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#$Date: 2022-11-17 01:16:44 +0200 (Thu, 17 Nov 2022) $
#$Revision: 279331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/79/1567979.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_1567979
loop_
_publ_author_name
'Zhu, Yun'
'Stollenz, Michael'
'Zarcone, Samuel R.'
'Kharel, Sugam'
'Joshi, Hemant'
'Bhuvanesh, Nattamai'
'Reibenspies, Joseph H.'
'Gladysz, John A.'
_publ_section_title
;
 Syntheses, homeomorphic and configurational isomerizations, and
 structures of macrocyclic aliphatic dibridgehead diphosphines; molecules
 that turn themselves inside out
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04724A
_journal_year                    2022
_chemical_formula_moiety         'C42 H84 P2'
_chemical_formula_sum            'C42 H84 P2'
_chemical_formula_weight         651.03
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-14 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   9.1903(19)
_cell_length_b                   9.1903(19)
_cell_length_c                   89.58(2)
_cell_measurement_reflns_used    518
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      54.49
_cell_measurement_theta_min      2.96
_cell_volume                     6552(2)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.15
_diffrn_detector                 'MWPC area detector'
_diffrn_detector_area_resol_mean 4
_diffrn_detector_type            'Bruker GADDS MWPC detector'
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker GADDS MWPC area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_collimation    0.5mm
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2152
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       100
_diffrn_reflns_limit_l_min       -99
_diffrn_reflns_number            14394
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        59.996
_diffrn_reflns_theta_max         59.996
_diffrn_reflns_theta_min         2.960
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40.0
_diffrn_source_power             1.6
_diffrn_source_target            Cu
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.061
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.6007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0982 before and 0.0566 after correction. The Ratio of minimum to maximum transmission is 0.7989. The λ/2 correction factor is 0.0000.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.990
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2196
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         1047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0400
_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)+(0.0181P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0707
_reflns_Friedel_coverage         0.000
_reflns_number_gt                717
_reflns_number_total             1047
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04724a3.cif
_cod_data_source_block           jgmsa
_cod_original_cell_volume        6552(3)
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               1567979
_shelx_shelxl_version_number     2019/2
_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_max   0.989
_shelx_estimated_absorpt_t_min   0.901
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'-x, -x+y, -z+1/2'
'x-y, -y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'x, x-y, z-1/2'
'-x+y, y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
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
P1 P -0.333333 0.333333 0.01106(2) 0.0294(3) Uani 1 3 d S T P . .
C1 C -0.13619(19) 0.3937(2) 0.02096(2) 0.0298(5) Uani 1 1 d . . . . .
H1A H -0.058759 0.515260 0.019369 0.036 Uiso 1 1 calc R U . . .
H1B H -0.160520 0.376405 0.031790 0.036 Uiso 1 1 calc R U . . .
C2 C -0.0464(2) 0.2996(2) 0.01641(2) 0.0320(5) Uani 1 1 d . . . . .
H2A H -0.019688 0.318348 0.005631 0.038 Uiso 1 1 calc R U . . .
H2B H -0.123672 0.177798 0.017893 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1154(2) 0.3514(2) 0.02503(2) 0.0331(5) Uani 1 1 d . . . . .
H3A H 0.176582 0.301518 0.020078 0.040 Uiso 1 1 calc R U . . .
H3B H 0.187273 0.475070 0.024481 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0895(2) 0.2990(2) 0.04138(2) 0.0326(5) Uani 1 1 d . . . . .
H4A H 0.024594 0.345156 0.046259 0.039 Uiso 1 1 calc R U . . .
H4B H 0.021577 0.174941 0.041939 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2507(2) 0.3565(2) 0.04996(2) 0.0337(5) Uani 1 1 d . . . . .
H5A H 0.317842 0.480713 0.049572 0.040 Uiso 1 1 calc R U . . .
H5B H 0.316563 0.311883 0.045009 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2231(2) 0.3010(2) 0.06619(2) 0.0351(5) Uani 1 1 d . . . . .
H6A H 0.159819 0.176723 0.066526 0.042 Uiso 1 1 calc R U . . .
H6B H 0.152588 0.341332 0.070976 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3834(2) 0.3637(2) 0.07522(2) 0.0406(5) Uani 1 1 d . . . . .
H7A H 0.445395 0.488076 0.075134 0.049 Uiso 1 1 calc R U . . .
H7B H 0.455234 0.325661 0.070337 0.049 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'
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
C1 P1 C1 98.63(7) . 3_455 ?
C1 P1 C1 98.62(7) 3_455 2_565 ?
C1 P1 C1 98.63(7) . 2_565 ?
P1 C1 H1A 108.4 . . ?
P1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C2 C1 P1 115.66(11) . . ?
C2 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C1 C2 C3 114.13(13) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.47(14) . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.05(13) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.53(13) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C5 C6 C7 114.49(14) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C6 C7 C7 113.68(13) . 18_554 ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C7 C7 H7A 108.8 18_554 . ?
C7 C7 H7B 108.8 18_554 . ?
H7A C7 H7B 107.7 . . ?
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
P1 C1 1.8363(16) . ?
P1 C1 1.8364(16) 2_565 ?
P1 C1 1.8364(16) 3_455 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5193(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.525(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.523(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.510(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.520(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.519(2) . ?
C7 C7 1.532(3) 18_554 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
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
P1 C1 C2 C3 -179.17(11) . . . . ?
C1 P1 C1 C2 177.32(11) 2_565 . . . ?
C1 P1 C1 C2 77.16(16) 3_455 . . . ?
C1 C2 C3 C4 69.47(19) . . . . ?
C2 C3 C4 C5 -177.79(13) . . . . ?
C3 C4 C5 C6 -179.06(13) . . . . ?
C4 C5 C6 C7 -177.54(14) . . . . ?
C5 C6 C7 C7 -178.63(17) . . . 18_554 ?
