#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151226.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_7151226
loop_
_publ_author_name
'Clarkson, Guy'
'Livingston, Andrew G.'
'Muir, Jennifer C.'
'Taylor, Paul C.'
_publ_section_title
;
 The absolute configuration of (+)-(E)-4-phenylbut-3-ene-2-ol.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2081
_journal_paper_doi               10.1039/b603934k
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H16 I N O2'
_chemical_formula_weight         393.21
_chemical_name_systematic
;
4-iodophenyl carbamate of 4-phenylbut-3-ene-2-ol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.311(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9131(9)
_cell_length_b                   5.0982(5)
_cell_length_c                   18.2642(17)
_cell_measurement_reflns_used    2894
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      26.84
_cell_measurement_theta_min      2.28
_cell_volume                     810.85(14)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Siemens SMART diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5524
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         29.25
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_T_max  0.9251
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.335
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 'Flack H D (1983), 1492 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3697
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0637P)²+0.4933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                3116
_reflns_number_total             3697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b603934k.txt
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7151226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8679(9) 0.6181(15) 1.4420(4) 0.0520(17) Uani 1 1 d . . .
H1A H 0.9374 0.4752 1.4533 0.062 Uiso 1 1 calc R . .
C2 C 0.7657(10) 0.6641(15) 1.4875(4) 0.059(2) Uani 1 1 d . . .
H2A H 0.7651 0.5531 1.5293 0.071 Uiso 1 1 calc R . .
C3 C 0.6633(9) 0.8729(18) 1.4724(5) 0.061(2) Uani 1 1 d . . .
H3A H 0.5914 0.9042 1.5030 0.074 Uiso 1 1 calc R . .
C4 C 0.6677(9) 1.0320(17) 1.4128(5) 0.058(2) Uani 1 1 d . . .
H4A H 0.5982 1.1752 1.4022 0.070 Uiso 1 1 calc R . .
C5 C 0.7715(8) 0.9882(15) 1.3678(4) 0.0492(16) Uani 1 1 d . . .
H5A H 0.7749 1.1048 1.3276 0.059 Uiso 1 1 calc R . .
C6 C 0.8725(7) 0.772(2) 1.3808(3) 0.0424(15) Uani 1 1 d . . .
C7 C 0.9756(7) 0.7248(19) 1.3282(3) 0.0417(13) Uani 1 1 d . . .
H7A H 0.9889 0.8636 1.2955 0.050 Uiso 1 1 calc R . .
C8 C 1.0496(7) 0.5050(12) 1.3236(4) 0.0391(13) Uani 1 1 d . . .
H8A H 1.0377 0.3672 1.3569 0.047 Uiso 1 1 calc R . .
C9 C 1.1524(8) 0.4554(13) 1.2693(4) 0.0394(13) Uani 1 1 d . . .
H9A H 1.1720 0.6223 1.2441 0.047 Uiso 1 1 calc R . .
O10 O 1.0787(4) 0.2623(15) 1.21376(19) 0.0358(9) Uani 1 1 d . . .
C10 C 1.3019(8) 0.3317(15) 1.3082(4) 0.0498(18) Uani 1 1 d . . .
H10A H 1.3591 0.2750 1.2707 0.075 Uiso 1 1 calc R . .
H10B H 1.2808 0.1796 1.3372 0.075 Uiso 1 1 calc R . .
H10C H 1.3630 0.4600 1.3419 0.075 Uiso 1 1 calc R . .
O12 O 0.9590(5) 0.5909(8) 1.1392(2) 0.0394(10) Uani 1 1 d . . .
C12 C 0.9809(7) 0.3576(11) 1.1528(4) 0.0306(11) Uani 1 1 d . . .
N13 N 0.9138(6) 0.1569(8) 1.1092(3) 0.0315(10) Uani 1 1 d . . .
H13A H 0.9366 -0.0031 1.1259 0.038 Uiso 1 1 calc R . .
C14 C 0.8119(6) 0.1815(8) 1.0401(3) 0.0267(12) Uani 1 1 d . . .
C15 C 0.6958(7) -0.0050(11) 1.0194(4) 0.0368(13) Uani 1 1 d . . .
H15A H 0.6863 -0.1434 1.0529 0.044 Uiso 1 1 calc R . .
C16 C 0.5948(7) 0.0093(12) 0.9508(4) 0.0410(14) Uani 1 1 d . . .
H16A H 0.5162 -0.1186 0.9375 0.049 Uiso 1 1 calc R . .
I17 I 0.44951(4) 0.24463(12) 0.79893(2) 0.05312(16) Uani 1 1 d . . .
C17 C 0.6078(6) 0.2106(16) 0.9011(3) 0.0374(14) Uani 1 1 d . . .
C18 C 0.7243(7) 0.3929(12) 0.9202(3) 0.0367(13) Uani 1 1 d . . .
H18A H 0.7347 0.5278 0.8858 0.044 Uiso 1 1 calc R . .
C19 C 0.8259(7) 0.3812(12) 0.9889(4) 0.0351(12) Uani 1 1 d . . .
H19A H 0.9052 0.5082 1.0015 0.042 Uiso 1 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.1(8) . . ?
C6 C1 H1A 119.0 . . ?
C2 C1 H1A 119.0 . . ?
C1 C2 C3 120.0(8) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 119.0(7) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C3 C4 C5 121.0(7) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 120.7(7) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C1 C6 C5 117.1(6) . . ?
C1 C6 C7 124.2(8) . . ?
C5 C6 C7 118.7(7) . . ?
C8 C7 C6 124.8(8) . . ?
C8 C7 H7A 117.6 . . ?
C6 C7 H7A 117.6 . . ?
C7 C8 C9 124.7(6) . . ?
C7 C8 H8A 117.6 . . ?
C9 C8 H8A 117.6 . . ?
O10 C9 C10 105.4(5) . . ?
O10 C9 C8 108.8(5) . . ?
C10 C9 C8 111.1(6) . . ?
O10 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C12 O10 C9 116.4(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O12 C12 O10 124.4(6) . . ?
O12 C12 N13 125.7(6) . . ?
O10 C12 N13 109.9(6) . . ?
C12 N13 C14 125.8(4) . . ?
C12 N13 H13A 117.1 . . ?
C14 N13 H13A 117.1 . . ?
N13 C14 C15 119.1(5) . . ?
N13 C14 C19 122.2(5) . . ?
C15 C14 C19 118.6(5) . . ?
C16 C15 C14 120.8(6) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C15 C16 C17 120.2(6) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C18 C17 C16 119.6(5) . . ?
C18 C17 I17 119.8(5) . . ?
C16 C17 I17 120.6(5) . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C18 C19 C14 120.0(6) . . ?
C18 C19 H19A 120.0 . . ?
C14 C19 H19A 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.375(11) . ?
C1 C2 1.378(11) . ?
C1 H1A 0.9500 . ?
C2 C3 1.391(11) . ?
C2 H2A 0.9500 . ?
C3 C4 1.364(13) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(11) . ?
C4 H4A 0.9500 . ?
C5 C6 1.409(11) . ?
C5 H5A 0.9500 . ?
C6 C7 1.484(8) . ?
C7 C8 1.312(11) . ?
C7 H7A 0.9500 . ?
C8 C9 1.509(9) . ?
C8 H8A 0.9500 . ?
C9 O10 1.465(8) . ?
C9 C10 1.508(9) . ?
C9 H9A 1.0000 . ?
O10 C12 1.349(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O12 C12 1.222(7) . ?
C12 N13 1.356(7) . ?
N13 C14 1.393(8) . ?
N13 H13A 0.8800 . ?
C14 C15 1.397(8) . ?
C14 C19 1.406(8) . ?
C15 C16 1.379(10) . ?
C15 H15A 0.9500 . ?
C16 C17 1.392(10) . ?
C16 H16A 0.9500 . ?
I17 C17 2.093(6) . ?
C17 C18 1.381(9) . ?
C18 C19 1.383(9) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
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
N13 H13A O12 0.88 2.09 2.949(6) 165.7 1_545
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9684211
