#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/15/4101505.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_4101505
loop_
_publ_author_name
'Bian, Jianwei'
'Van Wingerden, Matthew'
'Ready, Joseph M'
_publ_section_title
;
 Enantioselective total synthesis of (+)- and (-)-nigellamine A2.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7428
_journal_page_last               7429
_journal_paper_doi               10.1021/ja061559n
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C15 H15 I O3'
_chemical_formula_weight         370.000
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.000(3)
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   15.831(7)
_cell_length_b                   15.831(4)
_cell_length_c                   5.7920(14)
_cell_measurement_reflns_used    45
_cell_measurement_temperature    293(2)
_cell_volume                     1257.1(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       Collect
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1519
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       1
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            837
_diffrn_reflns_theta_full        20.74
_diffrn_reflns_theta_max         20.74
_diffrn_reflns_theta_min         4.36
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_coef       0.00(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.654
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         837
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.654
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002
_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          0.1583
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                603
_reflns_number_total             837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja061559nsi20060517_051336.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P3(2)
_cod_original_formula_sum        'C15 H15 I1    O3'
_cod_database_code               4101505
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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
I1 I 0.61738(16) 0.72148(13) 0.1549(4) 0.1425(15) Uani 1 1 d
C1 C 0.7332(17) 0.5415(17) 0.033(4) 0.099(7) Uani 1 1 d
C2 C 0.9230(12) 0.6242(13) 0.030(3) 0.073(5) Uani 1 1 d
O3 O 0.9309(9) 0.5535(10) -0.320(2) 0.082(4) Uani 1 1 d
O4 O 0.7232(8) 0.4635(11) 0.189(2) 0.082(4) Uani 1 1 d
C5 C 0.8261(14) 0.5830(14) -0.103(3) 0.073(5) Uani 1 1 d
O6 O 0.7926(9) 0.4229(9) -0.178(2) 0.081(4) Uani 1 1 d
C7 C 0.894(2) 0.761(3) -0.101(6) 0.141(10) Uani 1 1 d
C8 C 0.8308(14) 0.5138(14) -0.278(3) 0.078(5) Uani 1 1 d
C9 C 0.9854(13) 0.6027(13) -0.116(3) 0.071(4) Uani 1 1 d
C10 C 0.9579(15) 0.7332(17) 0.060(4) 0.091(6) Uani 1 1 d
C11 C 0.8361(19) 0.6756(17) -0.243(5) 0.102(7) Uani 1 1 d
C12 C 1.029(2) 0.7940(16) 0.214(5) 0.123(9) Uani 1 1 d
C13 C 1.055(3) 0.9038(17) 0.221(8) 0.161(14) Uani 1 1 d
C14 C 1.080(2) 0.755(2) 0.364(4) 0.128(10) Uani 1 1 d
C15 C 1.0177(18) 0.5346(16) -0.005(5) 0.107(7) Uani 1 1 d
C16 C 1.0761(18) 0.509(2) -0.162(6) 0.119(8) Uani 1 1 d
C17 C 1.1871(19) 0.587(3) -0.186(12) 0.26(4) Uani 1 1 d
C18 C 1.0369(17) 0.4247(19) -0.272(5) 0.110(7) 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 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
O4 C1 C5 111.1(19) .
C9 C2 C5 104.8(15) .
C9 C2 C10 114.8(15) .
C5 C2 C10 104.8(15) .
C8 O3 C9 109.8(13) .
C8 C5 C1 115.2(17) .
C8 C5 C11 107.6(16) .
C1 C5 C11 106.9(18) .
C8 C5 C2 104.0(16) .
C1 C5 C2 118.2(17) .
C11 C5 C2 104.1(16) .
C10 C7 C11 105(3) .
O6 C8 O3 110.4(16) .
O6 C8 C5 108.4(15) .
O3 C8 C5 104.1(14) .
C2 C9 O3 108.0(14) .
C2 C9 C15 114.7(18) .
O3 C9 C15 106.3(14) .
C12 C10 C7 127(2) .
C12 C10 C2 124(2) .
C7 C10 C2 109(2) .
C7 C11 C5 107(2) .
C10 C12 C13 117(3) .
C10 C12 C14 120(2) .
C13 C12 C14 122(3) .
C16 C15 C9 114(2) .
C18 C16 C15 122(2) .
C18 C16 C17 122(3) .
C15 C16 C17 116(2) .
C16 C18 I1 127(2) 3_664
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C18 2.05(3) 2_655
C1 O4 1.47(3) .
C1 C5 1.50(3) .
C2 C9 1.47(3) .
C2 C5 1.54(3) .
C2 C10 1.54(3) .
O3 C8 1.40(2) .
O3 C9 1.44(2) .
C5 C8 1.52(3) .
C5 C11 1.61(3) .
O6 C8 1.38(2) .
C7 C10 1.59(4) .
C7 C11 1.45(4) .
C9 C15 1.54(3) .
C10 C12 1.38(4) .
C12 C13 1.58(4) .
C12 C14 1.51(4) .
C15 C16 1.49(4) .
C16 C18 1.32(4) .
C16 C17 1.57(4) .
C18 I1 2.05(3) 3_664
