#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/69/4026997.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_4026997
loop_
_publ_author_name
'Sravan K. Surampudi'
'G. Nagarjuna'
'Daiki Okamoto'
'Piyali D. Chaudhuri'
'D. Venkataraman'
_publ_contact_author_address
;
Department of Chemistry
University of Massachusetts Amherst
710 N. Pleasant Street
Amherst, MA 01003
;
_publ_contact_author_email       dv@chem.umass.edu
_publ_contact_author_fax         413-545-4490
_publ_contact_author_name        'Dhandapani Venkataraman'
_publ_contact_author_phone       413-545-2028
_publ_section_title
;
 Apical Functionalization of Chiral Heterohelicenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2074
_journal_page_last               2079
_journal_paper_doi               10.1021/jo202623u
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C62 H44 N2 O12'
_chemical_formula_sum            'C63.5 H47 N2 O12.5'
_chemical_formula_weight         1038.03
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-12-17T11:30:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 121.565(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.9190(9)
_cell_length_b                   24.1923(16)
_cell_length_c                   15.2145(7)
_cell_measurement_reflns_used    3127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.98
_cell_measurement_theta_min      4.076
_cell_measurement_wavelength     0.71073
_cell_volume                     6560.5(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.327026E-1
_diffrn_orient_matrix_UB_12      -0.167461E-1
_diffrn_orient_matrix_UB_13      -0.698319E-1
_diffrn_orient_matrix_UB_21      -0.9949E-2
_diffrn_orient_matrix_UB_22      -0.323459E-1
_diffrn_orient_matrix_UB_23      0.320676E-1
_diffrn_orient_matrix_UB_31      -0.444887E-1
_diffrn_orient_matrix_UB_32      0.195432E-1
_diffrn_orient_matrix_UB_33      -0.67623E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6077
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        20.04
_diffrn_reflns_theta_max         20.04
_diffrn_reflns_theta_min         4.09
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.051
_exptl_crystal_description       prism
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.304
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     699
_refine_ls_number_reflns         6077
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.307
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0967
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2725
_refine_ls_wR_factor_ref         0.2931
_reflns_number_gt                5078
_reflns_number_total             6077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202623u_si_003_5.cif
_cod_data_source_block           compoundM2
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C63.50 H47 N2 O12.50'
_cod_database_code               4026997
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.9404(5) 0.4417(4) 0.3605(6) 0.100(2) Uani 1 1 d .
C2 C 0.8995(5) 0.4123(5) 0.3910(6) 0.103(2) Uani 1 1 d .
H2 H 0.872 0.4314 0.4133 0.123 Uiso 1 1 calc R
C3 C 0.8977(4) 0.3560(4) 0.3897(5) 0.091(2) Uani 1 1 d .
C4 C 0.9369(3) 0.3265(4) 0.3535(5) 0.080(2) Uani 1 1 d .
C5 C 0.9805(4) 0.3556(4) 0.3221(5) 0.090(2) Uani 1 1 d .
C6 C 0.9814(5) 0.4117(5) 0.3262(6) 0.106(3) Uani 1 1 d .
H6 H 1.0099 0.4311 0.3057 0.127 Uiso 1 1 calc R
C7 C 0.8374(4) 0.2684(4) 0.3924(6) 0.091(2) Uani 1 1 d .
C8 C 0.7813(5) 0.2420(5) 0.3980(7) 0.107(3) Uani 1 1 d .
H8 H 0.7608 0.2581 0.4333 0.129 Uiso 1 1 calc R
C9 C 0.7557(5) 0.1913(5) 0.3505(9) 0.121(3) Uani 1 1 d .
H9 H 0.7175 0.1734 0.3537 0.145 Uiso 1 1 calc R
C10 C 0.7857(4) 0.1668(4) 0.2988(7) 0.098(2) Uani 1 1 d .
H10 H 0.7686 0.1325 0.2677 0.118 Uiso 1 1 calc R
C11 C 0.8413(4) 0.1939(3) 0.2938(6) 0.090(2) Uani 1 1 d .
C12 C 0.8727(4) 0.2428(3) 0.3455(5) 0.082(2) Uani 1 1 d .
C13 C 1.0342(4) 0.2663(3) 0.3125(6) 0.087(2) Uani 1 1 d .
C14 C 0.9920(4) 0.2396(3) 0.3478(5) 0.0798(19) Uani 1 1 d .
C15 C 1.0101(4) 0.1866(3) 0.3847(6) 0.0830(18) Uani 1 1 d .
H15 H 0.9831 0.1695 0.41 0.1 Uiso 1 1 calc R
C16 C 1.0670(4) 0.1582(4) 0.3853(6) 0.101(2) Uani 1 1 d .
H16 H 1.0791 0.1224 0.4114 0.121 Uiso 1 1 calc R
C17 C 1.1068(5) 0.1840(4) 0.3458(8) 0.115(3) Uani 1 1 d .
H17 H 1.1445 0.165 0.3435 0.138 Uiso 1 1 calc R
C18 C 1.0900(4) 0.2371(4) 0.3106(6) 0.103(2) Uani 1 1 d .
H18 H 1.1168 0.2539 0.2848 0.123 Uiso 1 1 calc R
C19 C 1.0236(4) 0.3259(4) 0.2873(6) 0.100(2) Uani 1 1 d .
C20 C 0.8545(4) 0.3263(4) 0.4256(7) 0.101(2) Uani 1 1 d .
C21 C 0.8525(5) 0.1945(4) 0.1480(7) 0.102(2) Uani 1 1 d .
C22 C 0.8659(6) 0.1623(5) 0.0784(7) 0.121(3) Uani 1 1 d .
C23 C 0.9098(11) 0.1913(9) 0.0350(13) 0.237(9) Uani 1 1 d .
H23A H 0.9634 0.1926 0.0845 0.284 Uiso 1 1 calc R
H23B H 0.8909 0.228 0.0086 0.284 Uiso 1 1 calc R
C24 C 0.8875(15) 0.1468(11) -0.0552(16) 0.287(14) Uani 1 1 d .
H24A H 0.8609 0.1648 -0.1219 0.344 Uiso 1 1 calc R
H24B H 0.9324 0.1298 -0.0468 0.344 Uiso 1 1 calc R
C25 C 0.8415(9) 0.1062(6) -0.0492(9) 0.161(4) Uani 1 1 d .
C26 C 0.8915(9) 0.0743(10) 0.0513(11) 0.203(7) Uani 1 1 d .
C27 C 0.7946(7) 0.1380(4) -0.0176(7) 0.133(3) Uani 1 1 d .
C28 C 0.8070(14) 0.0721(9) -0.1465(13) 0.243(8) Uani 1 1 d .
H28A H 0.7707 0.0472 -0.148 0.364 Uiso 1 1 calc R
H28B H 0.8455 0.0513 -0.148 0.364 Uiso 1 1 calc R
H28C H 0.7829 0.0961 -0.2054 0.364 Uiso 1 1 calc R
C29 C 0.7391(10) 0.1826(6) -0.0913(9) 0.195(6) Uani 1 1 d .
H29A H 0.714 0.1994 -0.0603 0.293 Uiso 1 1 calc R
H29B H 0.7027 0.1657 -0.1554 0.293 Uiso 1 1 calc R
H29C H 0.7662 0.2104 -0.1037 0.293 Uiso 1 1 calc R
C30 C 0.7509(7) 0.1034(5) 0.0130(10) 0.153(4) Uani 1 1 d .
H30A H 0.7225 0.1268 0.0311 0.23 Uiso 1 1 calc R
H30B H 0.7846 0.081 0.0713 0.23 Uiso 1 1 calc R
H30C H 0.7174 0.08 -0.0435 0.23 Uiso 1 1 calc R
C31 C 0.9382(5) 0.6096(4) 0.3622(6) 0.107(3) Uani 1 1 d .
C32 C 0.9925(5) 0.6416(4) 0.3578(6) 0.099(2) Uani 1 1 d .
H32 H 1.0308 0.6239 0.3548 0.118 Uiso 1 1 calc R
C33 C 0.9904(4) 0.6988(4) 0.3577(6) 0.091(2) Uani 1 1 d .
C34 C 0.9310(3) 0.7264(4) 0.3580(5) 0.083(2) Uani 1 1 d .
C35 C 0.8784(4) 0.6948(4) 0.3657(5) 0.092(2) Uani 1 1 d .
C36 C 0.8806(5) 0.6374(4) 0.3658(5) 0.097(2) Uani 1 1 d .
H36 H 0.8437 0.6172 0.3683 0.117 Uiso 1 1 calc R
C37 C 1.0287(4) 0.7894(4) 0.3205(6) 0.100(2) Uani 1 1 d .
C38 C 1.0682(5) 0.8175(5) 0.2884(10) 0.126(3) Uani 1 1 d .
H38 H 1.1129 0.8025 0.3001 0.151 Uiso 1 1 calc R
C39 C 1.0455(6) 0.8663(5) 0.2401(10) 0.136(3) Uani 1 1 d .
H39 H 1.0729 0.8842 0.2162 0.163 Uiso 1 1 calc R
C40 C 0.9795(5) 0.8896(4) 0.2264(8) 0.122(3) Uani 1 1 d .
H40 H 0.964 0.9242 0.1957 0.147 Uiso 1 1 calc R
C41 C 0.9378(4) 0.8622(4) 0.2576(6) 0.093(2) Uani 1 1 d .
C42 C 0.9634(4) 0.8132(4) 0.3109(6) 0.089(2) Uani 1 1 d .
C43 C 0.8286(4) 0.7811(4) 0.3928(5) 0.087(2) Uani 1 1 d .
C44 C 0.8851(4) 0.8099(3) 0.3894(5) 0.0803(19) Uani 1 1 d .
C45 C 0.9001(4) 0.8635(3) 0.4248(5) 0.090(2) Uani 1 1 d .
H45 H 0.9379 0.8833 0.4238 0.107 Uiso 1 1 calc R
C46 C 0.8582(5) 0.8887(4) 0.4627(6) 0.107(2) Uani 1 1 d .
H46 H 0.8695 0.9246 0.4885 0.129 Uiso 1 1 calc R
C47 C 0.8005(5) 0.8601(5) 0.4615(7) 0.117(3) Uani 1 1 d .
H47 H 0.7717 0.8773 0.4839 0.141 Uiso 1 1 calc R
C48 C 0.7861(5) 0.8082(4) 0.4284(7) 0.105(3) Uani 1 1 d .
H48 H 0.7475 0.7892 0.4286 0.127 Uiso 1 1 calc R
C49 C 0.8169(5) 0.7230(4) 0.3656(6) 0.100(2) Uani 1 1 d .
C049 C 0.9404(5) 0.5505(6) 0.3619(6) 0.116(3) Uani 1 1 d .
C50 C 1.0483(5) 0.7310(4) 0.3561(7) 0.103(2) Uani 1 1 d .
C051 C 0.9407(5) 0.4999(6) 0.3595(6) 0.119(3) Uani 1 1 d .
C51 C 0.8058(5) 0.8604(4) 0.1738(6) 0.105(2) Uani 1 1 d .
C52 C 0.7378(4) 0.8939(3) 0.1421(6) 0.097(2) Uani 1 1 d .
C53 C 0.6795(5) 0.8697(5) 0.1620(10) 0.149(4) Uani 1 1 d .
H53A H 0.6956 0.8722 0.2343 0.179 Uiso 1 1 calc R
H53B H 0.6688 0.8315 0.14 0.179 Uiso 1 1 calc R
C54 C 0.6108(6) 0.9073(5) 0.0947(11) 0.161(4) Uani 1 1 d .
H54A H 0.5967 0.9282 0.1365 0.193 Uiso 1 1 calc R
H54B H 0.568 0.8861 0.0435 0.193 Uiso 1 1 calc R
C55 C 0.6424(6) 0.9457(5) 0.0437(9) 0.144(4) Uani 1 1 d .
C56 C 0.6998(5) 0.9823(5) 0.1377(8) 0.119(3) Uani 1 1 d .
C57 C 0.6935(5) 0.9109(4) 0.0275(7) 0.116(3) Uani 1 1 d .
C58 C 0.5821(7) 0.9847(6) -0.0467(11) 0.187(5) Uani 1 1 d .
H58A H 0.552 1.0028 -0.0246 0.281 Uiso 1 1 calc R
H58B H 0.5504 0.9628 -0.1067 0.281 Uiso 1 1 calc R
H58C H 0.6076 1.012 -0.0632 0.281 Uiso 1 1 calc R
C59 C 0.6564(8) 0.8638(5) -0.0497(10) 0.192(6) Uani 1 1 d .
H59A H 0.6938 0.8439 -0.0553 0.289 Uiso 1 1 calc R
H59B H 0.6198 0.8786 -0.1159 0.289 Uiso 1 1 calc R
H59C H 0.6322 0.8392 -0.0265 0.289 Uiso 1 1 calc R
C60 C 0.7431(8) 0.9420(5) -0.0026(10) 0.158(4) Uani 1 1 d .
H60A H 0.7752 0.9162 -0.0092 0.237 Uiso 1 1 calc R
H60B H 0.7732 0.9686 0.0498 0.237 Uiso 1 1 calc R
H60C H 0.712 0.9606 -0.0671 0.237 Uiso 1 1 calc R
N1 N 0.9343(3) 0.2697(3) 0.3482(4) 0.0837(17) Uani 1 1 d .
N2 N 0.9261(3) 0.7836(3) 0.3531(4) 0.0797(16) Uani 1 1 d .
O1 O 1.0507(4) 0.3486(3) 0.2402(5) 0.129(2) Uani 1 1 d .
O2 O 0.8319(4) 0.3492(3) 0.4771(5) 0.132(2) Uani 1 1 d .
O3 O 0.8636(3) 0.1686(2) 0.2310(4) 0.0941(14) Uani 1 1 d .
O4 O 0.8292(5) 0.2411(4) 0.1279(5) 0.142(2) Uani 1 1 d .
O5 O 0.9168(9) 0.0283(7) 0.0671(10) 0.253(7) Uani 1 1 d .
O6 O 0.9084(4) 0.1135(4) 0.1291(5) 0.165(3) Uani 1 1 d .
O7 O 0.7589(4) 0.6978(3) 0.3481(6) 0.143(2) Uani 1 1 d .
O8 O 1.1087(4) 0.7100(3) 0.3769(6) 0.138(2) Uani 1 1 d .
O9 O 0.8703(3) 0.8874(2) 0.2318(4) 0.0933(14) Uani 1 1 d .
O10 O 0.8034(3) 0.8128(3) 0.1463(5) 0.127(2) Uani 1 1 d .
O11 O 0.7002(4) 1.0294(4) 0.1597(7) 0.152(2) Uani 1 1 d .
O12 O 0.7579(3) 0.9455(3) 0.1961(4) 0.1158(17) Uani 1 1 d .
C100 C 1 0.0597(9) 0.5 0.185(7) Uiso 1 2 d SD
H10A H 0.9583 0.049 0.4338 0.277 Uiso 0.5 1 calc PR
H10B H 1.0406 0.0718 0.4926 0.277 Uiso 0.5 1 calc PR
H10C H 0.9851 0.0893 0.5275 0.277 Uiso 0.5 1 calc PR
C101 C 1.0245(19) 0.0122(12) 0.571(2) 0.229(15) Uiso 0.5 1 d PD
C102 C 1.0866(12) 0.0298(12) 0.6755(15) 0.164(8) Uiso 0.5 1 d PD
H10D H 1.1029 -0.0013 0.7215 0.246 Uiso 0.5 1 calc PR
H10E H 1.0689 0.0584 0.7012 0.246 Uiso 0.5 1 calc PR
H10F H 1.1279 0.0435 0.671 0.246 Uiso 0.5 1 calc PR
O100 O 0.9884(16) -0.0232(11) 0.541(2) 0.233(9) Uiso 0.5 1 d P
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 0 '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 0.006 '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_3
C2 C1 C051 122.0(10) .
C2 C1 C6 117.9(8) .
C051 C1 C6 120.1(10) .
C3 C2 C1 122.2(8) .
C3 C2 H2 118.9 .
C1 C2 H2 118.9 .
C2 C3 C4 119.9(8) .
C2 C3 C20 120.2(8) .
C4 C3 C20 119.9(8) .
N1 C4 C3 121.3(7) .
N1 C4 C5 119.3(7) .
C3 C4 C5 119.4(8) .
C6 C5 C4 118.5(8) .
C6 C5 C19 121.0(8) .
C4 C5 C19 120.5(8) .
C5 C6 C1 122.2(8) .
C5 C6 H6 118.9 .
C1 C6 H6 118.9 .
C8 C7 C12 121.1(8) .
C8 C7 C20 118.9(8) .
C12 C7 C20 119.6(7) .
C7 C8 C9 119.3(8) .
C7 C8 H8 120.4 .
C9 C8 H8 120.4 .
C10 C9 C8 121.0(8) .
C10 C9 H9 119.5 .
C8 C9 H9 119.5 .
C9 C10 C11 118.8(9) .
C9 C10 H10 120.6 .
C11 C10 H10 120.6 .
C10 C11 C12 122.8(7) .
C10 C11 O3 115.1(8) .
C12 C11 O3 122.1(6) .
C11 C12 C7 116.4(6) .
C11 C12 N1 124.1(7) .
C7 C12 N1 119.4(8) .
C18 C13 C14 118.7(8) .
C18 C13 C19 120.5(7) .
C14 C13 C19 120.5(7) .
C15 C14 C13 119.4(6) .
C15 C14 N1 122.3(6) .
C13 C14 N1 118.2(7) .
C16 C15 C14 121.6(7) .
C16 C15 H15 119.2 .
C14 C15 H15 119.2 .
C15 C16 C17 118.8(8) .
C15 C16 H16 120.6 .
C17 C16 H16 120.6 .
C18 C17 C16 119.9(8) .
C18 C17 H17 120 .
C16 C17 H17 120 .
C17 C18 C13 121.5(8) .
C17 C18 H18 119.3 .
C13 C18 H18 119.3 .
O1 C19 C5 123.1(8) .
O1 C19 C13 121.8(8) .
C5 C19 C13 115.1(8) .
O2 C20 C3 122.1(9) .
O2 C20 C7 122.6(8) .
C3 C20 C7 115.2(8) .
O4 C21 O3 122.3(9) .
O4 C21 C22 121.6(9) .
O3 C21 C22 116.0(9) .
O6 C22 C21 110.5(8) .
O6 C22 C27 102.4(8) .
C21 C22 C27 115.4(9) .
O6 C22 C23 105.3(12) .
C21 C22 C23 116.8(10) .
C27 C22 C23 105.2(9) .
C22 C23 C24 95.1(12) .
C22 C23 H23A 112.7 .
C24 C23 H23A 112.7 .
C22 C23 H23B 112.7 .
C24 C23 H23B 112.7 .
H23A C23 H23B 110.2 .
C25 C24 C23 108.3(11) .
C25 C24 H24A 110.1 .
C23 C24 H24A 110.1 .
C25 C24 H24B 110 .
C23 C24 H24B 110 .
H24A C24 H24B 108.4 .
C24 C25 C28 108.0(13) .
C24 C25 C27 104.1(14) .
C28 C25 C27 122.3(14) .
C24 C25 C26 106.4(17) .
C28 C25 C26 115.4(14) .
C27 C25 C26 99.0(9) .
O5 C26 O6 124.4(14) .
O5 C26 C25 131.7(14) .
O6 C26 C25 103.8(15) .
C30 C27 C25 114.9(11) .
C30 C27 C29 105.6(11) .
C25 C27 C29 119.3(10) .
C30 C27 C22 111.4(8) .
C25 C27 C22 91.5(9) .
C29 C27 C22 113.8(10) .
C25 C28 H28A 109.5 .
C25 C28 H28B 109.5 .
H28A C28 H28B 109.5 .
C25 C28 H28C 109.4 .
H28A C28 H28C 109.5 .
H28B C28 H28C 109.5 .
C27 C29 H29A 109.5 .
C27 C29 H29B 109.5 .
H29A C29 H29B 109.5 .
C27 C29 H29C 109.5 .
H29A C29 H29C 109.5 .
H29B C29 H29C 109.5 .
C27 C30 H30A 109.5 .
C27 C30 H30B 109.5 .
H30A C30 H30B 109.5 .
C27 C30 H30C 109.5 .
H30A C30 H30C 109.5 .
H30B C30 H30C 109.5 .
C32 C31 C36 118.0(9) .
C32 C31 C049 121.4(9) .
C36 C31 C049 120.6(9) .
C33 C32 C31 121.6(8) .
C33 C32 H32 119.2 .
C31 C32 H32 119.2 .
C32 C33 C34 120.1(8) .
C32 C33 C50 120.6(8) .
C34 C33 C50 119.2(8) .
N2 C34 C35 120.8(7) .
N2 C34 C33 121.0(7) .
C35 C34 C33 118.3(8) .
C36 C35 C34 121.5(8) .
C36 C35 C49 119.7(8) .
C34 C35 C49 118.7(9) .
C35 C36 C31 120.4(8) .
C35 C36 H36 119.8 .
C31 C36 H36 119.8 .
C38 C37 C42 119.8(9) .
C38 C37 C50 120.5(8) .
C42 C37 C50 119.4(7) .
C39 C38 C37 122.5(9) .
C39 C38 H38 118.7 .
C37 C38 H38 118.7 .
C38 C39 C40 118.3(9) .
C38 C39 H39 120.8 .
C40 C39 H39 120.9 .
C41 C40 C39 120.8(9) .
C41 C40 H40 119.6 .
C39 C40 H40 119.6 .
C40 C41 C42 120.1(7) .
C40 C41 O9 115.4(8) .
C42 C41 O9 124.5(6) .
C41 C42 C37 117.9(7) .
C41 C42 N2 124.0(6) .
C37 C42 N2 118.0(8) .
C44 C43 C48 119.7(8) .
C44 C43 C49 119.6(7) .
C48 C43 C49 120.6(7) .
C45 C44 N2 121.6(6) .
C45 C44 C43 118.7(7) .
N2 C44 C43 119.7(7) .
C44 C45 C46 120.1(7) .
C44 C45 H45 120 .
C46 C45 H45 120 .
C47 C46 C45 120.2(8) .
C47 C46 H46 119.9 .
C45 C46 H46 119.9 .
C48 C47 C46 120.1(8) .
C48 C47 H47 120 .
C46 C47 H47 119.9 .
C47 C48 C43 121.1(8) .
C47 C48 H48 119.4 .
C43 C48 H48 119.4 .
O7 C49 C43 122.2(8) .
O7 C49 C35 121.9(9) .
C43 C49 C35 115.8(7) .
C051 C049 C31 178.4(11) .
O8 C50 C33 121.7(9) .
O8 C50 C37 122.0(8) .
C33 C50 C37 116.2(7) .
C049 C051 C1 177.3(11) .
O10 C51 O9 122.4(8) .
O10 C51 C52 123.1(8) .
O9 C51 C52 114.4(8) .
O12 C52 C51 110.3(6) .
O12 C52 C53 104.3(8) .
C51 C52 C53 117.3(7) .
O12 C52 C57 103.8(6) .
C51 C52 C57 114.9(8) .
C53 C52 C57 104.9(7) .
C52 C53 C54 101.9(8) .
C52 C53 H53A 111.4 .
C54 C53 H53A 111.4 .
C52 C53 H53B 111.4 .
C54 C53 H53B 111.4 .
H53A C53 H53B 109.3 .
C53 C54 C55 101.0(8) .
C53 C54 H54A 111.6 .
C55 C54 H54A 111.5 .
C53 C54 H54B 111.6 .
C55 C54 H54B 111.6 .
H54A C54 H54B 109.4 .
C57 C55 C54 105.8(10) .
C57 C55 C56 101.4(7) .
C54 C55 C56 101.7(9) .
C57 C55 C58 120.4(11) .
C54 C55 C58 115.5(9) .
C56 C55 C58 109.5(10) .
O11 C56 O12 124.1(9) .
O11 C56 C55 133.3(10) .
O12 C56 C55 102.5(9) .
C55 C57 C59 115.7(10) .
C55 C57 C60 115.5(9) .
C59 C57 C60 106.7(11) .
C55 C57 C52 91.3(7) .
C59 C57 C52 115.8(8) .
C60 C57 C52 111.6(8) .
C55 C58 H58A 109.5 .
C55 C58 H58B 109.5 .
H58A C58 H58B 109.5 .
C55 C58 H58C 109.4 .
H58A C58 H58C 109.5 .
H58B C58 H58C 109.5 .
C57 C59 H59A 109.4 .
C57 C59 H59B 109.5 .
H59A C59 H59B 109.5 .
C57 C59 H59C 109.5 .
H59A C59 H59C 109.5 .
H59B C59 H59C 109.5 .
C57 C60 H60A 109.5 .
C57 C60 H60B 109.5 .
H60A C60 H60B 109.5 .
C57 C60 H60C 109.5 .
H60A C60 H60C 109.5 .
H60B C60 H60C 109.5 .
C4 N1 C14 120.6(6) .
C4 N1 C12 117.7(6) .
C14 N1 C12 121.7(7) .
C34 N2 C44 118.7(6) .
C34 N2 C42 118.6(6) .
C44 N2 C42 122.7(7) .
C21 O3 C11 119.4(6) .
C26 O6 C22 106.9(10) .
C51 O9 C41 119.8(6) .
C56 O12 C52 107.3(7) .
C101 C100 H10A 109.5 .
C101 C100 H10B 109.5 .
H10A C100 H10B 109.5 .
C101 C100 H10C 109.5 .
H10A C100 H10C 109.5 .
H10B C100 H10C 109.5 .
O100 C101 C100 114(3) .
O100 C101 C102 135(3) .
C100 C101 C102 109.4(18) .
O100 C101 C101 70(2) 2_756
C100 C101 C101 51.4(13) 2_756
C102 C101 C101 153(3) 2_756
C101 C102 H10D 109.5 .
C101 C102 H10E 109.6 .
H10D C102 H10E 109.5 .
C101 C102 H10F 109.3 .
H10D C102 H10F 109.5 .
H10E C102 H10F 109.5 .
C101 O100 C101 75(3) 2_756
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.366(12) .
C1 C051 1.409(16) .
C1 C6 1.415(13) .
C2 C3 1.363(12) .
C2 H2 0.93 .
C3 C4 1.401(11) .
C3 C20 1.465(11) .
C4 N1 1.374(10) .
C4 C5 1.418(10) .
C5 C6 1.358(12) .
C5 C19 1.454(12) .
C6 H6 0.93 .
C7 C8 1.379(12) .
C7 C12 1.409(10) .
C7 C20 1.470(12) .
C8 C9 1.381(13) .
C8 H8 0.93 .
C9 C10 1.370(13) .
C9 H9 0.93 .
C10 C11 1.372(11) .
C10 H10 0.93 .
C11 C12 1.383(10) .
C11 O3 1.405(9) .
C12 N1 1.426(9) .
C13 C18 1.377(11) .
C13 C14 1.408(10) .
C13 C19 1.478(12) .
C14 C15 1.373(10) .
C14 N1 1.411(9) .
C15 C16 1.372(10) .
C15 H15 0.93 .
C16 C17 1.402(12) .
C16 H16 0.93 .
C17 C18 1.365(12) .
C17 H17 0.93 .
C18 H18 0.93 .
C19 O1 1.248(10) .
C20 O2 1.238(10) .
C21 O4 1.203(10) .
C21 O3 1.316(10) .
C21 C22 1.456(13) .
C22 O6 1.435(13) .
C22 C27 1.557(15) .
C22 C23 1.550(16) .
C23 C24 1.61(2) .
C23 H23A 0.97 .
C23 H23B 0.97 .
C24 C25 1.41(2) .
C24 H24A 0.97 .
C24 H24B 0.97 .
C25 C28 1.51(2) .
C25 C27 1.511(16) .
C25 C26 1.53(2) .
C26 O5 1.20(2) .
C26 O6 1.410(18) .
C27 C30 1.483(16) .
C27 C29 1.551(16) .
C28 H28A 0.96 .
C28 H28B 0.96 .
C28 H28C 0.96 .
C29 H29A 0.96 .
C29 H29B 0.96 .
C29 H29C 0.96 .
C30 H30A 0.96 .
C30 H30B 0.96 .
C30 H30C 0.96 .
C31 C32 1.407(12) .
C31 C36 1.406(12) .
C31 C049 1.430(16) .
C32 C33 1.384(11) .
C32 H32 0.93 .
C33 C34 1.413(11) .
C33 C50 1.451(12) .
C34 N2 1.385(10) .
C34 C35 1.394(11) .
C35 C36 1.390(11) .
C35 C49 1.457(12) .
C36 H36 0.93 .
C37 C38 1.345(13) .
C37 C42 1.418(11) .
C37 C50 1.491(12) .
C38 C39 1.338(14) .
C38 H38 0.93 .
C39 C40 1.404(14) .
C39 H39 0.93 .
C40 C41 1.362(11) .
C40 H40 0.93 .
C41 C42 1.377(11) .
C41 O9 1.393(9) .
C42 N2 1.437(10) .
C43 C44 1.394(10) .
C43 C48 1.422(11) .
C43 C49 1.450(12) .
C44 C45 1.377(10) .
C44 N2 1.393(9) .
C45 C46 1.416(11) .
C45 H45 0.93 .
C46 C47 1.384(12) .
C46 H46 0.93 .
C47 C48 1.328(12) .
C47 H47 0.93 .
C48 H48 0.93 .
C49 O7 1.256(9) .
C049 C051 1.223(14) .
C50 O8 1.240(10) .
C51 O10 1.217(10) .
C51 O9 1.335(10) .
C51 C52 1.481(12) .
C52 O12 1.430(10) .
C52 C53 1.519(12) .
C52 C57 1.541(12) .
C53 C54 1.549(14) .
C53 H53A 0.97 .
C53 H53B 0.97 .
C54 C55 1.561(16) .
C54 H54A 0.97 .
C54 H54B 0.97 .
C55 C57 1.481(14) .
C55 C56 1.572(17) .
C55 C58 1.599(15) .
C56 O11 1.187(12) .
C56 O12 1.389(12) .
C57 C59 1.525(15) .
C57 C60 1.534(15) .
C58 H58A 0.96 .
C58 H58B 0.96 .
C58 H58C 0.96 .
C59 H59A 0.96 .
C59 H59B 0.96 .
C59 H59C 0.96 .
C60 H60A 0.96 .
C60 H60B 0.96 .
C60 H60C 0.96 .
C100 C101 1.471(19) .
C100 H10A 0.96 .
C100 H10B 0.96 .
C100 H10C 0.96 .
C101 O100 1.07(3) .
C101 C102 1.50(2) .
C101 C101 1.83(6) 2_756
C102 H10D 0.96 .
C102 H10E 0.96 .
C102 H10F 0.96 .
O100 C101 1.79(4) 2_756
