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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/77/7107786.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_7107786
loop_
_publ_author_name
'Amy J. Saunders'
'Ian R. Crossley'
'Martyn P. Coles'
'S. Mark Roe'
_publ_section_title
;
 Facile self-assembly of the first diphosphametacyclophane
;
_journal_name_full               Chem.Commun.
_journal_page_first              5766
_journal_paper_doi               10.1039/c2cc32247a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C18 H14 O4 P2'
_chemical_formula_sum            'C18 H14 O4 P2'
_chemical_formula_weight         356.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-10-06T10:22:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.317(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0985(9)
_cell_length_b                   7.6709(3)
_cell_length_c                   18.3347(13)
_cell_measurement_reflns_used    6247
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1674.07(18)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.757579E-1
_diffrn_orient_matrix_UB_12      -0.563531E-1
_diffrn_orient_matrix_UB_13      0.90122E-2
_diffrn_orient_matrix_UB_21      0.67278E-2
_diffrn_orient_matrix_UB_22      0.220999E-1
_diffrn_orient_matrix_UB_23      0.543693E-1
_diffrn_orient_matrix_UB_31      -0.356886E-1
_diffrn_orient_matrix_UB_32      -0.115457
_diffrn_orient_matrix_UB_33      0.60082E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8193
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.87
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.0054
_exptl_absorpt_correction_T_min  0.9536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.11
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.053
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0847P)²+0.2056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                2648
_reflns_number_total             3776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc32247a.txt
_cod_data_source_block           import
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7107786
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.0955(2) 0.1294(4) 0.16325(16) 0.0354(7) Uani 1 1 d .
C2 C 0.2075(2) 0.0443(3) 0.16831(15) 0.0325(6) Uani 1 1 d .
C3 C 0.3064(2) 0.1412(3) 0.18001(15) 0.0302(6) Uani 1 1 d .
H3 H 0.3034 0.2637 0.1868 0.036 Uiso 1 1 calc R
C4 C 0.4094(2) 0.0595(3) 0.18177(15) 0.0328(6) Uani 1 1 d .
C5 C 0.4125(3) -0.1218(4) 0.17473(16) 0.0392(7) Uani 1 1 d .
H5 H 0.4827 -0.1794 0.1779 0.047 Uiso 1 1 calc R
C6 C 0.3148(3) -0.2177(4) 0.16321(17) 0.0431(7) Uani 1 1 d .
H6 H 0.318 -0.3407 0.1579 0.052 Uiso 1 1 calc R
C7 C 0.2123(3) -0.1364(3) 0.15932(16) 0.0383(7) Uani 1 1 d .
H7 H 0.145 -0.203 0.1505 0.046 Uiso 1 1 calc R
C8 C 0.5160(2) 0.1617(4) 0.18943(16) 0.0368(7) Uani 1 1 d .
C9 C 0.4938(2) 0.3182(3) 0.05018(17) 0.0349(6) Uani 1 1 d .
C10 C 0.3814(2) 0.2557(3) 0.01161(15) 0.0322(6) Uani 1 1 d .
C11 C 0.2820(2) 0.3120(3) 0.03298(15) 0.0315(6) Uani 1 1 d .
H11 H 0.2848 0.3975 0.0708 0.038 Uiso 1 1 calc R
C12 C 0.1795(2) 0.2438(4) -0.00067(15) 0.0337(6) Uani 1 1 d .
C13 C 0.1755(3) 0.1229(4) -0.05817(18) 0.0446(8) Uani 1 1 d .
H13 H 0.1054 0.0769 -0.082 0.054 Uiso 1 1 calc R
C14 C 0.2739(3) 0.0703(4) -0.08023(18) 0.0495(8) Uani 1 1 d .
H14 H 0.2711 -0.0108 -0.1197 0.059 Uiso 1 1 calc R
C15 C 0.3755(3) 0.1347(4) -0.04546(17) 0.0404(7) Uani 1 1 d .
H15 H 0.4425 0.0962 -0.0605 0.049 Uiso 1 1 calc R
C16 C 0.0723(2) 0.2912(4) 0.02417(16) 0.0376(7) Uani 1 1 d .
C17 C -0.0695(3) 0.3882(5) 0.12517(19) 0.0482(8) Uani 1 1 d .
H17A H -0.0928 0.5043 0.1059 0.072 Uiso 1 1 calc R
H17B H -0.083 0.3775 0.1761 0.072 Uiso 1 1 calc R
H17C H -0.113 0.2993 0.094 0.072 Uiso 1 1 calc R
C18 C 0.6533(3) 0.4518(4) 0.1707(2) 0.0545(9) Uani 1 1 d .
H18A H 0.6717 0.493 0.2221 0.082 Uiso 1 1 calc R
H18B H 0.6676 0.5451 0.1371 0.082 Uiso 1 1 calc R
H18C H 0.7 0.3505 0.1644 0.082 Uiso 1 1 calc R
O1 O 0.01774(17) 0.0567(3) 0.18377(12) 0.0446(5) Uani 1 1 d .
O2 O 0.60542(18) 0.1023(3) 0.21759(13) 0.0532(6) Uani 1 1 d .
O3 O 0.57498(18) 0.3235(3) 0.01923(13) 0.0489(6) Uani 1 1 d .
O4 O -0.01692(18) 0.2899(3) -0.01805(12) 0.0552(6) Uani 1 1 d .
P1 P 0.07894(6) 0.35799(10) 0.12408(4) 0.0350(2) Uani 1 1 d .
P2 P 0.50611(6) 0.39025(9) 0.14968(5) 0.0367(2) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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 C2 121.8(3)
O1 C1 P1 120.6(2)
C2 C1 P1 117.6(2)
C3 C2 C7 119.7(3)
C3 C2 C1 121.4(2)
C7 C2 C1 118.9(3)
C4 C3 C2 120.3(2)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 119.0(3)
C3 C4 C8 121.4(2)
C5 C4 C8 119.6(2)
C6 C5 C4 120.6(3)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 120.4(3)
C5 C6 H6 119.8
C7 C6 H6 119.8
C6 C7 C2 119.9(3)
C6 C7 H7 120
C2 C7 H7 120
O2 C8 C4 122.5(3)
O2 C8 P2 120.4(2)
C4 C8 P2 117.08(19)
O3 C9 C10 122.0(3)
O3 C9 P2 120.6(2)
C10 C9 P2 117.3(2)
C15 C10 C11 119.1(3)
C15 C10 C9 119.3(3)
C11 C10 C9 121.6(2)
C12 C11 C10 120.3(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 119.6(3)
C11 C12 C16 121.9(2)
C13 C12 C16 118.4(3)
C14 C13 C12 119.9(3)
C14 C13 H13 120.1
C12 C13 H13 120.1
C15 C14 C13 120.3(3)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C10 120.8(3)
C14 C15 H15 119.6
C10 C15 H15 119.6
O4 C16 C12 121.7(3)
O4 C16 P1 120.1(2)
C12 C16 P1 118.2(2)
P1 C17 H17A 109.5
P1 C17 H17B 109.5
H17A C17 H17B 109.5
P1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
P2 C18 H18A 109.5
P2 C18 H18B 109.5
H18A C18 H18B 109.5
P2 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 P1 C16 100.06(14)
C17 P1 C1 98.76(14)
C16 P1 C1 95.73(13)
C18 P2 C9 100.73(15)
C18 P2 C8 99.60(14)
C9 P2 C8 95.14(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.211(3)
C1 C2 1.492(4)
C1 P1 1.892(3)
C2 C3 1.391(4)
C2 C7 1.398(4)
C3 C4 1.390(4)
C3 H3 0.95
C4 C5 1.398(4)
C4 C8 1.495(4)
C5 C6 1.376(4)
C5 H5 0.95
C6 C7 1.378(4)
C6 H6 0.95
C7 H7 0.95
C8 O2 1.202(3)
C8 P2 1.894(3)
C9 O3 1.220(3)
C9 C10 1.495(4)
C9 P2 1.886(3)
C10 C15 1.391(4)
C10 C11 1.398(4)
C11 C12 1.385(4)
C11 H11 0.95
C12 C13 1.398(4)
C12 C16 1.495(4)
C13 C14 1.384(4)
C13 H13 0.95
C14 C15 1.371(4)
C14 H14 0.95
C15 H15 0.95
C16 O4 1.210(3)
C16 P1 1.890(3)
C17 P1 1.815(3)
C17 H17A 0.98
C17 H17B 0.98
C17 H17C 0.98
C18 P2 1.816(3)
C18 H18A 0.98
C18 H18B 0.98
C18 H18C 0.98
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102199674
