#------------------------------------------------------------------------------
#$Date: 2022-08-05 01:33:55 +0300 (Fri, 05 Aug 2022) $
#$Revision: 277074 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/52/7245263.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_7245263
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         '2(C10 H8 O2), C8 H6 N2, 2(C8 H12 N2)'
_chemical_formula_sum            'C44 H46 N6 O4'
_chemical_formula_weight         722.87
_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     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                91.6280(10)
_cell_angle_beta                 98.4360(10)
_cell_angle_gamma                103.4880(10)
_cell_formula_units_Z            2
_cell_length_a                   9.09200(10)
_cell_length_b                   12.2035(2)
_cell_length_c                   17.7698(3)
_cell_measurement_reflns_used    12755
_cell_measurement_temperature    123
_cell_measurement_theta_max      79.0800
_cell_measurement_theta_min      4.4040
_cell_volume                     1892.49(5)
_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_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9680
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  18.00   0.50    1.00    --    0.00 -37.00 150.00  214
  2  ω    -26.00  31.00   0.50    1.00    --    0.00  77.00  60.00  114
  3  ω     20.00  65.00   0.50    1.00    --    0.00  77.00   0.00   90
  4  ω    -88.00  19.00   0.50    1.00    --    0.00 -37.00-120.00  214
  5  ω    -30.00   0.00   0.50    1.00    --    0.00  77.00   0.00   60
  6  ω     37.00  78.00   0.50    1.00    --    0.00  37.00 120.00   82
  7  ω     26.00  52.00   0.50    3.50    --  107.20 -82.00-180.00   52
  8  ω     91.00 133.00   0.50    3.50    --  107.20 -82.00   0.00   84
  9  ω    103.00 177.00   0.50    3.50    --  107.20  30.00  90.00  148
 10  ω     20.00 125.00   0.50    3.50    --  107.20 -82.00 -60.00  210
 11  ω    122.00 196.00   0.50    3.50    --  107.20  30.00 150.00  148
 12  ω     21.00 140.00   0.50    3.50    --  107.20 -82.00 120.00  238
 13  ω     34.00 124.00   0.50    3.50    --  107.20 -30.00-180.00  180
 14  ω     63.00 105.00   0.50    3.50    --  107.20 -82.00 -90.00   84
 15  ω     25.00  51.00   0.50    3.50    --  107.20 -82.00   0.00   52
 16  ω     78.00 107.00   0.50    3.50    --  107.20 -82.00  60.00   58
 17  ω     59.00 125.00   0.50    3.50    --  107.20 -30.00 -30.00  132
 18  ω     58.00 125.00   0.50    3.50    --  107.20 -15.00 120.00  134
 19  ω     85.00 138.00   0.50    3.50    --  107.20 -82.00-180.00  106
 20  ω     89.00 194.00   0.50    3.50    --  107.20  30.00-180.00  210
 21  ω     85.00 116.00   0.50    3.50    --  107.20 -61.00 -30.00   62
 22  ω     18.00 115.00   0.50    3.50    --  107.20 -61.00 -60.00  194
 23  ω     21.00 109.00   0.50    3.50    --  107.20 -61.00 120.00  176
;
_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      0.0909061000
_diffrn_orient_matrix_UB_12      0.1063429000
_diffrn_orient_matrix_UB_13      -0.0321244000
_diffrn_orient_matrix_UB_21      -0.1484925000
_diffrn_orient_matrix_UB_22      0.0402014000
_diffrn_orient_matrix_UB_23      -0.0208625000
_diffrn_orient_matrix_UB_31      0.0286830000
_diffrn_orient_matrix_UB_32      0.0632455000
_diffrn_orient_matrix_UB_33      0.0790374000
_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  0.0335
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21056
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.655
_diffrn_reflns_theta_min         3.733
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56630
_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    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     660
_refine_ls_number_reflns         7977
_refine_ls_number_restraints     135
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0472
_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)+(0.0700P)²+0.4238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7151
_reflns_number_total             7977
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00735e2.cif
_cod_data_source_block           exp_1099_amr_75c-meno2
_cod_database_code               7245263
_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 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N6, C30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 All non-hydrogen atoms
 with sigma for 1-2 distances of 1 and sigma for 1-3 distances of 1
3.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 2.935
_oxdiff_exptl_absorpt_empirical_full_min 0.571
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 -0.05332(12) 0.46978(10) 0.18372(6) 0.0445(3) Uani 1 1 d . U . . .
O2 O 0.29572(11) 0.83236(8) 0.52643(5) 0.0367(2) Uani 1 1 d . U . . .
O3 O 0.77293(12) 1.09062(10) 0.34225(6) 0.0477(3) Uani 1 1 d . U . . .
O4 O 0.52562(12) 0.69424(10) 0.01291(6) 0.0460(3) Uani 1 1 d . U . . .
N5 N 0.11365(14) 0.31702(10) 0.23359(7) 0.0381(3) Uani 1 1 d . U . . .
N6 N 0.26094(19) 0.14737(12) 0.28302(7) 0.0518(3) Uani 1 1 d . U . . .
N7 N 0.47265(11) 0.68820(9) 0.56311(6) 0.0296(2) Uani 1 1 d . U . . .
N8 N 0.65238(12) 0.53698(9) 0.59285(6) 0.0308(2) Uani 1 1 d . U . . .
N9 N -0.03388(12) 0.07126(10) 0.10102(6) 0.0359(3) Uani 1 1 d . U . . .
N10 N 0.21192(12) 0.18817(10) 0.03844(6) 0.0346(2) Uani 1 1 d . U . . .
C10 C -0.13944(15) 0.63099(12) 0.21370(8) 0.0373(3) Uani 1 1 d . U . . .
C11 C -0.13322(15) 0.72257(12) 0.26013(8) 0.0369(3) Uani 1 1 d . U . . .
C12 C -0.02721(14) 0.74958(11) 0.32882(7) 0.0311(3) Uani 1 1 d . U . . .
C13 C -0.01508(15) 0.84645(11) 0.37701(8) 0.0351(3) Uani 1 1 d . U . . .
C14 C 0.09148(15) 0.87226(11) 0.44156(8) 0.0345(3) Uani 1 1 d . U . . .
C15 C 0.19101(14) 0.80020(11) 0.46156(7) 0.0297(3) Uani 1 1 d . U . . .
C16 C 0.18048(13) 0.70428(11) 0.41716(7) 0.0282(2) Uani 1 1 d . U . . .
C17 C 0.07253(13) 0.67701(10) 0.34913(7) 0.0273(2) Uani 1 1 d . U . . .
C18 C 0.06320(13) 0.58118(11) 0.30023(7) 0.0296(3) Uani 1 1 d . U . . .
C19 C -0.03992(14) 0.55907(12) 0.23362(7) 0.0335(3) Uani 1 1 d . U . . .
C20 C 0.66377(15) 1.00484(11) 0.30163(8) 0.0341(3) Uani 1 1 d . U . . .
C21 C 0.52767(16) 0.95523(13) 0.33019(8) 0.0375(3) Uani 1 1 d . U . . .
C22 C 0.42262(16) 0.86796(13) 0.28893(8) 0.0388(3) Uani 1 1 d . U . . .
C23 C 0.44690(14) 0.82460(11) 0.21842(7) 0.0329(3) Uani 1 1 d . U . . .
C24 C 0.34224(16) 0.73168(13) 0.17533(8) 0.0392(3) Uani 1 1 d . U . . .
C25 C 0.37060(16) 0.69098(12) 0.10828(8) 0.0385(3) Uani 1 1 d . U . . .
C26 C 0.50632(15) 0.74171(12) 0.07964(8) 0.0350(3) Uani 1 1 d . U . . .
C27 C 0.60900(14) 0.83326(12) 0.11880(7) 0.0330(3) Uani 1 1 d . U . . .
C28 C 0.58217(13) 0.87642(11) 0.18921(7) 0.0294(3) Uani 1 1 d . U . . .
C29 C 0.68921(14) 0.96786(12) 0.23238(7) 0.0331(3) Uani 1 1 d . U . . .
C30 C 0.1202(2) 0.14585(14) 0.29267(9) 0.0488(4) Uani 1 1 d . U . . .
C31 C 0.04652(19) 0.23004(14) 0.26816(8) 0.0449(3) Uani 1 1 d . U . . .
C32 C 0.25950(15) 0.32101(12) 0.22081(7) 0.0343(3) Uani 1 1 d . U . . .
C33 C 0.33369(19) 0.41146(14) 0.18136(9) 0.0445(3) Uani 1 1 d . U . . .
C34 C 0.4765(2) 0.41498(18) 0.16586(10) 0.0580(5) Uani 1 1 d . U . . .
C35 C 0.5519(2) 0.3310(2) 0.19052(11) 0.0676(6) Uani 1 1 d . U . . .
C36 C 0.4839(2) 0.24429(19) 0.22981(10) 0.0582(5) Uani 1 1 d . U . . .
C37 C 0.33426(17) 0.23631(13) 0.24524(8) 0.0409(3) Uani 1 1 d . U . . .
C38 C 0.66984(17) 0.82117(12) 0.51219(8) 0.0402(3) Uani 1 1 d . U . . .
H38A H 0.586906 0.837574 0.477949 0.060 Uiso 1 1 calc R U . . .
H38B H 0.751812 0.816476 0.484744 0.060 Uiso 1 1 calc R U . . .
H38C H 0.705840 0.880134 0.552131 0.060 Uiso 1 1 calc R U . . .
C39 C 0.61518(14) 0.71092(11) 0.54612(7) 0.0297(3) Uani 1 1 d . U . . .
C40 C 0.70594(13) 0.63352(11) 0.56126(7) 0.0299(3) Uani 1 1 d . U . . .
C41 C 0.86648(16) 0.65455(14) 0.54346(9) 0.0396(3) Uani 1 1 d . U . . .
C42 C 0.45778(18) 0.40713(13) 0.64744(9) 0.0401(3) Uani 1 1 d . U . . .
C43 C 0.51085(14) 0.51538(11) 0.61068(7) 0.0301(3) Uani 1 1 d . U . . .
C44 C 0.41866(13) 0.59191(11) 0.59563(7) 0.0299(3) Uani 1 1 d . U . . .
C45 C 0.25939(16) 0.57254(15) 0.61419(10) 0.0416(3) Uani 1 1 d . U . . .
C46 C 0.35989(18) 0.04916(15) 0.07137(10) 0.0457(4) Uani 1 1 d . U . . .
C47 C 0.21758(15) 0.09151(12) 0.07055(7) 0.0341(3) Uani 1 1 d . U . . .
C48 C 0.09239(15) 0.03180(12) 0.10273(7) 0.0347(3) Uani 1 1 d . U . . .
C49 C 0.0948(2) -0.07527(14) 0.14111(10) 0.0467(4) Uani 1 1 d . U . . .
C50 C -0.18070(18) 0.21055(16) 0.06950(10) 0.0449(3) Uani 1 1 d . U . . .
C51 C -0.03838(15) 0.16818(12) 0.06901(7) 0.0346(3) Uani 1 1 d . U . . .
C52 C 0.08644(15) 0.22870(12) 0.03725(7) 0.0344(3) Uani 1 1 d . U . . .
C53 C 0.0854(2) 0.33825(15) 0.00181(10) 0.0474(4) Uani 1 1 d . U . . .
H13 H -0.083(2) 0.8943(15) 0.3630(10) 0.047(5) Uiso 1 1 d . . . . .
H18 H 0.1323(18) 0.5319(14) 0.3135(9) 0.035(4) Uiso 1 1 d . . . . .
H21 H 0.509(2) 0.9850(15) 0.3777(10) 0.047(5) Uiso 1 1 d . . . . .
H16 H 0.2495(18) 0.6542(13) 0.4318(9) 0.032(4) Uiso 1 1 d . . . . .
H27 H 0.704(2) 0.8728(15) 0.0985(10) 0.044(4) Uiso 1 1 d . . . . .
H24 H 0.249(2) 0.6987(16) 0.1958(11) 0.052(5) Uiso 1 1 d . . . . .
H29 H 0.782(2) 1.0043(15) 0.2119(10) 0.045(4) Uiso 1 1 d . . . . .
H11 H -0.201(2) 0.7701(16) 0.2476(11) 0.054(5) Uiso 1 1 d . . . . .
H41A H 0.869(2) 0.6629(16) 0.4892(12) 0.054(5) Uiso 1 1 d . . . . .
H49A H 0.164(2) -0.0578(17) 0.1910(12) 0.063(6) Uiso 1 1 d . . . . .
H14 H 0.102(2) 0.9385(15) 0.4756(10) 0.045(4) Uiso 1 1 d . . . . .
H10 H -0.212(2) 0.6093(16) 0.1665(11) 0.057(5) Uiso 1 1 d . . . . .
H33 H 0.278(2) 0.4680(18) 0.1651(12) 0.063(6) Uiso 1 1 d . . . . .
H42A H 0.362(2) 0.3581(18) 0.6213(12) 0.064(6) Uiso 1 1 d . . . . .
H2 H 0.354(2) 0.7787(18) 0.5362(12) 0.060(5) Uiso 1 1 d . . . . .
H25 H 0.301(2) 0.6283(17) 0.0775(11) 0.055(5) Uiso 1 1 d . . . . .
H42B H 0.440(2) 0.4225(17) 0.6976(12) 0.062(6) Uiso 1 1 d . . . . .
H41B H 0.910(2) 0.5919(19) 0.5572(12) 0.064(6) Uiso 1 1 d . . . . .
H53A H 0.008(3) 0.3302(18) -0.0456(13) 0.069(6) Uiso 1 1 d . . . . .
H41C H 0.934(2) 0.7244(18) 0.5725(12) 0.061(6) Uiso 1 1 d . . . . .
H31 H -0.067(2) 0.2250(17) 0.2777(11) 0.062(6) Uiso 1 1 d . . . . .
H30 H 0.061(2) 0.0755(18) 0.3187(12) 0.062(6) Uiso 1 1 d . . . . .
H50A H -0.252(3) 0.1554(19) 0.0975(12) 0.068(6) Uiso 1 1 d . . . . .
H22 H 0.329(2) 0.8328(17) 0.3084(11) 0.060(5) Uiso 1 1 d . . . . .
H53B H 0.193(3) 0.3751(18) -0.0112(12) 0.066(6) Uiso 1 1 d . . . . .
H3 H 0.743(2) 1.1078(18) 0.3833(13) 0.062(6) Uiso 1 1 d . . . . .
H50B H -0.154(3) 0.286(2) 0.0932(14) 0.079(7) Uiso 1 1 d . . . . .
H34 H 0.531(3) 0.4737(19) 0.1367(13) 0.069(6) Uiso 1 1 d . . . . .
H53C H 0.046(3) 0.389(2) 0.0363(13) 0.075(7) Uiso 1 1 d . . . . .
H45A H 0.227(3) 0.641(2) 0.6244(15) 0.094(8) Uiso 1 1 d . . . . .
H46A H 0.446(3) 0.109(2) 0.0553(13) 0.074(6) Uiso 1 1 d . . . . .
H1 H 0.013(3) 0.4243(19) 0.2037(13) 0.073(7) Uiso 1 1 d . . . . .
H50C H -0.224(3) 0.2224(18) 0.0195(13) 0.068(6) Uiso 1 1 d . . . . .
H42C H 0.533(3) 0.362(2) 0.6497(14) 0.085(7) Uiso 1 1 d . . . . .
H4 H 0.616(3) 0.739(2) -0.0043(14) 0.091(8) Uiso 1 1 d . . . . .
H49B H -0.015(3) -0.111(2) 0.1555(14) 0.088(7) Uiso 1 1 d . . . . .
H46B H 0.399(3) 0.032(2) 0.1240(16) 0.094(8) Uiso 1 1 d . . . . .
H35 H 0.657(3) 0.341(2) 0.1789(14) 0.084(7) Uiso 1 1 d . . . . .
H49C H 0.133(3) -0.129(2) 0.1101(13) 0.076(7) Uiso 1 1 d . . . . .
H36 H 0.527(3) 0.178(2) 0.2466(13) 0.079(7) Uiso 1 1 d . . . . .
H45B H 0.240(3) 0.531(2) 0.6562(17) 0.103(9) Uiso 1 1 d . . . . .
H45C H 0.189(4) 0.533(3) 0.5718(19) 0.120(10) Uiso 1 1 d . . . . .
H46C H 0.347(3) -0.018(2) 0.0342(16) 0.100(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
C19 O1 H1 109.7(14) . . ?
C15 O2 H2 110.5(12) . . ?
C20 O3 H3 109.5(14) . . ?
C26 O4 H4 109.6(15) . . ?
C31 N5 C32 116.93(13) . . ?
C30 N6 C37 116.54(14) . . ?
C39 N7 C44 119.77(11) . . ?
C40 N8 C43 119.24(11) . . ?
C51 N9 C48 119.03(12) . . ?
C47 N10 C52 119.70(12) . . ?
C11 C10 C19 120.16(12) . . ?
C11 C10 H10 123.4(11) . . ?
C19 C10 H10 116.4(11) . . ?
C10 C11 C12 121.39(12) . . ?
C10 C11 H11 120.5(11) . . ?
C12 C11 H11 118.1(11) . . ?
C11 C12 C17 118.53(12) . . ?
C13 C12 C11 122.51(12) . . ?
C13 C12 C17 118.95(12) . . ?
C12 C13 H13 118.3(10) . . ?
C14 C13 C12 121.21(12) . . ?
C14 C13 H13 120.5(10) . . ?
C13 C14 C15 119.78(13) . . ?
C13 C14 H14 122.8(10) . . ?
C15 C14 H14 117.4(10) . . ?
O2 C15 C14 116.36(11) . . ?
O2 C15 C16 122.95(11) . . ?
C16 C15 C14 120.69(12) . . ?
C15 C16 C17 120.42(11) . . ?
C15 C16 H16 120.1(9) . . ?
C17 C16 H16 119.4(9) . . ?
C16 C17 C12 118.92(12) . . ?
C18 C17 C12 119.21(11) . . ?
C18 C17 C16 121.86(11) . . ?
C17 C18 H18 119.5(9) . . ?
C19 C18 C17 120.30(12) . . ?
C19 C18 H18 120.2(9) . . ?
O1 C19 C10 116.25(12) . . ?
O1 C19 C18 123.34(12) . . ?
C18 C19 C10 120.41(13) . . ?
O3 C20 C21 121.08(12) . . ?
O3 C20 C29 118.19(12) . . ?
C29 C20 C21 120.72(13) . . ?
C20 C21 H21 119.6(11) . . ?
C22 C21 C20 119.56(13) . . ?
C22 C21 H21 120.8(11) . . ?
C21 C22 C23 121.52(13) . . ?
C21 C22 H22 120.1(12) . . ?
C23 C22 H22 118.4(12) . . ?
C22 C23 C24 122.89(12) . . ?
C22 C23 C28 118.65(13) . . ?
C24 C23 C28 118.45(12) . . ?
C23 C24 H24 117.1(11) . . ?
C25 C24 C23 121.29(13) . . ?
C25 C24 H24 121.6(11) . . ?
C24 C25 C26 120.26(13) . . ?
C24 C25 H25 123.3(12) . . ?
C26 C25 H25 116.5(12) . . ?
O4 C26 C25 115.98(13) . . ?
O4 C26 C27 123.76(12) . . ?
C27 C26 C25 120.26(13) . . ?
C26 C27 C28 120.35(12) . . ?
C26 C27 H27 121.7(10) . . ?
C28 C27 H27 117.9(10) . . ?
C27 C28 C23 119.37(12) . . ?
C29 C28 C23 119.05(12) . . ?
C29 C28 C27 121.55(11) . . ?
C20 C29 C28 120.44(12) . . ?
C20 C29 H29 120.5(10) . . ?
C28 C29 H29 119.1(10) . . ?
N6 C30 C31 122.93(15) . . ?
N6 C30 H30 116.8(11) . . ?
C31 C30 H30 120.2(11) . . ?
N5 C31 C30 122.24(15) . . ?
N5 C31 H31 117.9(11) . . ?
C30 C31 H31 119.9(11) . . ?
N5 C32 C33 118.58(13) . . ?
N5 C32 C37 121.08(13) . . ?
C37 C32 C33 120.33(14) . . ?
C32 C33 H33 117.8(12) . . ?
C34 C33 C32 119.51(17) . . ?
C34 C33 H33 122.7(12) . . ?
C33 C34 C35 120.33(18) . . ?
C33 C34 H34 122.8(13) . . ?
C35 C34 H34 116.8(13) . . ?
C34 C35 H35 115.9(15) . . ?
C36 C35 C34 121.19(17) . . ?
C36 C35 H35 122.9(15) . . ?
C35 C36 C37 120.05(18) . . ?
C35 C36 H36 126.3(14) . . ?
C37 C36 H36 113.4(14) . . ?
N6 C37 C32 120.24(14) . . ?
N6 C37 C36 121.20(16) . . ?
C36 C37 C32 118.56(16) . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C39 C38 H38A 109.5 . . ?
C39 C38 H38B 109.5 . . ?
C39 C38 H38C 109.5 . . ?
N7 C39 C38 117.04(11) . . ?
N7 C39 C40 119.82(12) . . ?
C40 C39 C38 123.13(12) . . ?
N8 C40 C39 120.73(11) . . ?
N8 C40 C41 117.14(12) . . ?
C39 C40 C41 122.13(12) . . ?
C40 C41 H41A 111.6(11) . . ?
C40 C41 H41B 110.2(13) . . ?
C40 C41 H41C 111.0(12) . . ?
H41A C41 H41B 107.3(17) . . ?
H41A C41 H41C 108.5(17) . . ?
H41B C41 H41C 108.2(17) . . ?
C43 C42 H42A 114.9(12) . . ?
C43 C42 H42B 110.2(13) . . ?
C43 C42 H42C 110.8(15) . . ?
H42A C42 H42B 105.8(18) . . ?
H42A C42 H42C 105.8(19) . . ?
H42B C42 H42C 109.1(19) . . ?
N8 C43 C42 117.04(12) . . ?
N8 C43 C44 120.62(12) . . ?
C44 C43 C42 122.34(12) . . ?
N7 C44 C43 119.80(11) . . ?
N7 C44 C45 117.05(12) . . ?
C43 C44 C45 123.14(13) . . ?
C44 C45 H45A 114.2(16) . . ?
C44 C45 H45B 116.3(18) . . ?
C44 C45 H45C 109.1(19) . . ?
H45A C45 H45B 104(2) . . ?
H45A C45 H45C 106(2) . . ?
H45B C45 H45C 106(3) . . ?
C47 C46 H46A 111.2(13) . . ?
C47 C46 H46B 110.4(15) . . ?
C47 C46 H46C 113.6(16) . . ?
H46A C46 H46B 106.0(19) . . ?
H46A C46 H46C 104(2) . . ?
H46B C46 H46C 111(2) . . ?
N10 C47 C46 118.27(13) . . ?
N10 C47 C48 120.23(12) . . ?
C48 C47 C46 121.50(13) . . ?
N9 C48 C47 120.35(13) . . ?
N9 C48 C49 117.43(13) . . ?
C47 C48 C49 122.21(13) . . ?
C48 C49 H49A 109.4(12) . . ?
C48 C49 H49B 109.7(14) . . ?
C48 C49 H49C 112.0(14) . . ?
H49A C49 H49B 104.7(17) . . ?
H49A C49 H49C 107.9(18) . . ?
H49B C49 H49C 112.7(19) . . ?
C51 C50 H50A 107.3(12) . . ?
C51 C50 H50B 109.8(14) . . ?
C51 C50 H50C 111.3(13) . . ?
H50A C50 H50B 112.2(19) . . ?
H50A C50 H50C 114.5(18) . . ?
H50B C50 H50C 101.7(19) . . ?
N9 C51 C50 117.39(13) . . ?
N9 C51 C52 120.99(12) . . ?
C52 C51 C50 121.61(14) . . ?
N10 C52 C51 119.70(13) . . ?
N10 C52 C53 118.12(13) . . ?
C51 C52 C53 122.18(13) . . ?
C52 C53 H53A 113.1(13) . . ?
C52 C53 H53B 110.3(12) . . ?
C52 C53 H53C 109.5(13) . . ?
H53A C53 H53B 108.8(17) . . ?
H53A C53 H53C 101.3(18) . . ?
H53B C53 H53C 113.6(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
O1 C19 1.3564(17) . ?
O1 H1 0.95(2) . ?
O2 C15 1.3665(15) . ?
O2 H2 0.94(2) . ?
O3 C20 1.3654(17) . ?
O3 H3 0.85(2) . ?
O4 C26 1.3571(17) . ?
O4 H4 0.97(3) . ?
N5 C31 1.312(2) . ?
N5 C32 1.3680(18) . ?
N6 C30 1.312(2) . ?
N6 C37 1.381(2) . ?
N7 C39 1.3414(16) . ?
N7 C44 1.3448(17) . ?
N8 C40 1.3380(17) . ?
N8 C43 1.3385(16) . ?
N9 C48 1.3414(17) . ?
N9 C51 1.3335(19) . ?
N10 C47 1.3334(18) . ?
N10 C52 1.3429(17) . ?
C10 C11 1.356(2) . ?
C10 C19 1.4172(19) . ?
C10 H10 0.98(2) . ?
C11 C12 1.4181(19) . ?
C11 H11 0.950(19) . ?
C12 C13 1.413(2) . ?
C12 C17 1.4261(16) . ?
C13 C14 1.366(2) . ?
C13 H13 0.955(18) . ?
C14 C15 1.4188(17) . ?
C14 H14 0.972(18) . ?
C15 C16 1.3692(18) . ?
C16 C17 1.4185(17) . ?
C16 H16 0.987(16) . ?
C17 C18 1.4157(18) . ?
C18 C19 1.3753(17) . ?
C18 H18 0.976(17) . ?
C20 C21 1.4168(19) . ?
C20 C29 1.3682(19) . ?
C21 C22 1.364(2) . ?
C21 H21 0.963(18) . ?
C22 C23 1.413(2) . ?
C22 H22 0.98(2) . ?
C23 C24 1.418(2) . ?
C23 C28 1.4231(17) . ?
C24 C25 1.360(2) . ?
C24 H24 0.97(2) . ?
C25 C26 1.4181(19) . ?
C25 H25 0.965(19) . ?
C26 C27 1.3722(19) . ?
C27 C28 1.4191(18) . ?
C27 H27 1.006(18) . ?
C28 C29 1.4166(19) . ?
C29 H29 0.981(18) . ?
C30 C31 1.398(3) . ?
C30 H30 1.06(2) . ?
C31 H31 1.06(2) . ?
C32 C33 1.414(2) . ?
C32 C37 1.409(2) . ?
C33 C34 1.358(2) . ?
C33 H33 0.97(2) . ?
C34 C35 1.406(3) . ?
C34 H34 0.98(2) . ?
C35 C36 1.361(3) . ?
C35 H35 0.99(3) . ?
C36 C37 1.409(2) . ?
C36 H36 1.01(2) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C38 C39 1.4976(18) . ?
C39 C40 1.3994(18) . ?
C40 C41 1.5039(17) . ?
C41 H41A 0.98(2) . ?
C41 H41B 0.96(2) . ?
C41 H41C 1.00(2) . ?
C42 C43 1.4997(19) . ?
C42 H42A 0.98(2) . ?
C42 H42B 0.95(2) . ?
C42 H42C 0.97(3) . ?
C43 C44 1.4000(18) . ?
C44 C45 1.4988(18) . ?
C45 H45A 0.97(3) . ?
C45 H45B 0.93(3) . ?
C45 H45C 0.95(3) . ?
C46 C47 1.4995(19) . ?
C46 H46A 1.02(2) . ?
C46 H46B 1.00(3) . ?
C46 H46C 1.01(3) . ?
C47 C48 1.407(2) . ?
C48 C49 1.494(2) . ?
C49 H49A 1.00(2) . ?
C49 H49B 1.07(3) . ?
C49 H49C 1.00(2) . ?
C50 C51 1.5023(19) . ?
C50 H50A 1.01(2) . ?
C50 H50B 0.96(2) . ?
C50 H50C 0.95(2) . ?
C51 C52 1.404(2) . ?
C52 C53 1.495(2) . ?
C53 H53A 1.00(2) . ?
C53 H53B 1.04(2) . ?
C53 H53C 1.01(2) . ?
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 C15 C16 C17 -178.05(11) . . . . ?
O3 C20 C21 C22 -178.50(13) . . . . ?
O3 C20 C29 C28 177.73(12) . . . . ?
O4 C26 C27 C28 -178.56(12) . . . . ?
N5 C32 C33 C34 -177.83(13) . . . . ?
N5 C32 C37 N6 -0.21(19) . . . . ?
N5 C32 C37 C36 179.38(13) . . . . ?
N6 C30 C31 N5 0.0(2) . . . . ?
N7 C39 C40 N8 -0.25(18) . . . . ?
N7 C39 C40 C41 -179.96(12) . . . . ?
N8 C43 C44 N7 -0.15(18) . . . . ?
N8 C43 C44 C45 179.96(12) . . . . ?
N9 C51 C52 N10 0.57(19) . . . . ?
N9 C51 C52 C53 -179.27(13) . . . . ?
N10 C47 C48 N9 0.35(19) . . . . ?
N10 C47 C48 C49 -178.39(13) . . . . ?
C10 C11 C12 C13 177.96(13) . . . . ?
C10 C11 C12 C17 -0.93(19) . . . . ?
C11 C10 C19 O1 -179.66(12) . . . . ?
C11 C10 C19 C18 0.3(2) . . . . ?
C11 C12 C13 C14 -177.86(12) . . . . ?
C11 C12 C17 C16 179.08(11) . . . . ?
C11 C12 C17 C18 0.29(17) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C12 C17 C18 C19 0.60(18) . . . . ?
C13 C12 C17 C16 0.15(17) . . . . ?
C13 C12 C17 C18 -178.63(11) . . . . ?
C13 C14 C15 O2 179.24(12) . . . . ?
C13 C14 C15 C16 -0.61(19) . . . . ?
C14 C15 C16 C17 1.80(18) . . . . ?
C15 C16 C17 C12 -1.55(17) . . . . ?
C15 C16 C17 C18 177.20(11) . . . . ?
C16 C17 C18 C19 -178.14(11) . . . . ?
C17 C12 C13 C14 1.03(19) . . . . ?
C17 C18 C19 O1 179.04(12) . . . . ?
C17 C18 C19 C10 -0.90(19) . . . . ?
C19 C10 C11 C12 0.6(2) . . . . ?
C20 C21 C22 C23 0.7(2) . . . . ?
C21 C20 C29 C28 -2.3(2) . . . . ?
C21 C22 C23 C24 177.94(13) . . . . ?
C21 C22 C23 C28 -2.1(2) . . . . ?
C22 C23 C24 C25 -178.88(13) . . . . ?
C22 C23 C28 C27 179.43(12) . . . . ?
C22 C23 C28 C29 1.34(18) . . . . ?
C23 C24 C25 C26 -0.4(2) . . . . ?
C23 C28 C29 C20 0.84(19) . . . . ?
C24 C23 C28 C27 -0.65(18) . . . . ?
C24 C23 C28 C29 -178.74(12) . . . . ?
C24 C25 C26 O4 179.10(13) . . . . ?
C24 C25 C26 C27 -0.9(2) . . . . ?
C25 C26 C27 C28 1.5(2) . . . . ?
C26 C27 C28 C23 -0.68(18) . . . . ?
C26 C27 C28 C29 177.37(12) . . . . ?
C27 C28 C29 C20 -177.21(12) . . . . ?
C28 C23 C24 C25 1.2(2) . . . . ?
C29 C20 C21 C22 1.5(2) . . . . ?
C30 N6 C37 C32 1.5(2) . . . . ?
C30 N6 C37 C36 -178.06(14) . . . . ?
C31 N5 C32 C33 177.86(12) . . . . ?
C31 N5 C32 C37 -1.23(18) . . . . ?
C32 N5 C31 C30 1.4(2) . . . . ?
C32 C33 C34 C35 -1.6(2) . . . . ?
C33 C32 C37 N6 -179.28(12) . . . . ?
C33 C32 C37 C36 0.3(2) . . . . ?
C33 C34 C35 C36 0.4(3) . . . . ?
C34 C35 C36 C37 1.2(3) . . . . ?
C35 C36 C37 N6 178.07(15) . . . . ?
C35 C36 C37 C32 -1.5(2) . . . . ?
C37 N6 C30 C31 -1.4(2) . . . . ?
C37 C32 C33 C34 1.3(2) . . . . ?
C38 C39 C40 N8 178.85(12) . . . . ?
C38 C39 C40 C41 -0.86(19) . . . . ?
C39 N7 C44 C43 -0.78(17) . . . . ?
C39 N7 C44 C45 179.12(11) . . . . ?
C40 N8 C43 C42 -178.75(11) . . . . ?
C40 N8 C43 C44 0.86(17) . . . . ?
C42 C43 C44 N7 179.44(12) . . . . ?
C42 C43 C44 C45 -0.4(2) . . . . ?
C43 N8 C40 C39 -0.67(17) . . . . ?
C43 N8 C40 C41 179.06(11) . . . . ?
C44 N7 C39 C38 -178.19(11) . . . . ?
C44 N7 C39 C40 0.97(17) . . . . ?
C46 C47 C48 N9 -179.75(13) . . . . ?
C46 C47 C48 C49 1.5(2) . . . . ?
C47 N10 C52 C51 -0.77(18) . . . . ?
C47 N10 C52 C53 179.07(12) . . . . ?
C48 N9 C51 C50 -178.93(12) . . . . ?
C48 N9 C51 C52 0.11(18) . . . . ?
C50 C51 C52 N10 179.57(12) . . . . ?
C50 C51 C52 C53 -0.3(2) . . . . ?
C51 N9 C48 C47 -0.56(18) . . . . ?
C51 N9 C48 C49 178.24(12) . . . . ?
C52 N10 C47 C46 -179.57(12) . . . . ?
C52 N10 C47 C48 0.33(18) . . . . ?
