# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1900255'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 O4, 2(H2 O), 2(C5 H7 B N O2)'
_chemical_formula_sum            'C14 H18 B2 N2 O10'
_chemical_formula_weight         395.92
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'I 1 2/m 1'
_space_group_name_Hall           '-I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   3.7455(3)
_cell_length_b                   10.5330(6)
_cell_length_c                   21.5313(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.556(6)
_cell_angle_gamma                90
_cell_volume                     846.75(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1268
_cell_measurement_temperature    250
_cell_measurement_theta_max      28.9530
_cell_measurement_theta_min      3.8000
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2893
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.001
_diffrn_reflns_theta_min         3.442
_diffrn_ambient_temperature      250
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -52.00   1.00   10.00    --  -17.60 134.00  14.00    5
  2  ω     28.00  33.00   1.00   10.00    --  -17.60  70.00  90.00    5
  3  ω     28.00  33.00   1.00   10.00    --   19.16 -70.00  90.00    5
  4  ω    -15.00  23.00   1.00   15.00    --  -17.75 -99.00  30.00   38
  5  ω     44.00  94.00   1.00   15.00    --   19.00-178.00 -30.00   50
  6  ω      2.00  83.00   1.00   15.00    --   19.00  38.00  90.00   81
  7  ω    -22.00  55.00   1.00   15.00    --   19.00 -99.00-180.00   77
  8  ω    -53.00  45.00   1.00   15.00    --   19.00 -38.00 -90.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0218117000
_diffrn_orient_matrix_UB_12      0.0644058000
_diffrn_orient_matrix_UB_13      -0.0084945000
_diffrn_orient_matrix_UB_21      0.1886492000
_diffrn_orient_matrix_UB_22      -0.0077171000
_diffrn_orient_matrix_UB_23      0.0032572000
_diffrn_orient_matrix_UB_31      -0.0021540000
_diffrn_orient_matrix_UB_32      -0.0179835000
_diffrn_orient_matrix_UB_33      -0.0317935000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                782
_reflns_number_total             884
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.3930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Free rotating group:
 O3(H3A)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.8322(3) 0.65396(9) 0.56665(4) 0.0367(3) Uani 1 1 d . . . . .
O3 O 0.500000 0.85555(13) 0.500000 0.0416(4) Uani 1 2 d S T P . .
H3A H 0.361101 0.807133 0.477671 0.062 Uiso 1 1 d G . . . .
N1 N 0.2422(4) 0.500000 0.89508(7) 0.0353(4) Uani 1 2 d S T P . .
H1 H 0.173541 0.500000 0.932744 0.042 Uiso 1 2 calc RS T P . .
O1 O 0.6262(4) 0.61335(11) 0.68103(5) 0.0554(4) Uani 1 1 d . . . . .
H1A H 0.689652 0.603976 0.645250 0.083 Uiso 1 1 calc GR . . . .
C1 C 0.9251(3) 0.56895(12) 0.53032(5) 0.0265(3) Uani 1 1 d . . . . .
C2 C 0.4580(5) 0.500000 0.77603(8) 0.0280(4) Uani 1 2 d S T P . .
C3 C 0.4035(4) 0.61190(15) 0.80753(7) 0.0399(4) Uani 1 1 d . . . . .
H3 H 0.442148 0.690015 0.788050 0.048 Uiso 1 1 calc R . . . .
C4 C 0.2932(4) 0.61047(15) 0.86709(7) 0.0425(4) Uani 1 1 d . . . . .
H4 H 0.254240 0.687138 0.887848 0.051 Uiso 1 1 calc R . . . .
B1 B 0.5799(6) 0.500000 0.70660(9) 0.0293(5) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2562(15) . ?
O3 H3A 0.8498 . ?
O3 H3A 0.850(19) 2_656 ?
N1 H1 0.8700 . ?
N1 C4 1.3311(17) . ?
N1 C4 1.3312(17) 6_565 ?
O1 H1A 0.8300 . ?
O1 B1 1.3317(14) . ?
C1 C1 1.452(2) 6_565 ?
C1 C1 1.461(2) 2_756 ?
C2 C3 1.3831(18) . ?
C2 C3 1.3831(18) 6_565 ?
C2 B1 1.598(3) . ?
C3 H3 0.9400 . ?
C3 C4 1.378(2) . ?
C4 H4 0.9400 . ?

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
H3A O3 H3A 106.2 . 2_656 ?
C4 N1 H1 119.1 . . ?
C4 N1 H1 119.1 6_565 . ?
C4 N1 C4 121.88(17) . 6_565 ?
B1 O1 H1A 109.5 . . ?
O2 C1 C1 135.46(7) . 6_565 ?
O2 C1 C1 134.53(7) . 2_756 ?
C1 C1 C1 90.0 6_565 2_756 ?
C3 C2 C3 116.90(17) . 6_565 ?
C3 C2 B1 121.55(9) 6_565 . ?
C3 C2 B1 121.55(9) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.92(14) . . ?
C4 C3 H3 119.5 . . ?
N1 C4 C3 119.69(14) . . ?
N1 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
O1 B1 O1 127.40(18) 6_565 . ?
O1 B1 C2 116.30(9) 6_565 . ?
O1 B1 C2 116.30(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.174
_oxdiff_exptl_absorpt_empirical_full_min 0.810
####################################################################### 
# 
# 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_1a-Bpy
_database_code_depnum_ccdc_archive 'CCDC 1900258'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 O4, 2(C5 H6.8 B N O2), C10 H8.4 N2'
_chemical_formula_sum            'C24 H22 B2 N4 O8'
_chemical_formula_weight         516.07
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.3874(6)
_cell_length_b                   10.7643(4)
_cell_length_c                   8.7610(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.765(5)
_cell_angle_gamma                90
_cell_volume                     1154.56(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1184
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.9070
_cell_measurement_theta_min      3.6120
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2546
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.021
_diffrn_reflns_theta_min         3.270
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  48.00   1.00   14.34    --  -16.52  57.00 -30.00   76
  2  ω    -25.00   1.00   1.00   14.34    --  -16.52 -99.00   0.00   26
  3  ω    -65.00 -38.00   1.00   14.34    --  -16.52-178.00 -30.00   27
  4  ω    -79.00  -4.00   1.00   14.34    --  -16.52 -57.00-150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0479032000
_diffrn_orient_matrix_UB_12      -0.0202678000
_diffrn_orient_matrix_UB_13      -0.0482640000
_diffrn_orient_matrix_UB_21      -0.0253957000
_diffrn_orient_matrix_UB_22      -0.0109993000
_diffrn_orient_matrix_UB_23      0.0660483000
_diffrn_orient_matrix_UB_31      -0.0202904000
_diffrn_orient_matrix_UB_32      0.0617817000
_diffrn_orient_matrix_UB_33      -0.0041380000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1094
_reflns_number_total             1388
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.1668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.4) H2A(0.1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C3(H3), C4(H4), C5(H5), C6(H6)
3.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.92159(10) 0.64953(10) 0.13068(13) 0.0544(4) Uani 1 1 d . . . . .
O2 O 0.85568(11) 0.61185(9) 0.39845(13) 0.0549(4) Uani 1 1 d . . . . .
H2 H 0.8763 0.6032 0.3144 0.082 Uiso 1 1 calc GR . . . .
N1 N 0.69879(13) 0.5000 0.88153(18) 0.0374(4) Uani 1 2 d S T P . .
H1 H 0.6707 0.5000 0.9654 0.045 Uiso 0.8 2 calc RS T P A 1
N2 N 0.60133(14) 0.5000 1.14324(19) 0.0404(4) Uani 1 2 d S T P . .
H2A H 0.6273 0.5000 1.0577 0.049 Uiso 0.2 2 calc RS T P B 2
C7 C 0.52150(15) 0.5000 1.4247(2) 0.0314(4) Uani 1 2 d S T P . .
C1 C 0.96487(11) 0.56750(12) 0.05947(15) 0.0341(3) Uani 1 1 d . . . . .
C2 C 0.79038(15) 0.5000 0.6160(2) 0.0327(4) Uani 1 2 d S T P . .
C3 C 0.76578(13) 0.60972(13) 0.68537(16) 0.0389(4) Uani 1 1 d . . . . .
H3 H 0.7804 0.6854 0.6415 0.047 Uiso 1 1 calc R . . . .
C4 C 0.71994(13) 0.60770(14) 0.81848(17) 0.0411(4) Uani 1 1 d . . . . .
H4 H 0.7037 0.6819 0.8645 0.049 Uiso 1 1 calc R . . . .
C5 C 0.58037(14) 0.60530(15) 1.21219(17) 0.0457(4) Uani 1 1 d . . . . .
H5 H 0.5926 0.6800 1.1643 0.055 Uiso 1 1 calc R . . . .
C6 C 0.54150(13) 0.60910(14) 1.35109(16) 0.0427(4) Uani 1 1 d . . . . .
H6 H 0.5287 0.6852 1.3954 0.051 Uiso 1 1 calc R . . . .
B1 B 0.83885(18) 0.5000 0.4575(3) 0.0357(5) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2483(16) . ?
O2 B1 1.3393(13) . ?
N1 C4 1.3274(16) . ?
N1 C4 1.3273(16) 6_565 ?
N2 C5 1.3284(17) . ?
N2 C5 1.3285(17) 6_565 ?
C7 C7 1.497(3) 5_668 ?
C7 C6 1.3802(17) 6_565 ?
C7 C6 1.3802(17) . ?
C1 C1 1.453(3) 6_565 ?
C1 C1 1.456(3) 2_755 ?
C2 C3 1.3833(16) . ?
C2 C3 1.3833(16) 6_565 ?
C2 B1 1.594(3) . ?
C3 C4 1.3729(19) . ?
C5 C6 1.376(2) . ?
B1 O2 1.3393(13) 6_565 ?

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
C4 N1 C4 121.71(17) 6_565 . ?
C5 N2 C5 117.13(16) . 6_565 ?
C6 C7 C7 121.69(8) 6_565 5_668 ?
C6 C7 C7 121.69(8) . 5_668 ?
C6 C7 C6 116.61(17) . 6_565 ?
O1 C1 C1 134.98(7) . 2_755 ?
O1 C1 C1 135.02(7) . 6_565 ?
C1 C1 C1 90.000(1) 6_565 2_755 ?
C3 C2 C3 117.24(17) 6_565 . ?
C3 C2 B1 121.33(8) 6_565 . ?
C3 C2 B1 121.33(8) . . ?
C4 C3 C2 120.47(13) . . ?
N1 C4 C3 120.05(14) . . ?
N2 C5 C6 123.13(14) . . ?
C5 C6 C7 119.99(14) . . ?
O2 B1 O2 128.04(18) 6_565 . ?
O2 B1 C2 115.97(9) 6_565 . ?
O2 B1 C2 115.97(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.052
_oxdiff_exptl_absorpt_empirical_full_min 0.961
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1900257'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 O4, 2(H2 O), 2(C11 H11 B N O2)'
_chemical_formula_sum            'C26 H26 B2 N2 O10'
_chemical_formula_weight         548.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.9208(4)
_cell_length_b                   10.4450(9)
_cell_length_c                   29.717(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.340(9)
_cell_angle_gamma                90
_cell_volume                     1216.97(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1142
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.9310
_cell_measurement_theta_min      3.9460
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.820
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            4924
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.177
_diffrn_reflns_theta_min         3.365
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.820
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  24.00   0.50    5.83    --  -16.67 -99.00-150.00   78
  2  ω    -82.00 -11.00   0.50    5.83    --  -16.67 -77.00  60.00  142
  3  ω    -45.00  41.00   0.50    5.83    --  -16.67  77.00 -30.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0333519000
_diffrn_orient_matrix_UB_12      0.0178118000
_diffrn_orient_matrix_UB_13      0.0226215000
_diffrn_orient_matrix_UB_21      -0.1776939000
_diffrn_orient_matrix_UB_22      0.0010852000
_diffrn_orient_matrix_UB_23      0.0043117000
_diffrn_orient_matrix_UB_31      0.0060425000
_diffrn_orient_matrix_UB_32      -0.0655498000
_diffrn_orient_matrix_UB_33      0.0062479000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1739
_reflns_number_total             2712
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0778P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C8(H8), C7(H7), C4(H4A), C10(H10), C13(H13), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8343(4) 0.65471(13) 0.45022(5) 0.0472(4) Uani 1 1 d . . . . .
O2 O 1.2271(4) 0.65376(13) 0.54596(5) 0.0458(4) Uani 1 1 d . . . . .
O5 O 0.5351(4) 0.85326(14) 0.49876(5) 0.0510(5) Uani 1 1 d . . . . .
H5A H 0.642679 0.804313 0.480951 0.076 Uiso 1 1 d G . . . .
H5B H 0.411940 0.802968 0.514221 0.076 Uiso 1 1 d G . . . .
O4 O 0.4979(5) 0.38596(14) 0.37087(5) 0.0555(5) Uani 1 1 d . . . . .
H4 H 0.565817 0.396384 0.396764 0.083 Uiso 1 1 calc GR . . . .
O3 O 0.6114(5) 0.61189(14) 0.36583(5) 0.0545(5) Uani 1 1 d . . . . .
H3 H 0.678006 0.601400 0.391781 0.082 Uiso 1 1 calc GR . . . .
N1 N -0.2155(5) 0.48876(16) 0.07396(6) 0.0455(5) Uani 1 1 d . . . . .
H1 H -0.295744 0.487619 0.046969 0.055 Uiso 1 1 calc R . . . .
C6 C 0.1536(5) 0.49542(16) 0.20779(6) 0.0313(4) Uani 1 1 d . . . . .
C3 C 0.3667(5) 0.49948(17) 0.29872(7) 0.0337(5) Uani 1 1 d . . . . .
C5 C 0.3355(5) 0.59847(18) 0.22514(6) 0.0354(5) Uani 1 1 d . . . . .
H5 H 0.388612 0.667100 0.206522 0.043 Uiso 1 1 calc R . . . .
C9 C 0.0333(5) 0.49312(17) 0.16048(6) 0.0324(5) Uani 1 1 d . . . . .
C8 C 0.1852(5) 0.39784(19) 0.28092(6) 0.0369(5) Uani 1 1 d . . . . .
H8 H 0.133863 0.328785 0.299444 0.044 Uiso 1 1 calc R . . . .
C7 C 0.0777(5) 0.39515(18) 0.23673(6) 0.0356(5) Uani 1 1 d . . . . .
H7 H -0.047071 0.325508 0.226164 0.043 Uiso 1 1 calc R . . . .
C4 C 0.4383(5) 0.60051(19) 0.26951(6) 0.0363(5) Uani 1 1 d . . . . .
H4A H 0.558530 0.670977 0.280291 0.044 Uiso 1 1 calc R . . . .
C1 C 0.9249(5) 0.56926(19) 0.47758(6) 0.0370(5) Uani 1 1 d . . . . .
C2 C 1.1007(5) 0.56966(19) 0.52081(6) 0.0365(5) Uani 1 1 d . . . . .
C10 C 0.0209(5) 0.6028(2) 0.13405(7) 0.0428(5) Uani 1 1 d . . . . .
H10 H 0.100408 0.679866 0.145731 0.051 Uiso 1 1 calc R . . . .
C13 C -0.0802(6) 0.3802(2) 0.14034(7) 0.0447(5) Uani 1 1 d . . . . .
H13 H -0.071500 0.303827 0.156421 0.054 Uiso 1 1 calc R . . . .
C11 C -0.1062(6) 0.5991(2) 0.09126(7) 0.0479(6) Uani 1 1 d . . . . .
H11 H -0.116497 0.673640 0.074170 0.058 Uiso 1 1 calc R . . . .
C12 C -0.2038(6) 0.3803(2) 0.09735(7) 0.0477(6) Uani 1 1 d . . . . .
H12 H -0.279938 0.304398 0.084371 0.057 Uiso 1 1 calc R . . . .
B1 B 0.5011(6) 0.4992(2) 0.34890(8) 0.0370(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.257(2) . ?
O2 C2 1.254(2) . ?
O4 B1 1.351(2) . ?
O3 B1 1.350(2) . ?
N1 C11 1.332(3) . ?
N1 C12 1.330(2) . ?
C6 C5 1.389(2) . ?
C6 C9 1.480(3) . ?
C6 C7 1.389(2) . ?
C3 C8 1.382(2) . ?
C3 C4 1.396(3) . ?
C3 B1 1.579(3) . ?
C5 C4 1.376(3) . ?
C9 C10 1.390(3) . ?
C9 C13 1.395(3) . ?
C8 C7 1.377(3) . ?
C1 C2 1.454(3) . ?
C1 C2 1.455(3) 3_766 ?
C10 C11 1.363(3) . ?
C13 C12 1.364(3) . ?

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
C12 N1 C11 121.71(19) . . ?
C5 C6 C9 121.69(17) . . ?
C7 C6 C5 117.78(18) . . ?
C7 C6 C9 120.50(17) . . ?
C8 C3 C4 116.61(18) . . ?
C8 C3 B1 121.89(17) . . ?
C4 C3 B1 121.45(17) . . ?
C4 C5 C6 120.97(18) . . ?
C10 C9 C6 122.24(17) . . ?
C10 C9 C13 116.40(19) . . ?
C13 C9 C6 121.36(17) . . ?
C7 C8 C3 122.33(18) . . ?
C8 C7 C6 120.64(18) . . ?
C5 C4 C3 121.68(18) . . ?
O1 C1 C2 134.42(19) . . ?
O1 C1 C2 135.22(19) . 3_766 ?
C2 C1 C2 90.36(16) . 3_766 ?
O2 C2 C1 135.41(19) . . ?
O2 C2 C1 134.93(19) . 3_766 ?
C1 C2 C1 89.64(16) . 3_766 ?
C11 C10 C9 121.0(2) . . ?
C12 C13 C9 120.8(2) . . ?
N1 C11 C10 119.9(2) . . ?
N1 C12 C13 120.1(2) . . ?
O4 B1 C3 117.02(18) . . ?
O3 B1 O4 125.95(19) . . ?
O3 B1 C3 117.03(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.415
_oxdiff_exptl_absorpt_empirical_full_min 0.673
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1900256'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2019-02-28 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 O4, 2(C5 H7 B N O2), H2 O'
_chemical_formula_sum            'C14 H16 B2 N2 O9'
_chemical_formula_weight         377.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5211(5)
_cell_length_b                   21.0309(9)
_cell_length_c                   7.6551(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.368(5)
_cell_angle_gamma                90
_cell_volume                     1671.24(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1687
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.9040
_cell_measurement_theta_min      3.6240
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light pink'
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.822
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6685
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.822
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.221
_diffrn_reflns_theta_min         3.216
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.822
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  23.00   1.00   44.92    --  -16.52 -99.00 -30.00   33
  2  ω    -84.00   0.00   1.00   44.92    --  -16.52 -57.00 120.00   84
  3  ω    -68.00  -2.00   1.00   44.92    --  -16.52 -57.00  30.00   66
  4  ω     35.00  61.00   1.00   44.92    --   17.61 178.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0365916000
_diffrn_orient_matrix_UB_12      -0.0047759000
_diffrn_orient_matrix_UB_13      -0.0690261000
_diffrn_orient_matrix_UB_21      -0.0571399000
_diffrn_orient_matrix_UB_22      -0.0079563000
_diffrn_orient_matrix_UB_23      -0.0586096000
_diffrn_orient_matrix_UB_31      -0.0085338000
_diffrn_orient_matrix_UB_32      0.0324136000
_diffrn_orient_matrix_UB_33      -0.0245968000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2338
_reflns_number_total             3735
_reflns_odcompleteness_completeness 97.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1298
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C11(H11), C9(H9), C6(H6A), C8(H8), C14(H14), C7(H7), C12(H12),
  C13(H13)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6), O8(H8A), O5(H5), O7(H7A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47407(13) 0.30640(6) 0.58752(18) 0.0457(4) Uani 1 1 d . . . . .
O6 O 0.54580(14) 0.12847(6) 0.7043(2) 0.0462(4) Uani 1 1 d . . . . .
H6 H 0.495873 0.148433 0.630786 0.069 Uiso 1 1 calc GR . . . .
O3 O 0.11731(14) 0.24187(6) 0.20999(18) 0.0475(4) Uani 1 1 d . . . . .
O2 O 0.35818(14) 0.17068(6) 0.45162(19) 0.0481(4) Uani 1 1 d . . . . .
O4 O 0.22591(14) 0.37615(6) 0.36289(19) 0.0483(4) Uani 1 1 d . . . . .
O8 O 0.01259(15) 0.41983(7) 0.1683(2) 0.0530(4) Uani 1 1 d . . . . .
H8A H 0.073501 0.398585 0.217270 0.079 Uiso 1 1 calc GR . . . .
O9 O 0.27717(18) 0.07451(6) 0.2091(2) 0.0580(5) Uani 1 1 d . . . . .
H9A H 0.298626 0.106162 0.276574 0.087 Uiso 1 1 d G . . . .
H9B H 0.264730 0.090152 0.105333 0.087 Uiso 1 1 d G . . . .
O5 O 0.65144(15) 0.22973(7) 0.7536(2) 0.0570(5) Uani 1 1 d . . . . .
H5 H 0.587116 0.242458 0.687804 0.085 Uiso 1 1 calc GR . . . .
O7 O -0.05734(16) 0.32013(7) 0.0373(2) 0.0613(5) Uani 1 1 d . . . . .
H7A H 0.005174 0.306561 0.105112 0.092 Uiso 1 1 calc GR . . . .
N1 N 0.95744(16) 0.14578(8) 1.0948(2) 0.0420(4) Uani 1 1 d . . . . .
H1 H 1.019373 0.169943 1.142743 0.050 Uiso 1 1 calc R . . . .
N2 N -0.40245(16) 0.40277(8) -0.2129(2) 0.0435(5) Uani 1 1 d . . . . .
H2 H -0.459620 0.378565 -0.272507 0.052 Uiso 1 1 calc R . . . .
C10 C -0.19923(19) 0.41346(9) -0.0314(2) 0.0338(5) Uani 1 1 d . . . . .
C5 C 0.75610(19) 0.13546(9) 0.9087(2) 0.0349(5) Uani 1 1 d . . . . .
C3 C 0.21602(19) 0.25885(9) 0.3142(3) 0.0352(5) Uani 1 1 d . . . . .
C1 C 0.37573(19) 0.28886(9) 0.4837(3) 0.0359(5) Uani 1 1 d . . . . .
C2 C 0.3244(2) 0.22725(9) 0.4214(3) 0.0356(5) Uani 1 1 d . . . . .
C11 C -0.29343(19) 0.37692(9) -0.1290(3) 0.0366(5) Uani 1 1 d . . . . .
H11 H -0.280988 0.333292 -0.136756 0.044 Uiso 1 1 calc R . . . .
C4 C 0.26527(19) 0.32002(10) 0.3806(2) 0.0350(5) Uani 1 1 d . . . . .
C9 C 0.7645(2) 0.07081(9) 0.9407(3) 0.0388(5) Uani 1 1 d . . . . .
H9 H 0.699077 0.044250 0.886513 0.047 Uiso 1 1 calc R . . . .
C6 C 0.85681(19) 0.17196(9) 0.9905(3) 0.0398(5) Uani 1 1 d . . . . .
H6A H 0.854910 0.215733 0.972988 0.048 Uiso 1 1 calc R . . . .
C8 C 0.8682(2) 0.04490(10) 1.0517(3) 0.0426(5) Uani 1 1 d . . . . .
H8 H 0.871710 0.001450 1.074557 0.051 Uiso 1 1 calc R . . . .
C14 C -0.2235(2) 0.47797(9) -0.0257(3) 0.0438(5) Uani 1 1 d . . . . .
H14 H -0.162331 0.504398 0.038950 0.053 Uiso 1 1 calc R . . . .
C7 C 0.9650(2) 0.08380(10) 1.1269(3) 0.0425(5) Uani 1 1 d . . . . .
H7 H 1.036221 0.067046 1.200519 0.051 Uiso 1 1 calc R . . . .
C12 C -0.4251(2) 0.46487(11) -0.2070(3) 0.0515(6) Uani 1 1 d . . . . .
H12 H -0.501870 0.481549 -0.266863 0.062 Uiso 1 1 calc R . . . .
C13 C -0.3360(2) 0.50404(10) -0.1133(3) 0.0527(6) Uani 1 1 d . . . . .
H13 H -0.350847 0.547551 -0.108688 0.063 Uiso 1 1 calc R . . . .
B1 B 0.6409(2) 0.16723(11) 0.7799(3) 0.0382(6) Uani 1 1 d . . . . .
B2 B -0.0712(2) 0.38193(11) 0.0662(3) 0.0363(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.253(2) . ?
O6 B1 1.346(3) . ?
O3 C3 1.254(2) . ?
O2 C2 1.252(2) . ?
O4 C4 1.251(2) . ?
O8 B2 1.342(3) . ?
O5 B1 1.337(3) . ?
O7 B2 1.330(3) . ?
N1 C6 1.337(2) . ?
N1 C7 1.327(2) . ?
N2 C11 1.336(2) . ?
N2 C12 1.330(3) . ?
C10 C11 1.375(3) . ?
C10 C14 1.383(3) . ?
C10 B2 1.576(3) . ?
C5 C9 1.382(3) . ?
C5 C6 1.374(3) . ?
C5 B1 1.580(3) . ?
C3 C2 1.453(3) . ?
C3 C4 1.448(3) . ?
C1 C2 1.454(3) . ?
C1 C4 1.451(3) . ?
C9 C8 1.381(3) . ?
C8 C7 1.360(3) . ?
C14 C13 1.375(3) . ?
C12 C13 1.361(3) . ?

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
C7 N1 C6 122.25(17) . . ?
C12 N2 C11 121.87(18) . . ?
C11 C10 C14 116.42(18) . . ?
C11 C10 B2 120.48(17) . . ?
C14 C10 B2 123.10(17) . . ?
C9 C5 B1 123.16(18) . . ?
C6 C5 C9 116.53(18) . . ?
C6 C5 B1 120.27(17) . . ?
O3 C3 C2 136.18(18) . . ?
O3 C3 C4 133.49(18) . . ?
C4 C3 C2 90.31(15) . . ?
O1 C1 C2 134.01(19) . . ?
O1 C1 C4 135.86(18) . . ?
C4 C1 C2 90.11(15) . . ?
O2 C2 C3 135.41(18) . . ?
O2 C2 C1 134.97(18) . . ?
C3 C2 C1 89.60(15) . . ?
N2 C11 C10 121.37(18) . . ?
O4 C4 C3 135.02(18) . . ?
O4 C4 C1 134.97(17) . . ?
C3 C4 C1 89.93(15) . . ?
C8 C9 C5 121.24(19) . . ?
N1 C6 C5 121.27(18) . . ?
C7 C8 C9 119.06(19) . . ?
C13 C14 C10 121.64(19) . . ?
N1 C7 C8 119.62(18) . . ?
N2 C12 C13 120.03(19) . . ?
C12 C13 C14 118.7(2) . . ?
O6 B1 C5 116.94(18) . . ?
O5 B1 O6 127.18(19) . . ?
O5 B1 C5 115.84(18) . . ?
O8 B2 C10 117.14(18) . . ?
O7 B2 O8 126.7(2) . . ?
O7 B2 C10 116.16(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.075
_oxdiff_exptl_absorpt_empirical_full_min 0.929
