#------------------------------------------------------------------------------
#$Date: 2020-06-03 04:53:35 +0200 (Wed 03 de Jun de 2020) $
#$Revision: 252561 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/05/7240594.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_7240594
loop_
_publ_author_name
'Poirier, Marion'
'Pujol-Giménez, Jonai'
'Manatschal, Cristina'
'Bühlmann, Sven'
'Embaby, Ahmed'
'Javor, Sacha'
'Hediger, Matthias A.'
'Reymond, Jean-Louis'
_publ_section_title
;
 Pyrazolyl-pyrimidones inhibit the function of human solute carrier
 protein SLC11A2 (hDMT1) by metal chelation
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D0MD00085J
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'Cl, C10 H13 N4 O2, H2 O'
_chemical_formula_sum            'C10 H15 Cl N4 O3'
_chemical_formula_weight         274.71
_chemical_name_systematic
6-ethyl-4-hydroxy-2-(3-methyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)pyrimidin-1-ium
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-10 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.8062(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.66205(5)
_cell_length_b                   14.39226(6)
_cell_length_c                   9.94738(4)
_cell_measurement_reflns_used    36763
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      77.0270
_cell_measurement_theta_min      4.4440
_cell_volume                     1239.982(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  54.00   0.50    0.20    --  -18.75  45.00 -30.00  170
  2  ω      8.00  35.00   0.50    0.20    --   38.00  93.00  57.22   54
  3  ω      4.00  35.00   0.50    0.20    --   34.00  93.00 117.01   62
  4  ω     27.00 122.00   0.50    0.20    --   50.00  78.00 140.63  190
  5  ω     81.00 167.00   0.50    0.40    --   94.00  49.00  97.72  172
  6  ω    104.00 171.00   0.50    0.40    --  107.11 109.00 124.00  134
  7  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 120.00  160
  8  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 -30.00  160
  9  ω     91.00 171.00   0.50    0.40    --  107.11  61.00  30.00  160
 10  ω     95.00 171.00   0.50    0.40    --  107.11  45.00   0.00  152
 11  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 150.00  160
 12  ω     95.00 171.00   0.50    0.40    --  107.11 125.00  30.00  152
 13  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 -60.00  160
 14  ω     90.00 171.00   0.50    0.40    --  107.11  63.00-140.79  162
 15  ω     91.00 171.00   0.50    0.40    --  107.11  61.00 -90.00  160
 16  ω     85.00 171.00   0.50    0.40    --  107.11  77.00  90.00  172
 17  ω     85.00 171.00   0.50    0.40    --  107.11  77.00 -60.00  172
 18  ω     85.00 171.00   0.50    0.40    --  107.11  77.00-180.00  172
 19  ω     85.00 171.00   0.50    0.40    --  107.11  77.00   0.00  172
 20  ω     85.00 171.00   0.50    0.40    --  107.11  77.00  30.00  172
 21  ω     85.00 171.00   0.50    0.40    --  107.11  77.00 120.00  172
 22  ω     64.00 154.00   0.50    0.40    --   82.00  66.00 113.84  180
 23  ω     71.00 159.00   0.50    0.40    --   86.00  57.00  85.17  176
 24  ω     68.00 159.00   0.50    0.40    --   86.00  67.00-106.51  182
 25  ω     66.00 159.00   0.50    0.40    --   86.00  72.00-166.24  186
 26  ω     71.00 159.00   0.50    0.40    --   86.00  57.00-125.37  176
 27  ω     64.00 159.00   0.50    0.40    --   86.00  76.00   2.34  190
 28  ω     74.00 162.00   0.50    0.40    --   90.00  61.00 -58.80  176
 29  ω     57.00 146.00   0.50    0.20    --   74.00  64.00-176.65  178
 30  ω     59.00 151.00   0.50    0.40    --   78.00  69.00 -52.42  184
 31  ω     62.00 154.00   0.50    0.40    --   82.00  72.00 -88.07  184
 32  ω     60.00 154.00   0.50    0.40    --   82.00  76.00 -70.45  188
 33  ω     61.00 154.00   0.50    0.40    --   82.00  73.00  52.23  186
 34  ω     48.00 143.00   0.50    0.20    --   70.00  75.00 100.33  190
 35  ω     51.00 143.00   0.50    0.20    --   70.00  68.00  74.46  184
 36  ω     48.00 143.00   0.50    0.20    --   70.00  75.00 175.91  190
 37  ω     36.00 131.00   0.50    0.20    --   58.00  77.00  74.11  190
 38  ω     53.00 146.00   0.50    0.20    --   74.00  74.00 -61.20  186
 39  ω     40.00 135.00   0.50    0.20    --   62.00  77.00 147.26  190
 40  ω     40.00 135.00   0.50    0.20    --   62.00  75.00  27.42  190
 41  ω     40.00 135.00   0.50    0.20    --   62.00  75.00 -62.85  190
 42  ω     44.00 139.00   0.50    0.20    --   66.00  76.00  46.67  190
 43  ω     44.00 139.00   0.50    0.20    --   66.00  76.00 123.93  190
 44  ω     44.00 139.00   0.50    0.20    --   66.00  75.00 172.98  190
 45  ω     44.00 139.00   0.50    0.20    --   66.00  75.00   1.82  190
 46  ω     47.00 143.00   0.50    0.20    --   70.00  78.00-105.75  192
 47  ω     39.00 135.00   0.50    0.20    --   62.00  79.00-140.31  192
 48  ω     43.00 139.00   0.50    0.20    --   66.00  78.00-108.91  192
 49  ω     34.00 131.00   0.50    0.20    --   58.00  80.00 -32.51  194
 50  ω     42.00 139.00   0.50    0.20    --   66.00  80.00 -25.55  194
 51  ω     35.00  68.00   0.50    0.40    --  107.11 -61.00   0.00   66
 52  ω     35.00 108.00   0.50    0.40    --  107.11-109.00  28.00  146
 53  ω     35.00  96.00   0.50    0.20    --   47.70-125.00 -60.00  122
 54  ω     35.00 112.00   0.50    0.40    --  107.11-125.00 -30.00  154
 55  ω     35.00 112.00   0.50    0.40    --  107.11-125.00-120.00  154
 56  ω     35.00 112.00   0.50    0.40    --  107.11-125.00 -90.00  154
 57  ω     35.00 106.00   0.50    0.40    --  107.11 -94.00 -30.00  142
 58  ω     23.00  87.00   0.50    0.20    --   47.70-109.00  28.00  128
 59  ω     35.00 106.00   0.50    0.40    --  107.11 -94.00 120.00  142
 60  ω     35.00 106.00   0.50    0.40    --  107.11 -94.00  90.00  142
 61  ω     35.00 102.00   0.50    0.40    --  107.11 -77.00 120.00  134
 62  ω     35.00  68.00   0.50    0.40    --  107.11 -61.00  30.00   66
 63  ω     35.00  68.00   0.50    0.40    --  107.11 -61.00  60.00   66
 64  ω     35.00  68.00   0.50    0.40    --  107.11 -61.00 150.00   66
 65  ω     -1.00  82.00   0.50    0.20    --   47.70 -99.00   0.00  166
 66  ω     17.00  43.00   0.50    0.20    --   42.00  83.00  15.12   52
 67  ω     10.00  43.00   0.50    0.20    --   38.00  90.00 -66.64   66
 68  ω     28.00 122.00   0.50    0.20    --   50.00  77.00-139.68  188
 69  ω     31.00 126.00   0.50    0.20    --   54.00  79.00-130.72  190
 70  ω     30.00 126.00   0.50    0.20    --   54.00  80.00 111.97  192
 71  ω     27.00 122.00   0.50    0.20    --   50.00  79.00 179.41  190
 72  ω     -5.00  29.00   0.50    0.20    --   26.00  96.00 -33.82   68
 73  ω    -57.00   0.00   0.50    0.20    --  -18.75 109.00 124.00  114
 74  ω    -90.00  -3.00   0.50    0.20    --  -18.75 -57.00-150.00  174
 75  ω    -90.00  -2.00   0.50    0.20    --  -18.75 -61.00  30.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0330798000
_diffrn_orient_matrix_UB_12      -0.0242020000
_diffrn_orient_matrix_UB_13      -0.1476781000
_diffrn_orient_matrix_UB_21      -0.0472268000
_diffrn_orient_matrix_UB_22      -0.1015539000
_diffrn_orient_matrix_UB_23      0.0261567000
_diffrn_orient_matrix_UB_31      -0.1682360000
_diffrn_orient_matrix_UB_32      0.0237219000
_diffrn_orient_matrix_UB_33      -0.0386779000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            53002
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.972
_diffrn_reflns_theta_min         4.445
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       irregular
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5090
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0242
_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)+(0.0305P)²+0.2736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0604
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                4976
_reflns_number_total             5090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0md00085j3.cif
_cod_data_source_block           19JLR010_MP303A1
_cod_original_cell_volume        1239.982(9)
_cod_database_code               7240594
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C40 H40 N8 O8 Cl8 '
_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.
;
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.602
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O14-H14
 0.82 with sigma of 0.001
 H33B-H33A
 1.44 with sigma of 0.02
 H34B-H34A
 1.44 with sigma of 0.02
 O33-H33B
 0.95 with sigma of 0.02
 H34B-O34
 0.95 with sigma of 0.02
 H33B-H14 \\sim H14-H33A
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C31(H31A,H31B)
3.b Aromatic/amide H refined with riding coordinates:
 N27(H27), N11(H11), N4(H4), N19(H19), C25(H25), C9(H9), C2(H2), C17(H17)
3.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C29(H29A,H29B,
 H29C)
3.d Idealised tetrahedral OH refined as rotating group:
 O30(H30)
;
_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 1.640
_oxdiff_exptl_absorpt_empirical_full_min 0.815
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
Cl2 Cl 0.52257(6) 0.27452(3) 0.94181(5) 0.03063(12) Uani 1 1 d . . . . .
Cl1 Cl 0.08563(6) 0.51723(3) 0.98615(5) 0.03086(12) Uani 1 1 d . . . . .
O14 O 0.4048(2) 0.42974(10) 0.61449(16) 0.0292(3) Uani 1 1 d D . . . .
O12 O 0.3530(2) 0.86685(10) 0.64327(18) 0.0319(4) Uani 1 1 d . . . . .
O28 O 0.8760(2) 0.62239(10) 0.65575(16) 0.0314(4) Uani 1 1 d . . . . .
O30 O 0.88571(19) 0.18567(10) 0.59906(16) 0.0293(3) Uani 1 1 d . . . . .
H30 H 0.8321 0.1750 0.6646 0.044 Uiso 1 1 calc GR . . . .
O34 O 0.7311(2) 0.13271(11) 0.79454(16) 0.0326(4) Uani 1 1 d D . . . .
O33 O 0.2468(2) 0.37427(11) 0.80400(16) 0.0322(4) Uani 1 1 d D . . . .
N23 N 0.8353(2) 0.33124(12) 0.67509(17) 0.0233(4) Uani 1 1 d . . . . .
N7 N 0.3334(2) 0.57520(12) 0.67774(17) 0.0233(4) Uani 1 1 d . . . . .
N27 N 0.9538(2) 0.45797(12) 0.56600(17) 0.0233(4) Uani 1 1 d . . . . .
H27 H 0.9660 0.5172 0.5623 0.028 Uiso 1 1 calc R . . . .
N11 N 0.4469(2) 0.70248(12) 0.56637(17) 0.0240(4) Uani 1 1 d . . . . .
H11 H 0.4541 0.7619 0.5597 0.029 Uiso 1 1 calc R . . . .
N5 N 0.2729(2) 0.72639(12) 0.73458(18) 0.0238(4) Uani 1 1 d . . . . .
N4 N 0.1733(2) 0.69811(13) 0.83284(18) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.1529 0.6416 0.8543 0.031 Uiso 1 1 calc R . . . .
N20 N 0.7876(2) 0.48221(12) 0.74051(17) 0.0238(4) Uani 1 1 d . . . . .
N19 N 0.6931(2) 0.45365(12) 0.84283(18) 0.0260(4) Uani 1 1 d . . . . .
H19 H 0.6738 0.3971 0.8649 0.031 Uiso 1 1 calc R . . . .
C8 C 0.4179(2) 0.51884(15) 0.59896(19) 0.0237(4) Uani 1 1 d . . . . .
C24 C 0.9089(2) 0.27489(15) 0.58915(19) 0.0233(4) Uani 1 1 d . . . . .
C10 C 0.5315(2) 0.64615(14) 0.48369(19) 0.0223(4) Uani 1 1 d . . . . .
C25 C 1.0083(2) 0.30838(14) 0.4882(2) 0.0238(4) Uani 1 1 d . . . . .
H25 H 1.0581 0.2675 0.4309 0.029 Uiso 1 1 calc R . . . .
C9 C 0.5179(3) 0.55282(14) 0.4992(2) 0.0247(4) Uani 1 1 d . . . . .
H9 H 0.5732 0.5121 0.4454 0.030 Uiso 1 1 calc R . . . .
C26 C 1.0291(2) 0.40131(14) 0.4773(2) 0.0227(4) Uani 1 1 d . . . . .
C22 C 0.8605(2) 0.42055(14) 0.6590(2) 0.0221(4) Uani 1 1 d . . . . .
C1 C 0.2737(3) 0.82542(15) 0.7284(2) 0.0256(4) Uani 1 1 d . . . . .
C21 C 0.7946(3) 0.58098(14) 0.7385(2) 0.0254(4) Uani 1 1 d . . . . .
C6 C 0.3526(2) 0.66455(14) 0.6579(2) 0.0222(4) Uani 1 1 d . . . . .
C32 C 1.2365(3) 0.38696(16) 0.3001(2) 0.0318(5) Uani 1 1 d . . . . .
H32A H 1.2895 0.4223 0.2331 0.048 Uiso 1 1 calc GR . . . .
H32B H 1.1809 0.3370 0.2575 0.048 Uiso 1 1 calc GR . . . .
H32C H 1.3102 0.3620 0.3634 0.048 Uiso 1 1 calc GR . . . .
C15 C 0.6295(3) 0.69478(16) 0.3835(2) 0.0274(5) Uani 1 1 d . . . . .
H15A H 0.6883 0.7429 0.4296 0.033 Uiso 1 1 calc R . . . .
H15B H 0.5625 0.7251 0.3181 0.033 Uiso 1 1 calc R . . . .
C16 C 0.7409(3) 0.63255(17) 0.3094(2) 0.0341(5) Uani 1 1 d . . . . .
H16A H 0.7952 0.6684 0.2439 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.6845 0.5837 0.2651 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.8136 0.6061 0.3723 0.051 Uiso 1 1 calc GR . . . .
C31 C 1.1237(3) 0.44963(14) 0.3732(2) 0.0251(4) Uani 1 1 d . . . . .
H31A H 1.1814 0.4994 0.4164 0.030 Uiso 1 1 calc R . . . .
H31B H 1.0544 0.4777 0.3074 0.030 Uiso 1 1 calc R . . . .
C2 C 0.1708(3) 0.85292(14) 0.8287(2) 0.0259(4) Uani 1 1 d . . . . .
H2 H 0.1456 0.9139 0.8504 0.031 Uiso 1 1 calc R . . . .
C17 C 0.6949(3) 0.60870(15) 0.8426(2) 0.0267(4) Uani 1 1 d . . . . .
H17 H 0.6727 0.6696 0.8669 0.032 Uiso 1 1 calc R . . . .
C3 C 0.1136(2) 0.77456(16) 0.88922(19) 0.0247(4) Uani 1 1 d . . . . .
C18 C 0.6366(2) 0.53015(15) 0.90183(19) 0.0246(4) Uani 1 1 d . . . . .
C13 C 0.0021(3) 0.76569(18) 1.0011(2) 0.0312(4) Uani 1 1 d . . . . .
H13A H -0.0259 0.7016 1.0119 0.047 Uiso 1 1 calc GR . . . .
H13B H -0.0886 0.8016 0.9807 0.047 Uiso 1 1 calc GR . . . .
H13C H 0.0490 0.7881 1.0829 0.047 Uiso 1 1 calc GR . . . .
C29 C 0.5247(3) 0.52136(18) 1.0128(2) 0.0312(5) Uani 1 1 d . . . . .
H29A H 0.4220 0.5162 0.9760 0.047 Uiso 1 1 calc GR . . . .
H29B H 0.5312 0.5753 1.0694 0.047 Uiso 1 1 calc GR . . . .
H29C H 0.5485 0.4669 1.0649 0.047 Uiso 1 1 calc GR . . . .
H33A H 0.316(4) 0.341(2) 0.864(3) 0.079(12) Uiso 1 1 d D . . . .
H14 H 0.345(3) 0.412(2) 0.673(3) 0.070(12) Uiso 1 1 d D . . . .
H33B H 0.207(3) 0.4153(18) 0.858(3) 0.048(9) Uiso 1 1 d D . . . .
H34A H 0.778(4) 0.100(2) 0.853(3) 0.059(10) Uiso 1 1 d D . . . .
H34B H 0.664(3) 0.171(2) 0.832(3) 0.063(11) Uiso 1 1 d D . . . .
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'
Cl Cl 0.3639 0.7018 '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_
_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
C8 O14 H14 116(2) . . ?
C24 O30 H30 109.5 . . ?
H34A O34 H34B 111(3) . . ?
H33A O33 H33B 102(2) . . ?
C22 N23 C24 115.56(18) . . ?
C6 N7 C8 115.52(17) . . ?
C26 N27 H27 120.1 . . ?
C22 N27 H27 120.1 . . ?
C22 N27 C26 119.88(17) . . ?
C10 N11 H11 120.0 . . ?
C6 N11 H11 120.0 . . ?
C6 N11 C10 119.95(17) . . ?
N4 N5 C1 109.27(17) . . ?
C6 N5 N4 122.09(17) . . ?
C6 N5 C1 128.64(19) . . ?
N5 N4 H4 126.2 . . ?
C3 N4 N5 107.69(17) . . ?
C3 N4 H4 126.2 . . ?
N19 N20 C21 109.55(17) . . ?
C22 N20 N19 122.03(17) . . ?
C22 N20 C21 128.42(19) . . ?
N20 N19 H19 126.2 . . ?
C18 N19 N20 107.59(17) . . ?
C18 N19 H19 126.2 . . ?
O14 C8 N7 118.43(17) . . ?
O14 C8 C9 118.73(18) . . ?
N7 C8 C9 122.83(19) . . ?
O30 C24 N23 118.11(18) . . ?
O30 C24 C25 118.98(18) . . ?
N23 C24 C25 122.90(19) . . ?
N11 C10 C15 115.86(18) . . ?
C9 C10 N11 117.91(18) . . ?
C9 C10 C15 126.2(2) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 C24 118.44(19) . . ?
C26 C25 H25 120.8 . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.47(19) . . ?
C10 C9 H9 120.8 . . ?
N27 C26 C31 115.94(17) . . ?
C25 C26 N27 118.02(18) . . ?
C25 C26 C31 126.00(19) . . ?
N23 C22 N27 125.19(19) . . ?
N23 C22 N20 119.02(18) . . ?
N27 C22 N20 115.79(18) . . ?
O12 C1 N5 120.6(2) . . ?
O12 C1 C2 135.0(2) . . ?
C2 C1 N5 104.34(19) . . ?
O28 C21 N20 120.9(2) . . ?
O28 C21 C17 135.0(2) . . ?
C17 C21 N20 104.15(19) . . ?
N7 C6 N11 125.30(19) . . ?
N7 C6 N5 119.27(19) . . ?
N11 C6 N5 115.42(18) . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
C10 C15 H15A 108.6 . . ?
C10 C15 H15B 108.6 . . ?
C10 C15 C16 114.80(18) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 C31 C32 114.57(17) . . ?
C26 C31 H31A 108.6 . . ?
C26 C31 H31B 108.6 . . ?
C32 C31 H31A 108.6 . . ?
C32 C31 H31B 108.6 . . ?
H31A C31 H31B 107.6 . . ?
C1 C2 H2 125.8 . . ?
C3 C2 C1 108.44(18) . . ?
C3 C2 H2 125.8 . . ?
C21 C17 H17 125.9 . . ?
C18 C17 C21 108.27(18) . . ?
C18 C17 H17 125.9 . . ?
N4 C3 C2 110.26(17) . . ?
N4 C3 C13 120.0(2) . . ?
C2 C3 C13 129.8(2) . . ?
N19 C18 C17 110.41(17) . . ?
N19 C18 C29 120.1(2) . . ?
C17 C18 C29 129.5(2) . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C18 C29 H29A 109.5 . . ?
C18 C29 H29B 109.5 . . ?
C18 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
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
O14 C8 1.297(3) . ?
O14 H14 0.8202(15) . ?
O12 C1 1.250(3) . ?
O28 C21 1.243(3) . ?
O30 H30 0.8200 . ?
O30 C24 1.304(3) . ?
O34 H34A 0.85(3) . ?
O34 H34B 0.89(2) . ?
O33 H33A 0.97(3) . ?
O33 H33B 0.88(2) . ?
N23 C24 1.345(3) . ?
N23 C22 1.314(3) . ?
N7 C8 1.350(3) . ?
N7 C6 1.312(3) . ?
N27 H27 0.8600 . ?
N27 C26 1.373(3) . ?
N27 C22 1.349(3) . ?
N11 H11 0.8600 . ?
N11 C10 1.374(3) . ?
N11 C6 1.348(3) . ?
N5 N4 1.374(2) . ?
N5 C1 1.427(2) . ?
N5 C6 1.366(3) . ?
N4 H4 0.8600 . ?
N4 C3 1.342(3) . ?
N20 N19 1.378(2) . ?
N20 C22 1.363(3) . ?
N20 C21 1.423(3) . ?
N19 H19 0.8600 . ?
N19 C18 1.343(3) . ?
C8 C9 1.414(3) . ?
C24 C25 1.416(3) . ?
C10 C9 1.357(3) . ?
C10 C15 1.492(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.354(3) . ?
C9 H9 0.9300 . ?
C26 C31 1.501(3) . ?
C1 C2 1.404(3) . ?
C21 C17 1.416(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C32 C31 1.522(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.515(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(3) . ?
C3 C13 1.489(3) . ?
C18 C29 1.485(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
