# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb1390_hy_compound_3b
_database_code_depnum_ccdc_archive 'CCDC 2103359'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
tetramethyl 1,4(1,4)-dibenzenacyclohexaphane-1²,1⁵-diylbis(phosphonate)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 O6 P2'
_chemical_formula_sum            'C20 H26 O6 P2'
_chemical_formula_weight         424.35

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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.
;

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'

_cell_length_a                   21.1103(13)
_cell_length_b                   21.6232(14)
_cell_length_c                   8.7121(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3976.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      72.2

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.293
_shelx_estimated_absorpt_T_min   0.657
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7534
_exptl_absorpt_correction_T_max  0.8894
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 12+1 runs, 2462 frames, 6/24 sec./frame
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16792
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.858
_diffrn_reflns_theta_max         72.199
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1959
_reflns_number_gt                1954
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+3.5595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_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)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1959
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_ref         0.0599
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038

