# 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_tb-23dhb-wat-1-1a
_database_code_depnum_ccdc_archive 'CCDC 1938121'
loop_
_audit_author_name
_audit_author_address
'Mateusz Goldyn'
;Adam Mickiewicz University, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_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        
'theobromine-2,3-dihydroxybenzoic acid monohydrate'
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H6 O4, H2 O'
_chemical_formula_sum            'C14 H16 N4 O7'
_chemical_formula_weight         352.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H16 N4 O7'
_chemical_oxdiff_usercomment     '130 K, all of sphere'
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'
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'

_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           9
_space_group_name_H-M_alt        Cc
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.2358(3)
_cell_length_b                   15.2794(2)
_cell_length_c                   7.8074(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.180(2)
_cell_angle_gamma                90
_cell_volume                     1516.39(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6522
_cell_measurement_temperature    132(2)
_cell_measurement_theta_max      75.5370
_cell_measurement_theta_min      4.4910
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.767
_exptl_absorpt_coefficient_mu    1.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_preparation       
'Stoichometric ratio of thebromine and 2,3-dihydroxybenzoic acid (1:1) was dissolved in methanol-water solution'
_exptl_crystal_recrystallization_method 
'cocrystallization from methanol-water mixture (v/v 1:1) by slow evaporation'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7869
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.883
_diffrn_reflns_theta_min         4.525
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      132(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -13.00   1.00    1.50    --  -41.24 -57.00  30.00  100
  2  ω    -69.00  32.00   1.00    1.50    --  -41.24  57.00-180.00  101
  3  ω    -66.00  33.00   1.00    1.50    --  -41.24  37.00 -30.00   99
  4  ω      2.00  97.00   1.00    1.50    --   41.24-125.00   0.00   95
  5  ω      2.00  97.00   1.00    1.50    --   41.24-125.00-120.00   95
  6  ω     39.00  77.00   1.00    4.75    --  112.00 -45.00-150.00   38
  7  ω     36.00 113.00   1.00    4.75    --  112.00-111.00 -90.00   77
  8  ω     36.00 145.00   1.00    4.75    --  112.00 -77.00  90.00  109
  9  ω     36.00 113.00   1.00    4.75    --  112.00-111.00  60.00   77
 10  ω     36.00  69.00   1.00    4.75    --  112.00 -30.00  60.00   33
 11  ω     29.00 110.00   1.00    4.75    --  112.00 -94.00  90.00   81
 12  ω     39.00  77.00   1.00    4.75    --  112.00 -45.00 120.00   38
 13  ω     36.00  69.00   1.00    4.75    --  112.00 -30.00  30.00   33
 14  ω     39.00  77.00   1.00    4.75    --  112.00 -45.00 -90.00   38
 15  ω     83.00 158.00   1.00    4.75    --  112.00  61.00 -60.00   75
 16  ω     36.00 113.00   1.00    4.75    --  112.00-111.00 -30.00   77
 17  ω     79.00 158.00   1.00    4.75    --  112.00 111.00-180.00   79
 18  ω     36.00  69.00   1.00    4.75    --  112.00 -30.00-120.00   33
 19  ω     36.00  69.00   1.00    4.75    --  112.00 -30.00 150.00   33
 20  ω     24.00 158.00   1.00    4.75    --  112.00   0.00   0.00  134
 21  ω     36.00 113.00   1.00    4.75    --  112.00-111.00  90.00   77
 22  ω     39.00  77.00   1.00    4.75    --  112.00 -45.00  90.00   38
 23  ω     83.00 158.00   1.00    4.75    --  112.00  61.00   0.00   75
 24  ω     72.00 112.00   1.00    4.75    --  112.00-111.00-120.00   40
 25  ω     70.00 113.00   1.00    4.75    --  112.00-111.00  30.00   43
 26  ω     37.00 107.00   1.00    4.75    --  112.00-111.00 -60.00   70
 27  ω     58.00  83.00   1.00    4.75    --  112.00-111.00   0.00   25
 28  ω     36.00  56.00   1.00    4.75    --  112.00 -30.00   0.00   20
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0455255000
_diffrn_orient_matrix_UB_12      0.0193768000
_diffrn_orient_matrix_UB_13      0.1574727000
_diffrn_orient_matrix_UB_21      -0.1067395000
_diffrn_orient_matrix_UB_22      -0.0382169000
_diffrn_orient_matrix_UB_23      -0.1066693000
_diffrn_orient_matrix_UB_31      0.0349734000
_diffrn_orient_matrix_UB_32      -0.0912248000
_diffrn_orient_matrix_UB_33      0.0778867000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.816
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                2834
_reflns_number_total             2847
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.197
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2847
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.064
_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)+(0.0499P)²+0.3660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0730
_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
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C6(H6), C4(H4a)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), 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
O6 O 0.28471(12) 0.41601(9) 1.07712(19) 0.0263(3) Uani 1 1 d . . . . .
O1 O 0.54557(14) 0.18723(10) 0.4212(2) 0.0293(3) Uani 1 1 d . . . . .
O5 O 0.30661(13) 0.12075(10) 1.1619(2) 0.0278(3) Uani 1 1 d . . . . .
O3 O 0.63027(13) 0.15495(10) 0.1696(2) 0.0265(3) Uani 1 1 d . . . . .
O7 O 0.67504(13) 0.04885(10) -0.1627(2) 0.0309(3) Uani 1 1 d . . . . .
O4 O 0.71516(14) 0.21868(11) -0.0814(2) 0.0288(3) Uani 1 1 d . . . . .
O2 O 0.51925(14) 0.32530(11) 0.4938(2) 0.0312(4) Uani 1 1 d . . . . .
N1 N 0.30336(15) 0.26877(11) 1.1188(2) 0.0223(3) Uani 1 1 d . . . . .
N3 N 0.42434(13) 0.11717(11) 0.8674(2) 0.0224(3) Uani 1 1 d . . . . .
N2 N 0.36971(13) 0.34032(10) 0.9079(2) 0.0212(3) Uani 1 1 d . . . . .
N4 N 0.44828(13) 0.24158(11) 0.7353(2) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.38337(16) 0.18363(13) 0.9475(3) 0.0207(4) Uani 1 1 d . . . . .
C8 C 0.33008(16) 0.18328(13) 1.0832(3) 0.0216(4) Uani 1 1 d . . . . .
C9 C 0.31768(16) 0.34576(12) 1.0363(3) 0.0213(4) Uani 1 1 d . . . . .
C2 C 0.63644(16) 0.24319(13) 0.1565(3) 0.0216(4) Uani 1 1 d . . . . .
C7 C 0.55275(16) 0.26689(14) 0.3994(3) 0.0242(4) Uani 1 1 d . . . . .
C5 C 0.66001(18) 0.42310(14) 0.1179(3) 0.0291(4) Uani 1 1 d . . . . .
H5 H 0.669323 0.482926 0.106389 0.035 Uiso 1 1 calc R . . . .
C12 C 0.46187(16) 0.15489(13) 0.7438(3) 0.0239(4) Uani 1 1 d . . . . .
H12 H 0.494204 0.124017 0.670931 0.029 Uiso 1 1 calc R . . . .
C6 C 0.61295(17) 0.39261(14) 0.2440(3) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.589522 0.431915 0.315455 0.032 Uiso 1 1 calc R . . . .
C10 C 0.39975(14) 0.25882(13) 0.8636(3) 0.0207(4) Uani 1 1 d . . . . .
C14 C 0.43547(19) 0.02535(13) 0.9222(3) 0.0289(4) Uani 1 1 d . . . . .
H14A H 0.493347 0.019386 1.027700 0.043 Uiso 1 1 calc GR . . . .
H14B H 0.448401 -0.009516 0.828244 0.043 Uiso 1 1 calc GR . . . .
H14C H 0.371953 0.005884 0.946782 0.043 Uiso 1 1 calc GR . . . .
C1 C 0.60065(16) 0.30224(14) 0.2637(3) 0.0232(4) Uani 1 1 d . . . . .
C4 C 0.69361(17) 0.36448(15) 0.0077(3) 0.0281(4) Uani 1 1 d . . . . .
H4A H 0.724025 0.385483 -0.078178 0.034 Uiso 1 1 calc R . . . .
C3 C 0.68175(16) 0.27503(13) 0.0260(3) 0.0242(4) Uani 1 1 d . . . . .
C13 C 0.39006(18) 0.41839(13) 0.8139(3) 0.0278(4) Uani 1 1 d . . . . .
H13A H 0.334368 0.425804 0.705803 0.042 Uiso 1 1 calc GR . . . .
H13B H 0.455742 0.411718 0.785661 0.042 Uiso 1 1 calc GR . . . .
H13C H 0.393398 0.468835 0.888573 0.042 Uiso 1 1 calc GR . . . .
H1 H 0.271(2) 0.2739(18) 1.201(4) 0.025(7) Uiso 1 1 d . . . . .
H7A H 0.711(3) 0.052(2) -0.242(5) 0.042(8) Uiso 1 1 d . . . . .
H2 H 0.489(5) 0.296(4) 0.589(8) 0.097(19) Uiso 1 1 d . . . . .
H7B H 0.704(3) 0.011(3) -0.094(5) 0.045(9) Uiso 1 1 d . . . . .
H4 H 0.695(2) 0.165(2) -0.076(4) 0.032(7) Uiso 1 1 d . . . . .
H3 H 0.599(3) 0.148(2) 0.252(6) 0.050(10) 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
O6 C9 1.234(2) . ?
O1 C7 1.236(3) . ?
O5 C8 1.222(3) . ?
O3 C2 1.356(3) . ?
O3 H3 0.87(5) . ?
O7 H7A 0.88(4) . ?
O7 H7B 0.81(4) . ?
O4 C3 1.359(3) . ?
O4 H4 0.87(3) . ?
O2 C7 1.311(3) . ?
O2 H2 1.03(6) . ?
N1 C8 1.401(3) . ?
N1 C9 1.380(3) . ?
N1 H1 0.87(3) . ?
N3 C11 1.381(3) . ?
N3 C12 1.333(3) . ?
N3 C14 1.462(2) . ?
N2 C9 1.367(3) . ?
N2 C10 1.380(2) . ?
N2 C13 1.464(2) . ?
N4 C12 1.336(3) . ?
N4 C10 1.358(3) . ?
C11 C8 1.427(3) . ?
C11 C10 1.370(3) . ?
C2 C1 1.400(3) . ?
C2 C3 1.405(3) . ?
C7 C1 1.480(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C5 C4 1.398(3) . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C6 C1 1.404(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C4 H4A 0.9300 . ?
C4 C3 1.388(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C2 O3 H3 103(3) . . ?
H7A O7 H7B 105(3) . . ?
C3 O4 H4 114(2) . . ?
C7 O2 H2 112(3) . . ?
C8 N1 H1 115.7(18) . . ?
C9 N1 C8 128.81(19) . . ?
C9 N1 H1 115.4(18) . . ?
C11 N3 C14 126.38(18) . . ?
C12 N3 C11 106.43(16) . . ?
C12 N3 C14 126.83(18) . . ?
C9 N2 C10 118.53(17) . . ?
C9 N2 C13 121.22(16) . . ?
C10 N2 C13 120.21(18) . . ?
C12 N4 C10 103.93(17) . . ?
N3 C11 C8 132.20(19) . . ?
C10 C11 N3 105.39(18) . . ?
C10 C11 C8 122.37(19) . . ?
O5 C8 N1 121.0(2) . . ?
O5 C8 C11 128.6(2) . . ?
N1 C8 C11 110.39(18) . . ?
O6 C9 N1 121.09(19) . . ?
O6 C9 N2 121.94(18) . . ?
N2 C9 N1 116.97(17) . . ?
O3 C2 C1 123.93(19) . . ?
O3 C2 C3 116.47(19) . . ?
C1 C2 C3 119.60(18) . . ?
O1 C7 O2 122.8(2) . . ?
O1 C7 C1 121.53(19) . . ?
O2 C7 C1 115.69(18) . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
N3 C12 N4 113.11(18) . . ?
N3 C12 H12 123.4 . . ?
N4 C12 H12 123.4 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C1 119.9(2) . . ?
C1 C6 H6 120.1 . . ?
N4 C10 N2 126.06(18) . . ?
N4 C10 C11 111.15(17) . . ?
C11 C10 N2 122.79(19) . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C1 C7 118.44(18) . . ?
C2 C1 C6 119.97(19) . . ?
C6 C1 C7 121.6(2) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4A 119.9 . . ?
O4 C3 C2 120.41(18) . . ?
O4 C3 C4 119.6(2) . . ?
C4 C3 C2 119.94(19) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
N1 H1 O4 0.87(3) 2.04(3) 2.898(2) 172(3) 4_456
O7 H7A O6 0.88(4) 1.99(4) 2.857(2) 168(3) 4_553
O2 H2 N4 1.03(6) 1.63(6) 2.657(3) 174(5) .
O7 H7B O6 0.81(4) 2.06(4) 2.867(2) 177(4) 3_544
O4 H4 O7 0.87(3) 1.89(3) 2.689(2) 152(3) .
O3 H3 O1 0.87(5) 1.76(5) 2.566(2) 153(4) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C1 C2 1.2(3) . . . . ?
O1 C7 C1 C6 -177.22(19) . . . . ?
O3 C2 C1 C7 -0.2(3) . . . . ?
O3 C2 C1 C6 178.23(18) . . . . ?
O3 C2 C3 O4 1.1(3) . . . . ?
O3 C2 C3 C4 -178.17(18) . . . . ?
O2 C7 C1 C2 -179.00(18) . . . . ?
O2 C7 C1 C6 2.6(3) . . . . ?
N3 C11 C8 O5 -0.8(4) . . . . ?
N3 C11 C8 N1 -179.8(2) . . . . ?
N3 C11 C10 N2 -179.60(17) . . . . ?
N3 C11 C10 N4 0.3(2) . . . . ?
C11 N3 C12 N4 -0.3(2) . . . . ?
C8 N1 C9 O6 176.2(2) . . . . ?
C8 N1 C9 N2 -3.8(3) . . . . ?
C8 C11 C10 N2 2.5(3) . . . . ?
C8 C11 C10 N4 -177.57(18) . . . . ?
C9 N1 C8 O5 -175.7(2) . . . . ?
C9 N1 C8 C11 3.4(3) . . . . ?
C9 N2 C10 N4 177.44(18) . . . . ?
C9 N2 C10 C11 -2.7(3) . . . . ?
C5 C6 C1 C2 0.3(3) . . . . ?
C5 C6 C1 C7 178.73(19) . . . . ?
C5 C4 C3 O4 -179.7(2) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C12 N3 C11 C8 177.6(2) . . . . ?
C12 N3 C11 C10 0.0(2) . . . . ?
C12 N4 C10 N2 179.40(18) . . . . ?
C12 N4 C10 C11 -0.5(2) . . . . ?
C6 C5 C4 C3 -1.2(3) . . . . ?
C10 N2 C9 O6 -176.91(18) . . . . ?
C10 N2 C9 N1 3.0(3) . . . . ?
C10 N4 C12 N3 0.5(2) . . . . ?
C10 C11 C8 O5 176.4(2) . . . . ?
C10 C11 C8 N1 -2.5(3) . . . . ?
C14 N3 C11 C8 -9.0(3) . . . . ?
C14 N3 C11 C10 173.41(19) . . . . ?
C14 N3 C12 N4 -173.70(19) . . . . ?
C1 C2 C3 O4 -178.78(18) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C3 C2 C1 C7 179.67(19) . . . . ?
C3 C2 C1 C6 -1.9(3) . . . . ?
C13 N2 C9 O6 0.8(3) . . . . ?
C13 N2 C9 N1 -179.25(18) . . . . ?
C13 N2 C10 N4 -0.3(3) . . . . ?
C13 N2 C10 C11 179.59(18) . . . . ?

_olex2_date_sample_data_collection 2019-03-27
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-23DHBA-WAT
_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 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.876
####################################################################### 
# 
# 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_tb-k34dhb-1-1-meoh-h20
_database_code_depnum_ccdc_archive 'CCDC 1938148'
loop_
_audit_author_name
_audit_author_address
'Mateusz Goldyn'
;Adam Mickiewicz University, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_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        'theobromine-3,4-dihydroxybenzoic acid'
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H6 O4'
_chemical_formula_sum            'C14 H14 N4 O6'
_chemical_formula_weight         334.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 N4 O6'
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'
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'

_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   26.7527(5)
_cell_length_b                   14.2120(2)
_cell_length_c                   7.2608(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2760.62(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3752
_cell_measurement_temperature    130.9(8)
_cell_measurement_theta_max      74.5510
_cell_measurement_theta_min      3.2740
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.714
_exptl_absorpt_coefficient_mu    1.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_preparation       
'theobromine and 3,4-dihydroxybenzoic acid in stoichometric ratio (1:1) was dissolved in methanol-water solution'
_exptl_crystal_recrystallization_method 
'cocrystallization by slow evaporation from methanol-water solution'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7196
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.438
_diffrn_reflns_theta_min         3.304
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.9(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -15.00   1.00   16.50    --  -41.36 -57.00  90.00   83
  2  ω    -94.00 -56.00   1.00   16.50    --  -41.36 125.00 -90.00   38
  3  ω    -10.00  63.00   1.00   16.50    --   41.36 -37.00 -90.00   73
  4  ω     38.00  64.00   1.00   64.00    --  112.00 -30.00  30.00   26
  5  ω     85.00 111.00   1.00   64.00    --  112.00  61.00 150.00   26
  6  ω     49.00 104.00   1.00   64.00    --  112.00-111.00 150.00   55
  7  ω     40.00  66.00   1.00   64.00    --  112.00 -45.00 -60.00   26
  8  ω     38.00  63.00   1.00   64.00    --  112.00 -30.00 -90.00   25
  9  ω     87.00 113.00   1.00   64.00    --  112.00-111.00  60.00   26
 10  ω     39.00  73.00   1.00   64.00    --  112.00 -45.00 120.00   34
 11  ω     45.00  75.00   1.00   64.00    --  112.00 -45.00  60.00   30
 12  ω    127.00 155.00   1.00   64.00    --  112.00  61.00 150.00   28
 13  ω     97.00 158.00   1.00   64.00    --  112.00  30.00-120.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0133710000
_diffrn_orient_matrix_UB_12      0.1054173000
_diffrn_orient_matrix_UB_13      -0.0054047000
_diffrn_orient_matrix_UB_21      -0.0068155000
_diffrn_orient_matrix_UB_22      0.0003170000
_diffrn_orient_matrix_UB_23      -0.2107003000
_diffrn_orient_matrix_UB_31      -0.0555728000
_diffrn_orient_matrix_UB_32      0.0253244000
_diffrn_orient_matrix_UB_33      0.0247605000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2530
_reflns_number_total             2827
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.254
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.094
_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)+(0.0664P)²+2.9797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1478
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O6 O 0.54129(6) 0.24306(11) 0.6087(2) 0.0278(4) Uani 1 1 d . . . . .
O2 O 0.37877(6) 0.49677(11) 0.2184(3) 0.0311(4) Uani 1 1 d . . . . .
O5 O 0.44395(6) 0.00651(11) 0.3819(2) 0.0307(4) Uani 1 1 d . . . . .
O1 O 0.30795(6) 0.44990(11) 0.0848(2) 0.0315(4) Uani 1 1 d . . . . .
O4 O 0.29063(6) 0.90015(11) 0.0927(2) 0.0311(4) Uani 1 1 d . . . . .
O3 O 0.37371(6) 0.84623(11) 0.2563(3) 0.0325(4) Uani 1 1 d . . . . .
N1 N 0.49068(7) 0.12824(13) 0.4955(3) 0.0259(4) Uani 1 1 d . . . . .
N2 N 0.47153(7) 0.28749(12) 0.4514(3) 0.0248(4) Uani 1 1 d . . . . .
N3 N 0.37618(7) 0.16268(12) 0.2247(3) 0.0243(4) Uani 1 1 d . . . . .
N4 N 0.39644(7) 0.31353(12) 0.2669(3) 0.0258(4) Uani 1 1 d . . . . .
C10 C 0.43035(8) 0.25811(15) 0.3538(3) 0.0238(4) Uani 1 1 d . . . . .
C11 C 0.41901(8) 0.16458(15) 0.3295(3) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.44991(8) 0.09166(15) 0.4003(3) 0.0248(5) Uani 1 1 d . . . . .
C9 C 0.50323(8) 0.22109(15) 0.5241(3) 0.0249(4) Uani 1 1 d . . . . .
C1 C 0.32302(8) 0.61476(15) 0.1236(3) 0.0255(5) Uani 1 1 d . . . . .
C6 C 0.28074(8) 0.64373(16) 0.0279(3) 0.0267(5) Uani 1 1 d . . . . .
C2 C 0.35447(8) 0.68243(16) 0.2033(3) 0.0259(5) Uani 1 1 d . . . . .
C4 C 0.30014(8) 0.80637(15) 0.0970(3) 0.0255(5) Uani 1 1 d . . . . .
C3 C 0.34383(8) 0.77744(15) 0.1877(3) 0.0249(4) Uani 1 1 d . . . . .
C5 C 0.26940(8) 0.73916(16) 0.0146(3) 0.0266(5) Uani 1 1 d . . . . .
C12 C 0.36433(8) 0.25266(15) 0.1920(3) 0.0262(5) Uani 1 1 d . . . . .
C7 C 0.33517(8) 0.51317(15) 0.1398(3) 0.0274(5) Uani 1 1 d . . . . .
C13 C 0.48080(10) 0.38722(16) 0.4886(4) 0.0312(5) Uani 1 1 d . . . . .
C14 C 0.34829(9) 0.07831(16) 0.1690(4) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.2369(7) 0.7645(13) -0.055(3) 0.000(4) Uiso 1 1 d . . . . .
H2A H 0.3840(10) 0.6637(17) 0.263(4) 0.021(6) Uiso 1 1 d . . . . .
H12 H 0.3356(9) 0.2696(16) 0.126(3) 0.014(5) Uiso 1 1 d . . . . .
H6 H 0.2596(11) 0.597(2) -0.033(4) 0.034(7) Uiso 1 1 d . . . . .
H4 H 0.2602(13) 0.910(2) 0.071(4) 0.043(9) Uiso 1 1 d . . . . .
H3 H 0.4032(14) 0.817(2) 0.302(5) 0.056(10) Uiso 1 1 d . . . . .
H1 H 0.5113(12) 0.088(2) 0.539(5) 0.044(9) Uiso 1 1 d . . . . .
H2 H 0.3842(13) 0.434(3) 0.234(5) 0.059(10) Uiso 1 1 d . . . . .
H13A H 0.5155(13) 0.400(2) 0.492(5) 0.048(9) Uiso 1 1 d . . . . .
H13B H 0.4669(13) 0.405(2) 0.609(5) 0.049(9) Uiso 1 1 d . . . . .
H14A H 0.3702(16) 0.031(3) 0.143(6) 0.076(13) Uiso 1 1 d . . . . .
H13C H 0.4663(14) 0.421(3) 0.393(5) 0.058(10) Uiso 1 1 d . . . . .
H14B H 0.3296(14) 0.091(3) 0.066(5) 0.059(10) Uiso 1 1 d . . . . .
H14C H 0.3268(17) 0.062(3) 0.265(7) 0.086(14) 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
O6 C9 1.229(3) . ?
O2 C7 1.319(3) . ?
O2 H2 0.90(4) . ?
O5 C8 1.228(3) . ?
O1 C7 1.224(3) . ?
O4 C4 1.357(3) . ?
O4 H4 0.84(3) . ?
O3 C3 1.357(3) . ?
O3 H3 0.95(4) . ?
N1 C8 1.392(3) . ?
N1 C9 1.377(3) . ?
N1 H1 0.85(3) . ?
N2 C10 1.375(3) . ?
N2 C9 1.374(3) . ?
N2 C13 1.464(3) . ?
N3 C11 1.376(3) . ?
N3 C12 1.339(3) . ?
N3 C14 1.469(3) . ?
N4 C10 1.357(3) . ?
N4 C12 1.335(3) . ?
C10 C11 1.375(3) . ?
C11 C8 1.422(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.403(3) . ?
C1 C7 1.484(3) . ?
C6 C5 1.393(3) . ?
C6 H6 0.98(3) . ?
C2 C3 1.385(3) . ?
C2 H2A 0.94(3) . ?
C4 C3 1.403(3) . ?
C4 C5 1.395(3) . ?
C5 H5 1.066(19) . ?
C12 H12 0.94(2) . ?
C13 H13A 0.95(4) . ?
C13 H13B 0.99(4) . ?
C13 H13C 0.93(4) . ?
C14 H14A 0.91(4) . ?
C14 H14B 0.91(4) . ?
C14 H14C 0.93(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H2 112(2) . . ?
C4 O4 H4 110(2) . . ?
C3 O3 H3 108(2) . . ?
C8 N1 H1 116(2) . . ?
C9 N1 C8 128.58(19) . . ?
C9 N1 H1 115(2) . . ?
C10 N2 C13 121.66(18) . . ?
C9 N2 C10 118.94(18) . . ?
C9 N2 C13 119.31(19) . . ?
C11 N3 C14 126.26(18) . . ?
C12 N3 C11 106.05(18) . . ?
C12 N3 C14 127.64(19) . . ?
C12 N4 C10 104.09(18) . . ?
N4 C10 N2 126.80(19) . . ?
N4 C10 C11 110.73(19) . . ?
C11 C10 N2 122.45(19) . . ?
N3 C11 C8 132.05(19) . . ?
C10 C11 N3 105.89(18) . . ?
C10 C11 C8 122.0(2) . . ?
O5 C8 N1 121.59(19) . . ?
O5 C8 C11 127.1(2) . . ?
N1 C8 C11 111.28(19) . . ?
O6 C9 N1 121.37(19) . . ?
O6 C9 N2 121.9(2) . . ?
N2 C9 N1 116.72(19) . . ?
C6 C1 C2 119.4(2) . . ?
C6 C1 C7 120.4(2) . . ?
C2 C1 C7 120.2(2) . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6 119.4(17) . . ?
C5 C6 H6 120.6(17) . . ?
C1 C2 H2A 120.0(15) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2A 119.1(15) . . ?
O4 C4 C3 117.03(19) . . ?
O4 C4 C5 123.5(2) . . ?
C5 C4 C3 119.4(2) . . ?
O3 C3 C2 123.5(2) . . ?
O3 C3 C4 116.85(19) . . ?
C2 C3 C4 119.7(2) . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 122.6(10) . . ?
C4 C5 H5 116.8(10) . . ?
N3 C12 H12 122.0(14) . . ?
N4 C12 N3 113.23(19) . . ?
N4 C12 H12 124.7(14) . . ?
O2 C7 C1 113.55(19) . . ?
O1 C7 O2 122.5(2) . . ?
O1 C7 C1 124.0(2) . . ?
N2 C13 H13A 111(2) . . ?
N2 C13 H13B 110(2) . . ?
N2 C13 H13C 107(2) . . ?
H13A C13 H13B 107(3) . . ?
H13A C13 H13C 109(3) . . ?
H13B C13 H13C 112(3) . . ?
N3 C14 H14A 110(3) . . ?
N3 C14 H14B 110(2) . . ?
N3 C14 H14C 108(3) . . ?
H14A C14 H14B 109(3) . . ?
H14A C14 H14C 112(4) . . ?
H14B C14 H14C 109(3) . . ?

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
O4 H4 O1 0.84(3) 1.91(4) 2.731(2) 164(3) 8_665
O3 H3 O6 0.95(4) 1.83(4) 2.783(2) 178(3) 5_666
N1 H1 O5 0.85(3) 1.89(4) 2.742(2) 175(3) 5_656
O2 H2 N4 0.90(4) 1.77(4) 2.670(2) 178(4) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C4 C3 O3 -2.7(3) . . . . ?
O4 C4 C3 C2 177.3(2) . . . . ?
O4 C4 C5 C6 -178.5(2) . . . . ?
N2 C10 C11 N3 -179.37(19) . . . . ?
N2 C10 C11 C8 -1.5(3) . . . . ?
N3 C11 C8 O5 -0.6(4) . . . . ?
N3 C11 C8 N1 178.2(2) . . . . ?
N4 C10 C11 N3 -0.5(3) . . . . ?
N4 C10 C11 C8 177.4(2) . . . . ?
C10 N2 C9 O6 178.2(2) . . . . ?
C10 N2 C9 N1 -1.0(3) . . . . ?
C10 N4 C12 N3 -0.6(3) . . . . ?
C10 C11 C8 O5 -177.7(2) . . . . ?
C10 C11 C8 N1 1.0(3) . . . . ?
C11 N3 C12 N4 0.4(3) . . . . ?
C8 N1 C9 O6 -178.6(2) . . . . ?
C8 N1 C9 N2 0.6(3) . . . . ?
C9 N1 C8 O5 178.2(2) . . . . ?
C9 N1 C8 C11 -0.6(3) . . . . ?
C9 N2 C10 N4 -177.2(2) . . . . ?
C9 N2 C10 C11 1.5(3) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C1 C2 C3 O3 -177.7(2) . . . . ?
C1 C2 C3 C4 2.3(3) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C1 C7 O2 173.7(2) . . . . ?
C6 C1 C7 O1 -5.7(4) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C2 C1 C7 O2 -5.6(3) . . . . ?
C2 C1 C7 O1 175.0(2) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C5 C4 C3 O3 176.4(2) . . . . ?
C5 C4 C3 C2 -3.6(3) . . . . ?
C12 N3 C11 C10 0.1(2) . . . . ?
C12 N3 C11 C8 -177.4(2) . . . . ?
C12 N4 C10 N2 179.5(2) . . . . ?
C12 N4 C10 C11 0.7(2) . . . . ?
C7 C1 C6 C5 179.5(2) . . . . ?
C7 C1 C2 C3 179.4(2) . . . . ?
C13 N2 C10 N4 6.4(3) . . . . ?
C13 N2 C10 C11 -174.9(2) . . . . ?
C13 N2 C9 O6 -5.3(3) . . . . ?
C13 N2 C9 N1 175.5(2) . . . . ?
C14 N3 C11 C10 -177.2(2) . . . . ?
C14 N3 C11 C8 5.2(4) . . . . ?
C14 N3 C12 N4 177.6(2) . . . . ?

_olex2_date_sample_data_collection 2019-02-23
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-34DHBA
_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 2.093
_oxdiff_exptl_absorpt_empirical_full_min 0.179
####################################################################### 
# 
# 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_tb-k35dhb-1-1-odp
_database_code_depnum_ccdc_archive 'CCDC 1938149'
loop_
_audit_author_name
_audit_author_address
'Mateusz Goldyn'
;Adam Mickiewicz University, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_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        'theobromine-3,5-dihydroxybenzoic acid'
_chemical_formula_moiety         'C7 H6 O4, C7 H8 N4 O2'
_chemical_formula_sum            'C14 H14 N4 O6'
_chemical_formula_weight         334.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H28 N8 O12'
_chemical_oxdiff_usercomment     '130 K, 0.12 x 0.12 x 0.14 [mm]'
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'
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'

_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 21/c'
_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                   14.4617(3)
_cell_length_b                   12.7978(3)
_cell_length_c                   15.7666(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.3554(17)
_cell_angle_gamma                90
_cell_volume                     2915.58(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6232
_cell_measurement_temperature    130.8(6)
_cell_measurement_theta_max      75.2160
_cell_measurement_theta_min      4.4450
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1392
_exptl_crystal_preparation       
'theobromine and 3,5-dihydroxybenzoic acid in stoichometri ratio was dissolved in water and next this mixture was heated and mixed for 30 minutes.'
_exptl_crystal_recrystallization_method 
'cocrystallization by slow evaporation from water solution'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16119
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.087
_diffrn_reflns_theta_min         3.058
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.8(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 -15.00   1.00    5.00    --  -41.24  57.00 150.00   54
  2  ω   -119.00  -1.00   1.00    5.00    --  -41.24 -19.00 -60.00  118
  3  ω     20.00  76.00   1.00    5.00    --   41.24-125.00-150.00   56
  4  ω     64.00  95.00   1.00   20.00    --  112.00  15.00  60.00   31
  5  ω     36.00  68.00   1.00   20.00    --  112.00 -30.00-120.00   32
  6  ω     43.00  69.00   1.00   20.00    --  112.00 -30.00  30.00   26
  7  ω     36.00  69.00   1.00   20.00    --  112.00 -30.00-150.00   33
  8  ω     40.00  67.00   1.00   20.00    --  112.00 -45.00 120.00   27
  9  ω     39.00  65.00   1.00   20.00    --  112.00 -45.00 -60.00   26
 10  ω     48.00  73.00   1.00   20.00    --  112.00 -45.00 150.00   25
 11  ω     45.00 106.00   1.00   20.00    --  112.00-111.00 -30.00   61
 12  ω     47.00  73.00   1.00   20.00    --  112.00 -61.00  90.00   26
 13  ω     86.00 131.00   1.00   20.00    --  112.00 -61.00  90.00   45
 14  ω     68.00  97.00   1.00   20.00    --  112.00  15.00 -60.00   29
 15  ω     39.00  65.00   1.00   20.00    --  112.00 -45.00  30.00   26
 16  ω     36.00  62.00   1.00   20.00    --  112.00 -30.00 -90.00   26
 17  ω    128.00 154.00   1.00   20.00    --  112.00  15.00 -60.00   26
 18  ω     36.00 109.00   1.00   20.00    --  112.00 -77.00   0.00   73
 19  ω    113.00 138.00   1.00   20.00    --  112.00 -77.00   0.00   25
 20  ω    112.00 157.00   1.00   20.00    --  112.00  15.00  60.00   45
 21  ω     93.00 145.00   1.00   20.00    --  112.00  30.00-150.00   52
 22  ω     38.00  67.00   1.00   20.00    --  112.00 -30.00 -30.00   29
 23  ω    106.00 132.00   1.00   20.00    --  112.00  45.00 120.00   26
 24  ω     53.00  78.00   1.00   20.00    --  112.00-111.00-120.00   25
 25  ω     46.00  71.00   1.00   20.00    --  112.00-111.00  90.00   25
 26  ω     39.00  72.00   1.00   20.00    --  112.00 -45.00-180.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0789307000
_diffrn_orient_matrix_UB_12      0.0721211000
_diffrn_orient_matrix_UB_13      0.0327199000
_diffrn_orient_matrix_UB_21      -0.0609086000
_diffrn_orient_matrix_UB_22      0.0386862000
_diffrn_orient_matrix_UB_23      0.0715493000
_diffrn_orient_matrix_UB_31      0.0377641000
_diffrn_orient_matrix_UB_32      -0.0882954000
_diffrn_orient_matrix_UB_33      0.0580644000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5330
_reflns_number_total             6048
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.318
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         6048
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0732P)²+0.9562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1354
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O2A O 0.67750(8) 0.40482(10) 0.65170(7) 0.0324(3) Uani 1 1 d . . . . .
H2A H 0.739(2) 0.410(2) 0.6401(17) 0.054(7) Uiso 1 1 d . . . . .
O1A O 0.73528(9) 0.39940(11) 0.78526(8) 0.0376(3) Uani 1 1 d . . . . .
O3A O 0.44869(9) 0.40082(11) 0.96030(7) 0.0368(3) Uani 1 1 d . . . . .
H3A H 0.503(3) 0.397(2) 0.996(2) 0.079(10) Uiso 1 1 d . . . . .
O4A O 0.33167(8) 0.40714(10) 0.67689(8) 0.0332(3) Uani 1 1 d . . . . .
H4A H 0.3476(17) 0.3955(18) 0.6294(17) 0.043(6) Uiso 1 1 d . . . . .
C1A C 0.57121(11) 0.40088(12) 0.76185(10) 0.0277(3) Uani 1 1 d . . . . .
C2A C 0.55646(11) 0.40132(13) 0.84844(10) 0.0296(3) Uani 1 1 d . . . . .
H2AA H 0.6104(16) 0.4010(17) 0.8884(15) 0.039(6) Uiso 1 1 d . . . . .
C3A C 0.46664(12) 0.40298(13) 0.87573(10) 0.0303(3) Uani 1 1 d . . . . .
C4A C 0.39158(11) 0.40595(13) 0.81751(10) 0.0291(3) Uani 1 1 d . . . . .
H4AA H 0.3255(16) 0.4077(17) 0.8369(14) 0.038(6) Uiso 1 1 d . . . . .
C5A C 0.40786(11) 0.40537(12) 0.73090(10) 0.0276(3) Uani 1 1 d . . . . .
C6A C 0.49766(11) 0.40265(12) 0.70226(9) 0.0273(3) Uani 1 1 d . . . . .
H6A H 0.5125(15) 0.4015(15) 0.6449(14) 0.030(5) Uiso 1 1 d . . . . .
C7A C 0.66902(11) 0.40071(13) 0.73457(10) 0.0289(3) Uani 1 1 d . . . . .
O2B O 0.65868(9) 0.34272(10) 0.19928(7) 0.0334(3) Uani 1 1 d . . . . .
H2B H 0.593(2) 0.345(2) 0.212(2) 0.074(9) Uiso 1 1 d . . . . .
O1B O 0.60251(9) 0.34873(11) 0.06495(8) 0.0366(3) Uani 1 1 d . . . . .
O3B O 0.89095(10) 0.39531(13) -0.10430(8) 0.0456(3) Uani 1 1 d . . . . .
H3B H 0.837(3) 0.392(3) -0.140(2) 0.090(11) Uiso 1 1 d . . . . .
O4B O 1.00476(9) 0.36268(12) 0.17820(8) 0.0413(3) Uani 1 1 d . . . . .
H4B H 0.9866(19) 0.3538(19) 0.2267(18) 0.052(7) Uiso 1 1 d . . . . .
C1B C 0.76584(12) 0.36024(13) 0.09109(10) 0.0299(3) Uani 1 1 d . . . . .
C2B C 0.78165(12) 0.37365(15) 0.00503(10) 0.0334(4) Uani 1 1 d . . . . .
H2BA H 0.7285(16) 0.3753(17) -0.0376(15) 0.039(6) Uiso 1 1 d . . . . .
C3B C 0.87163(13) 0.38373(15) -0.02061(10) 0.0348(4) Uani 1 1 d . . . . .
C4B C 0.94596(12) 0.38102(14) 0.03806(11) 0.0333(4) Uani 1 1 d . . . . .
H4BA H 1.0110(16) 0.3897(16) 0.0189(14) 0.036(5) Uiso 1 1 d . . . . .
C5B C 0.92933(12) 0.36675(14) 0.12390(10) 0.0325(3) Uani 1 1 d . . . . .
C6B C 0.83903(12) 0.35648(14) 0.15091(10) 0.0317(3) Uani 1 1 d . . . . .
H6B H 0.8258(15) 0.3462(16) 0.2107(14) 0.035(5) Uiso 1 1 d . . . . .
C7B C 0.66850(12) 0.34999(13) 0.11678(10) 0.0305(3) Uani 1 1 d . . . . .
O5A O 0.17411(8) 0.33693(11) 0.31540(7) 0.0349(3) Uani 1 1 d . . . . .
O6A O 0.40341(9) 0.36735(11) 0.52082(7) 0.0368(3) Uani 1 1 d . . . . .
N1A N 0.29245(10) 0.35011(12) 0.41555(8) 0.0298(3) Uani 1 1 d . . . . .
H1A H 0.2514(16) 0.3504(17) 0.4540(14) 0.034(5) Uiso 1 1 d . . . . .
N2A N 0.44978(10) 0.35625(11) 0.38536(8) 0.0286(3) Uani 1 1 d . . . . .
N3A N 0.33076(10) 0.34418(11) 0.18653(8) 0.0298(3) Uani 1 1 d . . . . .
N4A N 0.47826(10) 0.34685(11) 0.23420(8) 0.0289(3) Uani 1 1 d . . . . .
C8A C 0.25799(11) 0.34471(13) 0.33216(10) 0.0287(3) Uani 1 1 d . . . . .
C9A C 0.38335(12) 0.35870(13) 0.44464(10) 0.0297(3) Uani 1 1 d . . . . .
C10A C 0.42248(11) 0.35055(12) 0.30071(10) 0.0269(3) Uani 1 1 d . . . . .
C11A C 0.33079(11) 0.34813(13) 0.27392(10) 0.0282(3) Uani 1 1 d . . . . .
C12A C 0.41949(12) 0.34306(13) 0.16631(10) 0.0310(3) Uani 1 1 d . . . . .
H12A H 0.4407(15) 0.3357(16) 0.1077(14) 0.034(5) Uiso 1 1 d . . . . .
C13A C 0.54744(12) 0.36244(15) 0.41380(11) 0.0329(4) Uani 1 1 d . . . . .
C14A C 0.25016(13) 0.34356(17) 0.12756(11) 0.0372(4) Uani 1 1 d . . . . .
O5B O 1.15864(8) 0.36044(10) 0.53734(7) 0.0339(3) Uani 1 1 d . . . . .
O6B O 0.92707(9) 0.34912(12) 0.33321(8) 0.0410(3) Uani 1 1 d . . . . .
N1B N 1.03903(10) 0.35154(12) 0.43805(8) 0.0308(3) Uani 1 1 d . . . . .
H1B H 1.0826(19) 0.3442(19) 0.4006(17) 0.050(7) Uiso 1 1 d . . . . .
N2B N 0.88309(10) 0.37791(12) 0.46793(9) 0.0321(3) Uani 1 1 d . . . . .
N3B N 1.00539(10) 0.40175(12) 0.66447(9) 0.0320(3) Uani 1 1 d . . . . .
N4B N 0.85794(10) 0.41310(12) 0.61703(9) 0.0341(3) Uani 1 1 d . . . . .
C8B C 1.07462(12) 0.36433(13) 0.52057(10) 0.0293(3) Uani 1 1 d . . . . .
C9B C 0.94790(12) 0.35860(14) 0.40876(10) 0.0319(3) Uani 1 1 d . . . . .
C10B C 0.91184(11) 0.39060(13) 0.55134(10) 0.0295(3) Uani 1 1 d . . . . .
C11B C 1.00356(11) 0.38327(13) 0.57805(10) 0.0293(3) Uani 1 1 d . . . . .
C12B C 0.91776(13) 0.41879(15) 0.68422(11) 0.0351(4) Uani 1 1 d . . . . .
H12B H 0.9013(16) 0.4336(17) 0.7383(15) 0.037(5) Uiso 1 1 d . . . . .
C13B C 0.78511(12) 0.38620(17) 0.44072(12) 0.0380(4) Uani 1 1 d . . . . .
C14B C 1.08549(13) 0.39592(17) 0.72434(11) 0.0372(4) Uani 1 1 d . . . . .
H14D H 1.1056(18) 0.324(2) 0.7278(16) 0.053(7) Uiso 1 1 d . . . . .
H14E H 1.0608(19) 0.417(2) 0.7782(18) 0.059(7) Uiso 1 1 d . . . . .
H14A H 0.273(2) 0.355(2) 0.0712(19) 0.062(8) Uiso 1 1 d . . . . .
H14B H 0.206(2) 0.395(2) 0.1452(18) 0.060(8) Uiso 1 1 d . . . . .
H13A H 0.560(2) 0.425(2) 0.4408(18) 0.061(8) Uiso 1 1 d . . . . .
H14F H 1.1361(19) 0.436(2) 0.7030(16) 0.055(7) Uiso 1 1 d . . . . .
H13D H 0.748(2) 0.365(2) 0.486(2) 0.072(9) Uiso 1 1 d . . . . .
H13B H 0.583(2) 0.356(2) 0.365(2) 0.070(9) Uiso 1 1 d . . . . .
H14C H 0.217(2) 0.275(2) 0.1280(18) 0.069(8) Uiso 1 1 d . . . . .
H13C H 0.559(2) 0.309(2) 0.4552(19) 0.068(8) Uiso 1 1 d . . . . .
H13E H 0.776(2) 0.344(3) 0.392(2) 0.081(10) Uiso 1 1 d . . . . .
H13F H 0.771(2) 0.455(3) 0.423(2) 0.088(10) 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
O2A C7A 1.3184(19) . ?
O1A C7A 1.222(2) . ?
O3A C3A 1.3693(19) . ?
O4A C5A 1.3648(19) . ?
C1A C2A 1.390(2) . ?
C1A C6A 1.390(2) . ?
C1A C7A 1.495(2) . ?
C2A C3A 1.385(2) . ?
C3A C4A 1.393(2) . ?
C4A C5A 1.395(2) . ?
C5A C6A 1.393(2) . ?
O2B C7B 1.318(2) . ?
O1B C7B 1.231(2) . ?
O3B C3B 1.368(2) . ?
O4B C5B 1.360(2) . ?
C1B C2B 1.396(2) . ?
C1B C6B 1.389(2) . ?
C1B C7B 1.487(2) . ?
C2B C3B 1.384(3) . ?
C3B C4B 1.389(2) . ?
C4B C5B 1.396(2) . ?
C5B C6B 1.396(2) . ?
O5A C8A 1.235(2) . ?
O6A C9A 1.229(2) . ?
N1A C8A 1.389(2) . ?
N1A C9A 1.379(2) . ?
N2A C9A 1.368(2) . ?
N2A C10A 1.378(2) . ?
N2A C13A 1.466(2) . ?
N3A C11A 1.3787(19) . ?
N3A C12A 1.335(2) . ?
N3A C14A 1.461(2) . ?
N4A C10A 1.350(2) . ?
N4A C12A 1.340(2) . ?
C8A C11A 1.426(2) . ?
C10A C11A 1.375(2) . ?
O5B C8B 1.234(2) . ?
O6B C9B 1.223(2) . ?
N1B C8B 1.389(2) . ?
N1B C9B 1.381(2) . ?
N2B C9B 1.372(2) . ?
N2B C10B 1.373(2) . ?
N2B C13B 1.467(2) . ?
N3B C11B 1.382(2) . ?
N3B C12B 1.335(2) . ?
N3B C14B 1.466(2) . ?
N4B C10B 1.353(2) . ?
N4B C12B 1.342(2) . ?
C8B C11B 1.419(2) . ?
C10B C11B 1.378(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
C2A C1A C7A 117.88(14) . . ?
C6A C1A C2A 121.30(15) . . ?
C6A C1A C7A 120.81(14) . . ?
C3A C2A C1A 119.25(15) . . ?
O3A C3A C2A 121.33(15) . . ?
O3A C3A C4A 117.93(15) . . ?
C2A C3A C4A 120.74(15) . . ?
C3A C4A C5A 119.11(15) . . ?
O4A C5A C4A 116.50(14) . . ?
O4A C5A C6A 122.54(14) . . ?
C6A C5A C4A 120.96(15) . . ?
C1A C6A C5A 118.62(14) . . ?
O2A C7A C1A 114.37(14) . . ?
O1A C7A O2A 123.10(15) . . ?
O1A C7A C1A 122.51(15) . . ?
C2B C1B C7B 118.07(15) . . ?
C6B C1B C2B 120.89(16) . . ?
C6B C1B C7B 121.03(15) . . ?
C3B C2B C1B 119.26(16) . . ?
O3B C3B C2B 121.56(16) . . ?
O3B C3B C4B 117.50(16) . . ?
C2B C3B C4B 120.94(16) . . ?
C3B C4B C5B 119.29(16) . . ?
O4B C5B C4B 116.72(16) . . ?
O4B C5B C6B 122.72(15) . . ?
C4B C5B C6B 120.56(16) . . ?
C1B C6B C5B 119.06(15) . . ?
O2B C7B C1B 114.64(14) . . ?
O1B C7B O2B 122.86(16) . . ?
O1B C7B C1B 122.50(15) . . ?
C9A N1A C8A 128.26(14) . . ?
C9A N2A C10A 118.79(14) . . ?
C9A N2A C13A 118.99(14) . . ?
C10A N2A C13A 122.21(14) . . ?
C11A N3A C14A 127.14(14) . . ?
C12A N3A C11A 106.16(13) . . ?
C12A N3A C14A 126.69(14) . . ?
C12A N4A C10A 104.01(14) . . ?
O5A C8A N1A 121.19(14) . . ?
O5A C8A C11A 127.56(15) . . ?
N1A C8A C11A 111.25(14) . . ?
O6A C9A N1A 121.05(15) . . ?
O6A C9A N2A 121.71(16) . . ?
N2A C9A N1A 117.24(14) . . ?
N4A C10A N2A 126.69(15) . . ?
N4A C10A C11A 111.11(14) . . ?
C11A C10A N2A 122.20(14) . . ?
N3A C11A C8A 132.26(15) . . ?
C10A C11A N3A 105.57(14) . . ?
C10A C11A C8A 122.08(14) . . ?
N3A C12A N4A 113.15(14) . . ?
C9B N1B C8B 128.11(14) . . ?
C9B N2B C10B 118.97(14) . . ?
C9B N2B C13B 119.52(14) . . ?
C10B N2B C13B 121.49(14) . . ?
C11B N3B C14B 127.51(14) . . ?
C12B N3B C11B 106.13(14) . . ?
C12B N3B C14B 126.20(14) . . ?
C12B N4B C10B 104.06(14) . . ?
O5B C8B N1B 121.31(15) . . ?
O5B C8B C11B 127.07(15) . . ?
N1B C8B C11B 111.61(14) . . ?
O6B C9B N1B 120.84(15) . . ?
O6B C9B N2B 122.18(16) . . ?
N2B C9B N1B 116.97(14) . . ?
N2B C10B C11B 122.31(15) . . ?
N4B C10B N2B 126.69(15) . . ?
N4B C10B C11B 110.99(15) . . ?
N3B C11B C8B 132.37(15) . . ?
C10B C11B N3B 105.59(14) . . ?
C10B C11B C8B 121.99(15) . . ?
N3B C12B N4B 113.22(15) . . ?

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
O2A H2A N4B 0.91(3) 1.78(3) 2.6901(19) 178(2) .
O3A H3A O1B 0.95(4) 1.87(4) 2.7953(18) 164(3) 1_556
O4A H4A O6A 0.81(3) 1.96(3) 2.7569(17) 172(3) .
O2B H2B N4A 0.98(3) 1.71(3) 2.6891(18) 178(3) .
O3B H3B O1A 0.95(4) 1.85(4) 2.7893(19) 173(3) 1_554
O4B H4B O6B 0.83(3) 1.92(3) 2.7370(19) 170(3) .
N1A H1A O5B 0.87(2) 1.92(2) 2.7848(18) 176(2) 1_455
N1B H1B O5A 0.89(3) 1.93(3) 2.8110(18) 176(2) 1_655

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
O3A C3A C4A C5A -178.30(15) . . . . ?
O4A C5A C6A C1A -179.93(14) . . . . ?
C1A C2A C3A O3A 178.33(15) . . . . ?
C1A C2A C3A C4A -1.1(3) . . . . ?
C2A C1A C6A C5A 0.3(2) . . . . ?
C2A C1A C7A O2A -177.23(14) . . . . ?
C2A C1A C7A O1A 1.1(2) . . . . ?
C2A C3A C4A C5A 1.1(2) . . . . ?
C3A C4A C5A O4A 179.26(14) . . . . ?
C3A C4A C5A C6A -0.5(2) . . . . ?
C4A C5A C6A C1A -0.2(2) . . . . ?
C6A C1A C2A C3A 0.4(2) . . . . ?
C6A C1A C7A O2A 1.5(2) . . . . ?
C6A C1A C7A O1A 179.84(16) . . . . ?
C7A C1A C2A C3A 179.10(15) . . . . ?
C7A C1A C6A C5A -178.42(15) . . . . ?
O3B C3B C4B C5B -178.45(17) . . . . ?
O4B C5B C6B C1B -179.18(16) . . . . ?
C1B C2B C3B O3B 178.91(17) . . . . ?
C1B C2B C3B C4B -0.2(3) . . . . ?
C2B C1B C6B C5B 0.2(3) . . . . ?
C2B C1B C7B O2B -176.82(15) . . . . ?
C2B C1B C7B O1B 3.0(3) . . . . ?
C2B C3B C4B C5B 0.7(3) . . . . ?
C3B C4B C5B O4B 178.74(16) . . . . ?
C3B C4B C5B C6B -0.7(3) . . . . ?
C4B C5B C6B C1B 0.3(3) . . . . ?
C6B C1B C2B C3B -0.3(3) . . . . ?
C6B C1B C7B O2B 3.2(2) . . . . ?
C6B C1B C7B O1B -176.96(16) . . . . ?
C7B C1B C2B C3B 179.80(16) . . . . ?
C7B C1B C6B C5B -179.82(16) . . . . ?
O5A C8A C11A N3A 0.0(3) . . . . ?
O5A C8A C11A C10A -175.93(17) . . . . ?
N1A C8A C11A N3A 179.30(17) . . . . ?
N1A C8A C11A C10A 3.3(2) . . . . ?
N2A C10A C11A N3A 179.05(14) . . . . ?
N2A C10A C11A C8A -4.0(2) . . . . ?
N4A C10A C11A N3A -0.84(18) . . . . ?
N4A C10A C11A C8A 176.07(15) . . . . ?
C8A N1A C9A O6A 176.74(16) . . . . ?
C8A N1A C9A N2A -3.8(3) . . . . ?
C9A N1A C8A O5A 179.89(17) . . . . ?
C9A N1A C8A C11A 0.6(2) . . . . ?
C9A N2A C10A N4A -179.58(16) . . . . ?
C9A N2A C10A C11A 0.5(2) . . . . ?
C10A N2A C9A O6A -177.47(15) . . . . ?
C10A N2A C9A N1A 3.1(2) . . . . ?
C10A N4A C12A N3A 0.00(19) . . . . ?
C11A N3A C12A N4A -0.5(2) . . . . ?
C12A N3A C11A C8A -175.67(18) . . . . ?
C12A N3A C11A C10A 0.79(18) . . . . ?
C12A N4A C10A N2A -179.36(16) . . . . ?
C12A N4A C10A C11A 0.53(18) . . . . ?
C13A N2A C9A O6A 1.0(2) . . . . ?
C13A N2A C9A N1A -178.45(15) . . . . ?
C13A N2A C10A N4A 2.0(2) . . . . ?
C13A N2A C10A C11A -177.86(15) . . . . ?
C14A N3A C11A C8A 5.5(3) . . . . ?
C14A N3A C11A C10A -178.05(16) . . . . ?
C14A N3A C12A N4A 178.33(16) . . . . ?
O5B C8B C11B N3B -0.2(3) . . . . ?
O5B C8B C11B C10B 176.96(17) . . . . ?
N1B C8B C11B N3B -179.03(17) . . . . ?
N1B C8B C11B C10B -1.9(2) . . . . ?
N2B C10B C11B N3B 179.20(15) . . . . ?
N2B C10B C11B C8B 1.4(3) . . . . ?
N4B C10B C11B N3B 0.3(2) . . . . ?
N4B C10B C11B C8B -177.49(16) . . . . ?
C8B N1B C9B O6B 177.29(17) . . . . ?
C8B N1B C9B N2B -1.9(3) . . . . ?
C9B N1B C8B O5B -176.68(17) . . . . ?
C9B N1B C8B C11B 2.2(2) . . . . ?
C9B N2B C10B N4B 177.84(17) . . . . ?
C9B N2B C10B C11B -0.9(3) . . . . ?
C10B N2B C9B O6B -178.16(17) . . . . ?
C10B N2B C9B N1B 1.0(2) . . . . ?
C10B N4B C12B N3B 0.3(2) . . . . ?
C11B N3B C12B N4B -0.1(2) . . . . ?
C12B N3B C11B C8B 177.35(19) . . . . ?
C12B N3B C11B C10B -0.13(19) . . . . ?
C12B N4B C10B N2B -179.19(17) . . . . ?
C12B N4B C10B C11B -0.4(2) . . . . ?
C13B N2B C9B O6B 0.9(3) . . . . ?
C13B N2B C9B N1B -179.96(16) . . . . ?
C13B N2B C10B N4B -1.2(3) . . . . ?
C13B N2B C10B C11B -179.88(17) . . . . ?
C14B N3B C11B C8B -7.1(3) . . . . ?
C14B N3B C11B C10B 175.46(17) . . . . ?
C14B N3B C12B N4B -175.76(17) . . . . ?

_olex2_date_sample_data_collection 2019-01-26
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-35DHBA
_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 1.453
_oxdiff_exptl_absorpt_empirical_full_min 0.798
####################################################################### 
# 
# 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_tb-k26dhb-1-1b-odp
_database_code_depnum_ccdc_archive 'CCDC 1938146'
loop_
_audit_author_name
_audit_author_address
'Mateusz Goldyn'
;Adam Mickiewicz University, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_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            
'theobromine 2,6-dihydroxybenzoic acid monohydrate'
_chemical_name_systematic        
'theobrominium 2,6-dihydroxybenzoate monohydrate'
_chemical_formula_moiety         'C7 H9 N4 O2, C7 H5 O4, H2 O'
_chemical_formula_sum            'C14 H16 N4 O7'
_chemical_formula_weight         352.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 N4 O6'
_chemical_oxdiff_usercomment     '131.6 K, 0.05 x 0.12 x 0.30'
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'
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'

_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 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.2976(3)
_cell_length_b                   6.84500(10)
_cell_length_c                   15.9300(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.911(3)
_cell_angle_gamma                90
_cell_volume                     1500.38(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4704
_cell_measurement_temperature    131.8(3)
_cell_measurement_theta_max      76.0290
_cell_measurement_theta_min      3.3430
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_preparation       
'stoichometric ratio of thebromine and 2,6-dihydroxybenzoic acid (1:1) was dissolved in acetonitrile-water solution'
_exptl_crystal_recrystallization_method 
'cocrystallization by slow evaporation from acetonitrile-water solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6426
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.312
_diffrn_reflns_theta_min         3.342
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      131.8(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    2.00    --  -41.36 125.00-120.00   81
  2  ω      9.00 109.00   1.00    2.00    --   41.36  77.00 150.00  100
  3  ω     11.00  66.00   1.00    2.00    --   41.36 -37.00   0.00   55
  4  ω     31.00  57.00   1.00    5.50    --  112.00 -94.00 150.00   26
  5  ω     36.00  65.00   1.00    5.50    --  112.00 -30.00 -60.00   29
  6  ω     41.00  77.00   1.00    5.50    --  112.00 -45.00 150.00   36
  7  ω     36.00  69.00   1.00    5.50    --  112.00 -30.00 -30.00   33
  8  ω     40.00  72.00   1.00    5.50    --  112.00 -45.00-150.00   32
  9  ω     37.00  65.00   1.00    5.50    --  112.00 -30.00  30.00   28
 10  ω     67.00  96.00   1.00    5.50    --  112.00-111.00 -90.00   29
 11  ω     53.00 107.00   1.00    5.50    --  112.00-111.00 120.00   54
 12  ω     40.00  66.00   1.00    5.50    --  112.00 -30.00   0.00   26
 13  ω     39.00  65.00   1.00    5.50    --  112.00 -30.00 -90.00   26
 14  ω     53.00 105.00   1.00    5.50    --  112.00-111.00 -30.00   52
 15  ω     47.00  73.00   1.00    5.50    --  112.00 -45.00 120.00   26
 16  ω     42.00 113.00   1.00    5.50    --  112.00-111.00-180.00   71
 17  ω     59.00 157.00   1.00    5.50    --  112.00  15.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0163983000
_diffrn_orient_matrix_UB_12      0.2226759000
_diffrn_orient_matrix_UB_13      0.0073448000
_diffrn_orient_matrix_UB_21      0.0105379000
_diffrn_orient_matrix_UB_22      -0.0019951000
_diffrn_orient_matrix_UB_23      -0.0918692000
_diffrn_orient_matrix_UB_31      -0.1101877000
_diffrn_orient_matrix_UB_32      0.0331139000
_diffrn_orient_matrix_UB_33      -0.0554566000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2766
_reflns_number_total             3062
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.249
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.075
_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)+(0.0591P)²+0.4660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1051
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O5 O 0.20213(7) 0.51116(15) 0.60112(7) 0.0228(2) Uani 1 1 d . . . . .
O4 O 0.59261(7) 0.87320(16) 0.30377(7) 0.0259(2) Uani 1 1 d . . . . .
O6 O 0.12547(7) 0.57452(16) 0.29194(7) 0.0258(2) Uani 1 1 d . . . . .
O2 O 0.54756(7) 0.80061(16) 0.43689(7) 0.0242(2) Uani 1 1 d . . . . .
O3 O 0.83141(7) 0.93069(17) 0.62415(7) 0.0283(2) Uani 1 1 d . . . . .
O1 O 0.65891(7) 0.81568(17) 0.58435(7) 0.0275(2) Uani 1 1 d . . . . .
N1 N 0.16874(8) 0.54115(17) 0.44724(8) 0.0201(2) Uani 1 1 d . . . . .
N4 N 0.44182(8) 0.71235(17) 0.51947(7) 0.0197(2) Uani 1 1 d . . . . .
N3 N 0.41007(8) 0.64502(17) 0.63822(7) 0.0191(2) Uani 1 1 d . . . . .
N2 N 0.28228(8) 0.64496(17) 0.39362(7) 0.0194(2) Uani 1 1 d . . . . .
O7 O -0.02286(8) 0.4482(2) 0.38925(8) 0.0445(4) Uani 1 1 d . . . . .
C10 C 0.34732(9) 0.65351(19) 0.48488(9) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.18799(9) 0.58587(19) 0.37206(9) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.68379(9) 0.9146(2) 0.37030(9) 0.0200(3) Uani 1 1 d . . . . .
C12 C 0.47739(9) 0.7064(2) 0.61300(9) 0.0209(3) Uani 1 1 d . . . . .
C11 C 0.32598(9) 0.60925(19) 0.55747(9) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.63496(10) 0.8340(2) 0.49910(9) 0.0204(3) Uani 1 1 d . . . . .
C1 C 0.70743(9) 0.89714(19) 0.46606(9) 0.0191(3) Uani 1 1 d . . . . .
C8 C 0.22990(9) 0.55001(19) 0.54192(9) 0.0185(3) Uani 1 1 d . . . . .
C14 C 0.42350(10) 0.6207(2) 0.73479(9) 0.0244(3) Uani 1 1 d . . . . .
C3 C 0.87157(10) 1.0049(2) 0.50098(10) 0.0250(3) Uani 1 1 d . . . . .
C2 C 0.80363(10) 0.9431(2) 0.53135(9) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.75191(10) 0.9754(2) 0.34014(10) 0.0238(3) Uani 1 1 d . . . . .
C13 C 0.30964(10) 0.6989(2) 0.31927(9) 0.0255(3) Uani 1 1 d . . . . .
C4 C 0.84518(10) 1.0211(2) 0.40669(10) 0.0257(3) Uani 1 1 d . . . . .
H12 H 0.5408(14) 0.747(3) 0.6551(13) 0.028(4) Uiso 1 1 d . . . . .
H3A H 0.9378(15) 1.037(3) 0.5481(14) 0.034(5) Uiso 1 1 d . . . . .
H5 H 0.7334(13) 0.983(3) 0.2707(13) 0.026(4) Uiso 1 1 d . . . . .
H4B H 0.8915(15) 1.071(3) 0.3830(14) 0.036(5) Uiso 1 1 d . . . . .
H1 H 0.1044(17) 0.508(3) 0.4277(15) 0.040(5) Uiso 1 1 d . . . . .
H7A H -0.0467(17) 0.427(3) 0.3255(17) 0.046(6) Uiso 1 1 d . . . . .
H7B H -0.072(2) 0.473(4) 0.3996(18) 0.062(7) Uiso 1 1 d . . . . .
H4A H 0.5549(18) 0.844(4) 0.3365(18) 0.058(7) Uiso 1 1 d . . . . .
H3 H 0.7753(17) 0.885(3) 0.6237(16) 0.045(6) Uiso 1 1 d . . . . .
H4 H 0.4854(19) 0.749(4) 0.4853(19) 0.072(8) Uiso 1 1 d . . . . .
H13A H 0.3572(18) 0.606(4) 0.3165(16) 0.051(6) Uiso 1 1 d . . . . .
H13B H 0.3421(15) 0.829(3) 0.3330(15) 0.039(5) Uiso 1 1 d . . . . .
H13C H 0.2503(16) 0.701(3) 0.2597(16) 0.042(6) Uiso 1 1 d . . . . .
H14A H 0.3727(16) 0.696(3) 0.7440(15) 0.042(5) Uiso 1 1 d . . . . .
H14B H 0.4137(15) 0.486(3) 0.7465(14) 0.037(5) Uiso 1 1 d . . . . .
H14C H 0.4849(18) 0.672(4) 0.7780(18) 0.055(7) 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
O5 C8 1.2209(17) . ?
O4 C6 1.3628(16) . ?
O4 H4A 0.95(3) . ?
O6 C9 1.2177(16) . ?
O2 C7 1.2900(17) . ?
O3 C2 1.3507(17) . ?
O3 H3 0.91(2) . ?
O1 C7 1.2487(17) . ?
N1 C9 1.3866(17) . ?
N1 C8 1.3859(16) . ?
N1 H1 0.92(2) . ?
N4 C10 1.3635(17) . ?
N4 C12 1.3450(17) . ?
N4 H4 1.06(3) . ?
N3 C12 1.3266(17) . ?
N3 C11 1.3868(16) . ?
N3 C14 1.4698(16) . ?
N2 C10 1.3574(17) . ?
N2 C9 1.3890(17) . ?
N2 C13 1.4656(17) . ?
O7 H7A 0.93(2) . ?
O7 H7B 0.86(3) . ?
C10 C11 1.3660(18) . ?
C6 C1 1.4106(18) . ?
C6 C5 1.3884(19) . ?
C12 H12 0.948(19) . ?
C11 C8 1.4379(18) . ?
C7 C1 1.4841(18) . ?
C1 C2 1.4172(18) . ?
C14 H14A 1.00(2) . ?
C14 H14B 0.96(2) . ?
C14 H14C 0.96(3) . ?
C3 C2 1.390(2) . ?
C3 C4 1.379(2) . ?
C3 H3A 0.99(2) . ?
C5 C4 1.391(2) . ?
C5 H5 1.016(18) . ?
C13 H13A 0.98(2) . ?
C13 H13B 0.99(2) . ?
C13 H13C 0.99(2) . ?
C4 H4B 1.00(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
C6 O4 H4A 106.1(15) . . ?
C2 O3 H3 99.7(14) . . ?
C9 N1 H1 111.1(14) . . ?
C8 N1 C9 129.28(11) . . ?
C8 N1 H1 119.5(14) . . ?
C10 N4 H4 131.1(15) . . ?
C12 N4 C10 106.44(11) . . ?
C12 N4 H4 122.4(15) . . ?
C12 N3 C11 107.65(11) . . ?
C12 N3 C14 125.51(11) . . ?
C11 N3 C14 126.84(11) . . ?
C10 N2 C9 118.26(11) . . ?
C10 N2 C13 121.34(11) . . ?
C9 N2 C13 120.40(11) . . ?
H7A O7 H7B 106(2) . . ?
N4 C10 C11 109.07(11) . . ?
N2 C10 N4 126.66(12) . . ?
N2 C10 C11 124.23(12) . . ?
O6 C9 N1 121.68(12) . . ?
O6 C9 N2 122.20(12) . . ?
N1 C9 N2 116.12(11) . . ?
O4 C6 C1 121.01(12) . . ?
O4 C6 C5 117.46(12) . . ?
C5 C6 C1 121.54(12) . . ?
N4 C12 H12 124.7(11) . . ?
N3 C12 N4 110.68(11) . . ?
N3 C12 H12 124.6(11) . . ?
N3 C11 C8 132.35(12) . . ?
C10 C11 N3 106.14(11) . . ?
C10 C11 C8 121.41(12) . . ?
O2 C7 C1 117.59(12) . . ?
O1 C7 O2 122.05(12) . . ?
O1 C7 C1 120.35(12) . . ?
C6 C1 C7 121.99(12) . . ?
C6 C1 C2 117.91(12) . . ?
C2 C1 C7 120.09(12) . . ?
O5 C8 N1 122.27(12) . . ?
O5 C8 C11 127.06(12) . . ?
N1 C8 C11 110.67(11) . . ?
N3 C14 H14A 109.5(12) . . ?
N3 C14 H14B 110.4(13) . . ?
N3 C14 H14C 110.9(15) . . ?
H14A C14 H14B 105.5(18) . . ?
H14A C14 H14C 106.8(19) . . ?
H14B C14 H14C 113.5(19) . . ?
C2 C3 H3A 118.5(12) . . ?
C4 C3 C2 119.73(13) . . ?
C4 C3 H3A 121.7(12) . . ?
O3 C2 C1 121.22(12) . . ?
O3 C2 C3 118.33(12) . . ?
C3 C2 C1 120.44(13) . . ?
C6 C5 C4 118.60(13) . . ?
C6 C5 H5 119.8(10) . . ?
C4 C5 H5 121.6(10) . . ?
N2 C13 H13A 110.6(14) . . ?
N2 C13 H13B 109.8(12) . . ?
N2 C13 H13C 108.2(12) . . ?
H13A C13 H13B 106.3(18) . . ?
H13A C13 H13C 110.6(19) . . ?
H13B C13 H13C 111.3(18) . . ?
C3 C4 C5 121.77(13) . . ?
C3 C4 H4B 121.4(11) . . ?
C5 C4 H4B 116.8(11) . . ?

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
N1 H1 O7 0.92(2) 1.81(2) 2.7354(15) 179(2) .
O7 H7A O4 0.93(2) 1.90(2) 2.8264(15) 177(2) 2_545
O7 H7B O5 0.86(3) 1.98(3) 2.8267(15) 167(3) 3_566
O4 H4A O2 0.95(3) 1.68(3) 2.5486(13) 150(2) .
O3 H3 O1 0.91(2) 1.68(2) 2.5540(14) 161(2) .
N4 H4 O2 1.06(3) 1.50(3) 2.5637(15) 180(2) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C6 C1 C7 -0.2(2) . . . . ?
O4 C6 C1 C2 -179.85(12) . . . . ?
O4 C6 C5 C4 179.16(13) . . . . ?
O2 C7 C1 C6 -2.0(2) . . . . ?
O2 C7 C1 C2 177.60(12) . . . . ?
O1 C7 C1 C6 178.32(13) . . . . ?
O1 C7 C1 C2 -2.0(2) . . . . ?
N4 C10 C11 N3 0.73(15) . . . . ?
N4 C10 C11 C8 177.54(12) . . . . ?
N3 C11 C8 O5 -2.5(2) . . . . ?
N3 C11 C8 N1 177.52(13) . . . . ?
N2 C10 C11 N3 -177.28(12) . . . . ?
N2 C10 C11 C8 -0.5(2) . . . . ?
C10 N4 C12 N3 0.60(15) . . . . ?
C10 N2 C9 O6 179.98(13) . . . . ?
C10 N2 C9 N1 0.27(18) . . . . ?
C10 C11 C8 O5 -178.34(13) . . . . ?
C10 C11 C8 N1 1.67(18) . . . . ?
C9 N1 C8 O5 177.84(13) . . . . ?
C9 N1 C8 C11 -2.17(19) . . . . ?
C9 N2 C10 N4 -178.26(13) . . . . ?
C9 N2 C10 C11 -0.6(2) . . . . ?
C6 C1 C2 O3 179.68(12) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C6 C5 C4 C3 0.9(2) . . . . ?
C12 N4 C10 N2 177.14(13) . . . . ?
C12 N4 C10 C11 -0.82(15) . . . . ?
C12 N3 C11 C10 -0.36(15) . . . . ?
C12 N3 C11 C8 -176.68(14) . . . . ?
C11 N3 C12 N4 -0.14(16) . . . . ?
C7 C1 C2 O3 0.0(2) . . . . ?
C7 C1 C2 C3 -179.13(13) . . . . ?
C1 C6 C5 C4 -0.5(2) . . . . ?
C8 N1 C9 O6 -178.44(13) . . . . ?
C8 N1 C9 N2 1.3(2) . . . . ?
C14 N3 C12 N4 180.00(12) . . . . ?
C14 N3 C11 C10 179.49(13) . . . . ?
C14 N3 C11 C8 3.2(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C5 C6 C1 C7 179.43(13) . . . . ?
C5 C6 C1 C2 -0.2(2) . . . . ?
C13 N2 C10 N4 0.9(2) . . . . ?
C13 N2 C10 C11 178.56(13) . . . . ?
C13 N2 C9 O6 0.8(2) . . . . ?
C13 N2 C9 N1 -178.89(12) . . . . ?
C4 C3 C2 O3 -179.31(13) . . . . ?
C4 C3 C2 C1 -0.1(2) . . . . ?

_olex2_date_sample_data_collection 2019-03-09
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-26DHBA-WAT
_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 1.249
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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_tb-k25dhb-1-1bnext
_database_code_depnum_ccdc_archive 'CCDC 1938144'
loop_
_audit_author_name
_audit_author_address
'Mateusz Goldyn'
;Adam Mickiewicz University, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_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        'theobromine-2,5-dihydroxybenzoic acid'
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H6 O4'
_chemical_formula_sum            'C14 H14 N4 O6'
_chemical_formula_weight         334.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 N4 O6'
_chemical_oxdiff_usercomment     '130.5 K (poczatek) 0.04 x 0.10 x 0.28'
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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8492(3)
_cell_length_b                   7.9605(4)
_cell_length_c                   14.0276(8)
_cell_angle_alpha                79.391(4)
_cell_angle_beta                 78.550(4)
_cell_angle_gamma                77.232(4)
_cell_volume                     723.16(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5805
_cell_measurement_temperature    130.3(4)
_cell_measurement_theta_max      75.8000
_cell_measurement_theta_min      3.2210
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.758
_exptl_absorpt_coefficient_mu    1.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_preparation       
'theobromine and 2,5-dihydroxybenzoic acid was dissolved in methanol-water solution'
_exptl_crystal_recrystallization_method 
'cocrystallization by slow evaporation from methanol-water solution'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11318
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.366
_diffrn_reflns_theta_min         3.250
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.3(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -97.00  -2.00   1.00    1.25    --  -41.24 125.00 -60.00   95
  2  ω      2.00  97.00   1.00    1.25    --   41.24-125.00-180.00   95
  3  ω    -33.00  66.00   1.00    1.25    --   41.24 -37.00  30.00   99
  4  ω     17.00 116.00   1.00    1.25    --   41.24  37.00 -60.00   99
  5  ω     13.00 113.00   1.00    1.25    --   41.24  57.00-180.00  100
  6  ω     36.00  69.00   1.00   11.25    --  112.00 -30.00-150.00   33
  7  ω     39.00  77.00   1.00   11.25    --  112.00 -45.00 120.00   38
  8  ω     29.00 110.00   1.00   11.25    --  112.00 -94.00  60.00   81
  9  ω     29.00 110.00   1.00   11.25    --  112.00 -94.00 150.00   81
 10  ω     36.00  69.00   1.00   11.25    --  112.00 -30.00 -90.00   33
 11  ω     36.00 113.00   1.00   11.25    --  112.00-111.00-180.00   77
 12  ω     36.00 113.00   1.00   11.25    --  112.00-111.00-120.00   77
 13  ω     36.00  69.00   1.00   11.25    --  112.00 -30.00  60.00   33
 14  ω     36.00  69.00   1.00   11.25    --  112.00 -30.00 -60.00   33
 15  ω     39.00  77.00   1.00   11.25    --  112.00 -45.00  30.00   38
 16  ω     36.00 113.00   1.00   11.25    --  112.00-111.00 -30.00   77
 17  ω     36.00 145.00   1.00   11.25    --  112.00 -77.00-120.00  109
 18  ω     84.00 158.00   1.00   11.25    --  112.00  30.00-120.00   74
 19  ω     36.00 145.00   1.00   11.25    --  112.00 -77.00   0.00  109
 20  ω     24.00 158.00   1.00   11.25    --  112.00   0.00-150.00  134
 21  ω     36.00 113.00   1.00   11.25    --  112.00-111.00  30.00   77
 22  ω     84.00 158.00   1.00   11.25    --  112.00  30.00  60.00   74
 23  ω     39.00  77.00   1.00   11.25    --  112.00 -45.00-180.00   38
 24  ω     86.00 158.00   1.00   11.25    --  112.00  45.00 -60.00   72
 25  ω   -121.00   0.00   1.00    1.25    --  -41.24 -19.00  60.00  121
 26  ω   -116.00 -17.00   1.00    1.25    --  -41.24 -37.00   0.00   99
 27  ω    -39.00  82.00   1.00    1.25    --   41.24 -19.00-180.00  121
 28  ω      9.00 117.00   1.00    1.25    --   41.24  77.00-120.00  108
 29  ω      9.00 117.00   1.00    1.25    --   41.24  77.00 -30.00  108
 30  ω      9.00 117.00   1.00    1.25    --   41.24  77.00 120.00  108
 31  ω      9.00 117.00   1.00    1.25    --   41.24  77.00  30.00  108
 32  ω     86.00 137.00   1.00   11.25    --  112.00  45.00 -30.00   51
 33  ω     83.00 158.00   1.00   11.25    --  112.00  61.00  90.00   75
 34  ω     83.00 158.00   1.00   11.25    --  112.00  61.00-180.00   75
 35  ω     79.00 158.00   1.00   11.25    --  112.00  77.00-120.00   79
 36  ω     86.00 158.00   1.00   11.25    --  112.00  45.00   0.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0522100000
_diffrn_orient_matrix_UB_12      -0.0935246000
_diffrn_orient_matrix_UB_13      -0.0912828000
_diffrn_orient_matrix_UB_21      -0.2279168000
_diffrn_orient_matrix_UB_22      0.0174137000
_diffrn_orient_matrix_UB_23      -0.0015604000
_diffrn_orient_matrix_UB_31      -0.0007338000
_diffrn_orient_matrix_UB_32      0.1766108000
_diffrn_orient_matrix_UB_33      -0.0670619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2678
_reflns_number_total             2963
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.410
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.047
_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)+(0.1061P)²+0.2879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1553
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O5 O 1.0427(2) 0.77843(16) 0.02734(9) 0.0284(3) Uani 1 1 d . . . . .
O2 O 0.70432(19) 0.51625(16) 0.54411(9) 0.0287(3) Uani 1 1 d . . . . .
O6 O 0.7262(2) 1.17284(16) 0.23346(9) 0.0295(3) Uani 1 1 d . . . . .
O3 O 0.7864(2) 0.00039(17) 0.68386(10) 0.0332(3) Uani 1 1 d . . . . .
O1 O 0.8256(2) 0.23549(17) 0.52934(9) 0.0314(3) Uani 1 1 d . . . . .
O4 O 0.3773(2) 0.53067(19) 0.89567(10) 0.0346(3) Uani 1 1 d . . . . .
N2 N 0.7827(2) 0.88877(18) 0.30368(10) 0.0225(3) Uani 1 1 d . . . . .
N1 N 0.8877(2) 0.96957(18) 0.13472(10) 0.0234(3) Uani 1 1 d . . . . .
N3 N 1.0083(2) 0.49721(18) 0.21114(10) 0.0226(3) Uani 1 1 d . . . . .
N4 N 0.8610(2) 0.57534(18) 0.35712(10) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.9504(2) 0.6758(2) 0.19721(12) 0.0219(4) Uani 1 1 d . . . . .
C6 C 0.5521(2) 0.4442(2) 0.73983(12) 0.0233(4) Uani 1 1 d . . . . .
C10 C 0.8607(2) 0.7190(2) 0.28834(12) 0.0209(3) Uani 1 1 d . . . . .
C8 C 0.9678(2) 0.8030(2) 0.11212(12) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.7941(2) 1.0193(2) 0.22500(12) 0.0226(3) Uani 1 1 d . . . . .
C1 C 0.6551(2) 0.3095(2) 0.68579(12) 0.0228(4) Uani 1 1 d . . . . .
C12 C 0.9517(3) 0.4442(2) 0.30681(12) 0.0242(4) Uani 1 1 d . . . . .
C5 C 0.4803(2) 0.4067(2) 0.83931(13) 0.0268(4) Uani 1 1 d . . . . .
C2 C 0.6862(2) 0.1365(2) 0.73235(13) 0.0260(4) Uani 1 1 d . . . . .
C7 C 0.7353(2) 0.3504(2) 0.57947(12) 0.0242(4) Uani 1 1 d . . . . .
C13 C 0.6888(3) 0.9310(2) 0.40194(13) 0.0288(4) Uani 1 1 d . . . . .
C3 C 0.6141(3) 0.1013(2) 0.83263(14) 0.0314(4) Uani 1 1 d . . . . .
C14 C 1.1144(3) 0.3889(2) 0.13578(14) 0.0288(4) Uani 1 1 d . . . . .
C4 C 0.5139(3) 0.2340(3) 0.88543(13) 0.0304(4) Uani 1 1 d . . . . .
H6 H 0.537(3) 0.555(3) 0.7033(16) 0.026(5) Uiso 1 1 d . . . . .
H4A H 0.466(3) 0.213(3) 0.9577(17) 0.027(5) Uiso 1 1 d . . . . .
H14A H 1.230(4) 0.433(4) 0.104(2) 0.041(6) Uiso 1 1 d . . . . .
H3A H 0.636(3) -0.017(3) 0.8644(18) 0.031(6) Uiso 1 1 d . . . . .
H4 H 0.360(4) 0.628(4) 0.858(2) 0.041(7) Uiso 1 1 d . . . . .
H12 H 0.978(3) 0.326(3) 0.3365(17) 0.025(5) Uiso 1 1 d . . . . .
H1 H 0.898(3) 1.053(3) 0.0861(18) 0.028(5) Uiso 1 1 d . . . . .
H3 H 0.821(4) 0.051(4) 0.618(2) 0.058(8) Uiso 1 1 d . . . . .
H14B H 1.025(4) 0.398(4) 0.091(2) 0.050(7) Uiso 1 1 d . . . . .
H2 H 0.764(4) 0.525(4) 0.476(2) 0.045(7) Uiso 1 1 d . . . . .
H13A H 0.568(6) 0.894(5) 0.422(3) 0.086(11) Uiso 1 1 d . . . . .
H14C H 1.143(4) 0.267(4) 0.171(2) 0.057(8) Uiso 1 1 d . . . . .
H13B H 0.778(5) 0.867(5) 0.450(3) 0.080(11) Uiso 1 1 d . . . . .
H13C H 0.665(6) 1.051(5) 0.402(3) 0.089(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
O5 C8 1.231(2) . ?
O2 C7 1.308(2) . ?
O2 H2 0.96(3) . ?
O6 C9 1.227(2) . ?
O3 C2 1.366(2) . ?
O3 H3 0.94(3) . ?
O1 C7 1.236(2) . ?
O4 C5 1.362(2) . ?
O4 H4 0.85(3) . ?
N2 C10 1.378(2) . ?
N2 C9 1.372(2) . ?
N2 C13 1.466(2) . ?
N1 C8 1.387(2) . ?
N1 C9 1.386(2) . ?
N1 H1 0.87(3) . ?
N3 C11 1.377(2) . ?
N3 C12 1.337(2) . ?
N3 C14 1.464(2) . ?
N4 C10 1.354(2) . ?
N4 C12 1.336(2) . ?
C11 C10 1.374(2) . ?
C11 C8 1.420(2) . ?
C6 C1 1.405(2) . ?
C6 C5 1.385(2) . ?
C6 H6 0.93(2) . ?
C1 C2 1.401(2) . ?
C1 C7 1.485(2) . ?
C12 H12 0.95(2) . ?
C5 C4 1.398(3) . ?
C2 C3 1.393(3) . ?
C13 H13A 0.92(4) . ?
C13 H13B 0.99(4) . ?
C13 H13C 0.93(4) . ?
C3 C4 1.379(3) . ?
C3 H3A 0.96(3) . ?
C14 H14A 0.93(3) . ?
C14 H14B 0.95(3) . ?
C14 H14C 1.00(3) . ?
C4 H4A 1.00(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
C7 O2 H2 106.4(17) . . ?
C2 O3 H3 105.0(19) . . ?
C5 O4 H4 107.4(18) . . ?
C10 N2 C13 121.15(15) . . ?
C9 N2 C10 118.83(14) . . ?
C9 N2 C13 120.02(14) . . ?
C8 N1 H1 115.6(15) . . ?
C9 N1 C8 128.47(15) . . ?
C9 N1 H1 115.9(15) . . ?
C11 N3 C14 126.33(14) . . ?
C12 N3 C11 106.33(14) . . ?
C12 N3 C14 127.33(15) . . ?
C12 N4 C10 104.06(14) . . ?
N3 C11 C8 132.25(15) . . ?
C10 C11 N3 105.49(15) . . ?
C10 C11 C8 122.26(16) . . ?
C1 C6 H6 114.8(14) . . ?
C5 C6 C1 120.25(16) . . ?
C5 C6 H6 125.0(14) . . ?
N4 C10 N2 126.54(15) . . ?
N4 C10 C11 111.08(15) . . ?
C11 C10 N2 122.38(16) . . ?
O5 C8 N1 121.18(15) . . ?
O5 C8 C11 127.50(16) . . ?
N1 C8 C11 111.31(14) . . ?
O6 C9 N2 122.12(15) . . ?
O6 C9 N1 121.16(16) . . ?
N2 C9 N1 116.73(15) . . ?
C6 C1 C7 120.13(15) . . ?
C2 C1 C6 120.14(16) . . ?
C2 C1 C7 119.71(15) . . ?
N3 C12 H12 123.6(14) . . ?
N4 C12 N3 113.04(15) . . ?
N4 C12 H12 123.4(14) . . ?
O4 C5 C6 123.22(16) . . ?
O4 C5 C4 117.53(16) . . ?
C6 C5 C4 119.25(16) . . ?
O3 C2 C1 122.80(16) . . ?
O3 C2 C3 118.35(15) . . ?
C3 C2 C1 118.85(16) . . ?
O2 C7 C1 114.77(15) . . ?
O1 C7 O2 123.20(16) . . ?
O1 C7 C1 122.02(16) . . ?
N2 C13 H13A 111(2) . . ?
N2 C13 H13B 109(2) . . ?
N2 C13 H13C 110(2) . . ?
H13A C13 H13B 106(3) . . ?
H13A C13 H13C 109(3) . . ?
H13B C13 H13C 112(3) . . ?
C2 C3 H3A 118.7(14) . . ?
C4 C3 C2 120.79(17) . . ?
C4 C3 H3A 120.5(14) . . ?
N3 C14 H14A 107.5(16) . . ?
N3 C14 H14B 107.3(17) . . ?
N3 C14 H14C 105.9(17) . . ?
H14A C14 H14B 110(2) . . ?
H14A C14 H14C 115(2) . . ?
H14B C14 H14C 111(2) . . ?
C5 C4 H4A 116.9(13) . . ?
C3 C4 C5 120.72(17) . . ?
C3 C4 H4A 122.4(13) . . ?

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
O4 H4 O6 0.85(3) 1.91(3) 2.7477(19) 168(2) 2_676
N1 H1 O5 0.87(3) 1.92(3) 2.7808(19) 172(2) 2_775
O3 H3 O1 0.94(3) 1.75(3) 2.6019(19) 150(3) .
O2 H2 N4 0.96(3) 1.68(3) 2.6277(19) 171(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C2 C3 C4 179.28(15) . . . . ?
O4 C5 C4 C3 178.92(16) . . . . ?
N3 C11 C10 N2 -179.95(14) . . . . ?
N3 C11 C10 N4 -0.06(18) . . . . ?
N3 C11 C8 O5 0.3(3) . . . . ?
N3 C11 C8 N1 -179.51(16) . . . . ?
C11 N3 C12 N4 -0.21(19) . . . . ?
C6 C1 C2 O3 -179.53(14) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C1 C7 O2 1.1(2) . . . . ?
C6 C1 C7 O1 -179.54(15) . . . . ?
C6 C5 C4 C3 -1.1(3) . . . . ?
C10 N2 C9 O6 179.44(15) . . . . ?
C10 N2 C9 N1 -0.9(2) . . . . ?
C10 N4 C12 N3 0.16(19) . . . . ?
C10 C11 C8 O5 -179.09(16) . . . . ?
C10 C11 C8 N1 1.1(2) . . . . ?
C8 N1 C9 O6 -178.43(15) . . . . ?
C8 N1 C9 N2 2.0(3) . . . . ?
C8 C11 C10 N2 -0.4(3) . . . . ?
C8 C11 C10 N4 179.46(14) . . . . ?
C9 N2 C10 N4 -179.56(14) . . . . ?
C9 N2 C10 C11 0.3(2) . . . . ?
C9 N1 C8 O5 178.22(16) . . . . ?
C9 N1 C8 C11 -2.0(2) . . . . ?
C1 C6 C5 O4 -179.21(14) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C12 N3 C11 C10 0.16(18) . . . . ?
C12 N3 C11 C8 -179.30(17) . . . . ?
C12 N4 C10 N2 179.83(15) . . . . ?
C12 N4 C10 C11 -0.06(18) . . . . ?
C5 C6 C1 C2 -0.1(3) . . . . ?
C5 C6 C1 C7 -178.88(14) . . . . ?
C2 C1 C7 O2 -177.68(14) . . . . ?
C2 C1 C7 O1 1.7(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C7 C1 C2 O3 -0.8(2) . . . . ?
C7 C1 C2 C3 178.46(15) . . . . ?
C13 N2 C10 N4 0.5(3) . . . . ?
C13 N2 C10 C11 -179.67(15) . . . . ?
C13 N2 C9 O6 -0.6(3) . . . . ?
C13 N2 C9 N1 179.04(14) . . . . ?
C14 N3 C11 C10 -178.73(15) . . . . ?
C14 N3 C11 C8 1.8(3) . . . . ?
C14 N3 C12 N4 178.67(15) . . . . ?

_olex2_date_sample_data_collection 2019-03-09
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-25DHBA
_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 1.328
_oxdiff_exptl_absorpt_empirical_full_min 0.725
####################################################################### 
# 
# 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_tb-k24dhb-1-1bspr
_database_code_depnum_ccdc_archive 'CCDC 1938122'
loop_
_audit_author_name
_audit_author_address
'Mateusz Goldyn'
;Adam Mickiewicz University, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_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        'theobromine-2,4-dihydroxybenzoic acid'
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H6 O4'
_chemical_formula_sum            'C14 H14 N4 O6'
_chemical_formula_weight         334.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 N4 O6'
_chemical_oxdiff_usercomment     '131.2 K 0.03x0.07x0.30, sprawdzenie'
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'
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'

_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 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9392(3)
_cell_length_b                   6.3569(2)
_cell_length_c                   28.7601(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.093(3)
_cell_angle_gamma                90
_cell_volume                     1443.29(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2746
_cell_measurement_temperature    132(1)
_cell_measurement_theta_max      74.9190
_cell_measurement_theta_min      5.6550
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.744
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_preparation       
'theobromine and 2,4-dihydroxybenzoic acid in stoichometric ratio (1:1) was dissolved in methanol-water mixture'
_exptl_crystal_recrystallization_method 
'cocrystallization by slow evaporation from methanol-water solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            5993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.088
_diffrn_reflns_theta_min         3.091
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      132(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     59.00 109.00   1.00   12.50    --   41.24  57.00  90.00   50
  2  ω     13.00 112.00   1.00   12.50    --   41.24  57.00-150.00   99
  3  ω      3.00  87.00   1.00   12.50    --   41.24-125.00  90.00   84
  4  ω     46.00  77.00   1.00   29.00    --  112.00 -45.00  60.00   31
  5  ω     36.00  88.00   1.00   29.00    --  112.00-111.00  30.00   52
  6  ω     36.00  65.00   1.00   29.00    --  112.00 -30.00  30.00   29
  7  ω     46.00  74.00   1.00   29.00    --  112.00 -45.00  90.00   28
  8  ω     39.00  65.00   1.00   29.00    --  112.00 -30.00   0.00   26
  9  ω     42.00 101.00   1.00   29.00    --  112.00 -94.00  90.00   59
 10  ω     40.00  67.00   1.00   29.00    --  112.00 -45.00 120.00   27
 11  ω    120.00 152.00   1.00   29.00    --  112.00  30.00-120.00   32
 12  ω     50.00  77.00   1.00   29.00    --  112.00 -45.00 -90.00   27
 13  ω     54.00  82.00   1.00   29.00    --  112.00 -77.00 120.00   28
 14  ω    113.00 139.00   1.00   29.00    --  112.00 -77.00 120.00   26
 15  ω     88.00 114.00   1.00   29.00    --  112.00  30.00-120.00   26
 16  ω    109.00 142.00   1.00   29.00    --  112.00 -15.00-150.00   33
 17  ω     45.00 107.00   1.00   29.00    --  112.00-111.00  60.00   62
 18  ω     30.00 105.00   1.00   29.00    --  112.00 -15.00-150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1893770000
_diffrn_orient_matrix_UB_12      0.0096879000
_diffrn_orient_matrix_UB_13      -0.0073181000
_diffrn_orient_matrix_UB_21      -0.0096113000
_diffrn_orient_matrix_UB_22      -0.2262095000
_diffrn_orient_matrix_UB_23      -0.0193290000
_diffrn_orient_matrix_UB_31      -0.0465081000
_diffrn_orient_matrix_UB_32      0.0862326000
_diffrn_orient_matrix_UB_33      -0.0497330000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2574
_reflns_number_total             2932
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.533
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.096
_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)+(0.0751P)²+0.7315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1414
_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
2. Restrained distances
 O3-H3
 1 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3A), C6(H6), C12(H12)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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
O6 O 0.67662(18) 0.9929(2) 0.27695(5) 0.0343(3) Uani 1 1 d . . . . .
O4 O -0.05815(19) -0.5978(2) 0.31126(5) 0.0344(3) Uani 1 1 d . . . . .
O5 O 0.91673(19) 1.1083(2) 0.42504(5) 0.0362(4) Uani 1 1 d . . . . .
O2 O 0.40243(19) 0.1974(3) 0.35751(5) 0.0394(4) Uani 1 1 d . . . . .
O1 O 0.4163(2) 0.0602(3) 0.42935(5) 0.0411(4) Uani 1 1 d . . . . .
O3 O 0.2593(2) -0.2886(3) 0.44119(5) 0.0428(4) Uani 1 1 d D . . . .
N1 N 0.7916(2) 1.0386(3) 0.35158(5) 0.0287(4) Uani 1 1 d . . . . .
N2 N 0.6326(2) 0.7363(3) 0.33013(5) 0.0297(4) Uani 1 1 d . . . . .
N4 N 0.6082(2) 0.4948(3) 0.39470(6) 0.0326(4) Uani 1 1 d . . . . .
N3 N 0.7596(2) 0.6780(3) 0.45018(5) 0.0322(4) Uani 1 1 d . . . . .
C11 C 0.7571(2) 0.7925(3) 0.40933(6) 0.0283(4) Uani 1 1 d . . . . .
C8 C 0.8309(2) 0.9898(3) 0.39891(6) 0.0286(4) Uani 1 1 d . . . . .
C10 C 0.6634(2) 0.6743(3) 0.37621(6) 0.0288(4) Uani 1 1 d . . . . .
C9 C 0.6980(2) 0.9240(3) 0.31730(6) 0.0284(4) Uani 1 1 d . . . . .
C4 C 0.0426(2) -0.4363(3) 0.32871(7) 0.0297(4) Uani 1 1 d . . . . .
C1 C 0.2484(2) -0.1125(3) 0.36722(7) 0.0306(4) Uani 1 1 d . . . . .
C5 C 0.0841(2) -0.2698(3) 0.30041(7) 0.0317(4) Uani 1 1 d . . . . .
H5 H 0.043233 -0.266754 0.268885 0.038 Uiso 1 1 calc R . . . .
C2 C 0.2041(2) -0.2802(3) 0.39503(7) 0.0313(4) Uani 1 1 d . . . . .
C3 C 0.1014(3) -0.4424(3) 0.37585(7) 0.0316(4) Uani 1 1 d . . . . .
H3A H 0.072614 -0.553734 0.394442 0.038 Uiso 1 1 calc R . . . .
C6 C 0.1862(2) -0.1099(3) 0.31965(7) 0.0318(4) Uani 1 1 d . . . . .
H6 H 0.214258 0.001127 0.300872 0.038 Uiso 1 1 calc R . . . .
C7 C 0.3615(2) 0.0553(3) 0.38764(7) 0.0332(4) Uani 1 1 d . . . . .
C12 C 0.6701(3) 0.5032(3) 0.43966(7) 0.0359(5) Uani 1 1 d . . . . .
H12 H 0.652796 0.398739 0.461298 0.043 Uiso 1 1 calc R . . . .
C13 C 0.5359(3) 0.6004(4) 0.29583(7) 0.0383(5) Uani 1 1 d . . . . .
H13A H 0.588848 0.464634 0.295743 0.057 Uiso 1 1 calc GR . . . .
H13B H 0.533102 0.662232 0.265308 0.057 Uiso 1 1 calc GR . . . .
H13C H 0.422336 0.585200 0.303978 0.057 Uiso 1 1 calc GR . . . .
C14 C 0.8488(3) 0.7363(4) 0.49562(7) 0.0411(5) Uani 1 1 d . . . . .
H14A H 0.968036 0.746350 0.492984 0.062 Uiso 1 1 calc GR . . . .
H14B H 0.829121 0.631030 0.518368 0.062 Uiso 1 1 calc GR . . . .
H14C H 0.807535 0.869592 0.505259 0.062 Uiso 1 1 calc GR . . . .
H1 H 0.840(3) 1.155(5) 0.3419(9) 0.038(6) Uiso 1 1 d . . . . .
H4 H -0.098(4) -0.576(6) 0.2810(11) 0.065(9) Uiso 1 1 d . . . . .
H3 H 0.341(4) -0.161(5) 0.4469(12) 0.092(12) Uiso 1 1 d D . . . .
H2 H 0.490(5) 0.308(6) 0.3739(12) 0.086(11) 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
O6 C9 1.235(2) . ?
O4 C4 1.364(2) . ?
O4 H4 0.91(3) . ?
O5 C8 1.220(2) . ?
O2 C7 1.316(3) . ?
O2 H2 1.06(4) . ?
O1 C7 1.232(3) . ?
O3 C2 1.354(2) . ?
O3 H3 1.044(19) . ?
N1 C8 1.399(2) . ?
N1 C9 1.378(2) . ?
N1 H1 0.89(3) . ?
N2 C10 1.379(2) . ?
N2 C9 1.368(3) . ?
N2 C13 1.466(3) . ?
N4 C10 1.352(3) . ?
N4 C12 1.335(3) . ?
N3 C11 1.381(2) . ?
N3 C12 1.337(3) . ?
N3 C14 1.466(3) . ?
C11 C8 1.430(3) . ?
C11 C10 1.369(3) . ?
C4 C5 1.396(3) . ?
C4 C3 1.387(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.405(3) . ?
C1 C7 1.475(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(3) . ?
C2 C3 1.391(3) . ?
C3 H3A 0.9300 . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 O4 H4 112(2) . . ?
C7 O2 H2 111(2) . . ?
C2 O3 H3 105(2) . . ?
C8 N1 H1 115.4(17) . . ?
C9 N1 C8 128.82(18) . . ?
C9 N1 H1 115.6(16) . . ?
C10 N2 C13 120.33(18) . . ?
C9 N2 C10 118.35(16) . . ?
C9 N2 C13 121.30(16) . . ?
C12 N4 C10 104.23(17) . . ?
C11 N3 C14 125.98(18) . . ?
C12 N3 C11 106.62(16) . . ?
C12 N3 C14 127.36(18) . . ?
N3 C11 C8 132.19(17) . . ?
C10 C11 N3 105.12(17) . . ?
C10 C11 C8 122.69(17) . . ?
O5 C8 N1 121.00(19) . . ?
O5 C8 C11 128.86(18) . . ?
N1 C8 C11 110.14(16) . . ?
N4 C10 N2 125.96(18) . . ?
N4 C10 C11 111.38(17) . . ?
C11 C10 N2 122.67(18) . . ?
O6 C9 N1 119.65(19) . . ?
O6 C9 N2 123.01(17) . . ?
N2 C9 N1 117.34(16) . . ?
O4 C4 C5 121.44(17) . . ?
O4 C4 C3 117.52(18) . . ?
C3 C4 C5 121.04(19) . . ?
C2 C1 C6 118.79(19) . . ?
C2 C1 C7 120.17(18) . . ?
C6 C1 C7 121.03(19) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.34(18) . . ?
C6 C5 H5 120.3 . . ?
O3 C2 C1 121.01(18) . . ?
O3 C2 C3 118.32(18) . . ?
C3 C2 C1 120.67(18) . . ?
C4 C3 C2 119.28(19) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.88(19) . . ?
C5 C6 H6 119.6 . . ?
O2 C7 C1 114.62(18) . . ?
O1 C7 O2 122.50(19) . . ?
O1 C7 C1 122.9(2) . . ?
N4 C12 N3 112.65(18) . . ?
N4 C12 H12 123.7 . . ?
N3 C12 H12 123.7 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
N1 H1 O4 0.89(3) 2.02(3) 2.899(2) 172(2) 1_675
O4 H4 O6 0.91(3) 1.77(3) 2.6734(19) 174(3) 2_535
O3 H3 O1 1.044(19) 1.63(3) 2.584(2) 150(3) .
O2 H2 N4 1.06(4) 1.59(4) 2.648(2) 173(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C4 C5 C6 179.93(18) . . . . ?
O4 C4 C3 C2 -179.79(18) . . . . ?
O3 C2 C3 C4 179.60(18) . . . . ?
N3 C11 C8 O5 -0.3(4) . . . . ?
N3 C11 C8 N1 179.7(2) . . . . ?
N3 C11 C10 N2 -179.59(17) . . . . ?
N3 C11 C10 N4 0.3(2) . . . . ?
C11 N3 C12 N4 -0.2(2) . . . . ?
C8 N1 C9 O6 -179.90(18) . . . . ?
C8 N1 C9 N2 0.1(3) . . . . ?
C8 C11 C10 N2 -0.1(3) . . . . ?
C8 C11 C10 N4 179.82(17) . . . . ?
C10 N2 C9 O6 -179.74(18) . . . . ?
C10 N2 C9 N1 0.3(3) . . . . ?
C10 N4 C12 N3 0.4(2) . . . . ?
C10 C11 C8 O5 -179.6(2) . . . . ?
C10 C11 C8 N1 0.4(3) . . . . ?
C9 N1 C8 O5 179.63(19) . . . . ?
C9 N1 C8 C11 -0.4(3) . . . . ?
C9 N2 C10 N4 179.81(18) . . . . ?
C9 N2 C10 C11 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C2 C1 C7 O2 176.01(18) . . . . ?
C2 C1 C7 O1 -2.5(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C6 C1 C2 O3 -179.26(18) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C1 C7 O2 -2.7(3) . . . . ?
C6 C1 C7 O1 178.80(19) . . . . ?
C7 C1 C2 O3 2.0(3) . . . . ?
C7 C1 C2 C3 -178.18(18) . . . . ?
C7 C1 C6 C5 178.34(18) . . . . ?
C12 N4 C10 N2 179.48(19) . . . . ?
C12 N4 C10 C11 -0.4(2) . . . . ?
C12 N3 C11 C8 -179.5(2) . . . . ?
C12 N3 C11 C10 -0.1(2) . . . . ?
C13 N2 C10 N4 -1.8(3) . . . . ?
C13 N2 C10 C11 178.08(18) . . . . ?
C13 N2 C9 O6 1.9(3) . . . . ?
C13 N2 C9 N1 -178.06(18) . . . . ?
C14 N3 C11 C8 -1.3(3) . . . . ?
C14 N3 C11 C10 178.11(19) . . . . ?
C14 N3 C12 N4 -178.3(2) . . . . ?

_olex2_date_sample_data_collection 2019-03-10
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-24DHBA
_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 1.337
_oxdiff_exptl_absorpt_empirical_full_min 0.702
