#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/74/1507483.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_1507483
loop_
_publ_author_name
'Agatsuma, Tsutomu'
'Akama, Tsutomu'
'Nara, Shinji'
'Matsumiya, Shigeki'
'Nakai, Ryuichiro'
'Ogawa, Harumi'
'Otaki, Shizuo'
'Ikeda, Shun-ichi'
'Saitoh, Yutaka'
'Kanda, Yutaka'
_publ_section_title
;
 UCS1025A and B, New Antitumor Antibiotics from the
 FungusAcremoniumSpecies
;
_journal_issue                   25
_journal_name_full               'Organic Letters'
_journal_page_first              4387
_journal_paper_doi               10.1021/ol026923b
_journal_volume                  4
_journal_year                    2002
_chemical_compound_source
'slow evaporation of DMSO solution of 5; see text'
_chemical_formula_moiety         'C20 H24 Br N O5'
_chemical_formula_sum            'C20 H24 Br N O5'
_chemical_formula_weight         438.31
_chemical_name_systematic
; 
  (2aR,7S,7aS,7bR)-7-bromo-7-{[(4aS,5S,6S,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-
6-methylnaphthalene-5-yl]-oxomethyl}-2,2a,3,4,6,7,7a,7b-octahydro-
7b-hydroxy-furo[2,3,4-gh]pyrrolizine-2,6-dione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-93 with manual modification'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7230(3)
_cell_length_b                   9.4873(2)
_cell_length_c                   31.0788(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      32.94
_cell_measurement_theta_min      29.96
_cell_volume                     1982.30(12)
_computing_cell_refinement       'CAD4/PC V1.1 (Kretschmar, 1992)'
_computing_data_collection       'CAD4/PC V1.1 (Kretschmar, 1992)'
_computing_data_reduction
'CAD4 SDP-PLUS (B. A. Frenz & Associates & Enraf-Nonius, 1988)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material
'SHELXL-93 (Sheldrick, 1993) and PARST95 (Nardelli, 1983, 1995)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_sigmaI/netI    0.0908
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4911
_diffrn_reflns_theta_max         74.87
_diffrn_reflns_theta_min         2.84
_diffrn_standards_decay_%        9.24
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.089
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_correction_T_min  0.5389
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.042
_refine_ls_goodness_of_fit_obs   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_restrained_S_obs      1.076
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_obs          0.0561
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0441P)²+1.7880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1467
_refine_ls_wR_factor_obs         0.1262
_reflns_number_observed          2927
_reflns_number_total             4088
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ol026923bsi20021029_094314.cif
_cod_data_source_block           5_DMSO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+1.7880P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+1.7880P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               1507483
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
O1 O 0.7249(7) -0.2079(5) 0.0833(2) 0.0630(13) Uani 1 d
C2 C 0.6275(11) -0.2203(7) 0.0449(2) 0.058(2) Uani 1 d
C2A C 0.5294(9) -0.0835(7) 0.0325(2) 0.051(2) Uani 1 d
H2A H 0.3609(106) -0.0883(76) 0.0310(22) 0.074(21) Uiso 1 d
C3 C 0.5922(14) -0.0306(10) -0.0119(3) 0.071(2) Uani 1 d
H3A H 0.6402(113) -0.1322(101) -0.0318(26) 0.095(25) Uiso 1 d
H3B H 0.4880(112) -0.0014(93) -0.0224(27) 0.077(28) Uiso 1 d
C4 C 0.7586(12) 0.0779(10) -0.0039(3) 0.062(2) Uani 1 d
H4A H 0.8872(108) 0.0577(65) -0.0182(20) 0.051(17) Uiso 1 d
H4B H 0.7126(134) 0.1653(110) -0.0097(30) 0.103(32) Uiso 1 d
N5 N 0.7877(7) 0.0734(5) 0.0430(2) 0.0441(11) Uani 1 d
C6 C 0.9603(8) 0.0583(6) 0.0640(2) 0.0410(13) Uani 1 d
C7 C 0.9058(9) 0.0002(6) 0.1088(2) 0.0467(13) Uani 1 d
C7A C 0.7056(10) -0.0685(7) 0.1016(2) 0.054(2) Uani 1 d
H7A H 0.6173(96) -0.0726(66) 0.1296(22) 0.061(18) Uiso 1 d
C7B C 0.6132(9) 0.0189(6) 0.0653(2) 0.0464(13) Uani 1 d
O2X O 0.6292(9) -0.3294(5) 0.0257(2) 0.084(2) Uani 1 d
O6X O 1.1248(6) 0.0850(4) 0.04968(13) 0.0488(9) Uani 1 d
C7X C 0.8992(9) 0.1156(6) 0.1448(2) 0.0478(13) Uani 1 d
O7Y O 0.7601(6) 0.1131(6) 0.16949(15) 0.0653(13) Uani 1 d
Br7Z Br 1.11202(11) -0.13122(7) 0.12777(3) 0.0666(3) Uani 1 d
O7BX O 0.4951(6) 0.1296(6) 0.0790(2) 0.0673(14) Uani 1 d
H7BX H 0.3869(103) 0.1186(84) 0.0711(22) 0.064(21) Uiso 1 d
C1' C 1.0659(9) 0.2212(6) 0.1470(2) 0.0457(14) Uani 1 d
H1' H 1.1839(76) 0.1777(53) 0.1359(17) 0.032(14) Uiso 1 d
C2' C 1.0103(10) 0.3528(7) 0.1199(2) 0.057(2) Uani 1 d
H2' H 1.0143(91) 0.3178(69) 0.0929(22) 0.050(19) Uiso 1 d
C3' C 1.1558(14) 0.4678(7) 0.1283(3) 0.075(2) Uani 1 d
H3' H 1.1654(100) 0.5358(82) 0.1048(23) 0.066(21) Uiso 1 d
C4' C 1.2879(13) 0.4702(8) 0.1600(3) 0.073(2) Uani 1 d
H4' H 1.3805(109) 0.5565(80) 0.1617(22) 0.071(21) Uiso 1 d
C4A' C 1.3097(10) 0.3533(8) 0.1918(2) 0.058(2) Uani 1 d
H4A' H 1.4334(106) 0.2747(87) 0.1849(24) 0.078(23) Uiso 1 d
C5' C 1.3595(16) 0.4072(9) 0.2369(3) 0.083(3) Uani 1 d
H5'1 H 1.4910(114) 0.4601(83) 0.2365(25) 0.069(24) Uiso 1 d
H5'2 H 1.2457(163) 0.4702(123) 0.2500(32) 0.124(36) Uiso 1 d
C6' C 1.3896(21) 0.2873(12) 0.2680(4) 0.099(3) Uani 1 d
H6'1 H 1.5229(137) 0.2431(101) 0.2649(28) 0.089(30) Uiso 1 d
H6'2 H 1.3969(163) 0.3264(119) 0.2962(36) 0.133(39) Uiso 1 d
C7' C 1.2093(20) 0.1934(14) 0.2690(3) 0.098(3) Uani 1 d
H7'1 H 1.2163(187) 0.0952(150) 0.2873(40) 0.170(55) Uiso 1 d
H7'2 H 1.0889(115) 0.2355(85) 0.2777(25) 0.069(24) Uiso 1 d
C8' C 1.1550(14) 0.1400(10) 0.2236(2) 0.070(2) Uani 1 d
H8'1 H 1.0487(126) 0.0796(101) 0.2252(28) 0.091(31) Uiso 1 d
H8'2 H 1.2631(137) 0.0970(96) 0.2099(25) 0.090(30) Uiso 1 d
C8A' C 1.1197(10) 0.2633(6) 0.1934(2) 0.0502(13) Uani 1 d
H8A' H 1.0035(83) 0.3280(60) 0.2050(18) 0.038(15) Uiso 1 d
C2'X C 0.7949(13) 0.4065(8) 0.1262(3) 0.075(2) Uani 1 d
H2'1 H 0.7657(137) 0.4014(112) 0.1596(31) 0.109(32) Uiso 1 d
H2'2 H 0.6812(116) 0.3404(89) 0.1149(24) 0.080(25) Uiso 1 d
H2'3 H 0.7925(135) 0.5088(127) 0.1109(30) 0.119(34) Uiso 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'
Br Br -0.6763 1.2805 '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
C2 O1 C7A 112.3(5)
O2X C2 O1 120.4(7)
O2X C2 C2A 128.5(7)
O1 C2 C2A 111.0(5)
C2 C2A C7B 102.6(5)
C2 C2A C3 113.1(6)
C7B C2A C3 107.1(5)
C2A C3 C4 106.0(6)
N5 C4 C3 103.7(6)
C6 N5 C7B 115.2(5)
C6 N5 C4 127.0(5)
C7B N5 C4 112.0(5)
O6X C6 N5 125.8(6)
O6X C6 C7 128.3(5)
N5 C6 C7 105.8(5)
C7A C7 C6 103.5(5)
C7A C7 C7X 112.4(5)
C6 C7 C7X 113.7(5)
C7A C7 Br7Z 113.6(4)
C6 C7 Br7Z 109.4(4)
C7X C7 Br7Z 104.5(4)
O1 C7A C7 111.9(6)
O1 C7A C7B 103.9(5)
C7 C7A C7B 103.6(5)
O7BX C7B N5 109.8(5)
O7BX C7B C2A 118.6(5)
N5 C7B C2A 101.9(5)
O7BX C7B C7A 114.7(5)
N5 C7B C7A 102.5(5)
C2A C7B C7A 107.4(5)
O7Y C7X C1' 124.0(5)
O7Y C7X C7 117.5(6)
C1' C7X C7 118.6(5)
C7X C1' C8A' 113.1(5)
C7X C1' C2' 109.3(5)
C8A' C1' C2' 110.8(5)
C3' C2' C2'X 110.6(6)
C3' C2' C1' 109.6(6)
C2'X C2' C1' 115.0(6)
C4' C3' C2' 125.7(7)
C3' C4' C4A' 123.0(7)
C4' C4A' C5' 112.2(7)
C4' C4A' C8A' 110.6(6)
C5' C4A' C8A' 109.8(7)
C6' C5' C4A' 111.4(7)
C7' C6' C5' 110.6(9)
C6' C7' C8' 111.6(9)
C8A' C8' C7' 110.5(8)
C8' C8A' C4A' 108.5(6)
C8' C8A' C1' 114.6(6)
C4A' C8A' C1' 108.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.365(8)
O1 C7A 1.446(8)
C2 O2X 1.196(7)
C2 C2A 1.506(9)
C2A C7B 1.516(8)
C2A C3 1.527(11)
C3 C4 1.540(11)
C4 N5 1.471(9)
N5 C6 1.340(7)
N5 C7B 1.458(7)
C6 O6X 1.219(7)
C6 C7 1.541(9)
C7 C7A 1.512(9)
C7 C7X 1.566(8)
C7 Br7Z 1.956(6)
C7A C7B 1.532(9)
C7B O7BX 1.383(7)
C7X O7Y 1.211(7)
C7X C1' 1.504(8)
C1' C8A' 1.538(8)
C1' C2' 1.552(9)
C2' C3' 1.489(10)
C2' C2'X 1.547(11)
C3' C4' 1.327(11)
C4' C4A' 1.492(11)
C4A' C5' 1.529(10)
C4A' C8A' 1.537(9)
C5' C6' 1.508(14)
C6' C7' 1.50(2)
C7' C8' 1.541(12)
C8' C8A' 1.520(10)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O7BX H7BX O6X 0.78(7) 1.91(7) 2.684(6) 177(7) 1_455 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7A O1 C2 O2X -179.9(7)
C7A O1 C2 C2A 0.6(8)
O2X C2 C2A C7B -169.8(8)
O1 C2 C2A C7B 9.6(7)
O2X C2 C2A C3 -54.8(10)
O1 C2 C2A C3 124.6(6)
C2 C2A C3 C4 -97.1(7)
C7B C2A C3 C4 15.2(8)
C2A C3 C4 N5 3.3(9)
C3 C4 N5 C6 129.5(7)
C3 C4 N5 C7B -22.2(8)
C7B N5 C6 O6X 173.1(5)
C4 N5 C6 O6X 22.2(10)
C7B N5 C6 C7 -6.4(6)
C4 N5 C6 C7 -157.3(6)
O6X C6 C7 C7A -156.3(6)
N5 C6 C7 C7A 23.1(6)
O6X C6 C7 C7X 81.4(7)
N5 C6 C7 C7X -99.1(6)
O6X C6 C7 Br7Z -35.0(7)
N5 C6 C7 Br7Z 144.5(4)
C2 O1 C7A C7 -121.7(6)
C2 O1 C7A C7B -10.5(7)
C6 C7 C7A O1 81.2(6)
C7X C7 C7A O1 -155.7(5)
Br7Z C7 C7A O1 -37.3(7)
C6 C7 C7A C7B -30.1(6)
C7X C7 C7A C7B 92.9(6)
Br7Z C7 C7A C7B -148.6(4)
C6 N5 C7B O7BX 109.5(6)
C4 N5 C7B O7BX -95.2(7)
C6 N5 C7B C2A -123.9(5)
C4 N5 C7B C2A 31.4(7)
C6 N5 C7B C7A -12.8(6)
C4 N5 C7B C7A 142.5(6)
C2 C2A C7B O7BX -147.6(6)
C3 C2A C7B O7BX 93.1(7)
C2 C2A C7B N5 91.8(6)
C3 C2A C7B N5 -27.5(7)
C2 C2A C7B C7A -15.5(7)
C3 C2A C7B C7A -134.8(6)
O1 C7A C7B O7BX 150.3(5)
C7 C7A C7B O7BX -92.6(6)
O1 C7A C7B N5 -90.8(5)
C7 C7A C7B N5 26.3(6)
O1 C7A C7B C2A 16.2(7)
C7 C7A C7B C2A 133.3(5)
C7A C7 C7X O7Y 18.2(8)
C6 C7 C7X O7Y 135.4(6)
Br7Z C7 C7X O7Y -105.4(6)
C7A C7 C7X C1' -162.5(5)
C6 C7 C7X C1' -45.4(7)
Br7Z C7 C7X C1' 73.8(6)
O7Y C7X C1' C8A' 34.8(9)
C7 C7X C1' C8A' -144.4(5)
O7Y C7X C1' C2' -89.2(8)
C7 C7X C1' C2' 91.6(6)
C7X C1' C2' C3' 169.6(6)
C8A' C1' C2' C3' 44.3(8)
C7X C1' C2' C2'X 44.4(8)
C8A' C1' C2' C2'X -80.9(7)
C2'X C2' C3' C4' 115.1(10)
C1' C2' C3' C4' -12.7(12)
C2' C3' C4' C4A' 0.9(14)
C3' C4' C4A' C5' -143.8(9)
C3' C4' C4A' C8A' -20.8(11)
C4' C4A' C5' C6' -177.6(9)
C8A' C4A' C5' C6' 59.0(11)
C4A' C5' C6' C7' -56.2(13)
C5' C6' C7' C8' 54.9(13)
C6' C7' C8' C8A' -57.3(12)
C7' C8' C8A' C4A' 58.7(9)
C7' C8' C8A' C1' 179.6(8)
C4' C4A' C8A' C8' 176.0(6)
C5' C4A' C8A' C8' -59.6(8)
C4' C4A' C8A' C1' 51.1(7)
C5' C4A' C8A' C1' 175.6(6)
C7X C1' C8A' C8' 50.6(8)
C2' C1' C8A' C8' 173.8(6)
C7X C1' C8A' C4A' 171.7(5)
C2' C1' C8A' C4A' -65.1(7)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21200393 ChemSpider
