# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_19294
_database_code_depnum_ccdc_archive 'CCDC 2119463'
loop_
_audit_author_name
_audit_author_address
'Peijun Liu'
;Zunyi Medical Univeristy
China
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-04-01 downloaded from the CCDC.
;
_audit_creation_date             2018-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(H2 O), C13 H16 B N5'
_chemical_formula_sum            'C13 H17 B N5 O0.50'
_chemical_formula_weight         262.12
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.1462(13)
_cell_length_b                   8.7576(7)
_cell_length_c                   25.691(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.499(9)
_cell_angle_gamma                90
_cell_volume                     2887.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2827
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.8690
_cell_measurement_theta_min      3.1570
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5648
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.463
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  53.00   1.00    8.00    --  -11.43  37.00   0.00   81
  2  ω    -84.00  13.00   1.00    8.00    --  -11.43 -37.00-180.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0113301000
_diffrn_orient_matrix_UB_12      -0.0376555000
_diffrn_orient_matrix_UB_13      0.0250357000
_diffrn_orient_matrix_UB_21      -0.0295919000
_diffrn_orient_matrix_UB_22      -0.0639682000
_diffrn_orient_matrix_UB_23      -0.0115494000
_diffrn_orient_matrix_UB_31      0.0453228000
_diffrn_orient_matrix_UB_32      -0.0322965000
_diffrn_orient_matrix_UB_33      -0.0063098000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2119
_reflns_number_total             2553
_reflns_odcompleteness_completeness 99.90
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.178
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.060
_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)+(0.0451P)²+1.9750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1147
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H1WA(0.5) H1WB(0.5)
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3), C10(H10), C11(H11), C4(H4)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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
O1W O 0.250000 0.0500(2) 0.500000 0.0402(5) Uani 1 2 d S T P . .
H1WA H 0.244744 0.103019 0.471838 0.060 Uiso 0.5 1 d G . . . .
H1WB H 0.278922 0.109415 0.525020 0.060 Uiso 0.5 1 d G . . . .
N3 N 0.42803(11) 0.39842(17) 0.63909(5) 0.0310(4) Uani 1 1 d . . . . .
N1 N 0.32735(12) 0.22438(17) 0.59541(5) 0.0316(4) Uani 1 1 d . . . . .
N2 N 0.39386(12) 0.33497(17) 0.59076(6) 0.0332(4) Uani 1 1 d . . . . .
N5 N 0.43026(12) 0.74422(17) 0.58133(6) 0.0335(4) Uani 1 1 d . . . . .
N4 N 0.55501(12) 0.62609(19) 0.55831(6) 0.0387(4) Uani 1 1 d . . . . .
C1 C 0.25205(13) 0.1052(2) 0.66644(6) 0.0290(4) Uani 1 1 d . . . . .
C7 C 0.31916(13) 0.2162(2) 0.64732(6) 0.0283(4) Uani 1 1 d . . . . .
C9 C 0.49917(14) 0.6308(2) 0.59654(7) 0.0317(4) Uani 1 1 d . . . . .
C8 C 0.38366(14) 0.3267(2) 0.67469(7) 0.0318(4) Uani 1 1 d . . . . .
C2 C 0.16343(14) 0.0453(2) 0.63269(7) 0.0342(4) Uani 1 1 d . . . . .
H2 H 0.145311 0.077793 0.597429 0.041 Uiso 1 1 calc R . . . .
C6 C 0.27726(15) 0.0543(2) 0.71932(7) 0.0336(4) Uani 1 1 d . . . . .
H6 H 0.335719 0.093144 0.742581 0.040 Uiso 1 1 calc R . . . .
C5 C 0.21596(15) -0.0533(2) 0.73722(7) 0.0384(5) Uani 1 1 d . . . . .
H5 H 0.233734 -0.086670 0.772388 0.046 Uiso 1 1 calc R . . . .
C3 C 0.10224(15) -0.0617(2) 0.65097(8) 0.0400(5) Uani 1 1 d . . . . .
H3 H 0.043240 -0.100175 0.628029 0.048 Uiso 1 1 calc R . . . .
C10 C 0.52120(17) 0.7359(2) 0.52038(7) 0.0451(5) Uani 1 1 d . . . . .
H10 H 0.547848 0.755001 0.490306 0.054 Uiso 1 1 calc R . . . .
C11 C 0.44328(16) 0.8098(2) 0.53467(7) 0.0417(5) Uani 1 1 d . . . . .
H11 H 0.405012 0.890364 0.516589 0.050 Uiso 1 1 calc R . . . .
C4 C 0.12831(16) -0.1118(2) 0.70326(8) 0.0411(5) Uani 1 1 d . . . . .
H4 H 0.087282 -0.184214 0.715486 0.049 Uiso 1 1 calc R . . . .
C12 C 0.35334(16) 0.7949(3) 0.61093(9) 0.0503(6) Uani 1 1 d . . . . .
H12A H 0.324730 0.707841 0.625387 0.075 Uiso 1 1 calc GR . . . .
H12B H 0.298523 0.849231 0.587426 0.075 Uiso 1 1 calc GR . . . .
H12C H 0.386166 0.861087 0.639442 0.075 Uiso 1 1 calc GR . . . .
B1 B 0.51266(19) 0.5282(3) 0.64911(9) 0.0388(5) Uani 1 1 d . . . . .
C13 C 0.63917(16) 0.5186(3) 0.55677(10) 0.0628(7) Uani 1 1 d . . . . .
H13A H 0.699686 0.546530 0.583269 0.094 Uiso 1 1 calc GR . . . .
H13B H 0.655564 0.521229 0.522139 0.094 Uiso 1 1 calc GR . . . .
H13C H 0.617618 0.417427 0.563895 0.094 Uiso 1 1 calc GR . . . .
H8 H 0.3981(14) 0.357(2) 0.7108(7) 0.038(5) Uiso 1 1 d . . . . .
H1A H 0.5908(16) 0.471(2) 0.6566(8) 0.051(6) Uiso 1 1 d . . . . .
H1B H 0.4990(15) 0.598(2) 0.6849(8) 0.049(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 N2 1.3457(19) . ?
N3 C8 1.342(2) . ?
N3 B1 1.573(3) . ?
N1 N2 1.327(2) . ?
N1 C7 1.363(2) . ?
N5 C9 1.344(2) . ?
N5 C11 1.373(2) . ?
N5 C12 1.460(2) . ?
N4 C9 1.348(2) . ?
N4 C10 1.373(3) . ?
N4 C13 1.460(3) . ?
C1 C7 1.467(2) . ?
C1 C2 1.395(2) . ?
C1 C6 1.400(2) . ?
C7 C8 1.376(3) . ?
C9 B1 1.599(3) . ?
C2 C3 1.381(3) . ?
C6 C5 1.381(3) . ?
C5 C4 1.384(3) . ?
C3 C4 1.384(3) . ?
C10 C11 1.329(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
N2 N3 B1 122.18(15) . . ?
C8 N3 N2 109.15(15) . . ?
C8 N3 B1 128.54(15) . . ?
N2 N1 C7 108.65(14) . . ?
N1 N2 N3 108.24(13) . . ?
C9 N5 C11 111.08(16) . . ?
C9 N5 C12 124.93(16) . . ?
C11 N5 C12 123.96(17) . . ?
C9 N4 C10 110.61(16) . . ?
C9 N4 C13 125.10(18) . . ?
C10 N4 C13 124.29(18) . . ?
C2 C1 C7 121.53(15) . . ?
C2 C1 C6 118.28(17) . . ?
C6 C1 C7 120.18(16) . . ?
N1 C7 C1 122.90(15) . . ?
N1 C7 C8 107.00(16) . . ?
C8 C7 C1 130.10(15) . . ?
N5 C9 N4 104.47(16) . . ?
N5 C9 B1 127.24(16) . . ?
N4 C9 B1 128.28(17) . . ?
N3 C8 C7 106.96(15) . . ?
C3 C2 C1 120.86(17) . . ?
C5 C6 C1 120.51(17) . . ?
C6 C5 C4 120.57(17) . . ?
C2 C3 C4 120.33(18) . . ?
C11 C10 N4 107.20(17) . . ?
C10 C11 N5 106.64(18) . . ?
C3 C4 C5 119.45(19) . . ?
N3 B1 C9 108.82(15) . . ?

_olex2_date_sample_data_collection 2018-11-17
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.712
_oxdiff_exptl_absorpt_empirical_full_min 0.452
