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_7132995
_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 H109 N6 O10.01, C126 H104 N6 O10, 30[C3H6O2]'
_chemical_formula_sum            'C342 H393 N12 O80.01'
_chemical_formula_weight         5951.82
_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             2024-03-27
_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                94.133(4)
_cell_angle_beta                 108.263(4)
_cell_angle_gamma                112.968(4)
_cell_formula_units_Z            2
_cell_length_a                   21.4803(10)
_cell_length_b                   27.0745(12)
_cell_length_c                   29.3858(17)
_cell_measurement_reflns_used    16637
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      20.375303161585347
_cell_measurement_theta_min      0.8054977627845308
_cell_volume                     14568.6(15)
_computing_data_collection       'GDA - generic data acquisition software'
_computing_data_reduction
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 3.12.1-2-g1c07bc2b3-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 3.12.0 (Winter, G., 2010)
;
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_av_unetI/netI     0.1014
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            116593
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        20.148
_diffrn_reflns_theta_max         20.148
_diffrn_reflns_theta_min         0.812
_diffrn_source_details           'Allan et al. (2017)'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9706066084980762
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
CCP4 8.0.007: AIMLESS, version 0.7.9 : 10/06/22
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       needle
_exptl_crystal_F_000             6338
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.406
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2569
_refine_ls_number_reflns         30461
_refine_ls_number_restraints     542
_refine_ls_restrained_S_all      1.424
_refine_ls_R_factor_all          0.1763
_refine_ls_R_factor_gt           0.1324
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3782
_refine_ls_wR_factor_ref         0.4083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17438
_reflns_number_total             30461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01407c3.cif
_cod_data_source_block           KA1_DMF_THP
_cod_depositor_comments
'Adding full bibliography for 7132990--7132997.cif.'
_cod_original_cell_volume        14568.5(14)
_cod_database_code               7132995
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.988
_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
 O16-C219
 1.38 with sigma of 0.02
 C35-C38 \\sim C35-C39 \\sim C35-C37 \\sim C38-C39 \\sim C38-C37 \\sim C39-C37
 with sigma of 0.04
 C60-C62 \\sim C60-C64 \\sim C60-C63 \\sim C62-C64 \\sim C62-C63 \\sim C64-C63
 with sigma of 0.04
 C61-C60 \\sim C61-C62 \\sim C61-C64 \\sim C61-C63
 with sigma of 0.02
 C134-C132 \\sim C134-C130 \\sim C133-C132 \\sim C133-C130
 with sigma of 0.04
 C151-C150 \\sim C151-C152 \\sim C151-C154 \\sim C151-C153
 with sigma of 0.03
 C176-C180 \\sim C176-C181 \\sim C176-C179 \\sim C180-C181 \\sim C180-C179
\\sim C181-C179
 with sigma of 0.03
 C150-C152 \\sim C150-C154 \\sim C150-C153 \\sim C152-C154 \\sim C152-C153
\\sim C154-C153
 with sigma of 0.03
 C131-C134 \\sim C131-C133 \\sim C131-C132 \\sim C131-C130
 with sigma of 0.02
 C178-C176 \\sim C178-C180 \\sim C178-C181 \\sim C178-C179
 with sigma of 0.02
 C79-C82 \\sim C79-C83 \\sim C82-C83
 with sigma of 0.04
 C52-C51 \\sim C52-C53 \\sim C52-C55 \\sim C52-C54
 with sigma of 0.03
 C80-C79 \\sim C80-C81 \\sim C80-C82 \\sim C80-C83
 with sigma of 0.02
 C51-C53 \\sim C51-C55 \\sim C51-C54 \\sim C53-C55 \\sim C53-C54 \\sim C55-C54
 with sigma of 0.1
 C36-C35 \\sim C36-C38 \\sim C36-C39 \\sim C36-C37
 with sigma of 0.02
 C204-C207 \\sim C204-C209 \\sim C204-C208 \\sim C207-C209 \\sim C207-C208
\\sim C209-C208
 with sigma of 0.04
 C162-C161 \\sim C162-C160 \\sim C162-C158 \\sim C161-C160 \\sim C161-C158
\\sim C160-C158
 with sigma of 0.04
 C187-C186 \\sim C187-C190 \\sim C187-C188 \\sim C187-C189
 with sigma of 0.02
 C206-C204 \\sim C206-C207 \\sim C206-C209 \\sim C206-C208
 with sigma of 0.02
 C27-C26 \\sim C26-C25
 with sigma of 0.04
 C24-C27 \\sim C24-C26 \\sim C24-C25 \\sim C24-C23
 with sigma of 0.02
 C8-C6 \\sim C8-C7 \\sim C8-C4 \\sim C6-C7 \\sim C6-C4 \\sim C7-C4
 with sigma of 0.04
 C5-C8 \\sim C5-C6 \\sim C5-C7 \\sim C5-C4
 with sigma of 0.02
 C159-C162 \\sim C159-C161 \\sim C159-C160 \\sim C159-C158
 with sigma of 0.02
 C186-C190 \\sim C186-C188 \\sim C186-C189 \\sim C190-C188
 with sigma of 0.04
 O7A-O7C \\sim O7A-O7B \\sim O7C-O7B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C181) \\sim Ueq, Uanis(C179) \\sim Ueq, Uanis(C180) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C62) \\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C63)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C153) \\sim Ueq, Uanis(C152) \\sim Ueq, Uanis(C151) \\sim Ueq,
Uanis(C154) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.08
Uanis(C196) \\sim Ueq, Uanis(C197) \\sim Ueq, Uanis(C199) \\sim Ueq,
Uanis(C198) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O8) \\sim Ueq, Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C83) \\sim Ueq, Uanis(C82) \\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(C80)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C55)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C142) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O10) \\sim Ueq, Uanis(C210) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(O7C) \\sim Ueq, Uanis(O7B) \\sim Ueq, Uanis(O7A) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C133) \\sim Ueq, Uanis(C131) \\sim Ueq, Uanis(C134) \\sim Ueq,
Uanis(C132) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O18) \\sim Ueq, Uanis(O19) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(O17) \\sim Ueq, Uanis(O16) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C38) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C37)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O4) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O11) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O12) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C160) \\sim Ueq, Uanis(C159) \\sim Ueq, Uanis(C161) \\sim Ueq,
Uanis(C162) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C170) \\sim Ueq, Uanis(C168) \\sim Ueq, Uanis(C169) \\sim Ueq,
Uanis(C167) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Fixed Sof: O7A(0.67) O7B(0.67) O7C(0.67)
5.a Me refined with riding coordinates:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C25(H25A,H25B,H25C),
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C), C39(H39A,H39B,H39C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C55(H55A,
 H55B,H55C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C),
 C82(H82A,H82B,H82C), C83(H83A,H83B,H83C), C81(H81A,H81B,H81C), C132(H13A,H13B,
 H13C), C133(H13D,H13E,H13F), C134(H13G,H13H,H13I), C152(H15A,H15B,H15C),
 C153(H15D,H15E,H15F), C154(H15G,H15H,H15I), C160(H16B,H16C,H16D), C161(H16E,
 H16F,H16G), C162(H16H,H16I,H16J), C179(H17A,H17B,H17C), C180(H18A,H18B,H18C),
 C181(H18D,H18E,H18F), C188(H18G,H18H,H18I), C189(H18J,H18K,H18L), C190(H19B,
 H19C,H19D), C207(H20A,H20B,H20C), C208(H20D,H20E,H20F), C209(H20G,H20H,H20I)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), C3(H3A), C9(H9A), C10(H10),
 C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C31(H31),
  C33(H33), C34(H34), C41(H41), C42(H42), C43(H43), C44(H44), C47(H47),
 C49(H49), C50(H50), C59(H59), C65(H65), C66(H66), C69(H69), C70(H70), C71(H71),
  C72(H72), C75(H75), C76(H76), C78(H78), C86(H86), C87(H87), C88(H88),
 C96(H96), C97(H97), C99(H99), C102(H102), C103(H103), C105(H105), C107(H107),
 C108(H108), C109(H109), C117(H117), C118(H118), C119(H119), C123(H123),
 C124(H124), C125(H125), N7(H7), N8(H8), N9(H9B), N10(H10A), N11(H11), N12(H12),
  C139(H139), C140(H140), C141(H141), C142(H142), C157(H157), C163(H163),
 C164(H164), C167(H167), C168(H168), C169(H169), C170(H170), C173(H173),
 C174(H174), C177(H177), C185(H185), C191(H191), C192(H192), C196(H196),
 C197(H197), C198(H198), C199(H199), C201(H201), C202(H202), C205(H205),
 C212(H212), C213(H213), C215(H215), C222(H222), C223(H223), C225(H225),
 C228(H228), C229(H229), C231(H231), C233(H233), C234(H234), C235(H235),
 C243(H243), C244(H244), C245(H245), C249(H249), C250(H250), C251(H251)
5.c Idealised tetrahedral OH refined as rotating group:
 O9(H9), O16(H16A), O19(H19A)
;
_shelx_res_checksum              25445
_shelx_hkl_checksum              3635
_shelx_fab_checksum              65003
_olex2_submission_special_instructions 'No special instructions were received'