#------------------------------------------------------------------------------
#$Date: 2025-07-06 16:54:42 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300556 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/44/1574447.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1574447
loop_
_publ_author_name
'Metherall, Jessica P.'
'Corner, Philip A.'
'McCabe, James F.'
'Probert, Michael R.'
'Hall, Michael J.'
_publ_section_title
;
 High-throughput encapsulated nanodroplet screening for accelerated
 co-crystal discovery
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              9843
_journal_page_last               9853
_journal_paper_doi               10.1039/D4SC07556K
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C5 H8 O4, C8 H10 N4 O2'
_chemical_formula_sum            'C13 H18 N4 O6'
_chemical_formula_weight         326.31
_chemical_name_systematic        'caffeine_glutaric acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2kmbfz
_audit_creation_date             2025-04-01
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-04-01 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.832(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0056(3)
_cell_length_b                   6.5779(2)
_cell_length_c                   17.0942(4)
_cell_measurement_reflns_used    4784
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      75.8880
_cell_measurement_theta_min      3.4300
_cell_volume                     1448.76(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  79.00   0.50    0.95    --  109.94 -77.00 120.00   74
  2  ω     45.00  72.00   0.50    0.95    --  100.90 -77.00  90.00   54
  3  ω     33.00  61.00   0.50    0.95    --  100.90 -76.00  48.00   56
  4  ω     44.00  72.00   0.50    0.95    --  109.94 -76.00  48.00   56
  5  ω     41.00  80.00   0.50    0.95    --  109.94 -77.00   0.00   78
  6  ω     27.00  55.00   0.50    0.95    --  100.90 -61.00 -30.00   56
  7  ω     43.00  69.00   0.50    0.95    --  109.94 -77.00-180.00   52
  8  ω     25.00  50.00   0.50    0.95    --  100.90 -61.00 -90.00   50
  9  ω     25.00  50.00   0.50    0.95    --  100.90 -61.00 -60.00   50
 10  ω     10.00  35.00   0.50    0.95    --   44.76 -76.00  48.00   50
 11  ω     30.00  55.00   0.50    0.95    --  100.90 -61.00 120.00   50
 12  ω    125.00 152.00   0.50    0.95    --  100.90  77.00 -30.00   54
 13  ω    122.00 172.00   0.50    0.95    --  100.90  61.00-120.00  100
 14  ω    124.00 150.00   0.50    0.95    --  109.94  76.00 174.00   52
 15  ω    129.00 161.00   0.50    0.95    --  100.90  76.00 174.00   64
 16  ω     29.00  80.00   0.50    0.95    --  100.90 -95.00-120.00  102
 17  ω     46.00  92.00   0.50    0.95    --  109.94 -95.00 -90.00   92
 18  ω    -11.00  25.00   0.50    0.95    --  -43.89  38.00-120.00   72
 19  ω     -1.00  33.00   0.50    0.95    --  -43.89  38.00-150.00   68
 20  ω      5.00  33.00   0.50    0.95    --  -43.89  38.00 -90.00   56
 21  ω    -12.00  37.00   0.50    0.95    --  -43.89  38.00 -60.00   98
 22  ω    -13.00  33.00   0.50    0.95    --  -43.89  38.00  60.00   92
 23  ω    -62.00 -22.00   0.50    0.95    --  -43.89  76.00 174.00   80
 24  ω    -42.00 -15.00   0.50    0.95    --  -88.07  61.00 120.00   54
 25  ω    -68.00 -19.00   0.50    0.95    --  -43.89 125.00  60.00   98
 26  ω    -54.00 -28.00   0.50    0.95    --  -88.07  76.00 174.00   52
 27  ω   -154.00-111.00   0.50    0.95    --  -88.07 -77.00 120.00   86
 28  ω   -152.00-116.00   0.50    0.95    --  -88.07 -76.00  48.00   72
 29  ω   -157.00-104.00   0.50    0.95    --  -88.07 -77.00   0.00  106
 30  ω   -149.00-104.00   0.50    0.95    --  -88.07 -77.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1099810000
_diffrn_orient_matrix_UB_12      -0.0709517000
_diffrn_orient_matrix_UB_13      0.0110506000
_diffrn_orient_matrix_UB_21      -0.0465837000
_diffrn_orient_matrix_UB_22      0.1810894000
_diffrn_orient_matrix_UB_23      -0.0499759000
_diffrn_orient_matrix_UB_31      -0.0050564000
_diffrn_orient_matrix_UB_32      -0.1305847000
_diffrn_orient_matrix_UB_33      -0.0752124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8658
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.047
_diffrn_reflns_theta_min         3.430
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.496
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_preparation
;
Crystallised from a saturated solution of caffeine 
and glutaric acid (1:1) in MeNO2.
;
_exptl_crystal_recrystallization_method
'High-throughput screening via the ENaCt protocol using SPT Labtech mosquito.'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     165
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0377
_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)+(0.0589P)²+0.4337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2291
_reflns_number_total             2826
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc07556k2.cif
_cod_data_source_block           caffeine_glutaricacid
_cod_depositor_comments
'Adding full bibliography for 1574434--1574463.cif.'
_cod_database_code               1574447
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_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.
;
_cell_oxdiff_angle_alpha         89.958(3)
_cell_oxdiff_angle_beta          97.890(3)
_cell_oxdiff_angle_gamma         90.062(3)
_cell_oxdiff_length_a            13.0099(5)
_cell_oxdiff_length_b            6.5762(2)
_cell_oxdiff_length_c            17.0956(6)
_cell_oxdiff_measurement_reflns_used 4784
_cell_oxdiff_volume              1448.77(9)
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.887
_diffrn_oxdiff_digest_hkl
;
0176e99aa759eb13746726d40f807a526fadc5
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C4B(H4BA,H4BB), C3B(H3BA,H3BB), C2B(H2BA,H2BB)
3.b Aromatic/amide H refined with riding coordinates:
 C7A(H7A)
3.c Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C3A(H3AA,H3AB,H3AC), C5A(H5AA,H5AB,H5AC)
;
_olex2_exptl_crystal_mounting_method
'Crystal mounted using inert oil from the encapsulation crystallisation technique onto a MiTeGen Kapton micromount.'
_olex2_submission_original_sample_id 'caffeine_glutaric acid'
_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 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.874
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'
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
O4B O 0.89636(9) 0.27838(19) 0.07987(7) 0.0335(3) Uani 1 1 d . . . . .
O1A O 0.25746(9) 0.24994(17) 0.61296(6) 0.0319(3) Uani 1 1 d . . . . .
O2A O 0.14727(9) 0.29174(19) 0.34691(7) 0.0347(3) Uani 1 1 d . . . . .
O1B O 0.75994(9) 0.24704(18) 0.44449(7) 0.0354(3) Uani 1 1 d . . . . .
O2B O 0.64405(9) 0.23540(19) 0.33653(7) 0.0352(3) Uani 1 1 d . . . . .
O3B O 0.75285(9) 0.2996(2) 0.13784(7) 0.0395(3) Uani 1 1 d . . . . .
N1A N 0.47809(10) 0.24487(18) 0.56836(7) 0.0238(3) Uani 1 1 d . . . . .
N4A N 0.20352(10) 0.27221(19) 0.47915(8) 0.0261(3) Uani 1 1 d . . . . .
N3A N 0.32163(10) 0.27630(19) 0.38503(7) 0.0253(3) Uani 1 1 d . . . . .
N2A N 0.50420(10) 0.25915(18) 0.44223(8) 0.0254(3) Uani 1 1 d . . . . .
C6A C 0.40069(12) 0.2637(2) 0.44696(9) 0.0229(3) Uani 1 1 d . . . . .
C1A C 0.38147(12) 0.2552(2) 0.52352(9) 0.0232(3) Uani 1 1 d . . . . .
C7A C 0.54792(12) 0.2475(2) 0.51756(9) 0.0252(3) Uani 1 1 d . . . . .
H7A H 0.620773 0.241803 0.533377 0.030 Uiso 1 1 calc R U . . .
C5B C 0.84661(12) 0.2993(2) 0.14258(9) 0.0266(3) Uani 1 1 d . . . . .
C2A C 0.27964(12) 0.2582(2) 0.54573(9) 0.0245(3) Uani 1 1 d . . . . .
C4A C 0.21990(12) 0.2809(2) 0.39989(9) 0.0263(3) Uani 1 1 d . . . . .
C4B C 0.91998(12) 0.3290(3) 0.21695(9) 0.0312(4) Uani 1 1 d . . . . .
H4BA H 0.966110 0.445185 0.209604 0.037 Uiso 1 1 calc R U . . .
H4BB H 0.964028 0.206354 0.226408 0.037 Uiso 1 1 calc R U . . .
C1B C 0.74039(13) 0.2223(2) 0.37380(9) 0.0299(4) Uani 1 1 d . . . . .
C8A C 0.50005(13) 0.2368(3) 0.65423(9) 0.0309(4) Uani 1 1 d . . . . .
H8AA H 0.471674 0.358196 0.676750 0.046 Uiso 1 1 calc R U . . .
H8AB H 0.575290 0.231765 0.670224 0.046 Uiso 1 1 calc R U . . .
H8AC H 0.467963 0.115133 0.673458 0.046 Uiso 1 1 calc R U . . .
C3B C 0.86707(12) 0.3686(3) 0.28997(9) 0.0317(4) Uani 1 1 d . . . . .
H3BA H 0.918608 0.424498 0.332494 0.038 Uiso 1 1 calc R U . . .
H3BB H 0.811902 0.471643 0.277059 0.038 Uiso 1 1 calc R U . . .
C3A C 0.09477(12) 0.2761(3) 0.49365(11) 0.0338(4) Uani 1 1 d . . . . .
H3AA H 0.060793 0.148553 0.475271 0.051 Uiso 1 1 calc R U . . .
H3AB H 0.058869 0.390404 0.465009 0.051 Uiso 1 1 calc R U . . .
H3AC H 0.092107 0.292058 0.550337 0.051 Uiso 1 1 calc R U . . .
C5A C 0.34390(14) 0.2719(3) 0.30367(9) 0.0335(4) Uani 1 1 d . . . . .
H5AA H 0.386373 0.390042 0.294088 0.050 Uiso 1 1 calc R U . . .
H5AB H 0.278625 0.275826 0.267512 0.050 Uiso 1 1 calc R U . . .
H5AC H 0.381652 0.146947 0.294769 0.050 Uiso 1 1 calc R U . . .
C2B C 0.81956(13) 0.1763(3) 0.31971(10) 0.0347(4) Uani 1 1 d . . . . .
H2BA H 0.786135 0.097020 0.273952 0.042 Uiso 1 1 calc R U . . .
H2BB H 0.875424 0.091572 0.348264 0.042 Uiso 1 1 calc R U . . .
H2B H 0.5980(18) 0.256(3) 0.3719(13) 0.042 Uiso 1 1 d . U . . .
H4B H 0.8542(18) 0.271(3) 0.0394(14) 0.042 Uiso 1 1 d . U . . .
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'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2024-40s32 2024
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
C5B O4B H4B 110.0(15) . . ?
C1B O2B H2B 110.6(14) . . ?
C1A N1A C8A 126.81(13) . . ?
C7A N1A C1A 106.59(12) . . ?
C7A N1A C8A 126.60(14) . . ?
C2A N4A C3A 116.90(13) . . ?
C4A N4A C2A 127.04(13) . . ?
C4A N4A C3A 116.05(13) . . ?
C6A N3A C4A 119.65(13) . . ?
C6A N3A C5A 120.55(13) . . ?
C4A N3A C5A 119.69(13) . . ?
C7A N2A C6A 103.80(12) . . ?
N2A C6A N3A 126.75(13) . . ?
N2A C6A C1A 111.58(13) . . ?
C1A C6A N3A 121.67(14) . . ?
N1A C1A C2A 131.31(13) . . ?
C6A C1A N1A 105.20(13) . . ?
C6A C1A C2A 123.50(14) . . ?
N1A C7A H7A 123.6 . . ?
N2A C7A N1A 112.84(14) . . ?
N2A C7A H7A 123.6 . . ?
O4B C5B C4B 111.96(13) . . ?
O3B C5B O4B 122.77(15) . . ?
O3B C5B C4B 125.24(14) . . ?
O1A C2A N4A 122.21(14) . . ?
O1A C2A C1A 126.55(14) . . ?
N4A C2A C1A 111.23(12) . . ?
O2A C4A N4A 121.11(14) . . ?
O2A C4A N3A 121.98(14) . . ?
N3A C4A N4A 116.91(13) . . ?
C5B C4B H4BA 108.7 . . ?
C5B C4B H4BB 108.7 . . ?
C5B C4B C3B 114.26(13) . . ?
H4BA C4B H4BB 107.6 . . ?
C3B C4B H4BA 108.7 . . ?
C3B C4B H4BB 108.7 . . ?
O1B C1B O2B 121.71(15) . . ?
O1B C1B C2B 124.86(15) . . ?
O2B C1B C2B 113.43(14) . . ?
N1A C8A H8AA 109.5 . . ?
N1A C8A H8AB 109.5 . . ?
N1A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C4B C3B H3BA 109.1 . . ?
C4B C3B H3BB 109.1 . . ?
H3BA C3B H3BB 107.9 . . ?
C2B C3B C4B 112.29(14) . . ?
C2B C3B H3BA 109.1 . . ?
C2B C3B H3BB 109.1 . . ?
N4A C3A H3AA 109.5 . . ?
N4A C3A H3AB 109.5 . . ?
N4A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
N3A C5A H5AA 109.5 . . ?
N3A C5A H5AB 109.5 . . ?
N3A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C1B C2B C3B 112.35(14) . . ?
C1B C2B H2BA 109.1 . . ?
C1B C2B H2BB 109.1 . . ?
C3B C2B H2BA 109.1 . . ?
C3B C2B H2BB 109.1 . . ?
H2BA C2B H2BB 107.9 . . ?
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
O4B C5B 1.3325(19) . ?
O4B H4B 0.82(2) . ?
O1A C2A 1.2237(19) . ?
O2A C4A 1.2183(19) . ?
O1B C1B 1.211(2) . ?
O2B C1B 1.329(2) . ?
O2B H2B 0.92(2) . ?
O3B C5B 1.2110(19) . ?
N1A C1A 1.3816(19) . ?
N1A C7A 1.3394(19) . ?
N1A C8A 1.4577(19) . ?
N4A C2A 1.406(2) . ?
N4A C4A 1.401(2) . ?
N4A C3A 1.4690(19) . ?
N3A C6A 1.374(2) . ?
N3A C4A 1.381(2) . ?
N3A C5A 1.4590(19) . ?
N2A C6A 1.3599(19) . ?
N2A C7A 1.337(2) . ?
C6A C1A 1.367(2) . ?
C1A C2A 1.427(2) . ?
C7A H7A 0.9500 . ?
C5B C4B 1.495(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C3B 1.527(2) . ?
C1B C2B 1.505(2) . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C2B 1.525(2) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
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
O4B C5B C4B C3B 175.99(14) . . . . ?
O1B C1B C2B C3B -87.3(2) . . . . ?
O2B C1B C2B C3B 92.27(17) . . . . ?
O3B C5B C4B C3B -2.0(2) . . . . ?
N1A C1A C2A O1A -0.7(3) . . . . ?
N1A C1A C2A N4A 179.36(14) . . . . ?
N3A C6A C1A N1A -179.69(12) . . . . ?
N3A C6A C1A C2A 0.1(2) . . . . ?
N2A C6A C1A N1A -0.01(16) . . . . ?
N2A C6A C1A C2A 179.79(13) . . . . ?
C6A N3A C4A O2A -179.92(14) . . . . ?
C6A N3A C4A N4A 0.0(2) . . . . ?
C6A N2A C7A N1A -0.06(16) . . . . ?
C6A C1A C2A O1A 179.56(15) . . . . ?
C6A C1A C2A N4A -0.4(2) . . . . ?
C1A N1A C7A N2A 0.06(17) . . . . ?
C7A N1A C1A C6A -0.03(15) . . . . ?
C7A N1A C1A C2A -179.80(15) . . . . ?
C7A N2A C6A N3A 179.70(14) . . . . ?
C7A N2A C6A C1A 0.04(16) . . . . ?
C5B C4B C3B C2B 74.79(18) . . . . ?
C2A N4A C4A O2A 179.58(14) . . . . ?
C2A N4A C4A N3A -0.3(2) . . . . ?
C4A N4A C2A O1A -179.44(14) . . . . ?
C4A N4A C2A C1A 0.5(2) . . . . ?
C4A N3A C6A N2A -179.53(13) . . . . ?
C4A N3A C6A C1A 0.1(2) . . . . ?
C4B C3B C2B C1B -162.01(14) . . . . ?
C8A N1A C1A C6A 178.82(13) . . . . ?
C8A N1A C1A C2A -1.0(2) . . . . ?
C8A N1A C7A N2A -178.80(13) . . . . ?
C3A N4A C2A O1A -0.1(2) . . . . ?
C3A N4A C2A C1A 179.83(13) . . . . ?
C3A N4A C4A O2A 0.2(2) . . . . ?
C3A N4A C4A N3A -179.67(13) . . . . ?
C5A N3A C6A N2A 4.3(2) . . . . ?
C5A N3A C6A C1A -176.02(14) . . . . ?
C5A N3A C4A O2A -3.8(2) . . . . ?
C5A N3A C4A N4A 176.15(13) . . . . ?
