#------------------------------------------------------------------------------
#$Date: 2022-04-20 00:56:31 +0300 (Wed, 20 Apr 2022) $
#$Revision: 274582 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/99/7129992.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_7129992
loop_
_publ_author_name
'Sarkar, Tanumay'
'Maharana, Prabhat Kumar'
'Roy, Subhasish'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Expedient Ni-catalyzed C-H/C-H cross-dehydrogenative coupling of aryl
 amides with azoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01097F
_journal_year                    2022
_chemical_formula_sum            'C24 H19 N3 O3'
_chemical_formula_weight         397.42
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-17 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.862(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.661(2)
_cell_length_b                   21.437(3)
_cell_length_c                   12.3333(18)
_cell_measurement_reflns_used    4577
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.72
_cell_measurement_theta_min      2.60
_cell_volume                     3842.8(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.1404
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31382
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.401
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.984
_exptl_transmission_factor_min   0.977
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.012(2)
_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   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         6550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.2080
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4713
_reflns_number_total             6550
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc01097f2.cif
_cod_data_source_block           TS-OXA_0m
_cod_original_cell_volume        3842.8(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7129992
_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.
;
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 0.94167(14) 0.15565(8) 0.18767(17) 0.0546(5) Uani 1 1 d . . . . .
O2 O 0.77609(13) 0.15657(8) -0.02316(16) 0.0522(5) Uani 1 1 d . . . . .
O3 O 0.87225(16) -0.00215(9) 0.58762(17) 0.0639(6) Uani 1 1 d . . . . .
N1 N 0.89919(16) 0.08799(10) 0.30133(18) 0.0473(6) Uani 1 1 d . . . . .
H2N H 0.875163 0.051669 0.298634 0.057 Uiso 1 1 calc R U . . .
N2 N 0.84392(16) 0.14268(10) -0.15129(19) 0.0491(6) Uani 1 1 d . . . . .
N3 N 0.86324(17) -0.01284(10) 0.4049(2) 0.0522(6) Uani 1 1 d . . . . .
C1 C 0.6849(2) 0.25068(15) -0.1123(3) 0.0663(9) Uani 1 1 d . . . . .
H1N H 0.657048 0.255166 -0.057994 0.080 Uiso 1 1 calc R U . . .
C2 C 0.6667(2) 0.29044(15) -0.2058(3) 0.0673(9) Uani 1 1 d . . . . .
H2 H 0.625320 0.322982 -0.215061 0.081 Uiso 1 1 calc R U . . .
C3 C 0.7080(2) 0.28346(14) -0.2861(3) 0.0625(9) Uani 1 1 d . . . . .
H3 H 0.694085 0.311395 -0.348045 0.075 Uiso 1 1 calc R U . . .
C4 C 0.7690(2) 0.23630(13) -0.2765(2) 0.0561(8) Uani 1 1 d . . . . .
H4 H 0.796924 0.231598 -0.330624 0.067 Uiso 1 1 calc R U . . .
C5 C 0.78774(18) 0.19561(12) -0.1828(2) 0.0451(7) Uani 1 1 d . . . . .
C6 C 0.74705(19) 0.20383(12) -0.1043(2) 0.0481(7) Uani 1 1 d . . . . .
C7 C 0.83347(18) 0.12210(12) -0.0593(2) 0.0447(6) Uani 1 1 d . . . . .
C8 C 0.86670(17) 0.06207(12) -0.0020(2) 0.0432(6) Uani 1 1 d . . . . .
C9 C 0.85983(18) 0.01176(12) -0.0762(2) 0.0483(7) Uani 1 1 d . . . . .
H9 H 0.839702 0.018999 -0.156182 0.058 Uiso 1 1 calc R U . . .
C10 C 0.88180(19) -0.04861(12) -0.0355(3) 0.0520(7) Uani 1 1 d . . . . .
C11 C 0.9133(2) -0.05778(14) 0.0835(3) 0.0616(8) Uani 1 1 d . . . . .
H11 H 0.929123 -0.097755 0.113532 0.074 Uiso 1 1 calc R U . . .
C12 C 0.9216(2) -0.00863(13) 0.1585(3) 0.0560(8) Uani 1 1 d . . . . .
H12 H 0.943580 -0.016059 0.238517 0.067 Uiso 1 1 calc R U . . .
C13 C 0.89786(18) 0.05190(11) 0.1177(2) 0.0452(6) Uani 1 1 d . . . . .
C14 C 0.8722(3) -0.10232(14) -0.1176(3) 0.0680(9) Uani 1 1 d . . . . .
H14A H 0.857647 -0.086714 -0.195427 0.102 Uiso 1 1 calc R U . . .
H14B H 0.823816 -0.129421 -0.116256 0.102 Uiso 1 1 calc R U . . .
H14C H 0.929000 -0.125109 -0.093629 0.102 Uiso 1 1 calc R U . . .
C15 C 0.91421(18) 0.10451(12) 0.2039(2) 0.0437(6) Uani 1 1 d . . . . .
C16 C 0.91648(17) 0.12051(11) 0.4053(2) 0.0418(6) Uani 1 1 d . . . . .
C17 C 0.94298(19) 0.18317(12) 0.4191(3) 0.0502(7) Uani 1 1 d . . . . .
H17 H 0.949904 0.204888 0.357657 0.060 Uiso 1 1 calc R U . . .
C18 C 0.9587(2) 0.21251(13) 0.5234(3) 0.0567(8) Uani 1 1 d . . . . .
H18 H 0.976459 0.254194 0.531908 0.068 Uiso 1 1 calc R U . . .
C19 C 0.9490(2) 0.18190(14) 0.6154(3) 0.0590(8) Uani 1 1 d . . . . .
H19 H 0.959514 0.202661 0.685433 0.071 Uiso 1 1 calc R U . . .
C20 C 0.92356(19) 0.12042(13) 0.6035(2) 0.0511(7) Uani 1 1 d . . . . .
H20 H 0.917138 0.099518 0.666072 0.061 Uiso 1 1 calc R U . . .
C21 C 0.90715(17) 0.08863(12) 0.4991(2) 0.0439(6) Uani 1 1 d . . . . .
C22 C 0.87994(17) 0.02270(12) 0.4915(2) 0.0453(6) Uani 1 1 d . . . . .
C23 C 0.8377(2) -0.07418(13) 0.4353(3) 0.0590(8) Uani 1 1 d . . . . .
H23A H 0.878601 -0.106293 0.427294 0.071 Uiso 1 1 calc R U . . .
H23B H 0.774952 -0.084676 0.386099 0.071 Uiso 1 1 calc R U . . .
C24 C 0.8474(2) -0.06718(13) 0.5606(3) 0.0584(8) Uani 1 1 d . . . . .
H24A H 0.789990 -0.076741 0.569801 0.070 Uiso 1 1 calc R U . . .
H24B H 0.895132 -0.094508 0.610860 0.070 Uiso 1 1 calc R U . . .
O4 O 0.33243(16) 0.15817(11) 0.8175(2) 0.0744(7) Uani 1 1 d . . . . .
O5 O 0.48085(16) 0.19310(9) 0.72788(18) 0.0627(6) Uani 1 1 d . . . . .
O6 O 0.33469(15) -0.02497(9) 0.35691(16) 0.0603(6) Uani 1 1 d . . . . .
N4 N 0.39554(13) 0.17956(8) 1.00777(16) 0.0349(5) Uani 1 1 d . . . . .
N5 N 0.45731(16) 0.09968(9) 0.63402(17) 0.0451(6) Uani 1 1 d . . . . .
H5 H 0.452729 0.060468 0.645534 0.054 Uiso 1 1 calc R U . . .
N6 N 0.38633(16) -0.01231(9) 0.54977(19) 0.0476(6) Uani 1 1 d . . . . .
C25 C 0.1883(2) 0.22164(16) 0.7805(3) 0.0690(9) Uani 1 1 d . . . . .
H25 H 0.160867 0.213721 0.700760 0.083 Uiso 1 1 calc R U . . .
C26 C 0.1468(2) 0.25889(14) 0.8365(3) 0.0641(9) Uani 1 1 d . . . . .
H26 H 0.090138 0.276892 0.793943 0.077 Uiso 1 1 calc R U . . .
C27 C 0.1869(2) 0.27024(13) 0.9539(3) 0.0614(8) Uani 1 1 d . . . . .
H27 H 0.155972 0.295340 0.988822 0.074 Uiso 1 1 calc R U . . .
C28 C 0.2713(2) 0.24590(14) 1.0224(3) 0.0611(8) Uani 1 1 d . . . . .
H28 H 0.298919 0.254168 1.101925 0.073 Uiso 1 1 calc R U . . .
C29 C 0.31120(18) 0.20885(12) 0.9648(2) 0.0477(7) Uani 1 1 d . . . . .
C30 C 0.27262(19) 0.19629(12) 0.8474(2) 0.0498(7) Uani 1 1 d . . . . .
C31 C 0.40245(18) 0.15071(12) 0.9141(2) 0.0452(6) Uani 1 1 d . . . . .
C32 C 0.48448(17) 0.11356(11) 0.9321(2) 0.0414(6) Uani 1 1 d . . . . .
C33 C 0.53103(18) 0.08717(12) 1.0423(2) 0.0458(6) Uani 1 1 d . . . . .
H33 H 0.511116 0.096195 1.102764 0.055 Uiso 1 1 calc R U . . .
C34 C 0.60596(18) 0.04799(12) 1.0637(2) 0.0463(7) Uani 1 1 d . . . . .
C35 C 0.63284(19) 0.03452(13) 0.9720(3) 0.0511(7) Uani 1 1 d . . . . .
H35 H 0.681673 0.007301 0.983461 0.061 Uiso 1 1 calc R U . . .
C36 C 0.58847(19) 0.06075(12) 0.8636(2) 0.0482(7) Uani 1 1 d . . . . .
H36 H 0.608115 0.051120 0.803056 0.058 Uiso 1 1 calc R U . . .
C37 C 0.51513(18) 0.10120(11) 0.8429(2) 0.0425(6) Uani 1 1 d . . . . .
C38 C 0.6565(2) 0.02272(15) 1.1830(3) 0.0640(9) Uani 1 1 d . . . . .
H38A H 0.700989 0.052769 1.228183 0.096 Uiso 1 1 calc R U . . .
H38B H 0.687336 -0.015145 1.177417 0.096 Uiso 1 1 calc R U . . .
H38C H 0.613783 0.014252 1.220305 0.096 Uiso 1 1 calc R U . . .
C39 C 0.48083(18) 0.13655(12) 0.7298(2) 0.0437(6) Uani 1 1 d . . . . .
C40 C 0.43957(18) 0.11757(11) 0.5186(2) 0.0429(6) Uani 1 1 d . . . . .
C41 C 0.40033(18) 0.07399(12) 0.4292(2) 0.0436(6) Uani 1 1 d . . . . .
C42 C 0.3874(2) 0.09113(14) 0.3155(2) 0.0575(8) Uani 1 1 d . . . . .
H42 H 0.361377 0.062669 0.255285 0.069 Uiso 1 1 calc R U . . .
C43 C 0.4120(3) 0.14904(15) 0.2902(3) 0.0664(9) Uani 1 1 d . . . . .
H43 H 0.402801 0.159627 0.213569 0.080 Uiso 1 1 calc R U . . .
C44 C 0.4504(3) 0.19140(14) 0.3788(3) 0.0672(9) Uani 1 1 d . . . . .
H44 H 0.467137 0.230692 0.361459 0.081 Uiso 1 1 calc R U . . .
C45 C 0.4644(2) 0.17658(12) 0.4913(3) 0.0560(8) Uani 1 1 d . . . . .
H45 H 0.490421 0.205715 0.550327 0.067 Uiso 1 1 calc R U . . .
C46 C 0.37486(17) 0.01124(11) 0.4522(2) 0.0416(6) Uani 1 1 d . . . . .
C47 C 0.3168(2) -0.08448(14) 0.3994(3) 0.0604(8) Uani 1 1 d . . . . .
H47A H 0.349917 -0.117701 0.378514 0.073 Uiso 1 1 calc R U . . .
H47B H 0.251610 -0.094030 0.367775 0.073 Uiso 1 1 calc R U . . .
C48 C 0.3512(2) -0.07609(12) 0.5299(3) 0.0545(7) Uani 1 1 d . . . . .
H48A H 0.301566 -0.081558 0.558220 0.065 Uiso 1 1 calc R U . . .
H48B H 0.399565 -0.105803 0.569070 0.065 Uiso 1 1 calc R U . . .
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
C7 O2 C6 104.0(2) . . ?
C22 O3 C24 106.4(2) . . ?
C15 N1 C16 130.3(2) . . ?
C15 N1 H2N 114.9 . . ?
C16 N1 H2N 114.9 . . ?
C7 N2 C5 104.5(2) . . ?
C22 N3 C23 108.5(2) . . ?
C2 C1 C6 115.6(3) . . ?
C2 C1 H1N 122.2 . . ?
C6 C1 H1N 122.2 . . ?
C1 C2 C3 122.0(3) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 117.5(3) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 N2 108.7(2) . . ?
C4 C5 N2 131.1(3) . . ?
C5 C6 C1 123.5(3) . . ?
C5 C6 O2 107.9(2) . . ?
C1 C6 O2 128.5(3) . . ?
N2 C7 O2 114.9(2) . . ?
N2 C7 C8 126.1(3) . . ?
O2 C7 C8 118.5(2) . . ?
C13 C8 C9 119.2(2) . . ?
C13 C8 C7 124.8(2) . . ?
C9 C8 C7 115.8(2) . . ?
C10 C9 C8 122.5(3) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C11 C10 C9 117.5(3) . . ?
C11 C10 C14 121.0(3) . . ?
C9 C10 C14 121.5(3) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.7(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C8 C13 C12 118.2(2) . . ?
C8 C13 C15 122.3(2) . . ?
C12 C13 C15 119.4(2) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 N1 124.7(2) . . ?
O1 C15 C13 122.3(3) . . ?
N1 C15 C13 113.0(2) . . ?
N1 C16 C21 118.2(2) . . ?
N1 C16 C17 122.7(2) . . ?
C21 C16 C17 119.2(2) . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 121.5(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 119.0(2) . . ?
C20 C21 C22 118.6(3) . . ?
C16 C21 C22 122.4(2) . . ?
N3 C22 O3 116.7(2) . . ?
N3 C22 C21 126.9(3) . . ?
O3 C22 C21 116.3(2) . . ?
N3 C23 C24 104.0(2) . . ?
N3 C23 H23A 111.0 . . ?
C24 C23 H23A 111.0 . . ?
N3 C23 H23B 111.0 . . ?
C24 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
O3 C24 C23 104.4(2) . . ?
O3 C24 H24A 110.9 . . ?
C23 C24 H24A 110.9 . . ?
O3 C24 H24B 110.9 . . ?
C23 C24 H24B 110.9 . . ?
H24A C24 H24B 108.9 . . ?
C31 O4 C30 104.6(2) . . ?
C46 O6 C47 106.4(2) . . ?
C31 N4 C29 104.5(2) . . ?
C39 N5 C40 127.9(2) . . ?
C39 N5 H5 116.0 . . ?
C40 N5 H5 116.0 . . ?
C46 N6 C48 107.8(2) . . ?
C26 C25 C30 117.1(3) . . ?
C26 C25 H25 121.4 . . ?
C30 C25 H25 121.4 . . ?
C27 C26 C25 121.4(3) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 122.6(3) . . ?
C26 C27 H27 118.7 . . ?
C28 C27 H27 118.7 . . ?
C29 C28 C27 115.0(3) . . ?
C29 C28 H28 122.5 . . ?
C27 C28 H28 122.5 . . ?
C28 C29 C30 123.9(3) . . ?
C28 C29 N4 128.7(2) . . ?
C30 C29 N4 107.4(2) . . ?
C29 C30 C25 120.0(3) . . ?
C29 C30 O4 108.6(2) . . ?
C25 C30 O4 131.3(3) . . ?
O4 C31 N4 114.9(2) . . ?
O4 C31 C32 127.2(2) . . ?
N4 C31 C32 117.9(2) . . ?
C37 C32 C33 119.1(2) . . ?
C37 C32 C31 122.2(2) . . ?
C33 C32 C31 118.7(2) . . ?
C34 C33 C32 121.9(3) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C35 C34 C33 117.8(2) . . ?
C35 C34 C38 121.5(3) . . ?
C33 C34 C38 120.7(3) . . ?
C34 C35 C36 121.0(3) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C35 C36 C37 121.2(3) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C32 C37 C36 119.0(2) . . ?
C32 C37 C39 122.3(2) . . ?
C36 C37 C39 118.2(2) . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O5 C39 N5 124.6(2) . . ?
O5 C39 C37 121.4(2) . . ?
N5 C39 C37 113.8(2) . . ?
N5 C40 C45 121.6(2) . . ?
N5 C40 C41 118.8(2) . . ?
C45 C40 C41 119.5(3) . . ?
C42 C41 C40 118.3(3) . . ?
C42 C41 C46 119.4(2) . . ?
C40 C41 C46 122.2(2) . . ?
C43 C42 C41 121.5(3) . . ?
C43 C42 H42 119.3 . . ?
C41 C42 H42 119.3 . . ?
C42 C43 C44 119.7(3) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C45 C44 C43 120.8(3) . . ?
C45 C44 H44 119.6 . . ?
C43 C44 H44 119.6 . . ?
C44 C45 C40 120.2(3) . . ?
C44 C45 H45 119.9 . . ?
C40 C45 H45 119.9 . . ?
N6 C46 O6 117.2(2) . . ?
N6 C46 C41 127.2(2) . . ?
O6 C46 C41 115.6(2) . . ?
O6 C47 C48 104.0(2) . . ?
O6 C47 H47A 111.0 . . ?
C48 C47 H47A 111.0 . . ?
O6 C47 H47B 111.0 . . ?
C48 C47 H47B 111.0 . . ?
H47A C47 H47B 109.0 . . ?
N6 C48 C47 104.7(2) . . ?
N6 C48 H48A 110.8 . . ?
C47 C48 H48A 110.8 . . ?
N6 C48 H48B 110.8 . . ?
C47 C48 H48B 110.8 . . ?
H48A C48 H48B 108.9 . . ?
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 C15 1.221(3) . ?
O2 C7 1.360(3) . ?
O2 C6 1.377(3) . ?
O3 C22 1.346(3) . ?
O3 C24 1.452(3) . ?
N1 C15 1.354(3) . ?
N1 C16 1.395(3) . ?
N1 H2N 0.8600 . ?
N2 C7 1.283(3) . ?
N2 C5 1.399(3) . ?
N3 C22 1.258(3) . ?
N3 C23 1.463(3) . ?
C1 C2 1.376(4) . ?
C1 C6 1.376(4) . ?
C1 H1N 0.9300 . ?
C2 C3 1.379(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.355(4) . ?
C7 C8 1.467(4) . ?
C8 C13 1.388(4) . ?
C8 C9 1.393(4) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(4) . ?
C10 C14 1.503(4) . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(4) . ?
C12 H12 0.9300 . ?
C13 C15 1.506(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C21 1.397(4) . ?
C16 C17 1.397(4) . ?
C17 C18 1.369(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.469(4) . ?
C23 C24 1.502(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
O4 C31 1.294(3) . ?
O4 C30 1.392(4) . ?
O5 C39 1.213(3) . ?
O6 C46 1.352(3) . ?
O6 C47 1.445(4) . ?
N4 C31 1.350(3) . ?
N4 C29 1.378(3) . ?
N5 C39 1.354(3) . ?
N5 C40 1.398(3) . ?
N5 H5 0.8600 . ?
N6 C46 1.255(3) . ?
N6 C48 1.460(3) . ?
C25 C26 1.368(4) . ?
C25 C30 1.382(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.379(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.362(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(4) . ?
C31 C32 1.457(4) . ?
C32 C37 1.380(4) . ?
C32 C33 1.400(4) . ?
C33 C34 1.386(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.377(4) . ?
C34 C38 1.489(4) . ?
C35 C36 1.377(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.385(4) . ?
C36 H36 0.9300 . ?
C37 C39 1.500(4) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C40 C45 1.401(4) . ?
C40 C41 1.401(4) . ?
C41 C42 1.389(4) . ?
C41 C46 1.460(4) . ?
C42 C43 1.370(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.374(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.360(4) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C47 C48 1.506(4) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
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
C6 C1 C2 C3 0.2(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 N2 178.0(3) . . . . ?
C7 N2 C5 C6 0.8(3) . . . . ?
C7 N2 C5 C4 -178.1(3) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
N2 C5 C6 C1 -177.7(3) . . . . ?
C4 C5 C6 O2 178.7(2) . . . . ?
N2 C5 C6 O2 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
C2 C1 C6 O2 -177.8(3) . . . . ?
C7 O2 C6 C5 -0.2(3) . . . . ?
C7 O2 C6 C1 177.0(3) . . . . ?
C5 N2 C7 O2 -0.9(3) . . . . ?
C5 N2 C7 C8 170.2(2) . . . . ?
C6 O2 C7 N2 0.7(3) . . . . ?
C6 O2 C7 C8 -171.1(2) . . . . ?
N2 C7 C8 C13 145.6(3) . . . . ?
O2 C7 C8 C13 -43.6(4) . . . . ?
N2 C7 C8 C9 -38.8(4) . . . . ?
O2 C7 C8 C9 132.0(3) . . . . ?
C13 C8 C9 C10 0.9(4) . . . . ?
C7 C8 C9 C10 -175.0(3) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C8 C9 C10 C14 178.9(3) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C14 C10 C11 C12 -179.7(3) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C9 C8 C13 C12 0.4(4) . . . . ?
C7 C8 C13 C12 175.8(3) . . . . ?
C9 C8 C13 C15 175.1(2) . . . . ?
C7 C8 C13 C15 -9.4(4) . . . . ?
C11 C12 C13 C8 -1.1(5) . . . . ?
C11 C12 C13 C15 -176.0(3) . . . . ?
C16 N1 C15 O1 -5.4(4) . . . . ?
C16 N1 C15 C13 171.9(2) . . . . ?
C8 C13 C15 O1 -33.7(4) . . . . ?
C12 C13 C15 O1 140.9(3) . . . . ?
C8 C13 C15 N1 148.9(3) . . . . ?
C12 C13 C15 N1 -36.4(3) . . . . ?
C15 N1 C16 C21 -170.4(3) . . . . ?
C15 N1 C16 C17 9.3(4) . . . . ?
N1 C16 C17 C18 179.8(2) . . . . ?
C21 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C19 C20 C21 C16 -0.3(4) . . . . ?
C19 C20 C21 C22 -179.9(3) . . . . ?
N1 C16 C21 C20 -179.6(2) . . . . ?
C17 C16 C21 C20 0.7(4) . . . . ?
N1 C16 C21 C22 0.0(4) . . . . ?
C17 C16 C21 C22 -179.7(2) . . . . ?
C23 N3 C22 O3 0.7(3) . . . . ?
C23 N3 C22 C21 -179.3(2) . . . . ?
C24 O3 C22 N3 1.4(3) . . . . ?
C24 O3 C22 C21 -178.5(2) . . . . ?
C20 C21 C22 N3 -179.5(3) . . . . ?
C16 C21 C22 N3 1.0(4) . . . . ?
C20 C21 C22 O3 0.5(4) . . . . ?
C16 C21 C22 O3 -179.1(2) . . . . ?
C22 N3 C23 C24 -2.5(3) . . . . ?
C22 O3 C24 C23 -2.8(3) . . . . ?
N3 C23 C24 O3 3.1(3) . . . . ?
C30 C25 C26 C27 -0.4(5) . . . . ?
C25 C26 C27 C28 0.9(5) . . . . ?
C26 C27 C28 C29 -1.0(5) . . . . ?
C27 C28 C29 C30 0.7(5) . . . . ?
C27 C28 C29 N4 178.0(3) . . . . ?
C31 N4 C29 C28 -178.1(3) . . . . ?
C31 N4 C29 C30 -0.5(3) . . . . ?
C28 C29 C30 C25 -0.2(5) . . . . ?
N4 C29 C30 C25 -178.0(3) . . . . ?
C28 C29 C30 O4 178.8(3) . . . . ?
N4 C29 C30 O4 1.0(3) . . . . ?
C26 C25 C30 C29 0.0(5) . . . . ?
C26 C25 C30 O4 -178.7(3) . . . . ?
C31 O4 C30 C29 -1.1(3) . . . . ?
C31 O4 C30 C25 177.7(3) . . . . ?
C30 O4 C31 N4 0.9(3) . . . . ?
C30 O4 C31 C32 178.7(3) . . . . ?
C29 N4 C31 O4 -0.3(3) . . . . ?
C29 N4 C31 C32 -178.3(2) . . . . ?
O4 C31 C32 C37 26.1(4) . . . . ?
N4 C31 C32 C37 -156.1(2) . . . . ?
O4 C31 C32 C33 -150.8(3) . . . . ?
N4 C31 C32 C33 27.0(4) . . . . ?
C37 C32 C33 C34 -1.3(4) . . . . ?
C31 C32 C33 C34 175.7(2) . . . . ?
C32 C33 C34 C35 -1.2(4) . . . . ?
C32 C33 C34 C38 177.4(2) . . . . ?
C33 C34 C35 C36 2.0(4) . . . . ?
C38 C34 C35 C36 -176.6(3) . . . . ?
C34 C35 C36 C37 -0.4(4) . . . . ?
C33 C32 C37 C36 2.9(4) . . . . ?
C31 C32 C37 C36 -174.0(2) . . . . ?
C33 C32 C37 C39 -168.4(2) . . . . ?
C31 C32 C37 C39 14.7(4) . . . . ?
C35 C36 C37 C32 -2.2(4) . . . . ?
C35 C36 C37 C39 169.5(2) . . . . ?
C40 N5 C39 O5 8.2(5) . . . . ?
C40 N5 C39 C37 -167.1(3) . . . . ?
C32 C37 C39 O5 51.3(4) . . . . ?
C36 C37 C39 O5 -120.1(3) . . . . ?
C32 C37 C39 N5 -133.3(3) . . . . ?
C36 C37 C39 N5 55.4(3) . . . . ?
C39 N5 C40 C45 14.7(4) . . . . ?
C39 N5 C40 C41 -168.6(3) . . . . ?
N5 C40 C41 C42 -176.7(3) . . . . ?
C45 C40 C41 C42 0.0(4) . . . . ?
N5 C40 C41 C46 1.9(4) . . . . ?
C45 C40 C41 C46 178.6(3) . . . . ?
C40 C41 C42 C43 0.0(4) . . . . ?
C46 C41 C42 C43 -178.6(3) . . . . ?
C41 C42 C43 C44 0.0(5) . . . . ?
C42 C43 C44 C45 0.0(5) . . . . ?
C43 C44 C45 C40 0.0(5) . . . . ?
N5 C40 C45 C44 176.6(3) . . . . ?
C41 C40 C45 C44 0.0(4) . . . . ?
C48 N6 C46 O6 0.4(3) . . . . ?
C48 N6 C46 C41 -179.4(3) . . . . ?
C47 O6 C46 N6 -0.8(3) . . . . ?
C47 O6 C46 C41 179.1(2) . . . . ?
C42 C41 C46 N6 176.2(3) . . . . ?
C40 C41 C46 N6 -2.4(4) . . . . ?
C42 C41 C46 O6 -3.7(4) . . . . ?
C40 C41 C46 O6 177.7(2) . . . . ?
C46 O6 C47 C48 0.7(3) . . . . ?
C46 N6 C48 C47 0.1(3) . . . . ?
O6 C47 C48 N6 -0.5(3) . . . . ?
