#------------------------------------------------------------------------------
#$Date: 2022-08-05 01:33:55 +0300 (Fri, 05 Aug 2022) $
#$Revision: 277074 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/52/7245259.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_7245259
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         'C13 H9 N, 2(C10 H8 O2), 2(C8 H12 N2)'
_chemical_formula_sum            'C49 H49 N5 O4'
_chemical_formula_weight         771.93
_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
_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
;
2022-06-30 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.863(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6173(4)
_cell_length_b                   9.16000(10)
_cell_length_c                   22.6182(3)
_cell_measurement_reflns_used    19322
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      79.1630
_cell_measurement_theta_min      4.5270
_cell_volume                     4030.14(12)
_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      123.00
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  88.00   0.50    3.60    --    0.00  37.00 120.00  146
  2  ω    -32.00  88.00   0.50    3.60    --    0.00  82.00 -60.00  240
  3  ω    -84.00 -35.00   0.50    3.60    --    0.00 -82.00 -60.00   98
  4  ω    -12.00  63.00   0.50    3.60    --    0.00  37.00  60.00  150
  5  ω    -21.00  14.00   0.50    3.60    --    0.00 -57.00-180.00   70
  6  ω    -32.00  29.00   0.50    3.60    --    0.00 -82.00 -60.00  122
  7  ω     84.00 145.00   0.50   14.42    --  107.20  61.00-120.00  122
  8  ω     87.00 127.00   0.50   14.42    --  107.20  45.00   0.00   80
  9  ω     25.00 135.00   0.50   14.42    --  107.20 -82.00  90.00  220
 10  ω     19.00 134.00   0.50   14.42    --  107.20 -15.00 -90.00  230
 11  ω     95.00 124.00   0.50   14.42    --  107.20 -82.00-180.00   58
 12  ω     18.00  69.00   0.50   14.42    --  107.20 -30.00-180.00  102
 13  ω     90.00 127.00   0.50   14.42    --  107.20 -30.00-180.00   74
 14  ω     44.00 136.00   0.50   14.42    --  107.20 -82.00 -60.00  184
 15  ω     23.00 127.00   0.50   14.42    --  107.20 -30.00 -60.00  208
 16  ω     70.00 111.00   0.50   14.42    --  107.20 -82.00   0.00   82
 17  ω     18.00 121.00   0.50   14.42    --  107.20 -61.00 150.00  206
 18  ω     22.00 108.00   0.50   14.42    --  107.20 -61.00  90.00  172
 19  ω     89.00 197.00   0.50   14.42    --  107.20  30.00 -60.00  216
 20  ω     50.00  75.00   0.50   14.42    --  107.20 -82.00  30.00   50
 21  ω     88.00 113.00   0.50   14.42    --  107.20 -82.00  30.00   50
 22  ω     84.00 137.00   0.50   14.42    --  107.20 -82.00 150.00  106
 23  ω    169.00 195.00   0.50   14.42    --  107.20  61.00-120.00   52
 24  ω     83.00 128.00   0.50   14.42    --  107.20 -45.00  90.00   90
 25  ω    165.00 193.00   0.50   14.42    --  107.20  45.00   0.00   56
 26  ω     68.00 139.00   0.50   14.42    --  107.20 -82.00-120.00  142
 27  ω     78.00 127.00   0.50   14.42    --  107.20  82.00  60.00   98
 28  ω     48.00  73.00   0.50   14.42    --  107.20 -82.00 -30.00   50
 29  ω     85.00 110.00   0.50   14.42    --  107.20 -82.00 -30.00   50
 30  ω    146.00 183.00   0.50   14.42    --  107.20  15.00-180.00   74
;
_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      -0.0033748000
_diffrn_orient_matrix_UB_12      -0.1570303000
_diffrn_orient_matrix_UB_13      0.0227381000
_diffrn_orient_matrix_UB_21      -0.0013996000
_diffrn_orient_matrix_UB_22      0.0598452000
_diffrn_orient_matrix_UB_23      0.0630930000
_diffrn_orient_matrix_UB_31      -0.0791052000
_diffrn_orient_matrix_UB_32      0.0057085000
_diffrn_orient_matrix_UB_33      -0.0351344000
_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  0.0870
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            49639
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.008
_diffrn_reflns_theta_min         3.927
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46503
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         8618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0602
_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)+(0.0735P)²+2.2274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7647
_reflns_number_total             8618
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00735e2.cif
_cod_data_source_block           exp_1066-18-c-lsam-2a
_cod_database_code               7245259
_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   0.968
_shelx_estimated_absorpt_t_min   0.882
_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:
 C30(H30A,H30B,H30C), C34(H34A,H34B,H34C), C37(H37A,H37B,H37C)
;
_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 4.989
_oxdiff_exptl_absorpt_empirical_full_min 0.290
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
O1 O 0.33706(7) 0.85397(15) 0.34499(7) 0.0396(3) Uani 1 1 d . . . . .
O2 O 0.68523(7) 0.90512(15) 0.37017(7) 0.0363(3) Uani 1 1 d . . . . .
O3 O 0.74610(7) 1.07344(15) 0.30842(7) 0.0388(3) Uani 1 1 d . . . . .
O4 O 1.08229(7) 0.76061(15) 0.38205(7) 0.0371(3) Uani 1 1 d . . . . .
N5 N 0.38311(8) 0.63172(17) 0.43574(8) 0.0342(3) Uani 1 1 d . . . . .
N6 N 0.43295(8) 0.41198(17) 0.52776(8) 0.0353(4) Uani 1 1 d . . . . .
N7 N 0.73049(8) 0.71910(16) 0.47429(7) 0.0313(3) Uani 1 1 d . . . . .
N8 N 1.06945(8) 0.55097(16) 0.46508(7) 0.0317(3) Uani 1 1 d . . . . .
N9 N 1.11476(9) 0.32718(17) 0.55552(7) 0.0341(3) Uani 1 1 d . . . . .
C10 C 0.38692(9) 0.9138(2) 0.33139(9) 0.0321(4) Uani 1 1 d . . . . .
C11 C 0.36680(10) 1.0356(2) 0.28838(9) 0.0351(4) Uani 1 1 d . . . . .
C12 C 0.41347(10) 1.1025(2) 0.27174(9) 0.0349(4) Uani 1 1 d . . . . .
C13 C 0.48201(9) 1.05129(19) 0.29603(8) 0.0312(4) Uani 1 1 d . . . . .
C14 C 0.53101(10) 1.1165(2) 0.27824(9) 0.0341(4) Uani 1 1 d . . . . .
C15 C 0.59702(10) 1.0664(2) 0.30242(9) 0.0335(4) Uani 1 1 d . . . . .
C16 C 0.61770(9) 0.94763(19) 0.34716(8) 0.0302(4) Uani 1 1 d . . . . .
C17 C 0.57190(10) 0.88068(18) 0.36530(8) 0.0302(4) Uani 1 1 d . . . . .
C18 C 0.50290(9) 0.93064(18) 0.34010(8) 0.0284(4) Uani 1 1 d . . . . .
C19 C 0.45351(10) 0.86286(19) 0.35694(9) 0.0309(4) Uani 1 1 d . . . . .
C20 C 0.80491(9) 1.05928(19) 0.30065(8) 0.0306(4) Uani 1 1 d . . . . .
C21 C 0.81336(10) 1.16233(19) 0.25805(9) 0.0327(4) Uani 1 1 d . . . . .
C22 C 0.87210(10) 1.16109(19) 0.24947(8) 0.0318(4) Uani 1 1 d . . . . .
C23 C 0.92524(9) 1.05849(18) 0.28271(8) 0.0290(4) Uani 1 1 d . . . . .
C24 C 0.98757(10) 1.05874(19) 0.27669(8) 0.0313(4) Uani 1 1 d . . . . .
C25 C 1.03834(10) 0.95980(19) 0.30974(9) 0.0321(4) Uani 1 1 d . . . . .
C26 C 1.02878(9) 0.85424(19) 0.35082(8) 0.0301(4) Uani 1 1 d . . . . .
C27 C 0.96898(10) 0.85009(19) 0.35778(8) 0.0303(4) Uani 1 1 d . . . . .
C28 C 0.91574(9) 0.95338(18) 0.32442(8) 0.0279(4) Uani 1 1 d . . . . .
C29 C 0.85411(10) 0.95554(19) 0.33229(8) 0.0309(4) Uani 1 1 d . . . . .
C30 C 0.40877(11) 0.8194(2) 0.51934(11) 0.0444(5) Uani 1 1 d . . . . .
H30A H 0.456177 0.855287 0.541098 0.067 Uiso 1 1 calc R U . . .
H30B H 0.387379 0.827310 0.549524 0.067 Uiso 1 1 calc R U . . .
H30C H 0.382707 0.878033 0.479989 0.067 Uiso 1 1 calc R U . . .
C31 C 0.40883(10) 0.6626(2) 0.50006(9) 0.0344(4) Uani 1 1 d . . . . .
C32 C 0.43420(10) 0.5510(2) 0.54654(9) 0.0345(4) Uani 1 1 d . . . . .
C33 C 0.46368(13) 0.5799(3) 0.61906(11) 0.0474(5) Uani 1 1 d . . . . .
C34 C 0.40570(12) 0.2242(2) 0.44437(11) 0.0421(5) Uani 1 1 d . . . . .
H34A H 0.358013 0.193143 0.418405 0.063 Uiso 1 1 calc R U . . .
H34B H 0.426810 0.164029 0.484053 0.063 Uiso 1 1 calc R U . . .
H34C H 0.431466 0.212796 0.418171 0.063 Uiso 1 1 calc R U . . .
C35 C 0.40694(10) 0.3814(2) 0.46349(9) 0.0338(4) Uani 1 1 d . . . . .
C36 C 0.38173(10) 0.4926(2) 0.41665(9) 0.0343(4) Uani 1 1 d . . . . .
C37 C 0.35162(11) 0.4638(2) 0.34410(10) 0.0431(5) Uani 1 1 d . . . . .
H37A H 0.382867 0.401217 0.334476 0.065 Uiso 1 1 calc R U . . .
H37B H 0.345210 0.556490 0.320529 0.065 Uiso 1 1 calc R U . . .
H37C H 0.307117 0.414798 0.329948 0.065 Uiso 1 1 calc R U . . .
C38 C 0.75237(9) 0.7670(2) 0.53667(9) 0.0311(4) Uani 1 1 d . . . . .
C39 C 0.74878(10) 0.9195(2) 0.54761(10) 0.0358(4) Uani 1 1 d . . . . .
C40 C 0.76930(11) 0.9718(2) 0.60966(10) 0.0407(4) Uani 1 1 d . . . . .
C41 C 0.79543(11) 0.8761(3) 0.66455(10) 0.0439(5) Uani 1 1 d . . . . .
C42 C 0.80033(11) 0.7299(2) 0.65620(10) 0.0416(5) Uani 1 1 d . . . . .
C43 C 0.77857(10) 0.6708(2) 0.59187(9) 0.0340(4) Uani 1 1 d . . . . .
C44 C 0.78121(10) 0.5217(2) 0.57977(10) 0.0367(4) Uani 1 1 d . . . . .
C45 C 0.75855(9) 0.4710(2) 0.51581(9) 0.0332(4) Uani 1 1 d . . . . .
C46 C 0.75962(11) 0.3199(2) 0.50001(11) 0.0396(4) Uani 1 1 d . . . . .
C47 C 0.73605(11) 0.2765(2) 0.43657(11) 0.0422(5) Uani 1 1 d . . . . .
C48 C 0.71116(11) 0.3801(2) 0.38465(11) 0.0423(5) Uani 1 1 d . . . . .
C49 C 0.71005(11) 0.5252(2) 0.39772(10) 0.0387(4) Uani 1 1 d . . . . .
C50 C 0.73336(9) 0.57495(19) 0.46360(9) 0.0310(4) Uani 1 1 d . . . . .
C51 C 1.09439(12) 0.7356(2) 0.54968(11) 0.0410(5) Uani 1 1 d . . . . .
C52 C 1.09346(9) 0.57932(19) 0.52958(9) 0.0308(4) Uani 1 1 d . . . . .
C53 C 1.11665(10) 0.4659(2) 0.57495(9) 0.0326(4) Uani 1 1 d . . . . .
C54 C 1.14510(14) 0.4908(3) 0.64788(10) 0.0453(5) Uani 1 1 d . . . . .
C55 C 1.08726(13) 0.1422(2) 0.47117(11) 0.0420(5) Uani 1 1 d . . . . .
C56 C 1.08964(10) 0.29884(19) 0.49118(9) 0.0318(4) Uani 1 1 d . . . . .
C57 C 1.06699(9) 0.41186(19) 0.44532(8) 0.0306(4) Uani 1 1 d . . . . .
C58 C 1.03897(13) 0.3851(3) 0.37294(10) 0.0427(5) Uani 1 1 d . . . . .
H25 H 1.0824(11) 0.961(2) 0.3068(10) 0.030(5) Uiso 1 1 d . . . . .
H12 H 0.3988(12) 1.193(2) 0.2391(11) 0.039(6) Uiso 1 1 d . . . . .
H19 H 0.4683(10) 0.780(2) 0.3886(10) 0.026(5) Uiso 1 1 d . . . . .
H46 H 0.7800(14) 0.250(3) 0.5392(14) 0.060(7) Uiso 1 1 d . . . . .
H29 H 0.8483(10) 0.885(2) 0.3627(10) 0.031(5) Uiso 1 1 d . . . . .
H17 H 0.5873(11) 0.799(2) 0.3995(10) 0.033(5) Uiso 1 1 d . . . . .
H21 H 0.7750(11) 1.237(2) 0.2357(11) 0.036(5) Uiso 1 1 d . . . . .
H14 H 0.5163(11) 1.203(2) 0.2466(11) 0.035(5) Uiso 1 1 d . . . . .
H22 H 0.8797(11) 1.235(2) 0.2191(11) 0.039(6) Uiso 1 1 d . . . . .
H58A H 0.9983(12) 0.324(3) 0.3570(11) 0.042(6) Uiso 1 1 d . . . . .
H49 H 0.6911(12) 0.604(3) 0.3594(11) 0.040(6) Uiso 1 1 d . . . . .
H39 H 0.7309(11) 0.986(3) 0.5092(11) 0.038(6) Uiso 1 1 d . . . . .
H33A H 0.4963(15) 0.662(3) 0.6318(14) 0.061(8) Uiso 1 1 d . . . . .
H44 H 0.7993(13) 0.449(3) 0.6160(13) 0.055(7) Uiso 1 1 d . . . . .
H24 H 0.9960(13) 1.135(3) 0.2492(12) 0.049(7) Uiso 1 1 d . . . . .
H51A H 1.1434(15) 0.771(3) 0.5764(14) 0.063(8) Uiso 1 1 d . . . . .
H15 H 0.6306(12) 1.113(3) 0.2886(11) 0.039(6) Uiso 1 1 d . . . . .
H27 H 0.9614(12) 0.775(3) 0.3868(11) 0.043(6) Uiso 1 1 d . . . . .
H42 H 0.8186(12) 0.663(3) 0.6933(12) 0.046(6) Uiso 1 1 d . . . . .
H55A H 1.0396(16) 0.112(3) 0.4427(14) 0.068(8) Uiso 1 1 d . . . . .
H51B H 1.0715(14) 0.751(3) 0.5789(14) 0.058(7) Uiso 1 1 d . . . . .
H54A H 1.1805(17) 0.561(4) 0.6629(16) 0.080(10) Uiso 1 1 d . . . . .
H3 H 0.7407(16) 1.005(4) 0.3346(16) 0.080(10) Uiso 1 1 d . . . . .
H47 H 0.7380(14) 0.170(3) 0.4273(14) 0.062(8) Uiso 1 1 d . . . . .
H48 H 0.6975(14) 0.344(3) 0.3385(14) 0.064(8) Uiso 1 1 d . . . . .
H11 H 0.3178(12) 1.072(3) 0.2715(11) 0.043(6) Uiso 1 1 d . . . . .
H54B H 1.1109(17) 0.528(3) 0.6592(15) 0.074(9) Uiso 1 1 d . . . . .
H51C H 1.0731(16) 0.798(4) 0.5126(16) 0.078(9) Uiso 1 1 d . . . . .
H40 H 0.7657(13) 1.079(3) 0.6165(13) 0.055(7) Uiso 1 1 d . . . . .
H58B H 1.0732(14) 0.336(3) 0.3620(13) 0.059(8) Uiso 1 1 d . . . . .
H41 H 0.8091(13) 0.922(3) 0.7098(13) 0.055(7) Uiso 1 1 d . . . . .
H1 H 0.3564(17) 0.768(4) 0.3771(17) 0.090(11) Uiso 1 1 d . . . . .
H55B H 1.1140(16) 0.122(3) 0.4482(15) 0.070(9) Uiso 1 1 d . . . . .
H33B H 0.4287(17) 0.617(3) 0.6315(15) 0.074(9) Uiso 1 1 d . . . . .
H33C H 0.4853(15) 0.483(4) 0.6440(15) 0.073(9) Uiso 1 1 d . . . . .
H55C H 1.107(2) 0.073(5) 0.508(2) 0.112(13) Uiso 1 1 d . . . . .
H2 H 0.7003(15) 0.839(3) 0.4084(15) 0.068(8) Uiso 1 1 d . . . . .
H58C H 1.0231(16) 0.482(4) 0.3490(15) 0.074(9) Uiso 1 1 d . . . . .
H54C H 1.1637(17) 0.393(4) 0.6729(16) 0.082(10) Uiso 1 1 d . . . . .
H4 H 1.0700(14) 0.704(3) 0.4087(14) 0.062(8) 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
C10 O1 H1 110.6(19) . . ?
C16 O2 H2 113.3(17) . . ?
C20 O3 H3 114(2) . . ?
C26 O4 H4 105.7(18) . . ?
C31 N5 C36 119.30(16) . . ?
C32 N6 C35 118.93(16) . . ?
C50 N7 C38 118.88(15) . . ?
C52 N8 C57 119.02(15) . . ?
C56 N9 C53 118.73(16) . . ?
O1 C10 C11 115.87(17) . . ?
O1 C10 C19 123.75(17) . . ?
C19 C10 C11 120.38(18) . . ?
C10 C11 H11 118.3(13) . . ?
C12 C11 C10 119.96(18) . . ?
C12 C11 H11 121.7(13) . . ?
C11 C12 C13 121.20(17) . . ?
C11 C12 H12 120.6(12) . . ?
C13 C12 H12 118.2(12) . . ?
C12 C13 C14 122.32(16) . . ?
C12 C13 C18 119.16(17) . . ?
C14 C13 C18 118.52(17) . . ?
C13 C14 H14 118.9(12) . . ?
C15 C14 C13 121.58(17) . . ?
C15 C14 H14 119.5(12) . . ?
C14 C15 C16 119.52(18) . . ?
C14 C15 H15 120.2(13) . . ?
C16 C15 H15 120.3(13) . . ?
O2 C16 C15 116.07(16) . . ?
C17 C16 O2 123.10(16) . . ?
C17 C16 C15 120.83(17) . . ?
C16 C17 C18 120.32(16) . . ?
C16 C17 H17 121.0(12) . . ?
C18 C17 H17 118.6(12) . . ?
C17 C18 C13 119.22(17) . . ?
C17 C18 C19 122.08(16) . . ?
C19 C18 C13 118.70(16) . . ?
C10 C19 C18 120.58(16) . . ?
C10 C19 H19 120.6(11) . . ?
C18 C19 H19 118.8(11) . . ?
O3 C20 C21 115.36(16) . . ?
O3 C20 C29 123.57(16) . . ?
C29 C20 C21 121.05(17) . . ?
C20 C21 H21 117.8(12) . . ?
C22 C21 C20 119.66(17) . . ?
C22 C21 H21 122.6(12) . . ?
C21 C22 C23 121.21(16) . . ?
C21 C22 H22 121.4(13) . . ?
C23 C22 H22 117.4(13) . . ?
C22 C23 C28 118.76(17) . . ?
C24 C23 C22 122.26(16) . . ?
C24 C23 C28 118.98(16) . . ?
C23 C24 H24 120.0(14) . . ?
C25 C24 C23 121.22(17) . . ?
C25 C24 H24 118.7(14) . . ?
C24 C25 C26 119.94(18) . . ?
C24 C25 H25 121.8(12) . . ?
C26 C25 H25 118.3(12) . . ?
O4 C26 C25 115.81(17) . . ?
O4 C26 C27 123.57(16) . . ?
C27 C26 C25 120.61(17) . . ?
C26 C27 C28 120.38(16) . . ?
C26 C27 H27 121.4(13) . . ?
C28 C27 H27 118.2(13) . . ?
C23 C28 C27 118.87(17) . . ?
C29 C28 C23 119.23(16) . . ?
C29 C28 C27 121.90(16) . . ?
C20 C29 C28 120.06(16) . . ?
C20 C29 H29 120.7(12) . . ?
C28 C29 H29 119.1(12) . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
N5 C31 C30 117.64(17) . . ?
N5 C31 C32 120.23(17) . . ?
C32 C31 C30 122.12(18) . . ?
N6 C32 C31 120.70(18) . . ?
N6 C32 C33 117.06(18) . . ?
C31 C32 C33 122.24(18) . . ?
C32 C33 H33A 111.3(17) . . ?
C32 C33 H33B 111.3(19) . . ?
C32 C33 H33C 108.4(17) . . ?
H33A C33 H33B 101(2) . . ?
H33A C33 H33C 113(2) . . ?
H33B C33 H33C 111(2) . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C35 C34 H34A 109.5 . . ?
C35 C34 H34B 109.5 . . ?
C35 C34 H34C 109.5 . . ?
N6 C35 C34 117.35(17) . . ?
N6 C35 C36 120.73(17) . . ?
C36 C35 C34 121.92(18) . . ?
N5 C36 C35 120.10(17) . . ?
N5 C36 C37 117.18(17) . . ?
C35 C36 C37 122.72(18) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N7 C38 C39 118.60(16) . . ?
N7 C38 C43 122.48(17) . . ?
C39 C38 C43 118.92(17) . . ?
C38 C39 H39 118.7(13) . . ?
C40 C39 C38 120.35(18) . . ?
C40 C39 H39 120.9(13) . . ?
C39 C40 C41 120.7(2) . . ?
C39 C40 H40 119.4(15) . . ?
C41 C40 H40 119.9(15) . . ?
C40 C41 H41 116.7(15) . . ?
C42 C41 C40 120.7(2) . . ?
C42 C41 H41 122.6(15) . . ?
C41 C42 C43 120.24(19) . . ?
C41 C42 H42 121.7(14) . . ?
C43 C42 H42 118.1(15) . . ?
C42 C43 C38 119.05(18) . . ?
C44 C43 C38 117.78(17) . . ?
C44 C43 C42 123.17(18) . . ?
C43 C44 H44 121.6(15) . . ?
C45 C44 C43 120.27(17) . . ?
C45 C44 H44 118.1(15) . . ?
C44 C45 C46 123.10(17) . . ?
C44 C45 C50 118.19(17) . . ?
C50 C45 C46 118.70(18) . . ?
C45 C46 H46 115.8(15) . . ?
C47 C46 C45 120.52(18) . . ?
C47 C46 H46 123.7(15) . . ?
C46 C47 C48 120.76(19) . . ?
C46 C47 H47 118.5(16) . . ?
C48 C47 H47 120.8(16) . . ?
C47 C48 H48 118.0(16) . . ?
C49 C48 C47 120.5(2) . . ?
C49 C48 H48 121.3(16) . . ?
C48 C49 C50 120.46(19) . . ?
C48 C49 H49 121.5(12) . . ?
C50 C49 H49 118.0(12) . . ?
N7 C50 C45 122.40(17) . . ?
N7 C50 C49 118.56(16) . . ?
C49 C50 C45 119.04(17) . . ?
C52 C51 H51A 111.0(16) . . ?
C52 C51 H51B 113.2(16) . . ?
C52 C51 H51C 112(2) . . ?
H51A C51 H51B 104(2) . . ?
H51A C51 H51C 108(2) . . ?
H51B C51 H51C 108(2) . . ?
N8 C52 C51 117.49(17) . . ?
N8 C52 C53 120.07(16) . . ?
C53 C52 C51 122.44(17) . . ?
N9 C53 C52 121.12(16) . . ?
N9 C53 C54 116.27(17) . . ?
C52 C53 C54 122.62(17) . . ?
C53 C54 H54A 112(2) . . ?
C53 C54 H54B 111.0(19) . . ?
C53 C54 H54C 109.9(18) . . ?
H54A C54 H54B 105(3) . . ?
H54A C54 H54C 110(3) . . ?
H54B C54 H54C 109(3) . . ?
C56 C55 H55A 110.9(17) . . ?
C56 C55 H55B 113.5(19) . . ?
C56 C55 H55C 114(2) . . ?
H55A C55 H55B 108(2) . . ?
H55A C55 H55C 108(3) . . ?
H55B C55 H55C 102(3) . . ?
N9 C56 C55 117.28(17) . . ?
N9 C56 C57 120.61(16) . . ?
C57 C56 C55 122.11(17) . . ?
N8 C57 C56 120.43(16) . . ?
N8 C57 C58 117.20(16) . . ?
C56 C57 C58 122.36(17) . . ?
C57 C58 H58A 111.7(14) . . ?
C57 C58 H58B 111.0(16) . . ?
C57 C58 H58C 108.7(17) . . ?
H58A C58 H58B 108(2) . . ?
H58A C58 H58C 106(2) . . ?
H58B C58 H58C 112(2) . . ?
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 C10 1.359(2) . ?
O1 H1 1.03(4) . ?
O2 C16 1.375(2) . ?
O2 H2 0.99(3) . ?
O3 C20 1.363(2) . ?
O3 H3 0.91(3) . ?
O4 C26 1.364(2) . ?
O4 H4 0.92(3) . ?
N5 C31 1.341(2) . ?
N5 C36 1.342(2) . ?
N6 C32 1.339(2) . ?
N6 C35 1.339(2) . ?
N7 C38 1.351(2) . ?
N7 C50 1.349(2) . ?
N8 C52 1.343(2) . ?
N8 C57 1.344(2) . ?
N9 C53 1.340(2) . ?
N9 C56 1.338(2) . ?
C10 C11 1.419(3) . ?
C10 C19 1.378(3) . ?
C11 C12 1.366(3) . ?
C11 H11 1.01(2) . ?
C12 C13 1.417(3) . ?
C12 H12 1.06(2) . ?
C13 C14 1.419(3) . ?
C13 C18 1.423(2) . ?
C14 C15 1.366(3) . ?
C14 H14 1.02(2) . ?
C15 C16 1.418(2) . ?
C15 H15 1.00(2) . ?
C16 C17 1.371(3) . ?
C17 C18 1.420(3) . ?
C17 H17 1.03(2) . ?
C18 C19 1.423(3) . ?
C19 H19 1.00(2) . ?
C20 C21 1.416(2) . ?
C20 C29 1.372(3) . ?
C21 C22 1.366(3) . ?
C21 H21 1.02(2) . ?
C22 C23 1.419(2) . ?
C22 H22 1.03(2) . ?
C23 C24 1.412(3) . ?
C23 C28 1.424(2) . ?
C24 C25 1.367(3) . ?
C24 H24 1.00(3) . ?
C25 C26 1.417(2) . ?
C25 H25 0.98(2) . ?
C26 C27 1.369(3) . ?
C27 C28 1.425(2) . ?
C27 H27 1.01(2) . ?
C28 C29 1.419(3) . ?
C29 H29 0.99(2) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C30 C31 1.502(3) . ?
C31 C32 1.396(3) . ?
C32 C33 1.502(3) . ?
C33 H33A 0.98(3) . ?
C33 H33B 0.97(3) . ?
C33 H33C 1.05(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C34 C35 1.501(3) . ?
C35 C36 1.397(3) . ?
C36 C37 1.501(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.426(3) . ?
C38 C43 1.428(2) . ?
C39 C40 1.361(3) . ?
C39 H39 0.99(2) . ?
C40 C41 1.420(3) . ?
C40 H40 1.00(3) . ?
C41 C42 1.363(3) . ?
C41 H41 1.02(3) . ?
C42 C43 1.427(3) . ?
C42 H42 0.97(2) . ?
C43 C44 1.399(3) . ?
C44 C45 1.389(3) . ?
C44 H44 0.99(3) . ?
C45 C46 1.432(3) . ?
C45 C50 1.427(2) . ?
C46 C47 1.356(3) . ?
C46 H46 1.02(3) . ?
C47 C48 1.420(3) . ?
C47 H47 1.00(3) . ?
C48 C49 1.364(3) . ?
C48 H48 1.01(3) . ?
C49 C50 1.424(3) . ?
C49 H49 1.06(2) . ?
C51 C52 1.500(3) . ?
C51 H51A 1.02(3) . ?
C51 H51B 0.99(3) . ?
C51 H51C 0.95(3) . ?
C52 C53 1.391(3) . ?
C53 C54 1.505(3) . ?
C54 H54A 0.95(3) . ?
C54 H54B 0.95(3) . ?
C54 H54C 1.05(3) . ?
C55 C56 1.499(3) . ?
C55 H55A 0.99(3) . ?
C55 H55B 0.95(3) . ?
C55 H55C 0.99(4) . ?
C56 C57 1.394(3) . ?
C57 C58 1.497(2) . ?
C58 H58A 0.97(2) . ?
C58 H58B 0.98(3) . ?
C58 H58C 1.02(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
O3 H3 O2 0.91(3) 1.94(3) 2.768(2) 151(3) . yes
O1 H1 N5 1.03(4) 1.72(4) 2.751(2) 173(3) . yes
O2 H2 N7 0.99(3) 1.73(3) 2.7197(19) 177(3) . yes
O4 H4 N8 0.92(3) 1.90(3) 2.783(2) 161(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
O1 C10 C11 C12 -179.75(17) . . . . ?
O1 C10 C19 C18 179.59(16) . . . . ?
O2 C16 C17 C18 179.53(16) . . . . ?
O3 C20 C21 C22 177.06(16) . . . . ?
O3 C20 C29 C28 -176.39(16) . . . . ?
O4 C26 C27 C28 178.86(15) . . . . ?
N5 C31 C32 N6 -0.3(3) . . . . ?
N5 C31 C32 C33 179.82(19) . . . . ?
N6 C35 C36 N5 -0.3(3) . . . . ?
N6 C35 C36 C37 -179.53(18) . . . . ?
N7 C38 C39 C40 178.95(18) . . . . ?
N7 C38 C43 C42 -179.68(18) . . . . ?
N7 C38 C43 C44 0.0(3) . . . . ?
N8 C52 C53 N9 -0.9(3) . . . . ?
N8 C52 C53 C54 179.08(19) . . . . ?
N9 C56 C57 N8 -0.6(3) . . . . ?
N9 C56 C57 C58 179.60(19) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C10 C19 C18 -0.6(3) . . . . ?
C11 C12 C13 C14 178.44(17) . . . . ?
C11 C12 C13 C18 -1.9(3) . . . . ?
C12 C13 C14 C15 179.60(18) . . . . ?
C12 C13 C18 C17 -179.01(16) . . . . ?
C12 C13 C18 C19 1.7(2) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C13 C18 C19 C10 -0.4(3) . . . . ?
C14 C13 C18 C17 0.7(2) . . . . ?
C14 C13 C18 C19 -178.64(16) . . . . ?
C14 C15 C16 O2 -178.90(16) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C16 C17 C18 C13 -0.2(2) . . . . ?
C16 C17 C18 C19 179.06(16) . . . . ?
C17 C18 C19 C10 -179.75(16) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
C19 C10 C11 C12 0.4(3) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C20 C29 C28 2.2(3) . . . . ?
C21 C22 C23 C24 -177.42(16) . . . . ?
C21 C22 C23 C28 1.5(2) . . . . ?
C22 C23 C24 C25 179.29(16) . . . . ?
C22 C23 C28 C27 179.90(15) . . . . ?
C22 C23 C28 C29 -0.9(2) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C23 C28 C29 C20 -0.9(2) . . . . ?
C24 C23 C28 C27 -1.2(2) . . . . ?
C24 C23 C28 C29 178.03(15) . . . . ?
C24 C25 C26 O4 -179.68(15) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C25 C26 C27 C28 -0.9(3) . . . . ?
C26 C27 C28 C23 1.4(2) . . . . ?
C26 C27 C28 C29 -177.76(16) . . . . ?
C27 C28 C29 C20 178.25(16) . . . . ?
C28 C23 C24 C25 0.4(2) . . . . ?
C29 C20 C21 C22 -1.7(3) . . . . ?
C30 C31 C32 N6 179.37(18) . . . . ?
C30 C31 C32 C33 -0.5(3) . . . . ?
C31 N5 C36 C35 0.0(3) . . . . ?
C31 N5 C36 C37 179.25(17) . . . . ?
C32 N6 C35 C34 -179.32(18) . . . . ?
C32 N6 C35 C36 0.3(3) . . . . ?
C34 C35 C36 N5 179.31(18) . . . . ?
C34 C35 C36 C37 0.0(3) . . . . ?
C35 N6 C32 C31 0.0(3) . . . . ?
C35 N6 C32 C33 179.87(19) . . . . ?
C36 N5 C31 C30 -179.38(18) . . . . ?
C36 N5 C31 C32 0.3(3) . . . . ?
C38 N7 C50 C45 0.1(3) . . . . ?
C38 N7 C50 C49 179.85(17) . . . . ?
C38 C39 C40 C41 0.8(3) . . . . ?
C38 C43 C44 C45 -0.3(3) . . . . ?
C39 C38 C43 C42 0.0(3) . . . . ?
C39 C38 C43 C44 179.68(18) . . . . ?
C39 C40 C41 C42 -0.2(3) . . . . ?
C40 C41 C42 C43 -0.6(3) . . . . ?
C41 C42 C43 C38 0.7(3) . . . . ?
C41 C42 C43 C44 -179.0(2) . . . . ?
C42 C43 C44 C45 179.36(19) . . . . ?
C43 C38 C39 C40 -0.7(3) . . . . ?
C43 C44 C45 C46 -179.78(19) . . . . ?
C43 C44 C45 C50 0.5(3) . . . . ?
C44 C45 C46 C47 179.2(2) . . . . ?
C44 C45 C50 N7 -0.5(3) . . . . ?
C44 C45 C50 C49 179.85(18) . . . . ?
C45 C46 C47 C48 1.3(3) . . . . ?
C46 C45 C50 N7 179.84(17) . . . . ?
C46 C45 C50 C49 0.1(3) . . . . ?
C46 C47 C48 C49 -0.5(3) . . . . ?
C47 C48 C49 C50 -0.5(3) . . . . ?
C48 C49 C50 N7 -179.07(19) . . . . ?
C48 C49 C50 C45 0.6(3) . . . . ?
C50 N7 C38 C39 -179.60(17) . . . . ?
C50 N7 C38 C43 0.1(3) . . . . ?
C50 C45 C46 C47 -1.1(3) . . . . ?
C51 C52 C53 N9 179.52(19) . . . . ?
C51 C52 C53 C54 -0.5(3) . . . . ?
C52 N8 C57 C56 -0.6(3) . . . . ?
C52 N8 C57 C58 179.19(18) . . . . ?
C53 N9 C56 C55 -179.04(18) . . . . ?
C53 N9 C56 C57 1.1(3) . . . . ?
C55 C56 C57 N8 179.50(19) . . . . ?
C55 C56 C57 C58 -0.3(3) . . . . ?
C56 N9 C53 C52 -0.4(3) . . . . ?
C56 N9 C53 C54 179.70(19) . . . . ?
C57 N8 C52 C51 -179.06(17) . . . . ?
C57 N8 C52 C53 1.3(3) . . . . ?
