#------------------------------------------------------------------------------
#$Date: 2018-01-06 04:36:47 +0200 (Sat, 06 Jan 2018) $
#$Revision: 204891 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/79/1547917.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_1547917
loop_
_publ_author_name
'Lim, Ngiap-Kie'
'Weiss, Patrick'
'Li, Beryl X.'
'McCulley, Christina H.'
'Hare, Stephanie R.'
'Bensema, Bronwyn L.'
'Palazzo, Teresa A.'
'Tantillo, Dean J.'
'Zhang, Haiming'
'Gosselin, Francis'
_publ_section_title
;
 Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-Carbon
 Olefins via a Syn-Elimination Approach.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6212
_journal_page_last               6215
_journal_paper_doi               10.1021/acs.orglett.7b03141
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C22 H21 I O'
_chemical_formula_weight         428.29
_chemical_name_common            60473-74
_chemical_name_systematic        gene626
_space_group.centring_type       P
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.5150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1357(4)
_cell_length_b                   6.0494(2)
_cell_length_c                   25.0871(10)
_cell_measurement_reflns_used    9657
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.48
_cell_volume                     1829.84(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27715
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.378
_diffrn_reflns_theta_min         1.634
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    1.755
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0070P)²+3.5796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0649
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3149
_reflns_number_total             3365
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b03141_si_022.cif
_cod_data_source_block           60473-74
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 

 Adding full bibliography for 1547906--1547941.cif.
;
_cod_database_code               1547917
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.933
_shelx_estimated_absorpt_t_max   0.949
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.2971(2) 0.4884(4) 0.62651(11) 0.0176(6) Uani 1 1 d . .
C2 C 0.1898(2) 0.6215(4) 0.60815(11) 0.0155(6) Uani 1 1 d . .
H2 H 0.2063 0.7801 0.6170 0.019 Uiso 1 1 calc R U
C3 C 0.1585(2) 0.6084(5) 0.54711(11) 0.0189(6) Uani 1 1 d . .
H3A H 0.2259 0.6311 0.5289 0.023 Uiso 1 1 calc R U
H3B H 0.1294 0.4589 0.5376 0.023 Uiso 1 1 calc R U
C4 C 0.0721(3) 0.7795(5) 0.52711(12) 0.0251(7) Uani 1 1 d . .
H4A H 0.0039 0.7529 0.5436 0.038 Uiso 1 1 calc R U
H4B H 0.0563 0.7685 0.4880 0.038 Uiso 1 1 calc R U
H4C H 0.1003 0.9277 0.5368 0.038 Uiso 1 1 calc R U
C5 C 0.0920(2) 0.5555(5) 0.63786(10) 0.0169(6) Uani 1 1 d . .
C6 C 0.0494(2) 0.7037(5) 0.67279(11) 0.0202(6) Uani 1 1 d . .
H6 H 0.0843 0.8433 0.6791 0.024 Uiso 1 1 calc R U
C7 C -0.0424(3) 0.6523(5) 0.69848(12) 0.0268(7) Uani 1 1 d . .
H7 H -0.0697 0.7563 0.7221 0.032 Uiso 1 1 calc R U
C8 C -0.0944(3) 0.4502(5) 0.68983(12) 0.0266(7) Uani 1 1 d . .
H8 H -0.1575 0.4146 0.7073 0.032 Uiso 1 1 calc R U
C9 C -0.0533(3) 0.3002(5) 0.65532(12) 0.0257(7) Uani 1 1 d . .
H9 H -0.0885 0.1607 0.6493 0.031 Uiso 1 1 calc R U
C10 C 0.0381(2) 0.3512(5) 0.62956(11) 0.0206(6) Uani 1 1 d . .
H10 H 0.0649 0.2465 0.6059 0.025 Uiso 1 1 calc R U
C11 C 0.3204(2) 0.4975(4) 0.68785(11) 0.0173(6) Uani 1 1 d . .
C12 C 0.2973(3) 0.3212(5) 0.71997(12) 0.0235(7) Uani 1 1 d . .
H12 H 0.2674 0.1883 0.7042 0.028 Uiso 1 1 calc R U
C13 C 0.3180(3) 0.3395(5) 0.77540(13) 0.0282(7) Uani 1 1 d . .
H13 H 0.3034 0.2171 0.7973 0.034 Uiso 1 1 calc R U
C14 C 0.3594(3) 0.5320(5) 0.79918(12) 0.0268(7) Uani 1 1 d . .
H14 H 0.3714 0.5436 0.8372 0.032 Uiso 1 1 calc R U
C15 C 0.3834(3) 0.7085(5) 0.76730(12) 0.0243(7) Uani 1 1 d . .
H15 H 0.4134 0.8410 0.7833 0.029 Uiso 1 1 calc R U
C16 C 0.3635(2) 0.6907(5) 0.71208(11) 0.0205(6) Uani 1 1 d . .
H16 H 0.3796 0.8124 0.6903 0.025 Uiso 1 1 calc R U
C17 C 0.3993(2) 0.5763(5) 0.60268(10) 0.0174(6) Uani 1 1 d . .
C18 C 0.4928(2) 0.4405(5) 0.60468(11) 0.0208(6) Uani 1 1 d . .
H18 H 0.4889 0.2941 0.6181 0.025 Uiso 1 1 calc R U
C19 C 0.5906(3) 0.5142(5) 0.58765(11) 0.0239(7) Uani 1 1 d . .
H19 H 0.6535 0.4200 0.5895 0.029 Uiso 1 1 calc R U
C20 C 0.5959(2) 0.7267(5) 0.56786(11) 0.0210(6) Uani 1 1 d . .
C21 C 0.5044(2) 0.8642(5) 0.56454(11) 0.0203(6) Uani 1 1 d . .
H21 H 0.5082 1.0091 0.5502 0.024 Uiso 1 1 calc R U
C22 C 0.4073(2) 0.7888(4) 0.58222(11) 0.0199(6) Uani 1 1 d . .
H22 H 0.3448 0.8841 0.5804 0.024 Uiso 1 1 calc R U
O1 O 0.28143(17) 0.2598(3) 0.61148(8) 0.0217(4) Uani 1 1 d . .
H1 H 0.2728 0.2492 0.5779 0.033 Uiso 1 1 calc R U
I1 I 0.74550(2) 0.85449(4) 0.54600(2) 0.03006(8) 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'
H H 0.0000 0.0000 '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
O1 C1 C17 108.6(2)
O1 C1 C11 107.5(2)
C17 C1 C11 108.3(2)
O1 C1 C2 109.8(2)
C17 C1 C2 113.1(2)
C11 C1 C2 109.3(2)
C5 C2 C3 110.9(2)
C5 C2 C1 113.0(2)
C3 C2 C1 111.8(2)
C5 C2 H2 106.9
C3 C2 H2 106.9
C1 C2 H2 106.9
C4 C3 C2 112.1(2)
C4 C3 H3A 109.2
C2 C3 H3A 109.2
C4 C3 H3B 109.2
C2 C3 H3B 109.2
H3A C3 H3B 107.9
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C6 C5 C10 117.4(3)
C6 C5 C2 120.2(2)
C10 C5 C2 122.3(2)
C7 C6 C5 121.6(3)
C7 C6 H6 119.2
C5 C6 H6 119.2
C8 C7 C6 120.2(3)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C9 119.2(3)
C7 C8 H8 120.4
C9 C8 H8 120.4
C10 C9 C8 120.7(3)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C5 120.9(3)
C9 C10 H10 119.6
C5 C10 H10 119.6
C12 C11 C16 118.9(3)
C12 C11 C1 122.0(2)
C16 C11 C1 119.0(2)
C11 C12 C13 119.7(3)
C11 C12 H12 120.2
C13 C12 H12 120.2
C14 C13 C12 121.1(3)
C14 C13 H13 119.4
C12 C13 H13 119.4
C13 C14 C15 119.5(3)
C13 C14 H14 120.3
C15 C14 H14 120.3
C16 C15 C14 119.6(3)
C16 C15 H15 120.2
C14 C15 H15 120.2
C15 C16 C11 121.1(3)
C15 C16 H16 119.4
C11 C16 H16 119.4
C22 C17 C18 117.8(3)
C22 C17 C1 123.9(3)
C18 C17 C1 118.2(2)
C19 C18 C17 121.5(3)
C19 C18 H18 119.3
C17 C18 H18 119.3
C18 C19 C20 119.2(3)
C18 C19 H19 120.4
C20 C19 H19 120.4
C21 C20 C19 120.8(3)
C21 C20 I1 118.3(2)
C19 C20 I1 120.8(2)
C20 C21 C22 119.3(3)
C20 C21 H21 120.3
C22 C21 H21 120.3
C21 C22 C17 121.4(3)
C21 C22 H22 119.3
C17 C22 H22 119.3
C1 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.441(3)
C1 C17 1.532(4)
C1 C11 1.534(4)
C1 C2 1.556(4)
C2 C5 1.524(4)
C2 C3 1.537(4)
C2 H2 1.0000
C3 C4 1.518(4)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C6 1.393(4)
C5 C10 1.403(4)
C6 C7 1.385(4)
C6 H6 0.9500
C7 C8 1.381(4)
C7 H7 0.9500
C8 C9 1.385(4)
C8 H8 0.9500
C9 C10 1.381(4)
C9 H9 0.9500
C10 H10 0.9500
C11 C12 1.384(4)
C11 C16 1.392(4)
C12 C13 1.389(4)
C12 H12 0.9500
C13 C14 1.377(4)
C13 H13 0.9500
C14 C15 1.385(4)
C14 H14 0.9500
C15 C16 1.383(4)
C15 H15 0.9500
C16 H16 0.9500
C17 C22 1.392(4)
C17 C18 1.397(4)
C18 C19 1.380(4)
C18 H18 0.9500
C19 C20 1.382(4)
C19 H19 0.9500
C20 C21 1.382(4)
C20 I1 2.103(3)
C21 C22 1.382(4)
C21 H21 0.9500
C22 H22 0.9500
O1 H1 0.8400
