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_7132996
_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
'0.5(C126 H112 N6 O10), 0.5(C126 H108 N6 O10), 9.5[C3H7ON]'
_chemical_formula_sum            'C154.5 H176.5 N15.5 O19.5'
_chemical_formula_weight         2562.60
_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                93.8640(10)
_cell_angle_beta                 111.2560(10)
_cell_angle_gamma                110.4410(10)
_cell_formula_units_Z            4
_cell_length_a                   21.6013(2)
_cell_length_b                   27.1502(2)
_cell_length_c                   28.3933(3)
_cell_measurement_reflns_used    30624
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      23.558893619502395
_cell_measurement_theta_min      0.7914217364191166
_cell_volume                     14178.7(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0716
_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       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            122084
_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         0.796
_diffrn_source_details           'Allan et al. (2017)'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9905318412049627
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       needle
_exptl_crystal_F_000             5472
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.013
_refine_diff_density_max         1.092
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.404
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2598
_refine_ls_number_reflns         29682
_refine_ls_number_restraints     503
_refine_ls_restrained_S_all      1.460
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.1060
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3365
_refine_ls_wR_factor_ref         0.3610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20603
_reflns_number_total             29682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01407c3.cif
_cod_data_source_block           KA1_DMF_TFE
_cod_depositor_comments
'Adding full bibliography for 7132990--7132997.cif.'
_cod_original_cell_volume        14178.6(3)
_cod_original_formula_sum        'C154.50 H176.50 N15.50 O19.50'
_cod_database_code               7132996
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.985
_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
 O7-C240
 1.38 with sigma of 0.02
 C15-C158 \\sim C15-C160 \\sim C15-C161 \\sim C15-C162
 with sigma of 0.02
 C17-C13 \\sim C17-C13A
 with sigma of 0.04
 C17-C16 \\sim C17-C16A
 with sigma of 0.02
 C178-C176 \\sim C178-C179 \\sim C178-C181 \\sim C178-C180
 with sigma of 0.01
 C16-C14 \\sim C16A-C14A
 with sigma of 0.04
 C131-C133 \\sim C131-C134 \\sim C131-C135 \\sim C133-C134 \\sim C133-C135
\\sim C134-C135
 with sigma of 0.04
 C17-C14 \\sim C17-C14A
 with sigma of 0.04
 C132-C131 \\sim C132-C133 \\sim C132-C134 \\sim C132-C135
 with sigma of 0.02
 C159-C14 \\sim C253-C14A
 with sigma of 0.02
 C158-C160 \\sim C158-C161 \\sim C158-C162 \\sim C160-C161 \\sim C160-C162
\\sim C161-C162
 with sigma of 0.04
 C159-C13 \\sim C253-C13A
 with sigma of 0.04
 C16-C13 \\sim C16A-C13A
 with sigma of 0.02
 C14-C13 \\sim C14A-C13A
 with sigma of 0.02
 C176-C179 \\sim C176-C181 \\sim C176-C180 \\sim C179-C181 \\sim C179-C180
\\sim C181-C180
 with sigma of 0.01
 C12-C14 \\sim C12-C14A
 with sigma of 0.02
 C12-C13 \\sim C12-C13A
 with sigma of 0.02
 C61-C60 \\sim C61-C64 \\sim C61-C62 \\sim C61-C63
 with sigma of 0.02
 C17-C159 \\sim C17-C253
 with sigma of 0.02
 C12-C159 \\sim C12-C253
 with sigma of 0.04
 C12-C16 \\sim C12-C16A
 with sigma of 0.04
 C60-C64 \\sim C60-C62 \\sim C60-C63 \\sim C64-C62 \\sim C64-C63 \\sim C62-C63
 with sigma of 0.04
 C80-C77 \\sim C80-C81 \\sim C80-C82 \\sim C80-C83
 with sigma of 0.02
 C77-C81 \\sim C77-C82 \\sim C77-C83 \\sim C81-C82 \\sim C81-C83 \\sim C82-C83
 with sigma of 0.04
 C190-C189 \\sim C190-C188 \\sim C190-C186 \\sim C189-C188 \\sim C189-C186
\\sim C188-C186
 with sigma of 0.04
 C187-C190 \\sim C187-C189 \\sim C187-C188 \\sim C187-C186
 with sigma of 0.02
 C204-C209 \\sim C204-C208 \\sim C204-C207 \\sim C209-C208 \\sim C209-C207
\\sim C208-C207
 with sigma of 0.04
 C206-C204 \\sim C206-C209 \\sim C206-C208 \\sim C206-C207
 with sigma of 0.02
 C36-C35 \\sim C36-C34 \\sim C36-C32 \\sim C35-C34 \\sim C35-C32 \\sim C34-C32
 with sigma of 0.04
 C33-C36 \\sim C33-C35 \\sim C33-C34 \\sim C33-C32
 with sigma of 0.02
 C54-C53 \\sim C54-C55 \\sim C54-C50 \\sim C53-C55 \\sim C53-C50 \\sim C55-C50
 with sigma of 0.04
 C52-C54 \\sim C52-C53 \\sim C52-C55 \\sim C52-C50
 with sigma of 0.02
 C4-C8 \\sim C4-C6 \\sim C4-C7 \\sim C8-C6 \\sim C8-C7 \\sim C6-C7
 with sigma of 0.04
 C5-C4 \\sim C5-C8 \\sim C5-C6 \\sim C5-C7
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C134) \\sim Ueq, Uanis(C133) \\sim Ueq, Uanis(C132) \\sim Ueq,
Uanis(C135) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C161) \\sim Ueq, Uanis(C160) \\sim Ueq, Uanis(C162) \\sim Ueq,
Uanis(C158) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C61) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C62)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C180) \\sim Ueq, Uanis(C181) \\sim Ueq, Uanis(C179) \\sim Ueq,
Uanis(C178) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O16) \\sim Ueq, Uanis(O17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O4) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C139) \\sim Ueq, Uanis(C141) \\sim Ueq, Uanis(C143) \\sim Ueq,
Uanis(C142) \\sim Ueq, Uanis(C140) \\sim Ueq, Uanis(C138) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C174) \\sim Ueq, Uanis(C176) \\sim Ueq, Uanis(C177) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(O6) \\sim Ueq, Uanis(O7) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C81) \\sim Ueq, Uanis(C80) \\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C82)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim
Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O13) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O15) \\sim Ueq, Uanis(O14) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C71) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C70)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Sof(C13A)=Sof(H13A)=Sof(C14)=Sof(H14)=Sof(C16A)=Sof(H16A)=Sof(C159)=Sof(H159)=
 1-FVAR(1)
 Sof(C13)=Sof(H13)=Sof(C14A)=Sof(H14A)=Sof(C16)=Sof(H16B)=Sof(C253)=Sof(H253)=
 FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C217(H217), C238(H238), C91(H91)
5.b Me refined with riding coordinates:
 C133(H13B,H13C,H13D), C134(H13E,H13F,H13G), C135(H13H,H13I,H13J), C151(H15A,
 H15B,H15C), C152(H15D,H15E,H15F), C153(H15G,H15H,H15I), C160(H16C,H16D,H16E),
 C161(H16F,H16G,H16H), C162(H16I,H16J,H16K), C179(H17A,H17B,H17C), C180(H18A,
 H18B,H18C), C181(H18D,H18E,H18F), C188(H18G,H18H,H18I), C189(H18J,H18K,H18L),
 C190(H19A,H19B,H19C), C207(H20A,H20B,H20C), C208(H20D,H20E,H20F), C209(H20G,
 H20H,H20I), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C34(H34A,H34B,H34C), C35(H35A,
 H35B,H35C), C36(H36A,H36B,H36C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C),
 C55(H55A,H55B,H55C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C64(H64A,H64B,
 H64C), C81(H81A,H81B,H81C), C82(H82A,H82B,H82C), C83(H83A,H83B,H83C)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3A), N4(H4A), N5(H5), N6(H6), C129(H129), C130(H130),
 C136(H136), C139(H139), C140(H140), C141(H141), C142(H142), C145(H145),
 C146(H146), C148(H148), 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), C195(H195), C196(H196), C197(H197),
 C198(H198), C201(H201), C202(H202), C205(H205), C212(H212), C213(H213),
 C214(H214), 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), N7(H7), N8(H8), N9(H9),
 N10(H10), N11(H11), N12(H12), C3(H3), C9(H9A), C10(H10A), C19(H19), C20(H20),
 C23(H23), C41(H41), C42(H42), C43(H43), C44(H44), C47(H47), C48(H48), C51(H51),
  C59(H59), C65(H65), C66(H66), C69(H69), C70(H70), C71(H71), C72(H72),
 C75(H75), C76(H76), C79(H79), C86(H86), C87(H87), C88(H88), C96(H96), C97(H97),
  C98(H98), C102(H102), C103(H103), C105(H105), C107(H107), C108(H108),
 C109(H109), C117(H117), C118(H118), C120(H120), C123(H123), C124(H124),
 C126(H126), C13A(H13A), C14(H14), C16A(H16A), C159(H159), C13(H13), C14A(H14A),
  C16(H16B), C253(H253)
5.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O7(H7D), O15(H15), O16(H16)
;
_shelx_res_checksum              93881
_shelx_hkl_checksum              98130
_shelx_fab_checksum              15396
_olex2_submission_special_instructions 'No special instructions were received'