#------------------------------------------------------------------------------
#$Date: 2022-01-26 03:09:37 +0100 (Wed 26 de Jan de 2022) $
#$Revision: 272241 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/42/7244298.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_7244298
loop_
_publ_author_name
'Oßwald, Simon'
'Zippel, Christoph'
'Hassan, Zahid'
'Nieger, Martin'
'Bräse, Stefan'
_publ_section_title
;
 C--P bond formation of cyclophanyl-, and aryl halides via a UV-induced
 photo Arbuzov reaction: a versatile portal to phosphonate-grafted
 scaffolds
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              3309
_journal_page_last               3312
_journal_paper_doi               10.1039/D2RA00094F
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H26 O6 P2'
_chemical_formula_sum            'C20 H26 O6 P2'
_chemical_formula_weight         424.35
_chemical_name_systematic
;
tetramethyl 1,4(1,4)-dibenzenacyclohexaphane-1²,1⁵-diylbis(phosphonate)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-08-16 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.1103(13)
_cell_length_b                   21.6232(14)
_cell_length_c                   8.7121(6)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.2
_cell_measurement_theta_min      4.1
_cell_volume                     3976.8(4)
_computing_cell_refinement       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2016)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16792
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.199
_diffrn_reflns_theta_min         5.858
_diffrn_source                   'INCOATEC microfocus sealed tube'
_exptl_absorpt_coefficient_mu    2.293
_exptl_absorpt_correction_T_max  0.8894
_exptl_absorpt_correction_T_min  0.7534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       plates
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0213
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0336P)²+3.5595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0599
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1954
_reflns_number_total             1959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra00094f2.cif
_cod_data_source_block           sb1390_hy_compound_3b
_cod_database_code               7244298
_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   0.657
_shelx_estimated_absorpt_t_max   0.914
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.43475(10) 0.50356(10) 0.1669(3) 0.0248(4) Uani 1 1 d . . . . .
H1 H 0.3900 0.5063 0.1565 0.030 Uiso 1 1 calc R U . . .
C2 C 0.47112(10) 0.55733(10) 0.1656(3) 0.0256(4) Uani 1 1 d . . . . .
H2 H 0.4511 0.5963 0.1526 0.031 Uiso 1 1 calc R U . . .
C3 C 0.53653(10) 0.55429(10) 0.1834(2) 0.0245(4) Uani 1 1 d . . . . .
C4 C 0.57224(10) 0.60823(10) 0.2513(3) 0.0288(5) Uani 1 1 d . . . . .
H4A H 0.5590 0.6467 0.1989 0.035 Uiso 1 1 calc R U . . .
H4B H 0.6181 0.6025 0.2327 0.035 Uiso 1 1 calc R U . . .
C5 C 0.56026(9) 0.61533(9) 0.4313(3) 0.0244(4) Uani 1 1 d . . . . .
H5A H 0.6010 0.6244 0.4831 0.029 Uiso 1 1 calc R U . . .
H5B H 0.5314 0.6507 0.4495 0.029 Uiso 1 1 calc R U . . .
C6 C 0.53165(9) 0.55742(9) 0.5002(2) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.46623(9) 0.55432(8) 0.5190(2) 0.0192(4) Uani 1 1 d . . . . .
H7 H 0.4428 0.5916 0.5295 0.023 Uiso 1 1 calc R U . . .
C8 C 0.43413(9) 0.49770(9) 0.5227(2) 0.0179(4) Uani 1 1 d . . . . .
P1 P 0.34950(2) 0.49533(2) 0.54258(6) 0.01941(14) Uani 1 1 d . . . . .
O11 O 0.31238(7) 0.47134(7) 0.41365(19) 0.0291(3) Uani 1 1 d . . . . .
O12 O 0.33428(6) 0.56421(7) 0.59102(18) 0.0247(3) Uani 1 1 d . . . . .
C12 C 0.26871(10) 0.58305(11) 0.6012(3) 0.0313(5) Uani 1 1 d . . . . .
H12A H 0.2484 0.5782 0.5007 0.047 Uiso 1 1 calc R U . . .
H12B H 0.2665 0.6265 0.6329 0.047 Uiso 1 1 calc R U . . .
H12C H 0.2468 0.5572 0.6768 0.047 Uiso 1 1 calc R U . . .
O13 O 0.33660(7) 0.45386(7) 0.68950(18) 0.0262(3) Uani 1 1 d . . . . .
C13 C 0.36432(13) 0.47005(11) 0.8352(3) 0.0350(5) Uani 1 1 d . . . . .
H13A H 0.4070 0.4865 0.8188 0.053 Uiso 1 1 calc R U . . .
H13B H 0.3667 0.4332 0.9004 0.053 Uiso 1 1 calc R U . . .
H13C H 0.3381 0.5015 0.8856 0.053 Uiso 1 1 calc R U . . .
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'
P P 0.2955 0.4335 '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 C3 120.6(2) . 2_665 ?
C2 C1 H1 119.7 . . ?
C3 C1 H1 119.7 2_665 . ?
C3 C2 C1 120.46(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C1 117.5(2) . 2_665 ?
C2 C3 C4 120.19(19) . . ?
C1 C3 C4 121.01(19) 2_665 . ?
C3 C4 C5 112.37(16) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 111.91(17) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C8 116.88(17) . 2_665 ?
C7 C6 C5 118.82(17) . . ?
C8 C6 C5 123.40(17) 2_665 . ?
C6 C7 C8 121.67(17) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C6 119.28(17) . 2_665 ?
C7 C8 P1 120.58(14) . . ?
C6 C8 P1 120.00(14) 2_665 . ?
O11 P1 O12 115.45(9) . . ?
O11 P1 O13 109.06(9) . . ?
O12 P1 O13 106.39(9) . . ?
O11 P1 C8 117.93(9) . . ?
O12 P1 C8 101.61(8) . . ?
O13 P1 C8 105.36(9) . . ?
C12 O12 P1 118.46(13) . . ?
O12 C12 H12A 109.5 . . ?
O12 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O12 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 O13 P1 120.25(13) . . ?
O13 C13 H13A 109.5 . . ?
O13 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O13 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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 C2 1.393(3) . ?
C1 C3 1.398(3) 2_665 ?
C1 H1 0.9500 . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C1 1.398(3) 2_665 ?
C3 C4 1.510(3) . ?
C4 C5 1.596(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.514(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.392(3) . ?
C6 C8 1.407(3) 2_665 ?
C7 C8 1.400(3) . ?
C7 H7 0.9500 . ?
C8 C6 1.407(3) 2_665 ?
C8 P1 1.7956(18) . ?
P1 O11 1.4646(16) . ?
P1 O12 1.5809(15) . ?
P1 O13 1.5865(16) . ?
O12 C12 1.446(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O13 C13 1.441(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
C7 H7 O13 0.95 2.63 3.490(2) 151.4 12_554
C12 H12C O11 0.98 2.49 3.424(3) 159.4 10_565
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
C3 C1 C2 C3 -1.1(3) 2_665 . . . ?
C1 C2 C3 C1 14.3(3) . . . 2_665 ?
C1 C2 C3 C4 -152.7(2) . . . . ?
C2 C3 C4 C5 72.2(2) . . . . ?
C1 C3 C4 C5 -94.3(2) 2_665 . . . ?
C3 C4 C5 C6 16.0(2) . . . . ?
C4 C5 C6 C7 -96.2(2) . . . . ?
C4 C5 C6 C8 72.6(3) . . . 2_665 ?
C8 C6 C7 C8 -15.1(3) 2_665 . . . ?
C5 C6 C7 C8 154.39(19) . . . . ?
C6 C7 C8 C6 -2.8(3) . . . 2_665 ?
C6 C7 C8 P1 -178.56(16) . . . . ?
C7 C8 P1 O11 114.30(17) . . . . ?
C6 C8 P1 O11 -61.42(19) 2_665 . . . ?
C7 C8 P1 O12 -12.96(18) . . . . ?
C6 C8 P1 O12 171.32(17) 2_665 . . . ?
C7 C8 P1 O13 -123.76(17) . . . . ?
C6 C8 P1 O13 60.52(18) 2_665 . . . ?
O11 P1 O12 C12 44.08(19) . . . . ?
O13 P1 O12 C12 -77.05(17) . . . . ?
C8 P1 O12 C12 172.93(16) . . . . ?
O11 P1 O13 C13 -175.95(16) . . . . ?
O12 P1 O13 C13 -50.81(17) . . . . ?
C8 P1 O13 C13 56.55(18) . . . . ?
