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_7244492
_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 ad
_chemical_formula_moiety         'C9 H12 O, C50 H64 O8'
_chemical_formula_sum            'C59 H76 O9'
_chemical_formula_weight         929.19
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-06 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                66.8377(12)
_cell_angle_beta                 81.2331(11)
_cell_angle_gamma                63.0183(13)
_cell_formula_units_Z            2
_cell_length_a                   14.49400(19)
_cell_length_b                   14.69060(18)
_cell_length_c                   15.1758(2)
_cell_measurement_reflns_used    58637
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      75.9830
_cell_measurement_theta_min      3.3840
_cell_volume                     2646.14(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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      3.00  31.00   1.00    4.00    --   38.00  86.00 -86.76   28
  2  \w   -115.00 -17.00   1.00    4.00    --  -41.14 -38.00 -60.00   98
  3  \w   -114.00 -13.00   1.00    4.00    --  -41.14 -57.00  60.00  101
  4  \w    -66.00  33.00   1.00    4.00    --  -41.14  38.00  30.00   99
  5  \w    -87.00  -6.00   1.00    4.00    --  -41.14 125.00-180.00   81
  6  \w   -115.00 -17.00   1.00    4.00    --  -41.14 -38.00-150.00   98
  7  \w     27.00  97.00   1.00    4.00    --   41.14-125.00 120.00   70
  8  \w      6.00  32.00   1.00    4.00    --   41.14  85.00  89.37   26
  9  \w     13.00  42.00   1.00    4.00    --   46.00  80.00 167.98   29
 10  \w     16.00  42.00   1.00    4.00    --   50.00  81.00 -10.02   26
 11  \w     16.00  42.00   1.00    4.00    --   50.00  82.00  71.37   26
 12  \w     16.00  42.00   1.00    4.00    --   50.00  81.00-105.50   26
 13  \w     30.00 137.00   1.00    4.00    --   62.00  74.00 125.03  107
 14  \w     31.00 136.00   1.00    4.00    --   62.00  71.00 -54.58  105
 15  \w     30.00 137.00   1.00    4.00    --   62.00  74.00  28.92  107
 16  \w     35.00 140.00   1.00    4.00    --   66.00  71.00 -88.63  105
 17  \w     34.00 141.00   1.00    4.00    --   66.00  74.00  -1.62  107
 18  \w     39.00 144.00   1.00    4.00    --   70.00  70.00-155.87  105
 19  \w     38.00 145.00   1.00    4.00    --   70.00  74.00 148.22  107
 20  \w     38.00 145.00   1.00    4.00    --   70.00  73.00  58.37  107
 21  \w     42.00 149.00   1.00    4.00    --   74.00  73.00 167.32  107
 22  \w     44.00 147.00   1.00    4.00    --   74.00  65.00  94.25  103
 23  \w     43.00 148.00   1.00    4.00    --   74.00  72.00-134.28  105
 24  \w     42.00 149.00   1.00    4.00    --   74.00  74.00 -52.83  107
 25  \w     42.00 149.00   1.00    4.00    --   74.00  74.00 107.22  107
 26  \w     53.00 154.00   1.00   16.00    --   82.00  61.00 -69.45  101
 27  \w     54.00 161.00   1.00   16.00    --   86.00  74.00-144.09  107
 28  \w     55.00 160.00   1.00   16.00    --   86.00  70.00 175.03  105
 29  \w     58.00 159.00   1.00   16.00    --   86.00  58.00  21.20  101
 30  \w     57.00 158.00   1.00   16.00    --   86.00  62.00 -35.66  101
 31  \w     61.00 162.00   1.00   16.00    --   90.00  61.00   5.43  101
 32  \w     64.00 167.00   1.00   16.00    --   94.00  67.00-139.74  103
 33  \w     73.00 174.00   1.00   16.00    --  102.00  61.00  97.02  101
 34  \w     72.00 175.00   1.00   16.00    --  102.00  64.00  51.92  103
 35  \w     83.00 178.00   1.00   16.00    --  112.00  61.00-180.00   95
 36  \w     83.00 178.00   1.00   16.00    --  112.00  61.00-120.00   95
 37  \w     36.00 109.00   1.00   16.00    --  112.00-111.00 -30.00   73
 38  \w     29.00 107.00   1.00   16.00    --  112.00 -94.00-120.00   78
 39  \w     83.00 178.00   1.00   16.00    --  112.00  61.00  90.00   95
 40  \w     31.00 106.00   1.00   16.00    --  112.00 -94.00-150.00   75
 41  \w     41.00 109.00   1.00   16.00    --  112.00-111.00  60.00   68
 42  \w     83.00 172.00   1.00   16.00    --  112.00  61.00 120.00   89
 43  \w     84.00 178.00   1.00   16.00    --  112.00  61.00   0.00   94
 44  \w    120.00 176.00   1.00   16.00    --  112.00  59.00 -90.22   56
 45  \w    140.00 166.00   1.00   16.00    --  112.00  61.00  60.00   26
 46  \w     84.00 116.00   1.00   16.00    --  112.00  61.00  60.00   32
 47  \w     83.00 115.00   1.00   16.00    --  112.00  59.00 -90.22   32
 48  \w    124.00 175.00   1.00   16.00    --  112.00  61.00-150.00   51
 49  \w     83.00 119.00   1.00   16.00    --  112.00  61.00-150.00   36
 50  \w     83.00 177.00   1.00   16.00    --  112.00  61.00 -60.00   94
 51  \w     83.00 167.00   1.00   16.00    --  112.00  61.00 150.00   84
 52  \w     47.00 108.00   1.00   16.00    --  112.00-111.00-180.00   61
 53  \w    123.00 174.00   1.00   16.00    --  112.00  61.00  30.00   51
 54  \w     83.00 116.00   1.00   16.00    --  112.00  61.00  30.00   33
 55  \w     47.00  94.00   1.00   16.00    --  112.00 -61.00  60.00   47
 56  \w    113.00 160.00   1.00   16.00    --  112.00  61.00 -30.00   47
 57  \w     83.00 110.00   1.00   16.00    --  112.00  61.00 -30.00   27
 58  \w     77.00 109.00   1.00   16.00    --  112.00-111.00  90.00   32
 59  \w     45.00  74.00   1.00   16.00    --  112.00-111.00  90.00   29
 60  \w     43.00 141.00   1.00   16.00    --  112.00 -61.00-120.00   98
 61  \w    116.00 141.00   1.00   16.00    --  112.00 -61.00  60.00   25
;
_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      0.0347692000
_diffrn_orient_matrix_UB_12      -0.1181945000
_diffrn_orient_matrix_UB_13      0.0739183000
_diffrn_orient_matrix_UB_21      -0.0575552000
_diffrn_orient_matrix_UB_22      -0.0237081000
_diffrn_orient_matrix_UB_23      -0.0595037000
_diffrn_orient_matrix_UB_31      0.0985847000
_diffrn_orient_matrix_UB_32      -0.0385422000
_diffrn_orient_matrix_UB_33      -0.0565602000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            79146
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.135
_diffrn_reflns_theta_min         3.169
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.166
_exptl_crystal_description       plate
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 8844 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       0.00036(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1222
_refine_ls_number_reflns         20430
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0688P)^2^+0.9161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                19800
_reflns_number_total             20430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra09284g2.cif
_cod_data_source_block           exp_1807
_cod_database_code               7244492
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     OGC-1
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.893
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.a Ternary CH refined with riding coordinates:
 C3(H3), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11X,H11Y), C20(H20A,H20B), C22(H22A,H22B), C24(H24A,H24B),
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C53(H53A,H53B), C55(H55A,H55B),
  C57(H57A,H57B), C59(H59A,H59B), C61(H61A,H61B), C63(H63A,H63B), C65(H65A,
 H65B), C67(H67A,H67B), C70(H70A,H70B), C72(H72A,H72B), C74(H74A,H74B),
 C76(H76A,H76B), C77(H77A,H77B), C78(H78A,H78B), C103(H10A,H10B), C105(H10F,
 H10G), C107(H10K,H10L), C109(H10P,H10Q), C111(H11D,H11E), C113(H11I,H11J),
 C115(H11N,H11O), C117(H11S,H11T)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C7(H7), C6(H6), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C31(H31), C33(H33), C34(H34), C37(H37), C39(H39), C40(H40),
  C43(H43), C45(H45), C46(H46), C49(H49), C51(H51), C52(H52), C81(H81),
 C83(H83), C84(H84), C87(H87), C89(H89), C90(H90), C93(H93), C95(H95), C96(H96),
  C99(H99), C101(H101), C102(H102)
2.d Fitted hexagon refined as free rotating group:
 C4(C9,C8,C7,C6,C5), C13(C14,C15,C16,C17,C18)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10R,H10S,H10T), C54(H54A,H54B,H54C), C56(H56A,H56B,
 H56C), C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C62(H62A,H62B,H62C), C64(H64A,
 H64B,H64C), C66(H66A,H66B,H66C), C68(H68A,H68B,H68C), C104(H10C,H10D,H10E),
 C106(H10H,H10I,H10J), C108(H10M,H10N,H10O), C110(H11A,H11B,H11C), C112(H11F,
 H11G,H11H), C114(H11K,H11L,H11M), C116(H11P,H11Q,H11R), C118(H11U,H11V,H11W)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              73596
_olex2_date_sample_data_collection 2021-06-19
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.564