#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:50:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180198 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/94/7109428.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_7109428
loop_
_publ_author_name
'Marco Blangetti'
'Helge Muller-Bunz'
'Donal F. O'Shea'
_publ_section_title
;
 First asymmetric synthesis of planar chiral [2.2]metacyclophanes
;
_journal_name_full               Chem.Commun.
_journal_page_first              6125
_journal_paper_doi               10.1039/c3cc42275e
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C18 H18 O3'
_chemical_formula_sum            'C18 H18 O3'
_chemical_formula_weight         282.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.909(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4948(2)
_cell_length_b                   14.0951(2)
_cell_length_c                   7.5300(1)
_cell_measurement_reflns_used    13681
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1054
_cell_measurement_theta_min      3.1336
_cell_volume                     1421.88(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_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            22791
_diffrn_reflns_theta_full        76.47
_diffrn_reflns_theta_max         76.47
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.2158
_exptl_crystal_size_mid          0.1231
_exptl_crystal_size_min          0.0393
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         5465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0353
_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)+(0.0556P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                2787
_reflns_number_total             2970
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3cc42275e.txt
_cod_data_source_block           osh104
_cod_original_cell_volume        1421.88(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7109428
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.15788(6) 0.55790(6) 0.67469(11) 0.01664(17) Uani 1 1 d .
C7 C 0.07458(7) 0.51721(6) 0.76496(12) 0.01857(17) Uani 1 1 d .
O1 O 0.08387(5) 0.51510(5) 0.93405(8) 0.02050(14) Uani 1 1 d .
H1O1 H 0.0286 0.5021 0.9687 0.031 Uiso 0.50 1 calc PR
O2 O -0.00327(5) 0.48675(6) 0.67209(9) 0.02605(16) Uani 1 1 d .
H1O2 H 0.0034 0.4915 0.5630 0.039 Uiso 0.50 1 calc PR
C2 C 0.14003(6) 0.64577(6) 0.58907(11) 0.01646(17) Uani 1 1 d .
O3 O 0.05149(5) 0.68688(5) 0.61678(9) 0.02039(14) Uani 1 1 d .
C8 C 0.03264(7) 0.78161(7) 0.55359(13) 0.0233(2) Uani 1 1 d .
H8A H 0.0874 0.8230 0.6033 0.035 Uiso 1 1 calc R
H8B H -0.0302 0.8043 0.5915 0.035 Uiso 1 1 calc R
H8C H 0.0278 0.7824 0.4227 0.035 Uiso 1 1 calc R
C3 C 0.20741(7) 0.68158(6) 0.47996(11) 0.01769(17) Uani 1 1 d .
H3 H 0.1934 0.7389 0.4156 0.021 Uiso 1 1 calc R
C4 C 0.29599(6) 0.63226(6) 0.46612(12) 0.01847(17) Uani 1 1 d .
C5 C 0.31818(6) 0.55143(7) 0.56928(12) 0.01910(18) Uani 1 1 d .
H5 H 0.3831 0.5246 0.5758 0.023 Uiso 1 1 calc R
C6 C 0.24652(7) 0.50880(6) 0.66382(12) 0.01769(17) Uani 1 1 d .
C9 C 0.35706(7) 0.65324(7) 0.31472(13) 0.02234(19) Uani 1 1 d .
H9A H 0.4287 0.6426 0.3559 0.027 Uiso 1 1 calc R
H9B H 0.3483 0.7206 0.2790 0.027 Uiso 1 1 calc R
C10 C 0.32401(7) 0.58786(7) 0.14892(12) 0.0234(2) Uani 1 1 d .
H10A H 0.2535 0.6012 0.1033 0.028 Uiso 1 1 calc R
H10B H 0.3654 0.6022 0.0523 0.028 Uiso 1 1 calc R
C11 C 0.25690(7) 0.40501(7) 0.71137(13) 0.02185(19) Uani 1 1 d .
H11A H 0.2171 0.3905 0.8103 0.026 Uiso 1 1 calc R
H11B H 0.3277 0.3904 0.7526 0.026 Uiso 1 1 calc R
C12 C 0.21977(7) 0.34193(7) 0.54453(14) 0.02367(19) Uani 1 1 d .
H12A H 0.2250 0.2740 0.5780 0.028 Uiso 1 1 calc R
H12B H 0.1489 0.3562 0.5036 0.028 Uiso 1 1 calc R
C13 C 0.33510(7) 0.48451(7) 0.19907(12) 0.02284(19) Uani 1 1 d .
C14 C 0.26163(7) 0.44166(7) 0.28852(13) 0.02156(19) Uani 1 1 d .
H14 H 0.1962 0.4677 0.2760 0.026 Uiso 1 1 calc R
C15 C 0.28234(7) 0.36159(7) 0.39568(13) 0.02281(19) Uani 1 1 d .
C16 C 0.37319(8) 0.31505(7) 0.38906(14) 0.0266(2) Uani 1 1 d .
H16 H 0.3875 0.2587 0.4565 0.032 Uiso 1 1 calc R
C17 C 0.44281(8) 0.35075(8) 0.28426(15) 0.0294(2) Uani 1 1 d .
H17 H 0.5023 0.3163 0.2734 0.035 Uiso 1 1 calc R
C18 C 0.42553(7) 0.43670(8) 0.19546(13) 0.0275(2) Uani 1 1 d .
H18 H 0.4756 0.4631 0.1318 0.033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.83(8)
C6 C1 C7 122.25(8)
C2 C1 C7 116.76(8)
O1 C7 O2 121.58(8)
O1 C7 C1 118.52(8)
O2 C7 C1 119.89(8)
C7 O1 H1O1 109.5
C7 O2 H1O2 109.5
O3 C2 C3 125.59(8)
O3 C2 C1 114.13(8)
C3 C2 C1 120.20(8)
C2 O3 C8 117.96(7)
O3 C8 H8A 109.5
O3 C8 H8B 109.5
H8A C8 H8B 109.5
O3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C2 C3 C4 119.28(8)
C2 C3 H3 120.4
C4 C3 H3 120.4
C5 C4 C3 119.63(8)
C5 C4 C9 118.71(8)
C3 C4 C9 120.46(8)
C4 C5 C6 121.26(8)
C4 C5 H5 119.4
C6 C5 H5 119.4
C1 C6 C5 117.79(8)
C1 C6 C11 121.58(8)
C5 C6 C11 119.07(8)
C4 C9 C10 110.80(7)
C4 C9 H9A 109.5
C10 C9 H9A 109.5
C4 C9 H9B 109.5
C10 C9 H9B 109.5
H9A C9 H9B 108.1
C13 C10 C9 110.93(8)
C13 C10 H10A 109.5
C9 C10 H10A 109.5
C13 C10 H10B 109.5
C9 C10 H10B 109.5
H10A C10 H10B 108.0
C6 C11 C12 110.33(8)
C6 C11 H11A 109.6
C12 C11 H11A 109.6
C6 C11 H11B 109.6
C12 C11 H11B 109.6
H11A C11 H11B 108.1
C15 C12 C11 109.70(8)
C15 C12 H12A 109.7
C11 C12 H12A 109.7
C15 C12 H12B 109.7
C11 C12 H12B 109.7
H12A C12 H12B 108.2
C18 C13 C14 118.14(10)
C18 C13 C10 121.45(9)
C14 C13 C10 118.84(9)
C15 C14 C13 121.50(9)
C15 C14 H14 119.2
C13 C14 H14 119.2
C14 C15 C16 118.34(9)
C14 C15 C12 119.15(9)
C16 C15 C12 120.84(9)
C17 C16 C15 120.38(10)
C17 C16 H16 119.8
C15 C16 H16 119.8
C18 C17 C16 120.16(9)
C18 C17 H17 119.9
C16 C17 H17 119.9
C17 C18 C13 120.49(10)
C17 C18 H18 119.8
C13 C18 H18 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3930(12)
C1 C2 1.4037(12)
C1 C7 1.4962(11)
C7 O1 1.2646(11)
C7 O2 1.2650(12)
O1 H1O1 0.8400
O2 H1O2 0.8400
C2 O3 1.3664(10)
C2 C3 1.3915(12)
O3 C8 1.4300(10)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C3 C4 1.3975(12)
C3 H3 0.9500
C4 C5 1.3911(13)
C4 C9 1.5141(11)
C5 C6 1.4030(12)
C5 H5 0.9500
C6 C11 1.5085(12)
C9 C10 1.5725(14)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C13 1.5077(14)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.5712(13)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C15 1.5080(14)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C18 1.3973(13)
C13 C14 1.4008(14)
C14 C15 1.3959(14)
C14 H14 0.9500
C15 C16 1.3965(13)
C16 C17 1.3918(16)
C16 H16 0.9500
C17 C18 1.3897(16)
C17 H17 0.9500
C18 H18 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
O2 H1O2 O2 0.84 1.80 2.6305(14) 171.9 3_566
O1 H1O1 O1 0.84 1.78 2.6139(13) 172.4 3_567
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
C6 C1 C7 O1 75.25(11)
C2 C1 C7 O1 -109.27(10)
C6 C1 C7 O2 -105.42(11)
C2 C1 C7 O2 70.06(11)
C6 C1 C2 O3 -177.87(8)
C7 C1 C2 O3 6.58(11)
C6 C1 C2 C3 5.17(13)
C7 C1 C2 C3 -170.38(8)
C3 C2 O3 C8 -10.90(12)
C1 C2 O3 C8 172.33(7)
O3 C2 C3 C4 179.20(8)
C1 C2 C3 C4 -4.21(12)
C2 C3 C4 C5 -3.77(13)
C2 C3 C4 C9 163.54(8)
C3 C4 C5 C6 11.09(13)
C9 C4 C5 C6 -156.44(8)
C2 C1 C6 C5 1.87(12)
C7 C1 C6 C5 177.17(8)
C2 C1 C6 C11 -163.71(8)
C7 C1 C6 C11 11.59(13)
C4 C5 C6 C1 -10.02(13)
C4 C5 C6 C11 155.94(9)
C5 C4 C9 C10 76.90(10)
C3 C4 C9 C10 -90.52(10)
C4 C9 C10 C13 -58.40(10)
C1 C6 C11 C12 86.60(10)
C5 C6 C11 C12 -78.80(10)
C6 C11 C12 C15 61.04(10)
C9 C10 C13 C18 -86.17(10)
C9 C10 C13 C14 79.31(10)
C18 C13 C14 C15 10.25(14)
C10 C13 C14 C15 -155.71(9)
C13 C14 C15 C16 -10.55(14)
C13 C14 C15 C12 154.87(9)
C11 C12 C15 C14 -80.39(10)
C11 C12 C15 C16 84.65(11)
C14 C15 C16 C17 2.97(14)
C12 C15 C16 C17 -162.19(9)
C15 C16 C17 C18 4.64(15)
C16 C17 C18 C13 -4.94(15)
C14 C13 C18 C17 -2.37(14)
C10 C13 C18 C17 163.20(9)
#BEGIN Loops that were not found in dictionaries:
loop_
_diffrn_twin_id
_diffrn_twin_ratio
_diffrn_twin_reflns_isolated
_diffrn_twin_reflns_overlapped
1 0.7722 13264 10055
2 0.2278 13162 10055
#END Loops that were not found in dictionaries
