#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/37/4023763.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_4023763
loop_
_publ_author_name
'Quan Zhou'
'Barry B. Snider'
_publ_section_title
;
 Synthesis of (+-)- and (-)-Vibralactone and Vibralactone C
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8049
_journal_page_last               8056
_journal_paper_doi               10.1021/jo8015743
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C12 H17 I1 O3'
_chemical_formula_sum            'C12 H17 I O3'
_chemical_formula_weight         336.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-07-08
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 99.115(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6159(2)
_cell_length_b                   24.3508(7)
_cell_length_c                   8.0178(2)
_cell_measurement_reflns_used    9412
_cell_measurement_temperature    120
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1275.38(6)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20486
_diffrn_reflns_theta_full        30.082
_diffrn_reflns_theta_max         30.082
_diffrn_reflns_theta_min         1.673
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.502
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 (Bruker AXS, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.63
_refine_diff_density_min         -0.81
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.003598
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)² + 1.09P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0564
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0564
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              34
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                3338
_reflns_number_total             3748
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0293
_oxford_refine_ls_scale          0.4405(4)
_oxford_reflns_number_all        3748
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'qz2_17_3_0m in P2(1)/n'
_cod_data_source_file            jo8015743_si_002.cif
_cod_data_source_block           racemic-21
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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      'P 1 21/n 1 '
_cod_original_formula_sum        'C12 H17 I1 O3'
_cod_database_code               4023763
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C1 C 0.6375(3) 0.66459(7) 0.8811(2) 0.0162 1.0000 Uani . . . . . . .
O2 O 0.7753(2) 0.65989(6) 0.77598(16) 0.0183 1.0000 Uani . . . . . . .
C3 C 0.9565(3) 0.63006(7) 0.8525(2) 0.0160 1.0000 Uani . . . . . . .
C4 C 0.9171(3) 0.61238(8) 1.0277(2) 0.0178 1.0000 Uani . . . . . . .
C5 C 0.7231(3) 0.64330(7) 1.0585(2) 0.0139 1.0000 Uani . . . . . . .
C6 C 0.5743(3) 0.60666(7) 1.1296(2) 0.0172 1.0000 Uani . . . . . . .
C7 C 0.4662(3) 0.62238(8) 1.2475(2) 0.0214 1.0000 Uani . . . . . . .
C8 C 0.4734(3) 0.67866(9) 1.3227(3) 0.0258 1.0000 Uani . . . . . . .
C9 C 0.5835(3) 0.71951(8) 1.2236(3) 0.0227 1.0000 Uani . . . . . . .
C10 C 0.7740(3) 0.69374(8) 1.1731(2) 0.0180 1.0000 Uani . . . . . . .
O11 O 0.4712(2) 0.68453(6) 0.83430(18) 0.0220 1.0000 Uani . . . . . . .
O12 O 0.8855(2) 0.73059(6) 1.08520(19) 0.0250 1.0000 Uani . . . . . . .
C13 C 1.0011(3) 0.58508(8) 0.7311(2) 0.0161 1.0000 Uani . . . . . . .
C14 C 1.0314(3) 0.60929(9) 0.5619(3) 0.0267 1.0000 Uani . . . . . . .
C15 C 1.1842(3) 0.55082(9) 0.8079(3) 0.0218 1.0000 Uani . . . . . . .
I1 I 0.733649(19) 0.530196(5) 0.682083(17) 0.0241 1.0000 Uani . . . . . . .
H121 H 0.921(5) 0.7564(14) 1.154(4) 0.046(9) 1.0000 Uiso . . . . . . .
H61 H 0.5563 0.5702 1.0874 0.0203 1.0000 Uiso R . . . . . .
H71 H 0.3785 0.5961 1.2866 0.0258 1.0000 Uiso R . . . . . .
H82 H 0.5441 0.6769 1.4353 0.0324 1.0000 Uiso R . . . . . .
H81 H 0.3374 0.6911 1.3234 0.0324 1.0000 Uiso R . . . . . .
H92 H 0.6217 0.7509 1.2918 0.0283 1.0000 Uiso R . . . . . .
H91 H 0.4934 0.7303 1.1247 0.0283 1.0000 Uiso R . . . . . .
H42 H 1.0299 0.6220 1.1113 0.0213 1.0000 Uiso R . . . . . .
H41 H 0.8954 0.5738 1.0303 0.0213 1.0000 Uiso R . . . . . .
H31 H 1.0687 0.6549 0.8672 0.0193 1.0000 Uiso R . . . . . .
H142 H 1.0587 0.5806 0.4884 0.0333 1.0000 Uiso R . . . . . .
H141 H 1.1436 0.6341 0.5783 0.0333 1.0000 Uiso R . . . . . .
H143 H 0.9110 0.6283 0.5133 0.0333 1.0000 Uiso R . . . . . .
H152 H 1.2089 0.5231 0.7301 0.0263 1.0000 Uiso R . . . . . .
H153 H 1.3013 0.5737 0.8325 0.0263 1.0000 Uiso R . . . . . .
H151 H 1.1567 0.5341 0.9090 0.0263 1.0000 Uiso R . . . . . .
H101 H 0.8606 0.6822 1.2729 0.0219 1.0000 Uiso R . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . C1 . C5 . 111.43(15) yes
O2 . C1 . O11 . 121.06(17) yes
C5 . C1 . O11 . 127.50(17) yes
C1 . O2 . C3 . 112.03(13) yes
O2 . C3 . C4 . 106.22(14) yes
O2 . C3 . C13 . 108.64(14) yes
C4 . C3 . C13 . 117.53(15) yes
O2 . C3 . H31 . 108.1 no
C4 . C3 . H31 . 108.0 no
C13 . C3 . H31 . 108.0 no
C3 . C4 . C5 . 106.06(14) yes
C3 . C4 . H42 . 110.4 no
C5 . C4 . H42 . 110.3 no
C3 . C4 . H41 . 110.3 no
C5 . C4 . H41 . 110.3 no
H42 . C4 . H41 . 109.5 no
C4 . C5 . C1 . 102.21(14) yes
C4 . C5 . C6 . 112.47(15) yes
C1 . C5 . C6 . 112.51(15) yes
C4 . C5 . C10 . 112.12(15) yes
C1 . C5 . C10 . 107.30(14) yes
C6 . C5 . C10 . 109.94(15) yes
C5 . C6 . C7 . 123.81(17) yes
C5 . C6 . H61 . 118.1 no
C7 . C6 . H61 . 118.1 no
C6 . C7 . C8 . 124.39(18) yes
C6 . C7 . H71 . 117.8 no
C8 . C7 . H71 . 117.8 no
C7 . C8 . C9 . 111.99(17) yes
C7 . C8 . H82 . 108.7 no
C9 . C8 . H82 . 108.7 no
C7 . C8 . H81 . 109.0 no
C9 . C8 . H81 . 109.0 no
H82 . C8 . H81 . 109.5 no
C8 . C9 . C10 . 110.72(17) yes
C8 . C9 . H92 . 109.3 no
C10 . C9 . H92 . 109.2 no
C8 . C9 . H91 . 109.0 no
C10 . C9 . H91 . 109.1 no
H92 . C9 . H91 . 109.5 no
C5 . C10 . C9 . 112.13(15) yes
C5 . C10 . O12 . 106.88(14) yes
C9 . C10 . O12 . 112.95(16) yes
C5 . C10 . H101 . 108.3 no
C9 . C10 . H101 . 108.2 no
O12 . C10 . H101 . 108.3 no
C10 . O12 . H121 . 105(2) no
C3 . C13 . C14 . 110.93(16) yes
C3 . C13 . C15 . 110.99(15) yes
C14 . C13 . C15 . 111.39(16) yes
C3 . C13 . I1 . 108.58(12) yes
C14 . C13 . I1 . 106.98(13) yes
C15 . C13 . I1 . 107.80(12) yes
C13 . C14 . H142 . 109.4 no
C13 . C14 . H141 . 109.5 no
H142 . C14 . H141 . 109.5 no
C13 . C14 . H143 . 109.5 no
H142 . C14 . H143 . 109.5 no
H141 . C14 . H143 . 109.5 no
C13 . C15 . H152 . 109.4 no
C13 . C15 . H153 . 109.5 no
H152 . C15 . H153 . 109.5 no
C13 . C15 . H151 . 109.4 no
H152 . C15 . H151 . 109.5 no
H153 . C15 . H151 . 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . O2 . 1.341(2) yes
C1 . C5 . 1.535(2) yes
C1 . O11 . 1.207(2) yes
O2 . C3 . 1.452(2) yes
C3 . C4 . 1.530(2) yes
C3 . C13 . 1.525(2) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.541(2) yes
C4 . H42 . 0.950 no
C4 . H41 . 0.950 no
C5 . C6 . 1.506(3) yes
C5 . C10 . 1.539(2) yes
C6 . C7 . 1.329(3) yes
C6 . H61 . 0.950 no
C7 . C8 . 1.495(3) yes
C7 . H71 . 0.950 no
C8 . C9 . 1.528(3) yes
C8 . H82 . 0.950 no
C8 . H81 . 0.950 no
C9 . C10 . 1.520(3) yes
C9 . H92 . 0.950 no
C9 . H91 . 0.950 no
C10 . O12 . 1.418(2) yes
C10 . H101 . 0.950 no
O12 . H121 . 0.84(3) no
C13 . C14 . 1.521(3) yes
C13 . C15 . 1.519(3) yes
C13 . I1 . 2.2023(18) yes
C14 . H142 . 0.950 no
C14 . H141 . 0.950 no
C14 . H143 . 0.950 no
C15 . H152 . 0.950 no
C15 . H153 . 0.950 no
C15 . H151 . 0.950 no
