#------------------------------------------------------------------------------
#$Date: 2024-04-04 02:51:14 +0200 (Thu 04 de Apr de 2024) $
#$Revision: 290771 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/13/1571357.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_1571357
loop_
_publ_author_name
'Li, Xing-Chi'
'Cheng, Ying'
'Wang, Xu-Dong'
'Tong, Shuo'
'Wang, Mei-Xiang'
_publ_section_title
;
 De novo synthesis of inherently chiral heteracalix[4]aromatics
 from enantioselective macrocyclization enabled by chiral phosphoric
 acid-catalyzed intramolecular SNAr reaction.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              3610
_journal_page_last               3615
_journal_paper_doi               10.1039/d3sc06436k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C45 H43 N9 O4'
_chemical_formula_weight         773.88
_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
;
2023-10-26 deposited with the CCDC.	2024-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                105.174(2)
_cell_angle_beta                 98.881(2)
_cell_angle_gamma                107.685(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0108(2)
_cell_length_b                   12.9368(3)
_cell_length_c                   17.2186(4)
_cell_measurement_reflns_used    6323
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.489
_cell_measurement_theta_min      2.749
_cell_volume                     1983.04(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33123
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        62.489
_diffrn_reflns_theta_max         62.489
_diffrn_reflns_theta_min         2.749
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77729
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0046(3)
_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   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0365
_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)+(0.0445P)²+1.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6153
_reflns_number_total             6323
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc06436k2.cif
_cod_data_source_block           a
_cod_original_cell_volume        1983.04(8)
_cod_database_code               1571357
_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, -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
C1 C 0.53041(14) 0.81768(11) 0.36774(8) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.52264(14) 0.83668(11) 0.29161(8) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.62650(14) 0.82417(11) 0.24845(8) 0.0181(3) Uani 1 1 d . . . . .
H3A H 0.617995 0.836041 0.196025 0.022 Uiso 1 1 calc R U . . .
C4 C 0.74204(14) 0.79511(12) 0.27862(8) 0.0185(3) Uani 1 1 d . . . . .
C5 C 0.74596(15) 0.77257(12) 0.35377(9) 0.0192(3) Uani 1 1 d . . . . .
H5A H 0.822038 0.750869 0.376079 0.023 Uiso 1 1 calc R U . . .
C6 C 0.64115(15) 0.78120(12) 0.39646(8) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.75688(16) 0.84891(14) 0.54686(9) 0.0285(4) Uani 1 1 d . . . . .
H7A H 0.833692 0.897157 0.528850 0.043 Uiso 1 1 calc R U . . .
H7B H 0.709599 0.896228 0.577457 0.043 Uiso 1 1 calc R U . . .
H7C H 0.799029 0.813642 0.583104 0.043 Uiso 1 1 calc R U . . .
C8 C 0.53323(15) 0.68185(12) 0.48497(9) 0.0192(3) Uani 1 1 d . . . . .
C9 C 0.40968(15) 0.61322(12) 0.56901(8) 0.0202(3) Uani 1 1 d . . . . .
C10 C 0.32552(15) 0.53162(12) 0.43275(8) 0.0192(3) Uani 1 1 d . . . . .
C11 C 0.18456(15) 0.47962(12) 0.23692(9) 0.0198(3) Uani 1 1 d . . . . .
H11A H 0.154399 0.541761 0.258663 0.024 Uiso 1 1 calc R U . . .
C12 C 0.22784(15) 0.42270(12) 0.28761(8) 0.0202(3) Uani 1 1 d . . . . .
C13 C 0.26856(16) 0.33013(13) 0.25770(9) 0.0261(3) Uani 1 1 d . . . . .
H13A H 0.297042 0.291447 0.293370 0.031 Uiso 1 1 calc R U . . .
C14 C 0.26674(17) 0.29525(14) 0.17435(10) 0.0288(3) Uani 1 1 d . . . . .
H14A H 0.293637 0.231292 0.152463 0.035 Uiso 1 1 calc R U . . .
C15 C 0.22638(16) 0.35192(13) 0.12213(9) 0.0236(3) Uani 1 1 d . . . . .
H15A H 0.226568 0.327312 0.065109 0.028 Uiso 1 1 calc R U . . .
C16 C 0.18575(14) 0.44463(12) 0.15347(8) 0.0185(3) Uani 1 1 d . . . . .
C17 C 0.17373(14) 0.61131(12) 0.11282(8) 0.0167(3) Uani 1 1 d . . . . .
C18 C 0.13378(14) 0.75435(12) 0.07481(8) 0.0169(3) Uani 1 1 d . . . . .
C19 C 0.30540(14) 0.79576(12) 0.18919(8) 0.0159(3) Uani 1 1 d . . . . .
C20 C 0.44023(16) 0.99647(12) 0.27917(9) 0.0241(3) Uani 1 1 d . . . . .
H20A H 0.521621 1.037732 0.328769 0.036 Uiso 1 1 calc R U . . .
H20B H 0.463956 1.023668 0.233187 0.036 Uiso 1 1 calc R U . . .
H20C H 0.353482 1.010495 0.291090 0.036 Uiso 1 1 calc R U . . .
C21 C 0.86246(15) 0.79611(13) 0.23300(9) 0.0217(3) Uani 1 1 d . . . . .
C22 C 0.80154(18) 0.75930(15) 0.13850(10) 0.0305(4) Uani 1 1 d . . . . .
H22A H 0.751900 0.809834 0.125843 0.046 Uiso 1 1 calc R U . . .
H22B H 0.881134 0.764702 0.111175 0.046 Uiso 1 1 calc R U . . .
H22C H 0.732697 0.679865 0.118184 0.046 Uiso 1 1 calc R U . . .
C23 C 0.97401(18) 0.91913(14) 0.26403(12) 0.0361(4) Uani 1 1 d . . . . .
H23A H 0.926148 0.971606 0.253311 0.054 Uiso 1 1 calc R U . . .
H23B H 1.016251 0.941708 0.323923 0.054 Uiso 1 1 calc R U . . .
H23C H 1.050843 0.922613 0.234656 0.054 Uiso 1 1 calc R U . . .
C24 C 0.93900(16) 0.71530(14) 0.25021(10) 0.0268(3) Uani 1 1 d . . . . .
H24A H 0.868695 0.636429 0.230623 0.040 Uiso 1 1 calc R U . . .
H24B H 1.015928 0.719338 0.220878 0.040 Uiso 1 1 calc R U . . .
H24C H 0.981336 0.738433 0.310146 0.040 Uiso 1 1 calc R U . . .
C25 C 0.28974(15) 0.79844(13) 0.38642(9) 0.0213(3) Uani 1 1 d . . . . .
H25A H 0.256526 0.722553 0.342599 0.026 Uiso 1 1 calc R U . . .
H25B H 0.264460 0.852872 0.361338 0.026 Uiso 1 1 calc R U . . .
C26 C 0.21750(14) 0.78901(12) 0.45588(8) 0.0187(3) Uani 1 1 d . . . . .
C27 C 0.25138(16) 0.88525(13) 0.52533(9) 0.0273(3) Uani 1 1 d . . . . .
H27A H 0.321942 0.956025 0.529167 0.033 Uiso 1 1 calc R U . . .
C28 C 0.18310(18) 0.87879(15) 0.58897(10) 0.0346(4) Uani 1 1 d . . . . .
H28A H 0.207111 0.944944 0.636233 0.041 Uiso 1 1 calc R U . . .
C29 C 0.07977(17) 0.77588(15) 0.58375(10) 0.0313(4) Uani 1 1 d . . . . .
H29A H 0.033554 0.771493 0.627631 0.038 Uiso 1 1 calc R U . . .
C30 C 0.04397(16) 0.67987(14) 0.51495(10) 0.0278(3) Uani 1 1 d . . . . .
H30A H -0.027611 0.609543 0.511018 0.033 Uiso 1 1 calc R U . . .
C31 C 0.11317(16) 0.68657(13) 0.45141(9) 0.0231(3) Uani 1 1 d . . . . .
H31A H 0.088863 0.620216 0.404259 0.028 Uiso 1 1 calc R U . . .
C32 C 0.27798(18) 0.53982(14) 0.65800(9) 0.0305(4) Uani 1 1 d . . . . .
H32A H 0.272990 0.461081 0.629597 0.037 Uiso 1 1 calc R U . . .
H32B H 0.186987 0.548218 0.633962 0.037 Uiso 1 1 calc R U . . .
C33 C 0.29774(17) 0.56115(13) 0.74976(9) 0.0287(4) Uani 1 1 d . . . . .
C34 C 0.21283(19) 0.61048(14) 0.79181(10) 0.0328(4) Uani 1 1 d . . . . .
H34A H 0.145543 0.634342 0.762758 0.039 Uiso 1 1 calc R U . . .
C35 C 0.2252(2) 0.62529(15) 0.87579(10) 0.0361(4) Uani 1 1 d . . . . .
H35A H 0.165999 0.658384 0.903887 0.043 Uiso 1 1 calc R U . . .
C36 C 0.3239(2) 0.59167(15) 0.91818(10) 0.0393(4) Uani 1 1 d . . . . .
H36A H 0.332006 0.600945 0.975505 0.047 Uiso 1 1 calc R U . . .
C37 C 0.41147(19) 0.54435(16) 0.87741(11) 0.0377(4) Uani 1 1 d . . . . .
H37A H 0.480920 0.523025 0.907172 0.045 Uiso 1 1 calc R U . . .
C38 C 0.39762(18) 0.52811(15) 0.79299(10) 0.0327(4) Uani 1 1 d . . . . .
H38A H 0.456388 0.494467 0.764907 0.039 Uiso 1 1 calc R U . . .
C39 C 0.07632(16) 0.90093(13) 0.03013(9) 0.0242(3) Uani 1 1 d . . . . .
H39A H 0.103793 0.944093 0.090412 0.029 Uiso 1 1 calc R U . . .
H39B H -0.015558 0.907064 0.004893 0.029 Uiso 1 1 calc R U . . .
C40 C 0.19245(16) 0.95322(13) -0.00850(10) 0.0257(3) Uani 1 1 d . . . . .
C41 C 0.31769(18) 1.04447(14) 0.04042(12) 0.0358(4) Uani 1 1 d . . . . .
H41A H 0.330883 1.072534 0.098932 0.043 Uiso 1 1 calc R U . . .
C42 C 0.4236(2) 1.09496(17) 0.00464(16) 0.0498(5) Uani 1 1 d . . . . .
H42A H 0.507501 1.159002 0.038245 0.060 Uiso 1 1 calc R U . . .
C43 C 0.4069(2) 1.0521(2) -0.07947(16) 0.0549(6) Uani 1 1 d . . . . .
H43A H 0.480149 1.085572 -0.103984 0.066 Uiso 1 1 calc R U . . .
C44 C 0.2840(2) 0.9606(2) -0.12852(13) 0.0481(5) Uani 1 1 d . . . . .
H44A H 0.273423 0.930869 -0.186672 0.058 Uiso 1 1 calc R U . . .
C45 C 0.17576(19) 0.91151(15) -0.09367(11) 0.0341(4) Uani 1 1 d . . . . .
H45A H 0.090374 0.849509 -0.127979 0.041 Uiso 1 1 calc R U . . .
N1 N 0.64985(12) 0.75890(10) 0.47397(7) 0.0200(3) Uani 1 1 d . . . . .
N2 N 0.43438(12) 0.60131(10) 0.41551(7) 0.0199(3) Uani 1 1 d . . . . .
N3 N 0.52722(12) 0.69108(10) 0.56332(7) 0.0212(3) Uani 1 1 d . . . . .
N4 N 0.30382(13) 0.53053(10) 0.50712(7) 0.0215(3) Uani 1 1 d . . . . .
N5 N 0.13686(13) 0.49753(10) 0.09798(7) 0.0197(3) Uani 1 1 d . . . . .
H5B H 0.077163 0.451797 0.049606 0.024 Uiso 1 1 calc R U . . .
N6 N 0.28026(12) 0.68471(10) 0.17935(7) 0.0174(3) Uani 1 1 d . . . . .
N7 N 0.09755(12) 0.64187(10) 0.05645(7) 0.0181(3) Uani 1 1 d . . . . .
N8 N 0.23285(12) 0.83742(10) 0.13938(7) 0.0174(3) Uani 1 1 d . . . . .
N9 N 0.41280(12) 0.87337(10) 0.25600(7) 0.0171(2) Uani 1 1 d . . . . .
O1 O 0.21455(11) 0.44937(8) 0.37008(6) 0.0233(2) Uani 1 1 d . . . . .
O2 O 0.44477(10) 0.83889(8) 0.42033(6) 0.0199(2) Uani 1 1 d . . . . .
O3 O 0.40181(11) 0.62395(9) 0.64729(6) 0.0245(2) Uani 1 1 d . . . . .
O4 O 0.05434(10) 0.78119(8) 0.01832(6) 0.0211(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C2 125.54(12) . . ?
O2 C1 C6 116.56(12) . . ?
C2 C1 C6 117.75(12) . . ?
C1 C2 C3 119.93(13) . . ?
C1 C2 N9 122.37(12) . . ?
C3 C2 N9 117.66(12) . . ?
C4 C3 C2 122.93(13) . . ?
C4 C3 H3A 118.5 . . ?
C2 C3 H3A 118.5 . . ?
C3 C4 C5 116.54(12) . . ?
C3 C4 C21 120.38(12) . . ?
C5 C4 C21 122.96(12) . . ?
C6 C5 C4 121.36(13) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C1 121.29(13) . . ?
C5 C6 N1 119.76(12) . . ?
C1 C6 N1 118.85(12) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 N2 125.75(13) . . ?
N3 C8 N1 116.89(12) . . ?
N2 C8 N1 117.36(12) . . ?
N4 C9 N3 127.64(13) . . ?
N4 C9 O3 118.91(12) . . ?
N3 C9 O3 113.45(12) . . ?
N2 C10 N4 128.54(13) . . ?
N2 C10 O1 119.92(12) . . ?
N4 C10 O1 111.52(12) . . ?
C12 C11 C16 119.04(13) . . ?
C12 C11 H11A 120.5 . . ?
C16 C11 H11A 120.5 . . ?
C13 C12 C11 122.07(13) . . ?
C13 C12 O1 117.54(12) . . ?
C11 C12 O1 119.95(13) . . ?
C12 C13 C14 118.14(14) . . ?
C12 C13 H13A 120.9 . . ?
C14 C13 H13A 120.9 . . ?
C13 C14 C15 121.19(14) . . ?
C13 C14 H14A 119.4 . . ?
C15 C14 H14A 119.4 . . ?
C16 C15 C14 119.70(14) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C11 119.83(13) . . ?
C15 C16 N5 118.85(12) . . ?
C11 C16 N5 121.18(12) . . ?
N6 C17 N5 119.57(12) . . ?
N6 C17 N7 125.04(12) . . ?
N5 C17 N7 115.39(12) . . ?
N7 C18 N8 128.57(12) . . ?
N7 C18 O4 111.70(12) . . ?
N8 C18 O4 119.72(12) . . ?
N6 C19 N8 126.16(12) . . ?
N6 C19 N9 116.50(12) . . ?
N8 C19 N9 117.34(12) . . ?
N9 C20 H20A 109.5 . . ?
N9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24 C21 C23 108.78(13) . . ?
C24 C21 C22 107.89(12) . . ?
C23 C21 C22 109.24(13) . . ?
C24 C21 C4 111.94(12) . . ?
C23 C21 C4 107.82(12) . . ?
C22 C21 C4 111.13(12) . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C25 C26 108.30(11) . . ?
O2 C25 H25A 110.0 . . ?
C26 C25 H25A 110.0 . . ?
O2 C25 H25B 110.0 . . ?
C26 C25 H25B 110.0 . . ?
H25A C25 H25B 108.4 . . ?
C31 C26 C27 118.67(13) . . ?
C31 C26 C25 121.50(13) . . ?
C27 C26 C25 119.80(13) . . ?
C28 C27 C26 120.56(14) . . ?
C28 C27 H27A 119.7 . . ?
C26 C27 H27A 119.7 . . ?
C27 C28 C29 120.08(15) . . ?
C27 C28 H28A 120.0 . . ?
C29 C28 H28A 120.0 . . ?
C30 C29 C28 120.10(14) . . ?
C30 C29 H29A 119.9 . . ?
C28 C29 H29A 119.9 . . ?
C29 C30 C31 119.65(14) . . ?
C29 C30 H30A 120.2 . . ?
C31 C30 H30A 120.2 . . ?
C30 C31 C26 120.94(14) . . ?
C30 C31 H31A 119.5 . . ?
C26 C31 H31A 119.5 . . ?
O3 C32 C33 107.30(12) . . ?
O3 C32 H32A 110.3 . . ?
C33 C32 H32A 110.3 . . ?
O3 C32 H32B 110.3 . . ?
C33 C32 H32B 110.3 . . ?
H32A C32 H32B 108.5 . . ?
C34 C33 C38 119.29(15) . . ?
C34 C33 C32 120.34(15) . . ?
C38 C33 C32 120.33(15) . . ?
C35 C34 C33 120.79(17) . . ?
C35 C34 H34A 119.6 . . ?
C33 C34 H34A 119.6 . . ?
C36 C35 C34 119.61(16) . . ?
C36 C35 H35A 120.2 . . ?
C34 C35 H35A 120.2 . . ?
C35 C36 C37 120.26(15) . . ?
C35 C36 H36A 119.9 . . ?
C37 C36 H36A 119.9 . . ?
C36 C37 C38 120.07(17) . . ?
C36 C37 H37A 120.0 . . ?
C38 C37 H37A 120.0 . . ?
C33 C38 C37 119.97(16) . . ?
C33 C38 H38A 120.0 . . ?
C37 C38 H38A 120.0 . . ?
O4 C39 C40 111.47(11) . . ?
O4 C39 H39A 109.3 . . ?
C40 C39 H39A 109.3 . . ?
O4 C39 H39B 109.3 . . ?
C40 C39 H39B 109.3 . . ?
H39A C39 H39B 108.0 . . ?
C45 C40 C41 119.16(15) . . ?
C45 C40 C39 120.40(15) . . ?
C41 C40 C39 120.44(15) . . ?
C42 C41 C40 120.60(19) . . ?
C42 C41 H41A 119.7 . . ?
C40 C41 H41A 119.7 . . ?
C43 C42 C41 119.73(19) . . ?
C43 C42 H42A 120.1 . . ?
C41 C42 H42A 120.1 . . ?
C42 C43 C44 120.20(18) . . ?
C42 C43 H43A 119.9 . . ?
C44 C43 H43A 119.9 . . ?
C43 C44 C45 120.5(2) . . ?
C43 C44 H44A 119.8 . . ?
C45 C44 H44A 119.8 . . ?
C44 C45 C40 119.80(18) . . ?
C44 C45 H45A 120.1 . . ?
C40 C45 H45A 120.1 . . ?
C8 N1 C6 119.60(11) . . ?
C8 N1 C7 119.20(11) . . ?
C6 N1 C7 116.83(11) . . ?
C10 N2 C8 112.66(12) . . ?
C9 N3 C8 113.36(12) . . ?
C9 N4 C10 112.04(12) . . ?
C17 N5 C16 125.83(11) . . ?
C17 N5 H5B 117.1 . . ?
C16 N5 H5B 117.1 . . ?
C17 N6 C19 114.51(11) . . ?
C18 N7 C17 113.46(11) . . ?
C18 N8 C19 112.17(11) . . ?
C19 N9 C2 117.92(11) . . ?
C19 N9 C20 121.90(11) . . ?
C2 N9 C20 118.41(11) . . ?
C10 O1 C12 120.29(11) . . ?
C1 O2 C25 118.84(10) . . ?
C9 O3 C32 116.26(11) . . ?
C18 O4 C39 119.18(11) . . ?
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
C1 O2 1.3721(16) . ?
C1 C2 1.3905(19) . ?
C1 C6 1.403(2) . ?
C2 C3 1.392(2) . ?
C2 N9 1.4393(17) . ?
C3 C4 1.389(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.396(2) . ?
C4 C21 1.5358(19) . ?
C5 C6 1.386(2) . ?
C5 H5A 0.9500 . ?
C6 N1 1.4326(18) . ?
C7 N1 1.4632(18) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N3 1.3353(18) . ?
C8 N2 1.3605(18) . ?
C8 N1 1.3612(18) . ?
C9 N4 1.3299(19) . ?
C9 N3 1.3326(19) . ?
C9 O3 1.3357(17) . ?
C10 N2 1.3159(18) . ?
C10 N4 1.3345(18) . ?
C10 O1 1.3569(17) . ?
C11 C12 1.380(2) . ?
C11 C16 1.392(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.380(2) . ?
C12 O1 1.4081(17) . ?
C13 C14 1.383(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15A 0.9500 . ?
C16 N5 1.4221(18) . ?
C17 N6 1.3376(18) . ?
C17 N5 1.3461(18) . ?
C17 N7 1.3548(18) . ?
C18 N7 1.3236(18) . ?
C18 N8 1.3271(18) . ?
C18 O4 1.3435(16) . ?
C19 N6 1.3400(18) . ?
C19 N8 1.3568(18) . ?
C19 N9 1.3583(18) . ?
C20 N9 1.4624(18) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C24 1.532(2) . ?
C21 C23 1.535(2) . ?
C21 C22 1.535(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 O2 1.4458(16) . ?
C25 C26 1.5027(19) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C31 1.391(2) . ?
C26 C27 1.391(2) . ?
C27 C28 1.385(2) . ?
C27 H27A 0.9500 . ?
C28 C29 1.387(2) . ?
C28 H28A 0.9500 . ?
C29 C30 1.379(2) . ?
C29 H29A 0.9500 . ?
C30 C31 1.390(2) . ?
C30 H30A 0.9500 . ?
C31 H31A 0.9500 . ?
C32 O3 1.4530(18) . ?
C32 C33 1.501(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.390(2) . ?
C33 C38 1.390(2) . ?
C34 C35 1.389(2) . ?
C34 H34A 0.9500 . ?
C35 C36 1.380(3) . ?
C35 H35A 0.9500 . ?
C36 C37 1.388(3) . ?
C36 H36A 0.9500 . ?
C37 C38 1.392(2) . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9500 . ?
C39 O4 1.4503(17) . ?
C39 C40 1.499(2) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C45 1.387(2) . ?
C40 C41 1.389(2) . ?
C41 C42 1.387(3) . ?
C41 H41A 0.9500 . ?
C42 C43 1.371(3) . ?
C42 H42A 0.9500 . ?
C43 C44 1.378(3) . ?
C43 H43A 0.9500 . ?
C44 C45 1.385(3) . ?
C44 H44A 0.9500 . ?
C45 H45A 0.9500 . ?
N5 H5B 0.8800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 172.60(12) . . . . ?
C6 C1 C2 C3 -2.76(19) . . . . ?
O2 C1 C2 N9 -5.1(2) . . . . ?
C6 C1 C2 N9 179.52(12) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
N9 C2 C3 C4 176.56(12) . . . . ?
C2 C3 C4 C5 3.3(2) . . . . ?
C2 C3 C4 C21 -172.96(12) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C21 C4 C5 C6 174.88(13) . . . . ?
C4 C5 C6 C1 -2.8(2) . . . . ?
C4 C5 C6 N1 -179.16(12) . . . . ?
O2 C1 C6 C5 -171.03(12) . . . . ?
C2 C1 C6 C5 4.8(2) . . . . ?
O2 C1 C6 N1 5.40(18) . . . . ?
C2 C1 C6 N1 -178.82(12) . . . . ?
C16 C11 C12 C13 -1.8(2) . . . . ?
C16 C11 C12 O1 -174.00(12) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
O1 C12 C13 C14 173.08(13) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C15 C16 C11 -0.5(2) . . . . ?
C14 C15 C16 N5 -176.47(13) . . . . ?
C12 C11 C16 C15 1.7(2) . . . . ?
C12 C11 C16 N5 177.53(12) . . . . ?
C3 C4 C21 C24 -154.97(13) . . . . ?
C5 C4 C21 C24 29.05(19) . . . . ?
C3 C4 C21 C23 85.43(16) . . . . ?
C5 C4 C21 C23 -90.56(16) . . . . ?
C3 C4 C21 C22 -34.26(18) . . . . ?
C5 C4 C21 C22 149.75(14) . . . . ?
O2 C25 C26 C31 -124.12(14) . . . . ?
O2 C25 C26 C27 58.01(17) . . . . ?
C31 C26 C27 C28 0.4(2) . . . . ?
C25 C26 C27 C28 178.35(14) . . . . ?
C26 C27 C28 C29 -0.1(3) . . . . ?
C27 C28 C29 C30 -0.4(3) . . . . ?
C28 C29 C30 C31 0.7(2) . . . . ?
C29 C30 C31 C26 -0.4(2) . . . . ?
C27 C26 C31 C30 -0.1(2) . . . . ?
C25 C26 C31 C30 -178.02(13) . . . . ?
O3 C32 C33 C34 107.01(16) . . . . ?
O3 C32 C33 C38 -75.24(18) . . . . ?
C38 C33 C34 C35 -1.0(2) . . . . ?
C32 C33 C34 C35 176.75(15) . . . . ?
C33 C34 C35 C36 0.6(2) . . . . ?
C34 C35 C36 C37 0.6(3) . . . . ?
C35 C36 C37 C38 -1.5(3) . . . . ?
C34 C33 C38 C37 0.1(2) . . . . ?
C32 C33 C38 C37 -177.63(15) . . . . ?
C36 C37 C38 C33 1.1(2) . . . . ?
O4 C39 C40 C45 62.31(17) . . . . ?
O4 C39 C40 C41 -118.08(15) . . . . ?
C45 C40 C41 C42 1.3(2) . . . . ?
C39 C40 C41 C42 -178.33(14) . . . . ?
C40 C41 C42 C43 -2.1(3) . . . . ?
C41 C42 C43 C44 1.2(3) . . . . ?
C42 C43 C44 C45 0.5(3) . . . . ?
C43 C44 C45 C40 -1.4(3) . . . . ?
C41 C40 C45 C44 0.5(2) . . . . ?
C39 C40 C45 C44 -179.93(15) . . . . ?
N3 C8 N1 C6 -158.40(12) . . . . ?
N2 C8 N1 C6 22.59(19) . . . . ?
N3 C8 N1 C7 -2.61(19) . . . . ?
N2 C8 N1 C7 178.38(13) . . . . ?
C5 C6 N1 C8 -127.26(14) . . . . ?
C1 C6 N1 C8 56.26(18) . . . . ?
C5 C6 N1 C7 76.38(17) . . . . ?
C1 C6 N1 C7 -100.10(15) . . . . ?
N4 C10 N2 C8 -1.0(2) . . . . ?
O1 C10 N2 C8 177.26(12) . . . . ?
N3 C8 N2 C10 1.5(2) . . . . ?
N1 C8 N2 C10 -179.54(12) . . . . ?
N4 C9 N3 C8 0.7(2) . . . . ?
O3 C9 N3 C8 -178.55(12) . . . . ?
N2 C8 N3 C9 -1.5(2) . . . . ?
N1 C8 N3 C9 179.63(12) . . . . ?
N3 C9 N4 C10 -0.2(2) . . . . ?
O3 C9 N4 C10 179.02(12) . . . . ?
N2 C10 N4 C9 0.4(2) . . . . ?
O1 C10 N4 C9 -177.98(12) . . . . ?
N6 C17 N5 C16 10.1(2) . . . . ?
N7 C17 N5 C16 -170.53(12) . . . . ?
C15 C16 N5 C17 -137.13(14) . . . . ?
C11 C16 N5 C17 47.0(2) . . . . ?
N5 C17 N6 C19 -178.42(12) . . . . ?
N7 C17 N6 C19 2.28(19) . . . . ?
N8 C19 N6 C17 0.77(19) . . . . ?
N9 C19 N6 C17 -179.99(11) . . . . ?
N8 C18 N7 C17 0.4(2) . . . . ?
O4 C18 N7 C17 -178.95(10) . . . . ?
N6 C17 N7 C18 -2.81(18) . . . . ?
N5 C17 N7 C18 177.86(11) . . . . ?
N7 C18 N8 C19 2.15(19) . . . . ?
O4 C18 N8 C19 -178.57(11) . . . . ?
N6 C19 N8 C18 -2.76(18) . . . . ?
N9 C19 N8 C18 178.00(11) . . . . ?
N6 C19 N9 C2 22.43(17) . . . . ?
N8 C19 N9 C2 -158.25(11) . . . . ?
N6 C19 N9 C20 -172.95(12) . . . . ?
N8 C19 N9 C20 6.37(18) . . . . ?
C1 C2 N9 C19 -107.59(15) . . . . ?
C3 C2 N9 C19 74.64(16) . . . . ?
C1 C2 N9 C20 87.24(16) . . . . ?
C3 C2 N9 C20 -90.53(15) . . . . ?
N2 C10 O1 C12 12.73(19) . . . . ?
N4 C10 O1 C12 -168.76(12) . . . . ?
C13 C12 O1 C10 96.66(15) . . . . ?
C11 C12 O1 C10 -90.79(16) . . . . ?
C2 C1 O2 C25 47.84(18) . . . . ?
C6 C1 O2 C25 -136.75(13) . . . . ?
C26 C25 O2 C1 157.85(12) . . . . ?
N4 C9 O3 C32 2.13(19) . . . . ?
N3 C9 O3 C32 -178.50(13) . . . . ?
C33 C32 O3 C9 174.97(13) . . . . ?
N7 C18 O4 C39 178.00(11) . . . . ?
N8 C18 O4 C39 -1.39(17) . . . . ?
C40 C39 O4 C18 88.75(15) . . . . ?
