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_7244493
_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 unknown
_chemical_formula_moiety         'C50 H64 O8, C9 H13 N'
_chemical_formula_sum            'C59 H77 N O8'
_chemical_formula_weight         928.21
_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   geom
_audit_creation_date             2021-10-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2021-12-06 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                66.8561(18)
_cell_angle_beta                 80.7799(14)
_cell_angle_gamma                62.3050(16)
_cell_formula_units_Z            2
_cell_length_a                   14.4791(2)
_cell_length_b                   14.6694(3)
_cell_length_c                   15.3429(3)
_cell_measurement_reflns_used    29241
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7950
_cell_measurement_theta_min      3.4100
_cell_volume                     2652.25(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -117.00  -2.00   1.00    1.00    --  -41.14 -19.00 -60.00  115
  2  \w   -115.00 -17.00   1.00    1.00    --  -41.14 -38.00-150.00   98
  3  \w    -74.00  12.00   1.00    1.00    --  -41.14  77.00 120.00   86
  4  \w   -112.00 -13.00   1.00    1.00    --  -41.14 -57.00 120.00   99
  5  \w    -68.00  25.00   1.00    1.00    --  -41.14  57.00 -90.00   93
  6  \w     24.00  95.00   1.00    1.00    --   41.14-125.00  30.00   71
  7  \w      7.00  32.00   1.00    1.00    --   42.00  87.00-139.65   25
  8  \w     11.00  36.00   1.00    1.00    --   46.00  84.00 -28.84   25
  9  \w     12.00  37.00   1.00    1.00    --   46.00  83.00 112.38   25
 10  \w     16.00  41.00   1.00    1.00    --   50.00  81.00-115.55   25
 11  \w     16.00  41.00   1.00    1.00    --   50.00  81.00  23.66   25
 12  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 156.93   25
 13  \w     30.00  56.00   1.00    1.00    --   62.00  77.00 -88.78   26
 14  \w     29.00  55.00   1.00    1.00    --   62.00  77.00-158.42   26
 15  \w    116.00 142.00   1.00    1.00    --   66.00  77.00  82.21   26
 16  \w     37.00  65.00   1.00    1.00    --   66.00  77.00-130.11   28
 17  \w     34.00  60.00   1.00    1.00    --   66.00  76.00 -37.43   26
 18  \w     33.00  67.00   1.00    1.00    --   66.00  77.00  82.21   34
 19  \w     34.00  60.00   1.00    1.00    --   66.00  76.00 -69.21   26
 20  \w    108.00 135.00   1.00    1.00    --   70.00  76.00-160.63   27
 21  \w     94.00 124.00   1.00    1.00    --   70.00  77.00 146.01   30
 22  \w     37.00  69.00   1.00    1.00    --   70.00  77.00 146.01   32
 23  \w     38.00  64.00   1.00    1.00    --   70.00  76.00  -7.04   26
 24  \w     37.00  74.00   1.00    1.00    --   70.00  77.00  28.83   37
 25  \w     38.00  75.00   1.00    1.00    --   70.00  76.00-160.63   37
 26  \w     41.00  83.00   1.00    1.00    --   74.00  77.00 106.03   42
 27  \w     78.00 105.00   1.00    1.02    --  107.17  61.00   0.00   27
 28  \w     75.00 177.00   1.00    1.02    --  107.17  77.00-180.00  102
 29  \w     66.00 117.00   1.00    1.02    --  107.17-125.00-180.00   51
 30  \w     75.00 177.00   1.00    1.02    --  107.17  77.00 150.00  102
 31  \w     76.00 176.00   1.00    1.02    --  107.17  77.00  90.00  100
 32  \w     75.00 170.00   1.00    1.02    --  107.17  77.00   0.00   95
 33  \w     78.00 110.00   1.00    1.02    --  107.17  61.00 -60.00   32
 34  \w     25.00 107.00   1.00    1.02    --  107.17 -94.00 -90.00   82
 35  \w     78.00 139.00   1.00    1.02    --  107.17  61.00-120.00   61
 36  \w     75.00 175.00   1.00    1.02    --  107.17  77.00  60.00  100
 37  \w     75.00 145.00   1.00    1.02    --  107.17  77.00 -30.00   70
 38  \w    116.00 143.00   1.00    1.02    --  107.17  77.00  30.00   27
 39  \w     76.00 101.00   1.00    1.02    --  107.17  77.00  30.00   25
 40  \w     26.00  83.00   1.00    1.02    --  107.17 -94.00  90.00   57
 41  \w    122.00 164.00   1.00    1.02    --  107.17  77.00 120.00   42
 42  \w     79.00 112.00   1.00    1.02    --  107.17  61.00  60.00   33
 43  \w     75.00 101.00   1.00    1.02    --  107.17  77.00 120.00   26
 44  \w     76.00 177.00   1.00    1.02    --  107.17  77.00 -60.00  101
 45  \w     80.00 107.00   1.00    1.02    --  107.17  61.00-150.00   27
 46  \w     78.00 104.00   1.00    1.02    --  107.17  61.00 -90.00   26
 47  \w    117.00 175.00   1.00    1.02    --  107.17  77.00 -90.00   58
 48  \w     75.00 172.00   1.00    1.02    --  107.17  77.00-120.00   97
 49  \w    117.00 143.00   1.00    1.02    --  107.17  77.00-150.00   26
 50  \w     83.00 116.00   1.00    1.02    --  107.17  61.00 150.00   33
 51  \w     75.00 101.00   1.00    1.02    --  107.17  77.00 -90.00   26
 52  \w     75.00 101.00   1.00    1.02    --  107.17  77.00-150.00   26
 53  \w     45.00 106.00   1.00    1.02    --  107.17 -94.00   0.00   61
 54  \w     28.00 107.00   1.00    1.02    --  107.17 -94.00-150.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0186680000
_diffrn_orient_matrix_UB_12      0.0200291000
_diffrn_orient_matrix_UB_13      0.0855587000
_diffrn_orient_matrix_UB_21      -0.1180125000
_diffrn_orient_matrix_UB_22      0.0721648000
_diffrn_orient_matrix_UB_23      0.0028513000
_diffrn_orient_matrix_UB_31      -0.0132443000
_diffrn_orient_matrix_UB_32      -0.1030253000
_diffrn_orient_matrix_UB_33      0.0678572000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44949
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.863
_diffrn_reflns_theta_min         3.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41826
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 8162 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1322
_refine_ls_number_reflns         19817
_refine_ls_number_restraints     444
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0766P)^2^+0.8089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                18783
_reflns_number_total             19817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra09284g2.cif
_cod_data_source_block           exp_1858
_cod_original_cell_volume        2652.24(9)
_cod_database_code               7244493
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOCl
_chemical_oxdiff_usercomment     R
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.804
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13A-C12A = C13-C12
 1.5 with sigma of 0.01
 N2-C12 = N2A-C12A
 1.47 with sigma of 0.01
 C12A-C11A = C11-C10 = C12-C11 = C11A-C10A
 1.54 with sigma of 0.01
 C12A-C10A
 2.515 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C12 \\sim N2 \\sim C11 \\sim C13 \\sim C10 \\sim C14 \\sim C18 \\sim C15 \\sim
C17 \\sim C16 \\sim C12A \\sim C13A \\sim C14A \\sim C18A \\sim C15A \\sim C17A
\\sim N2A \\sim C11A \\sim C16A \\sim C10A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C12, N2, C11, C13, C10, C14, C18, C15, C17, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N2A, C15A, C14A, C16A, C13A, C17A, C18A, C12A, C11A, C10A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H45C)=Sof(H45D)=Sof(C46A)=Sof(H46D)=Sof(H46E)=Sof(H46F)=1-FVAR(1)
 Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=FVAR(1)
 Sof(C13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=
 Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C12A)=Sof(H12A)=Sof(N2A)=Sof(H2AA)=
 Sof(H2AB)=Sof(C11A)=Sof(H11M)=Sof(H11N)=Sof(C10A)=Sof(H10N)=Sof(H10O)=
 Sof(H10P)=1-FVAR(2)
 Sof(N2)=Sof(H2C)=Sof(H2D)=Sof(C10)=Sof(H10K)=Sof(H10L)=Sof(H10M)=Sof(C11)=
 Sof(H11K)=Sof(H11L)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=
 Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C12(H12), C12A(H12A)
6.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C22(H22A,H22B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,
 H26B), C27(H27A,H27B), C35(H35A,H35B), C37(H37A,H37B), C45(H45A,H45B),
 C45(H45C,H45D), C47(H47A,H47B), C55(H55A,H55B), C57(H57A,H57B), C65(H65A,H65B),
  C67(H67A,H67B), C70(H70A,H70B), C72(H72A,H72B), C74(H74A,H74B), C75(H75A,
 H75B), C76(H76A,H76B), C77(H77A,H77B), C85(H85A,H85B), C87(H87A,H87B),
 C95(H95A,H95B), C97(H97A,H97B), C105(H10A,H10B), C107(H10F,H10G), C115(H11A,
 H11B), C117(H11F,H11G), C2(H2A,H2B), C11(H11K,H11L), C11A(H11M,H11N)
6.c Aromatic/amide H refined with riding coordinates:
 C31(H31), C33(H33), C34(H34), C41(H41), C43(H43), C44(H44), C51(H51),
 C53(H53), C54(H54), C61(H61), C63(H63), C64(H64), C81(H81), C83(H83), C84(H84),
  C91(H91), C93(H93), C94(H94), C101(H101), C103(H103), C104(H104), C111(H111),
 C113(H113), C114(H114), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C14A(H14A), C15A(H15A), C16A(H16A),
 C17A(H17A), C18A(H18A)
6.d Fitted hexagon refined as free rotating group:
 C13(C14,C15,C16,C17,C18), C13A(C14A,C15A,C16A,C17A,C18A)
6.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2C,H2D), N2A(H2AA,H2AB)
6.f Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C46(H46A,H46B,H46C), C48(H48A,H48B,
 H48C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C66(H66A,H66B,H66C), C68(H68A,
 H68B,H68C), C86(H86A,H86B,H86C), C88(H88A,H88B,H88C), C96(H96A,H96B,H96C),
 C98(H98A,H98B,H98C), C106(H10C,H10D,H10E), C108(H10H,H10I,H10J), C116(H11C,
 H11D,H11E), C118(H11H,H11I,H11J), C1(H1C,H1D,H1E), C10(H10K,H10L,H10M),
 C46A(H46D,H46E,H46F), C10A(H10N,H10O,H10P)
;
_shelx_res_checksum              76667
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.239
_oxdiff_exptl_absorpt_empirical_full_min 0.847