#------------------------------------------------------------------------------
#$Date: 2022-08-05 01:33:55 +0300 (Fri, 05 Aug 2022) $
#$Revision: 277074 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/52/7245266.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_7245266
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, 4(C10 H8 O2), 4(C8 H12 N2), 2(H2 O)'
_chemical_formula_sum            'C88 H94 N8 O10'
_chemical_formula_weight         1423.71
_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_creation_date             2022-07-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-08 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.7440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.66900(10)
_cell_length_b                   8.65540(10)
_cell_length_c                   24.2320(2)
_cell_measurement_reflns_used    26416
_cell_measurement_temperature    123
_cell_measurement_theta_max      79.4380
_cell_measurement_theta_min      3.9020
_cell_volume                     3749.58(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  21.00   0.50    0.50    --    0.00 -57.00  60.00  102
  2  ω    -80.00  19.00   0.50    0.50    --    0.00 -37.00 120.00  198
  3  ω    -32.00  30.00   0.50    0.50    --    0.00  82.00-120.00  124
  4  ω    -85.00 -16.00   0.50    0.50    --    0.00 -57.00-150.00  138
  5  ω    -16.00  23.00   0.50    0.50    --    0.00  37.00  90.00   78
  6  ω     29.00  89.00   0.50    0.50    --    0.00  37.00  90.00  120
  7  ω     18.00  86.00   0.50    1.46    --  107.20 -61.00 -60.00  136
  8  ω    108.00 197.00   0.50    1.46    --  107.20  15.00  60.00  178
  9  ω     77.00 103.00   0.50    1.46    --  107.20  77.00 -90.00   52
 10  ω     20.00 124.00   0.50    1.46    --  107.20 -61.00 150.00  208
 11  ω     18.00 110.00   0.50    1.46    --  107.20 -15.00  30.00  184
 12  ω     20.00  46.00   0.50    1.46    --  107.20 -82.00  60.00   52
 13  ω     56.00 140.00   0.50    1.46    --  107.20 -82.00  60.00  168
 14  ω     67.00 117.00   0.50    1.46    --  107.20 -82.00-120.00  100
 15  ω     50.00  79.00   0.50    1.46    --  107.20 -82.00 150.00   58
 16  ω     52.00 127.00   0.50    1.46    --  107.20 -30.00  30.00  150
 17  ω     57.00 134.00   0.50    1.46    --  107.20 -82.00   0.00  154
 18  ω     21.00  54.00   0.50    1.46    --  107.20 -82.00   0.00   66
 19  ω    107.00 132.00   0.50    1.46    --  107.20 -61.00 -60.00   50
 20  ω     97.00 123.00   0.50    1.46    --  107.20 -82.00 120.00   52
 21  ω     84.00 110.00   0.50    1.46    --  107.20 -82.00 150.00   52
 22  ω     19.00  44.00   0.50    1.46    --  107.20 -61.00 -30.00   50
 23  ω     65.00 128.00   0.50    1.46    --  107.20 -61.00 -30.00  126
 24  ω     33.00 125.00   0.50    1.46    --  107.20 -45.00 150.00  184
 25  ω     82.00 107.00   0.50    1.46    --  107.20 -82.00  30.00   50
 26  ω     96.00 121.00   0.50    1.46    --  107.20 -82.00-180.00   50
 27  ω     19.00 121.00   0.50    1.46    --  107.20 -82.00 -60.00  204
 28  ω     88.00 130.00   0.50    1.46    --  107.20  30.00  30.00   84
 29  ω    145.00 171.00   0.50    1.46    --  107.20  30.00  30.00   52
 30  ω     97.00 180.00   0.50    1.46    --  107.20  30.00   0.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: 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      -0.0182702000
_diffrn_orient_matrix_UB_12      0.1414434000
_diffrn_orient_matrix_UB_13      -0.0401893000
_diffrn_orient_matrix_UB_21      -0.0104229000
_diffrn_orient_matrix_UB_22      0.0989424000
_diffrn_orient_matrix_UB_23      0.0499679000
_diffrn_orient_matrix_UB_31      0.0835890000
_diffrn_orient_matrix_UB_32      0.0433079000
_diffrn_orient_matrix_UB_33      0.0171768000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            45842
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.810
_diffrn_reflns_theta_min         3.899
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             1516
_exptl_crystal_preparation       SDG
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         8071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0380
_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)+(0.0509P)²+1.2002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7520
_reflns_number_total             8071
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00735e2.cif
_cod_data_source_block           exp_970_am-r-20c
_cod_database_code               7245266
_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.
;
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.826
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C)
;
_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 2.038
_oxdiff_exptl_absorpt_empirical_full_min 0.569
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
O2 O 0.87475(4) 0.92420(9) 0.59149(3) 0.02548(17) Uani 1 1 d . . . . .
O4 O 0.93919(4) -0.09146(10) 0.25237(4) 0.02755(18) Uani 1 1 d . . . . .
O5 O 1.01633(5) 0.15530(10) 0.30325(4) 0.03007(18) Uani 1 1 d . . . . .
O3 O 0.66037(5) 0.26815(10) 0.36831(4) 0.03127(19) Uani 1 1 d . . . . .
O1 O 0.50457(5) 0.87037(11) 0.63579(4) 0.0337(2) Uani 1 1 d . . . . .
N8 N 0.83129(5) 0.68565(10) 0.51497(4) 0.02182(18) Uani 1 1 d . . . . .
N7 N 0.37517(5) 0.38474(11) 0.49381(4) 0.0264(2) Uani 1 1 d . . . . .
N9 N 0.76909(5) 0.45446(11) 0.43834(4) 0.02390(19) Uani 1 1 d . . . . .
N6 N 0.45332(5) 0.61782(11) 0.56370(4) 0.02473(19) Uani 1 1 d . . . . .
C18 C 0.69414(6) 0.95923(11) 0.62548(4) 0.0200(2) Uani 1 1 d . . . . .
C27 C 0.85003(6) 0.03539(12) 0.29148(4) 0.0208(2) Uani 1 1 d . . . . .
C23 C 0.72129(6) -0.05961(12) 0.26443(4) 0.0208(2) Uani 1 1 d . . . . .
C28 C 0.77599(6) 0.04660(11) 0.29575(4) 0.0191(2) Uani 1 1 d . . . . .
C39 C 0.82322(6) 0.54297(12) 0.53412(4) 0.0210(2) Uani 1 1 d . . . . .
C29 C 0.75546(6) 0.15932(12) 0.33096(4) 0.0210(2) Uani 1 1 d . . . . .
C26 C 0.86843(6) -0.07742(12) 0.25812(4) 0.0214(2) Uani 1 1 d . . . . .
C17 C 0.74794(6) 0.90960(12) 0.59793(4) 0.0206(2) Uani 1 1 d . . . . .
C16 C 0.81854(6) 0.97285(12) 0.61353(4) 0.0215(2) Uani 1 1 d . . . . .
C20 C 0.68344(6) 0.16492(13) 0.33482(4) 0.0231(2) Uani 1 1 d . . . . .
C40 C 0.79136(6) 0.42548(12) 0.49519(5) 0.0220(2) Uani 1 1 d . . . . .
C19 C 0.62219(6) 0.88999(12) 0.61318(4) 0.0214(2) Uani 1 1 d . . . . .
C24 C 0.74293(6) -0.17604(13) 0.23138(4) 0.0241(2) Uani 1 1 d . . . . .
C13 C 0.71403(6) 1.07752(12) 0.66806(4) 0.0228(2) Uani 1 1 d . . . . .
C15 C 0.83786(6) 1.09208(12) 0.65518(5) 0.0246(2) Uani 1 1 d . . . . .
C32 C 0.40332(6) 0.36294(13) 0.55073(5) 0.0251(2) Uani 1 1 d . . . . .
C43 C 0.77881(6) 0.59555(13) 0.41920(5) 0.0241(2) Uani 1 1 d . . . . .
C44 C 0.81007(6) 0.71360(12) 0.45810(5) 0.0230(2) Uani 1 1 d . . . . .
C35 C 0.38539(6) 0.52170(13) 0.47142(5) 0.0248(2) Uani 1 1 d . . . . .
C22 C 0.64737(6) -0.04874(13) 0.26900(5) 0.0252(2) Uani 1 1 d . . . . .
C36 C 0.42520(6) 0.63983(13) 0.50668(5) 0.0244(2) Uani 1 1 d . . . . .
C10 C 0.57330(6) 0.93400(13) 0.64305(5) 0.0247(2) Uani 1 1 d . . . . .
C49 C 0.99007(6) 0.51949(12) 0.47020(5) 0.0240(2) Uani 1 1 d . . . . .
C14 C 0.78655(6) 1.14322(13) 0.68138(5) 0.0259(2) Uani 1 1 d . . . . .
C21 C 0.62849(6) 0.06023(14) 0.30315(5) 0.0261(2) Uani 1 1 d . . . . .
C25 C 0.81484(6) -0.18632(12) 0.22845(4) 0.0238(2) Uani 1 1 d . . . . .
C48 C 0.99867(6) 0.67361(13) 0.45279(5) 0.0267(2) Uani 1 1 d . . . . .
C31 C 0.44220(6) 0.48138(13) 0.58634(5) 0.0251(2) Uani 1 1 d . . . . .
C50 C 0.96167(6) 0.40375(13) 0.42768(5) 0.0271(2) Uani 1 1 d . . . . .
C38 C 0.84928(6) 0.51813(13) 0.59811(5) 0.0270(2) Uani 1 1 d . . . . .
H38A H 0.811063 0.555715 0.615327 0.041 Uiso 1 1 calc R U . . .
H38B H 0.896020 0.574804 0.614522 0.041 Uiso 1 1 calc R U . . .
H38C H 0.857756 0.407653 0.606250 0.041 Uiso 1 1 calc R U . . .
C12 C 0.66107(7) 1.12336(13) 0.69668(5) 0.0280(2) Uani 1 1 d . . . . .
C41 C 0.78005(7) 0.26452(13) 0.51394(5) 0.0290(2) Uani 1 1 d . . . . .
C46 C 1.04612(6) 0.75161(13) 0.55316(5) 0.0294(2) Uani 1 1 d . . . . .
C11 C 0.59284(7) 1.05316(14) 0.68497(5) 0.0290(2) Uani 1 1 d . . . . .
C45 C 0.81969(7) 0.87471(14) 0.43854(6) 0.0309(2) Uani 1 1 d . . . . .
C47 C 1.02753(7) 0.78763(13) 0.49658(6) 0.0304(2) Uani 1 1 d . . . . .
C42 C 0.75437(8) 0.62146(16) 0.35522(5) 0.0332(3) Uani 1 1 d . . . . .
C51 C 0.94225(7) 0.44510(15) 0.36934(5) 0.0322(3) Uani 1 1 d . . . . .
C30 C 0.47217(8) 0.46246(17) 0.65045(5) 0.0348(3) Uani 1 1 d . . . . .
C52 C 0.95080(7) 0.59583(16) 0.35272(6) 0.0343(3) Uani 1 1 d . . . . .
C34 C 0.35313(7) 0.54041(16) 0.40744(5) 0.0340(3) Uani 1 1 d . . . . .
C53 C 0.97876(7) 0.70933(14) 0.39378(6) 0.0319(3) Uani 1 1 d . . . . .
C33 C 0.39208(8) 0.20660(15) 0.57361(6) 0.0345(3) Uani 1 1 d . . . . .
C37 C 0.43669(7) 0.79537(15) 0.48348(6) 0.0338(3) Uani 1 1 d . . . . .
H17 H 0.7345(7) 0.8273(16) 0.5693(6) 0.026(3) Uiso 1 1 d . . . . .
H27 H 0.8890(7) 0.1084(16) 0.3127(6) 0.023(3) Uiso 1 1 d . . . . .
H25 H 0.8287(8) -0.2654(17) 0.2054(6) 0.032(4) Uiso 1 1 d . . . . .
H14 H 0.7993(8) 1.2254(17) 0.7108(6) 0.030(3) Uiso 1 1 d . . . . .
H29 H 0.7931(8) 0.2324(16) 0.3529(6) 0.027(3) Uiso 1 1 d . . . . .
H24 H 0.7053(8) -0.2524(17) 0.2116(6) 0.031(3) Uiso 1 1 d . . . . .
H19 H 0.6083(7) 0.8093(16) 0.5840(6) 0.026(3) Uiso 1 1 d . . . . .
H22 H 0.6096(8) -0.1238(17) 0.2466(6) 0.030(3) Uiso 1 1 d . . . . .
H21 H 0.5778(8) 0.0648(17) 0.3068(6) 0.032(4) Uiso 1 1 d . . . . .
H46 H 1.0653(9) 0.8310(19) 0.5822(6) 0.038(4) Uiso 1 1 d . . . . .
H12 H 0.6744(8) 1.2038(18) 0.7259(6) 0.034(4) Uiso 1 1 d . . . . .
H15 H 0.8897(8) 1.1341(17) 0.6647(6) 0.031(4) Uiso 1 1 d . . . . .
H41A H 0.8286(10) 0.214(2) 0.5312(7) 0.047(4) Uiso 1 1 d . . . . .
H47 H 1.0349(9) 0.8951(19) 0.4844(7) 0.039(4) Uiso 1 1 d . . . . .
H41B H 0.7536(9) 0.2633(19) 0.5429(7) 0.044(4) Uiso 1 1 d . . . . .
H11 H 0.5558(9) 1.0829(18) 0.7049(7) 0.040(4) Uiso 1 1 d . . . . .
H51 H 0.9235(9) 0.3636(19) 0.3382(7) 0.041(4) Uiso 1 1 d . . . . .
H45A H 0.8473(10) 0.940(2) 0.4726(8) 0.056(5) Uiso 1 1 d . . . . .
H52 H 0.9377(9) 0.621(2) 0.3108(7) 0.046(4) Uiso 1 1 d . . . . .
H53 H 0.9856(9) 0.8151(19) 0.3824(7) 0.039(4) Uiso 1 1 d . . . . .
H42A H 0.7156(10) 0.701(2) 0.3445(7) 0.049(5) Uiso 1 1 d . . . . .
H2 H 0.8578(10) 0.843(2) 0.5648(8) 0.051(5) Uiso 1 1 d . . . . .
H45B H 0.8491(10) 0.876(2) 0.4110(7) 0.050(5) Uiso 1 1 d . . . . .
H5A H 1.0493(11) 0.144(2) 0.3385(8) 0.056(5) Uiso 1 1 d . . . . .
H34A H 0.3233(10) 0.636(2) 0.3981(7) 0.051(5) Uiso 1 1 d . . . . .
H45C H 0.7709(11) 0.921(2) 0.4191(8) 0.057(5) Uiso 1 1 d . . . . .
H5B H 1.0314(10) 0.239(2) 0.2876(8) 0.057(5) Uiso 1 1 d . . . . .
H33A H 0.3595(11) 0.141(2) 0.5425(8) 0.057(5) Uiso 1 1 d . . . . .
H4 H 0.9681(11) -0.003(2) 0.2694(8) 0.062(5) Uiso 1 1 d . . . . .
H3 H 0.7001(11) 0.323(2) 0.3897(8) 0.054(5) Uiso 1 1 d . . . . .
H30A H 0.4946(11) 0.561(2) 0.6677(8) 0.064(6) Uiso 1 1 d . . . . .
H42B H 0.7964(10) 0.661(2) 0.3425(8) 0.055(5) Uiso 1 1 d . . . . .
H37A H 0.4780(12) 0.852(2) 0.5078(9) 0.070(6) Uiso 1 1 d . . . . .
H1 H 0.4945(10) 0.787(2) 0.6101(8) 0.057(5) Uiso 1 1 d . . . . .
H33B H 0.3686(10) 0.215(2) 0.6047(8) 0.052(5) Uiso 1 1 d . . . . .
H41C H 0.7495(10) 0.207(2) 0.4826(8) 0.057(5) Uiso 1 1 d . . . . .
H33C H 0.4395(11) 0.154(2) 0.5900(8) 0.064(5) Uiso 1 1 d . . . . .
H34B H 0.3203(10) 0.445(2) 0.3902(8) 0.057(5) Uiso 1 1 d . . . . .
H30B H 0.5084(11) 0.379(2) 0.6609(8) 0.059(5) Uiso 1 1 d . . . . .
H37B H 0.4475(11) 0.789(2) 0.4456(9) 0.065(6) Uiso 1 1 d . . . . .
H34C H 0.3911(11) 0.552(2) 0.3880(8) 0.063(5) Uiso 1 1 d . . . . .
H37C H 0.3914(12) 0.856(3) 0.4762(9) 0.074(6) Uiso 1 1 d . . . . .
H30C H 0.4331(11) 0.437(2) 0.6684(8) 0.065(6) Uiso 1 1 d . . . . .
H42C H 0.7340(11) 0.527(3) 0.3343(9) 0.068(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
C16 O2 H2 110.6(11) . . ?
C26 O4 H4 108.9(11) . . ?
H5A O5 H5B 105.9(16) . . ?
C20 O3 H3 109.8(12) . . ?
C10 O1 H1 113.6(11) . . ?
C44 N8 C39 119.44(9) . . ?
C35 N7 C32 118.80(10) . . ?
C43 N9 C40 119.58(9) . . ?
C36 N6 C31 118.97(10) . . ?
C17 C18 C13 119.00(9) . . ?
C19 C18 C17 121.75(9) . . ?
C19 C18 C13 119.21(9) . . ?
C28 C27 H27 120.3(8) . . ?
C26 C27 C28 120.38(9) . . ?
C26 C27 H27 119.3(8) . . ?
C24 C23 C28 118.96(9) . . ?
C24 C23 C22 122.24(10) . . ?
C22 C23 C28 118.76(9) . . ?
C27 C28 C23 118.84(9) . . ?
C27 C28 C29 121.88(9) . . ?
C29 C28 C23 119.27(9) . . ?
N8 C39 C40 120.26(9) . . ?
N8 C39 C38 116.97(9) . . ?
C40 C39 C38 122.76(9) . . ?
C28 C29 H29 119.6(8) . . ?
C20 C29 C28 120.24(10) . . ?
C20 C29 H29 120.1(8) . . ?
O4 C26 C25 116.79(9) . . ?
C27 C26 O4 122.27(9) . . ?
C27 C26 C25 120.94(10) . . ?
C18 C17 H17 118.8(8) . . ?
C16 C17 C18 120.04(9) . . ?
C16 C17 H17 121.1(8) . . ?
O2 C16 C17 123.36(9) . . ?
O2 C16 C15 115.75(9) . . ?
C17 C16 C15 120.88(10) . . ?
O3 C20 C29 123.27(10) . . ?
O3 C20 C21 116.07(9) . . ?
C29 C20 C21 120.66(10) . . ?
N9 C40 C39 120.14(10) . . ?
N9 C40 C41 117.10(10) . . ?
C39 C40 C41 122.76(10) . . ?
C18 C19 H19 119.4(8) . . ?
C10 C19 C18 120.29(10) . . ?
C10 C19 H19 120.3(8) . . ?
C23 C24 H24 118.3(8) . . ?
C25 C24 C23 121.32(10) . . ?
C25 C24 H24 120.3(8) . . ?
C14 C13 C18 119.07(10) . . ?
C14 C13 C12 122.08(10) . . ?
C12 C13 C18 118.84(10) . . ?
C16 C15 H15 117.6(8) . . ?
C14 C15 C16 119.91(10) . . ?
C14 C15 H15 122.5(8) . . ?
N7 C32 C31 120.73(10) . . ?
N7 C32 C33 116.89(11) . . ?
C31 C32 C33 122.37(11) . . ?
N9 C43 C44 120.35(10) . . ?
N9 C43 C42 117.61(10) . . ?
C44 C43 C42 122.03(10) . . ?
N8 C44 C43 120.19(10) . . ?
N8 C44 C45 117.74(10) . . ?
C43 C44 C45 122.06(10) . . ?
N7 C35 C36 120.75(10) . . ?
N7 C35 C34 116.86(10) . . ?
C36 C35 C34 122.38(11) . . ?
C23 C22 H22 117.7(8) . . ?
C21 C22 C23 121.30(10) . . ?
C21 C22 H22 121.0(8) . . ?
N6 C36 C35 120.37(10) . . ?
N6 C36 C37 117.26(10) . . ?
C35 C36 C37 122.36(10) . . ?
O1 C10 C19 124.43(10) . . ?
O1 C10 C11 115.16(10) . . ?
C19 C10 C11 120.41(10) . . ?
C49 C49 C50 120.03(13) 3_766 . ?
C48 C49 C49 120.29(13) . 3_766 ?
C48 C49 C50 119.68(10) . . ?
C13 C14 H14 118.0(8) . . ?
C15 C14 C13 121.05(10) . . ?
C15 C14 H14 121.0(8) . . ?
C20 C21 H21 119.6(9) . . ?
C22 C21 C20 119.76(10) . . ?
C22 C21 H21 120.6(9) . . ?
C26 C25 H25 120.0(9) . . ?
C24 C25 C26 119.51(10) . . ?
C24 C25 H25 120.5(9) . . ?
C49 C48 C47 118.42(11) . . ?
C53 C48 C49 119.29(11) . . ?
C53 C48 C47 122.29(11) . . ?
N6 C31 C32 120.37(10) . . ?
N6 C31 C30 117.60(11) . . ?
C32 C31 C30 122.03(11) . . ?
C49 C50 C46 118.25(10) . 3_766 ?
C51 C50 C49 118.95(11) . . ?
C51 C50 C46 122.80(11) . 3_766 ?
C39 C38 H38A 109.5 . . ?
C39 C38 H38B 109.5 . . ?
C39 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C13 C12 H12 119.2(9) . . ?
C11 C12 C13 120.93(10) . . ?
C11 C12 H12 119.8(9) . . ?
C40 C41 H41A 110.4(10) . . ?
C40 C41 H41B 112.1(10) . . ?
C40 C41 H41C 110.6(11) . . ?
H41A C41 H41B 106.7(13) . . ?
H41A C41 H41C 111.9(15) . . ?
H41B C41 H41C 105.0(14) . . ?
C50 C46 H46 118.3(9) 3_766 . ?
C47 C46 C50 121.43(11) . 3_766 ?
C47 C46 H46 120.3(9) . . ?
C10 C11 H11 117.9(9) . . ?
C12 C11 C10 120.27(10) . . ?
C12 C11 H11 121.8(9) . . ?
C44 C45 H45A 110.0(11) . . ?
C44 C45 H45B 111.6(10) . . ?
C44 C45 H45C 110.4(11) . . ?
H45A C45 H45B 107.2(14) . . ?
H45A C45 H45C 110.5(15) . . ?
H45B C45 H45C 107.0(14) . . ?
C48 C47 H47 118.5(9) . . ?
C46 C47 C48 121.59(11) . . ?
C46 C47 H47 119.9(9) . . ?
C43 C42 H42A 111.1(10) . . ?
C43 C42 H42B 110.1(11) . . ?
C43 C42 H42C 111.5(12) . . ?
H42A C42 H42B 105.5(15) . . ?
H42A C42 H42C 107.8(15) . . ?
H42B C42 H42C 110.7(16) . . ?
C50 C51 H51 120.3(9) . . ?
C52 C51 C50 120.99(12) . . ?
C52 C51 H51 118.6(9) . . ?
C31 C30 H30A 109.3(12) . . ?
C31 C30 H30B 112.0(11) . . ?
C31 C30 H30C 112.4(11) . . ?
H30A C30 H30B 110.5(16) . . ?
H30A C30 H30C 106.5(16) . . ?
H30B C30 H30C 105.9(16) . . ?
C51 C52 C53 120.53(12) . . ?
C51 C52 H52 119.2(10) . . ?
C53 C52 H52 120.2(10) . . ?
C35 C34 H34A 111.0(10) . . ?
C35 C34 H34B 110.0(10) . . ?
C35 C34 H34C 112.5(11) . . ?
H34A C34 H34B 110.3(14) . . ?
H34A C34 H34C 104.2(15) . . ?
H34B C34 H34C 108.6(15) . . ?
C48 C53 H53 118.5(9) . . ?
C52 C53 C48 120.56(11) . . ?
C52 C53 H53 121.0(9) . . ?
C32 C33 H33A 110.6(11) . . ?
C32 C33 H33B 111.2(11) . . ?
C32 C33 H33C 111.5(12) . . ?
H33A C33 H33B 108.1(15) . . ?
H33A C33 H33C 109.2(16) . . ?
H33B C33 H33C 106.1(15) . . ?
C36 C37 H37A 113.8(13) . . ?
C36 C37 H37B 112.6(12) . . ?
C36 C37 H37C 110.0(13) . . ?
H37A C37 H37B 104.7(17) . . ?
H37A C37 H37C 110.2(18) . . ?
H37B C37 H37C 105.1(17) . . ?
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
O2 C16 1.3737(13) . ?
O2 H2 0.943(19) . ?
O4 C26 1.3731(12) . ?
O4 H4 0.96(2) . ?
O5 H5A 0.90(2) . ?
O5 H5B 0.90(2) . ?
O3 C20 1.3578(13) . ?
O3 H3 0.907(19) . ?
O1 C10 1.3603(13) . ?
O1 H1 0.94(2) . ?
N8 C39 1.3429(13) . ?
N8 C44 1.3416(14) . ?
N7 C32 1.3404(15) . ?
N7 C35 1.3400(15) . ?
N9 C40 1.3428(14) . ?
N9 C43 1.3371(14) . ?
N6 C36 1.3427(14) . ?
N6 C31 1.3432(15) . ?
C18 C17 1.4232(14) . ?
C18 C19 1.4218(15) . ?
C18 C13 1.4246(14) . ?
C27 C28 1.4189(14) . ?
C27 C26 1.3730(14) . ?
C27 H27 0.989(13) . ?
C23 C28 1.4204(14) . ?
C23 C24 1.4166(15) . ?
C23 C22 1.4189(15) . ?
C28 C29 1.4195(14) . ?
C39 C40 1.3982(15) . ?
C39 C38 1.5008(14) . ?
C29 C20 1.3753(15) . ?
C29 H29 0.981(14) . ?
C26 C25 1.4113(15) . ?
C17 C16 1.3757(15) . ?
C17 H17 0.976(14) . ?
C16 C15 1.4156(15) . ?
C20 C21 1.4173(15) . ?
C40 C41 1.4991(15) . ?
C19 C10 1.3722(15) . ?
C19 H19 0.974(14) . ?
C24 C25 1.3674(15) . ?
C24 H24 0.982(15) . ?
C13 C14 1.4174(15) . ?
C13 C12 1.4182(15) . ?
C15 C14 1.3663(16) . ?
C15 H15 0.997(15) . ?
C32 C31 1.4005(16) . ?
C32 C33 1.4999(16) . ?
C43 C44 1.3988(16) . ?
C43 C42 1.5015(15) . ?
C44 C45 1.5001(15) . ?
C35 C36 1.4007(16) . ?
C35 C34 1.5015(16) . ?
C22 C21 1.3664(16) . ?
C22 H22 0.997(14) . ?
C36 C37 1.4979(16) . ?
C10 C11 1.4195(16) . ?
C49 C49 1.424(2) 3_766 ?
C49 C48 1.4221(16) . ?
C49 C50 1.4253(16) . ?
C14 H14 0.986(15) . ?
C21 H21 0.977(15) . ?
C25 H25 0.964(15) . ?
C48 C47 1.4356(17) . ?
C48 C53 1.4043(17) . ?
C31 C30 1.5008(16) . ?
C50 C46 1.4435(16) 3_766 ?
C50 C51 1.4011(17) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C12 C11 1.3653(17) . ?
C12 H12 0.973(15) . ?
C41 H41A 0.984(17) . ?
C41 H41B 0.969(17) . ?
C41 H41C 0.950(19) . ?
C46 C47 1.3502(18) . ?
C46 H46 0.975(16) . ?
C11 H11 0.984(16) . ?
C45 H45A 1.011(19) . ?
C45 H45B 0.980(18) . ?
C45 H45C 0.981(19) . ?
C47 H47 0.998(17) . ?
C42 H42A 0.981(18) . ?
C42 H42B 0.984(19) . ?
C42 H42C 0.98(2) . ?
C51 C52 1.3881(18) . ?
C51 H51 1.019(16) . ?
C30 H30A 0.98(2) . ?
C30 H30B 0.97(2) . ?
C30 H30C 0.98(2) . ?
C52 C53 1.3886(19) . ?
C52 H52 0.999(17) . ?
C34 H34A 0.989(19) . ?
C34 H34B 1.044(19) . ?
C34 H34C 0.96(2) . ?
C53 H53 0.974(16) . ?
C33 H33A 1.00(2) . ?
C33 H33B 0.977(18) . ?
C33 H33C 0.97(2) . ?
C37 H37A 0.96(2) . ?
C37 H37B 1.00(2) . ?
C37 H37C 0.96(2) . ?
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
O2 H2 N8 0.943(19) 1.795(19) 2.7373(12) 176.5(16) . yes
O5 H5A O2 0.90(2) 1.96(2) 2.8506(12) 167.4(18) 3_766 yes
O5 H5B O4 0.90(2) 1.93(2) 2.8206(12) 174.9(17) 2_755 yes
O4 H4 O5 0.96(2) 1.71(2) 2.6707(12) 176.0(18) . yes
O3 H3 N9 0.907(19) 1.86(2) 2.7596(13) 169.8(17) . yes
O1 H1 N6 0.94(2) 1.87(2) 2.7897(13) 166.4(17) . 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
O2 C16 C15 C14 -177.12(10) . . . . ?
O4 C26 C25 C24 -178.43(10) . . . . ?
O3 C20 C21 C22 -179.13(10) . . . . ?
O1 C10 C11 C12 178.75(11) . . . . ?
N8 C39 C40 N9 0.44(15) . . . . ?
N8 C39 C40 C41 -179.27(10) . . . . ?
N7 C32 C31 N6 -1.50(16) . . . . ?
N7 C32 C31 C30 177.91(10) . . . . ?
N7 C35 C36 N6 -0.50(15) . . . . ?
N7 C35 C36 C37 -178.91(10) . . . . ?
N9 C43 C44 N8 0.70(16) . . . . ?
N9 C43 C44 C45 -178.02(10) . . . . ?
C18 C17 C16 O2 175.83(9) . . . . ?
C18 C17 C16 C15 -2.67(15) . . . . ?
C18 C19 C10 O1 -177.44(10) . . . . ?
C18 C19 C10 C11 2.42(16) . . . . ?
C18 C13 C14 C15 -1.72(16) . . . . ?
C18 C13 C12 C11 1.70(17) . . . . ?
C27 C28 C29 C20 -178.83(10) . . . . ?
C27 C26 C25 C24 2.29(16) . . . . ?
C23 C28 C29 C20 0.29(15) . . . . ?
C23 C24 C25 C26 -1.07(16) . . . . ?
C23 C22 C21 C20 -0.02(17) . . . . ?
C28 C27 C26 O4 179.38(9) . . . . ?
C28 C27 C26 C25 -1.38(15) . . . . ?
C28 C23 C24 C25 -1.01(16) . . . . ?
C28 C23 C22 C21 -0.65(16) . . . . ?
C28 C29 C20 O3 178.99(10) . . . . ?
C28 C29 C20 C21 -0.98(16) . . . . ?
C39 N8 C44 C43 0.93(15) . . . . ?
C39 N8 C44 C45 179.70(9) . . . . ?
C29 C20 C21 C22 0.85(17) . . . . ?
C26 C27 C28 C23 -0.72(15) . . . . ?
C26 C27 C28 C29 178.41(9) . . . . ?
C17 C18 C19 C10 175.98(10) . . . . ?
C17 C18 C13 C14 0.53(15) . . . . ?
C17 C18 C13 C12 -178.09(10) . . . . ?
C17 C16 C15 C14 1.49(16) . . . . ?
C16 C15 C14 C13 0.74(17) . . . . ?
C40 N9 C43 C44 -1.75(15) . . . . ?
C40 N9 C43 C42 178.83(10) . . . . ?
C19 C18 C17 C16 -176.00(9) . . . . ?
C19 C18 C13 C14 178.23(10) . . . . ?
C19 C18 C13 C12 -0.40(15) . . . . ?
C19 C10 C11 C12 -1.13(18) . . . . ?
C24 C23 C28 C27 1.89(14) . . . . ?
C24 C23 C28 C29 -177.26(9) . . . . ?
C24 C23 C22 C21 177.05(10) . . . . ?
C13 C18 C17 C16 1.64(15) . . . . ?
C13 C18 C19 C10 -1.65(15) . . . . ?
C13 C12 C11 C10 -0.96(18) . . . . ?
C32 N7 C35 C36 0.44(15) . . . . ?
C32 N7 C35 C34 179.74(10) . . . . ?
C43 N9 C40 C39 1.19(15) . . . . ?
C43 N9 C40 C41 -179.08(10) . . . . ?
C44 N8 C39 C40 -1.48(14) . . . . ?
C44 N8 C39 C38 178.89(9) . . . . ?
C35 N7 C32 C31 0.53(15) . . . . ?
C35 N7 C32 C33 -178.57(10) . . . . ?
C22 C23 C28 C27 179.67(9) . . . . ?
C22 C23 C28 C29 0.51(14) . . . . ?
C22 C23 C24 C25 -178.70(10) . . . . ?
C36 N6 C31 C32 1.42(15) . . . . ?
C36 N6 C31 C30 -178.02(10) . . . . ?
C49 C49 C48 C47 -0.13(18) 3_766 . . . ?
C49 C49 C48 C53 179.95(12) 3_766 . . . ?
C49 C49 C50 C46 0.02(18) 3_766 . . 3_766 ?
C49 C49 C50 C51 179.76(12) 3_766 . . . ?
C49 C48 C47 C46 -0.21(17) . . . . ?
C49 C48 C53 C52 0.13(17) . . . . ?
C49 C50 C51 C52 0.44(17) . . . . ?
C14 C13 C12 C11 -176.88(11) . . . . ?
C48 C49 C50 C46 179.79(10) . . . 3_766 ?
C48 C49 C50 C51 -0.47(16) . . . . ?
C31 N6 C36 C35 -0.46(15) . . . . ?
C31 N6 C36 C37 178.03(10) . . . . ?
C50 C49 C48 C47 -179.90(10) . . . . ?
C50 C49 C48 C53 0.18(16) . . . . ?
C50 C46 C47 C48 0.43(18) 3_766 . . . ?
C50 C51 C52 C53 -0.13(19) . . . . ?
C38 C39 C40 N9 -179.96(9) . . . . ?
C38 C39 C40 C41 0.33(16) . . . . ?
C12 C13 C14 C15 176.86(11) . . . . ?
C46 C50 C51 C52 -179.82(11) 3_766 . . . ?
C47 C48 C53 C52 -179.78(11) . . . . ?
C42 C43 C44 N8 -179.91(10) . . . . ?
C42 C43 C44 C45 1.37(17) . . . . ?
C51 C52 C53 C48 -0.16(18) . . . . ?
C34 C35 C36 N6 -179.76(10) . . . . ?
C34 C35 C36 C37 1.84(16) . . . . ?
C53 C48 C47 C46 179.71(11) . . . . ?
C33 C32 C31 N6 177.55(10) . . . . ?
C33 C32 C31 C30 -3.03(17) . . . . ?
