#------------------------------------------------------------------------------
#$Date: 2022-08-05 01:33:55 +0300 (Fri, 05 Aug 2022) $
#$Revision: 277074 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/52/7245264.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_7245264
loop_
_publ_author_name
'Ahsan, Mollah Rohan'
'Mukherjee, Arijit'
_publ_section_title
;
 Ternary and quaternary cocrystals of 2,7-dihydroxynaphthalene: systematic
 design with a large synthon module
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00735E
_journal_year                    2022
_chemical_formula_moiety
'C16 H10, 2(C13 H9 N), 2(C10 H8 O2), 2(C8 H12 N2)'
_chemical_formula_sum            'C78 H68 N6 O4'
_chemical_formula_weight         1153.38
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-06-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-07 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                91.725(2)
_cell_angle_beta                 104.910(2)
_cell_angle_gamma                102.633(2)
_cell_formula_units_Z            1
_cell_length_a                   9.2111(3)
_cell_length_b                   11.8322(4)
_cell_length_c                   14.3846(4)
_cell_measurement_reflns_used    7563
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.5540
_cell_measurement_theta_min      3.2030
_cell_volume                     1472.07(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      123.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.995
_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    -41.00 -15.00   0.50    1.74    --    0.00 -19.00   0.00   52
  2  ω    -85.00 -51.00   0.50    1.74    --    0.00 -19.00   0.00   68
  3  ω    -39.00  31.00   0.50    1.74    --    0.00 -82.00-150.00  140
  4  ω    -84.00  16.00   0.50    1.74    --    0.00 -57.00 120.00  200
  5  ω    -19.00  46.00   0.50    1.74    --    0.00  40.00  -4.00  130
  6  ω    -67.00 -41.00   0.50    1.74    --    0.00 -82.00-150.00   52
  7  ω     19.00 140.00   0.50    6.97    --  107.20 -82.00  30.00  242
  8  ω     87.00 196.00   0.50    6.97    --  107.20  45.00-180.00  218
  9  ω     32.00  58.00   0.50    6.97    --  107.20 -15.00   0.00   52
 10  ω     77.00 129.00   0.50    6.97    --  107.20 -82.00 120.00  104
 11  ω     85.00 126.00   0.50    6.97    --  107.20 -30.00-180.00   82
 12  ω     21.00 132.00   0.50    6.97    --  107.20 -61.00-120.00  222
 13  ω     20.00  68.00   0.50    6.97    --  107.20 -61.00 120.00   96
 14  ω     75.00 113.00   0.50    6.97    --  107.20 -61.00 120.00   76
 15  ω     20.00  70.00   0.50    6.97    --  107.20 -82.00 120.00  100
 16  ω     19.00 140.00   0.50    6.97    --  107.20 -82.00-120.00  242
 17  ω     80.00 195.00   0.50    6.97    --  107.20  15.00-120.00  230
 18  ω     88.00 116.00   0.50    6.97    --  107.20 -82.00 -30.00   56
 19  ω    102.00 134.00   0.50    6.97    --  107.20 -15.00-150.00   64
 20  ω    139.00 172.00   0.50    6.97    --  107.20  15.00 -30.00   66
 21  ω     26.00  96.00   0.50    6.97    --  107.20 -61.00  30.00  140
 22  ω     91.00 117.00   0.50    6.97    --  107.20 -82.00-180.00   52
 23  ω     27.00  96.00   0.50    6.97    --  107.20 -15.00-150.00  138
 24  ω     88.00 113.00   0.50    6.97    --  107.20 -82.00  60.00   50
 25  ω     73.00 135.00   0.50    6.97    --  107.20 -15.00   0.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1653742000
_diffrn_orient_matrix_UB_12      -0.0712734000
_diffrn_orient_matrix_UB_13      -0.0096162000
_diffrn_orient_matrix_UB_21      0.0659528000
_diffrn_orient_matrix_UB_22      -0.0943872000
_diffrn_orient_matrix_UB_23      0.0564568000
_diffrn_orient_matrix_UB_31      0.0004991000
_diffrn_orient_matrix_UB_32      0.0629729000
_diffrn_orient_matrix_UB_33      0.0954325000
_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  0.0454
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15805
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.493
_diffrn_reflns_theta_min         3.193
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             610
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         5942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0627
_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)+(0.1331P)²+0.1984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.1970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4986
_reflns_number_total             5942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00735e2.cif
_cod_data_source_block           exp_969_am-r-19c-crysalispro
_cod_database_code               7245264
_shelx_shelxl_version_number     2018/3
_publ_section_exptl
;
Any special experimental details
;
_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   0.939
_shelx_estimated_absorpt_t_min   0.884
_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:
 C39(H39), C43(H43)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C36(H36A,H36B,H36C)
;
_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 2.862
_oxdiff_exptl_absorpt_empirical_full_min 0.463
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
O1 O 0.16302(13) 0.56940(9) 0.88959(8) 0.0321(3) Uani 1 1 d . . . . .
H1 H 0.230(3) 0.611(2) 0.8629(16) 0.048(6) Uiso 1 1 d . . . . .
O2 O 0.10020(14) 0.15946(10) 0.48364(9) 0.0368(3) Uani 1 1 d . . . . .
H2 H 0.167(3) 0.212(2) 0.4710(18) 0.057(7) Uiso 1 1 d . . . . .
N3 N 0.38842(14) 0.71686(11) 0.83111(9) 0.0276(3) Uani 1 1 d . . . . .
N4 N 0.33461(15) 0.30060(12) 0.42794(9) 0.0316(3) Uani 1 1 d . . . . .
N5 N 0.57700(15) 0.44950(12) 0.38277(9) 0.0318(3) Uani 1 1 d . . . . .
C6 C 0.10094(16) 0.46797(13) 0.83175(11) 0.0281(3) Uani 1 1 d . . . . .
C7 C -0.02195(17) 0.38995(14) 0.85539(12) 0.0318(3) Uani 1 1 d . . . . .
H7 H -0.047(2) 0.4100(18) 0.9117(15) 0.040(5) Uiso 1 1 d . . . . .
C8 C -0.09224(17) 0.28692(14) 0.80007(12) 0.0324(3) Uani 1 1 d . . . . .
H8 H -0.175(3) 0.2322(19) 0.8179(15) 0.045(5) Uiso 1 1 d . . . . .
C9 C -0.04424(17) 0.25475(13) 0.71968(11) 0.0294(3) Uani 1 1 d . . . . .
C10 C -0.11318(17) 0.14759(13) 0.66179(12) 0.0321(3) Uani 1 1 d . . . . .
H10 H -0.197(2) 0.0950(17) 0.6787(13) 0.031(4) Uiso 1 1 d . . . . .
C11 C -0.06408(17) 0.11836(13) 0.58497(12) 0.0321(3) Uani 1 1 d . . . . .
H11 H -0.107(2) 0.0459(18) 0.5470(14) 0.039(5) Uiso 1 1 d . . . . .
C12 C 0.05840(17) 0.19653(13) 0.56081(11) 0.0296(3) Uani 1 1 d . . . . .
C13 C 0.12807(16) 0.30164(13) 0.61441(11) 0.0284(3) Uani 1 1 d . . . . .
H13 H 0.212(2) 0.3557(16) 0.5969(13) 0.029(4) Uiso 1 1 d . . . . .
C14 C 0.07930(16) 0.33310(12) 0.69562(10) 0.0268(3) Uani 1 1 d . . . . .
C15 C 0.15044(16) 0.43986(12) 0.75359(11) 0.0276(3) Uani 1 1 d . . . . .
H15 H 0.235(2) 0.4919(17) 0.7378(13) 0.031(4) Uiso 1 1 d . . . . .
C16 C 0.53393(17) 0.70065(13) 0.85176(10) 0.0271(3) Uani 1 1 d . . . . .
C17 C 0.56494(19) 0.60083(13) 0.89822(11) 0.0315(3) Uani 1 1 d . . . . .
H17 H 0.478(3) 0.5455(19) 0.9154(15) 0.044(5) Uiso 1 1 d . . . . .
C18 C 0.7104(2) 0.58192(14) 0.92083(12) 0.0349(4) Uani 1 1 d . . . . .
H18 H 0.727(3) 0.513(2) 0.9535(15) 0.048(6) Uiso 1 1 d . . . . .
C19 C 0.83349(19) 0.66116(15) 0.89723(12) 0.0369(4) Uani 1 1 d . . . . .
H19 H 0.930(3) 0.644(2) 0.9117(18) 0.064(7) Uiso 1 1 d . . . . .
C20 C 0.80829(18) 0.75731(15) 0.85309(12) 0.0346(4) Uani 1 1 d . . . . .
H20 H 0.890(3) 0.812(2) 0.8331(15) 0.046(6) Uiso 1 1 d . . . . .
C21 C 0.65788(17) 0.78151(13) 0.82910(11) 0.0294(3) Uani 1 1 d . . . . .
C22 C 0.62581(19) 0.87971(14) 0.78574(12) 0.0322(3) Uani 1 1 d . . . . .
H22 H 0.710(2) 0.9381(18) 0.7661(14) 0.037(5) Uiso 1 1 d . . . . .
C23 C 0.47650(18) 0.89828(13) 0.76442(11) 0.0301(3) Uani 1 1 d . . . . .
C24 C 0.4367(2) 0.99719(15) 0.71955(12) 0.0378(4) Uani 1 1 d . . . . .
H24 H 0.515(3) 1.0582(19) 0.7017(15) 0.042(5) Uiso 1 1 d . . . . .
C25 C 0.2873(2) 1.00871(16) 0.69852(13) 0.0417(4) Uani 1 1 d . . . . .
H25 H 0.261(3) 1.079(2) 0.6668(18) 0.061(7) Uiso 1 1 d . . . . .
C26 C 0.1716(2) 0.92302(16) 0.72091(12) 0.0400(4) Uani 1 1 d . . . . .
H26 H 0.063(3) 0.930(2) 0.7033(16) 0.051(6) Uiso 1 1 d . . . . .
C27 C 0.20490(19) 0.82817(15) 0.76510(12) 0.0343(4) Uani 1 1 d . . . . .
H27 H 0.126(3) 0.7644(19) 0.7843(15) 0.043(5) Uiso 1 1 d . . . . .
C28 C 0.35958(17) 0.81210(13) 0.78836(10) 0.0278(3) Uani 1 1 d . . . . .
C29 C 0.1548(2) 0.42021(17) 0.36457(14) 0.0393(4) Uani 1 1 d . . . . .
H29A H 0.122(3) 0.432(2) 0.296(2) 0.075(8) Uiso 1 1 d . . . . .
H29B H 0.156(3) 0.487(2) 0.4022(19) 0.065(7) Uiso 1 1 d . . . . .
H29C H 0.081(3) 0.352(3) 0.379(2) 0.075(8) Uiso 1 1 d . . . . .
C30 C 0.31339(18) 0.39709(14) 0.38580(11) 0.0309(3) Uani 1 1 d . . . . .
C31 C 0.43713(18) 0.47277(13) 0.36254(10) 0.0305(3) Uani 1 1 d . . . . .
C32 C 0.4177(2) 0.58184(16) 0.31509(13) 0.0390(4) Uani 1 1 d . . . . .
H32A H 0.346(3) 0.562(2) 0.2534(17) 0.054(6) Uiso 1 1 d . . . . .
H32B H 0.384(3) 0.633(2) 0.3546(19) 0.065(7) Uiso 1 1 d . . . . .
H32C H 0.510(3) 0.626(2) 0.3044(19) 0.066(7) Uiso 1 1 d . . . . .
C33 C 0.75562(19) 0.32842(16) 0.44599(13) 0.0387(4) Uani 1 1 d . . . . .
H33A H 0.824652 0.389608 0.422915 0.058 Uiso 1 1 calc R U . . .
H33B H 0.749789 0.252905 0.413514 0.058 Uiso 1 1 calc R U . . .
H33C H 0.795807 0.327262 0.515917 0.058 Uiso 1 1 calc R U . . .
C34 C 0.59730(17) 0.35212(14) 0.42398(11) 0.0308(3) Uani 1 1 d . . . . .
C35 C 0.47437(18) 0.27581(14) 0.44664(11) 0.0310(3) Uani 1 1 d . . . . .
C36 C 0.4918(2) 0.16505(15) 0.49188(13) 0.0399(4) Uani 1 1 d . . . . .
H36A H 0.395485 0.128057 0.506978 0.060 Uiso 1 1 calc R U . . .
H36B H 0.576495 0.182592 0.551430 0.060 Uiso 1 1 calc R U . . .
H36C H 0.514679 0.112242 0.446734 0.060 Uiso 1 1 calc R U . . .
C37 C 0.51740(19) 0.94929(13) 1.02161(11) 0.0334(4) Uani 1 1 d . . . . .
C38 C 0.3955(2) 0.86222(15) 1.04026(12) 0.0381(4) Uani 1 1 d . . . . .
C39 C 0.4310(2) 0.76479(15) 1.08266(13) 0.0426(4) Uani 1 1 d . . . . .
H39 H 0.350679 0.706652 1.094863 0.051 Uiso 1 1 calc R U . . .
C40 C 0.5809(3) 0.74997(16) 1.10777(13) 0.0458(5) Uani 1 1 d . . . . .
H40 H 0.593(3) 0.668(2) 1.1409(19) 0.065(7) Uiso 1 1 d . . . . .
C41 C 0.6997(2) 0.83232(17) 1.09016(13) 0.0449(4) Uani 1 1 d . . . . .
H41 H 0.799(3) 0.8211(19) 1.1055(15) 0.042(5) Uiso 1 1 d . . . . .
C42 C 0.6699(2) 0.93356(15) 1.04618(12) 0.0386(4) Uani 1 1 d . . . . .
C43 C 0.7890(2) 1.02189(17) 1.02662(13) 0.0434(4) Uani 1 1 d . . . . .
H43 H 0.891894 1.012007 1.042176 0.052 Uiso 1 1 calc R U . . .
C44 C 0.7590(2) 1.11781(16) 0.98705(13) 0.0409(4) Uani 1 1 d . . . . .
H44 H 0.843(3) 1.178(2) 0.9742(17) 0.058(6) 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_
_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 O1 H1 106.0(15) . . ?
C12 O2 H2 109.9(17) . . ?
C28 N3 C16 118.83(13) . . ?
C30 N4 C35 119.45(14) . . ?
C31 N5 C34 119.12(14) . . ?
O1 C6 C7 116.35(14) . . ?
O1 C6 C15 123.57(14) . . ?
C15 C6 C7 120.08(14) . . ?
C6 C7 H7 117.2(13) . . ?
C8 C7 C6 120.04(15) . . ?
C8 C7 H7 122.6(13) . . ?
C7 C8 H8 119.7(12) . . ?
C7 C8 C9 121.54(15) . . ?
C9 C8 H8 118.7(12) . . ?
C8 C9 C10 122.87(14) . . ?
C8 C9 C14 118.57(14) . . ?
C10 C9 C14 118.56(14) . . ?
C9 C10 H10 117.9(11) . . ?
C11 C10 C9 121.70(14) . . ?
C11 C10 H10 120.4(11) . . ?
C10 C11 H11 122.6(12) . . ?
C10 C11 C12 119.73(14) . . ?
C12 C11 H11 117.6(12) . . ?
O2 C12 C11 115.49(13) . . ?
O2 C12 C13 123.86(14) . . ?
C13 C12 C11 120.65(14) . . ?
C12 C13 H13 120.2(10) . . ?
C12 C13 C14 120.38(14) . . ?
C14 C13 H13 119.4(10) . . ?
C13 C14 C9 118.98(13) . . ?
C15 C14 C9 119.12(14) . . ?
C15 C14 C13 121.90(14) . . ?
C6 C15 C14 120.64(14) . . ?
C6 C15 H15 120.5(11) . . ?
C14 C15 H15 118.9(11) . . ?
N3 C16 C17 118.84(14) . . ?
N3 C16 C21 122.11(14) . . ?
C17 C16 C21 119.05(14) . . ?
C16 C17 H17 118.7(12) . . ?
C18 C17 C16 120.55(15) . . ?
C18 C17 H17 120.7(12) . . ?
C17 C18 H18 118.2(13) . . ?
C17 C18 C19 120.61(15) . . ?
C19 C18 H18 121.2(13) . . ?
C18 C19 H19 118.2(16) . . ?
C20 C19 C18 120.47(15) . . ?
C20 C19 H19 121.3(16) . . ?
C19 C20 H20 122.7(13) . . ?
C19 C20 C21 120.87(16) . . ?
C21 C20 H20 116.3(13) . . ?
C20 C21 C16 118.44(15) . . ?
C22 C21 C16 118.09(14) . . ?
C22 C21 C20 123.46(15) . . ?
C21 C22 H22 120.5(11) . . ?
C21 C22 C23 120.61(14) . . ?
C23 C22 H22 118.8(11) . . ?
C22 C23 C24 123.07(15) . . ?
C22 C23 C28 117.43(14) . . ?
C24 C23 C28 119.50(15) . . ?
C23 C24 H24 121.4(12) . . ?
C25 C24 C23 120.11(17) . . ?
C25 C24 H24 118.5(12) . . ?
C24 C25 H25 119.0(15) . . ?
C24 C25 C26 120.41(16) . . ?
C26 C25 H25 120.6(15) . . ?
C25 C26 H26 120.4(14) . . ?
C27 C26 C25 121.44(16) . . ?
C27 C26 H26 118.2(14) . . ?
C26 C27 H27 124.6(12) . . ?
C26 C27 C28 120.21(16) . . ?
C28 C27 H27 115.2(12) . . ?
N3 C28 C23 122.92(14) . . ?
N3 C28 C27 118.76(14) . . ?
C23 C28 C27 118.32(14) . . ?
H29A C29 H29B 109(2) . . ?
H29A C29 H29C 109(2) . . ?
H29B C29 H29C 109(2) . . ?
C30 C29 H29A 108.2(17) . . ?
C30 C29 H29B 110.7(16) . . ?
C30 C29 H29C 109.8(16) . . ?
N4 C30 C29 117.67(14) . . ?
N4 C30 C31 120.14(14) . . ?
C31 C30 C29 122.18(15) . . ?
N5 C31 C30 120.53(14) . . ?
N5 C31 C32 117.80(14) . . ?
C30 C31 C32 121.67(14) . . ?
C31 C32 H32A 109.6(14) . . ?
C31 C32 H32B 111.2(16) . . ?
C31 C32 H32C 113.7(16) . . ?
H32A C32 H32B 111(2) . . ?
H32A C32 H32C 106(2) . . ?
H32B C32 H32C 106(2) . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
N5 C34 C33 117.92(14) . . ?
N5 C34 C35 120.70(14) . . ?
C35 C34 C33 121.37(14) . . ?
N4 C35 C34 120.03(14) . . ?
N4 C35 C36 117.58(14) . . ?
C34 C35 C36 122.39(14) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C37 C37 C38 119.4(2) 2_677 . ?
C42 C37 C37 120.9(2) . 2_677 ?
C42 C37 C38 119.61(16) . . ?
C37 C38 C44 117.40(16) . 2_677 ?
C39 C38 C37 118.85(18) . . ?
C39 C38 C44 123.76(17) . 2_677 ?
C38 C39 H39 119.2 . . ?
C38 C39 C40 121.54(18) . . ?
C40 C39 H39 119.2 . . ?
C39 C40 H40 114.3(14) . . ?
C41 C40 C39 120.60(17) . . ?
C41 C40 H40 125.1(14) . . ?
C40 C41 H41 120.3(14) . . ?
C40 C41 C42 120.27(18) . . ?
C42 C41 H41 119.4(14) . . ?
C37 C42 C41 119.12(18) . . ?
C37 C42 C43 118.34(17) . . ?
C41 C42 C43 122.53(18) . . ?
C42 C43 H43 119.2 . . ?
C44 C43 C42 121.60(17) . . ?
C44 C43 H43 119.2 . . ?
C38 C44 H44 117.3(14) 2_677 . ?
C43 C44 C38 122.27(17) . 2_677 ?
C43 C44 H44 120.5(14) . . ?
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
O1 H1 0.88(3) . ?
O1 C6 1.3617(18) . ?
O2 H2 0.84(3) . ?
O2 C12 1.3554(19) . ?
N3 C16 1.3538(19) . ?
N3 C28 1.344(2) . ?
N4 C30 1.337(2) . ?
N4 C35 1.344(2) . ?
N5 C31 1.337(2) . ?
N5 C34 1.339(2) . ?
C6 C7 1.417(2) . ?
C6 C15 1.375(2) . ?
C7 H7 0.94(2) . ?
C7 C8 1.367(2) . ?
C8 H8 0.98(2) . ?
C8 C9 1.410(2) . ?
C9 C10 1.420(2) . ?
C9 C14 1.426(2) . ?
C10 H10 0.97(2) . ?
C10 C11 1.359(2) . ?
C11 H11 0.95(2) . ?
C11 C12 1.419(2) . ?
C12 C13 1.375(2) . ?
C13 H13 0.984(19) . ?
C13 C14 1.422(2) . ?
C14 C15 1.419(2) . ?
C15 H15 0.96(2) . ?
C16 C17 1.421(2) . ?
C16 C21 1.434(2) . ?
C17 H17 1.00(2) . ?
C17 C18 1.365(2) . ?
C18 H18 0.98(2) . ?
C18 C19 1.425(3) . ?
C19 H19 0.93(3) . ?
C19 C20 1.354(2) . ?
C20 H20 0.99(2) . ?
C20 C21 1.433(2) . ?
C21 C22 1.388(2) . ?
C22 H22 1.03(2) . ?
C22 C23 1.398(2) . ?
C23 C24 1.426(2) . ?
C23 C28 1.432(2) . ?
C24 H24 0.99(2) . ?
C24 C25 1.369(3) . ?
C25 H25 1.01(3) . ?
C25 C26 1.411(3) . ?
C26 H26 0.99(2) . ?
C26 C27 1.360(2) . ?
C27 H27 1.03(2) . ?
C27 C28 1.434(2) . ?
C29 H29A 0.98(3) . ?
C29 H29B 0.94(3) . ?
C29 H29C 0.99(3) . ?
C29 C30 1.500(2) . ?
C30 C31 1.407(2) . ?
C31 C32 1.501(2) . ?
C32 H32A 0.95(2) . ?
C32 H32B 0.97(3) . ?
C32 H32C 0.95(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C33 C34 1.501(2) . ?
C34 C35 1.402(2) . ?
C35 C36 1.502(2) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C37 1.428(3) 2_677 ?
C37 C38 1.435(3) . ?
C37 C42 1.412(3) . ?
C38 C39 1.383(3) . ?
C38 C44 1.450(3) 2_677 ?
C39 H39 0.9500 . ?
C39 C40 1.386(3) . ?
C40 H40 1.11(3) . ?
C40 C41 1.379(3) . ?
C41 H41 0.92(2) . ?
C41 C42 1.418(3) . ?
C42 C43 1.432(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.336(3) . ?
C44 H44 0.98(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
_geom_hbond_publ_flag
O1 H1 N3 0.88(3) 1.87(3) 2.7322(17) 168(2) . yes
O2 H2 N4 0.84(3) 1.92(3) 2.7361(19) 166(2) . 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
O1 C6 C7 C8 179.02(13) . . . . ?
O1 C6 C15 C14 -179.25(12) . . . . ?
O2 C12 C13 C14 -178.74(13) . . . . ?
N3 C16 C17 C18 -179.53(13) . . . . ?
N3 C16 C21 C20 -179.71(13) . . . . ?
N3 C16 C21 C22 0.8(2) . . . . ?
N4 C30 C31 N5 -0.4(2) . . . . ?
N4 C30 C31 C32 179.93(13) . . . . ?
N5 C34 C35 N4 -0.7(2) . . . . ?
N5 C34 C35 C36 179.31(14) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
C7 C6 C15 C14 0.2(2) . . . . ?
C7 C8 C9 C10 178.94(14) . . . . ?
C7 C8 C9 C14 -0.8(2) . . . . ?
C8 C9 C10 C11 -179.60(14) . . . . ?
C8 C9 C14 C13 -179.73(13) . . . . ?
C8 C9 C14 C15 0.6(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C9 C14 C15 C6 -0.3(2) . . . . ?
C10 C9 C14 C13 0.5(2) . . . . ?
C10 C9 C14 C15 -179.24(13) . . . . ?
C10 C11 C12 O2 179.47(13) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C9 -0.9(2) . . . . ?
C12 C13 C14 C15 178.82(13) . . . . ?
C13 C14 C15 C6 -179.96(13) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C15 C6 C7 C8 -0.5(2) . . . . ?
C16 N3 C28 C23 -0.7(2) . . . . ?
C16 N3 C28 C27 178.98(12) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C16 C21 C22 C23 -0.4(2) . . . . ?
C17 C16 C21 C20 0.9(2) . . . . ?
C17 C16 C21 C22 -178.56(13) . . . . ?
C17 C18 C19 C20 0.9(2) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C19 C20 C21 C16 -0.8(2) . . . . ?
C19 C20 C21 C22 178.61(14) . . . . ?
C20 C21 C22 C23 -179.85(13) . . . . ?
C21 C16 C17 C18 -0.1(2) . . . . ?
C21 C22 C23 C24 -179.70(14) . . . . ?
C21 C22 C23 C28 -0.5(2) . . . . ?
C22 C23 C24 C25 178.41(15) . . . . ?
C22 C23 C28 N3 1.1(2) . . . . ?
C22 C23 C28 C27 -178.61(13) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C24 C23 C28 N3 -179.69(13) . . . . ?
C24 C23 C28 C27 0.7(2) . . . . ?
C24 C25 C26 C27 1.1(3) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
C26 C27 C28 N3 -179.32(13) . . . . ?
C26 C27 C28 C23 0.3(2) . . . . ?
C28 N3 C16 C17 179.10(12) . . . . ?
C28 N3 C16 C21 -0.3(2) . . . . ?
C28 C23 C24 C25 -0.8(2) . . . . ?
C29 C30 C31 N5 179.83(14) . . . . ?
C29 C30 C31 C32 0.2(2) . . . . ?
C30 N4 C35 C34 1.4(2) . . . . ?
C30 N4 C35 C36 -178.57(13) . . . . ?
C31 N5 C34 C33 -179.91(13) . . . . ?
C31 N5 C34 C35 -0.6(2) . . . . ?
C33 C34 C35 N4 178.58(14) . . . . ?
C33 C34 C35 C36 -1.4(2) . . . . ?
C34 N5 C31 C30 1.2(2) . . . . ?
C34 N5 C31 C32 -179.17(13) . . . . ?
C35 N4 C30 C29 178.88(13) . . . . ?
C35 N4 C30 C31 -0.9(2) . . . . ?
C37 C37 C38 C39 -179.62(17) 2_677 . . . ?
C37 C37 C38 C44 0.5(3) 2_677 . . 2_677 ?
C37 C37 C42 C41 179.16(16) 2_677 . . . ?
C37 C37 C42 C43 0.0(3) 2_677 . . . ?
C37 C38 C39 C40 0.3(3) . . . . ?
C37 C42 C43 C44 0.7(3) . . . . ?
C38 C37 C42 C41 -0.9(2) . . . . ?
C38 C37 C42 C43 179.94(14) . . . . ?
C38 C39 C40 C41 -0.6(3) . . . . ?
C39 C40 C41 C42 0.1(3) . . . . ?
C40 C41 C42 C37 0.6(3) . . . . ?
C40 C41 C42 C43 179.78(16) . . . . ?
C41 C42 C43 C44 -178.52(16) . . . . ?
C42 C37 C38 C39 0.4(2) . . . . ?
C42 C37 C38 C44 -179.52(14) . . . 2_677 ?
C42 C43 C44 C38 -1.2(3) . . . 2_677 ?
C44 C38 C39 C40 -179.76(15) 2_677 . . . ?
