Creating porosity in a trianglimine macrocycle by heterochiral pairing.
He, Donglin; Clowes, Rob; Little, Marc A.; Liu, Ming; Cooper, Andrew I.; Chemical communications (Cambridge, England) 57 (2021) 6141–6144; doi:10.1039/d1cc01650d

data_7128361
_publ_section_title
;
 Creating porosity in a trianglimine macrocycle by heterochiral pairing.
;
_journal_issue                   50
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6141
_journal_page_last               6144
_journal_paper_doi               10.1039/d1cc01650d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         '2(C42 H48 N6), 2(C4 H8 O2), 2(O)'
_chemical_formula_sum            'C92 H112 N12 O6'
_chemical_formula_weight         1481.93
_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
_audit_creation_date             2020-11-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-03-27 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                89.815(3)
_cell_angle_beta                 77.839(4)
_cell_angle_gamma                60.849(4)
_cell_formula_units_Z            2
_cell_length_a                   14.3324(6)
_cell_length_b                   14.3555(6)
_cell_length_c                   25.1851(9)
_cell_measurement_reflns_used    15376
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.3690
_cell_measurement_theta_min      1.6550
_cell_volume                     4393.8(4)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.958
_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    -95.00  47.00   0.50    5.00    --   -8.90  15.00 153.00  284
  2  \w    -31.00  -5.00   0.50    5.00    --    5.00 -57.00 -90.00   52
  3  \w    -19.00   7.00   0.50    5.00    --    5.00  57.00-180.00   52
  4  \w    -95.00 -41.00   0.50    5.00    --   -8.90 -68.00   0.00  108
  5  \w    -17.00  28.00   0.50    5.00    --   -8.90 -68.00   0.00   90
  6  \w    -97.00  10.00   0.50    5.00    --   -8.90 -68.00 -60.00  214
  7  \w    -96.00  -1.00   0.50    5.00    --   -8.90 -57.00-180.00  190
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274798000
_diffrn_orient_matrix_UB_12      -0.0039499000
_diffrn_orient_matrix_UB_13      0.0209942000
_diffrn_orient_matrix_UB_21      0.0477064000
_diffrn_orient_matrix_UB_22      -0.0095582000
_diffrn_orient_matrix_UB_23      -0.0199789000
_diffrn_orient_matrix_UB_31      -0.0193504000
_diffrn_orient_matrix_UB_32      0.0559529000
_diffrn_orient_matrix_UB_33      0.0014596000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27498
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         1.635
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86304
_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    1.120
_exptl_crystal_description       prism
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     994
_refine_ls_number_reflns         27498
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.222
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0821
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16482
_reflns_number_total             27498
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9854\% 
around [0.44 0.90 0.01] (reciprocal) or [0.00 1.00 -0.00] (direct)
;
_cod_data_source_file            d1cc01650d2.cif
_cod_data_source_block           EA_1-rac_100K_publ
_cod_depositor_comments
'Adding full bibliography for 7128359--7128364.cif.'
_cod_original_cell_volume        4393.8(3)
_cod_database_code               7128361
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     DH_MC2-rac_EA
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5339(12)
 0.4661(12)
2. 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
3. Restrained distances
 O1-C91
 1.2 with sigma of 0.01
 C99-C100 = C94-C93
 1.49 with sigma of 0.01
 C90-C89
 1.51 with sigma of 0.01
 O2-C91
 1.34 with sigma of 0.01
 O2-C90
 1.45 with sigma of 0.01
 C92-C91
 1.49 with sigma of 0.01
 C87-C88
 1.51 with sigma of 0.01
 O3-C86
 1.34 with sigma of 0.01
 O3-C87
 1.45 with sigma of 0.01
 C85-C86
 1.49 with sigma of 0.01
 C85-O3
 2.31 with sigma of 0.01
 O4-C86
 1.2 with sigma of 0.02
 O6-C94 = O9-C99
 1.2 with sigma of 0.01
 O7-C94 = O8-C99
 1.34 with sigma of 0.01
 O8-C98 = O7-C95
 1.45 with sigma of 0.01
 C97-C98 = C95-C96
 1.51 with sigma of 0.01
 C93-O6
 2.34 with sigma of 0.02
 O9-C100
 2.34 with sigma of 0.02
 O1-C92
 2.34 with sigma of 0.02
4. Restrained planarity
 O6, O7, C93, C94, C95, C96
 with sigma of 0.01
 O3, O4, C85, C86, C87, C88
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uiso(C93) = Uiso(O6)
Uiso(C89) = Uiso(C88)
Uiso(O4) = Uiso(C85)
6. Rigid body (RIGU) restrains
 O6, O7, C93, C94, C95, C96
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O8, O9, C97, C98, C99, C100
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O1, O2, C89, C90, C91, C92
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O3, O4, C85, C86, C87, C88
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
7. Others
 Fixed Sof: O1(0.5) O2(0.5) C89(0.5) H89A(0.5) H89B(0.5) H89C(0.5) C90(0.5)
 H90A(0.5) H90B(0.5) C91(0.5) C92(0.5) H92A(0.5) H92B(0.5) H92C(0.5) O8(0.5)
 O9(0.5) C97(0.5) H97A(0.5) H97B(0.5) H97C(0.5) C98(0.5) H98A(0.5) H98B(0.5)
 C99(0.5) C100(0.5) H10A(0.5) H10B(0.5) H10C(0.5) O3(0.5) O4(0.5) C85(0.5)
 H85A(0.5) H85B(0.5) H85C(0.5) C86(0.5) C87(0.5) H87A(0.5) H87B(0.5) C88(0.5)
 H88A(0.5) H88B(0.5) H88C(0.5) O6(0.5) O7(0.5) C93(0.5) H93A(0.5) H93B(0.5)
 H93C(0.5) C94(0.5) C95(0.5) H95A(0.5) H95B(0.5) C96(0.5) H96A(0.5) H96B(0.5)
 H96C(0.5) O10(0.25) O11(0.5) O5(0.25) O12(0.25) O13(0.25) O14(0.25) O15(0.25)
8.a Ternary CH refined with riding coordinates:
 C25(H25), C30(H30), C31(H31), C36(H36), C37(H37), C42(H42), C67(H67),
 C72(H72), C73(H73), C78(H78), C79(H79), C84(H84)
8.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C32(H32A,
 H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C38(H38A,H38B),
 C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B), C68(H68A,H68B), C69(H69A,H69B),
  C70(H70A,H70B), C71(H71A,H71B), C74(H74A,H74B), C75(H75A,H75B), C76(H76A,
 H76B), C77(H77A,H77B), C80(H80A,H80B), C81(H81A,H81B), C82(H82A,H82B),
 C83(H83A,H83B), C90(H90A,H90B), C98(H98A,H98B), C87(H87A,H87B), C95(H95A,H95B)
8.c Me refined with riding coordinates:
 C93(H93A,H93B,H93C)
8.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24), C44(H44), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50),
 C52(H52), C54(H54), C55(H55), C56(H56), C57(H57), C58(H58), C60(H60), C62(H62),
  C63(H63), C64(H64), C65(H65), C66(H66)
8.e Idealised Me refined as rotating group:
 C89(H89A,H89B,H89C), C92(H92A,H92B,H92C), C97(H97A,H97B,H97C), C100(H10A,H10B,
 H10C), C85(H85A,H85B,H85C), C88(H88A,H88B,H88C), C96(H96A,H96B,H96C)
;
_shelx_res_checksum              93031
_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 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.805
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2