#------------------------------------------------------------------------------
#$Date: 2020-03-17 04:33:52 +0200 (Tue, 17 Mar 2020) $
#$Revision: 249425 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/01/7240141.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_7240141
loop_
_publ_author_name
'Hong, Yuexian'
'Yufit, Dimitrii S.'
'Letzelter, Nathalie'
'Steed, Jonathan W.'
_publ_section_title
;
 Calcium Cyclic Carboxylates as Structural Models for Calcium Carbonate
 Scale Inhibitors
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00243G
_journal_year                    2020
_chemical_formula_moiety         'C12 H9 O2, C4 H8 N5'
_chemical_formula_sum            'C16 H17 N5 O2'
_chemical_formula_weight         311.34
_chemical_melting_point          485.05
_chemical_name_common
'1-Naphthalene acetic acid + 2,4,6-triaminopyrimidine'
_chemical_name_systematic
'1-Naphthalene acetic acid + 2,4,6-triaminopyrimidine'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-02-08
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-03-06 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                104.860(5)
_cell_angle_beta                 93.046(6)
_cell_angle_gamma                112.269(7)
_cell_formula_units_Z            4
_cell_length_a                   11.7424(9)
_cell_length_b                   11.8549(8)
_cell_length_c                   12.7190(7)
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6580
_cell_measurement_theta_min      3.6510
_cell_volume                     1561.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  59.00   1.00    1.00    --   25.57 -57.00 -90.00  104
  2  ω     13.00 109.00   1.00    1.50    --   66.78-111.00-150.00   96
  3  ω     69.00 153.00   1.00    5.00    --  108.00 -43.00 -30.00   84
  4  ω    120.00 175.00   1.00    5.00    --  108.00  21.00-120.00   55
  5  ω    137.00 178.00   1.00    5.00    --  108.00 104.00 -60.00   41
  6  ω    140.00 177.00   1.00    5.00    --  108.00 138.00-150.00   37
  7  ω    103.00 178.00   1.00    5.00    --  108.00 138.00 -90.00   75
  8  ω    135.00 178.00   1.00    5.00    --  108.00  32.00   0.00   43
  9  ω    140.00 166.00   1.00    5.00    --  108.00  21.00  90.00   26
 10  ω    140.00 166.00   1.00    5.00    --  108.00 -32.00 150.00   26
 11  ω     85.00 138.00   1.00    5.00    --  108.00 -65.00   0.00   53
 12  ω     79.00 113.00   1.00    5.00    --  108.00-123.00   6.00   34
 13  ω     43.00  69.00   1.00    5.00    --  108.00 -65.00   0.00   26
 14  ω     31.00 117.00   1.00    5.00    --  108.00 -77.00 -30.00   86
 15  ω     41.00 120.00   1.00    5.00    --  108.00 -65.00-150.00   79
 16  ω     43.00 132.00   1.00    5.00    --  108.00  32.00   0.00   89
 17  ω    100.00 149.00   1.00    1.50    --   66.78 111.00  90.00   49
 18  ω     53.00 133.00   1.00    5.00    --  108.00 -32.00 150.00   80
 19  ω     68.00 116.00   1.00    5.00    --  108.00-111.00 144.11   48
 20  ω     29.00  56.00   1.00    5.00    --  108.00 -43.00 -30.00   27
 21  ω     27.00 101.00   1.00    5.00    --  108.00  21.00-120.00   74
 22  ω     32.00 139.00   1.00    1.50    --   66.78  61.00  30.00  107
 23  ω     71.00 126.00   1.00    1.50    --   66.78 178.00-180.00   55
 24  ω     34.00 142.00   1.00    1.50    --   66.78  61.00  90.00  108
 25  ω     32.00 132.00   1.00    1.50    --   66.78  61.00 150.00  100
 26  ω     28.00 122.00   1.00    5.00    --  108.00  21.00  90.00   94
 27  ω     23.00 118.00   1.00    5.00    --  108.00 -89.00-150.00   95
 28  ω    -13.00  86.00   1.00    1.50    --   66.78 -45.00-180.00   99
 29  ω    -48.00  59.00   1.00    1.00    --   25.57 -77.00-180.00  107
 30  ω    -46.00  55.00   1.00    1.00    --   25.57 -77.00  60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9245
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.797
_diffrn_reflns_theta_max         66.797
_diffrn_reflns_theta_min         3.647
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0606
_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)+(0.0856P)²+0.9406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1849
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4015
_reflns_number_total             5445
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00243g2.cif
_cod_data_source_block           naatap
_cod_original_cell_volume        1561.16(19)
_cod_database_code               7240141
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C30(H30), C14(H14), C18(H18), C25(H25), C1(H1), C24(H24), C3(H3), C23(H23),
 C8(H8), C2(H2), C21(H21), C19(H19), C5(H5), C20(H20), C7(H7), C6(H6)
;
_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
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O3 O 0.2637(2) -0.13513(18) 0.48435(16) 0.0341(5) Uani 1 1 d . . . . .
O1 O 0.4584(2) 0.45501(18) 0.67407(18) 0.0374(5) Uani 1 1 d . . . . .
O2 O 0.46257(19) 0.64481(18) 0.76230(17) 0.0345(5) Uani 1 1 d . . . . .
O4 O 0.3018(2) 0.04113(19) 0.43631(18) 0.0465(6) Uani 1 1 d . . . . .
N2 N 0.6780(2) 0.5493(2) 0.60557(19) 0.0279(5) Uani 1 1 d . . . . .
N7 N 0.4623(2) -0.0010(2) 0.85494(19) 0.0295(5) Uani 1 1 d . . . . .
N6 N 0.4157(2) 0.0189(2) 0.6795(2) 0.0292(5) Uani 1 1 d . . . . .
N1 N 0.8492(2) 0.5102(2) 0.54392(18) 0.0284(5) Uani 1 1 d . . . . .
N9 N 0.4282(2) 0.2051(2) 0.6480(2) 0.0315(5) Uani 1 1 d . . . . .
N5 N 0.6799(3) 0.3504(2) 0.5732(2) 0.0349(6) Uani 1 1 d . . . . .
N10 N 0.3932(3) -0.1743(2) 0.6983(2) 0.0372(6) Uani 1 1 d . . . . .
N3 N 0.6618(3) 0.7417(2) 0.6369(2) 0.0324(5) Uani 1 1 d . . . . .
N8 N 0.5312(3) 0.1733(3) 1.0072(2) 0.0370(6) Uani 1 1 d . . . . .
N4 N 1.0153(3) 0.6705(3) 0.5138(2) 0.0394(6) Uani 1 1 d . . . . .
C29 C 0.4443(2) 0.1475(2) 0.7217(2) 0.0276(5) Uani 1 1 d . . . . .
C13 C 0.7289(3) 0.6738(2) 0.6043(2) 0.0265(5) Uani 1 1 d . . . . .
C32 C 0.4258(3) -0.0503(2) 0.7472(2) 0.0285(6) Uani 1 1 d . . . . .
C16 C 0.7387(3) 0.4723(2) 0.5744(2) 0.0271(6) Uani 1 1 d . . . . .
C12 C 0.4070(3) 0.5268(3) 0.7206(2) 0.0289(6) Uani 1 1 d . . . . .
C15 C 0.9025(3) 0.6349(3) 0.5438(2) 0.0287(6) Uani 1 1 d . . . . .
C31 C 0.4940(2) 0.1275(3) 0.8984(2) 0.0290(6) Uani 1 1 d . . . . .
C30 C 0.4884(3) 0.2046(2) 0.8331(2) 0.0298(6) Uani 1 1 d . . . . .
H30 H 0.513735 0.292126 0.864070 0.036 Uiso 1 1 calc R U . . .
C14 C 0.8435(3) 0.7181(2) 0.5711(2) 0.0290(6) Uani 1 1 d . . . . .
H14 H 0.880297 0.801132 0.566947 0.035 Uiso 1 1 calc R U . . .
C28 C 0.2571(3) -0.0762(3) 0.4153(2) 0.0337(6) Uani 1 1 d . . . . .
C10 C 0.2229(3) 0.5167(3) 0.8219(2) 0.0340(6) Uani 1 1 d . . . . .
C9 C 0.2426(3) 0.4838(3) 0.9195(3) 0.0385(7) Uani 1 1 d . . . . .
C11 C 0.2668(3) 0.4638(3) 0.7194(2) 0.0393(7) Uani 1 1 d . . . . .
H11A H 0.223580 0.472507 0.656806 0.047 Uiso 1 1 calc R U . . .
H11B H 0.243144 0.373213 0.708145 0.047 Uiso 1 1 calc R U . . .
C22 C 0.0449(3) 0.0321(3) 0.1800(3) 0.0414(7) Uani 1 1 d . . . . .
C17 C 0.0661(3) -0.0448(3) 0.2421(3) 0.0406(7) Uani 1 1 d . . . . .
C4 C 0.1994(3) 0.5323(3) 1.0159(3) 0.0485(8) Uani 1 1 d . . . . .
C18 C -0.0159(3) -0.0761(3) 0.3207(3) 0.0485(8) Uani 1 1 d . . . . .
H18 H -0.006474 -0.126943 0.362395 0.058 Uiso 1 1 calc R U . . .
C27 C 0.1923(4) -0.1589(3) 0.2985(3) 0.0458(8) Uani 1 1 d . . . . .
H27A H 0.244948 -0.198766 0.264153 0.055 Uiso 1 1 calc R U . . .
H27B H 0.114895 -0.226396 0.302135 0.055 Uiso 1 1 calc R U . . .
C26 C 0.1636(3) -0.0862(3) 0.2269(3) 0.0414(7) Uani 1 1 d . . . . .
C25 C 0.2335(3) -0.0534(4) 0.1491(3) 0.0495(8) Uani 1 1 d . . . . .
H25 H 0.295824 -0.083230 0.136906 0.059 Uiso 1 1 calc R U . . .
C1 C 0.1630(3) 0.5960(3) 0.8246(3) 0.0497(8) Uani 1 1 d . . . . .
H1 H 0.149289 0.618557 0.761760 0.060 Uiso 1 1 calc R U . . .
C24 C 0.2178(4) 0.0225(4) 0.0859(3) 0.0551(9) Uani 1 1 d . . . . .
H24 H 0.269396 0.043522 0.034635 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1393(4) 0.6129(4) 1.0142(4) 0.0608(11) Uani 1 1 d . . . . .
H3 H 0.111180 0.644905 1.077400 0.073 Uiso 1 1 calc R U . . .
C23 C 0.1242(4) 0.0648(4) 0.1017(3) 0.0585(10) Uani 1 1 d . . . . .
H23 H 0.112498 0.115500 0.060879 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3025(4) 0.4018(5) 0.9241(3) 0.0616(11) Uani 1 1 d . . . . .
H8 H 0.333539 0.370994 0.862468 0.074 Uiso 1 1 calc R U . . .
C2 C 0.1211(4) 0.6452(4) 0.9233(4) 0.0634(11) Uani 1 1 d . . . . .
H2 H 0.081114 0.699635 0.924016 0.076 Uiso 1 1 calc R U . . .
C21 C -0.0510(4) 0.0738(4) 0.1978(3) 0.0629(11) Uani 1 1 d . . . . .
H21 H -0.064758 0.123683 0.157101 0.075 Uiso 1 1 calc R U . . .
C19 C -0.1067(3) -0.0315(4) 0.3339(4) 0.0650(12) Uani 1 1 d . . . . .
H19 H -0.158523 -0.051602 0.385226 0.078 Uiso 1 1 calc R U . . .
C5 C 0.2187(4) 0.4946(5) 1.1116(3) 0.0695(13) Uani 1 1 d . . . . .
H5 H 0.192551 0.526890 1.175937 0.083 Uiso 1 1 calc R U . . .
C20 C -0.1233(4) 0.0428(5) 0.2726(4) 0.0739(13) Uani 1 1 d . . . . .
H20 H -0.186073 0.072178 0.283369 0.089 Uiso 1 1 calc R U . . .
C7 C 0.3164(5) 0.3664(6) 1.0154(4) 0.0863(17) Uani 1 1 d . . . . .
H7 H 0.354606 0.310447 1.014769 0.104 Uiso 1 1 calc R U . . .
C6 C 0.2742(5) 0.4130(6) 1.1099(4) 0.0832(16) Uani 1 1 d . . . . .
H6 H 0.284102 0.388059 1.172214 0.100 Uiso 1 1 calc R U . . .
H3A H 0.599(3) 0.712(3) 0.674(3) 0.025(7) Uiso 1 1 d . . . . .
H4A H 1.060(4) 0.747(4) 0.516(3) 0.043(10) Uiso 1 1 d . . . . .
H10A H 0.377(3) -0.203(3) 0.622(3) 0.029(8) Uiso 1 1 d . . . . .
H10B H 0.401(3) -0.218(3) 0.728(3) 0.026(8) Uiso 1 1 d . . . . .
H5A H 0.719(3) 0.299(4) 0.560(3) 0.043(10) Uiso 1 1 d . . . . .
H9A H 0.427(3) 0.276(4) 0.667(3) 0.043(10) Uiso 1 1 d . . . . .
H3B H 0.684(3) 0.817(4) 0.632(3) 0.042(10) Uiso 1 1 d . . . . .
H2A H 0.606(4) 0.517(4) 0.630(3) 0.041(9) Uiso 1 1 d . . . . .
H8A H 0.532(4) 0.118(4) 1.048(3) 0.050(10) Uiso 1 1 d . . . . .
H6A H 0.375(3) -0.025(3) 0.612(3) 0.038(9) Uiso 1 1 d . . . . .
H9B H 0.389(3) 0.158(4) 0.578(3) 0.041(9) Uiso 1 1 d . . . . .
H8B H 0.551(3) 0.250(3) 1.039(2) 0.022(7) Uiso 1 1 d . . . . .
H4B H 1.051(4) 0.619(4) 0.502(3) 0.044(10) Uiso 1 1 d . . . . .
H5B H 0.613(4) 0.323(3) 0.599(3) 0.038(9) Uiso 1 1 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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 6 0.0558
-1 7 -3 0.0985
1 -7 3 0.0985
6 1 -4 0.0793
-7 2 3 0.0475
-1 1 -8 0.0366
0 4 5 0.0638
1 0 8 0.0476
5 1 -7 0.0633
4 -7 0 0.0997
-5 2 6 0.0459
5 -7 3 0.0959
7 0 0 0.0714
2 -4 -6 0.0748
-5 1 -5 0.0328
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
C13 N2 H2A 122(2) . . ?
C16 N2 C13 120.6(2) . . ?
C16 N2 H2A 117(2) . . ?
C32 N7 C31 116.9(2) . . ?
C29 N6 H6A 122(2) . . ?
C32 N6 C29 120.6(2) . . ?
C32 N6 H6A 116(2) . . ?
C16 N1 C15 116.5(2) . . ?
C29 N9 H9A 122(3) . . ?
C29 N9 H9B 120(2) . . ?
H9A N9 H9B 114(3) . . ?
C16 N5 H5A 120(2) . . ?
C16 N5 H5B 124(2) . . ?
H5A N5 H5B 115(3) . . ?
C32 N10 H10A 118(2) . . ?
C32 N10 H10B 123(3) . . ?
H10A N10 H10B 118(3) . . ?
C13 N3 H3A 119(2) . . ?
C13 N3 H3B 121(2) . . ?
H3A N3 H3B 119(3) . . ?
C31 N8 H8A 120(2) . . ?
C31 N8 H8B 120(2) . . ?
H8A N8 H8B 120(3) . . ?
C15 N4 H4A 124(3) . . ?
C15 N4 H4B 120(3) . . ?
H4A N4 H4B 116(4) . . ?
N9 C29 N6 115.4(2) . . ?
N9 C29 C30 126.5(2) . . ?
C30 C29 N6 118.1(2) . . ?
N2 C13 C14 118.1(2) . . ?
N3 C13 N2 115.9(3) . . ?
N3 C13 C14 126.0(3) . . ?
N7 C32 N6 123.4(2) . . ?
N7 C32 N10 120.8(3) . . ?
N10 C32 N6 115.8(3) . . ?
N1 C16 N2 123.8(2) . . ?
N1 C16 N5 119.5(3) . . ?
N5 C16 N2 116.8(3) . . ?
O1 C12 C11 116.9(3) . . ?
O2 C12 O1 124.2(3) . . ?
O2 C12 C11 118.8(3) . . ?
N1 C15 C14 122.9(3) . . ?
N4 C15 N1 114.8(3) . . ?
N4 C15 C14 122.3(3) . . ?
N7 C31 C30 122.4(2) . . ?
N8 C31 N7 114.9(3) . . ?
N8 C31 C30 122.7(3) . . ?
C29 C30 C31 118.4(2) . . ?
C29 C30 H30 120.8 . . ?
C31 C30 H30 120.8 . . ?
C13 C14 C15 118.1(2) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
O3 C28 C27 116.3(2) . . ?
O4 C28 O3 124.5(3) . . ?
O4 C28 C27 119.2(3) . . ?
C9 C10 C11 120.0(3) . . ?
C1 C10 C9 118.3(3) . . ?
C1 C10 C11 121.7(3) . . ?
C4 C9 C10 120.0(3) . . ?
C8 C9 C10 122.3(3) . . ?
C8 C9 C4 117.7(3) . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 C12 115.1(2) . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C23 C22 C17 118.2(3) . . ?
C21 C22 C17 119.7(3) . . ?
C21 C22 C23 122.1(4) . . ?
C22 C17 C18 116.7(3) . . ?
C26 C17 C22 120.8(3) . . ?
C26 C17 C18 122.5(3) . . ?
C9 C4 C5 118.3(4) . . ?
C3 C4 C9 119.3(4) . . ?
C3 C4 C5 122.3(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C26 C27 C28 113.8(3) . . ?
C26 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
C17 C26 C27 120.8(3) . . ?
C25 C26 C17 117.6(3) . . ?
C25 C26 C27 121.6(3) . . ?
C26 C25 H25 117.8 . . ?
C26 C25 C24 124.4(4) . . ?
C24 C25 H25 117.8 . . ?
C10 C1 H1 119.6 . . ?
C10 C1 C2 120.9(4) . . ?
C2 C1 H1 119.6 . . ?
C25 C24 H24 120.9 . . ?
C23 C24 C25 118.2(3) . . ?
C23 C24 H24 120.9 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.4 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.8(4) . . ?
C24 C23 H23 119.6 . . ?
C9 C8 H8 118.9 . . ?
C7 C8 C9 122.1(4) . . ?
C7 C8 H8 118.9 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.8 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.9(4) . . ?
C20 C21 H21 119.6 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(4) . . ?
C20 C19 H19 119.5 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.4 . . ?
C21 C20 C19 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C6 120.6(5) . . ?
C6 C7 H7 119.7 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
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
O3 C28 1.271(3) . ?
O1 C12 1.267(3) . ?
O2 C12 1.247(3) . ?
O4 C28 1.234(3) . ?
N2 C13 1.372(3) . ?
N2 C16 1.356(3) . ?
N2 H2A 0.89(4) . ?
N7 C32 1.319(4) . ?
N7 C31 1.372(3) . ?
N6 C29 1.377(3) . ?
N6 C32 1.361(4) . ?
N6 H6A 0.88(4) . ?
N1 C16 1.317(4) . ?
N1 C15 1.370(3) . ?
N9 C29 1.337(4) . ?
N9 H9A 0.82(4) . ?
N9 H9B 0.91(4) . ?
N5 C16 1.340(4) . ?
N5 H5A 0.89(4) . ?
N5 H5B 0.85(4) . ?
N10 C32 1.332(4) . ?
N10 H10A 0.92(3) . ?
N10 H10B 0.75(4) . ?
N3 C13 1.336(4) . ?
N3 H3A 0.90(3) . ?
N3 H3B 0.85(4) . ?
N8 C31 1.331(4) . ?
N8 H8A 0.94(4) . ?
N8 H8B 0.83(3) . ?
N4 C15 1.338(4) . ?
N4 H4A 0.85(4) . ?
N4 H4B 0.85(4) . ?
C29 C30 1.377(4) . ?
C13 C14 1.380(4) . ?
C12 C11 1.526(4) . ?
C15 C14 1.393(4) . ?
C31 C30 1.400(4) . ?
C30 H30 0.9300 . ?
C14 H14 0.9300 . ?
C28 C27 1.521(4) . ?
C10 C9 1.425(4) . ?
C10 C11 1.503(4) . ?
C10 C1 1.366(4) . ?
C9 C4 1.420(4) . ?
C9 C8 1.409(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C22 C17 1.428(5) . ?
C22 C23 1.425(5) . ?
C22 C21 1.399(5) . ?
C17 C18 1.444(5) . ?
C17 C26 1.410(4) . ?
C4 C3 1.390(6) . ?
C4 C5 1.435(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.359(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C26 1.508(5) . ?
C26 C25 1.358(5) . ?
C25 H25 0.9300 . ?
C25 C24 1.404(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.437(6) . ?
C24 H24 0.9300 . ?
C24 C23 1.375(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.339(7) . ?
C23 H23 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.353(5) . ?
C2 H2 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.338(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.353(7) . ?
C20 H20 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.388(7) . ?
C6 H6 0.9300 . ?
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
_geom_hbond_publ_flag
N10 H10B O2 0.75(4) 2.13(4) 2.841(3) 158(3) 1_545 yes
N5 H5A O3 0.89(4) 1.97(4) 2.805(3) 157(3) 2_656 yes
N9 H9A O1 0.82(4) 1.99(4) 2.775(3) 161(4) . yes
N3 H3B O4 0.85(4) 2.04(4) 2.849(3) 158(3) 2_666 yes
N2 H2A O1 0.89(4) 1.79(4) 2.686(3) 177(4) . yes
N6 H6A O3 0.88(4) 1.86(4) 2.724(3) 169(3) . yes
N9 H9B O4 0.91(4) 1.91(4) 2.817(3) 173(3) . yes
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 C28 C27 C26 168.0(3) . . . . ?
O1 C12 C11 C10 143.7(3) . . . . ?
O2 C12 C11 C10 -39.4(4) . . . . ?
O4 C28 C27 C26 -13.7(5) . . . . ?
N2 C13 C14 C15 -1.9(4) . . . . ?
N7 C31 C30 C29 2.7(4) . . . . ?
N6 C29 C30 C31 -4.1(4) . . . . ?
N1 C15 C14 C13 3.0(4) . . . . ?
N9 C29 C30 C31 177.4(3) . . . . ?
N3 C13 C14 C15 177.5(3) . . . . ?
N8 C31 C30 C29 -177.6(3) . . . . ?
N4 C15 C14 C13 -178.0(3) . . . . ?
C29 N6 C32 N7 0.2(4) . . . . ?
C29 N6 C32 N10 178.5(3) . . . . ?
C13 N2 C16 N1 1.7(4) . . . . ?
C13 N2 C16 N5 -177.0(3) . . . . ?
C32 N7 C31 N8 -179.5(3) . . . . ?
C32 N7 C31 C30 0.2(4) . . . . ?
C32 N6 C29 N9 -178.5(2) . . . . ?
C32 N6 C29 C30 2.9(4) . . . . ?
C16 N2 C13 N3 -179.8(2) . . . . ?
C16 N2 C13 C14 -0.3(4) . . . . ?
C16 N1 C15 N4 179.2(3) . . . . ?
C16 N1 C15 C14 -1.7(4) . . . . ?
C15 N1 C16 N2 -0.6(4) . . . . ?
C15 N1 C16 N5 178.1(3) . . . . ?
C31 N7 C32 N6 -1.7(4) . . . . ?
C31 N7 C32 N10 -179.9(3) . . . . ?
C28 C27 C26 C17 -73.8(4) . . . . ?
C28 C27 C26 C25 103.2(4) . . . . ?
C10 C9 C4 C3 -0.7(5) . . . . ?
C10 C9 C4 C5 178.6(3) . . . . ?
C10 C9 C8 C7 -177.1(4) . . . . ?
C10 C1 C2 C3 -0.5(6) . . . . ?
C9 C10 C11 C12 -76.3(4) . . . . ?
C9 C10 C1 C2 0.0(5) . . . . ?
C9 C4 C3 C2 0.2(6) . . . . ?
C9 C4 C5 C6 -1.3(6) . . . . ?
C9 C8 C7 C6 -1.6(9) . . . . ?
C11 C10 C9 C4 -179.1(3) . . . . ?
C11 C10 C9 C8 -0.2(5) . . . . ?
C11 C10 C1 C2 179.7(3) . . . . ?
C22 C17 C18 C19 -0.8(5) . . . . ?
C22 C17 C26 C27 175.3(3) . . . . ?
C22 C17 C26 C25 -1.9(5) . . . . ?
C22 C21 C20 C19 -0.5(7) . . . . ?
C17 C22 C23 C24 0.6(5) . . . . ?
C17 C22 C21 C20 0.2(6) . . . . ?
C17 C18 C19 C20 0.6(6) . . . . ?
C17 C26 C25 C24 2.4(5) . . . . ?
C4 C9 C8 C7 1.8(7) . . . . ?
C4 C3 C2 C1 0.4(6) . . . . ?
C4 C5 C6 C7 1.5(8) . . . . ?
C18 C17 C26 C27 -4.1(5) . . . . ?
C18 C17 C26 C25 178.7(3) . . . . ?
C18 C19 C20 C21 0.1(7) . . . . ?
C27 C26 C25 C24 -174.8(3) . . . . ?
C26 C17 C18 C19 178.6(3) . . . . ?
C26 C25 C24 C23 -1.3(6) . . . . ?
C25 C24 C23 C22 -0.2(6) . . . . ?
C1 C10 C9 C4 0.6(4) . . . . ?
C1 C10 C9 C8 179.5(4) . . . . ?
C1 C10 C11 C12 104.0(4) . . . . ?
C3 C4 C5 C6 178.0(4) . . . . ?
C23 C22 C17 C18 180.0(3) . . . . ?
C23 C22 C17 C26 0.5(5) . . . . ?
C23 C22 C21 C20 -179.3(4) . . . . ?
C8 C9 C4 C3 -179.6(4) . . . . ?
C8 C9 C4 C5 -0.3(5) . . . . ?
C8 C7 C6 C5 -0.1(9) . . . . ?
C21 C22 C17 C18 0.5(4) . . . . ?
C21 C22 C17 C26 -178.9(3) . . . . ?
C21 C22 C23 C24 -180.0(4) . . . . ?
C5 C4 C3 C2 -179.1(4) . . . . ?
