#------------------------------------------------------------------------------
#$Date: 2020-12-02 07:37:30 +0200 (Wed, 02 Dec 2020) $
#$Revision: 259461 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157788.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_7157788
loop_
_publ_author_name
'Gadigennavar, Savita'
'Ranganathan, Madhav'
'Sankararaman, Sethuraman'
_publ_section_title
;
 Which isomer is it, 1,2,5,6- or 1,4,5,8-tetrasubstituted
 cycloocta-1,3,5,7-tetraene? Synthesis of symmetrically tetrasubstituted
 cycloocta-1,3,5,7-tetraene derivatives
;
_journal_issue                   45
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              9284
_journal_page_last               9291
_journal_paper_doi               10.1039/D0OB01871F
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H36 O12 P4, H2 O'
_chemical_formula_sum            'C20 H38 O13 P4'
_chemical_formula_weight         610.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-08-15 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 127.7290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6392(6)
_cell_length_b                   18.8539(9)
_cell_length_c                   12.4008(7)
_cell_measurement_reflns_used    8457
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.82
_cell_measurement_theta_min      2.99
_cell_volume                     2892.0(2)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26490
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.160
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2557
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0411
_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)+(0.0455P)²+5.3718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1937
_reflns_number_total             2557
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01871f2.cif
_cod_data_source_block           PHO
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7157788
_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   0.939
_shelx_estimated_absorpt_t_max   0.954
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_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 0.8137(4) 0.5101(2) 0.5296(5) 0.0915(13) Uani 1 1 d . . . . .
H1A H 0.8198 0.5084 0.4572 0.137 Uiso 1 1 calc R U . . .
H1B H 0.8826 0.4995 0.6146 0.137 Uiso 1 1 calc R U . . .
H1C H 0.7614 0.4759 0.5128 0.137 Uiso 1 1 calc R U . . .
C3 C 0.6749(2) 0.67566(15) 0.5619(3) 0.0430(7) Uani 1 1 d . . . . .
H3A H 0.6519 0.6893 0.6160 0.052 Uiso 1 1 calc R U . . .
H3B H 0.7164 0.7148 0.5646 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5751(2) 0.66601(13) 0.4159(2) 0.0331(6) Uani 1 1 d . . . . .
C5 C 0.50541(19) 0.60361(13) 0.3852(2) 0.0313(5) Uani 1 1 d . . . . .
C6 C 0.4673(2) 0.59381(14) 0.4715(3) 0.0366(6) Uani 1 1 d . . . . .
H6A H 0.5295 0.5814 0.5632 0.044 Uiso 1 1 calc R U . . .
H6B H 0.4181 0.5538 0.4353 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3103(4) 0.6652(2) 0.6040(4) 0.0814(12) Uani 1 1 d . . . . .
H7A H 0.2846 0.6312 0.6358 0.122 Uiso 1 1 calc R U . . .
H7B H 0.3663 0.6935 0.6793 0.122 Uiso 1 1 calc R U . . .
H7C H 0.2517 0.6953 0.5369 0.122 Uiso 1 1 calc R U . . .
C8 C 0.2230(3) 0.6442(2) 0.2351(4) 0.0720(10) Uani 1 1 d . . . . .
H8A H 0.1716 0.6694 0.1519 0.108 Uiso 1 1 calc R U . . .
H8B H 0.2555 0.6071 0.2184 0.108 Uiso 1 1 calc R U . . .
H8C H 0.1868 0.6240 0.2684 0.108 Uiso 1 1 calc R U . . .
C9 C 0.4811(2) 0.55616(13) 0.2917(2) 0.0347(6) Uani 1 1 d . . . . .
H9 H 0.4357 0.5192 0.2773 0.042 Uiso 1 1 calc R U . . .
C10 C 0.5485(2) 0.71407(13) 0.3213(3) 0.0362(6) Uani 1 1 d . . . . .
H10 H 0.5964 0.7515 0.3485 0.043 Uiso 1 1 calc R U . . .
O1 O 0.7809(2) 0.57798(15) 0.5360(3) 0.0849(9) Uani 1 1 d . . . . .
C2 C 0.9432(19) 0.6276(14) 0.8843(14) 0.076(5) Uani 0.49(2) 1 d D U P A 1
H2A H 1.0163 0.6408 0.9241 0.115 Uiso 0.49(2) 1 calc R U P A 1
H2B H 0.9110 0.6633 0.9043 0.115 Uiso 0.49(2) 1 calc R U P A 1
H2C H 0.9430 0.5830 0.9215 0.115 Uiso 0.49(2) 1 calc R U P A 1
O2 O 0.8848(5) 0.6214(6) 0.7450(6) 0.053(2) Uani 0.49(2) 1 d D U P A 1
C2' C 0.9381(15) 0.6142(14) 0.8931(13) 0.075(5) Uani 0.51(2) 1 d D U P A 2
H2'1 H 0.9881 0.6490 0.9584 0.113 Uiso 0.51(2) 1 calc R U P A 2
H2'2 H 0.9053 0.5897 0.9273 0.113 Uiso 0.51(2) 1 calc R U P A 2
H2'3 H 0.9760 0.5808 0.8778 0.113 Uiso 0.51(2) 1 calc R U P A 2
O2' O 0.8587(7) 0.6476(5) 0.7714(8) 0.065(3) Uani 0.51(2) 1 d D U P A 2
O3 O 0.72605(16) 0.54451(11) 0.6856(2) 0.0527(5) Uani 1 1 d . . . . .
O4 O 0.30536(17) 0.69239(11) 0.3350(2) 0.0558(6) Uani 1 1 d . . . . .
O5 O 0.47011(17) 0.72878(10) 0.5599(2) 0.0529(5) Uani 1 1 d . . . . .
O6 O 0.35195(19) 0.62938(12) 0.5455(2) 0.0618(6) Uani 1 1 d . . . . .
P2 P 0.40144(6) 0.66771(4) 0.48233(7) 0.0408(2) Uani 1 1 d . . . . .
P1 P 0.76237(6) 0.60082(4) 0.64137(8) 0.0494(2) Uani 1 1 d D . . . .
O7 O 0.5000 0.8336(2) 0.7500 0.0927(14) Uani 1 2 d S T P . .
H7 H 0.516(6) 0.808(3) 0.818(6) 0.17(3) Uiso 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 P1 116.54(19) . . ?
C4 C3 H3A 108.2 . . ?
P1 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
P1 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
C10 C4 C5 121.9(2) . . ?
C10 C4 C3 120.7(2) . . ?
C5 C4 C3 117.4(2) . . ?
C9 C5 C4 122.2(2) . . ?
C9 C5 C6 120.5(2) . . ?
C4 C5 C6 117.2(2) . . ?
C5 C6 P2 116.77(18) . . ?
C5 C6 H6A 108.1 . . ?
P2 C6 H6A 108.1 . . ?
C5 C6 H6B 108.1 . . ?
P2 C6 H6B 108.1 . . ?
H6A C6 H6B 107.3 . . ?
O6 C7 H7A 109.5 . . ?
O6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 C9 126.3(2) . 2_655 ?
C5 C9 H9 116.8 . . ?
C9 C9 H9 116.8 2_655 . ?
C4 C10 C10 126.7(2) . 2_655 ?
C4 C10 H10 116.6 . . ?
C10 C10 H10 116.6 2_655 . ?
C1 O1 P1 124.2(2) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C2 O2 P1 126.0(13) . . ?
O2' C2' H2'1 109.5 . . ?
O2' C2' H2'2 109.5 . . ?
H2'1 C2' H2'2 109.5 . . ?
O2' C2' H2'3 109.5 . . ?
H2'1 C2' H2'3 109.5 . . ?
H2'2 C2' H2'3 109.5 . . ?
C2' O2' P1 120.0(13) . . ?
C8 O4 P2 122.1(2) . . ?
C7 O6 P2 124.0(2) . . ?
O5 P2 O4 109.11(12) . . ?
O5 P2 O6 114.91(12) . . ?
O4 P2 O6 107.69(13) . . ?
O5 P2 C6 115.98(13) . . ?
O4 P2 C6 109.27(12) . . ?
O6 P2 C6 99.28(12) . . ?
O3 P1 O1 115.30(15) . . ?
O3 P1 O2 115.7(2) . . ?
O1 P1 O2 89.7(5) . . ?
O3 P1 O2' 110.9(3) . . ?
O1 P1 O2' 116.3(6) . . ?
O3 P1 C3 116.07(13) . . ?
O1 P1 C3 103.17(13) . . ?
O2 P1 C3 113.3(5) . . ?
O2' P1 C3 92.9(4) . . ?
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 O1 1.399(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C4 1.513(4) . ?
C3 P1 1.784(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C10 1.332(3) . ?
C4 C5 1.486(3) . ?
C5 C9 1.323(3) . ?
C5 C6 1.521(3) . ?
C6 P2 1.786(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.409(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O4 1.437(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C9 1.474(5) 2_655 ?
C9 H9 0.9300 . ?
C10 C10 1.464(5) 2_655 ?
C10 H10 0.9300 . ?
O1 P1 1.562(3) . ?
C2 O2 1.379(13) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
O2 P1 1.568(5) . ?
C2' O2' 1.386(12) . ?
C2' H2'1 0.9600 . ?
C2' H2'2 0.9600 . ?
C2' H2'3 0.9600 . ?
O2' P1 1.635(7) . ?
O3 P1 1.460(2) . ?
O4 P2 1.566(2) . ?
O5 P2 1.463(2) . ?
O6 P2 1.574(2) . ?
O7 H7 0.86(5) . ?
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
C1 H1C O6 0.96 2.46 3.397(5) 166.7 5_666
C3 H3A O5 0.97 2.59 3.341(4) 134.6 .
C6 H6A O3 0.97 2.55 3.337(3) 137.8 .
C6 H6B O3 0.97 2.57 3.540(3) 173.6 5_666
O7 H7 O5 0.86(5) 2.05(5) 2.887(4) 165(6) 2_656
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 C3 C4 C10 -132.2(2) . . . . ?
P1 C3 C4 C5 51.4(3) . . . . ?
C10 C4 C5 C9 59.9(4) . . . . ?
C3 C4 C5 C9 -123.8(3) . . . . ?
C10 C4 C5 C6 -123.4(3) . . . . ?
C3 C4 C5 C6 53.0(3) . . . . ?
C9 C5 C6 P2 -130.1(2) . . . . ?
C4 C5 C6 P2 53.1(3) . . . . ?
C4 C5 C9 C9 1.4(4) . . . 2_655 ?
C6 C5 C9 C9 -175.3(3) . . . 2_655 ?
C5 C4 C10 C10 0.1(4) . . . 2_655 ?
C3 C4 C10 C10 -176.1(3) . . . 2_655 ?
C8 O4 P2 O5 -179.1(2) . . . . ?
C8 O4 P2 O6 -53.7(3) . . . . ?
C8 O4 P2 C6 53.2(3) . . . . ?
C7 O6 P2 O5 41.1(3) . . . . ?
C7 O6 P2 O4 -80.7(3) . . . . ?
C7 O6 P2 C6 165.5(3) . . . . ?
C5 C6 P2 O5 -69.8(2) . . . . ?
C5 C6 P2 O4 54.0(2) . . . . ?
C5 C6 P2 O6 166.49(19) . . . . ?
C1 O1 P1 O3 -30.6(4) . . . . ?
C1 O1 P1 O2 87.9(5) . . . . ?
C1 O1 P1 O2' 101.7(5) . . . . ?
C1 O1 P1 C3 -158.2(3) . . . . ?
C2 O2 P1 O3 -41(2) . . . . ?
C2 O2 P1 O1 -158.9(18) . . . . ?
C2 O2 P1 C3 96.8(17) . . . . ?
C2' O2' P1 O3 39.8(18) . . . . ?
C2' O2' P1 O1 -94.6(16) . . . . ?
C2' O2' P1 C3 159.2(16) . . . . ?
C4 C3 P1 O3 -76.5(2) . . . . ?
C4 C3 P1 O1 50.6(2) . . . . ?
C4 C3 P1 O2 146.1(4) . . . . ?
C4 C3 P1 O2' 168.5(6) . . . . ?
