Exploration of the polymorphic solid-state landscape of an amide-linked organic cage using computation and automation.
Shields, C. E.; Fellowes, T.; Slater, A. G.; Cooper, A. I.; Andrews, K. G.; Szczypiński, F T; Chemical communications (Cambridge, England) 60 (2024) 6023–6026; doi:10.1039/d4cc01407c

data_7132994
_publ_section_title
;
 Exploration of the polymorphic solid-state landscape of an amide-linked
 organic cage using computation and automation.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6023
_journal_page_last               6026
_journal_paper_doi               10.1039/d4cc01407c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C126 H112 N6 O10.002, 6[C2H6SO]'
_chemical_formula_sum            'C138 H148 N6 O16 S6'
_chemical_formula_weight         2338.98
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2024-03-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                94.1928(10)
_cell_angle_beta                 111.5642(11)
_cell_angle_gamma                109.9034(11)
_cell_formula_units_Z            4
_cell_length_a                   21.6989(3)
_cell_length_b                   27.1612(3)
_cell_length_c                   27.6258(3)
_cell_measurement_reflns_used    58501
_cell_measurement_temperature    100.10
_cell_measurement_theta_max      29.5370
_cell_measurement_theta_min      1.5210
_cell_volume                     13867.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.10
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f      0.00 180.00   0.20    0.20   0.00   0.00   0.00    --   900
  2  \w   -145.00  25.00   0.20    0.20    --   30.00   0.00   0.00  850
  3  \w   -145.00  25.00   0.20    0.20    --   30.00   0.00 120.00  850
  4  \w   -145.00  25.00   0.20    0.20    --   30.00   0.00 240.00  850
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            115133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        20.148
_diffrn_reflns_theta_max         20.148
_diffrn_reflns_theta_min         1.462
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.120
_exptl_crystal_description       block
_exptl_crystal_F_000             4968
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.081
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2714
_refine_ls_number_reflns         29012
_refine_ls_number_restraints     221
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0867
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1731P)^2^+4.3219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2694
_refine_ls_wR_factor_ref         0.2936
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18299
_reflns_number_total             29012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01407c3.cif
_cod_data_source_block           ka1_dmso_meoh
_cod_depositor_comments
'Adding full bibliography for 7132990--7132997.cif.'
_cod_database_code               7132994
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O246-C138
 1.3 with sigma of 0.004
 C7-C8 \\sim C7-C9 \\sim C7-C248 \\sim C8-C9 \\sim C8-C248 \\sim C9-C248
 with sigma of 0.04
 C239-C10 \\sim C239-C10A
 with sigma of 0.02
 C239-C200 \\sim C239-C10 \\sim C239-C28 \\sim C239-C34 \\sim C239-C10A \\sim
C239-C34A \\sim C239-C28A
 with sigma of 0.01
 C37A-C6 \\sim C37A-C1A \\sim C37A-C2A \\sim C37A-C3A
 with sigma of 0.02
 C37-C7 \\sim C37-C8 \\sim C37-C9 \\sim C37-C248
 with sigma of 0.02
 C6-C1A \\sim C6-C2A \\sim C6-C3A \\sim C1A-C2A \\sim C1A-C3A \\sim C2A-C3A
 with sigma of 0.02
 C126-C21 \\sim C126-C21A
 with sigma of 0.02
 C32-C52 \\sim C32A-C52A
 with sigma of 0.02
 C126-C32 \\sim C126-C32A
 with sigma of 0.04
 C126-C52 \\sim C126-C52A
 with sigma of 0.04
 C239-C28 \\sim C239-C28A
 with sigma of 0.02
 C239-C34 \\sim C239-C34A
 with sigma of 0.02
 C10-C28 \\sim C10-C34 \\sim C28-C34 \\sim C34A-C28A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C4, C2, C1, C6, C5, C181, C175, C202, C252, C219, C248, C3, C3A, C9, C8, C1A,
 C37A, C37, C2A, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C16A)=Sof(H16A)=Sof(C33A)=Sof(H33A)=Sof(C17A)=Sof(H17A)=Sof(C36A)=
 Sof(H36A)=1-FVAR(1)
 Sof(C16)=Sof(H16)=Sof(C33)=Sof(H33)=Sof(C17)=Sof(H17)=Sof(C36)=Sof(H36)=FVAR(1)
 Sof(C4)=Sof(C3)=Sof(H3)=Sof(C2)=Sof(C1)=Sof(H1)=Sof(C6)=Sof(C5)=Sof(H5)=
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=
 Sof(C37A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=1-FVAR(2)
 Sof(C181)=Sof(C175)=Sof(H175)=Sof(C202)=Sof(C252)=Sof(H252)=Sof(C248)=
 Sof(C219)=Sof(H219)=Sof(C37)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=FVAR(2)
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C52A)=Sof(H52D)=Sof(H52E)=
 Sof(H52F)=Sof(C32A)=Sof(H32D)=Sof(H32E)=Sof(H32F)=1-FVAR(3)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=
 Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=FVAR(3)
 Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=Sof(C34A)=Sof(H34D)=Sof(H34E)=
 Sof(H34F)=Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(4)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=FVAR(4)
 Fixed Sof: O2(0.667) H2(0.333333) O223(0.667) H223(0.333333) O262(0.667)
 H262(0.333333) O216(0.667) H216(0.333333) O250(0.667) H250(0.333333)
 O269(0.667) H269(0.333333) O1(0.667) H1A(0.333333) O237(0.667) H237(0.333333)
 O271(0.667) H271(0.333333)
5.a Ternary CH refined with riding coordinates:
 C046(H046), C024(H024), C051(H051), C053(H053)
5.b Me refined with riding coordinates:
 C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC), C3A(H3AA,H3AB,H3AC), C21(H21A,H21B,
 H21C), C32(H32A,H32B,H32C), C52(H52A,H52B,H52C), C7(H7A,H7B,H7C), C8(H8A,H8B,
 H8C), C9(H9A,H9B,H9C), C221(H22A,H22B,H22C), C226(H22D,H22E,H22F), C257(H25A,
 H25B,H25C), C274(H27A,H27B,H27C), C278(H27D,H27E,H27F), C22(H22G,H22H,H22I),
 C259(H25D,H25E,H25F), C275(H27G,H27H,H27I), C20(H20A,H20B,H20C), C191(H19A,
 H19B,H19C), C249(H24A,H24B,H24C), C263(H26A,H26B,H26C), C208(H20D,H20E,H20F),
 C232(H23A,H23B,H23C), C241(H24D,H24E,H24F), C18(H18A,H18B,H18C), C14(H14A,H14B,
 H14C), C97(H97A,H97B,H97C), C224(H22J,H22K,H22L), C251(H25G,H25H,H25I),
 C13(H13A,H13B,H13C), C169(H16B,H16C,H16D), C245(H24G,H24H,H24I), C276(H27J,
 H27K,H27L), C10(H10A,H10B,H10C), C28(H28A,H28B,H28C), C34(H34A,H34B,H34C),
 C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C30(H30A,H30B,H30C), C21A(H21D,H21E,
 H21F), C52A(H52D,H52E,H52F), C32A(H32D,H32E,H32F), C10A(H10D,H10E,H10F),
 C34A(H34D,H34E,H34F), C28A(H28D,H28E,H28F)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C5(H5), N035(H035), C055(H055), C070(H070), C083(H083),
 C101(H101), C047(H047), C058(H058), C099(H099), C136(H136), C090(H090),
 C199(H199), C012(H012), C067(H067), C175(H175), C252(H252), C219(H219),
 C097(H097), C018(H018), C113(H113), C064(H064), N007(H007), N073(H073),
 N132(H132), C084(H084), C131(H131), C165(H165), C168(H168), C129(H129),
 C178(H178), C108(H108), C159(H159), C103(H103), C133(H133), C173(H173),
 C235(H235), C258(H258), C125(H125), C176(H176), C227(H227), C233(H233),
 C062(H062), C077(H077), C027(H027), C094(H094), C093(H093), C098(H098),
 C162(H162), C111(H111), C011(H011), N009(H009), N085(H085), C143(H143),
 C106(H106), C155(H155), C048(H048), C004(H004), C039(H039), N036(H036),
 C044(H044), C071(H071), C134(H134), C110(H110), C153(H153), C190(H190),
 C092(H092), C146(H146), C196(H196), C118(H118), C218(H218), C220(H220),
 N163(H163), N109(H109), C206(H206), C210(H210), C197(H197), C240(H240),
 C157(H157), C198(H198), C074(H074), C148(H148), C255(H255), C192(H192),
 C078(H078), C243(H243), C244(H244), C16(H16), C33(H33), C16A(H16A), C33A(H33A),
  N041(H041), C266(H266), C247(H247), C17(H17), C36(H36), C17A(H17A),
 C36A(H36A), C096(H096), C040(H040), C158(H158), C204(H204), C193(H193),
 C217(H217), C119(H119), C184(H184), C045(H045), C063(H063), N022(H022),
 N029(H029), C120(H120), C082(H082), C130(H130), C142(H142)
5.d Fitted hexagon refined as free rotating group:
 C4(C3,C2,C1,C6,C5), C181(C175,C202,C252,C248,C219)
5.e Tetrahedral OH refined with riding coordinates:
 O2(H2), O223(H223), O262(H262), O216(H216), O250(H250), O269(H269), O1(H1A),
 O237(H237), O271(H271), O246(H246)
;
_shelx_res_checksum              43700
_shelx_hkl_checksum              45692
_shelx_fab_checksum              74252
_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
;