#------------------------------------------------------------------------------
#$Date: 2021-03-05 20:43:22 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560041.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_1560041
loop_
_publ_author_name
'Rajkumar, Madhu'
'Desiraju, Gautam R.'
_publ_section_title
;
 Quaternary and quinary molecular solids based on structural inequivalence
 and combinatorial approaches: 2-nitroresorcinol and
 4,6-dichlororesorcinol
;
_journal_coeditor_code           YC5029
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              178
_journal_page_last               185
_journal_paper_doi               10.1107/S2052252520016589
_journal_volume                  8
_journal_year                    2021
_chemical_formula_sum            'C20 H22 N4 O8'
_chemical_formula_weight         446.41
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                86.559(6)
_cell_angle_beta                 78.838(6)
_cell_angle_gamma                66.314(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7162(8)
_cell_length_b                   8.9727(9)
_cell_length_c                   16.9089(17)
_cell_measurement_reflns_used    10074
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1051.59(19)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.042
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       Block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.6(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     612
_refine_ls_number_reflns         9240
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0388P)²+0.8048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7362
_reflns_number_total             9240
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           1NRES-TMP
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/IUCr/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1560041--1560072.cif.
;
_cod_database_code               1560041
_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_min   0.978
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'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
O13 O 0.2403(5) 0.7004(4) 0.0925(2) 0.0295(7) Uani 1 1 d . . . . .
O14 O 0.2482(5) 1.1162(4) -0.0863(2) 0.0330(8) Uani 1 1 d . . . . .
O15 O 0.0087(5) 0.9269(4) -0.0605(2) 0.0341(8) Uani 1 1 d . . . . .
O16 O -0.0640(5) 1.0132(5) 0.0624(2) 0.0497(11) Uani 1 1 d . . . . .
N2 N 0.0530(5) 0.9533(4) 0.0011(2) 0.0237(8) Uani 1 1 d . . . . .
C12 C 0.3460(6) 0.7766(5) 0.0508(3) 0.0228(9) Uani 1 1 d . . . . .
C8 C 0.3528(6) 0.9931(5) -0.0441(3) 0.0224(9) Uani 1 1 d . . . . .
C9 C 0.5491(6) 0.9460(6) -0.0430(3) 0.0253(10) Uani 1 1 d . . . . .
H9 H 0.6180 1.0011 -0.0732 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2572(6) 0.9049(5) 0.0029(3) 0.0215(9) Uani 1 1 d . . . . .
C11 C 0.5414(6) 0.7308(6) 0.0500(3) 0.0285(10) Uani 1 1 d . . . . .
H11 H 0.6067 0.6435 0.0804 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6379(6) 0.8167(6) 0.0036(3) 0.0274(10) Uani 1 1 d . . . . .
H10 H 0.7681 0.7855 0.0039 0.033 Uiso 1 1 calc R U . . .
O1 O 0.9754(6) 0.6516(5) 0.7402(3) 0.0526(11) Uani 1 1 d . . . . .
O2 O 1.0996(8) 0.0875(5) 0.6836(3) 0.0672(13) Uani 1 1 d . . . . .
H2 H 1.1533 0.1053 0.6395 0.101 Uiso 1 1 calc R U . . .
O3 O 1.1866(5) 0.4996(5) 0.6081(2) 0.0493(10) Uani 1 1 d . . . . .
O4 O 1.2108(7) 0.2629(5) 0.5789(3) 0.0688(13) Uani 1 1 d . . . . .
N4 N 1.1520(6) 0.3796(6) 0.6272(3) 0.0411(11) Uani 1 1 d . . . . .
C19 C 1.0447(7) 0.3712(6) 0.7054(3) 0.0377(11) Uani 1 1 d . . . . .
C20 C 0.9642(8) 0.5062(7) 0.7585(3) 0.0431(14) Uani 1 1 d . . . . .
C22 C 0.8506(9) 0.3498(11) 0.8565(4) 0.067(2) Uani 1 1 d . . . . .
H22 H 0.7852 0.3427 0.9080 0.080 Uiso 1 1 calc R U . . .
C21 C 0.8662(8) 0.4932(9) 0.8349(3) 0.0566(17) Uani 1 1 d . . . . .
H21 H 0.8117 0.5815 0.8708 0.068 Uiso 1 1 calc R U . . .
C23 C 0.9266(9) 0.2149(9) 0.8063(4) 0.0622(18) Uani 1 1 d . . . . .
H23 H 0.9117 0.1197 0.8235 0.075 Uiso 1 1 calc R U . . .
C24 C 1.0248(9) 0.2230(7) 0.7301(4) 0.0499(15) Uani 1 1 d . . . . .
O5 O 0.7411(5) 0.6261(4) 0.6045(2) 0.0300(8) Uani 1 1 d . . . . .
O6 O 0.7682(5) 1.0207(4) 0.4128(2) 0.0310(8) Uani 1 1 d . . . . .
O8 O 0.9636(5) 0.8369(4) 0.58108(19) 0.0300(7) Uani 1 1 d . . . . .
O7 O 1.0709(5) 0.7287(4) 0.4619(2) 0.0351(8) Uani 1 1 d . . . . .
N3 N 0.9395(5) 0.7946(4) 0.5183(2) 0.0222(8) Uani 1 1 d . . . . .
C3 C 0.4588(6) 0.7747(5) 0.5461(3) 0.0251(10) Uani 1 1 d . . . . .
H3 H 0.3890 0.7203 0.5765 0.030 Uiso 1 1 calc R U . . .
C2 C 0.6454(6) 0.7394(5) 0.5556(3) 0.0213(9) Uani 1 1 d . . . . .
C6 C 0.6616(6) 0.9427(5) 0.4541(3) 0.0233(9) Uani 1 1 d . . . . .
C1 C 0.7433(6) 0.8259(5) 0.5087(2) 0.0196(9) Uani 1 1 d . . . . .
C5 C 0.4746(7) 0.9750(6) 0.4458(3) 0.0276(10) Uani 1 1 d . . . . .
H5A H 0.4160 1.0525 0.4096 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3755(7) 0.8906(6) 0.4918(3) 0.0286(10) Uani 1 1 d . . . . .
H4 H 0.2502 0.9125 0.4860 0.034 Uiso 1 1 calc R U . . .
O10 O 0.0478(6) 0.0879(5) 0.2066(3) 0.0436(9) Uani 1 1 d . . . . .
O12 O -0.0521(8) 0.3087(6) 0.1000(3) 0.0713(14) Uani 1 1 d . . . . .
O11 O -0.0531(7) 0.5450(6) 0.1136(3) 0.0694(14) Uani 1 1 d . . . . .
O9 O -0.0419(7) 0.6486(5) 0.2502(3) 0.0676(13) Uani 1 1 d . . . . .
H9A H -0.0674 0.6619 0.2047 0.101 Uiso 1 1 calc R U . . .
N1 N -0.0378(7) 0.4107(6) 0.1414(3) 0.0468(12) Uani 1 1 d . . . . .
C15 C 0.0203(7) 0.4565(7) 0.3504(4) 0.0490(15) Uani 1 1 d . . . . .
H15 H 0.0153 0.5364 0.3844 0.059 Uiso 1 1 calc R U . . .
C16 C 0.0572(7) 0.3014(7) 0.3783(3) 0.0411(13) Uani 1 1 d . . . . .
H16 H 0.0765 0.2782 0.4311 0.049 Uiso 1 1 calc R U . . .
C18 C 0.0351(6) 0.2127(6) 0.2507(3) 0.0304(11) Uani 1 1 d . . . . .
C13 C -0.0041(7) 0.3726(6) 0.2227(3) 0.0355(11) Uani 1 1 d . . . . .
C17 C 0.0661(7) 0.1784(6) 0.3289(3) 0.0370(11) Uani 1 1 d . . . . .
H17 H 0.0928 0.0740 0.3485 0.044 Uiso 1 1 calc R U . . .
C14 C -0.0094(7) 0.4948(6) 0.2724(4) 0.0412(13) Uani 1 1 d . . . . .
N5 N 0.5430(5) 0.4698(4) 0.6985(2) 0.0228(8) Uani 1 1 d . . . . .
N6 N 0.4206(5) 0.2833(4) 0.8119(2) 0.0219(8) Uani 1 1 d . . . . .
C32 C 0.6938(8) 0.2482(6) 0.5993(3) 0.0326(11) Uani 1 1 d . . . . .
H32A H 0.6101 0.2325 0.5684 0.049 Uiso 1 1 calc R U . . .
H32B H 0.7981 0.1459 0.6044 0.049 Uiso 1 1 calc R U . . .
H32C H 0.7442 0.3236 0.5726 0.049 Uiso 1 1 calc R U . . .
C28 C 0.2633(8) 0.5079(6) 0.9097(3) 0.0351(11) Uani 1 1 d . . . . .
H28A H 0.1474 0.5992 0.9033 0.053 Uiso 1 1 calc R U . . .
H28B H 0.3380 0.5425 0.9378 0.053 Uiso 1 1 calc R U . . .
H28C H 0.2309 0.4259 0.9401 0.053 Uiso 1 1 calc R U . . .
C29 C 0.5649(8) 0.0434(6) 0.7240(3) 0.0379(12) Uani 1 1 d . . . . .
H29A H 0.6982 -0.0213 0.7250 0.057 Uiso 1 1 calc R U . . .
H29B H 0.5381 0.0317 0.6721 0.057 Uiso 1 1 calc R U . . .
H29C H 0.4859 0.0077 0.7650 0.057 Uiso 1 1 calc R U . . .
C25 C 0.3960(8) 0.7096(6) 0.7856(3) 0.0355(12) Uani 1 1 d . . . . .
H25A H 0.4528 0.7522 0.7390 0.053 Uiso 1 1 calc R U . . .
H25B H 0.4480 0.7189 0.8313 0.053 Uiso 1 1 calc R U . . .
H25C H 0.2591 0.7702 0.7961 0.053 Uiso 1 1 calc R U . . .
C31 C 0.5828(6) 0.3145(5) 0.6814(3) 0.0238(9) Uani 1 1 d . . . . .
C27 C 0.3785(6) 0.4391(5) 0.8282(3) 0.0226(9) Uani 1 1 d . . . . .
C26 C 0.4401(6) 0.5343(5) 0.7703(3) 0.0229(9) Uani 1 1 d . . . . .
C30 C 0.5220(6) 0.2188(5) 0.7393(3) 0.0233(9) Uani 1 1 d . . . . .
N8 N 0.4285(5) 0.4716(4) 0.1947(2) 0.0251(8) Uani 1 1 d . . . . .
N7 N 0.5741(5) 0.2446(4) 0.3074(2) 0.0235(8) Uani 1 1 d . . . . .
C37 C 0.4592(8) 0.2652(6) 0.0994(3) 0.0342(11) Uani 1 1 d . . . . .
H37A H 0.3927 0.3614 0.0714 0.051 Uiso 1 1 calc R U . . .
H37B H 0.3866 0.1983 0.1077 0.051 Uiso 1 1 calc R U . . .
H37C H 0.5841 0.2055 0.0678 0.051 Uiso 1 1 calc R U . . .
C36 C 0.3792(8) 0.6985(6) 0.2802(3) 0.0380(12) Uani 1 1 d . . . . .
H36A H 0.3530 0.7553 0.2311 0.057 Uiso 1 1 calc R U . . .
H36B H 0.4785 0.7188 0.2982 0.057 Uiso 1 1 calc R U . . .
H36C H 0.2643 0.7360 0.3207 0.057 Uiso 1 1 calc R U . . .
C33 C 0.5342(7) 0.4498(6) 0.4038(3) 0.0317(11) Uani 1 1 d . . . . .
H33A H 0.4092 0.4911 0.4378 0.047 Uiso 1 1 calc R U . . .
H33B H 0.5853 0.5321 0.3977 0.047 Uiso 1 1 calc R U . . .
H33C H 0.6186 0.3557 0.4278 0.047 Uiso 1 1 calc R U . . .
C38 C 0.4811(6) 0.3123(5) 0.1793(3) 0.0230(9) Uani 1 1 d . . . . .
C34 C 0.5176(6) 0.4036(5) 0.3229(3) 0.0228(9) Uani 1 1 d . . . . .
C35 C 0.4445(6) 0.5192(5) 0.2654(3) 0.0242(10) Uani 1 1 d . . . . .
C39 C 0.5556(6) 0.1978(5) 0.2366(3) 0.0226(9) Uani 1 1 d . . . . .
C40 C 0.6157(8) 0.0185(6) 0.2227(3) 0.0348(12) Uani 1 1 d . . . . .
H40A H 0.7030 -0.0419 0.2578 0.052 Uiso 1 1 calc R U . . .
H40B H 0.6783 -0.0099 0.1676 0.052 Uiso 1 1 calc R U . . .
H40C H 0.5040 -0.0072 0.2339 0.052 Uiso 1 1 calc R U . . .
H5 H 0.656(9) 0.569(7) 0.636(4) 0.058(19) Uiso 1 1 d . . . . .
H6 H 0.714(8) 1.079(6) 0.382(3) 0.031(15) Uiso 1 1 d . . . . .
H13 H 0.321(10) 0.617(8) 0.125(4) 0.07(2) Uiso 1 1 d . . . . .
H14 H 0.302(7) 1.165(6) -0.107(3) 0.027(14) Uiso 1 1 d . . . . .
H10A H 0.017(10) 0.117(8) 0.164(4) 0.06(2) Uiso 1 1 d . . . . .
H1 H 1.026(8) 0.645(7) 0.694(3) 0.032(16) 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C12 O13 H13 108(4) . . ?
C8 O14 H14 113(4) . . ?
O15 N2 O16 123.4(4) . . ?
O15 N2 C7 118.5(4) . . ?
O16 N2 C7 118.1(4) . . ?
O13 C12 C7 118.0(4) . . ?
O13 C12 C11 124.1(4) . . ?
C7 C12 C11 117.9(4) . . ?
O14 C8 C7 117.0(4) . . ?
O14 C8 C9 125.3(4) . . ?
C7 C8 C9 117.7(4) . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C12 C7 C8 123.4(4) . . ?
C12 C7 N2 119.0(4) . . ?
C8 C7 N2 117.6(4) . . ?
C10 C11 C12 119.3(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C9 C10 C11 122.9(4) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C20 O1 H1 106(4) . . ?
C24 O2 H2 109.5 . . ?
O3 N4 O4 120.1(5) . . ?
O3 N4 C19 120.5(5) . . ?
O4 N4 C19 119.4(5) . . ?
C20 C19 C24 119.9(5) . . ?
C20 C19 N4 120.3(5) . . ?
C24 C19 N4 119.7(5) . . ?
O1 C20 C21 116.8(6) . . ?
O1 C20 C19 124.0(5) . . ?
C21 C20 C19 119.2(6) . . ?
C21 C22 C23 123.4(6) . . ?
C21 C22 H22 118.3 . . ?
C23 C22 H22 118.3 . . ?
C22 C21 C20 119.3(6) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C22 C23 C24 119.1(7) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
O2 C24 C23 117.1(6) . . ?
O2 C24 C19 123.8(6) . . ?
C23 C24 C19 119.1(6) . . ?
C2 O5 H5 111(3) . . ?
C6 O6 H6 111(4) . . ?
O8 N3 O7 123.5(4) . . ?
O8 N3 C1 118.8(4) . . ?
O7 N3 C1 117.7(4) . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O5 C2 C3 125.0(4) . . ?
O5 C2 C1 117.6(4) . . ?
C3 C2 C1 117.4(4) . . ?
O6 C6 C5 123.6(4) . . ?
O6 C6 C1 118.1(4) . . ?
C5 C6 C1 118.3(4) . . ?
C6 C1 C2 123.0(4) . . ?
C6 C1 N3 118.0(4) . . ?
C2 C1 N3 119.0(4) . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C18 O10 H10A 112(5) . . ?
C14 O9 H9A 109.5 . . ?
O12 N1 O11 120.2(5) . . ?
O12 N1 C13 119.7(5) . . ?
O11 N1 C13 120.1(5) . . ?
C16 C15 C14 120.8(5) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.2(5) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
O10 C18 C17 116.3(5) . . ?
O10 C18 C13 125.0(5) . . ?
C17 C18 C13 118.7(5) . . ?
C14 C13 C18 121.1(5) . . ?
C14 C13 N1 119.4(5) . . ?
C18 C13 N1 119.5(5) . . ?
C18 C17 C16 119.7(5) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
O9 C14 C15 116.6(5) . . ?
O9 C14 C13 124.9(6) . . ?
C15 C14 C13 118.5(5) . . ?
C26 N5 C31 119.5(4) . . ?
C27 N6 C30 119.4(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N5 C31 C30 120.2(4) . . ?
N5 C31 C32 117.9(4) . . ?
C30 C31 C32 121.9(4) . . ?
N6 C27 C26 120.4(4) . . ?
N6 C27 C28 118.0(4) . . ?
C26 C27 C28 121.6(4) . . ?
N5 C26 C27 120.3(4) . . ?
N5 C26 C25 117.3(4) . . ?
C27 C26 C25 122.4(4) . . ?
N6 C30 C31 120.1(4) . . ?
N6 C30 C29 117.3(4) . . ?
C31 C30 C29 122.6(4) . . ?
C35 N8 C38 119.8(4) . . ?
C34 N7 C39 119.1(4) . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N8 C38 C39 119.7(4) . . ?
N8 C38 C37 117.8(4) . . ?
C39 C38 C37 122.5(4) . . ?
N7 C34 C35 120.6(4) . . ?
N7 C34 C33 117.0(4) . . ?
C35 C34 C33 122.5(4) . . ?
N8 C35 C34 120.1(4) . . ?
N8 C35 C36 117.5(4) . . ?
C34 C35 C36 122.4(4) . . ?
N7 C39 C38 120.8(4) . . ?
N7 C39 C40 117.3(4) . . ?
C38 C39 C40 121.9(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
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
O13 C12 1.341(6) . ?
O13 H13 0.98(7) . ?
O14 C8 1.339(5) . ?
O14 H14 0.75(5) . ?
O15 N2 1.220(5) . ?
O16 N2 1.222(5) . ?
N2 C7 1.463(5) . ?
C12 C7 1.386(6) . ?
C12 C11 1.392(6) . ?
C8 C7 1.403(6) . ?
C8 C9 1.403(6) . ?
C9 C10 1.377(6) . ?
C9 H9 0.9300 . ?
C11 C10 1.388(7) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
O1 C20 1.355(7) . ?
O1 H1 0.79(5) . ?
O2 C24 1.343(8) . ?
O2 H2 0.8200 . ?
O3 N4 1.222(6) . ?
O4 N4 1.244(6) . ?
N4 C19 1.433(7) . ?
C19 C20 1.405(7) . ?
C19 C24 1.428(8) . ?
C20 C21 1.388(8) . ?
C22 C21 1.362(10) . ?
C22 C23 1.375(10) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C23 C24 1.376(9) . ?
C23 H23 0.9300 . ?
O5 C2 1.340(5) . ?
O5 H5 1.04(6) . ?
O6 C6 1.355(5) . ?
O6 H6 0.78(5) . ?
O8 N3 1.219(5) . ?
O7 N3 1.224(5) . ?
N3 C1 1.465(5) . ?
C3 C2 1.384(6) . ?
C3 C4 1.384(6) . ?
C3 H3 0.9300 . ?
C2 C1 1.402(6) . ?
C6 C5 1.387(6) . ?
C6 C1 1.388(6) . ?
C5 C4 1.389(7) . ?
C5 H5A 0.9300 . ?
C4 H4 0.9300 . ?
O10 C18 1.343(6) . ?
O10 H10A 0.80(7) . ?
O12 N1 1.236(6) . ?
O11 N1 1.236(6) . ?
O9 C14 1.344(6) . ?
O9 H9A 0.8200 . ?
N1 C13 1.443(7) . ?
C15 C16 1.377(8) . ?
C15 C14 1.380(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(7) . ?
C16 H16 0.9300 . ?
C18 C17 1.384(7) . ?
C18 C13 1.414(7) . ?
C13 C14 1.405(7) . ?
C17 H17 0.9300 . ?
N5 C26 1.334(6) . ?
N5 C31 1.339(5) . ?
N6 C27 1.334(5) . ?
N6 C30 1.343(6) . ?
C32 C31 1.497(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C28 C27 1.502(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.500(6) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C25 C26 1.497(6) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C31 C30 1.400(6) . ?
C27 C26 1.400(6) . ?
N8 C35 1.338(6) . ?
N8 C38 1.346(6) . ?
N7 C34 1.340(6) . ?
N7 C39 1.343(6) . ?
C37 C38 1.499(6) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C36 C35 1.501(6) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C33 C34 1.496(6) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C38 C39 1.396(6) . ?
C34 C35 1.399(6) . ?
C39 C40 1.504(6) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
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
O14 C8 C9 C10 179.9(4) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
O13 C12 C7 C8 -179.3(4) . . . . ?
C11 C12 C7 C8 -1.9(7) . . . . ?
O13 C12 C7 N2 1.2(6) . . . . ?
C11 C12 C7 N2 178.6(4) . . . . ?
O14 C8 C7 C12 -178.8(4) . . . . ?
C9 C8 C7 C12 1.1(7) . . . . ?
O14 C8 C7 N2 0.7(6) . . . . ?
C9 C8 C7 N2 -179.5(4) . . . . ?
O15 N2 C7 C12 -110.4(5) . . . . ?
O16 N2 C7 C12 67.3(6) . . . . ?
O15 N2 C7 C8 70.1(5) . . . . ?
O16 N2 C7 C8 -112.2(5) . . . . ?
O13 C12 C11 C10 178.9(4) . . . . ?
C7 C12 C11 C10 1.6(7) . . . . ?
C8 C9 C10 C11 -0.3(7) . . . . ?
C12 C11 C10 C9 -0.6(7) . . . . ?
O3 N4 C19 C20 5.3(7) . . . . ?
O4 N4 C19 C20 -175.0(5) . . . . ?
O3 N4 C19 C24 -172.7(4) . . . . ?
O4 N4 C19 C24 6.9(7) . . . . ?
C24 C19 C20 O1 -179.8(5) . . . . ?
N4 C19 C20 O1 2.1(7) . . . . ?
C24 C19 C20 C21 0.1(7) . . . . ?
N4 C19 C20 C21 -177.9(5) . . . . ?
C23 C22 C21 C20 -0.4(9) . . . . ?
O1 C20 C21 C22 -179.9(5) . . . . ?
C19 C20 C21 C22 0.1(8) . . . . ?
C21 C22 C23 C24 0.4(9) . . . . ?
C22 C23 C24 O2 178.8(5) . . . . ?
C22 C23 C24 C19 -0.2(8) . . . . ?
C20 C19 C24 O2 -179.0(5) . . . . ?
N4 C19 C24 O2 -1.0(7) . . . . ?
C20 C19 C24 C23 -0.1(8) . . . . ?
N4 C19 C24 C23 178.0(5) . . . . ?
C4 C3 C2 O5 -177.8(4) . . . . ?
C4 C3 C2 C1 0.4(6) . . . . ?
O6 C6 C1 C2 179.0(4) . . . . ?
C5 C6 C1 C2 0.1(7) . . . . ?
O6 C6 C1 N3 0.1(6) . . . . ?
C5 C6 C1 N3 -178.9(4) . . . . ?
O5 C2 C1 C6 178.1(4) . . . . ?
C3 C2 C1 C6 -0.3(6) . . . . ?
O5 C2 C1 N3 -3.0(6) . . . . ?
C3 C2 C1 N3 178.6(4) . . . . ?
O8 N3 C1 C6 110.2(5) . . . . ?
O7 N3 C1 C6 -68.9(5) . . . . ?
O8 N3 C1 C2 -68.8(5) . . . . ?
O7 N3 C1 C2 112.1(5) . . . . ?
O6 C6 C5 C4 -178.9(4) . . . . ?
C1 C6 C5 C4 0.0(7) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C6 C5 C4 C3 0.1(7) . . . . ?
C14 C15 C16 C17 0.1(8) . . . . ?
O10 C18 C13 C14 -178.2(4) . . . . ?
C17 C18 C13 C14 0.8(7) . . . . ?
O10 C18 C13 N1 1.3(7) . . . . ?
C17 C18 C13 N1 -179.7(4) . . . . ?
O12 N1 C13 C14 -172.9(5) . . . . ?
O11 N1 C13 C14 6.8(7) . . . . ?
O12 N1 C13 C18 7.6(7) . . . . ?
O11 N1 C13 C18 -172.7(5) . . . . ?
O10 C18 C17 C16 179.4(5) . . . . ?
C13 C18 C17 C16 0.3(7) . . . . ?
C15 C16 C17 C18 -0.8(7) . . . . ?
C16 C15 C14 O9 -179.2(5) . . . . ?
C16 C15 C14 C13 1.0(7) . . . . ?
C18 C13 C14 O9 178.7(4) . . . . ?
N1 C13 C14 O9 -0.8(7) . . . . ?
C18 C13 C14 C15 -1.5(7) . . . . ?
N1 C13 C14 C15 179.0(5) . . . . ?
C26 N5 C31 C30 -1.9(6) . . . . ?
C26 N5 C31 C32 178.3(4) . . . . ?
C30 N6 C27 C26 -0.3(6) . . . . ?
C30 N6 C27 C28 179.4(4) . . . . ?
C31 N5 C26 C27 1.7(6) . . . . ?
C31 N5 C26 C25 -178.6(4) . . . . ?
N6 C27 C26 N5 -0.6(6) . . . . ?
C28 C27 C26 N5 179.7(4) . . . . ?
N6 C27 C26 C25 179.8(4) . . . . ?
C28 C27 C26 C25 0.1(7) . . . . ?
C27 N6 C30 C31 0.0(6) . . . . ?
C27 N6 C30 C29 -179.8(4) . . . . ?
N5 C31 C30 N6 1.1(6) . . . . ?
C32 C31 C30 N6 -179.2(4) . . . . ?
N5 C31 C30 C29 -179.1(4) . . . . ?
C32 C31 C30 C29 0.7(7) . . . . ?
C35 N8 C38 C39 -1.3(6) . . . . ?
C35 N8 C38 C37 179.6(4) . . . . ?
C39 N7 C34 C35 -1.5(6) . . . . ?
C39 N7 C34 C33 177.7(4) . . . . ?
C38 N8 C35 C34 0.6(6) . . . . ?
C38 N8 C35 C36 -178.5(4) . . . . ?
N7 C34 C35 N8 0.8(6) . . . . ?
C33 C34 C35 N8 -178.4(4) . . . . ?
N7 C34 C35 C36 179.9(4) . . . . ?
C33 C34 C35 C36 0.7(7) . . . . ?
C34 N7 C39 C38 0.9(6) . . . . ?
C34 N7 C39 C40 -178.3(4) . . . . ?
N8 C38 C39 N7 0.5(6) . . . . ?
C37 C38 C39 N7 179.6(4) . . . . ?
N8 C38 C39 C40 179.7(4) . . . . ?
C37 C38 C39 C40 -1.2(7) . . . . ?
