#------------------------------------------------------------------------------
#$Date: 2020-10-22 02:25:49 +0300 (Thu, 22 Oct 2020) $
#$Revision: 258535 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038913.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_4038913
loop_
_publ_author_name
'Chaudhri, Nivedita'
'Zeller, Matthias'
'Brückner, Christian'
_publ_section_title
;
 Stepwise Reduction of Octaethyl-β,β′-dioxochlorin Isomers:
 Access to Structurally and Electronically Diverse Hydroporphyrins
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01989
_journal_year                    2020
_chemical_formula_sum            'C36 H48 N4 O2'
_chemical_formula_weight         568.78
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                94.5164(13)
_cell_angle_beta                 93.3913(13)
_cell_angle_gamma                106.5581(12)
_cell_formula_units_Z            2
_cell_length_a                   11.4151(5)
_cell_length_b                   11.6462(5)
_cell_length_c                   12.5464(6)
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.7660
_cell_measurement_theta_min      3.5467
_cell_volume                     1588.00(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            60098
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         81.645
_diffrn_reflns_theta_min         3.547
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       rod
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0097(11)
_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   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         6853
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0487
_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)+(0.0581P)²+0.5711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6509
_reflns_number_total             6853
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01989_si_003.cif
_cod_data_source_block           11-O7-(OH)3-rac
_cod_database_code               4038913
_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   0.889
_shelx_estimated_absorpt_t_max   0.924
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 1.25377(10) 0.56430(9) 0.70187(9) 0.0404(3) Uani 1 1 d . . . . .
N1 N 1.14146(9) 0.26588(9) 0.76262(8) 0.0240(2) Uani 1 1 d . . . . .
N2 N 0.94153(9) 0.13129(9) 0.59481(8) 0.0249(2) Uani 1 1 d . . . . .
H2 H 0.982205 0.112492 0.649280 0.030 Uiso 1 1 calc R U . . .
N3 N 0.92626(9) -0.08207(9) 0.71296(8) 0.0241(2) Uani 1 1 d . . . . .
N4 N 1.11269(9) 0.04834(9) 0.88112(8) 0.0235(2) Uani 1 1 d . . . . .
H4 H 1.077704 0.063766 0.821694 0.028 Uiso 1 1 calc R U . . .
C1 C 1.22743(11) 0.31313(11) 0.84787(10) 0.0236(3) Uani 1 1 d . . . . .
C2 C 1.29578(11) 0.44443(11) 0.84162(10) 0.0258(3) Uani 1 1 d . . . . .
C3 C 1.23264(12) 0.46788(11) 0.73938(11) 0.0280(3) Uani 1 1 d . . . . .
C4 C 1.14000(11) 0.35249(11) 0.69802(10) 0.0249(3) Uani 1 1 d . . . . .
C5 C 1.06180(11) 0.34272(12) 0.60488(10) 0.0270(3) Uani 1 1 d . . . . .
H5 H 1.073301 0.413049 0.568393 0.032 Uiso 1 1 calc R U . . .
C6 C 0.97087(11) 0.24311(11) 0.56086(10) 0.0258(3) Uani 1 1 d D . . . .
C7 C 0.88714(16) 0.23989(16) 0.46191(14) 0.0261(4) Uani 0.930(3) 1 d D U P A 1
H7 H 0.934084 0.239961 0.397084 0.031 Uiso 0.930(3) 1 calc R U P A 1
O2 O 0.84746(10) 0.34412(9) 0.47040(9) 0.0363(3) Uani 0.930(3) 1 d D U P A 1
H2O1 H 0.819401 0.354784 0.409753 0.054 Uiso 0.930(3) 1 calc R U P A 1
C7B C 0.8643(17) 0.2503(17) 0.4844(16) 0.030(5) Uani 0.070(3) 1 d D U P A 2
H7B H 0.816431 0.301501 0.517533 0.036 Uiso 0.070(3) 1 calc R U P A 2
O2B O 0.9192(17) 0.2971(17) 0.3918(14) 0.055(5) Uani 0.070(3) 1 d D U P A 2
H2O2 H 0.949717 0.372080 0.403934 0.082 Uiso 0.070(3) 1 calc R U P A 2
C8 C 0.78575(11) 0.11628(11) 0.45835(10) 0.0254(3) Uani 1 1 d D . . . .
C9 C 0.84294(11) 0.05040(11) 0.53666(10) 0.0251(3) Uani 1 1 d . . . . .
C10 C 0.79963(11) -0.06828(12) 0.55136(10) 0.0267(3) Uani 1 1 d . . . . .
H10 H 0.734294 -0.114790 0.501479 0.032 Uiso 1 1 calc R U . . .
C11 C 0.83932(11) -0.13184(11) 0.63160(10) 0.0250(3) Uani 1 1 d . . . . .
C12 C 0.78425(11) -0.26017(11) 0.63752(10) 0.0264(3) Uani 1 1 d . . . . .
C13 C 0.84013(11) -0.28780(11) 0.72675(10) 0.0262(3) Uani 1 1 d . . . . .
C14 C 0.92853(11) -0.17587(11) 0.77386(10) 0.0241(3) Uani 1 1 d . . . . .
C15 C 1.00026(11) -0.16536(11) 0.86911(10) 0.0250(3) Uani 1 1 d . . . . .
H15 H 0.990458 -0.237069 0.903274 0.030 Uiso 1 1 calc R U . . .
C16 C 1.08541(11) -0.06183(11) 0.92106(10) 0.0241(3) Uani 1 1 d . . . . .
C17 C 1.16085(11) -0.04820(11) 1.01851(10) 0.0247(3) Uani 1 1 d . . . . .
C18 C 1.23364(11) 0.07037(11) 1.03378(10) 0.0241(3) Uani 1 1 d . . . . .
C19 C 1.20187(11) 0.13010(11) 0.94709(10) 0.0234(2) Uani 1 1 d . . . . .
C20 C 1.25272(11) 0.25195(11) 0.93065(10) 0.0245(3) Uani 1 1 d . . . . .
H20 H 1.313167 0.298174 0.984780 0.029 Uiso 1 1 calc R U . . .
C21 C 1.43370(12) 0.46345(12) 0.83083(11) 0.0298(3) Uani 1 1 d . . . . .
H21A H 1.472178 0.548623 0.819213 0.036 Uiso 1 1 calc R U . . .
H21B H 1.471849 0.448413 0.899246 0.036 Uiso 1 1 calc R U . . .
C22 C 1.46174(14) 0.38344(15) 0.74020(14) 0.0420(4) Uani 1 1 d . . . . .
H22A H 1.434420 0.405297 0.671162 0.063 Uiso 1 1 calc R U . . .
H22B H 1.418591 0.299056 0.747518 0.063 Uiso 1 1 calc R U . . .
H22C H 1.550279 0.394361 0.743490 0.063 Uiso 1 1 calc R U . . .
C23 C 1.27729(12) 0.52719(12) 0.93689(11) 0.0306(3) Uani 1 1 d . . . . .
H23A H 1.316347 0.508286 1.003190 0.037 Uiso 1 1 calc R U . . .
H23B H 1.319795 0.611688 0.925884 0.037 Uiso 1 1 calc R U . . .
C24 C 1.14340(14) 0.51618(14) 0.95287(13) 0.0379(3) Uani 1 1 d . . . . .
H24A H 1.107219 0.546892 0.892588 0.057 Uiso 1 1 calc R U . . .
H24B H 1.138451 0.563140 1.019905 0.057 Uiso 1 1 calc R U . . .
H24C H 1.098419 0.431441 0.956404 0.057 Uiso 1 1 calc R U . . .
C25 C 0.76301(12) 0.04928(13) 0.34476(11) 0.0314(3) Uani 1 1 d . . . . .
H25A H 0.842348 0.042719 0.321299 0.038 Uiso 1 1 calc R U . . .
H25B H 0.709198 -0.033459 0.348224 0.038 Uiso 1 1 calc R U . . .
C26 C 0.70510(16) 0.10775(17) 0.26091(12) 0.0442(4) Uani 1 1 d . . . . .
H26A H 0.698322 0.062076 0.190660 0.066 Uiso 1 1 calc R U . . .
H26B H 0.756296 0.190587 0.257951 0.066 Uiso 1 1 calc R U . . .
H26C H 0.623223 0.108425 0.279866 0.066 Uiso 1 1 calc R U . . .
C27 C 0.66420(13) 0.12844(14) 0.49865(12) 0.0343(3) Uani 1 1 d . . . . .
H27A H 0.635864 0.184257 0.455139 0.041 Uiso 1 1 calc R U . . .
H27B H 0.601863 0.048782 0.485365 0.041 Uiso 1 1 calc R U . . .
C28 C 0.66926(16) 0.17333(18) 0.61680(13) 0.0474(4) Uani 1 1 d . . . . .
H28A H 0.728928 0.253253 0.631068 0.071 Uiso 1 1 calc R U . . .
H28B H 0.694016 0.117340 0.661301 0.071 Uiso 1 1 calc R U . . .
H28C H 0.588076 0.178241 0.633987 0.071 Uiso 1 1 calc R U . . .
C29 C 0.68195(12) -0.34119(12) 0.56212(12) 0.0325(3) Uani 1 1 d . . . . .
H29A H 0.680614 -0.425836 0.567909 0.039 Uiso 1 1 calc R U . . .
H29B H 0.698039 -0.323262 0.487627 0.039 Uiso 1 1 calc R U . . .
C30 C 0.55641(13) -0.32721(15) 0.58473(14) 0.0412(4) Uani 1 1 d . . . . .
H30A H 0.556441 -0.244023 0.577511 0.062 Uiso 1 1 calc R U . . .
H30B H 0.539008 -0.346641 0.657825 0.062 Uiso 1 1 calc R U . . .
H30C H 0.493265 -0.381993 0.533344 0.062 Uiso 1 1 calc R U . . .
C31 C 0.81831(13) -0.40779(12) 0.76951(12) 0.0333(3) Uani 1 1 d . . . . .
H31A H 0.731107 -0.454430 0.752432 0.040 Uiso 1 1 calc R U . . .
H31B H 0.834645 -0.395677 0.848589 0.040 Uiso 1 1 calc R U . . .
C32 C 0.89899(18) -0.47981(15) 0.72302(15) 0.0486(4) Uani 1 1 d . . . . .
H32A H 0.879842 -0.496085 0.645141 0.073 Uiso 1 1 calc R U . . .
H32B H 0.883613 -0.556148 0.755225 0.073 Uiso 1 1 calc R U . . .
H32C H 0.985452 -0.433561 0.738776 0.073 Uiso 1 1 calc R U . . .
C33 C 1.16109(12) -0.14486(12) 1.09102(11) 0.0294(3) Uani 1 1 d . . . . .
H33A H 1.088258 -0.214850 1.069759 0.035 Uiso 1 1 calc R U . . .
H33B H 1.154639 -0.114137 1.165634 0.035 Uiso 1 1 calc R U . . .
C34 C 1.27630(14) -0.18597(13) 1.08725(13) 0.0384(3) Uani 1 1 d . . . . .
H34A H 1.284212 -0.214804 1.013276 0.058 Uiso 1 1 calc R U . . .
H34B H 1.270398 -0.251274 1.133236 0.058 Uiso 1 1 calc R U . . .
H34C H 1.348349 -0.118260 1.112806 0.058 Uiso 1 1 calc R U . . .
C35 C 1.33018(12) 0.13021(12) 1.12332(10) 0.0279(3) Uani 1 1 d . . . . .
H35A H 1.320350 0.078628 1.183179 0.033 Uiso 1 1 calc R U . . .
H35B H 1.317652 0.207747 1.150066 0.033 Uiso 1 1 calc R U . . .
C36 C 1.46067(13) 0.15366(14) 1.08952(13) 0.0367(3) Uani 1 1 d . . . . .
H36A H 1.476906 0.076709 1.070552 0.055 Uiso 1 1 calc R U . . .
H36B H 1.519196 0.198957 1.149045 0.055 Uiso 1 1 calc R U . . .
H36C H 1.469606 0.200347 1.027289 0.055 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 0.0181 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
C4 N1 C1 109.26(10) . . ?
C6 N2 C9 113.97(10) . . ?
C6 N2 H2 123.0 . . ?
C9 N2 H2 123.0 . . ?
C11 N3 C14 104.98(10) . . ?
C19 N4 C16 109.90(10) . . ?
C19 N4 H4 125.1 . . ?
C16 N4 H4 125.1 . . ?
C20 C1 N1 125.61(11) . . ?
C20 C1 C2 121.71(11) . . ?
N1 C1 C2 112.68(10) . . ?
C3 C2 C1 100.56(10) . . ?
C3 C2 C23 109.99(11) . . ?
C1 C2 C23 112.67(10) . . ?
C3 C2 C21 111.03(11) . . ?
C1 C2 C21 111.94(10) . . ?
C23 C2 C21 110.31(10) . . ?
O1 C3 C4 128.03(12) . . ?
O1 C3 C2 125.44(12) . . ?
C4 C3 C2 106.51(10) . . ?
N1 C4 C5 127.27(11) . . ?
N1 C4 C3 110.96(11) . . ?
C5 C4 C3 121.75(11) . . ?
C6 C5 C4 127.21(12) . . ?
C6 C5 H5 116.4 . . ?
C4 C5 H5 116.4 . . ?
N2 C6 C5 127.22(12) . . ?
N2 C6 C7 108.29(11) . . ?
C5 C6 C7 124.47(12) . . ?
N2 C6 C7B 108.0(7) . . ?
C5 C6 C7B 122.8(7) . . ?
O2 C7 C6 108.38(13) . . ?
O2 C7 C8 116.69(14) . . ?
C6 C7 C8 104.26(12) . . ?
O2 C7 H7 109.1 . . ?
C6 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
C7 O2 H2O1 109.5 . . ?
O2B C7B C6 105.2(15) . . ?
O2B C7B C8 110.9(15) . . ?
C6 C7B C8 103.7(11) . . ?
O2B C7B H7B 112.2 . . ?
C6 C7B H7B 112.2 . . ?
C8 C7B H7B 112.2 . . ?
C7B O2B H2O2 109.5 . . ?
C9 C8 C25 110.98(11) . . ?
C9 C8 C27 109.07(10) . . ?
C25 C8 C27 110.45(10) . . ?
C9 C8 C7B 103.4(7) . . ?
C25 C8 C7B 123.5(8) . . ?
C27 C8 C7B 98.2(9) . . ?
C9 C8 C7 102.08(10) . . ?
C25 C8 C7 110.93(11) . . ?
C27 C8 C7 113.04(12) . . ?
C10 C9 N2 125.16(11) . . ?
C10 C9 C8 125.76(11) . . ?
N2 C9 C8 108.99(10) . . ?
C9 C10 C11 128.50(12) . . ?
C9 C10 H10 115.8 . . ?
C11 C10 H10 115.8 . . ?
N3 C11 C10 125.34(11) . . ?
N3 C11 C12 112.02(11) . . ?
C10 C11 C12 122.57(11) . . ?
C13 C12 C11 106.09(11) . . ?
C13 C12 C29 128.23(12) . . ?
C11 C12 C29 125.60(12) . . ?
C12 C13 C14 106.16(11) . . ?
C12 C13 C31 128.07(12) . . ?
C14 C13 C31 125.77(12) . . ?
C15 C14 N3 125.36(11) . . ?
C15 C14 C13 123.85(11) . . ?
N3 C14 C13 110.74(11) . . ?
C14 C15 C16 127.80(12) . . ?
C14 C15 H15 116.1 . . ?
C16 C15 H15 116.1 . . ?
N4 C16 C15 123.45(11) . . ?
N4 C16 C17 107.37(10) . . ?
C15 C16 C17 129.15(12) . . ?
C18 C17 C16 107.32(11) . . ?
C18 C17 C33 126.53(11) . . ?
C16 C17 C33 126.16(11) . . ?
C17 C18 C19 107.59(11) . . ?
C17 C18 C35 128.47(11) . . ?
C19 C18 C35 123.94(11) . . ?
N4 C19 C20 125.35(11) . . ?
N4 C19 C18 107.82(10) . . ?
C20 C19 C18 126.83(11) . . ?
C1 C20 C19 129.19(11) . . ?
C1 C20 H20 115.4 . . ?
C19 C20 H20 115.4 . . ?
C22 C21 C2 114.39(11) . . ?
C22 C21 H21A 108.7 . . ?
C2 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C2 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C2 114.13(11) . . ?
C24 C23 H23A 108.7 . . ?
C2 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C2 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C8 114.91(12) . . ?
C26 C25 H25A 108.5 . . ?
C8 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
C8 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
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 . . ?
C28 C27 C8 115.95(12) . . ?
C28 C27 H27A 108.3 . . ?
C8 C27 H27A 108.3 . . ?
C28 C27 H27B 108.3 . . ?
C8 C27 H27B 108.3 . . ?
H27A C27 H27B 107.4 . . ?
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 . . ?
C12 C29 C30 112.93(12) . . ?
C12 C29 H29A 109.0 . . ?
C30 C29 H29A 109.0 . . ?
C12 C29 H29B 109.0 . . ?
C30 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C13 C31 C32 112.47(12) . . ?
C13 C31 H31A 109.1 . . ?
C32 C31 H31A 109.1 . . ?
C13 C31 H31B 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
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 . . ?
C17 C33 C34 112.62(11) . . ?
C17 C33 H33A 109.1 . . ?
C34 C33 H33A 109.1 . . ?
C17 C33 H33B 109.1 . . ?
C34 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 C35 C36 113.14(11) . . ?
C18 C35 H35A 109.0 . . ?
C36 C35 H35A 109.0 . . ?
C18 C35 H35B 109.0 . . ?
C36 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
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 . . ?
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 C3 1.2178(16) . ?
N1 C4 1.3458(16) . ?
N1 C1 1.3731(15) . ?
N2 C6 1.3585(16) . ?
N2 C9 1.3699(15) . ?
N2 H2 0.8800 . ?
N3 C11 1.3498(16) . ?
N3 C14 1.3868(16) . ?
N4 C19 1.3608(15) . ?
N4 C16 1.3735(16) . ?
N4 H4 0.8800 . ?
C1 C20 1.3666(17) . ?
C1 C2 1.5164(16) . ?
C2 C3 1.5157(17) . ?
C2 C23 1.5383(18) . ?
C2 C21 1.5418(17) . ?
C3 C4 1.4862(17) . ?
C4 C5 1.4047(17) . ?
C5 C6 1.3686(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.513(2) . ?
C6 C7B 1.530(18) . ?
C7 O2 1.410(2) . ?
C7 C8 1.565(2) . ?
C7 H7 1.0000 . ?
O2 H2O1 0.8400 . ?
C7B O2B 1.425(17) . ?
C7B C8 1.561(17) . ?
C7B H7B 1.0000 . ?
O2B H2O2 0.8400 . ?
C8 C9 1.5194(17) . ?
C8 C25 1.5405(18) . ?
C8 C27 1.5442(18) . ?
C9 C10 1.3602(18) . ?
C10 C11 1.4216(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.4567(17) . ?
C12 C13 1.3613(18) . ?
C12 C29 1.4998(17) . ?
C13 C14 1.4578(16) . ?
C13 C31 1.4961(18) . ?
C14 C15 1.3848(17) . ?
C15 C16 1.3988(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.4242(17) . ?
C17 C18 1.3855(17) . ?
C17 C33 1.5026(17) . ?
C18 C19 1.4194(17) . ?
C18 C35 1.5016(17) . ?
C19 C20 1.4086(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.520(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.5235(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.515(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.525(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.528(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.523(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.524(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.5278(19) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
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
C4 N1 C1 C20 178.78(12) . . . . ?
C4 N1 C1 C2 -1.77(14) . . . . ?
C20 C1 C2 C3 -178.91(12) . . . . ?
N1 C1 C2 C3 1.61(14) . . . . ?
C20 C1 C2 C23 -61.87(16) . . . . ?
N1 C1 C2 C23 118.65(12) . . . . ?
C20 C1 C2 C21 63.15(16) . . . . ?
N1 C1 C2 C21 -116.33(12) . . . . ?
C1 C2 C3 O1 177.56(14) . . . . ?
C23 C2 C3 O1 58.55(18) . . . . ?
C21 C2 C3 O1 -63.83(18) . . . . ?
C1 C2 C3 C4 -0.88(13) . . . . ?
C23 C2 C3 C4 -119.88(11) . . . . ?
C21 C2 C3 C4 117.74(11) . . . . ?
C1 N1 C4 C5 -177.06(13) . . . . ?
C1 N1 C4 C3 1.11(14) . . . . ?
O1 C3 C4 N1 -178.44(14) . . . . ?
C2 C3 C4 N1 -0.06(15) . . . . ?
O1 C3 C4 C5 -0.2(2) . . . . ?
C2 C3 C4 C5 178.22(12) . . . . ?
N1 C4 C5 C6 0.1(2) . . . . ?
C3 C4 C5 C6 -177.85(13) . . . . ?
C9 N2 C6 C5 177.88(13) . . . . ?
C9 N2 C6 C7 -3.65(16) . . . . ?
C9 N2 C6 C7B 13.4(10) . . . . ?
C4 C5 C6 N2 -3.8(2) . . . . ?
C4 C5 C6 C7 178.01(14) . . . . ?
C4 C5 C6 C7B 158.6(11) . . . . ?
N2 C6 C7 O2 137.01(13) . . . . ?
C5 C6 C7 O2 -44.5(2) . . . . ?
N2 C6 C7 C8 12.08(16) . . . . ?
C5 C6 C7 C8 -169.40(13) . . . . ?
N2 C6 C7B O2B -130.3(13) . . . . ?
C5 C6 C7B O2B 64.4(18) . . . . ?
N2 C6 C7B C8 -13.8(14) . . . . ?
C5 C6 C7B C8 -179.1(5) . . . . ?
O2B C7B C8 C9 121.9(14) . . . . ?
C6 C7B C8 C9 9.4(13) . . . . ?
O2B C7B C8 C25 -4.9(19) . . . . ?
C6 C7B C8 C25 -117.4(9) . . . . ?
O2B C7B C8 C27 -126.2(15) . . . . ?
C6 C7B C8 C27 121.4(11) . . . . ?
O2 C7 C8 C9 -134.46(13) . . . . ?
C6 C7 C8 C9 -15.00(15) . . . . ?
O2 C7 C8 C25 107.25(15) . . . . ?
C6 C7 C8 C25 -133.29(12) . . . . ?
O2 C7 C8 C27 -17.45(18) . . . . ?
C6 C7 C8 C27 102.02(14) . . . . ?
C6 N2 C9 C10 176.53(12) . . . . ?
C6 N2 C9 C8 -6.89(15) . . . . ?
C25 C8 C9 C10 -51.53(17) . . . . ?
C27 C8 C9 C10 70.38(16) . . . . ?
C7B C8 C9 C10 174.1(9) . . . . ?
C7 C8 C9 C10 -169.78(13) . . . . ?
C25 C8 C9 N2 131.91(11) . . . . ?
C27 C8 C9 N2 -106.18(12) . . . . ?
C7B C8 C9 N2 -2.5(9) . . . . ?
C7 C8 C9 N2 13.66(14) . . . . ?
N2 C9 C10 C11 4.5(2) . . . . ?
C8 C9 C10 C11 -171.48(12) . . . . ?
C14 N3 C11 C10 176.33(12) . . . . ?
C14 N3 C11 C12 -0.73(14) . . . . ?
C9 C10 C11 N3 3.4(2) . . . . ?
C9 C10 C11 C12 -179.82(13) . . . . ?
N3 C11 C12 C13 0.50(15) . . . . ?
C10 C11 C12 C13 -176.65(12) . . . . ?
N3 C11 C12 C29 177.59(12) . . . . ?
C10 C11 C12 C29 0.4(2) . . . . ?
C11 C12 C13 C14 -0.05(14) . . . . ?
C29 C12 C13 C14 -177.03(13) . . . . ?
C11 C12 C13 C31 -179.53(13) . . . . ?
C29 C12 C13 C31 3.5(2) . . . . ?
C11 N3 C14 C15 -176.59(12) . . . . ?
C11 N3 C14 C13 0.69(13) . . . . ?
C12 C13 C14 C15 176.93(12) . . . . ?
C31 C13 C14 C15 -3.6(2) . . . . ?
C12 C13 C14 N3 -0.40(14) . . . . ?
C31 C13 C14 N3 179.10(12) . . . . ?
N3 C14 C15 C16 -1.8(2) . . . . ?
C13 C14 C15 C16 -178.77(12) . . . . ?
C19 N4 C16 C15 -177.66(12) . . . . ?
C19 N4 C16 C17 0.70(14) . . . . ?
C14 C15 C16 N4 -1.7(2) . . . . ?
C14 C15 C16 C17 -179.65(13) . . . . ?
N4 C16 C17 C18 -1.01(14) . . . . ?
C15 C16 C17 C18 177.23(13) . . . . ?
N4 C16 C17 C33 179.00(12) . . . . ?
C15 C16 C17 C33 -2.8(2) . . . . ?
C16 C17 C18 C19 0.93(14) . . . . ?
C33 C17 C18 C19 -179.08(12) . . . . ?
C16 C17 C18 C35 -178.86(12) . . . . ?
C33 C17 C18 C35 1.1(2) . . . . ?
C16 N4 C19 C20 179.68(12) . . . . ?
C16 N4 C19 C18 -0.13(14) . . . . ?
C17 C18 C19 N4 -0.51(14) . . . . ?
C35 C18 C19 N4 179.29(11) . . . . ?
C17 C18 C19 C20 179.68(12) . . . . ?
C35 C18 C19 C20 -0.5(2) . . . . ?
N1 C1 C20 C19 1.9(2) . . . . ?
C2 C1 C20 C19 -177.54(12) . . . . ?
N4 C19 C20 C1 -1.3(2) . . . . ?
C18 C19 C20 C1 178.49(13) . . . . ?
C3 C2 C21 C22 -59.14(15) . . . . ?
C1 C2 C21 C22 52.36(16) . . . . ?
C23 C2 C21 C22 178.67(12) . . . . ?
C3 C2 C23 C24 56.26(15) . . . . ?
C1 C2 C23 C24 -55.04(15) . . . . ?
C21 C2 C23 C24 179.07(11) . . . . ?
C9 C8 C25 C26 179.56(12) . . . . ?
C27 C8 C25 C26 58.46(16) . . . . ?
C7B C8 C25 C26 -56.9(10) . . . . ?
C7 C8 C25 C26 -67.69(16) . . . . ?
C9 C8 C27 C28 47.57(17) . . . . ?
C25 C8 C27 C28 169.80(13) . . . . ?
C7B C8 C27 C28 -59.8(7) . . . . ?
C7 C8 C27 C28 -65.24(17) . . . . ?
C13 C12 C29 C30 98.85(17) . . . . ?
C11 C12 C29 C30 -77.59(17) . . . . ?
C12 C13 C31 C32 88.98(17) . . . . ?
C14 C13 C31 C32 -90.42(17) . . . . ?
C18 C17 C33 C34 -71.32(17) . . . . ?
C16 C17 C33 C34 108.66(15) . . . . ?
C17 C18 C35 C36 105.65(15) . . . . ?
C19 C18 C35 C36 -74.11(16) . . . . ?
