Host-guest system of a phosphorylated macrocycle assisting structure determination of oily molecules in single-crystal form.
Jiao, Jianmin; Li, Heng; Xie, Wang; Zhao, Yue; Lin, Chen; Jiang, Juli; Wang, Leyong; Chemical science 14 (2023) 11402–11409; doi:10.1039/d3sc02995f

data_1569953
_publ_section_title
;
 Host-guest system of a phosphorylated macrocycle assisting structure
 determination of oily molecules in single-crystal form.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              11402
_journal_page_last               11409
_journal_paper_doi               10.1039/d3sc02995f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C45 H39 O9 P3, C8 H16 O4'
_chemical_formula_sum            'C53 H55 O13 P3'
_chemical_formula_weight         992.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-03-27 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.957(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.3052(12)
_cell_length_b                   9.0255(10)
_cell_length_c                   17.3209(18)
_cell_measurement_reflns_used    6555
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      25.898
_cell_measurement_theta_min      2.632
_cell_volume                     2343.9(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2030
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            104871
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.351
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5515
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1752 before and 0.1172 after correction.
The Ratio of minimum to maximum transmission is 0.7397.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       plate
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         5706
_refine_ls_number_restraints     545
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.0848
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0898P)^2^+3.6215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2114
_refine_ls_wR_factor_ref         0.2581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3231
_reflns_number_total             5706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02995f2.cif
_cod_data_source_block           1a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1569950--1569976.cif.'
_cod_database_code               1569953
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-C005
 1.55 with sigma of 0.02
 C9-C14 = C12-C10 = C9_$1-C14_$1 = C12_$1-C10_$1
 1.5 with sigma of 0.02
 C9A-C14A = C12A_$1-C10A_$1 = C9A_$1-C14A_$1 = C12A-C10A
 1.5 with sigma of 0.02
 C12A-C10A \\sim C9A-C14A \\sim C12A_$1-C10A_$1 \\sim C9A_$1-C14A_$1
 with sigma of 0.02
 P002-O00I \\sim P002-O00J \\sim P003-O00K \\sim P003-O00H \\sim P001-O00L
\\sim P001-O00B
 with sigma of 0.02
 C10A-O5A \\sim C14A_$1-O6A_$1 \\sim C10A_$1-O5A_$1 \\sim C14A-O6A
 with sigma of 0.02
 C2-C005 \\sim C7-C007 \\sim C6-C006 \\sim C3-C008 \\sim C11-C004 \\sim C8-C009
 with sigma of 0.02
 O5A_$1-C14A \\sim O5A_$1-C12A_$1 \\sim O6A_$1-C9A_$1 \\sim O6A_$1-C10A_$1
\\sim O5A-C14A_$1 ~
 O5A-C12A \\sim O6A-C10A \\sim O6A-C9A
 with sigma of 0.02
 O6-C9 \\sim O6-C10 \\sim O5-C12 \\sim O5-C14_$1 \\sim O6_$1-C9_$1 \\sim
O6_$1-C10_$1 \\sim O5_$1-
 C12_$1 \\sim O5_$1-C14
 with sigma of 0.02
 O00I-C011 \\sim O00J-C00X \\sim O00B-C00U \\sim O00L-C012 \\sim O00H-C00W
\\sim O00K-C017
 with sigma of 0.02
 C12A-C14A_$1 \\sim C9A_$1-C10A_$1 \\sim C12A_$1-C14A \\sim C9A-C10A
 with sigma of 0.02
 C14-C12_$1 \\sim C10_$1-C9_$1 \\sim C14_$1-C12 \\sim C10-C9
 with sigma of 0.02
 C9-O5_$1 \\sim C12_$1-O6_$1 \\sim C9_$1-O5 \\sim C12-O6
 with sigma of 0.02
 P003-C00G \\sim P002-C00C \\sim P001-C00F
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C14A \\sim C14A \\sim C9A \\sim O5A \\sim O6A \\sim C12A \\sim C10A \\sim C10A
\\sim C12A \\sim O6A \\sim O5A \\sim C9A: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
O5 \\sim C9 \\sim O6 \\sim C14 \\sim C10 \\sim O5 \\sim C12 \\sim C12 \\sim C10
\\sim C14 \\sim O6 \\sim C9: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
Uanis(C01B) \\sim Ueq, Uanis(P001) \\sim Ueq, Uanis(O00B) \\sim Ueq,
Uanis(C00F) \\sim Ueq, Uanis(O00L) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C00U)
\\sim Ueq, Uanis(C019) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C012) \\sim Ueq,
Uanis(C006) \\sim Ueq, Uanis(C00S) \\sim Ueq, Uanis(C01D) \\sim Ueq,
Uanis(C00E) \\sim Ueq, Uanis(C00Z) \\sim Ueq, Uanis(C007) \\sim Ueq,
Uanis(C008) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C00V) \\sim Ueq, Uanis(C010)
\\sim Ueq, Uanis(C00T) \\sim Ueq, Uanis(C00R) \\sim Ueq, Uanis(C005) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(C00X) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C015)
\\sim Ueq, Uanis(C00W) \\sim Ueq, Uanis(C00Y) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(O00J) \\sim Ueq, Uanis(C00Q) \\sim Ueq, Uanis(O00H) \\sim Ueq,
Uanis(C014) \\sim Ueq, Uanis(P002) \\sim Ueq, Uanis(C011) \\sim Ueq,
Uanis(P003) \\sim Ueq, Uanis(C017) \\sim Ueq, Uanis(C00C) \\sim Ueq,
Uanis(O00I) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C004) \\sim Ueq, Uanis(C00G)
\\sim Ueq, Uanis(O00K) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C009) \\sim Ueq,
Uanis(C4) \\sim Ueq, Uanis(C018) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C01A)
\\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C00A) \\sim Ueq,
Uanis(C01C) \\sim Ueq, Uanis(C00D) \\sim Ueq, Uanis(C016) \\sim Ueq,
Uanis(C013) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(O6A)=Sof(C10A)=
 Sof(H10C)=Sof(H10D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(O5A)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(O5)=Sof(C12)=
 Sof(H12A)=Sof(H12B)=Sof(O6)=Sof(C14)=Sof(H14A)=Sof(H14B)=FVAR(1)
 Fixed Sof: P001(0.5) P002(0.5) P003(0.5) C009(0.5) C004(0.5) C011(0.5)
 C00Q(0.5) C014(0.5) C017(0.5) C00A(0.5) H00A(0.5) C016(0.5) H016(0.5)
 C01C(0.5) H01C(0.5) C018(0.5) H018(0.5) C00C(0.5) C4(0.5) H4(0.5) O00B(0.5)
 C00D(0.5) H00D(0.5) C013(0.5) H013(0.5) C01B(0.5) H01B(0.5) C01A(0.5)
 H01A(0.5) C00G(0.5) C5(0.5) H5(0.5) C00E(0.5) H00E(0.5) C00T(0.5) H00T(0.5)
 C01D(0.5) H01D(0.5) C019(0.5) H019(0.5) C00F(0.5) C1(0.5) H1(0.5) O00H(0.5)
 O00I(0.5) O00J(0.5) O00K(0.5) O00L(0.5) C00R(0.5) C00Z(0.5) C012(0.5)
 C007(0.5) C005(0.5) C00W(0.5) C00X(0.5) C008(0.5) C006(0.5) C00U(0.5)
 C00S(0.5) C00V(0.5) C00Y(0.5) H00B(0.5) H00C(0.5) C010(0.5) H01E(0.5)
 H01F(0.5) C015(0.5) H01G(0.5) H01H(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
 C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5) C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C3(0.5)
 H3A(0.5) H3B(0.5) H3C(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5) C8(0.5) H8A(0.5)
 H8B(0.5) H8C(0.5) O2(0.5) O1(0.5) O3(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C00Y(H00B,H00C), C010(H01E,H01F), C015(H01G,H01H), C9(H9A,H9B), C10(H10A,
 H10B), C12(H12A,H12B), C14(H14A,H14B), C14A(H14C,H14D), C9A(H9AA,H9AB),
 C10A(H10C,H10D), C12A(H12C,H12D)
5.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C016(H016), C01C(H01C), C018(H018), C4(H4), C00D(H00D),
 C013(H013), C01B(H01B), C01A(H01A), C5(H5), C00E(H00E), C00T(H00T), C01D(H01D),
  C019(H019), C1(H1)
5.c Fitted hexagon refined as free rotating group:
 C009(C004,C011,C00Q,C014,C017), C00A(C016,C01C,C018,C00C,C4), C00D(C013,C01B,
 C01A,C00G,C5), C00E(C00T,C01D,C019,C00F,C1), C00R(C00Z,C012,C007,C005,C00W),
 C00X(C008,C006,C00U,C00S,C00V)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C6(H6A,H6B,H6C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C),
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              97904
_olex2_submission_special_instructions 'No special instructions were received'