#------------------------------------------------------------------------------
#$Date: 2020-12-06 17:01:21 +0200 (Sun, 06 Dec 2020) $
#$Revision: 259631 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/97/1559711.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_1559711
loop_
_publ_author_name
'BLANGETTI, Marco'
'O’SHEA, Donal F.'
_publ_section_title
;
 Crystal Structure of
 rac-4-Iodo-5-methoxy[2.2]metacylophane; A Rare Example
 of a Halogenated Metacyclophane with Planar Chirality
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              45
_journal_page_last               46
_journal_paper_doi               10.2116/xraystruct.36.45
_journal_volume                  36
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H17 I O'
_chemical_formula_sum            'C17 H17 I O'
_chemical_formula_weight         364.21
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5690(2)
_cell_length_b                   14.2212(2)
_cell_length_c                   7.5004(1)
_cell_measurement_reflns_used    10303
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1236
_cell_measurement_theta_min      3.1049
_cell_volume                     1447.33(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20236
_diffrn_reflns_theta_full        76.32
_diffrn_reflns_theta_max         76.32
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    17.285
_exptl_absorpt_correction_T_max  0.697
_exptl_absorpt_correction_T_min  0.137
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) 
(compiled Jul 11 2012,15:38:31) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3162
_exptl_crystal_size_mid          0.0464
_exptl_crystal_size_min          0.0231
_refine_diff_density_max         1.708
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.088(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0281
_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)+(0.0426P)²+2.8557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                2941
_reflns_number_total             3021
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            36_45_1.txt
_cod_data_source_block           osh110
_cod_database_code               1559711
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 'x+1/2, -y, z'
4 '-x+1/2, y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9541(3) 0.8351(3) 1.0954(5) 0.0181(7) Uani 1 1 d . . .
I I 1.021995(14) 0.926116(14) 1.28017(7) 0.02185(9) Uani 1 1 d . . .
C2 C 0.8687(3) 0.8659(3) 1.0092(5) 0.0190(8) Uani 1 1 d . . .
O O 0.8363(2) 0.9535(2) 1.0560(4) 0.0237(6) Uani 1 1 d . . .
C7 C 0.7440(4) 0.9841(3) 0.9807(6) 0.0279(10) Uani 1 1 d . . .
H7a H 0.7512 0.9915 0.8514 0.042 Uiso 1 1 calc R . .
H7b H 0.7251 1.0445 1.0336 0.042 Uiso 1 1 calc R . .
H7c H 0.6930 0.9372 1.0058 0.042 Uiso 1 1 calc R . .
C3 C 0.8248(3) 0.8107(3) 0.8784(5) 0.0193(8) Uani 1 1 d . . .
H3 H 0.7699 0.8342 0.8135 0.023 Uiso 1 1 calc R . .
C4 C 0.8610(3) 0.7210(3) 0.8424(5) 0.0186(7) Uani 1 1 d . . .
C5 C 0.9401(3) 0.6873(3) 0.9453(5) 0.0185(8) Uani 1 1 d . . .
H5 H 0.9580 0.6229 0.9359 0.022 Uiso 1 1 calc R . .
C6 C 0.9933(3) 0.7453(3) 1.0610(6) 0.0199(8) Uani 1 1 d . . .
C8 C 0.8308(3) 0.6677(3) 0.6779(6) 0.0227(8) Uani 1 1 d . . .
H8a H 0.7623 0.6845 0.6455 0.027 Uiso 1 1 calc R . .
H8b H 0.8330 0.5993 0.7023 0.027 Uiso 1 1 calc R . .
C9 C 0.9016(3) 0.6917(3) 0.5190(6) 0.0230(8) Uani 1 1 d . . .
H9a H 0.8804 0.6570 0.4111 0.028 Uiso 1 1 calc R . .
H9b H 0.8982 0.7598 0.4928 0.028 Uiso 1 1 calc R . .
C10 C 1.0972(3) 0.7166(3) 1.1049(6) 0.0243(8) Uani 1 1 d . . .
H10a H 1.0999 0.6479 1.1259 0.029 Uiso 1 1 calc R . .
H10b H 1.1190 0.7488 1.2151 0.029 Uiso 1 1 calc R . .
C11 C 1.1674(3) 0.7432(3) 0.9476(6) 0.0244(8) Uani 1 1 d . . .
H11a H 1.1637 0.8117 0.9254 0.029 Uiso 1 1 calc R . .
H11b H 1.2362 0.7275 0.9801 0.029 Uiso 1 1 calc R . .
C12 C 1.0059(3) 0.6650(3) 0.5652(6) 0.0209(8) Uani 1 1 d . . .
C13 C 1.0607(3) 0.7243(3) 0.6796(5) 0.0204(8) Uani 1 1 d . . .
H13 H 1.0436 0.7889 0.6876 0.024 Uiso 1 1 calc R . .
C14 C 1.1388(2) 0.6905(2) 0.7802(9) 0.0215(6) Uani 1 1 d . . .
C15 C 1.1727(3) 0.5991(3) 0.7485(6) 0.0260(10) Uani 1 1 d . . .
H15 H 1.2270 0.5751 0.8144 0.031 Uiso 1 1 calc R . .
C16 C 1.1268(4) 0.5432(3) 0.6197(6) 0.0272(9) Uani 1 1 d . . .
H16 H 1.1533 0.4833 0.5904 0.033 Uiso 1 1 calc R . .
C17 C 1.0423(4) 0.5751(3) 0.5346(7) 0.0270(9) Uani 1 1 d . . .
H17 H 1.0088 0.5347 0.4540 0.032 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
C2 C1 I 118.3(3) . . ?
C2 C1 C6 120.9(4) . . ?
C6 C1 I 120.8(3) . . ?
O C2 C1 115.7(4) . . ?
O C2 C3 123.9(4) . . ?
C3 C2 C1 120.3(4) . . ?
C2 O C7 117.0(3) . . ?
O C7 H7a 109.5 . . ?
O C7 H7b 109.5 . . ?
O C7 H7c 109.5 . . ?
H7a C7 H7b 109.5 . . ?
H7a C7 H7c 109.5 . . ?
H7b C7 H7c 109.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.3(4) . . ?
C3 C4 C8 121.6(4) . . ?
C5 C4 C8 119.1(4) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.3(4) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C10 124.1(4) . . ?
C5 C6 C1 117.0(4) . . ?
C5 C6 C10 117.4(4) . . ?
C4 C8 H8a 109.6 . . ?
C4 C8 H8b 109.6 . . ?
C4 C8 C9 110.3(3) . . ?
H8a C8 H8b 108.1 . . ?
C9 C8 H8a 109.6 . . ?
C9 C8 H8b 109.6 . . ?
C8 C9 H9a 109.6 . . ?
C8 C9 H9b 109.6 . . ?
H9a C9 H9b 108.1 . . ?
C12 C9 C8 110.3(4) . . ?
C12 C9 H9a 109.6 . . ?
C12 C9 H9b 109.6 . . ?
C6 C10 H10a 109.7 . . ?
C6 C10 H10b 109.7 . . ?
C6 C10 C11 109.9(4) . . ?
H10a C10 H10b 108.2 . . ?
C11 C10 H10a 109.7 . . ?
C11 C10 H10b 109.7 . . ?
C10 C11 H11a 109.6 . . ?
C10 C11 H11b 109.6 . . ?
H11a C11 H11b 108.1 . . ?
C14 C11 C10 110.5(3) . . ?
C14 C11 H11a 109.6 . . ?
C14 C11 H11b 109.6 . . ?
C13 C12 C9 119.0(4) . . ?
C17 C12 C9 121.9(4) . . ?
C17 C12 C13 117.4(4) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.7(4) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C11 118.5(3) . . ?
C13 C14 C15 118.7(4) . . ?
C15 C14 C11 121.1(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.3(4) . . ?
C16 C17 H17 119.4 . . ?
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 I 2.109(4) . ?
C1 C2 1.397(6) . ?
C1 C6 1.407(6) . ?
C2 O 1.367(5) . ?
C2 C3 1.391(6) . ?
O C7 1.441(5) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.394(6) . ?
C4 C5 1.406(6) . ?
C4 C8 1.504(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(6) . ?
C6 C10 1.504(6) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.568(6) . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C9 C12 1.505(6) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C10 C11 1.563(6) . ?
C11 H11a 0.9900 . ?
C11 H11b 0.9900 . ?
C11 C14 1.513(7) . ?
C12 C13 1.414(6) . ?
C12 C17 1.390(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(6) . ?
C14 C15 1.399(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(7) . ?
C17 H17 0.9500 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 O C7 -174.9(4) . . . . ?
C1 C2 C3 C4 5.1(6) . . . . ?
C1 C6 C10 C11 -86.9(5) . . . . ?
I C1 C2 O -0.8(5) . . . . ?
I C1 C2 C3 176.1(3) . . . . ?
I C1 C6 C5 176.0(3) . . . . ?
I C1 C6 C10 -18.6(6) . . . . ?
C2 C1 C6 C5 -3.5(6) . . . . ?
C2 C1 C6 C10 162.0(4) . . . . ?
C2 C3 C4 C5 2.2(6) . . . . ?
C2 C3 C4 C8 -166.5(4) . . . . ?
O C2 C3 C4 -178.3(4) . . . . ?
C3 C2 O C7 8.3(6) . . . . ?
C3 C4 C5 C6 -10.5(6) . . . . ?
C3 C4 C8 C9 88.7(4) . . . . ?
C4 C5 C6 C1 11.1(6) . . . . ?
C4 C5 C6 C10 -155.4(4) . . . . ?
C4 C8 C9 C12 60.1(4) . . . . ?
C5 C4 C8 C9 -79.8(5) . . . . ?
C5 C6 C10 C11 78.4(5) . . . . ?
C6 C1 C2 O 178.7(4) . . . . ?
C6 C1 C2 C3 -4.5(6) . . . . ?
C6 C10 C11 C14 -62.5(5) . . . . ?
C8 C4 C5 C6 158.4(4) . . . . ?
C8 C9 C12 C13 -77.5(5) . . . . ?
C8 C9 C12 C17 87.2(5) . . . . ?
C9 C12 C13 C14 155.3(4) . . . . ?
C9 C12 C17 C16 -162.0(4) . . . . ?
C10 C11 C14 C13 80.4(5) . . . . ?
C10 C11 C14 C15 -84.6(5) . . . . ?
C11 C14 C15 C16 163.6(4) . . . . ?
C12 C13 C14 C11 -156.0(4) . . . . ?
C12 C13 C14 C15 9.3(7) . . . . ?
C13 C12 C17 C16 3.0(7) . . . . ?
C13 C14 C15 C16 -1.3(7) . . . . ?
C14 C15 C16 C17 -5.6(7) . . . . ?
C15 C16 C17 C12 4.7(8) . . . . ?
C17 C12 C13 C14 -10.1(6) . . . . ?
