Structure and absolute configuration of liquid molecules based on adamantane derivative cocrystallization
Ou, Guang-Chuan; Chen, Hai-Yang; Wang, Qiong; Zhou, Qiang; Zeng, Fei; RSC Advances 12 (2022) 6459–6462; doi:10.1039/D1RA09284G

data_7244489
_publ_section_title
;
 Structure and absolute configuration of liquid molecules based on
 adamantane derivative cocrystallization
;
_journal_issue                   11
_journal_name_full               'RSC Advances'
_journal_page_first              6459
_journal_page_last               6462
_journal_paper_doi               10.1039/D1RA09284G
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '2(C50 H64 O8), C8 H9 Cl O, C8 H7 Cl O'
_chemical_formula_sum            'C116 H144 Cl2 O18'
_chemical_formula_weight         1897.20
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-12-06 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                66.263(3)
_cell_angle_beta                 80.241(3)
_cell_angle_gamma                63.042(4)
_cell_formula_units_Z            1
_cell_length_a                   14.4591(7)
_cell_length_b                   14.5057(5)
_cell_length_c                   15.3163(5)
_cell_measurement_reflns_used    26775
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.8240
_cell_measurement_theta_min      3.6360
_cell_volume                     2620.8(2)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.99(10)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            41735
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.446
_diffrn_reflns_theta_min         3.152
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.61339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             1018
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.150
_refine_diff_density_min         -1.058
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 6230 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.124(14)
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1215
_refine_ls_number_reflns         18813
_refine_ls_number_restraints     2747
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0963
_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/[\s^2^(Fo^2^)+(0.1291P)^2^+5.6299P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2531
_refine_ls_wR_factor_ref         0.2607
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.860
_reflns_Friedel_fraction_max     0.805
_reflns_number_gt                16746
_reflns_number_total             18813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra09284g2.cif
_cod_data_source_block           59-2
_cod_database_code               7244489
_shelx_shelxl_version_number     2018/3
_exptl_absorpt_special_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_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, All O(H) groups
2. Restrained distances
 Cl2-C116
 1.75 with sigma of 0.01
 C115-C109 = C116-C115
 1.5 with sigma of 0.02
 C110-C109 = C114-C109 = C114-C113 = C113-C112 = C112-C111 = C111-C110
 1.4 with sigma of 0.01
 C102-C105 = C109-C112
 2.75 with sigma of 0.02
 O18A-C116
 2.5 with sigma of 0.02
 O18A-C115
 1.45 with sigma of 0.02
 C1B-C109
 1.5 with sigma of 0.01
 C116-C115
 1.5 with sigma of 0.02
 O18B-C116
 2.3 with sigma of 0.02
 O18A-C115 = O18B-C1B
 1.45 with sigma of 0.02
 O18B-C1B
 1.45 with sigma of 0.01
 C1B-C116
 1.5 with sigma of 0.01
 C115-C110
 2.5 with sigma of 0.02
 C111-C114
 2.75 with sigma of 0.02
 C110-C113
 2.75 with sigma of 0.02
 C111-C113
 2.5 with sigma of 0.02
 C110-C112
 2.5 with sigma of 0.02
 C114-C112
 2.5 with sigma of 0.02
 C1A-C107 = C108-C107
 1.5 with sigma of 0.02
 Cl1A-C108 = Cl1B-C1A
 1.7 with sigma of 0.02
 C1B-C110
 2.5 with sigma of 0.02
 C115-C114
 2.5 with sigma of 0.02
 C1B-C116 = C116-C115
 1.5 with sigma of 0.02
3. Restrained planarity
 C109, C110, C111, C112, C113, C114
 with sigma of 0.1
4. Rigid bond restraints
 Cl2, C116
 with sigma for 1-2 distances of 0.0025 and sigma for 1-3 distances of 0.00125
5. Uiso/Uaniso restraints and constraints
C9 \\sim C77 \\sim C96 \\sim C71 \\sim C85 \\sim C81 \\sim C84 \\sim C13 \\sim
C33 \\sim C65 \\sim C53 \\sim C36 \\sim C4 \\sim C55 \\sim C86 \\sim C76 \\sim
C23 \\sim C61 \\sim C2 \\sim C82 \\sim C7 \\sim C12 \\sim C31 \\sim C3 \\sim
C35 \\sim C51 \\sim C16 \\sim C91 \\sim C10 \\sim C34 \\sim C54 \\sim C64 \\sim
C57 \\sim C22 \\sim C6 \\sim C27 \\sim C72 \\sim C73 \\sim C1 \\sim C11 \\sim
C43 \\sim C101 \\sim C37 \\sim C39 \\sim C44 \\sim C58 \\sim C20 \\sim C21
\\sim C93 \\sim C59 \\sim C46 \\sim C52 \\sim C94 \\sim C38 \\sim C107 \\sim
C15 \\sim C26 \\sim C89 \\sim C45 \\sim C41 \\sim C69 \\sim C56 \\sim C32 \\sim
C97 \\sim C66 \\sim C5 \\sim C62 \\sim C79 \\sim C102 \\sim C74 \\sim C17 \\sim
C42 \\sim C83 \\sim C14 \\sim C24 \\sim C40 \\sim C95 \\sim C18 \\sim C99 \\sim
C8 \\sim C106 \\sim C75 \\sim C105 \\sim C92 \\sim C60 \\sim C19 \\sim C68
\\sim C48 \\sim C30 \\sim C100 \\sim C29 \\sim C63 \\sim C67 \\sim C80 \\sim
C87 \\sim C90 \\sim C104 \\sim C70 \\sim C25 \\sim C28 \\sim C78 \\sim C47
\\sim C88 \\sim C98 \\sim C108 \\sim C103 \\sim C49 \\sim C109 \\sim C110 \\sim
C116 \\sim C115 \\sim C113 \\sim C114 \\sim C112 \\sim C111 \\sim C50 \\sim C1A
\\sim C1B: within 3.8A with sigma of 0.005 and sigma for terminal atoms of 0.01
within 3.8A
Uanis(C115) = Uanis(C116) = Uanis(C110) = Uanis(C109) = Uanis(C111) =
Uanis(C114) = Uanis(C112) = Uanis(C113)
Uanis(C1B) = Uanis(C115) = Uanis(C116)
Uanis(Cl1A) = Uanis(Cl1B)
Uanis(C108) = Uanis(C1A) = Uanis(C107)
6. Others
 Sof(H10F)=Sof(C108)=Sof(H10G)=Sof(H10H)=Sof(Cl1A)=1-FVAR(1)
 Sof(H107)=Sof(Cl1B)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=FVAR(1)
 Sof(O18B)=Sof(H18D)=1-FVAR(2)
 Sof(O18A)=Sof(H18C)=FVAR(2)
 Sof(C1B)=Sof(H1B)=1-FVAR(3)
 Sof(C115)=Sof(H115)=FVAR(3)
7.a Riding coordinates:
 O17(H17), O18A(H18C), O18B(H18D)
7.b Ternary CH refined with riding coordinates:
 C107(H10F), C107(H107), C115(H115), C1B(H1B)
7.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C77(H77A,H77B), C65(H65A,H65B), C4(H4A,H4B), C2(H2A,H2B),
 C16(H16A,H16B), C10(H10D,H10E), C54(H54A,H54B), C6(H6A,H6B), C27(H27A,H27B),
 C37(H37A,H37B), C39(H39A,H39B), C58(H58A,H58B), C59(H59A,H59B), C52(H52A,H52B),
  C89(H89A,H89B), C69(H69A,H69B), C56(H56A,H56B), C97(H97A,H97B), C79(H79A,
 H79B), C18(H18A,H18B), C99(H99A,H99B), C60(H60A,H60B), C29(H29A,H29B),
 C67(H67A,H67B), C87(H87A,H87B), C47(H47A,H47B), C108(H10G,H10H), C49(H49A,
 H49B), C1A(H1AA,H1AB)
7.d Aromatic/amide H refined with riding coordinates:
 C85(H85), C13(H13), C33(H33), C36(H36), C23(H23), C82(H82), C12(H12),
 C35(H35), C22(H22), C72(H72), C73(H73), C43(H43), C93(H93), C46(H46), C15(H15),
  C45(H45), C66(H66), C102(H102), C83(H83), C95(H95), C8(H8), C106(H106),
 C75(H75), C105(H105), C92(H92), C63(H63), C104(H104), C25(H25), C103(H103),
 C110(H110), C113(H113), C114(H114), C112(H112), C111(H111)
7.e Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C17(H17A,H17B,H17C), C40(H40A,H40B,H40C), C19(H19A,H19B,
 H19C), C68(H68A,H68B,H68C), C48(H48A,H48B,H48C), C30(H30A,H30B,H30C),
 C100(H10A,H10B,H10C), C80(H80A,H80B,H80C), C90(H90A,H90B,H90C), C70(H70A,H70B,
 H70C), C28(H28A,H28B,H28C), C78(H78A,H78B,H78C), C88(H88A,H88B,H88C), C98(H98A,
 H98B,H98C), C50(H50A,H50B,H50C)
;
_shelx_res_checksum              90606
_olex2_submission_special_instructions 'No special instructions were received'