#------------------------------------------------------------------------------
#$Date: 2020-10-02 07:34:22 +0300 (Fri, 02 Oct 2020) $
#$Revision: 256919 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/13/7241338.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_7241338
loop_
_publ_author_name
'Loke, Shiva K.'
'Pagadala, Eswar'
'Devaraju, S.'
'Srinivasadesikan, V.'
'Kottalanka, Ravi K.'
_publ_section_title
;
 New zinc complexes derived from “self-adaptable” acyclic
 diiminodipyrromethanes as potent catalysts for the reduction of curing
 temperature of bisphenol-A/F benzoxazines
;
_journal_issue                   60
_journal_name_full               'RSC Advances'
_journal_page_first              36275
_journal_page_last               36286
_journal_paper_doi               10.1039/D0RA07837A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C44 H53 N4 O2'
_chemical_formula_weight         669.90
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-11-04 deposited with the CCDC.	2020-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                104.022(4)
_cell_angle_beta                 93.333(5)
_cell_angle_gamma                108.901(4)
_cell_formula_units_Z            2
_cell_length_a                   12.0275(7)
_cell_length_b                   12.8465(6)
_cell_length_c                   14.5982(8)
_cell_measurement_reflns_used    3735
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.3520
_cell_measurement_theta_min      2.6150
_cell_volume                     2047.3(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15950
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.177
_diffrn_reflns_theta_min         2.146
_exptl_absorpt_coefficient_mu    0.067
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       block
_exptl_crystal_F_000             722
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0065(14)
_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   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         9346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0744
_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)+(0.0709P)²+0.5726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.2128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4868
_reflns_number_total             9346
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra07837a2.cif
_cod_data_source_block           shelx
_cod_database_code               7241338
_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_min   0.984
_shelx_estimated_absorpt_t_max   0.989
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
N3 N 0.83984(17) 0.13311(16) 0.85692(14) 0.0460(5) Uani 1 1 d . . . . .
H3 H 0.793469 0.141871 0.814602 0.055 Uiso 1 1 calc R U . . .
N1 N 0.91490(18) 0.16605(17) 0.64990(14) 0.0481(5) Uani 1 1 d . . . . .
H1 H 0.840401 0.151817 0.652691 0.058 Uiso 1 1 calc R U . . .
N4 N 0.70208(19) 0.26889(17) 0.96006(15) 0.0521(5) Uani 1 1 d . . . . .
O1 O 0.67973(19) 0.1379(2) 0.71129(14) 0.0765(6) Uani 1 1 d . . . . .
N2 N 0.8263(2) 0.29891(18) 0.55441(16) 0.0584(6) Uani 1 1 d . . . . .
C28 C 0.9189(2) 0.0782(2) 0.83748(17) 0.0461(6) Uani 1 1 d . . . . .
O2 O 0.6076(3) 0.2641(3) 0.78846(17) 0.1096(9) Uani 1 1 d . . . . .
H2 H 0.640835 0.254991 0.835006 0.164 Uiso 1 1 calc R U . . .
C4 C 0.9315(2) 0.0225(2) 0.73639(17) 0.0472(6) Uani 1 1 d . . . . .
C5 C 0.8117(2) -0.0655(2) 0.68177(18) 0.0495(6) Uani 1 1 d . . . . .
C32 C 0.7774(2) 0.2364(2) 0.99978(18) 0.0519(6) Uani 1 1 d . . . . .
H32 H 0.789342 0.256898 1.066169 0.062 Uiso 1 1 calc R U . . .
C11 C 0.9821(2) 0.1135(2) 0.68605(18) 0.0480(6) Uani 1 1 d . . . . .
C14 C 0.9833(2) 0.2448(2) 0.60849(18) 0.0529(6) Uani 1 1 d . . . . .
C31 C 0.8448(2) 0.1724(2) 0.95360(17) 0.0489(6) Uani 1 1 d . . . . .
C29 C 0.9765(2) 0.0836(2) 0.9236(2) 0.0601(7) Uani 1 1 d . . . . .
H29 H 1.035903 0.053719 0.932166 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7828(2) 0.3625(2) 0.5031(2) 0.0567(7) Uani 1 1 d . . . . .
C33 C 0.6496(2) 0.3399(2) 1.02174(19) 0.0557(7) Uani 1 1 d . . . . .
C6 C 0.7233(2) -0.1193(2) 0.7287(2) 0.0635(7) Uani 1 1 d . . . . .
H6 H 0.734772 -0.098946 0.795118 0.076 Uiso 1 1 calc R U . . .
C17 C 0.7506(2) 0.3208(2) 0.4035(2) 0.0620(7) Uani 1 1 d . . . . .
C15 C 0.9353(3) 0.3106(2) 0.56152(18) 0.0567(7) Uani 1 1 d . . . . .
H15 H 0.986120 0.363643 0.535500 0.068 Uiso 1 1 calc R U . . .
C10 C 0.7921(2) -0.0999(2) 0.5829(2) 0.0603(7) Uani 1 1 d . . . . .
H10 H 0.850411 -0.066328 0.549280 0.072 Uiso 1 1 calc R U . . .
C38 C 0.7195(3) 0.4531(2) 1.0703(2) 0.0657(8) Uani 1 1 d . . . . .
C12 C 1.0952(2) 0.1598(2) 0.6673(2) 0.0629(7) Uani 1 1 d . . . . .
H12 H 1.160211 0.140396 0.683641 0.075 Uiso 1 1 calc R U . . .
C3 C 1.0180(2) -0.0431(2) 0.7402(2) 0.0630(7) Uani 1 1 d . . . . .
H3A H 1.093553 0.009065 0.775163 0.094 Uiso 1 1 calc R U . . .
H3B H 1.027772 -0.077283 0.676439 0.094 Uiso 1 1 calc R U . . .
H3C H 0.986373 -0.101816 0.771362 0.094 Uiso 1 1 calc R U . . .
C1 C 0.6176(3) 0.1944(3) 0.7114(2) 0.0647(8) Uani 1 1 d . . . . .
C34 C 0.5281(3) 0.2950(3) 1.0266(2) 0.0699(8) Uani 1 1 d . . . . .
C18 C 0.7025(3) 0.3816(3) 0.3571(3) 0.0750(9) Uani 1 1 d . . . . .
H18 H 0.682226 0.356427 0.291052 0.090 Uiso 1 1 calc R U . . .
C13 C 1.0953(3) 0.2414(3) 0.6191(2) 0.0678(8) Uani 1 1 d . . . . .
H13 H 1.160726 0.285879 0.597871 0.081 Uiso 1 1 calc R U . . .
C21 C 0.7635(3) 0.4606(2) 0.5550(2) 0.0656(8) Uani 1 1 d . . . . .
C30 C 0.9299(3) 0.1416(2) 0.9956(2) 0.0632(7) Uani 1 1 d . . . . .
H30 H 0.952563 0.156988 1.060877 0.076 Uiso 1 1 calc R U . . .
C25 C 0.7655(3) 0.2101(3) 0.3499(2) 0.0718(8) Uani 1 1 d . . . . .
H25 H 0.843866 0.212589 0.375299 0.086 Uiso 1 1 calc R U . . .
C7 C 0.6189(3) -0.2023(3) 0.6790(3) 0.0763(9) Uani 1 1 d . . . . .
H7 H 0.560610 -0.237070 0.712048 0.092 Uiso 1 1 calc R U . . .
C9 C 0.6872(3) -0.1836(3) 0.5335(2) 0.0712(8) Uani 1 1 d . . . . .
H9 H 0.675904 -0.205703 0.467152 0.085 Uiso 1 1 calc R U . . .
C20 C 0.7135(3) 0.5171(3) 0.5038(3) 0.0822(10) Uani 1 1 d . . . . .
H20 H 0.699823 0.582510 0.536430 0.099 Uiso 1 1 calc R U . . .
C8 C 0.5997(3) -0.2343(3) 0.5807(3) 0.0742(9) Uani 1 1 d . . . . .
H8 H 0.528593 -0.289503 0.547104 0.089 Uiso 1 1 calc R U . . .
C42 C 0.4537(3) 0.1727(3) 0.9704(3) 0.0851(10) Uani 1 1 d . . . . .
C22 C 0.7984(3) 0.5044(3) 0.6620(3) 0.0834(10) Uani 1 1 d . . . . .
H22 H 0.804928 0.440530 0.684790 0.100 Uiso 1 1 calc R U . . .
C37 C 0.6646(3) 0.5184(3) 1.1275(3) 0.0929(11) Uani 1 1 d . . . . .
H37 H 0.709011 0.593383 1.161594 0.111 Uiso 1 1 calc R U . . .
C2 C 0.5463(3) 0.1927(4) 0.6246(2) 0.0949(12) Uani 1 1 d . . . . .
H2A H 0.593905 0.247213 0.595003 0.142 Uiso 1 1 calc R U . . .
H2B H 0.478262 0.212171 0.641792 0.142 Uiso 1 1 calc R U . . .
H2C H 0.520491 0.117499 0.580817 0.142 Uiso 1 1 calc R U . . .
C39 C 0.8471(3) 0.5069(3) 1.0563(2) 0.0769(9) Uani 1 1 d . . . . .
H39 H 0.873595 0.444300 1.025064 0.092 Uiso 1 1 calc R U . . .
C35 C 0.4801(3) 0.3662(3) 1.0853(3) 0.0979(12) Uani 1 1 d . . . . .
H35 H 0.399939 0.338377 1.090926 0.118 Uiso 1 1 calc R U . . .
C27 C 0.7629(4) 0.1948(4) 0.2429(2) 0.1018(12) Uani 1 1 d . . . . .
H27A H 0.685453 0.187116 0.214824 0.153 Uiso 1 1 calc R U . . .
H27B H 0.780261 0.127287 0.214464 0.153 Uiso 1 1 calc R U . . .
H27C H 0.821235 0.260351 0.232068 0.153 Uiso 1 1 calc R U . . .
C19 C 0.6842(3) 0.4785(3) 0.4069(3) 0.0867(11) Uani 1 1 d . . . . .
H19 H 0.651532 0.518100 0.374250 0.104 Uiso 1 1 calc R U . . .
C36 C 0.5468(4) 0.4753(4) 1.1349(3) 0.1087(14) Uani 1 1 d . . . . .
H36 H 0.512182 0.520719 1.174066 0.130 Uiso 1 1 calc R U . . .
C26 C 0.6738(4) 0.1070(3) 0.3685(3) 0.1081(13) Uani 1 1 d . . . . .
H26A H 0.680004 0.115231 0.435975 0.162 Uiso 1 1 calc R U . . .
H26B H 0.687834 0.038642 0.336827 0.162 Uiso 1 1 calc R U . . .
H26C H 0.595622 0.101915 0.344614 0.162 Uiso 1 1 calc R U . . .
C24 C 0.9185(4) 0.5976(4) 0.6885(3) 0.1390(19) Uani 1 1 d . . . . .
H24A H 0.976389 0.569085 0.659562 0.209 Uiso 1 1 calc R U . . .
H24B H 0.940207 0.621962 0.756685 0.209 Uiso 1 1 calc R U . . .
H24C H 0.915742 0.661321 0.666304 0.209 Uiso 1 1 calc R U . . .
C23 C 0.7046(5) 0.5434(5) 0.7123(3) 0.1428(19) Uani 1 1 d . . . . .
H23A H 0.701718 0.610973 0.696658 0.214 Uiso 1 1 calc R U . . .
H23B H 0.725071 0.559982 0.780094 0.214 Uiso 1 1 calc R U . . .
H23C H 0.628318 0.483666 0.691563 0.214 Uiso 1 1 calc R U . . .
C40 C 0.9314(4) 0.5730(6) 1.1465(4) 0.188(3) Uani 1 1 d . . . . .
H40A H 0.908145 0.635226 1.179187 0.283 Uiso 1 1 calc R U . . .
H40B H 1.010307 0.602619 1.131703 0.283 Uiso 1 1 calc R U . . .
H40C H 0.930020 0.523513 1.186640 0.283 Uiso 1 1 calc R U . . .
C41 C 0.8512(4) 0.5789(6) 0.9887(5) 0.198(3) Uani 1 1 d . . . . .
H41A H 0.791921 0.535993 0.933665 0.297 Uiso 1 1 calc R U . . .
H41B H 0.928342 0.600076 0.969135 0.297 Uiso 1 1 calc R U . . .
H41C H 0.835922 0.646657 1.020049 0.297 Uiso 1 1 calc R U . . .
C44 C 0.3485(5) 0.1715(5) 0.9062(5) 0.195(3) Uani 1 1 d . . . A -1
H44A H 0.293700 0.193682 0.944868 0.292 Uiso 1 1 calc R U . A -1
H44B H 0.309365 0.095813 0.864480 0.292 Uiso 1 1 calc R U . A -1
H44C H 0.376258 0.224284 0.868879 0.292 Uiso 1 1 calc R U . A -1
C43 C 0.4129(6) 0.1011(4) 1.0382(4) 0.212(4) Uani 1 1 d . . . B -1
H43A H 0.480702 0.104577 1.078520 0.317 Uiso 1 1 calc R U . B -1
H43B H 0.370361 0.023108 1.002352 0.317 Uiso 1 1 calc R U . B -1
H43C H 0.361697 0.129946 1.076748 0.317 Uiso 1 1 calc R U . B -1
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
C28 N3 C31 110.2(2) . . ?
C28 N3 H3 124.9 . . ?
C31 N3 H3 124.9 . . ?
C11 N1 C14 110.2(2) . . ?
C11 N1 H1 124.9 . . ?
C14 N1 H1 124.9 . . ?
C32 N4 C33 117.3(2) . . ?
C15 N2 C16 119.8(2) . . ?
N3 C28 C29 107.1(2) . . ?
N3 C28 C4 122.4(2) . . ?
C29 C28 C4 130.4(2) . . ?
C1 O2 H2 109.5 . . ?
C11 C4 C28 109.73(19) . . ?
C11 C4 C5 111.5(2) . . ?
C28 C4 C5 110.9(2) . . ?
C11 C4 C3 108.6(2) . . ?
C28 C4 C3 108.9(2) . . ?
C5 C4 C3 107.1(2) . . ?
C6 C5 C10 117.5(3) . . ?
C6 C5 C4 121.6(2) . . ?
C10 C5 C4 120.6(2) . . ?
N4 C32 C31 127.1(2) . . ?
N4 C32 H32 116.5 . . ?
C31 C32 H32 116.5 . . ?
N1 C11 C12 106.9(2) . . ?
N1 C11 C4 122.6(2) . . ?
C12 C11 C4 130.4(2) . . ?
C13 C14 N1 106.7(2) . . ?
C13 C14 C15 130.7(2) . . ?
N1 C14 C15 122.6(2) . . ?
N3 C31 C30 106.7(2) . . ?
N3 C31 C32 125.8(2) . . ?
C30 C31 C32 127.5(2) . . ?
C28 C29 C30 107.8(2) . . ?
C28 C29 H29 126.1 . . ?
C30 C29 H29 126.1 . . ?
C21 C16 C17 121.5(3) . . ?
C21 C16 N2 118.4(3) . . ?
C17 C16 N2 119.8(2) . . ?
C34 C33 C38 122.0(3) . . ?
C34 C33 N4 118.5(2) . . ?
C38 C33 N4 119.4(2) . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C25 121.6(3) . . ?
C16 C17 C25 120.3(2) . . ?
N2 C15 C14 122.3(2) . . ?
N2 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C9 C10 C5 120.8(3) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C37 C38 C33 117.2(3) . . ?
C37 C38 C39 120.2(3) . . ?
C33 C38 C39 122.4(3) . . ?
C11 C12 C13 107.7(2) . . ?
C11 C12 H12 126.1 . . ?
C13 C12 H12 126.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C1 O2 122.6(3) . . ?
O1 C1 C2 123.8(3) . . ?
O2 C1 C2 113.5(3) . . ?
C35 C34 C33 117.0(3) . . ?
C35 C34 C42 122.3(3) . . ?
C33 C34 C42 120.7(3) . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C14 C13 C12 108.4(2) . . ?
C14 C13 H13 125.8 . . ?
C12 C13 H13 125.8 . . ?
C20 C21 C16 117.4(3) . . ?
C20 C21 C22 121.6(3) . . ?
C16 C21 C22 121.0(3) . . ?
C31 C30 C29 108.2(2) . . ?
C31 C30 H30 125.9 . . ?
C29 C30 H30 125.9 . . ?
C17 C25 C26 111.1(3) . . ?
C17 C25 C27 113.8(3) . . ?
C26 C25 C27 110.3(3) . . ?
C17 C25 H25 107.1 . . ?
C26 C25 H25 107.1 . . ?
C27 C25 H25 107.1 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C43 C42 C44 111.2(4) . . ?
C43 C42 C34 109.8(3) . . ?
C44 C42 C34 110.4(3) . . ?
C24 C22 C21 111.0(3) . . ?
C24 C22 C23 111.4(4) . . ?
C21 C22 C23 112.5(3) . . ?
C24 C22 H22 107.2 . . ?
C21 C22 H22 107.2 . . ?
C23 C22 H22 107.2 . . ?
C36 C37 C38 121.6(3) . . ?
C36 C37 H37 119.2 . . ?
C38 C37 H37 119.2 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C40 C39 C41 111.5(4) . . ?
C40 C39 C38 114.6(3) . . ?
C41 C39 C38 109.2(3) . . ?
C40 C39 H39 107.1 . . ?
C41 C39 H39 107.1 . . ?
C38 C39 H39 107.1 . . ?
C36 C35 C34 121.9(3) . . ?
C36 C35 H35 119.0 . . ?
C34 C35 H35 119.0 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C35 C36 C37 120.2(3) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 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
N3 C28 1.360(3) . ?
N3 C31 1.370(3) . ?
N3 H3 0.8600 . ?
N1 C11 1.365(3) . ?
N1 C14 1.371(3) . ?
N1 H1 0.8600 . ?
N4 C32 1.278(3) . ?
N4 C33 1.443(3) . ?
O1 C1 1.198(3) . ?
N2 C15 1.265(3) . ?
N2 C16 1.425(3) . ?
C28 C29 1.375(3) . ?
C28 C4 1.516(3) . ?
O2 C1 1.295(4) . ?
O2 H2 0.8200 . ?
C4 C11 1.512(3) . ?
C4 C5 1.537(3) . ?
C4 C3 1.542(3) . ?
C5 C6 1.384(3) . ?
C5 C10 1.385(4) . ?
C32 C31 1.419(3) . ?
C32 H32 0.9300 . ?
C11 C12 1.370(3) . ?
C14 C13 1.363(4) . ?
C14 C15 1.439(4) . ?
C31 C30 1.375(3) . ?
C29 C30 1.390(4) . ?
C29 H29 0.9300 . ?
C16 C21 1.401(4) . ?
C16 C17 1.405(4) . ?
C33 C34 1.400(4) . ?
C33 C38 1.401(4) . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C17 C18 1.380(4) . ?
C17 C25 1.520(4) . ?
C15 H15 0.9300 . ?
C10 C9 1.381(4) . ?
C10 H10 0.9300 . ?
C38 C37 1.386(4) . ?
C38 C39 1.515(4) . ?
C12 C13 1.395(4) . ?
C12 H12 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C1 C2 1.479(4) . ?
C34 C35 1.386(4) . ?
C34 C42 1.524(4) . ?
C18 C19 1.373(5) . ?
C18 H18 0.9300 . ?
C13 H13 0.9300 . ?
C21 C20 1.393(4) . ?
C21 C22 1.509(5) . ?
C30 H30 0.9300 . ?
C25 C26 1.520(4) . ?
C25 C27 1.523(4) . ?
C25 H25 0.9800 . ?
C7 C8 1.376(4) . ?
C7 H7 0.9300 . ?
C9 C8 1.365(4) . ?
C9 H9 0.9300 . ?
C20 C19 1.365(5) . ?
C20 H20 0.9300 . ?
C8 H8 0.9300 . ?
C42 C43 1.507(6) . ?
C42 C44 1.523(6) . ?
C22 C24 1.504(5) . ?
C22 C23 1.532(5) . ?
C22 H22 0.9800 . ?
C37 C36 1.365(5) . ?
C37 H37 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C39 C40 1.493(5) . ?
C39 C41 1.500(6) . ?
C39 H39 0.9800 . ?
C35 C36 1.358(5) . ?
C35 H35 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C19 H19 0.9300 . ?
C36 H36 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
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
N3 H3 O1 0.86 1.96 2.810(3) 171.8 . yes
N1 H1 O1 0.86 2.13 2.954(3) 159.9 . yes
O2 H2 N4 0.82 1.87 2.668(3) 163.1 . 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
C31 N3 C28 C29 -0.6(3) . . . . ?
C31 N3 C28 C4 178.3(2) . . . . ?
N3 C28 C4 C11 67.5(3) . . . . ?
C29 C28 C4 C11 -113.8(3) . . . . ?
N3 C28 C4 C5 -56.1(3) . . . . ?
C29 C28 C4 C5 122.5(3) . . . . ?
N3 C28 C4 C3 -173.7(2) . . . . ?
C29 C28 C4 C3 5.0(4) . . . . ?
C11 C4 C5 C6 -147.9(2) . . . . ?
C28 C4 C5 C6 -25.3(3) . . . . ?
C3 C4 C5 C6 93.4(3) . . . . ?
C11 C4 C5 C10 37.0(3) . . . . ?
C28 C4 C5 C10 159.6(2) . . . . ?
C3 C4 C5 C10 -81.7(3) . . . . ?
C33 N4 C32 C31 -176.0(2) . . . . ?
C14 N1 C11 C12 0.0(3) . . . . ?
C14 N1 C11 C4 179.9(2) . . . . ?
C28 C4 C11 N1 -78.1(3) . . . . ?
C5 C4 C11 N1 45.1(3) . . . . ?
C3 C4 C11 N1 162.9(2) . . . . ?
C28 C4 C11 C12 101.7(3) . . . . ?
C5 C4 C11 C12 -135.1(3) . . . . ?
C3 C4 C11 C12 -17.3(4) . . . . ?
C11 N1 C14 C13 -0.1(3) . . . . ?
C11 N1 C14 C15 177.9(2) . . . . ?
C28 N3 C31 C30 0.4(3) . . . . ?
C28 N3 C31 C32 178.1(2) . . . . ?
N4 C32 C31 N3 -0.6(4) . . . . ?
N4 C32 C31 C30 176.7(3) . . . . ?
N3 C28 C29 C30 0.6(3) . . . . ?
C4 C28 C29 C30 -178.2(2) . . . . ?
C15 N2 C16 C21 -100.9(3) . . . . ?
C15 N2 C16 C17 84.6(3) . . . . ?
C32 N4 C33 C34 -113.0(3) . . . . ?
C32 N4 C33 C38 70.7(3) . . . . ?
C10 C5 C6 C7 -1.3(4) . . . . ?
C4 C5 C6 C7 -176.6(3) . . . . ?
C21 C16 C17 C18 2.1(4) . . . . ?
N2 C16 C17 C18 176.4(2) . . . . ?
C21 C16 C17 C25 -176.2(3) . . . . ?
N2 C16 C17 C25 -1.9(4) . . . . ?
C16 N2 C15 C14 -177.0(2) . . . . ?
C13 C14 C15 N2 176.5(3) . . . . ?
N1 C14 C15 N2 -0.9(4) . . . . ?
C6 C5 C10 C9 1.1(4) . . . . ?
C4 C5 C10 C9 176.4(2) . . . . ?
C34 C33 C38 C37 2.8(5) . . . . ?
N4 C33 C38 C37 179.0(3) . . . . ?
C34 C33 C38 C39 -172.5(3) . . . . ?
N4 C33 C38 C39 3.7(4) . . . . ?
N1 C11 C12 C13 0.0(3) . . . . ?
C4 C11 C12 C13 -179.8(3) . . . . ?
C38 C33 C34 C35 -2.8(5) . . . . ?
N4 C33 C34 C35 -179.0(3) . . . . ?
C38 C33 C34 C42 178.0(3) . . . . ?
N4 C33 C34 C42 1.8(4) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
C25 C17 C18 C19 176.8(3) . . . . ?
N1 C14 C13 C12 0.1(3) . . . . ?
C15 C14 C13 C12 -177.6(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C17 C16 C21 C20 -1.4(4) . . . . ?
N2 C16 C21 C20 -175.8(2) . . . . ?
C17 C16 C21 C22 180.0(3) . . . . ?
N2 C16 C21 C22 5.6(4) . . . . ?
N3 C31 C30 C29 0.1(3) . . . . ?
C32 C31 C30 C29 -177.6(2) . . . . ?
C28 C29 C30 C31 -0.4(3) . . . . ?
C18 C17 C25 C26 -105.9(3) . . . . ?
C16 C17 C25 C26 72.3(4) . . . . ?
C18 C17 C25 C27 19.2(4) . . . . ?
C16 C17 C25 C27 -162.6(3) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C5 C10 C9 C8 0.2(4) . . . . ?
C16 C21 C20 C19 0.1(5) . . . . ?
C22 C21 C20 C19 178.7(3) . . . . ?
C10 C9 C8 C7 -1.3(5) . . . . ?
C6 C7 C8 C9 1.1(5) . . . . ?
C35 C34 C42 C43 -66.2(5) . . . . ?
C33 C34 C42 C43 113.0(4) . . . . ?
C35 C34 C42 C44 56.7(5) . . . . ?
C33 C34 C42 C44 -124.1(4) . . . . ?
C20 C21 C22 C24 -82.3(4) . . . . ?
C16 C21 C22 C24 96.2(4) . . . . ?
C20 C21 C22 C23 43.2(4) . . . . ?
C16 C21 C22 C23 -138.2(3) . . . . ?
C33 C38 C37 C36 -1.2(6) . . . . ?
C39 C38 C37 C36 174.2(4) . . . . ?
C37 C38 C39 C40 50.1(5) . . . . ?
C33 C38 C39 C40 -134.7(4) . . . . ?
C37 C38 C39 C41 -75.6(5) . . . . ?
C33 C38 C39 C41 99.5(4) . . . . ?
C33 C34 C35 C36 1.1(6) . . . . ?
C42 C34 C35 C36 -179.7(4) . . . . ?
C21 C20 C19 C18 0.6(5) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C34 C35 C36 C37 0.4(7) . . . . ?
C38 C37 C36 C35 -0.3(7) . . . . ?
