# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ura
_database_code_depnum_ccdc_archive 'CCDC 1440006'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ' ClPBA + Theophylline '
_chemical_melting_point          ?
_chemical_formula_moiety         ' C7 H8 N4 O2, C6 H6 B Cl O2 '
_chemical_formula_sum            'C13 H14 B Cl N4 O4'
_chemical_formula_weight         336.54

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ' Triclinic '
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.510(1)
_cell_length_b                   9.471(2)
_cell_length_c                   11.878(2)
_cell_angle_alpha                85.63(3)
_cell_angle_beta                 79.47(4)
_cell_angle_gamma                68.96(3)
_cell_volume                     775.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7555
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.03

_exptl_crystal_description       ' Plates '
_exptl_crystal_colour            ' Colorless '
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   'SADABS; Sheldrick, 96'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Brucker APEX-CCD Area Detector'
_diffrn_measurement_method       SMART
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7555
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2723
_reflns_number_gt                2176
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0875P)²+0.4220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2723
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.1947
_refine_ls_wR_factor_gt          0.1845
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7300(6) -0.6808(5) 0.7581(3) 0.0418(9) Uani 1 1 d . . .
Cl Cl 0.37455(18) -0.00058(11) 0.67205(10) 0.0722(4) Uani 1 1 d . . .
O1 O 0.7925(5) -0.7457(3) 0.8571(2) 0.0569(8) Uani 1 1 d . . .
H1A H 0.763(7) -0.682(6) 0.902(5) 0.088(18) Uiso 1 1 d . . .
O2 O 0.7436(4) -0.7716(3) 0.6723(2) 0.0529(7) Uani 1 1 d . . .
H2A H 0.810(6) -0.877(5) 0.680(4) 0.071(13) Uiso 1 1 d . . .
O3 O 1.1313(4) -1.6147(3) 0.63550(19) 0.0481(7) Uani 1 1 d . . .
O4 O 1.1727(4) -1.4145(3) 0.96350(19) 0.0526(7) Uani 1 1 d . . .
N1 N 0.9156(5) -1.0928(3) 0.6666(2) 0.0456(8) Uani 1 1 d . . .
N2 N 0.9566(5) -1.2837(3) 0.5532(2) 0.0424(7) Uani 1 1 d . . .
H2B H 0.936(6) -1.326(5) 0.499(4) 0.069(13) Uiso 1 1 d . . .
N3 N 1.0428(4) -1.2477(3) 0.8275(2) 0.0426(7) Uani 1 1 d . . .
N4 N 1.1535(4) -1.5116(3) 0.7984(2) 0.0387(7) Uani 1 1 d . . .
C1 C 0.4989(6) -0.2956(4) 0.6121(3) 0.0536(10) Uani 1 1 d . . .
H1 H 0.463(7) -0.249(5) 0.549(4) 0.086(16) Uiso 1 1 d . . .
C2 C 0.8969(6) -1.1355(4) 0.5655(3) 0.0479(9) Uani 1 1 d . . .
H2 H 0.843(6) -1.061(5) 0.509(3) 0.064(12) Uiso 1 1 d . . .
C3 C 0.5784(6) -0.4470(4) 0.6343(3) 0.0471(9) Uani 1 1 d . . .
H3 H 0.604(5) -0.518(4) 0.573(3) 0.050(10) Uiso 1 1 d . . .
C4 C 0.4753(5) -0.1953(4) 0.6971(3) 0.0483(9) Uani 1 1 d . . .
C5 C 0.6104(6) -0.3988(4) 0.8218(3) 0.0492(9) Uani 1 1 d . . .
H5 H 0.637(5) -0.430(4) 0.893(3) 0.056(11) Uiso 1 1 d . . .
C6 C 1.0053(8) -1.1165(4) 0.8984(3) 0.0613(13) Uani 1 1 d . . .
H6A H 0.932(3) -1.1245(5) 0.966(2) 0.12(2) Uiso 1 1 calc R . .
H6B H 0.943(2) -1.031(3) 0.8618(12) 0.16(3) Uiso 1 1 calc R . .
H6C H 1.118(4) -1.1134(4) 0.9111(6) 0.15(3) Uiso 1 1 calc R . .
C7 C 1.2447(6) -1.6653(4) 0.8427(3) 0.0495(10) Uani 1 1 d . . .
H7A H 1.2934(16) -1.6600(4) 0.908(2) 0.20(3) Uiso 1 1 calc R . .
H7B H 1.344(3) -1.7206(18) 0.7877(17) 0.13(2) Uiso 1 1 calc R . .
H7C H 1.154(3) -1.7116(15) 0.8607(6) 0.093(17) Uiso 1 1 calc R . .
C8 C 1.1249(5) -1.3911(4) 0.8681(3) 0.0415(8) Uani 1 1 d . . .
C9 C 0.6376(5) -0.5055(4) 0.7388(3) 0.0412(8) Uani 1 1 d . . .
C10 C 1.1035(5) -1.4999(4) 0.6885(3) 0.0367(8) Uani 1 1 d . . .
C11 C 1.0237(5) -1.3481(4) 0.6523(3) 0.0368(8) Uani 1 1 d . . .
C12 C 0.9955(5) -1.2273(4) 0.7189(3) 0.0387(8) Uani 1 1 d . . .
C13 C 0.5314(6) -0.2459(4) 0.8016(4) 0.0553(10) Uani 1 1 d . . .
H13 H 0.513(6) -0.182(5) 0.859(4) 0.065(12) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O2 1.350(4) . ?
B1 O1 1.365(5) . ?
B1 C9 1.570(5) . ?
Cl C4 1.749(4) . ?
O3 C10 1.231(4) . ?
O4 C8 1.231(4) . ?
N1 C2 1.342(4) . ?
N1 C12 1.354(4) . ?
N2 C2 1.322(5) . ?
N2 C11 1.377(4) . ?
N3 C8 1.366(4) . ?
N3 C12 1.381(4) . ?
N3 C6 1.468(4) . ?
N4 C8 1.392(4) . ?
N4 C10 1.409(4) . ?
N4 C7 1.471(4) . ?
C1 C3 1.367(5) . ?
C1 C4 1.383(5) . ?
C3 C9 1.402(5) . ?
C4 C13 1.379(5) . ?
C5 C13 1.374(5) . ?
C5 C9 1.402(5) . ?
C10 C11 1.412(4) . ?
C11 C12 1.372(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 B1 O1 118.7(3) . . ?
O2 B1 C9 117.5(3) . . ?
O1 B1 C9 123.8(3) . . ?
C2 N1 C12 102.3(3) . . ?
C2 N2 C11 106.7(3) . . ?
C8 N3 C12 119.4(3) . . ?
C8 N3 C6 120.4(3) . . ?
C12 N3 C6 120.3(3) . . ?
C8 N4 C10 125.9(3) . . ?
C8 N4 C7 117.4(3) . . ?
C10 N4 C7 116.7(3) . . ?
C3 C1 C4 118.3(3) . . ?
N2 C2 N1 114.0(3) . . ?
C1 C3 C9 123.2(3) . . ?
C13 C4 C1 121.2(3) . . ?
C13 C4 Cl 119.0(3) . . ?
C1 C4 Cl 119.7(3) . . ?
C13 C5 C9 121.9(3) . . ?
O4 C8 N3 121.5(3) . . ?
O4 C8 N4 120.4(3) . . ?
N3 C8 N4 118.1(3) . . ?
C3 C9 C5 116.0(3) . . ?
C3 C9 B1 120.6(3) . . ?
C5 C9 B1 123.4(3) . . ?
O3 C10 N4 120.3(3) . . ?
O3 C10 C11 127.5(3) . . ?
N4 C10 C11 112.2(3) . . ?
C12 C11 N2 104.5(3) . . ?
C12 C11 C10 123.1(3) . . ?
N2 C11 C10 132.4(3) . . ?
N1 C12 C11 112.5(3) . . ?
N1 C12 N3 126.2(3) . . ?
C11 C12 N3 121.3(3) . . ?
C5 C13 C4 119.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_ura
_database_code_depnum_ccdc_archive 'CCDC 1440007'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ' IPBA + Theophylline '
_chemical_melting_point          ?
_chemical_formula_moiety         ' C7 H8 N4 O2, C6 H6 B I O2 '
_chemical_formula_sum            'C13 H14 B I N4 O4'
_chemical_formula_weight         427.99

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ' Triclinic '
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.4750(1)
_cell_length_b                   9.623(2)
_cell_length_c                   11.957(3)
_cell_angle_alpha                87.25(1)
_cell_angle_beta                 80.94(1)
_cell_angle_gamma                71.63(1)
_cell_volume                     806.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3923
_cell_measurement_theta_min      1.72
_cell_measurement_theta_max      25.04

_exptl_crystal_description       ' Plates '
_exptl_crystal_colour            ' Colourless '
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    2.011
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.531
_exptl_absorpt_correction_T_max  0.642
_exptl_absorpt_process_details   'SADABS; Sheldrick, 96'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Brucker APEX-CCD Area Detector'
_diffrn_measurement_method       SMART
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3923
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2626
_reflns_number_gt                2379
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0925P)²+0.8555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2626
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.2586(11) 0.6969(8) 0.2417(6) 0.0401(16) Uani 1 1 d . . .
N1 N 1.0358(8) 0.2881(6) 0.4477(4) 0.0380(12) Uani 1 1 d . . .
N2 N 0.9679(8) 0.2419(5) 0.1710(4) 0.0365(12) Uani 1 1 d . . .
N3 N 1.0826(8) 0.0995(6) 0.3339(4) 0.0401(12) Uani 1 1 d . . .
N7 N 0.8532(7) 0.4970(5) 0.2026(4) 0.0352(12) Uani 1 1 d . . .
I1 I 0.62336(7) -0.00141(4) 0.30931(4) 0.0560(3) Uani 1 1 d . . .
O1 O 0.1952(9) 0.7587(6) 0.1458(5) 0.0520(14) Uani 1 1 d . . .
H3B H 0.197(11) 0.711(9) 0.105(6) 0.04(2) Uiso 1 1 d . . .
O2 O 0.2461(9) 0.7830(6) 0.3297(4) 0.0525(13) Uani 1 1 d . . .
H2A H 0.200(13) 0.864(11) 0.326(7) 0.06(3) Uiso 1 1 d . . .
O3 O 0.8424(8) 0.3965(5) 0.0353(4) 0.0487(12) Uani 1 1 d . . .
O4 O 0.8682(7) 0.6044(5) 0.3645(4) 0.0443(11) Uani 1 1 d . . .
C2 C 1.0119(13) 0.1159(7) 0.0976(6) 0.053(2) Uani 1 1 d . . .
H2D H 0.906(6) 0.1102(8) 0.0777(13) 0.08(3) Uiso 1 1 calc R . .
H2B H 1.066(3) 0.036(4) 0.1339(19) 0.12(4) Uiso 1 1 calc R . .
H2C H 1.090(4) 0.1255(9) 0.037(3) 0.08(3) Uiso 1 1 calc R . .
C3 C 0.7625(12) 0.6410(7) 0.1580(6) 0.0477(18) Uani 1 1 d . . .
H3A H 0.670(5) 0.681(2) 0.199(2) 0.09(3) Uiso 1 1 calc R . .
H3C H 0.7362(19) 0.6325(8) 0.098(3) 0.12(5) Uiso 1 1 calc R . .
H3D H 0.833(4) 0.687(3) 0.1523(7) 0.05(3) Uiso 1 1 calc R . .
C4 C 0.4581(11) 0.2763(7) 0.1849(6) 0.0466(16) Uani 1 1 d . . .
H4A H 0.4769 0.2119 0.1255 0.056 Uiso 1 1 calc R . .
C5 C 0.4832(10) 0.3188(7) 0.3762(6) 0.0460(16) Uani 1 1 d . . .
H18 H 0.5191 0.2838 0.4458 0.055 Uiso 1 1 calc R . .
C6 C 0.3783(11) 0.4274(7) 0.1701(6) 0.0458(16) Uani 1 1 d . . .
H6 H 0.336(9) 0.458(8) 0.097(6) 0.041(18) Uiso 1 1 d . . .
C7 C 0.5084(9) 0.2243(7) 0.2882(6) 0.0415(14) Uani 1 1 d . . .
C8 C 0.4031(10) 0.4676(7) 0.3587(5) 0.0420(15) Uani 1 1 d . . .
H8 H 0.3853 0.5313 0.4185 0.050 Uiso 1 1 calc R . .
C9 C 0.8984(9) 0.4910(7) 0.3119(5) 0.0348(13) Uani 1 1 d . . .
C10 C 0.3486(9) 0.5259(7) 0.2574(5) 0.0368(14) Uani 1 1 d . . .
C11 C 1.0975(11) 0.1416(7) 0.4346(6) 0.0442(15) Uani 1 1 d . . .
H11 H 1.144(9) 0.070(8) 0.489(5) 0.039(17) Uiso 1 1 d . . .
C12 C 0.9769(9) 0.3460(7) 0.3478(5) 0.0343(13) Uani 1 1 d . . .
C13 C 0.8866(9) 0.3788(6) 0.1307(5) 0.0367(13) Uani 1 1 d . . .
C14 C 1.0091(9) 0.2264(7) 0.2808(5) 0.0343(13) Uani 1 1 d . . .
H1A H 1.050(10) 0.344(8) 0.494(6) 0.037(18) 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
B1 O2 1.344(9) . ?
B1 O1 1.349(9) . ?
B1 C10 1.584(9) . ?
N1 C11 1.347(9) . ?
N1 C12 1.371(8) . ?
N1 H1A 0.83(7) . ?
N2 C13 1.365(8) . ?
N2 C14 1.385(8) . ?
N2 C2 1.452(8) . ?
N3 C11 1.320(8) . ?
N3 C14 1.345(8) . ?
N7 C13 1.394(7) . ?
N7 C9 1.395(7) . ?
N7 C3 1.454(8) . ?
I1 C7 2.088(6) . ?
O1 H3B 0.68(8) . ?
O2 H2A 0.75(10) . ?
O3 C13 1.227(7) . ?
O4 C9 1.226(8) . ?
C2 H2D 0.8779 . ?
C2 H2B 0.8779 . ?
C2 H2C 0.8779 . ?
C3 H3A 0.7822 . ?
C3 H3C 0.7822 . ?
C3 H3D 0.7822 . ?
C4 C7 1.373(10) . ?
C4 C6 1.402(9) . ?
C4 H4A 0.9300 . ?
C5 C7 1.375(10) . ?
C5 C8 1.386(9) . ?
C5 H18 0.9300 . ?
C6 C10 1.388(10) . ?
C6 H6 0.98(7) . ?
C8 C10 1.376(9) . ?
C8 H8 0.9300 . ?
C9 C12 1.407(9) . ?
C11 H11 0.95(7) . ?
C12 C14 1.370(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 B1 O1 119.3(6) . . ?
O2 B1 C10 117.1(6) . . ?
O1 B1 C10 123.6(6) . . ?
C11 N1 C12 106.5(5) . . ?
C11 N1 H1A 133(5) . . ?
C12 N1 H1A 118(5) . . ?
C13 N2 C14 119.2(5) . . ?
C13 N2 C2 119.4(5) . . ?
C14 N2 C2 121.4(5) . . ?
C11 N3 C14 103.5(5) . . ?
C13 N7 C9 126.7(5) . . ?
C13 N7 C3 116.1(5) . . ?
C9 N7 C3 117.2(5) . . ?
B1 O1 H3B 116(7) . . ?
B1 O2 H2A 120(7) . . ?
N2 C2 H2D 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2D C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2D C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N7 C3 H3A 109.5 . . ?
N7 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
N7 C3 H3D 109.5 . . ?
H3A C3 H3D 109.5 . . ?
H3C C3 H3D 109.5 . . ?
C7 C4 C6 119.3(6) . . ?
C7 C4 H4A 120.4 . . ?
C6 C4 H4A 120.4 . . ?
C7 C5 C8 118.5(6) . . ?
C7 C5 H18 120.8 . . ?
C8 C5 H18 120.8 . . ?
C10 C6 C4 121.5(6) . . ?
C10 C6 H6 123(4) . . ?
C4 C6 H6 116(4) . . ?
C4 C7 C5 120.7(6) . . ?
C4 C7 I1 118.7(5) . . ?
C5 C7 I1 120.6(5) . . ?
C10 C8 C5 123.4(6) . . ?
C10 C8 H8 118.3 . . ?
C5 C8 H8 118.3 . . ?
O4 C9 N7 120.0(6) . . ?
O4 C9 C12 128.0(5) . . ?
N7 C9 C12 112.0(5) . . ?
C8 C10 C6 116.6(6) . . ?
C8 C10 B1 121.4(6) . . ?
C6 C10 B1 122.0(6) . . ?
N3 C11 N1 113.2(6) . . ?
N3 C11 H11 120(4) . . ?
N1 C11 H11 127(4) . . ?
C14 C12 N1 104.4(5) . . ?
C14 C12 C9 123.2(5) . . ?
N1 C12 C9 132.4(6) . . ?
O3 C13 N2 121.0(5) . . ?
O3 C13 N7 121.4(5) . . ?
N2 C13 N7 117.5(5) . . ?
N3 C14 C12 112.5(5) . . ?
N3 C14 N2 126.3(5) . . ?
C12 C14 N2 121.2(6) . . ?

_diffrn_measured_fraction_theta_max 0.922
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.922
_refine_diff_density_max         1.625
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.171
####################################################################### 
# 
# 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_ura
_database_code_depnum_ccdc_archive 'CCDC 1440008'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ' HPBA + Theophylline '
_chemical_melting_point          ?
_chemical_formula_moiety         ' C7 H8 N4 O2, C6 H7 B O3 '

_chemical_formula_sum            ' C13 H15 B N4 O5 '
_chemical_formula_weight         318.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ' Monoclinic '
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   12.858(3)
_cell_length_b                   8.2154(17)
_cell_length_c                   14.199(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.030(4)
_cell_angle_gamma                90.00
_cell_volume                     1485.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7220
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      25.26

_exptl_crystal_description       ' Blocks '
_exptl_crystal_colour            ' Colourless '
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'SADABS; Sheldrick, 96'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Brucker APEX-CCD Area Detector'
_diffrn_measurement_method       SMART
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7220
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         25.26
_reflns_number_total             2698
_reflns_number_gt                2021
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2698
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.32946(17) -0.4347(3) 0.48498(16) 0.0449(5) Uani 1 1 d . . .
O4 O 0.43912(11) 0.19728(18) 0.56352(9) 0.0516(4) Uani 1 1 d . . .
O2 O 0.36761(11) -0.38616(18) 0.57580(11) 0.0523(4) Uani 1 1 d . . .
H2A H 0.342(2) -0.428(3) 0.622(2) 0.074(8) Uiso 1 1 d . . .
O3 O 0.14970(12) -0.12351(19) 0.48234(12) 0.0640(5) Uani 1 1 d . . .
O1 O 0.38084(13) -0.3809(2) 0.41374(11) 0.0638(5) Uani 1 1 d . . .
H1A H 0.443(3) -0.324(4) 0.442(2) 0.114(11) Uiso 1 1 d . . .
O5 O -0.03451(13) -0.8293(2) 0.37403(13) 0.0704(5) Uani 1 1 d . . .
H5A H -0.067(2) -0.844(4) 0.426(2) 0.098(10) Uiso 1 1 d . . .
N4 N 0.29604(12) 0.0331(2) 0.52244(11) 0.0439(4) Uani 1 1 d . . .
N3 N 0.46712(14) 0.1801(2) 0.35407(11) 0.0478(4) Uani 1 1 d . . .
H3A H 0.5226(19) 0.241(3) 0.3741(15) 0.058(7) Uiso 1 1 d . . .
N2 N 0.24250(13) -0.0548(2) 0.36437(11) 0.0483(5) Uani 1 1 d . . .
N1 N 0.35662(14) 0.0350(2) 0.25141(11) 0.0562(5) Uani 1 1 d . . .
C8 C 0.38221(14) 0.1232(2) 0.50133(13) 0.0397(5) Uani 1 1 d . . .
C11 C 0.32719(15) 0.0261(2) 0.33912(13) 0.0430(5) Uani 1 1 d . . .
C5 C 0.07560(17) -0.6842(3) 0.49725(16) 0.0541(6) Uani 1 1 d . . .
H5 H 0.0314(17) -0.715(3) 0.5471(16) 0.054(6) Uiso 1 1 d . . .
C10 C 0.44157(18) 0.1300(3) 0.26468(15) 0.0573(6) Uani 1 1 d . . .
H10 H 0.478(2) 0.168(3) 0.215(2) 0.083(8) Uiso 1 1 d . . .
C9 C 0.39325(14) 0.1129(2) 0.40425(13) 0.0403(5) Uani 1 1 d . . .
C7 C 0.22486(16) -0.0518(3) 0.45707(14) 0.0467(5) Uani 1 1 d . . .
C6 C 0.16439(16) -0.5900(3) 0.52331(15) 0.0503(5) Uani 1 1 d . . .
H6 H 0.1800(16) -0.554(3) 0.5896(16) 0.050(6) Uiso 1 1 d . . .
C4 C 0.05060(15) -0.7359(3) 0.40427(15) 0.0498(5) Uani 1 1 d . . .
C2 C 0.20223(16) -0.5972(3) 0.36518(15) 0.0517(5) Uani 1 1 d . . .
H2 H 0.2451(19) -0.572(3) 0.3187(18) 0.066(7) Uiso 1 1 d . . .
C3 C 0.11465(18) -0.6910(3) 0.33813(16) 0.0570(6) Uani 1 1 d . . .
H3 H 0.0957(19) -0.727(3) 0.2738(18) 0.069(7) Uiso 1 1 d . . .
C1 C 0.23038(15) -0.5431(2) 0.45837(13) 0.0435(5) Uani 1 1 d . . .
C13 C 0.27538(18) 0.0319(3) 0.62170(14) 0.0578(6) Uani 1 1 d . . .
H13A H 0.2147 -0.0338 0.6268 0.087 Uiso 1 1 calc R . .
H13B H 0.2629 0.1411 0.6414 0.087 Uiso 1 1 calc R . .
H13C H 0.3350 -0.0124 0.6617 0.087 Uiso 1 1 calc R . .
C12 C 0.1692(2) -0.1441(3) 0.29429(17) 0.0668(7) Uani 1 1 d . . .
H12A H 0.1152 -0.1926 0.3253 0.100 Uiso 1 1 calc R . .
H12B H 0.2065 -0.2278 0.2657 0.100 Uiso 1 1 calc R . .
H12C H 0.1380 -0.0704 0.2460 0.100 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.357(3) . ?
B1 O2 1.373(3) . ?
B1 C1 1.557(3) . ?
O4 C8 1.227(2) . ?
O3 C7 1.227(2) . ?
O5 C4 1.356(3) . ?
N4 C7 1.396(3) . ?
N4 C8 1.399(2) . ?
N4 C13 1.470(2) . ?
N3 C10 1.331(3) . ?
N3 C9 1.379(2) . ?
N2 C11 1.366(3) . ?
N2 C7 1.367(3) . ?
N2 C12 1.468(3) . ?
N1 C10 1.334(3) . ?
N1 C11 1.353(2) . ?
C8 C9 1.408(3) . ?
C11 C9 1.366(3) . ?
C5 C4 1.381(3) . ?
C5 C6 1.386(3) . ?
C6 C1 1.392(3) . ?
C4 C3 1.383(3) . ?
C2 C3 1.374(3) . ?
C2 C1 1.395(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
O1 B1 O2 117.27(19) . . ?
O1 B1 C1 118.19(19) . . ?
O2 B1 C1 124.52(18) . . ?
C7 N4 C8 125.95(16) . . ?
C7 N4 C13 116.40(16) . . ?
C8 N4 C13 117.61(16) . . ?
C10 N3 C9 105.83(18) . . ?
C11 N2 C7 119.32(16) . . ?
C11 N2 C12 121.68(18) . . ?
C7 N2 C12 118.99(18) . . ?
C10 N1 C11 103.31(17) . . ?
O4 C8 N4 121.25(16) . . ?
O4 C8 C9 127.06(17) . . ?
N4 C8 C9 111.69(16) . . ?
N1 C11 N2 127.13(18) . . ?
N1 C11 C9 111.56(18) . . ?
N2 C11 C9 121.31(17) . . ?
C4 C5 C6 120.0(2) . . ?
N3 C10 N1 113.81(19) . . ?
C11 C9 N3 105.49(17) . . ?
C11 C9 C8 123.76(17) . . ?
N3 C9 C8 130.75(17) . . ?
O3 C7 N2 121.08(18) . . ?
O3 C7 N4 121.02(18) . . ?
N2 C7 N4 117.89(17) . . ?
C5 C6 C1 122.2(2) . . ?
O5 C4 C5 123.1(2) . . ?
O5 C4 C3 117.8(2) . . ?
C5 C4 C3 119.1(2) . . ?
C3 C2 C1 122.5(2) . . ?
C2 C3 C4 120.1(2) . . ?
C6 C1 C2 116.03(19) . . ?
C6 C1 B1 123.47(18) . . ?
C2 C1 B1 120.50(18) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.26
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_URA
_database_code_depnum_ccdc_archive 'CCDC 1440009'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            '1,4-benezenediboronic acid+ theophylline'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H8 N4 O2), C6 H8 B2, O4, 0.5(O)'
_chemical_formula_sum            'C20 H24 B2 N8 O8.50'
_chemical_formula_weight         534.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.528(2)
_cell_length_b                   8.711(2)
_cell_length_c                   9.661(3)
_cell_angle_alpha                109.740(10)
_cell_angle_beta                 94.470(10)
_cell_angle_gamma                104.78
_cell_volume                     642.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6198
_cell_measurement_theta_min      2.277
_cell_measurement_theta_max      25.027

_exptl_crystal_description       Plates
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             278
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'SADABS; Sheldrick, 96'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Brucker APEX-CCD Area Detector'
_diffrn_measurement_method       SMART
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6198
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2268
_reflns_number_gt                1814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0671P)²+0.3055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2282
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.1770
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_restrained_S_all      1.209
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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
B1 B 0.1494(5) 0.0326(5) 0.3053(4) 0.0452(9) Uani 1 1 d . . . . .
O1 O 0.2218(3) -0.0789(3) 0.3312(3) 0.0614(8) Uani 1 1 d . . . . .
O1W O 0.082(3) 0.613(4) 0.515(3) 0.227(15) Uani 0.25 1 d . . P . .
O2 O 0.1422(4) 0.1686(3) 0.4214(3) 0.0631(8) Uani 1 1 d . . . . .
H2A H 0.193(6) 0.179(6) 0.501(6) 0.106(19) Uiso 1 1 d . . . . .
O3 O 0.2371(3) 0.6065(3) 0.1178(3) 0.0607(7) Uani 1 1 d . . . . .
O4 O 0.4817(3) 0.2151(3) 0.1694(3) 0.0587(7) Uani 1 1 d . . . . .
N1 N 0.4039(4) 0.0509(4) -0.1751(3) 0.0500(8) Uani 1 1 d . . . . .
H1B H 0.455(4) -0.025(5) -0.157(4) 0.068(12) Uiso 1 1 d . . . . .
N2 N 0.2760(4) 0.1648(4) -0.3049(3) 0.0524(8) Uani 1 1 d . . . . .
N3 N 0.3606(3) 0.4114(3) 0.1417(3) 0.0451(7) Uani 1 1 d . . . . .
N4 N 0.2493(3) 0.4009(3) -0.0943(3) 0.0460(7) Uani 1 1 d . . . . .
C1 C 0.3416(5) 0.0405(5) -0.3089(4) 0.0534(9) Uani 1 1 d . . . . .
H1 H 0.340(4) -0.050(4) -0.398(3) 0.043(9) Uiso 1 1 d . . . . .
C2 C 0.2986(4) 0.2576(4) -0.1574(4) 0.0425(8) Uani 1 1 d . . . . .
C3 C 0.3766(4) 0.1928(4) -0.0739(4) 0.0416(8) Uani 1 1 d . . . . .
C4 C 0.4119(4) 0.2653(4) 0.0856(4) 0.0424(8) Uani 1 1 d . . . . .
C5 C 0.2792(4) 0.4795(4) 0.0574(4) 0.0452(8) Uani 1 1 d . . . . .
C6 C 0.1614(5) 0.4651(6) -0.1886(5) 0.0641(11) Uani 1 1 d . . . . .
H6A H 0.064(3) 0.4695(6) -0.1605(9) 0.089(15) Uiso 1 1 calc R . . . .
H6B H 0.1440(8) 0.395(2) -0.284(3) 0.115(19) Uiso 1 1 calc R . . . .
H6C H 0.2222(16) 0.570(3) -0.1783(5) 0.19(3) Uiso 1 1 calc R . . . .
C7 C 0.3851(6) 0.4933(5) 0.3056(4) 0.0640(11) Uani 1 1 d . . . . .
H7A H 0.3854(6) 0.601(4) 0.3303(9) 0.113(18) Uiso 1 1 calc R . . . .
H7B H 0.480(3) 0.4902(5) 0.3458(14) 0.16(3) Uiso 1 1 calc R . . . .
H7C H 0.304(3) 0.4382(18) 0.3390(12) 0.22(4) Uiso 1 1 calc R . . . .
C8 C 0.0714(4) 0.0141(4) 0.1444(3) 0.0417(8) Uani 1 1 d . . . . .
C9 C -0.0091(4) 0.1292(4) 0.1261(4) 0.0471(8) Uani 1 1 d . . . . .
H9 H -0.007(3) 0.223(4) 0.221(3) 0.040(8) Uiso 1 1 d . . . . .
C10 C -0.0774(4) 0.1150(4) -0.0127(4) 0.0461(8) Uani 1 1 d . . . . .
H10 H -0.133(3) 0.189(3) -0.020(3) 0.027(7) Uiso 1 1 d . . . . .
H1A H 0.218(5) -0.162(5) 0.253(4) 0.064(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O2 1.347(4) . ?
B1 O1 1.355(4) . ?
B1 C8 1.581(5) . ?
O3 C5 1.222(4) . ?
O4 C4 1.224(4) . ?
N1 C1 1.323(5) . ?
N1 C3 1.380(4) . ?
N2 C1 1.331(4) . ?
N2 C2 1.349(4) . ?
N3 C5 1.394(4) . ?
N3 C4 1.400(4) . ?
N3 C7 1.473(5) . ?
N4 C5 1.363(4) . ?
N4 C2 1.378(4) . ?
N4 C6 1.468(4) . ?
C2 C3 1.352(4) . ?
C3 C4 1.427(5) . ?
C8 C10 1.400(4) 2 ?
C8 C9 1.400(4) . ?
C9 C10 1.372(5) . ?
C10 C8 1.400(4) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 B1 O1 119.3(3) . . ?
O2 B1 C8 116.9(3) . . ?
O1 B1 C8 123.8(3) . . ?
C1 N1 C3 106.0(3) . . ?
C1 N2 C2 103.4(3) . . ?
C5 N3 C4 126.2(3) . . ?
C5 N3 C7 117.2(3) . . ?
C4 N3 C7 116.5(3) . . ?
C5 N4 C2 119.0(3) . . ?
C5 N4 C6 120.3(3) . . ?
C2 N4 C6 120.6(3) . . ?
N1 C1 N2 113.5(3) . . ?
N2 C2 C3 111.8(3) . . ?
N2 C2 N4 126.0(3) . . ?
C3 C2 N4 122.2(3) . . ?
C2 C3 N1 105.3(3) . . ?
C2 C3 C4 122.8(3) . . ?
N1 C3 C4 131.8(3) . . ?
O4 C4 N3 121.1(3) . . ?
O4 C4 C3 127.1(3) . . ?
N3 C4 C3 111.8(3) . . ?
O3 C5 N4 121.0(3) . . ?
O3 C5 N3 121.0(3) . . ?
N4 C5 N3 118.0(3) . . ?
C10 C8 C9 115.8(3) 2 . ?
C10 C8 B1 123.4(3) 2 . ?
C9 C8 B1 120.9(3) . . ?
C10 C9 C8 121.6(3) . . ?
C9 C10 C8 122.7(3) . 2 ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046

