . . no
C1 B1 1.562(8) . . yes
C1 C2 1.414(10) . . no
C1 C6 1.414(13) . . no
C2 C3 1.401(3) . . no
C3 C4 1.406(6) . . no
O3 C7 1.308(12) . . yes
O4 C7 1.295(13) . . yes
C4 C5 1.406(11) . . no
C5 C6 1.404(12) . . no
N1 C11 1.545(10) . . yes
N1 C8 1.544(14) . . yes
C2 H2 0.931(9) . . no
C3 H3 0.930(4) . . no
C4 H4 0.930(8) . . no
C5 H5 0.930(14) . . no
C6 H6 0.930(16) . . no
N1 H1A 0.860(15) . . no
N1 H1B 0.861(17) . . no
C7 C8 1.530(8) . . no
C8 C9 1.559(16) . . no
C9 C10 1.555(13) . . no
C10 C11 1.54(2) . . no
C8 H8 0.980(8) . . no
C9 H9A 0.971(16) . . no
C9 H9B 0.970(16) . . no
C10 H10A 0.971(16) . . no
C10 H10B 0.970(12) . . no
C11 H11A 0.970(11) . . no
C11 H11B 0.97(2) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 H1' 117(2) . . . no
B1 O2 H2' 118.2(19) . . . no
C2 C1 C6 117.8(5) . . . no
C2 C1 B1 121.1(7) . . . yes
C6 C1 B1 121.1(8) . . . yes
C1 C2 C3 121.4(5) . . . no
C2 C3 C4 119.9(4) . . . no
C3 C4 C5 119.8(5) . . . no
C4 C5 C6 119.8(7) . . . no
C1 C6 C5 121.3(8) . . . no
O2 B1 C1 118.8(10) . . . yes
O1 B1 O2 122.2(7) . . . yes
O1 B1 C1 119.0(10) . . . yes
C8 N1 C11 108.2(10) . . . yes
C3 C2 H2 120.3(6) . . . no
C1 C2 H2 118.3(5) . . . no
C2 C3 H3 120.6(4) . . . no
C4 C3 H3 119.5(3) . . . no
C5 C4 H4 120.6(6) . . . no
C3 C4 H4 119.6(6) . . . no
C4 C5 H5 120.4(11) . . . no
C6 C5 H5 119.8(12) . . . no
C1 C6 H6 119.2(10) . . . no
C5 C6 H6 119.5(11) . . . no
C8 N1 H1B 109.7(8) . . . no
C11 N1 H1A 111.0(5) . . . no
C8 N1 H1A 112.8(11) . . . no
H1A N1 H1B 105.2(18) . . . no
C11 N1 H1B 109.9(11) . . . no
O3 C7 C8 116.4(8) . . . yes
O3 C7 O4 124.2(7) . . . yes
O4 C7 C8 119.3(8) . . . yes
N1 C8 C7 111.2(7) . . . yes
N1 C8 C9 105.4(5) . . . yes
C7 C8 C9 116.2(9) . . . no
C8 C9 C10 103.8(11) . . . no
C9 C10 C11 104.2(8) . . . no
N1 C11 C10 104.2(6) . . . yes
N1 C8 H8 106.6(12) . . . no
C7 C8 H8 107.3(4) . . . no
C9 C8 H8 109.8(9) . . . no
C8 C9 H9A 110.6(11) . . . no
C8 C9 H9B 111.2(8) . . . no
C10 C9 H9A 111.4(6) . . . no
C10 C9 H9B 111.3(10) . . . no
H9A C9 H9B 108.6(18) . . . no
C9 C10 H10A 112.1(16) . . . no
C9 C10 H10B 110.6(7) . . . no
C11 C10 H10A 111.5(10) . . . no
C11 C10 H10B 110.0(18) . . . no
H10A C10 H10B 108.5(12) . . . no
N1 C11 H11A 107.7(9) . . . no
N1 C11 H11B 108.5(14) . . . no
C10 C11 H11A 111.9(16) . . . no
C10 C11 H11B 114.6(12) . . . no
H11A C11 H11B 109.5(12) . . . no

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
C6 C1 C2 C3 1.2(9) . . . . no
B1 C1 C2 C3 -179.1(6) . . . . no
C2 C1 C6 C5 -1.1(12) . . . . no
B1 C1 C6 C5 179.2(8) . . . . no
C6 C1 B1 O2 160.2(8) . . . . no
C2 C1 B1 O1 158.1(7) . . . . no
C6 C1 B1 O1 -22.2(11) . . . . no
C2 C1 B1 O2 -19.5(10) . . . . no
C1 C2 C3 C4 -0.4(7) . . . . no
C2 C3 C4 C5 -0.4(7) . . . . no
C3 C4 C5 C6 0.5(10) . . . . no
C4 C5 C6 C1 0.3(13) . . . . no
C8 N1 C11 C10 18.0(11) . . . . no
C11 N1 C8 C7 131.9(7) . . . . no
C11 N1 C8 C9 5.2(9) . . . . no
O3 C7 C8 N1 -171.7(7) . . . . no
O3 C7 C8 C9 -51.2(6) . . . . no
O4 C7 C8 N1 11.4(9) . . . . no
O4 C7 C8 C9 132.0(7) . . . . no
N1 C8 C9 C10 -26.2(7) . . . . no
C7 C8 C9 C10 -149.8(5) . . . . no
C8 C9 C10 C11 37.7(8) . . . . no
C9 C10 C11 N1 -34.3(11) . . . . no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1' O3 0.840(12) 1.731(12) 2.569(12) 175.5(15) 1_556 yes
N1 H1A O4 0.860(15) 2.332(10) 2.751(10) 110.3(8) 1_555 yes
N1 H1A O1 0.860(15) 2.253(18) 3.021(17) 148.7(13) 2_646 yes
N1 H1B O3 0.861(17) 1.759(15) 2.617(15) 173.9(10) 2_646 yes
O2 H2' O4 0.840(11) 1.880(9) 2.714(8) 171.8(19) 1_556 yes
C8 H8 O2 0.980(8) 2.485(10) 3.432(9) 162.5(5) 1_555 yes
C9 H9A O2 0.971(16) 2.536(18) 3.474(17) 162.3(11) 2_656 yes
C9 H9B O4 0.970(16) 2.556(18) 3.482(16) 159.6(13) 2_656 yes

#===END
####################################################################### 
# 
# 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_jul4drem
_database_code_depnum_ccdc_archive 'CCDC 1024941'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N O2, C6 H7 B O2, H2 O'
_chemical_formula_sum            'C11 H18 B N O5'
_chemical_formula_weight         255.07

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.6856(14)
_cell_length_b                   5.8462(11)
_cell_length_c                   14.933(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.953(3)
_cell_angle_gamma                90.00
_cell_volume                     651.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3882
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.63

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6342
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1268
_reflns_number_gt                1224
_reflns_threshold_expression     >2sigma(I)

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

_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.

 Due to the absence of heavy atoms, the data have been merged for the 
 refinement.
 OH and NH hydrogens have been located from iterative examination of 
 difference Fourier maps following least squares refinements of the 
 previous models with the following restraints
 DFIX 0.84 0.01 for OH and DFIX 0.86 0.01 for NH
 Isotropic displacement parameters of these H atoms were set to
 Uiso=1.5Ueq(C) or  1.5Ueq (O,N).
 For the refinement of the O1-H1 hydrogen, a DANG restraint was employed
 DANG 1.85 0.01 B1 H1
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0689P)²+0.0965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1268
_refine_ls_number_parameters     181
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.5432(5) 0.5837(8) 0.7489(3) 0.0457(9) Uani 1 1 d D . .
N1 N 0.1230(3) 0.2256(4) 0.89307(16) 0.0330(6) Uani 1 1 d D . .
H1A H 0.209(3) 0.218(8) 0.9420(13) 0.050 Uiso 1 1 d D . .
H1B H 0.054(4) 0.338(4) 0.899(2) 0.050 Uiso 1 1 d D . .
O1 O 0.6929(4) 0.4752(6) 0.7934(2) 0.0885(12) Uani 1 1 d D . .
H1' H 0.753(4) 0.548(5) 0.839(3) 0.133 Uiso 1 1 d D . .
O2 O 0.4830(4) 0.7747(6) 0.78045(18) 0.0710(9) Uani 1 1 d D . .
H2' H 0.539(6) 0.814(12) 0.8338(17) 0.106 Uiso 1 1 d D . .
O3 O -0.0196(3) -0.3510(4) 0.92269(14) 0.0376(5) Uani 1 1 d . . .
O4 O 0.2415(2) -0.1730(4) 0.97104(14) 0.0405(5) Uani 1 1 d . . .
O5 O 0.5954(3) 0.9170(3) 0.96133(17) 0.0465(6) Uani 1 1 d D . .
H5A H 0.642(5) 1.044(3) 0.980(3) 0.070 Uiso 1 1 d D . .
H5B H 0.492(2) 0.933(9) 0.969(2) 0.070 Uiso 1 1 d D . .
C1 C 0.4336(4) 0.4778(6) 0.6563(2) 0.0401(7) Uani 1 1 d . . .
C2 C 0.2874(4) 0.5935(7) 0.6015(2) 0.0509(9) Uani 1 1 d . . .
H2 H 0.2539 0.7344 0.6209 0.061 Uiso 1 1 calc R . .
C3 C 0.1919(5) 0.5033(10) 0.5192(2) 0.0669(12) Uani 1 1 d . . .
H3 H 0.0950 0.5832 0.4835 0.080 Uiso 1 1 calc R . .
C4 C 0.2393(5) 0.2956(10) 0.4897(2) 0.0642(11) Uani 1 1 d . . .
H4 H 0.1749 0.2350 0.4340 0.077 Uiso 1 1 calc R . .
C5 C 0.3807(5) 0.1779(7) 0.5420(2) 0.0557(9) Uani 1 1 d . . .
H5 H 0.4126 0.0368 0.5220 0.067 Uiso 1 1 calc R . .
C6 C 0.4764(4) 0.2674(6) 0.6243(2) 0.0472(8) Uani 1 1 d . . .
H6 H 0.5723 0.1848 0.6594 0.057 Uiso 1 1 calc R . .
C7 C 0.0824(3) -0.1832(5) 0.92651(17) 0.0281(6) Uani 1 1 d . . .
C8 C 0.0031(4) 0.0217(5) 0.86892(18) 0.0324(6) Uani 1 1 d . . .
H8 H -0.1153 0.0565 0.8792 0.039 Uiso 1 1 calc R . .
C9 C -0.0124(5) -0.0155(7) 0.7656(2) 0.0519(9) Uani 1 1 d . . .
H9A H 0.0565 -0.1482 0.7558 0.062 Uiso 1 1 calc R . .
H9B H -0.1366 -0.0383 0.7331 0.062 Uiso 1 1 calc R . .
C10 C 0.0614(5) 0.1989(8) 0.7323(2) 0.0605(10) Uani 1 1 d . . .
H10A H 0.1124 0.1661 0.6803 0.073 Uiso 1 1 calc R . .
H10B H -0.0316 0.3136 0.7141 0.073 Uiso 1 1 calc R . .
C11 C 0.2017(4) 0.2773(7) 0.8129(2) 0.0488(8) Uani 1 1 d . . .
H11A H 0.2244 0.4398 0.8089 0.059 Uiso 1 1 calc R . .
H11B H 0.3129 0.1943 0.8176 0.059 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.0392(19) 0.049(2) 0.051(2) -0.0027(18) 0.0151(16) -0.0091(17)
N1 0.0370(13) 0.0247(13) 0.0371(11) 0.0024(10) 0.0083(10) 0.0018(10)
O1 0.0645(17) 0.087(3) 0.092(2) -0.041(2) -0.0255(15) 0.0237(18)
O2 0.0785(18) 0.068(2) 0.0602(15) -0.0170(16) 0.0043(13) 0.0134(17)
O3 0.0370(10) 0.0254(10) 0.0498(11) 0.0034(9) 0.0093(9) -0.0049(9)
O4 0.0295(10) 0.0348(11) 0.0539(12) 0.0072(10) 0.0033(8) 0.0017(9)
O5 0.0351(12) 0.0378(12) 0.0655(14) -0.0121(11) 0.0099(11) -0.0032(10)
C1 0.0389(15) 0.0436(19) 0.0421(15) 0.0047(14) 0.0179(13) -0.0041(14)
C2 0.0521(19) 0.056(2) 0.0460(17) 0.0073(16) 0.0141(15) 0.0072(17)
C3 0.055(2) 0.095(3) 0.0474(19) 0.013(2) 0.0052(16) 0.015(2)
C4 0.059(2) 0.091(3) 0.0412(17) -0.005(2) 0.0082(16) -0.013(2)
C5 0.070(2) 0.049(2) 0.0528(19) -0.0087(17) 0.0257(18) -0.011(2)
C6 0.0445(16) 0.049(2) 0.0486(17) 0.0060(16) 0.0111(14) 0.0019(16)
C7 0.0300(13) 0.0272(14) 0.0295(13) -0.0017(11) 0.0119(10) 0.0019(12)
C8 0.0322(14) 0.0287(15) 0.0366(14) 0.0014(13) 0.0089(11) 0.0037(12)
C9 0.068(2) 0.048(2) 0.0367(15) 0.0038(15) 0.0054(14) -0.0038(19)
C10 0.074(2) 0.068(3) 0.0444(17) 0.0117(19) 0.0235(17) 0.003(2)
C11 0.0550(18) 0.041(2) 0.0583(18) 0.0039(16) 0.0291(16) -0.0013(16)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O2 1.338(5) . ?
B1 O1 1.341(5) . ?
B1 C1 1.562(5) . ?
N1 C8 1.497(4) . ?
N1 C11 1.497(4) . ?
O3 C7 1.248(3) . ?
O4 C7 1.245(3) . ?
C1 C6 1.388(5) . ?
C1 C2 1.395(4) . ?
C2 C3 1.376(6) . ?
C3 C4 1.370(7) . ?
C4 C5 1.362(6) . ?
C5 C6 1.374(5) . ?
C7 C8 1.514(4) . ?
C8 C9 1.534(4) . ?
C9 C10 1.508(6) . ?
C10 C11 1.482(5) . ?

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
O2 B1 O1 123.2(3) . . ?
O2 B1 C1 118.9(3) . . ?
O1 B1 C1 117.8(3) . . ?
C8 N1 C11 108.2(2) . . ?
C6 C1 C2 116.9(3) . . ?
C6 C1 B1 122.3(3) . . ?
C2 C1 B1 120.9(3) . . ?
C3 C2 C1 121.3(4) . . ?
C4 C3 C2 120.0(4) . . ?
C5 C4 C3 120.1(4) . . ?
C4 C5 C6 120.1(4) . . ?
C5 C6 C1 121.7(3) . . ?
O4 C7 O3 126.0(3) . . ?
O4 C7 C8 118.3(3) . . ?
O3 C7 C8 115.7(2) . . ?
N1 C8 C7 110.7(2) . . ?
N1 C8 C9 104.4(2) . . ?
C7 C8 C9 112.5(3) . . ?
C10 C9 C8 105.6(3) . . ?
C11 C10 C9 104.3(3) . . ?
C10 C11 N1 103.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 B1 C1 C6 -172.8(3) . . . . ?
O1 B1 C1 C6 6.4(5) . . . . ?
O2 B1 C1 C2 7.6(5) . . . . ?
O1 B1 C1 C2 -173.2(3) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
B1 C1 C2 C3 179.0(3) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
B1 C1 C6 C5 -178.9(3) . . . . ?
C11 N1 C8 C7 111.0(3) . . . . ?
C11 N1 C8 C9 -10.3(3) . . . . ?
O4 C7 C8 N1 -12.8(3) . . . . ?
O3 C7 C8 N1 168.8(2) . . . . ?
O4 C7 C8 C9 103.6(3) . . . . ?
O3 C7 C8 C9 -74.8(3) . . . . ?
N1 C8 C9 C10 -13.1(3) . . . . ?
C7 C8 C9 C10 -133.2(3) . . . . ?
C8 C9 C10 C11 31.9(4) . . . . ?
C9 C10 C11 N1 -37.7(4) . . . . ?
C8 N1 C11 C10 30.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.035
