#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/92/4109295.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_4109295
loop_
_publ_author_name
'Masahiro Inoue'
'Masahisa Nakada'
_publ_section_title
;
 Structure Elucidation and Enantioselective Total Synthesis of the Potent
 HMG-CoA Reductase Inhibitor FR901512 via Catalytic Asymmetric
 Nozaki-Hiyama Reactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4164
_journal_page_last               4165
_journal_paper_doi               10.1021/ja070812w
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C27 H23 Br N2 O8 '
_chemical_formula_sum            'C27 H23 Br N2 O8'
_chemical_formula_weight         583.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.9850(15)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   5.4978(3)
_cell_length_b                   17.7771(7)
_cell_length_c                   13.4393(6)
_cell_measurement_reflns_used    9148
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1284.86(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12686
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_exptl_absorpt_coefficient_mu    1.658
_exptl_absorpt_correction_T_max  0.780
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       platelet
_exptl_crystal_F_000             596.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.61
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2784 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.001(5)
_refine_ls_extinction_coef       -76(4)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   0.674
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     552
_refine_ls_number_reflns         3329
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.0046
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[1.0000σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0559
_reflns_number_gt                3300
_reflns_number_total             5803
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja070812wsi20070205_013842.cif
_cod_data_source_block           '_inouesan'
_cod_original_formula_sum        'C27 H23 Br N2 O8 '
_cod_database_code               4109295
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+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_symmetry_multiplicity
_atom_site_calc_flag
Br(1) Br 0.57002(6) 0.85040(4) 0.85702(3) 0.04804(10) Uani 1.00 1 d
O(2) O 0.7548(4) 1.14347(12) 0.5754(2) 0.0385(7) Uani 1.00 1 d
O(3) O -0.0277(3) 0.80111(11) 0.36565(16) 0.0295(6) Uani 1.00 1 d
O(4) O -0.1213(4) 0.97150(12) 0.31353(17) 0.0309(6) Uani 1.00 1 d
O(5) O -0.3541(4) 0.93425(12) 0.42538(19) 0.0370(7) Uani 1.00 1 d
O(6) O -0.2946(4) 0.73524(12) 0.43830(18) 0.0326(7) Uani 1.00 1 d
O(7) O 0.3153(5) 1.05842(14) 0.8307(2) 0.0584(9) Uani 1.00 1 d
O(8) O 0.5835(4) 1.13027(13) 0.4154(2) 0.0426(8) Uani 1.00 1 d
O(28) O -0.0137(5) 0.98952(17) 0.7857(2) 0.0697(10) Uani 1.00 1 d
N(16) N 0.5901(5) 1.12032(14) 0.5056(2) 0.0327(9) Uani 1.00 1 d
N(19) N 0.1608(6) 1.02475(16) 0.7666(2) 0.0429(9) Uani 1.00 1 d
C(9) C 0.3887(6) 1.07553(17) 0.5353(2) 0.0270(10) Uani 1.00 1 d
C(10) C -0.3091(6) 0.9460(2) 0.2236(2) 0.0305(10) Uani 1.00 1 d
C(11) C 0.4336(6) 0.8458(2) 0.6420(3) 0.0309(9) Uani 1.00 1 d
C(12) C -0.1743(6) 0.96458(16) 0.4058(2) 0.0265(9) Uani 1.00 1 d
C(13) C 0.1419(9) 0.7876(2) 0.7260(3) 0.0369(12) Uani 1.00 1 d
C(14) C 0.2174(8) 1.0420(2) 0.4589(2) 0.0258(10) Uani 1.00 1 d
C(15) C 0.3612(5) 0.82606(14) 0.7304(2) 0.0303(9) Uani 1.00 1 d
C(17) C 0.0645(5) 0.79004(16) 0.5444(2) 0.0249(8) Uani 1.00 1 d
C(18) C 0.2868(6) 0.82889(17) 0.5488(2) 0.0273(10) Uani 1.00 1 d
C(20) C 0.0271(5) 0.99961(16) 0.4854(2) 0.0251(8) Uani 1.00 1 d
C(21) C -0.1050(5) 0.77165(16) 0.4462(2) 0.0254(9) Uani 1.00 1 d
C(22) C -0.1917(8) 0.7863(2) 0.2679(2) 0.0311(11) Uani 1.00 1 d
C(23) C 0.0108(7) 0.9932(2) 0.5858(3) 0.0287(11) Uani 1.00 1 d
C(24) C -0.0801(5) 0.93687(17) 0.0807(2) 0.0305(9) Uani 1.00 1 d
C(25) C -0.4276(8) 1.0166(2) 0.1730(4) 0.0433(14) Uani 1.00 1 d
C(26) C 0.3790(6) 1.07011(18) 0.6364(2) 0.0295(10) Uani 1.00 1 d
C(27) C -0.2493(8) 1.0633(2) 0.1254(3) 0.0438(13) Uani 1.00 1 d
C(29) C -0.0911(5) 0.82655(16) 0.1870(2) 0.0279(9) Uani 1.00 1 d
C(30) C 0.1867(6) 1.02853(17) 0.6598(2) 0.0298(9) Uani 1.00 1 d
C(31) C -0.0061(8) 0.7692(2) 0.6333(4) 0.0323(12) Uani 1.00 1 d
C(32) C 0.0722(6) 0.78847(18) 0.1379(2) 0.0321(10) Uani 1.00 1 d
C(33) C -0.1615(5) 0.90161(17) 0.1604(2) 0.0283(9) Uani 1.00 1 d
C(34) C -0.1626(10) 1.0158(2) 0.0463(3) 0.0426(14) Uani 1.00 1 d
C(35) C 0.0794(11) 0.8972(2) 0.0323(3) 0.0396(14) Uani 1.00 1 d
C(36) C 0.1573(7) 0.82571(19) 0.0599(2) 0.0369(11) Uani 1.00 1 d
C(37) C -0.3690(14) 1.1365(2) 0.0816(4) 0.066(2) Uani 1.00 1 d
C(38) C 0.1599(11) 0.7095(3) 0.1684(5) 0.0488(17) Uani 1.00 1 d
H(1) H -0.437(5) 0.9148(16) 0.249(2) 0.029(11) Uani 1.00 1 c
H(2) H 0.572(4) 0.8700(16) 0.646(2) 0.021(10) Uani 1.00 1 c
H(3) H 0.101(5) 0.7787(18) 0.786(3) 0.045(12) Uani 1.00 1 c
H(4) H 0.233(6) 1.0478(16) 0.395(2) 0.030(11) Uani 1.00 1 c
H(5) H 0.347(4) 0.846(2) 0.493(2) 0.035(9) Uani 1.00 1 c
H(6) H -0.359(6) 0.8020(14) 0.273(2) 0.017(9) Uani 1.00 1 c
H(7) H -0.200(5) 0.7324(15) 0.256(2) 0.014(10) Uani 1.00 1 c
H(8) H -0.120(7) 0.9701(16) 0.603(2) 0.033(13) Uani 1.00 1 c
H(9) H -0.518(6) 1.0478(16) 0.226(2) 0.047(12) Uani 1.00 1 c
H(10) H -0.552(8) 1.006(2) 0.121(3) 0.075(19) Uani 1.00 1 c
H(11) H 0.502(7) 1.096(2) 0.688(2) 0.072(16) Uani 1.00 1 c
H(12) H -0.112(6) 1.0770(15) 0.181(2) 0.030(12) Uani 1.00 1 c
H(13) H -0.140(7) 0.745(2) 0.631(2) 0.046(15) Uani 1.00 1 c
H(14) H -0.314(6) 1.0114(18) -0.020(2) 0.046(13) Uani 1.00 1 c
H(15) H -0.043(7) 1.0377(15) 0.019(2) 0.040(13) Uani 1.00 1 c
H(16) H 0.124(6) 0.9164(19) -0.016(2) 0.037(13) Uani 1.00 1 c
H(17) H 0.279(5) 0.8001(16) 0.020(2) 0.036(12) Uani 1.00 1 c
H(18) H -0.425(8) 1.1694(19) 0.148(4) 0.092(19) Uani 1.00 1 c
H(19) H -0.255(10) 1.168(2) 0.063(4) 0.11(2) Uani 1.00 1 c
H(20) H -0.508(9) 1.123(2) 0.030(2) 0.068(16) Uani 1.00 1 c
H(21) H 0.020(7) 0.6653(18) 0.142(3) 0.082(16) Uani 1.00 1 c
H(22) H 0.273(10) 0.697(2) 0.134(3) 0.07(2) Uani 1.00 1 c
H(23) H 0.215(7) 0.7060(17) 0.240(2) 0.043(12) Uani 1.00 1 c
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Br Br -0.290 2.459
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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
C(21) O(3) C(22) 114.5(2)
C(10) O(4) C(12) 118.5(2)
O(2) N(16) O(8) 125.1(3)
O(2) N(16) C(9) 116.5(3)
O(8) N(16) C(9) 118.4(2)
O(7) N(19) O(28) 124.1(3)
O(7) N(19) C(30) 117.9(3)
O(28) N(19) C(30) 118.0(2)
N(16) C(9) C(14) 117.7(3)
N(16) C(9) C(26) 119.2(2)
C(14) C(9) C(26) 123.1(3)
O(4) C(10) C(25) 106.0(2)
O(4) C(10) C(33) 104.6(2)
C(25) C(10) C(33) 114.4(3)
C(15) C(11) C(18) 120.7(3)
O(4) C(12) O(5) 126.3(2)
O(4) C(12) C(20) 110.6(2)
O(5) C(12) C(20) 123.1(3)
C(15) C(13) C(31) 120.2(4)
C(9) C(14) C(20) 118.5(3)
Br(1) C(15) C(11) 119.2(2)
Br(1) C(15) C(13) 120.9(2)
C(11) C(15) C(13) 119.9(3)
C(18) C(17) C(21) 122.0(3)
C(18) C(17) C(31) 119.8(3)
C(21) C(17) C(31) 118.2(3)
C(11) C(18) C(17) 119.4(3)
C(12) C(20) C(14) 121.5(3)
C(12) C(20) C(23) 118.4(3)
C(14) C(20) C(23) 120.0(3)
O(3) C(21) O(6) 123.0(2)
O(3) C(21) C(17) 112.6(2)
O(6) C(21) C(17) 124.4(3)
O(3) C(22) C(29) 108.4(3)
C(20) C(23) C(30) 119.2(3)
C(33) C(24) C(34) 121.8(3)
C(33) C(24) C(35) 117.8(3)
C(34) C(24) C(35) 120.4(3)
C(10) C(25) C(27) 112.8(3)
C(9) C(26) C(30) 116.8(3)
C(25) C(27) C(34) 108.4(3)
C(25) C(27) C(37) 111.4(4)
C(34) C(27) C(37) 112.3(4)
C(22) C(29) C(32) 118.8(2)
C(22) C(29) C(33) 120.8(3)
C(32) C(29) C(33) 120.4(3)
N(19) C(30) C(23) 119.0(3)
N(19) C(30) C(26) 118.7(2)
C(23) C(30) C(26) 122.3(3)
C(13) C(31) C(17) 119.9(4)
C(29) C(32) C(36) 118.2(2)
C(29) C(32) C(38) 121.4(3)
C(36) C(32) C(38) 120.3(4)
C(10) C(33) C(24) 119.5(2)
C(10) C(33) C(29) 120.0(3)
C(24) C(33) C(29) 120.3(3)
C(24) C(34) C(27) 114.8(3)
C(24) C(35) C(36) 122.6(4)
C(32) C(36) C(35) 120.5(4)
O(4) C(10) H(1) 108.0(16)
C(25) C(10) H(1) 110.0(16)
C(33) C(10) H(1) 113.3(18)
C(15) C(11) H(2) 118.9(19)
C(18) C(11) H(2) 120.4(19)
C(15) C(13) H(3) 116(2)
C(31) C(13) H(3) 124(2)
C(9) C(14) H(4) 119(2)
C(20) C(14) H(4) 123(2)
C(11) C(18) H(5) 114.9(16)
C(17) C(18) H(5) 125.7(16)
O(3) C(22) H(6) 107.2(16)
O(3) C(22) H(7) 109.1(15)
C(29) C(22) H(6) 114.4(16)
C(29) C(22) H(7) 111.3(18)
H(6) C(22) H(7) 106(2)
C(20) C(23) H(8) 121(2)
C(30) C(23) H(8) 120(2)
C(10) C(25) H(9) 110.0(16)
C(10) C(25) H(10) 112(2)
C(27) C(25) H(9) 114.3(17)
C(27) C(25) H(10) 104(3)
H(9) C(25) H(10) 104(3)
C(9) C(26) H(11) 120(2)
C(30) C(26) H(11) 123(2)
C(25) C(27) H(12) 106(2)
C(34) C(27) H(12) 112(2)
C(37) C(27) H(12) 106.7(16)
C(13) C(31) H(13) 120(2)
C(17) C(31) H(13) 120(2)
C(24) C(34) H(14) 108.2(18)
C(24) C(34) H(15) 109.0(19)
C(27) C(34) H(14) 108.5(19)
C(27) C(34) H(15) 114(2)
H(14) C(34) H(15) 102(2)
C(24) C(35) H(16) 119(2)
C(36) C(35) H(16) 118(2)
C(32) C(36) H(17) 121.9(17)
C(35) C(36) H(17) 117.6(17)
C(27) C(37) H(18) 107(2)
C(27) C(37) H(19) 111(2)
C(27) C(37) H(20) 106(2)
H(18) C(37) H(19) 102(4)
H(18) C(37) H(20) 113(3)
H(19) C(37) H(20) 117(4)
C(32) C(38) H(21) 114.4(18)
C(32) C(38) H(22) 109(2)
C(32) C(38) H(23) 110.5(19)
H(21) C(38) H(22) 100(3)
H(21) C(38) H(23) 109(3)
H(22) C(38) H(23) 114(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br(1) C(15) 1.895(2)
O(2) N(16) 1.232(3)
O(3) C(21) 1.349(4)
O(3) C(22) 1.455(4)
O(4) C(10) 1.488(3)
O(4) C(12) 1.337(4)
O(5) C(12) 1.202(4)
O(6) C(21) 1.213(3)
O(7) N(19) 1.232(3)
O(8) N(16) 1.218(4)
O(28) N(19) 1.217(4)
N(16) C(9) 1.484(4)
N(19) C(30) 1.473(4)
C(9) C(14) 1.376(5)
C(9) C(26) 1.375(5)
C(10) C(25) 1.508(6)
C(10) C(33) 1.514(5)
C(11) C(15) 1.374(5)
C(11) C(18) 1.375(5)
C(12) C(20) 1.505(4)
C(13) C(15) 1.377(6)
C(13) C(31) 1.379(6)
C(14) C(20) 1.395(5)
C(17) C(18) 1.395(4)
C(17) C(21) 1.485(4)
C(17) C(31) 1.381(6)
C(20) C(23) 1.376(5)
C(22) C(29) 1.500(5)
C(23) C(30) 1.385(4)
C(24) C(33) 1.392(4)
C(24) C(34) 1.517(5)
C(24) C(35) 1.388(6)
C(25) C(27) 1.523(7)
C(26) C(30) 1.379(5)
C(27) C(34) 1.511(7)
C(27) C(37) 1.521(7)
C(29) C(32) 1.396(4)
C(29) C(33) 1.415(4)
C(32) C(36) 1.400(5)
C(32) C(38) 1.513(6)
C(35) C(36) 1.367(6)
C(10) H(1) 1.01(3)
C(11) H(2) 0.86(2)
C(13) H(3) 0.89(4)
C(14) H(4) 0.88(4)
C(18) H(5) 0.93(3)
C(22) H(6) 0.98(3)
C(22) H(7) 0.97(2)
C(23) H(8) 0.90(4)
C(25) H(9) 1.09(3)
C(25) H(10) 0.89(4)
C(26) H(11) 0.98(3)
C(27) H(12) 0.98(3)
C(31) H(13) 0.85(4)
C(34) H(14) 1.09(2)
C(34) H(15) 0.90(4)
C(35) H(16) 0.82(3)
C(36) H(17) 1.05(3)
C(37) H(18) 1.17(5)
C(37) H(19) 0.92(5)
C(37) H(20) 0.95(4)
C(38) H(21) 1.10(3)
C(38) H(22) 0.88(5)
C(38) H(23) 0.95(3)
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
Br(1) C(24) 3.564(2) 65601
Br(1) C(35) 3.368(5) 65601
O(2) O(3) 3.200(3) 65602
O(2) O(6) 2.984(3) 55602
O(2) O(6) 3.425(3) 65602
O(2) C(17) 3.322(4) 65602
O(2) C(20) 3.316(4) 65501
O(2) C(21) 3.036(3) 65602
O(2) C(23) 3.009(4) 65501
O(2) C(30) 3.159(3) 65501
O(2) C(38) 3.575(7) 65602
O(3) O(2) 3.200(3) 64602
O(5) O(8) 3.501(3) 45501
O(5) N(16) 3.512(3) 45501
O(5) C(9) 3.370(4) 45501
O(5) C(14) 3.141(5) 45501
O(5) C(18) 3.394(4) 45501
O(6) O(2) 2.984(3) 54602
O(6) O(2) 3.425(3) 64602
O(6) O(8) 3.342(3) 54602
O(6) N(16) 2.809(3) 54602
O(6) C(9) 2.921(3) 54602
O(6) C(18) 3.420(4) 45501
O(6) C(26) 3.106(3) 54602
O(8) O(5) 3.501(3) 65501
O(8) O(6) 3.342(3) 55602
O(8) C(12) 3.246(3) 65501
O(8) C(17) 3.416(3) 65602
O(8) C(20) 3.358(3) 65501
O(8) C(31) 3.543(5) 65602
N(16) O(5) 3.512(3) 65501
N(16) O(6) 2.809(3) 55602
N(16) C(12) 3.445(4) 65501
N(16) C(20) 3.274(4) 65501
N(16) C(23) 3.253(4) 65501
C(9) O(5) 3.370(4) 65501
C(9) O(6) 2.921(3) 55602
C(11) C(31) 3.393(6) 65501
C(12) O(8) 3.246(3) 45501
C(12) N(16) 3.445(4) 45501
C(14) O(5) 3.141(5) 65501
C(17) O(2) 3.322(4) 64602
C(17) O(8) 3.416(3) 64602
C(18) O(5) 3.394(4) 65501
C(18) O(6) 3.420(4) 65501
C(20) O(2) 3.316(4) 45501
C(20) O(8) 3.358(3) 45501
C(20) N(16) 3.274(4) 45501
C(21) O(2) 3.036(3) 64602
C(23) O(2) 3.009(4) 45501
C(23) N(16) 3.253(4) 45501
C(24) Br(1) 3.564(2) 45401
C(26) O(6) 3.106(3) 55602
C(30) O(2) 3.159(3) 45501
C(31) O(8) 3.543(5) 64602
C(31) C(11) 3.393(6) 45501
C(35) Br(1) 3.368(5) 45401
C(38) O(2) 3.575(7) 64602
Br(1) H(3) 3.49(3) 65501
Br(1) H(14) 3.30(3) 65601
Br(1) H(16) 3.47(3) 55601
Br(1) H(16) 3.38(3) 65601
Br(1) H(17) 3.10(3) 55601
Br(1) H(18) 3.31(3) 54602
O(2) H(7) 3.36(2) 65602
O(2) H(8) 3.16(2) 65501
O(2) H(23) 2.69(3) 65602
O(5) H(2) 3.28(3) 45501
O(5) H(4) 3.00(3) 45501
O(5) H(5) 2.57(3) 45501
O(6) H(5) 2.99(3) 45501
O(6) H(11) 3.08(3) 54602
O(6) H(23) 3.41(3) 45501
O(7) H(7) 3.32(2) 55602
O(7) H(14) 2.68(3) 65601
O(7) H(15) 3.54(4) 55601
O(7) H(16) 3.55(3) 55601
O(7) H(20) 2.89(3) 65601
O(7) H(21) 2.72(3) 55602
O(7) H(22) 3.31(5) 65602
O(8) H(9) 2.89(3) 65501
O(8) H(13) 3.14(4) 55602
O(28) H(2) 3.39(2) 45501
O(28) H(11) 3.31(3) 45501
O(28) H(14) 3.39(3) 55601
O(28) H(15) 3.29(3) 55601
O(28) H(16) 2.92(3) 55601
O(28) H(21) 3.27(3) 55602
N(16) H(8) 3.24(3) 65501
N(16) H(13) 3.54(4) 55602
N(19) H(16) 3.54(3) 55601
N(19) H(21) 3.04(3) 55602
C(9) H(8) 3.26(3) 65501
C(11) H(8) 3.42(3) 65501
C(11) H(13) 2.98(4) 65501
C(12) H(4) 3.56(3) 45501
C(13) H(2) 3.42(2) 45501
C(13) H(18) 2.93(4) 54602
C(13) H(19) 3.50(5) 54602
C(15) H(13) 3.59(4) 65501
C(15) H(18) 3.21(4) 54602
C(17) H(2) 3.57(3) 45501
C(18) H(13) 3.45(4) 65501
C(21) H(5) 3.47(2) 45501
C(22) H(22) 3.50(5) 45501
C(22) H(23) 3.51(3) 45501
C(23) H(2) 3.48(2) 45501
C(24) H(10) 3.10(4) 65501
C(25) H(15) 3.60(3) 45501
C(26) H(7) 3.46(2) 55602
C(26) H(8) 3.38(4) 65501
C(26) H(23) 3.47(3) 65602
C(31) H(2) 2.97(2) 45501
C(32) H(1) 3.59(2) 65501
C(32) H(6) 3.28(3) 65501
C(34) H(10) 3.30(4) 65501
C(35) H(1) 3.52(2) 65501
C(35) H(10) 2.88(4) 65501
C(36) H(1) 3.40(2) 65501
C(36) H(6) 3.51(2) 65501
C(36) H(19) 3.35(4) 54502
C(37) H(3) 3.26(3) 55602
C(37) H(17) 3.29(3) 55502
C(37) H(22) 3.24(4) 55502
C(38) H(6) 3.18(3) 65501
C(38) H(7) 3.50(2) 65501
C(38) H(11) 3.13(3) 64602
C(38) H(19) 3.34(6) 54502
H(1) C(32) 3.59(2) 45501
H(1) C(35) 3.52(2) 45501
H(1) C(36) 3.40(2) 45501
H(2) O(5) 3.28(3) 65501
H(2) O(28) 3.39(2) 65501
H(2) C(13) 3.42(2) 65501
H(2) C(17) 3.57(3) 65501
H(2) C(23) 3.48(2) 65501
H(2) C(31) 2.97(2) 65501
H(2) H(3) 3.51(4) 65501
H(2) H(8) 2.60(4) 65501
H(2) H(13) 2.76(5) 65501
H(3) Br(1) 3.49(3) 45501
H(3) C(37) 3.26(3) 54602
H(3) H(2) 3.51(4) 45501
H(3) H(16) 3.59(5) 55601
H(3) H(17) 3.11(5) 55601
H(3) H(18) 2.66(5) 54602
H(3) H(19) 2.83(6) 54602
H(4) O(5) 3.00(3) 65501
H(4) C(12) 3.56(3) 65501
H(4) H(9) 2.89(5) 65501
H(4) H(13) 3.55(5) 55602
H(5) O(5) 2.57(3) 65501
H(5) O(6) 2.99(3) 65501
H(5) C(21) 3.47(2) 65501
H(5) H(13) 3.53(4) 65501
H(6) C(32) 3.28(3) 45501
H(6) C(36) 3.51(2) 45501
H(6) C(38) 3.18(3) 45501
H(6) H(17) 3.58(4) 45501
H(6) H(22) 3.08(5) 45501
H(6) H(23) 2.86(4) 45501
H(7) O(2) 3.36(2) 64602
H(7) O(7) 3.32(2) 54602
H(7) C(26) 3.46(2) 54602
H(7) C(38) 3.50(2) 45501
H(7) H(11) 3.12(5) 54602
H(7) H(22) 3.08(5) 45501
H(7) H(23) 3.22(4) 45501
H(8) O(2) 3.16(2) 45501
H(8) N(16) 3.24(3) 45501
H(8) C(9) 3.26(3) 45501
H(8) C(11) 3.42(3) 45501
H(8) C(26) 3.38(4) 45501
H(8) H(2) 2.60(4) 45501
H(8) H(11) 3.40(5) 45501
H(9) O(8) 2.89(3) 45501
H(9) H(4) 2.89(5) 45501
H(9) H(12) 3.24(5) 45501
H(9) H(15) 3.57(4) 45501
H(10) C(24) 3.10(4) 45501
H(10) C(34) 3.30(4) 45501
H(10) C(35) 2.88(4) 45501
H(10) H(12) 3.57(6) 45501
H(10) H(15) 2.82(5) 45501
H(10) H(16) 2.79(5) 45501
H(11) O(6) 3.08(3) 55602
H(11) O(28) 3.31(3) 65501
H(11) C(38) 3.13(3) 65602
H(11) H(7) 3.12(5) 55602
H(11) H(8) 3.40(5) 65501
H(11) H(21) 3.34(4) 65602
H(11) H(22) 3.04(5) 65602
H(11) H(23) 2.56(5) 65602
H(12) H(9) 3.24(5) 65501
H(12) H(10) 3.57(6) 65501
H(13) O(8) 3.14(4) 54602
H(13) N(16) 3.54(4) 54602
H(13) C(11) 2.98(4) 45501
H(13) C(15) 3.59(4) 45501
H(13) C(18) 3.45(4) 45501
H(13) H(2) 2.76(5) 45501
H(13) H(4) 3.55(5) 54602
H(13) H(5) 3.53(4) 45501
H(14) Br(1) 3.30(3) 45401
H(14) O(7) 2.68(3) 45401
H(14) O(28) 3.39(3) 55401
H(14) H(16) 3.53(4) 45501
H(15) O(7) 3.54(4) 55401
H(15) O(28) 3.29(3) 55401
H(15) C(25) 3.60(3) 65501
H(15) H(9) 3.57(4) 65501
H(15) H(10) 2.82(5) 65501
H(15) H(20) 3.29(6) 65501
H(15) H(21) 3.16(5) 55502
H(15) H(22) 3.57(5) 55502
H(16) Br(1) 3.38(3) 45401
H(16) Br(1) 3.47(3) 55401
H(16) O(7) 3.55(3) 55401
H(16) O(28) 2.92(3) 55401
H(16) N(19) 3.54(3) 55401
H(16) H(3) 3.59(5) 55401
H(16) H(10) 2.79(5) 65501
H(16) H(14) 3.53(4) 65501
H(17) Br(1) 3.10(3) 55401
H(17) C(37) 3.29(3) 54502
H(17) H(3) 3.11(5) 55401
H(17) H(6) 3.58(4) 65501
H(17) H(18) 3.45(5) 54502
H(17) H(19) 2.59(5) 54502
H(17) H(20) 3.51(5) 54502
H(18) Br(1) 3.31(3) 55602
H(18) C(13) 2.93(4) 55602
H(18) C(15) 3.21(4) 55602
H(18) H(3) 2.66(5) 55602
H(18) H(17) 3.45(5) 55502
H(19) C(13) 3.50(5) 55602
H(19) C(36) 3.35(4) 55502
H(19) C(38) 3.34(6) 55502
H(19) H(3) 2.83(6) 55602
H(19) H(17) 2.59(5) 55502
H(19) H(21) 3.28(7) 55502
H(19) H(22) 2.68(7) 55502
H(20) O(7) 2.89(3) 45401
H(20) H(15) 3.29(6) 45501
H(20) H(17) 3.51(5) 55502
H(20) H(21) 3.34(5) 45502
H(20) H(22) 3.07(6) 55502
H(21) O(7) 2.72(3) 54602
H(21) O(28) 3.27(3) 54602
H(21) N(19) 3.04(3) 54602
H(21) H(11) 3.34(4) 64602
H(21) H(15) 3.16(5) 54502
H(21) H(19) 3.28(7) 54502
H(21) H(20) 3.34(5) 44502
H(22) O(7) 3.31(4) 64602
H(22) C(22) 3.50(5) 65501
H(22) C(37) 3.24(4) 54502
H(22) H(6) 3.08(5) 65501
H(22) H(7) 3.08(5) 65501
H(22) H(11) 3.04(5) 64602
H(22) H(15) 3.57(5) 54502
H(22) H(19) 2.68(7) 54502
H(22) H(20) 3.07(6) 54502
H(23) O(2) 2.69(3) 64602
H(23) O(6) 3.41(3) 65501
H(23) C(22) 3.51(3) 65501
H(23) C(26) 3.47(3) 64602
H(23) H(6) 2.86(4) 65501
H(23) H(7) 3.22(4) 65501
H(23) H(11) 2.56(5) 64602
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
C(21) O(3) C(22) C(29) 176.3(2)
C(22) O(3) C(21) O(6) 0.5(4)
C(22) O(3) C(21) C(17) -178.4(2)
C(10) O(4) C(12) O(5) 6.0(4)
C(10) O(4) C(12) C(20) -174.9(2)
C(12) O(4) C(10) C(25) 104.1(3)
C(12) O(4) C(10) C(33) -134.7(2)
O(2) N(16) C(9) C(14) -173.0(3)
O(2) N(16) C(9) C(26) 7.9(4)
O(8) N(16) C(9) C(14) 5.7(4)
O(8) N(16) C(9) C(26) -173.4(2)
O(7) N(19) C(30) C(23) -177.9(3)
O(7) N(19) C(30) C(26) -0.9(4)
O(28) N(19) C(30) C(23) 1.0(4)
O(28) N(19) C(30) C(26) 178.1(3)
N(16) C(9) C(14) C(20) 179.9(2)
N(16) C(9) C(26) C(30) 179.3(2)
C(14) C(9) C(26) C(30) 0.2(5)
C(26) C(9) C(14) C(20) -1.0(5)
O(4) C(10) C(25) C(27) 68.1(4)
O(4) C(10) C(33) C(24) -95.7(3)
O(4) C(10) C(33) C(29) 79.5(3)
C(25) C(10) C(33) C(24) 19.8(4)
C(25) C(10) C(33) C(29) -165.0(3)
C(33) C(10) C(25) C(27) -46.5(4)
C(15) C(11) C(18) C(17) -1.1(5)
C(18) C(11) C(15) Br(1) 179.8(2)
C(18) C(11) C(15) C(13) 1.2(5)
O(4) C(12) C(20) C(14) 8.6(4)
O(4) C(12) C(20) C(23) -175.8(2)
O(5) C(12) C(20) C(14) -172.2(3)
O(5) C(12) C(20) C(23) 3.4(4)
C(15) C(13) C(31) C(17) -0.7(6)
C(31) C(13) C(15) Br(1) -178.9(3)
C(31) C(13) C(15) C(11) -0.3(5)
C(9) C(14) C(20) C(12) 176.9(3)
C(9) C(14) C(20) C(23) 1.3(5)
C(18) C(17) C(21) O(3) -4.4(4)
C(18) C(17) C(21) O(6) 176.7(3)
C(21) C(17) C(18) C(11) 178.5(3)
C(18) C(17) C(31) C(13) 0.8(5)
C(31) C(17) C(18) C(11) 0.1(3)
C(21) C(17) C(31) C(13) -177.7(3)
C(31) C(17) C(21) O(3) 174.0(3)
C(31) C(17) C(21) O(6) -4.9(4)
C(12) C(20) C(23) C(30) -176.5(3)
C(14) C(20) C(23) C(30) -0.8(5)
O(3) C(22) C(29) C(32) 91.7(3)
O(3) C(22) C(29) C(33) -88.7(3)
C(20) C(23) C(30) N(19) 176.8(3)
C(20) C(23) C(30) C(26) -0.1(4)
C(33) C(24) C(34) C(27) 22.9(5)
C(34) C(24) C(33) C(10) -8.1(4)
C(34) C(24) C(33) C(29) 176.7(3)
C(33) C(24) C(35) C(36) 0.1(5)
C(35) C(24) C(33) C(10) 172.4(3)
C(35) C(24) C(33) C(29) -2.8(4)
C(34) C(24) C(35) C(36) -179.4(4)
C(35) C(24) C(34) C(27) -157.7(4)
C(10) C(25) C(27) C(34) 59.8(4)
C(10) C(25) C(27) C(37) -176.1(4)
C(9) C(26) C(30) N(19) -176.6(2)
C(9) C(26) C(30) C(23) 0.3(4)
C(25) C(27) C(34) C(24) -47.0(5)
C(37) C(27) C(34) C(24) -170.5(4)
C(22) C(29) C(32) C(36) 177.6(3)
C(22) C(29) C(32) C(38) -3.4(4)
C(22) C(29) C(33) C(10) 9.0(4)
C(22) C(29) C(33) C(24) -175.8(2)
C(32) C(29) C(33) C(10) -171.4(2)
C(32) C(29) C(33) C(24) 3.7(4)
C(33) C(29) C(32) C(36) -1.9(4)
C(33) C(29) C(32) C(38) 177.1(3)
C(29) C(32) C(36) C(35) -0.7(5)
C(38) C(32) C(36) C(35) -179.7(4)
C(24) C(35) C(36) C(32) 1.7(6)
