#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:42:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178820 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/74/4107444.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_4107444
loop_
_publ_author_name
'Pixu Li'
'Cory D. Evans'
'Yongzhong Wu'
'Bin Cao'
'Ernest Hamel'
'Madeleine M. Joullié'
_publ_section_title
;
 Evolution of the Total Syntheses of Ustiloxin Natural Products and Their
 Analogues
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2351
_journal_page_last               2364
_journal_paper_doi               10.1021/ja710363p
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C14 H27 N O4'
_chemical_formula_weight         273.37
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6012(1)
_cell_length_b                   14.8549(2)
_cell_length_c                   10.5616(1)
_cell_measurement_temperature    200(2)
_cell_volume                     1663.24(3)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_measurement_device       'image plate area detector'
_diffrn_measurement_device_type  'Rigaku R-AXIS IIc'
_diffrn_measurement_method       'phi oscillations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10067
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.31(246)
_refine_ls_extinction_coef       0.0437(71)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.117
_refine_ls_goodness_of_fit_obs   1.152
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_restrained_S_obs      1.152
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_obs          0.0704
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1100P)²+0.2310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2051
_refine_ls_wR_factor_obs         0.1977
_reflns_number_observed          2624
_reflns_number_total             2992
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja710363p-file005.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+0.2310P] 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^)+(0.1100P)^2^+0.2310P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4107444
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
_atom_site_refinement_flags
N1 N 0.2422(2) 0.72343(14) 0.1563(2) 0.0774(6) Uani 1 d .
C2 C 0.1991(3) 0.6945(2) 0.0313(4) 0.0848(9) Uani 1 d .
H2 H 0.1323(3) 0.7354(2) 0.0029(4) 0.113 Uiso 1 calc R
C3 C 0.1411(4) 0.6042(3) 0.0609(6) 0.126(2) Uani 1 d .
H3A H 0.0516(4) 0.6101(3) 0.0783(6) 0.168 Uiso 1 calc R
H3B H 0.1527(4) 0.5626(3) -0.0088(6) 0.168 Uiso 1 calc R
C5 C 0.2263(5) 0.6499(2) 0.2508(5) 0.1104(14) Uani 1 d .
C6 C 0.2507(3) 0.8120(2) 0.1842(3) 0.0707(7) Uani 1 d .
C9 C 0.2751(4) 0.9178(2) 0.3604(3) 0.0893(9) Uani 1 d .
C10 C 0.3799(5) 0.9708(3) 0.3036(6) 0.138(2) Uani 1 d .
H10A H 0.3620(5) 0.9820(3) 0.2160(6) 0.206 Uiso 1 calc R
H10B H 0.4571(5) 0.9375(3) 0.3107(6) 0.206 Uiso 1 calc R
H10C H 0.3881(5) 1.0270(3) 0.3476(6) 0.206 Uiso 1 calc R
C11 C 0.1487(4) 0.9643(3) 0.3394(6) 0.123(2) Uani 1 d .
H11A H 0.0827(4) 0.9290(3) 0.3768(6) 0.185 Uiso 1 calc R
H11B H 0.1335(4) 0.9705(3) 0.2502(6) 0.185 Uiso 1 calc R
H11C H 0.1503(4) 1.0228(3) 0.3780(6) 0.185 Uiso 1 calc R
C12 C 0.2983(7) 0.8980(4) 0.4994(5) 0.177(3) Uani 1 d .
H12A H 0.2289(7) 0.8638(4) 0.5327(5) 0.266 Uiso 1 calc R
H12B H 0.3057(7) 0.9536(4) 0.5452(5) 0.266 Uiso 1 calc R
H12C H 0.3748(7) 0.8640(4) 0.5083(5) 0.266 Uiso 1 calc R
C13 C 0.3025(3) 0.6908(2) -0.0718(4) 0.0974(11) Uani 1 d .
C14 C 0.4078(4) 0.6267(3) -0.0373(6) 0.142(2) Uani 1 d .
H14A H 0.4434(4) 0.6440(3) 0.0426(6) 0.212 Uiso 1 calc R
H14B H 0.4720(4) 0.6288(3) -0.1014(6) 0.212 Uiso 1 calc R
H14C H 0.3750(4) 0.5666(3) -0.0313(6) 0.212 Uiso 1 calc R
C16 C 0.2460(7) 0.6639(4) -0.1975(5) 0.141(2) Uani 1 d .
H16A H 0.3160(7) 0.6538(4) -0.2548(5) 0.188 Uiso 1 calc R
H16B H 0.2058(7) 0.6060(4) -0.1847(5) 0.188 Uiso 1 calc R
C17 C 0.1647(20) 0.7142(10) -0.2584(10) 0.411(14) Uani 1 d .
H17A H 0.1409(20) 0.6849(10) -0.3358(10) 0.616 Uiso 1 calc R
H17B H 0.2024(20) 0.7714(10) -0.2773(10) 0.616 Uiso 1 calc R
H17C H 0.0913(20) 0.7232(10) -0.2067(10) 0.616 Uiso 1 calc R
C18 C 0.1074(5) 0.6646(3) 0.3301(6) 0.141(2) Uani 1 d .
H18A H 0.1190(5) 0.7159(3) 0.3841(6) 0.212 Uiso 1 calc R
H18B H 0.0916(5) 0.6122(3) 0.3809(6) 0.212 Uiso 1 calc R
H18C H 0.0369(5) 0.6750(3) 0.2749(6) 0.212 Uiso 1 calc R
C19 C 0.3471(6) 0.6350(3) 0.3276(6) 0.155(2) Uani 1 d .
H19A H 0.3611(6) 0.6857(3) 0.3821(6) 0.233 Uiso 1 calc R
H19B H 0.4174(6) 0.6285(3) 0.2710(6) 0.233 Uiso 1 calc R
H19C H 0.3386(6) 0.5815(3) 0.3778(6) 0.233 Uiso 1 calc R
O4 O 0.2083(3) 0.5744(2) 0.1718(4) 0.1328(12) Uani 1 d .
O7 O 0.2434(2) 0.87061(12) 0.1047(2) 0.0845(6) Uani 1 d .
O8 O 0.2699(3) 0.82620(14) 0.3069(2) 0.0917(7) Uani 1 d .
O15 O 0.3568(3) 0.7779(2) -0.0861(3) 0.1289(11) Uani 1 d .
H15 H 0.3301(52) 0.8113(13) -0.0303(40) 0.193 Uiso 1 calc R
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 0.0000 0.0000 '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 0.0060 '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
C6 N1 C2 120.2(3)
C6 N1 C5 125.1(3)
C2 N1 C5 110.8(3)
N1 C2 C3 101.6(3)
N1 C2 C13 115.1(3)
C3 C2 C13 113.8(3)
O4 C3 C2 103.9(3)
O4 C5 N1 101.6(3)
O4 C5 C18 109.1(4)
N1 C5 C18 110.8(4)
O4 C5 C19 108.1(4)
N1 C5 C19 111.4(4)
C18 C5 C19 114.9(5)
O7 C6 O8 124.9(2)
O7 C6 N1 123.0(3)
O8 C6 N1 112.2(2)
O8 C9 C10 111.2(3)
O8 C9 C12 101.4(3)
C10 C9 C12 111.9(4)
O8 C9 C11 109.2(3)
C10 C9 C11 111.0(3)
C12 C9 C11 111.8(4)
O15 C13 C16 107.9(4)
O15 C13 C14 107.4(3)
C16 C13 C14 109.8(4)
O15 C13 C2 109.2(3)
C16 C13 C2 110.3(4)
C14 C13 C2 112.1(4)
C17 C16 C13 122.8(7)
C5 O4 C3 107.7(3)
C6 O8 C9 121.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.352(3)
N1 C2 1.462(5)
N1 C5 1.490(4)
C2 C3 1.508(5)
C2 C13 1.546(5)
C3 O4 1.441(7)
C5 O4 1.411(5)
C5 C18 1.529(7)
C5 C19 1.532(8)
C6 O7 1.212(3)
C6 O8 1.329(4)
C9 O8 1.475(4)
C9 C10 1.487(6)
C9 C12 1.518(6)
C9 C11 1.524(6)
C13 O15 1.425(4)
C13 C16 1.511(7)
C13 C14 1.512(7)
C16 C17 1.31(2)
