# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_C12H16BNO4
_database_code_depnum_ccdc_archive 'CCDC 1906646'
loop_
_audit_author_name
_audit_author_address
'Kaicheng Li'
;Boston College
United States of America
;
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 B N O4'
_chemical_formula_sum            'C12 H16 B N O4'
_chemical_formula_weight         249.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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.
;

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

_cell_length_a                   11.3174(2)
_cell_length_b                   13.2547(3)
_cell_length_c                   7.8913(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1183.76(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5015
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      69.29

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.851
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2016). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7352
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.334
_diffrn_reflns_theta_max         69.741
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             2045
_reflns_number_gt                1996
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.837
_reflns_Friedel_fraction_full    0.870

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.1919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2045
_refine_ls_number_parameters     173
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.065
_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_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 0.36060(12) 0.73344(11) 0.5203(2) 0.0171(3) Uani 1 1 d . . . . .
O2 O 0.75678(12) 0.84632(10) 0.43064(19) 0.0142(3) Uani 1 1 d D . . . .
H2O H 0.793(2) 0.8269(18) 0.516(3) 0.017 Uiso 1 1 d D U . . .
O3 O 0.61317(11) 0.81793(10) 0.22221(18) 0.0136(3) Uani 1 1 d . . . . .
O4 O 0.37667(12) 1.02074(11) 0.24945(19) 0.0165(3) Uani 1 1 d D . . . .
H4O H 0.333(2) 1.0613(19) 0.302(3) 0.020 Uiso 1 1 d D U . . .
N1 N 0.53456(14) 0.82911(12) 0.5079(2) 0.0113(4) Uani 1 1 d D . . . .
H1N H 0.556(2) 0.8765(18) 0.583(3) 0.014 Uiso 1 1 d D U . . .
C1 C 0.47645(17) 0.74017(15) 0.5937(3) 0.0129(4) Uani 1 1 d . . . . .
C2 C 0.54997(17) 0.64924(15) 0.5452(3) 0.0139(4) Uani 1 1 d . . . . .
C3 C 0.52744(19) 0.55215(16) 0.6033(3) 0.0177(4) Uani 1 1 d . . . . .
H3 H 0.460267 0.538236 0.671632 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6059(2) 0.47598(15) 0.5588(3) 0.0212(5) Uani 1 1 d . . . . .
H4 H 0.592565 0.409106 0.597634 0.025 Uiso 1 1 calc R U . . .
C5 C 0.70378(19) 0.49669(16) 0.4578(3) 0.0203(5) Uani 1 1 d . . . . .
H5 H 0.757248 0.444161 0.428970 0.024 Uiso 1 1 calc R U . . .
C6 C 0.72336(18) 0.59403(15) 0.3990(3) 0.0172(4) Uani 1 1 d . . . . .
H6 H 0.789444 0.607488 0.328335 0.021 Uiso 1 1 calc R U . . .
C7 C 0.64651(17) 0.67243(14) 0.4432(3) 0.0136(4) Uani 1 1 d . . . . .
C8 C 0.48785(17) 0.81777(14) 0.2174(3) 0.0146(4) Uani 1 1 d . . . . .
H8A H 0.457331 0.747870 0.211005 0.017 Uiso 1 1 calc R U . . .
H8B H 0.458885 0.855823 0.117728 0.017 Uiso 1 1 calc R U . . .
C9 C 0.44790(16) 0.86855(15) 0.3818(3) 0.0132(4) Uani 1 1 d . . . . .
C10 C 0.33111(18) 0.82873(16) 0.4477(3) 0.0184(4) Uani 1 1 d . . . . .
H10A H 0.297481 0.874644 0.534103 0.022 Uiso 1 1 calc R U . . .
H10B H 0.273417 0.820669 0.354390 0.022 Uiso 1 1 calc R U . . .
C11 C 0.46771(18) 0.75667(16) 0.7833(3) 0.0155(4) Uani 1 1 d . . . . .
H11A H 0.424067 0.819117 0.805798 0.023 Uiso 1 1 calc R U . . .
H11B H 0.547283 0.761895 0.831531 0.023 Uiso 1 1 calc R U . . .
H11C H 0.426127 0.699678 0.835315 0.023 Uiso 1 1 calc R U . . .
C12 C 0.45687(17) 0.98330(16) 0.3731(3) 0.0158(4) Uani 1 1 d . . . . .
H12A H 0.437957 1.012695 0.485220 0.019 Uiso 1 1 calc R U . . .
H12B H 0.538531 1.003148 0.342902 0.019 Uiso 1 1 calc R U . . .
B1 B 0.65283(19) 0.78957(16) 0.3923(3) 0.0125(4) 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 C10 1.426(2) . ?
O1 C1 1.436(2) . ?
O2 B1 1.429(3) . ?
O2 H2O 0.83(2) . ?
O3 C8 1.419(2) . ?
O3 B1 1.464(3) . ?
O4 C12 1.422(3) . ?
O4 H4O 0.84(2) . ?
N1 C9 1.492(3) . ?
N1 C1 1.510(2) . ?
N1 B1 1.703(3) . ?
N1 H1N 0.90(2) . ?
C1 C2 1.514(3) . ?
C1 C11 1.516(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(3) . ?
C6 H6 0.9500 . ?
C7 B1 1.605(3) . ?
C8 C9 1.530(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.515(3) . ?
C9 C12 1.526(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C1 108.70(15) . . ?
B1 O2 H2O 114.5(18) . . ?
C8 O3 B1 109.32(14) . . ?
C12 O4 H4O 105.1(19) . . ?
C9 N1 C1 106.64(15) . . ?
C9 N1 B1 105.51(15) . . ?
C1 N1 B1 110.02(14) . . ?
C9 N1 H1N 112.0(16) . . ?
C1 N1 H1N 111.4(16) . . ?
B1 N1 H1N 110.9(15) . . ?
O1 C1 N1 105.38(15) . . ?
O1 C1 C2 110.52(17) . . ?
N1 C1 C2 105.59(16) . . ?
O1 C1 C11 110.33(17) . . ?
N1 C1 C11 111.01(17) . . ?
C2 C1 C11 113.61(18) . . ?
C3 C2 C7 122.65(19) . . ?
C3 C2 C1 123.57(19) . . ?
C7 C2 C1 113.70(17) . . ?
C4 C3 C2 118.2(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.08(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 117.91(18) . . ?
C2 C7 B1 113.17(17) . . ?
C6 C7 B1 128.92(18) . . ?
O3 C8 C9 105.77(15) . . ?
O3 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O3 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
N1 C9 C10 102.86(16) . . ?
N1 C9 C12 109.61(16) . . ?
C10 C9 C12 114.88(16) . . ?
N1 C9 C8 102.54(15) . . ?
C10 C9 C8 113.30(17) . . ?
C12 C9 C8 112.38(17) . . ?
O1 C10 C9 104.02(16) . . ?
O1 C10 H10A 111.0 . . ?
C9 C10 H10A 111.0 . . ?
O1 C10 H10B 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 C9 109.64(17) . . ?
O4 C12 H12A 109.7 . . ?
C9 C12 H12A 109.7 . . ?
O4 C12 H12B 109.7 . . ?
C9 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O2 B1 O3 108.15(16) . . ?
O2 B1 C7 119.52(17) . . ?
O3 B1 C7 117.66(17) . . ?
O2 B1 N1 111.82(15) . . ?
O3 B1 N1 99.85(14) . . ?
C7 B1 N1 97.38(14) . . ?

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
C10 O1 C1 N1 -20.7(2) . . . . ?
C10 O1 C1 C2 -134.30(18) . . . . ?
C10 O1 C1 C11 99.22(19) . . . . ?
C9 N1 C1 O1 -1.7(2) . . . . ?
B1 N1 C1 O1 -115.63(16) . . . . ?
C9 N1 C1 C2 115.33(18) . . . . ?
B1 N1 C1 C2 1.4(2) . . . . ?
C9 N1 C1 C11 -121.13(17) . . . . ?
B1 N1 C1 C11 124.92(18) . . . . ?
O1 C1 C2 C3 -68.5(3) . . . . ?
N1 C1 C2 C3 178.00(19) . . . . ?
C11 C1 C2 C3 56.1(3) . . . . ?
O1 C1 C2 C7 114.57(19) . . . . ?
N1 C1 C2 C7 1.1(2) . . . . ?
C11 C1 C2 C7 -120.79(19) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -175.8(2) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C1 C2 C7 C6 176.72(19) . . . . ?
C3 C2 C7 B1 179.76(19) . . . . ?
C1 C2 C7 B1 -3.3(2) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C5 C6 C7 B1 179.2(2) . . . . ?
B1 O3 C8 C9 43.05(18) . . . . ?
C1 N1 C9 C10 21.5(2) . . . . ?
B1 N1 C9 C10 138.44(15) . . . . ?
C1 N1 C9 C12 144.09(17) . . . . ?
B1 N1 C9 C12 -98.92(18) . . . . ?
C1 N1 C9 C8 -96.35(17) . . . . ?
B1 N1 C9 C8 20.64(18) . . . . ?
O3 C8 C9 N1 -38.64(18) . . . . ?
O3 C8 C9 C10 -148.77(16) . . . . ?
O3 C8 C9 C12 78.96(18) . . . . ?
C1 O1 C10 C9 34.5(2) . . . . ?
N1 C9 C10 O1 -33.8(2) . . . . ?
C12 C9 C10 O1 -152.83(18) . . . . ?
C8 C9 C10 O1 76.1(2) . . . . ?
N1 C9 C12 O4 178.34(15) . . . . ?
C10 C9 C12 O4 -66.5(2) . . . . ?
C8 C9 C12 O4 65.0(2) . . . . ?
C8 O3 B1 O2 -144.11(15) . . . . ?
C8 O3 B1 C7 76.7(2) . . . . ?
C8 O3 B1 N1 -27.12(17) . . . . ?
C2 C7 B1 O2 123.9(2) . . . . ?
C6 C7 B1 O2 -56.1(3) . . . . ?
C2 C7 B1 O3 -101.6(2) . . . . ?
C6 C7 B1 O3 78.4(3) . . . . ?
C2 C7 B1 N1 3.6(2) . . . . ?
C6 C7 B1 N1 -176.4(2) . . . . ?
C9 N1 B1 O2 116.48(18) . . . . ?
C1 N1 B1 O2 -128.85(17) . . . . ?
C9 N1 B1 O3 2.27(18) . . . . ?
C1 N1 B1 O3 116.94(16) . . . . ?
C9 N1 B1 C7 -117.57(15) . . . . ?
C1 N1 B1 C7 -2.90(19) . . . . ?

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
O2 H2O O3 0.83(2) 1.95(2) 2.757(2) 165(2) 4_655
O4 H4O O2 0.84(2) 1.81(2) 2.644(2) 172(3) 3_475
N1 H1N O4 0.90(2) 2.04(2) 2.933(2) 174(2) 2_675

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_C11H14BNO4
_database_code_depnum_ccdc_archive 'CCDC 1906647'
loop_
_audit_author_name
_audit_author_address
'Kaicheng Li'
;Boston College
United States of America
;
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 B N O4'
_chemical_formula_sum            'C11 H14 B N O4'
_chemical_formula_weight         235.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   13.3622(6)
_cell_length_b                   9.2625(4)
_cell_length_c                   8.6950(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.734(2)
_cell_angle_gamma                90
_cell_volume                     1072.49(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5244
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      69.78

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.906
_shelx_estimated_absorpt_T_min   0.702
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2016). TWINABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3453
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.819
_diffrn_reflns_theta_max         69.802
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3453
_reflns_number_gt                3035
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;


_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0916P)²+0.3126P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3453
_refine_ls_number_parameters     164
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_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 0.65621(11) 0.39639(17) 0.66853(19) 0.0302(4) Uani 1 1 d . . . . .
O2 O 0.93047(11) 0.69456(18) 0.55584(18) 0.0280(4) Uani 1 1 d D . . . .
H2O H 0.914(2) 0.744(3) 0.478(3) 0.034 Uiso 1 1 d D U . . .
O3 O 0.89297(11) 0.62686(16) 0.80962(18) 0.0270(4) Uani 1 1 d . . . . .
O4 O 0.88113(12) 0.16113(17) 0.83713(18) 0.0269(4) Uani 1 1 d D . . . .
H4O H 0.9432(16) 0.175(3) 0.869(3) 0.032 Uiso 1 1 d D U . . .
N1 N 0.80790(13) 0.4893(2) 0.5997(2) 0.0245(4) Uani 1 1 d D . . . .
H1N H 0.8354(18) 0.453(3) 0.519(3) 0.029 Uiso 1 1 d D U . . .
B1 B 0.85285(19) 0.6541(3) 0.6501(3) 0.0263(5) Uani 1 1 d . . . . .
C1 C 0.69531(16) 0.4978(2) 0.5669(3) 0.0276(5) Uani 1 1 d . . . . .
H1 H 0.675643 0.470609 0.457220 0.033 Uiso 1 1 calc R U . . .
C2 C 0.66773(17) 0.6530(3) 0.5952(3) 0.0290(5) Uani 1 1 d . . . . .
C3 C 0.56932(18) 0.7044(3) 0.5810(3) 0.0351(6) Uani 1 1 d . . . . .
H3 H 0.514898 0.641979 0.550370 0.042 Uiso 1 1 calc R U . . .
C4 C 0.55274(18) 0.8482(3) 0.6126(3) 0.0366(6) Uani 1 1 d . . . . .
H4 H 0.486183 0.885132 0.604647 0.044 Uiso 1 1 calc R U . . .
C5 C 0.63292(19) 0.9393(3) 0.6561(3) 0.0331(5) Uani 1 1 d . . . . .
H5 H 0.620769 1.038088 0.677020 0.040 Uiso 1 1 calc R U . . .
C6 C 0.73047(18) 0.8868(2) 0.6690(3) 0.0298(5) Uani 1 1 d . . . . .
H6 H 0.784767 0.949591 0.699252 0.036 Uiso 1 1 calc R U . . .
C7 C 0.74898(16) 0.7419(2) 0.6376(3) 0.0266(5) Uani 1 1 d . . . . .
C8 C 0.90979(16) 0.4784(2) 0.8381(3) 0.0260(5) Uani 1 1 d . . . . .
H8A H 0.906178 0.456871 0.949063 0.031 Uiso 1 1 calc R U . . .
H8B H 0.976956 0.450002 0.808413 0.031 Uiso 1 1 calc R U . . .
C9 C 0.82764(17) 0.3965(2) 0.7408(2) 0.0249(5) Uani 1 1 d . . . . .
C10 C 0.72466(17) 0.3992(3) 0.8047(3) 0.0290(5) Uani 1 1 d . . . . .
H10A H 0.715179 0.313995 0.870658 0.035 Uiso 1 1 calc R U . . .
H10B H 0.715791 0.488007 0.865552 0.035 Uiso 1 1 calc R U . . .
C11 C 0.85933(16) 0.2440(2) 0.7003(3) 0.0263(5) Uani 1 1 d . . . . .
H11A H 0.804710 0.197029 0.634526 0.032 Uiso 1 1 calc R U . . .
H11B H 0.919561 0.248386 0.641331 0.032 Uiso 1 1 calc R U . . .


_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 1.418(3) . ?
O1 C10 1.436(3) . ?
O2 B1 1.424(3) . ?
O2 H2O 0.84(2) . ?
O3 C8 1.412(3) . ?
O3 B1 1.467(3) . ?
O4 C11 1.426(3) . ?
O4 H4O 0.86(2) . ?
N1 C9 1.504(3) . ?
N1 C1 1.510(3) . ?
N1 B1 1.685(3) . ?
N1 H1N 0.88(2) . ?
B1 C7 1.604(3) . ?
C1 C2 1.510(3) . ?
C1 H1 1.0000 . ?
C2 C7 1.388(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.531(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.524(3) . ?
C9 C10 1.526(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C10 105.04(16) . . ?
B1 O2 H2O 116.9(19) . . ?
C8 O3 B1 111.98(17) . . ?
C11 O4 H4O 108.0(19) . . ?
C9 N1 C1 106.76(16) . . ?
C9 N1 B1 105.73(16) . . ?
C1 N1 B1 109.30(16) . . ?
C9 N1 H1N 112.0(18) . . ?
C1 N1 H1N 110.1(17) . . ?
B1 N1 H1N 112.7(18) . . ?
O2 B1 O3 111.26(18) . . ?
O2 B1 C7 119.67(19) . . ?
O3 B1 C7 113.44(19) . . ?
O2 B1 N1 110.45(18) . . ?
O3 B1 N1 100.63(17) . . ?
C7 B1 N1 98.84(16) . . ?
O1 C1 N1 105.11(17) . . ?
O1 C1 C2 114.93(19) . . ?
N1 C1 C2 105.73(18) . . ?
O1 C1 H1 110.3 . . ?
N1 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
C7 C2 C3 122.1(2) . . ?
C7 C2 C1 114.3(2) . . ?
C3 C2 C1 123.5(2) . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 118.4(2) . . ?
C2 C7 B1 111.8(2) . . ?
C6 C7 B1 129.8(2) . . ?
O3 C8 C9 106.82(17) . . ?
O3 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
O3 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
N1 C9 C11 111.98(17) . . ?
N1 C9 C10 100.65(17) . . ?
C11 C9 C10 112.09(19) . . ?
N1 C9 C8 103.69(17) . . ?
C11 C9 C8 112.78(18) . . ?
C10 C9 C8 114.67(19) . . ?
O1 C10 C9 103.40(18) . . ?
O1 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
O1 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
O4 C11 C9 110.32(18) . . ?
O4 C11 H11A 109.6 . . ?
C9 C11 H11A 109.6 . . ?
O4 C11 H11B 109.6 . . ?
C9 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?

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
C8 O3 B1 O2 -97.2(2) . . . . ?
C8 O3 B1 C7 124.41(19) . . . . ?
C8 O3 B1 N1 19.8(2) . . . . ?
C9 N1 B1 O2 119.07(19) . . . . ?
C1 N1 B1 O2 -126.34(19) . . . . ?
C9 N1 B1 O3 1.4(2) . . . . ?
C1 N1 B1 O3 116.03(18) . . . . ?
C9 N1 B1 C7 -114.58(18) . . . . ?
C1 N1 B1 C7 0.0(2) . . . . ?
C10 O1 C1 N1 33.3(2) . . . . ?
C10 O1 C1 C2 -82.5(2) . . . . ?
C9 N1 C1 O1 -8.8(2) . . . . ?
B1 N1 C1 O1 -122.76(18) . . . . ?
C9 N1 C1 C2 113.14(19) . . . . ?
B1 N1 C1 C2 -0.8(2) . . . . ?
O1 C1 C2 C7 116.9(2) . . . . ?
N1 C1 C2 C7 1.4(3) . . . . ?
O1 C1 C2 C3 -62.9(3) . . . . ?
N1 C1 C2 C3 -178.3(2) . . . . ?
C7 C2 C3 C4 -0.9(4) . . . . ?
C1 C2 C3 C4 178.8(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C3 C2 C7 C6 1.0(4) . . . . ?
C1 C2 C7 C6 -178.81(19) . . . . ?
C3 C2 C7 B1 178.2(2) . . . . ?
C1 C2 C7 B1 -1.5(3) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C5 C6 C7 B1 -177.4(2) . . . . ?
O2 B1 C7 C2 120.6(2) . . . . ?
O3 B1 C7 C2 -104.8(2) . . . . ?
N1 B1 C7 C2 0.9(2) . . . . ?
O2 B1 C7 C6 -62.5(3) . . . . ?
O3 B1 C7 C6 72.1(3) . . . . ?
N1 B1 C7 C6 177.8(2) . . . . ?
B1 O3 C8 C9 -34.1(2) . . . . ?
C1 N1 C9 C11 102.2(2) . . . . ?
B1 N1 C9 C11 -141.47(18) . . . . ?
C1 N1 C9 C10 -17.0(2) . . . . ?
B1 N1 C9 C10 99.29(18) . . . . ?
C1 N1 C9 C8 -135.92(18) . . . . ?
B1 N1 C9 C8 -19.6(2) . . . . ?
O3 C8 C9 N1 32.6(2) . . . . ?
O3 C8 C9 C11 153.95(18) . . . . ?
O3 C8 C9 C10 -76.1(2) . . . . ?
C1 O1 C10 C9 -44.9(2) . . . . ?
N1 C9 C10 O1 37.1(2) . . . . ?
C11 C9 C10 O1 -82.0(2) . . . . ?
C8 C9 C10 O1 147.70(17) . . . . ?
N1 C9 C11 O4 177.73(16) . . . . ?
C10 C9 C11 O4 -70.0(2) . . . . ?
C8 C9 C11 O4 61.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O3 0.84(2) 1.89(2) 2.719(2) 171(3) 4_575
O4 H4O O2 0.86(2) 1.77(2) 2.629(2) 176(3) 2_746
N1 H1N O4 0.88(2) 2.04(2) 2.912(2) 169(2) 4_565

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.060

