#------------------------------------------------------------------------------
#$Date: 2017-03-04 09:48:34 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/22/4032222.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_4032222
loop_
_publ_author_name
'Taher, Ehab S.'
'Guest, Prue'
'Benton, Amanda'
'Ma, Xinghua'
'Banwell, Martin G.'
'Willis, Anthony C.'
'Seiser, Tobias'
'Newton, Trevor W.'
'Hutzler, Johannes'
_publ_section_title
;
 The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation
 as Herbicidal Agents.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              211
_journal_page_last               233
_journal_paper_doi               10.1021/acs.joc.6b02372
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         'C7 H11 I O4, H2 O'
_chemical_formula_sum            'C7 H13 I O5'
_chemical_formula_weight         304.08
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             14-10-17
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-10-28 - Report on C7 H13 I O5
            by Anthony C. Willis
            for  Prue Guest and Martin Banwell


2014-10-28 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 111.360(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5832(15)
_cell_length_b                   4.7115(1)
_cell_length_c                   13.4131(8)
_cell_measurement_reflns_used    4515
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     1034.86(14)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_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      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5958
_diffrn_reflns_theta_full        71.869
_diffrn_reflns_theta_max         71.869
_diffrn_reflns_theta_min         3.538
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    24.296
_exptl_absorpt_correction_T_max  0.57
_exptl_absorpt_correction_T_min  0.12
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.023
_refine_diff_density_max         1.28
_refine_diff_density_min         -0.75
_refine_ls_abs_structure_details 'Flack (1983), 761 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.011(8)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1906
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.0018024
_refine_ls_shift/su_mean         0.0002264
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.59P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0594
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0594
_reflns_limit_h_max              20
_reflns_limit_h_min              -21
_reflns_limit_k_max              5
_reflns_limit_k_min              -5
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1871
_reflns_number_total             1906
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.40
_oxford_diffrn_Wilson_scale      0.08
_oxford_refine_ls_r_factor_ref   0.0222
_oxford_refine_ls_scale          3.55(4)
_oxford_reflns_number_all        1906
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\ban1454SN\Tony_ban1454SN_data At 9:19 on '
_cod_data_source_file            jo6b02372_si_005.cif
_cod_data_source_block           ban1454SN
_cod_original_sg_symbol_Hall     'C 2y '
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_database_code               4032222
_iucr_refine_instruction_details_constraints
;
#
# Punched on 17/10/14 at 16:56:30
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  83,X'S) H   (  82,X'S) 
RIDE O   (   9,X'S) H   (  91,X'S) 
RIDE O   (  10,X'S) H   ( 101,X'S) 
RIDE O   (  11,X'S) H   ( 111,X'S) 
RIDE O   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 17/10/14 at 16:56:30
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,z
-x,y,-z
-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
C1 C 0.7229(2) 0.4520(8) 0.6345(3) 0.0225 1.0000 Uani .
C2 C 0.6325(3) 0.5146(9) 0.6081(4) 0.0225 1.0000 Uani .
C3 C 0.6098(2) 0.4253(8) 0.7035(3) 0.0216 1.0000 Uani .
C4 C 0.6662(2) 0.5761(7) 0.8027(3) 0.0228 1.0000 Uani .
C5 C 0.74122(18) 0.6593(12) 0.8157(2) 0.0248 1.0000 Uani .
C6 C 0.77594(17) 0.6315(13) 0.7283(2) 0.0229 1.0000 Uani .
O7 O 0.85500(16) 0.5022(7) 0.7670(2) 0.0312 1.0000 Uani .
C8 C 0.9172(2) 0.6763(14) 0.8402(3) 0.0372 1.0000 Uani .
O9 O 0.74615(18) 0.5046(6) 0.5453(2) 0.0289 1.0000 Uani .
O10 O 0.61564(19) 0.8091(7) 0.5916(3) 0.0247 1.0000 Uani .
O11 O 0.52542(15) 0.4663(6) 0.6824(2) 0.0263 1.0000 Uani .
I12 I 0.623313(11) 0.6443(2) 0.928295(14) 0.0334 1.0000 Uani .
O13 O 0.94138(15) 0.4639(6) 0.6215(2) 0.0261 1.0000 Uani .
H11 H 0.7336 0.2540 0.6532 0.0268 1.0000 Uiso R
H21 H 0.5994 0.4062 0.5455 0.0266 1.0000 Uiso R
H31 H 0.6198 0.2207 0.7134 0.0259 1.0000 Uiso R
H51 H 0.7744 0.7350 0.8805 0.0298 1.0000 Uiso R
H61 H 0.7822 0.8215 0.7034 0.0279 1.0000 Uiso R
H81 H 0.9689 0.5992 0.8475 0.0556 1.0000 Uiso R
H83 H 0.9108 0.6791 0.9074 0.0557 1.0000 Uiso R
H82 H 0.9145 0.8641 0.8147 0.0556 1.0000 Uiso R
H91 H 0.7390 0.6701 0.5268 0.0441 1.0000 Uiso R
H101 H 0.6049 0.8482 0.5285 0.0368 1.0000 Uiso R
H111 H 0.5134 0.6363 0.6700 0.0396 1.0000 Uiso R
H131 H 0.9567 0.6264 0.6220 0.0392 1.0000 Uiso R
H132 H 0.9082 0.4513 0.6507 0.0395 1.0000 Uiso R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0248(17) 0.0200(16) 0.0256(17) 0.0020(14) 0.0127(14) 0.0021(13)
C2 0.0218(17) 0.0217(18) 0.023(2) 0.0009(15) 0.0068(14) -0.0001(15)
C3 0.0184(15) 0.0235(16) 0.0233(16) -0.0012(14) 0.0081(13) 0.0005(13)
C4 0.0232(15) 0.029(3) 0.0175(14) 0.0020(12) 0.0087(12) 0.0044(13)
C5 0.0204(13) 0.0307(19) 0.0217(13) 0.000(2) 0.0058(11) 0.001(2)
C6 0.0190(12) 0.0243(15) 0.0266(14) -0.002(2) 0.0096(11) -0.001(2)
O7 0.0178(12) 0.0401(16) 0.0365(15) 0.0014(13) 0.0109(11) 0.0053(12)
C8 0.0193(14) 0.060(3) 0.0313(17) -0.008(2) 0.0084(13) 0.004(2)
O9 0.0433(16) 0.0194(12) 0.0329(15) 0.0001(12) 0.0243(13) 0.0005(12)
O10 0.0294(14) 0.0215(14) 0.0238(14) 0.0011(11) 0.0105(12) 0.0032(11)
O11 0.0194(12) 0.0264(14) 0.0336(14) -0.0022(11) 0.0102(10) -0.0023(10)
I12 0.03079(13) 0.04840(15) 0.02537(12) 0.00122(17) 0.01538(9) 0.00558(16)
O13 0.0215(11) 0.0305(14) 0.0306(13) -0.0053(11) 0.0147(10) -0.0019(10)
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 0.0181 0.0091 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'
I -0.3257 6.8362 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'
O 0.0492 0.0322 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 111.0(3) yes
C2 C1 O9 111.5(3) yes
C6 C1 O9 108.7(3) yes
C2 C1 H11 109.6 no
C6 C1 H11 108.6 no
O9 C1 H11 107.3 no
C1 C2 C3 108.6(3) yes
C1 C2 O10 111.5(3) yes
C3 C2 O10 107.2(4) yes
C1 C2 H21 110.1 no
C3 C2 H21 108.7 no
O10 C2 H21 110.7 no
C2 C3 C4 108.5(3) yes
C2 C3 O11 111.6(3) yes
C4 C3 O11 114.4(3) yes
C2 C3 H31 107.1 no
C4 C3 H31 108.3 no
O11 C3 H31 106.6 no
C3 C4 C5 123.8(3) yes
C3 C4 I12 117.6(2) yes
C5 C4 I12 118.6(3) yes
C4 C5 C6 122.4(3) yes
C4 C5 H51 119.7 no
C6 C5 H51 117.8 no
C1 C6 C5 112.9(3) yes
C1 C6 O7 106.6(4) yes
C5 C6 O7 111.7(3) yes
C1 C6 H61 109.8 no
C5 C6 H61 108.3 no
O7 C6 H61 107.4 no
C6 O7 C8 113.8(4) yes
O7 C8 H81 108.4 no
O7 C8 H83 109.6 no
H81 C8 H83 110.3 no
O7 C8 H82 111.3 no
H81 C8 H82 108.4 no
H83 C8 H82 108.9 no
C1 O9 H91 111.3 no
C2 O10 H101 109.8 no
C3 O11 H111 110.1 no
H131 O13 H132 111.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.526(5) yes
C1 C6 1.521(5) yes
C1 O9 1.421(4) yes
C1 H11 0.967 no
C2 C3 1.532(6) yes
C2 O10 1.419(4) yes
C2 H21 0.974 no
C3 C4 1.516(5) yes
C3 O11 1.418(4) yes
C3 H31 0.980 no
C4 C5 1.326(5) yes
C4 I12 2.106(3) yes
C5 C6 1.512(4) yes
C5 H51 0.924 no
C6 O7 1.431(4) yes
C6 H61 0.976 no
O7 C8 1.432(6) yes
C8 H81 0.951 no
C8 H83 0.948 no
C8 H82 0.944 no
O9 H91 0.814 no
O10 H101 0.817 no
O11 H111 0.830 no
O13 H131 0.811 no
O13 H132 0.815 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
I12 O11 3.226(3) . no
O7 O9 2.891(4) . no
O7 O13 2.882(4) . no
O9 O9 2.677(4) 4_656 no
O9 O10 2.958(5) . no
O9 O13 3.211(4) . no
O9 C1 3.393(5) 4_656 no
O9 O9 2.677(4) 4_646 no
O10 O11 2.831(5) . no
O10 C5 3.094(5) . no
O10 C2 3.337(5) 1_565 no
O10 O13 2.760(4) 4_656 no
O10 C3 3.287(5) 1_565 no
O11 O13 2.752(4) 2_445 no
O11 O13 2.733(4) 2_455 no
O13 C8 3.270(5) . no
O13 O7 2.882(4) . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O9 H91 O9 4_656 155 0.81 1.92 2.676(6) yes
O10 H101 O13 4_656 169 0.82 1.95 2.759(6) yes
O11 H111 O13 2_455 157 0.83 1.95 2.733(6) yes
O13 H131 O11 2_555 156 0.81 1.99 2.753(6) yes
O13 H132 O7 . 160 0.82 2.11 2.883(6) 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
_geom_torsion_publ_flag
C8 O7 C6 C5 -68.9(5) no
C8 O7 C6 C1 167.3(3) no
O9 C1 C2 C3 174.4(3) no
O9 C1 C2 O10 -67.8(5) no
O9 C1 C6 O7 -73.9(4) no
C6 C1 C2 O10 53.7(5) no
C6 C1 C2 C3 -64.2(4) no
C2 C1 C6 C5 40.2(5) no
C2 C1 C6 O7 163.1(3) no
O9 C1 C6 C5 163.1(4) no
O10 C2 C3 C4 -65.0(4) no
O10 C2 C3 O11 62.0(4) no
C1 C2 C3 O11 -177.4(3) no
C1 C2 C3 C4 55.6(4) no
O11 C3 C4 I12 29.0(4) no
C2 C3 C4 C5 -27.7(5) no
O11 C3 C4 C5 -153.0(4) no
C2 C3 C4 I12 154.3(3) no
I12 C4 C5 C6 -177.2(4) no
C3 C4 C5 C6 4.8(7) no
C4 C5 C6 C1 -10.7(7) no
C4 C5 C6 O7 -130.8(4) no
