Conformationally Adaptable Macrocyclic Receptors for Ditopic Anions: Analysis of Chelate Cooperativity in Aqueous Containing Media
Berry, Stuart N.; Qin, Lei; Lewis, William; Jolliffe, Katrina A.; Chemical Science  (2020) –; doi:10.1039/D0SC02533J

data_1558360
_publ_section_title
;
 Conformationally Adaptable Macrocyclic Receptors for Ditopic Anions:
 Analysis of Chelate Cooperativity in Aqueous Containing Media
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02533J
_journal_year                    2020
_chemical_formula_moiety
'2(C3 H2 O4), 4(C16 H36 N), 2.5(C2 H6 O S), C60 H71 N10 S4, C60 H70 N10 S4'
_chemical_formula_sum            'C195 H307 N24 O12 S10.5'
_chemical_formula_weight         3516.26
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-03-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-20 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                100.331(5)
_cell_angle_beta                 91.268(5)
_cell_angle_gamma                100.461(6)
_cell_formula_units_Z            2
_cell_length_a                   15.483(4)
_cell_length_b                   22.547(6)
_cell_length_c                   30.092(7)
_cell_measurement_reflns_used    6029
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.40
_cell_measurement_theta_min      2.39
_cell_volume                     10147(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Nonius APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'mirror optics'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2465
_diffrn_reflns_av_unetI/netI     0.2623
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            205681
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         0.689
_diffrn_source                   'rotating anode'
_diffrn_source_type              'FR591 rotating anode source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1405 before and 0.0848 after correction. The Ratio of minimum to maximum transmission is 0.7732. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       tablet
_exptl_crystal_F_000             3818
_exptl_crystal_recrystallization_method 'crystallised from DMSO'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.066
_refine_diff_density_max         1.152
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2406
_refine_ls_number_reflns         35875
_refine_ls_number_restraints     7917
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.3255
_refine_ls_R_factor_gt           0.1516
_refine_ls_shift/su_max          0.006
_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          0.3601
_refine_ls_wR_factor_ref         0.4546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12720
_reflns_number_total             35875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02533j2.cif
_cod_data_source_block           kaj19_s1746_sq
_cod_original_formula_sum        'C195 H307 N24 O12 S10.50'
_cod_database_code               1558360
_sydney_internal_submission_code kaj19_s1746
_sydney_internal_submission_date 2019-02-15
_sydney_internal_submission_number s1746
_sydney_internal_client_code     SNB
_sydney_internal_client_email    stuart.berry@sydney.edu.au
_sydney_internal_client_name     'Stuart Berry'
_sydney_internal_supervisor_code kaj
_sydney_internal_supervisor_name 'Kate Jolliffe'
_sydney_internal_collection_date 2019-02-25
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-02-26
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-03-01
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-03-05
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-03-05
_sydney_internal_check_user      wlew0588
_platon_squeeze_void_probe_radius 1.20
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 O1_3-C2_3 \\sim O3_3-C2_3 \\sim O4_3-C2_3 \\sim O2_3-C2_3 \\sim O1_4-C2_4
\\sim O2_4-C2_4 \\sim O3_4-
 C2_4 \\sim O4_4-C2_4
 with sigma of 0.02
 O2_3-C1_3 \\sim O4_3-C3_3 \\sim O3_3-C3_3 \\sim O1_3-C1_3 \\sim O1_4-C1_4
\\sim O2_4-C1_4 \\sim O3_4-
 C3_4 \\sim O4_4-C3_4
 with sigma of 0.02
 O1_4-O2_4 \\sim O1_3-O2_3 \\sim O3_3-O4_3 \\sim O3_4-O4_4
 with sigma of 0.02
 C2_4-C3_4 \\sim C2_3-C3_3 \\sim C1_4-C2_4 \\sim C1_3-C2_3
 with sigma of 0.02
 C1_4-C3_4 \\sim C1_3-C3_3
 with sigma of 0.02
 C57_1-C57_1 \\sim C57_1-C57_1 \\sim C57_1-C57_1 \\sim C45_1-C46_1 \\sim
C45_1-C47_1 \\sim C45_1-
 C48_1 \\sim C49_1-C50_1 \\sim C49_1-C51_1 \\sim C49_1-C52_1 \\sim C53_1-C54_1
\\sim C53_1-C55_1 ~
 C53_1-C56_1 \\sim C45_2-C46_2 \\sim C45_2-C47_2 \\sim C45_2-C48_2 \\sim
C49_2-C50_2 \\sim C49_2-
 C51_2 \\sim C49_2-C52_2 \\sim C53_2-C54_2 \\sim C53_2-C55_2 \\sim C53_2-C56_2
\\sim C57_2-C58_2 ~
 C57_2-C59_2 \\sim C57_2-C60_2
 with sigma of 0.02
 C8_2-C13_2 \\sim C30_2-C35_2 \\sim C25_2-C26_2 \\sim C30_1-C35_1 \\sim
C25_1-C26_1 \\sim C8_1-
 C13_1 \\sim C3_1-C4_1 \\sim C3_2-C4_2
 with sigma of 0.02
 C31_1-C36_1 \\sim C23_1-C24_1 \\sim C9_1-C14_1 \\sim C1_1-C2_1 \\sim C1_2-C2_2
\\sim C9_2-C14_2 ~
 C23_2-C24_2 \\sim C31_2-C36_2
 with sigma of 0.02
 N2_1-C3_1 \\sim N9_1-C30_1 \\sim N7_1-C25_1 \\sim N2_2-C3_2 \\sim N7_2-C25_2
\\sim N9_2-C30_2 ~
 N4_1-C8_1 \\sim N4_2-C8_2
 with sigma of 0.02
 C24_1-C26_1 \\sim C31_1-C35_1 \\sim C9_1-C13_1 \\sim C2_1-C4_1 \\sim C2_2-C4_2
\\sim C9_2-C13_2 ~
 C24_2-C26_2 \\sim C31_2-C35_2
 with sigma of 0.02
 C9_1-C11_1 \\sim C31_1-C33_1 \\sim C24_1-C28_1 \\sim C2_1-C6_1 \\sim C2_2-C6_2
\\sim C9_2-C11_2 ~
 C24_2-C28_2 \\sim C31_2-C33_2
 with sigma of 0.02
 C25_1-C29_1 \\sim C3_1-C7_1 \\sim C30_1-C32_1 \\sim C8_1-C10_1 \\sim C3_2-C7_2
\\sim C8_2-C10_2 ~
 C25_2-C29_2 \\sim C30_2-C32_2
 with sigma of 0.02
 N8_1-C26_1 \\sim N8_1-C35_1 \\sim N3_1-C13_1 \\sim N3_1-C4_1 \\sim N3_2-C4_2
\\sim N3_2-C13_2 ~
 N8_2-C26_2 \\sim N8_2-C35_2
 with sigma of 0.02
 C27_1-C35_1 \\sim C4_1-C12_1 \\sim C5_1-C13_1 \\sim C26_1-C34_1 \\sim
C4_2-C12_2 \\sim C5_2-C13_2
 \\sim C26_2-C34_2 \\sim C27_2-C35_2
 with sigma of 0.02
 C27_1-C29_1 \\sim C10_1-C12_1 \\sim C32_1-C34_1 \\sim C5_1-C7_1 \\sim
C5_2-C7_2 \\sim C10_2-C12_2
 \\sim C27_2-C29_2 \\sim C32_2-C34_2
 with sigma of 0.02
 C29_1-C53_1 \\sim C32_1-C57_1 \\sim C7_1-C45_1 \\sim C10_1-C49_1 \\sim
C7_2-C45_2 \\sim C10_2-
 C49_2 \\sim C29_2-C53_2 \\sim C32_2-C57_2
 with sigma of 0.02
 C6_1-C46_1 \\sim C11_1-C52_1 \\sim C28_1-C54_1 \\sim C28_1-C55_1 \\sim
C28_1-C56_1 \\sim C33_1-
 C33_1 \\sim C33_1-C33_1 \\sim C33_1-C33_1 \\sim C6_1-C47_1 \\sim C6_1-C48_1
\\sim C11_1-C50_1 ~
 C11_1-C51_1 \\sim C6_2-C46_2 \\sim C6_2-C47_2 \\sim C6_2-C48_2 \\sim
C11_2-C50_2 \\sim C11_2-C51_2
 \\sim C11_2-C52_2 \\sim C28_2-C54_2 \\sim C28_2-C55_2 \\sim C28_2-C56_2 \\sim
C33_2-C58_2 \\sim C33_2-
 C59_2 \\sim C33_2-C60_2
 with sigma of 0.02
 N4_1-C14_1 \\sim N4_2-C14_2 \\sim N7_2-C23_2 \\sim N9_2-C36_2 \\sim N2_2-C1_2
\\sim N2_1-C1_1 ~
 N7_1-C23_1 \\sim N9_1-C36_1
 with sigma of 0.02
 C18_1-C19_1 \\sim C19_1-C20_1 \\sim C16_1-C21_1 \\sim C40_1-C41_1 \\sim
C41_1-C42_1 \\sim C38_1-
 C43_1 \\sim C38_1-C39_1 \\sim C18_2-C19_2 \\sim C19_2-C20_2 \\sim C16_2-C21_2
\\sim C38_2-C39_2 ~
 C40_2-C41_2 \\sim C41_2-C42_2 \\sim C38_2-C43_2
 with sigma of 0.02
 C12_2-C13_2 \\sim C34_2-C35_2 \\sim C26_2-C27_2 \\sim C26_1-C27_1 \\sim
C4_2-C5_2 \\sim C12_1-
 C13_1 \\sim C34_1-C35_1 \\sim C4_1-C5_1
 with sigma of 0.02
 C32_1-C33_1 \\sim C6_1-C7_1 \\sim C6_2-C7_2 \\sim C10_2-C11_2 \\sim
C28_2-C29_2 \\sim C32_2-C33_2
 \\sim C10_1-C11_1 \\sim C28_1-C29_1
 with sigma of 0.02
 C47_1-C48_1 \\sim C55_1-C56_1 \\sim C54_1-C56_1 \\sim C46_1-C48_1 \\sim
C50_1-C51_1 \\sim C51_1-
 C52_1 \\sim C50_1-C52_1 \\sim C54_1-C55_1 \\sim C46_1-C47_1 \\sim C46_2-C47_2
\\sim C46_2-C48_2 ~
 C47_2-C48_2 \\sim C50_2-C51_2 \\sim C50_2-C52_2 \\sim C51_2-C52_2 \\sim
C54_2-C55_2 \\sim C54_2-
 C56_2 \\sim C55_2-C56_2 \\sim C58_2-C59_2 \\sim C58_2-C60_2 \\sim C59_2-C60_2
 with sigma of 0.02
 C20_1-C21_1 \\sim C39_2-C40_2 \\sim C42_2-C43_2 \\sim C42_1-C43_1 \\sim
C17_1-C18_1 \\sim C17_2-
 C18_2 \\sim C39_1-C40_1 \\sim C20_2-C21_2
 with sigma of 0.02
 N10_2-C37_2 \\sim N5_2-C15_2 \\sim N6_2-C22_2 \\sim N5_1-C15_1 \\sim
N1_2-C44_2 \\sim N1_1-C44_1
 \\sim N10_1-C37_1 \\sim N6_1-C22_1
 with sigma of 0.02
 C31_2-C32_2 \\sim C24_1-C29_1 \\sim C2_2-C7_2 \\sim C9_2-C10_2 \\sim
C31_1-C32_1 \\sim C9_1-C10_1
 \\sim C2_1-C7_1 \\sim C24_2-C29_2
 with sigma of 0.02
 N8_2-C25_2 \\sim N8_1-C30_1 \\sim N3_2-C3_2 \\sim N3_2-C8_2 \\sim N3_1-C3_1
\\sim N3_1-C8_1 ~
 N8_1-C25_1 \\sim N8_2-C30_2
 with sigma of 0.02
 C42_1-C44_1 \\sim C15_1-C21_1 \\sim C20_1-C22_1 \\sim C18_1-C22_1 \\sim
C37_1-C39_1 \\sim C37_1-
 C43_1 \\sim C40_1-C44_1 \\sim C15_1-C17_1 \\sim C15_2-C17_2 \\sim C15_2-C21_2
\\sim C18_2-C22_2 ~
 C20_2-C22_2 \\sim C37_2-C39_2 \\sim C37_2-C43_2 \\sim C40_2-C44_2 \\sim
C42_2-C44_2
 with sigma of 0.02
 S4_2-C36_2 \\sim S3_2-C23_2 \\sim S3_1-C23_1 \\sim S1_1-C1_1 \\sim S2_1-C14_1
\\sim S1_2-C1_2 ~
 S2_2-C14_2 \\sim S4_1-C36_1
 with sigma of 0.02
 C2_2-C3_2 \\sim C30_1-C31_1 \\sim C2_1-C3_1 \\sim C24_2-C25_2 \\sim C8_2-C9_2
\\sim C8_1-C9_1 ~
 C30_2-C31_2 \\sim C24_1-C25_1
 with sigma of 0.02
 C17_1-C19_1 \\sim C16_1-C18_1 \\sim C38_1-C40_1 \\sim C38_1-C42_1 \\sim
C39_1-C41_1 \\sim C41_1-
 C43_1 \\sim C19_1-C21_1 \\sim C16_1-C20_1 \\sim C16_2-C18_2 \\sim C17_2-C19_2
\\sim C16_2-C20_2 ~
 C19_2-C21_2 \\sim C38_2-C40_2 \\sim C39_2-C41_2 \\sim C38_2-C42_2 \\sim
C41_2-C43_2
 with sigma of 0.02
 N10_1-C36_1 \\sim N1_1-C1_1 \\sim N6_1-C23_1 \\sim N5_1-C14_1 \\sim N6_2-C23_2
\\sim N5_2-C14_2 ~
 N1_2-C1_2 \\sim N10_2-C36_2
 with sigma of 0.02
 C6_2-C45_2 \\sim C28_2-C53_2 \\sim C33_2-C57_2 \\sim C11_2-C49_2 \\sim
C11_1-C49_1 \\sim C28_1-
 C53_1 \\sim C33_1-C57_1 \\sim C6_1-C45_1
 with sigma of 0.02
 N10_1-C38_1 \\sim N6_1-C19_1 \\sim N5_1-C16_1 \\sim N1_1-C41_1 \\sim
N5_2-C16_2 \\sim N6_2-C19_2
 \\sim N10_2-C38_2 \\sim N1_2-C41_2
 with sigma of 0.02
 N7_1-C29_1 \\sim N9_1-C32_1 \\sim N2_1-C7_1 \\sim N4_1-C10_1 \\sim N2_2-C7_2
\\sim N4_2-C10_2 ~
 N7_2-C29_2 \\sim N9_2-C32_2
 with sigma of 0.02
 C41_1-C44_1 \\sim C37_2-C38_2 \\sim C15_2-C16_2 \\sim C19_2-C22_2 \\sim
C15_1-C16_1 \\sim C41_2-
 C44_2 \\sim C19_1-C22_1 \\sim C37_1-C38_1
 with sigma of 0.02
 C5_1-C6_1 \\sim C33_1-C34_1 \\sim C11_1-C12_1 \\sim C27_1-C28_1 \\sim
C27_2-C28_2 \\sim C5_2-C6_2
 \\sim C33_2-C34_2 \\sim C11_2-C12_2
 with sigma of 0.02
 N9_2-C31_2 \\sim N2_2-C2_2 \\sim N4_2-C9_2 \\sim N2_1-C2_1 \\sim N4_1-C9_1
\\sim N7_2-C24_2 ~
 N9_1-C31_1 \\sim N7_1-C24_1
 with sigma of 0.02
 N3_2-C9_2 \\sim N3_1-C9_1 \\sim N8_1-C24_1 \\sim N8_1-C31_1 \\sim N8_2-C31_2
\\sim N8_2-C24_2 ~
 N3_1-C2_1 \\sim N3_2-C2_2
 with sigma of 0.02
 C26_1-C28_1 \\sim C33_1-C35_1 \\sim C26_2-C28_2 \\sim C11_1-C13_1 \\sim
C11_2-C13_2 \\sim C33_2-
 C35_2 \\sim C4_1-C6_1 \\sim C4_2-C6_2
 with sigma of 0.02
 C30_1-C34_1 \\sim C8_1-C12_1 \\sim C3_1-C5_1 \\sim C25_1-C27_1 \\sim C3_2-C5_2
\\sim C30_2-C34_2
 \\sim C25_2-C27_2 \\sim C8_2-C12_2
 with sigma of 0.02
 S3_1-N6_1 \\sim S2_1-N5_1 \\sim S4_1-N10_1 \\sim S3_2-N6_2 \\sim S1_1-N1_1
\\sim S1_2-N1_2 \\sim S2_2-
 N5_2 \\sim S4_2-N10_2
 with sigma of 0.02
 N9_1-N10_1 \\sim N4_1-N5_1 \\sim N6_1-N7_1 \\sim N1_1-N2_1 \\sim N6_2-N7_2
\\sim N9_2-N10_2 ~
 N1_2-N2_2 \\sim N4_2-N5_2
 with sigma of 0.02
 S1_1-N2_1 \\sim S2_1-N4_1 \\sim S4_1-N9_1 \\sim S3_1-N7_1 \\sim S4_2-N9_2
\\sim S2_2-N4_2 \\sim S1_2-
 N2_2 \\sim S3_2-N7_2
 with sigma of 0.02
 C17_1-C21_1 \\sim C18_1-C20_1 \\sim C18_2-C20_2 \\sim C40_1-C42_1 \\sim
C17_2-C21_2 \\sim C40_2-
 C42_2 \\sim C39_1-C43_1 \\sim C39_2-C43_2
 with sigma of 0.02
 C14_2-C15_2 \\sim C14_1-C15_1 \\sim C1_1-C44_1 \\sim C36_1-C37_1 \\sim
C22_1-C23_1 \\sim C1_2-
 C44_2 \\sim C22_2-C23_2 \\sim C36_2-C37_2
 with sigma of 0.02
 C26_1-C30_1 \\sim C25_1-C35_1 \\sim C3_1-C13_1 \\sim C4_1-C8_1 \\sim
C25_2-C35_2 \\sim C4_2-C8_2
 \\sim C26_2-C30_2 \\sim C3_2-C13_2
 with sigma of 0.02
 C27_2-C53_2 \\sim C27_1-C53_1 \\sim C34_1-C57_1 \\sim C12_1-C49_1 \\sim
C5_1-C45_1 \\sim C12_2-
 C49_2 \\sim C5_2-C45_2 \\sim C34_2-C57_2
 with sigma of 0.02
 C16_2-C17_2 \\sim C16_1-C17_1
 with sigma of 0.02
 C26_2-C35_2 \\sim C26_1-C35_1 \\sim C4_1-C13_1 \\sim C4_2-C13_2
 with sigma of 0.02
 C25_1-C30_1 \\sim C3_1-C8_1 \\sim C25_2-C30_2 \\sim C3_2-C8_2
 with sigma of 0.02
 C1_5-C5_5 \\sim C1_6-C13_6 \\sim C5_6-C13_6 \\sim C9_6-C13_6 \\sim C1_7-C5_7
\\sim C1_7-C9_7 ~
 C5_7-C9_7 \\sim C1_7-C13_7 \\sim C5_7-C13_7 \\sim C9_7-C13_7 \\sim C1_5-C9_5
\\sim C1_5-C13_5 ~
 C5_5-C9_5 \\sim C5_5-C13_5 \\sim C9_5-C13_5 \\sim C1_6-C5_6 \\sim C1_6-C9_6
\\sim C5_6-C9_6
 with sigma of 0.02
 C6_5-C8_5 \\sim C14_5-C16_5 \\sim C10_5-C12_5 \\sim C2_6-C4_6 \\sim C6_6-C8_6
\\sim C10_7-C12_7 ~
 C6_7-C8_7 \\sim C10_6-C12_6 \\sim C14_6-C16_6 \\sim C14_7-C16_7 \\sim
C2_7-C4_7 \\sim C2_5-C4_5
 with sigma of 0.02
 C13_6-C14_6 \\sim C13_7-C14_7 \\sim C9_7-C10_7 \\sim C9_5-C10_5 \\sim
C1_5-C2_5 \\sim C1_6-C2_6 ~
 C5_6-C6_6 \\sim C9_6-C10_6 \\sim C5_7-C6_7 \\sim C1_7-C2_7 \\sim C5_5-C6_5
\\sim C13_5-C14_5
 with sigma of 0.02
 C9_7-C11_7 \\sim C9_6-C11_6 \\sim C9_5-C11_5 \\sim C5_5-C7_5 \\sim C13_5-C15_5
\\sim C1_5-C3_5 ~
 C13_6-C15_6 \\sim C1_7-C3_7 \\sim C5_7-C7_7 \\sim C13_7-C15_7 \\sim C1_6-C3_6
\\sim C5_6-C7_6
 with sigma of 0.02
 N1_7-C2_7 \\sim N1_6-C2_6 \\sim N1_5-C14_5 \\sim N1_6-C6_6 \\sim N1_6-C10_6
\\sim N1_6-C14_6 ~
 N1_7-C6_7 \\sim N1_7-C10_7 \\sim N1_7-C14_7 \\sim N1_5-C2_5 \\sim N1_5-C6_5
\\sim N1_5-C10_5
 with sigma of 0.02
 N1_6-C9_6 \\sim N1_7-C1_7 \\sim N1_6-C1_6 \\sim N1_5-C9_5 \\sim N1_7-C9_7
\\sim N1_5-C5_5 \\sim N1_6-
 C5_6 \\sim N1_5-C13_5 \\sim N1_6-C13_6 \\sim N1_7-C5_7 \\sim N1_7-C13_7 \\sim
N1_5-C1_5
 with sigma of 0.02
 C6_6-C7_6 \\sim C6_7-C7_7 \\sim C10_6-C11_6 \\sim C10_7-C11_7 \\sim C2_7-C3_7
\\sim C6_5-C7_5 ~
 C2_5-C3_5 \\sim C10_5-C11_5 \\sim C2_6-C3_6 \\sim C14_5-C15_5 \\sim
C14_7-C15_7 \\sim C14_6-C15_6
 with sigma of 0.02
 C7_7-C8_7 \\sim C15_6-C16_6 \\sim C11_5-C12_5 \\sim C11_6-C12_6 \\sim
C11_7-C12_7 \\sim C15_7-
 C16_7 \\sim C15_5-C16_5 \\sim C7_5-C8_5 \\sim C3_6-C4_6 \\sim C3_7-C4_7 \\sim
C7_6-C8_6 \\sim C3_5-C4_5
 with sigma of 0.02
 C2_14-C2_14 \\sim S1_13-C2_13 \\sim S1_13-C1_13 \\sim C1_14-C1_14
 with sigma of 0.02
 O1_14-O1_14 \\sim S1_13-O1_13
 with sigma of 0.02
 O1_14-C1_14 \\sim O1_13-C1_13 \\sim O1_14-C2_14 \\sim O1_13-C2_13
 with sigma of 0.02
 C1_13-C2_13 \\sim C1_14-C2_14
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.008 and sigma
for terminal atoms of 0.016
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H1BD)=Sof(H1BE)=Sof(H1BF)=Sof(H2BD)=Sof(H2BE)=Sof(H2BF)=Sof(S1A)=1-FVAR(1)
 Sof(S1)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=FVAR(1)
 Sof(H1BD)=Sof(H1BE)=Sof(H1BF)=Sof(H2BD)=Sof(H2BE)=Sof(H2BF)=Sof(S1A)=0.5*(1-
 FVAR(3))
 Sof(S1)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=0.5*FVAR(3)
 Sof(C58A)=Sof(H58D)=Sof(H58E)=Sof(H58F)=Sof(C59A)=Sof(H59D)=Sof(H59E)=
 Sof(H59F)=Sof(C60A)=Sof(H60D)=Sof(H60E)=Sof(H60F)=1-FVAR(3)
 Sof(C58)=Sof(H58A)=Sof(H58B)=Sof(H58C)=Sof(C59)=Sof(H59A)=Sof(H59B)=Sof(H59C)=
 Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(H60C)=FVAR(3)
 Fixed Sof: N1(0.5) C1(0.5) H1A(0.5) H1B(0.5) C2(0.5) H2A(0.5) H2B(0.5)
 C3(0.5) H3A(0.5) H3B(0.5) C4(0.5) H4A(0.5) H4B(0.5) H4C(0.5) C5(0.5) H5A(0.5)
 H5B(0.5) C6(0.5) H6A(0.5) H6B(0.5) C7(0.5) H7A(0.5) H7B(0.5) C8(0.5) H8A(0.5)
 H8B(0.5) H8C(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5) H10A(0.5) H10B(0.5)
 C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) C14(0.5) H14A(0.5) H14B(0.5) C15(0.5) H15A(0.5) H15B(0.5)
 C16(0.5) H16A(0.5) H16B(0.5) H16C(0.5) N1(0.5) C1(0.5) H1A(0.5) H1B(0.5)
 C2(0.5) H2A(0.5) H2B(0.5) C3(0.5) H3A(0.5) H3B(0.5) C4(0.5) H4A(0.5) H4B(0.5)
 H4C(0.5) C5(0.5) H5A(0.5) H5B(0.5) C6(0.5) H6A(0.5) H6B(0.5) C7(0.5) H7A(0.5)
 H7B(0.5) C8(0.5) H8A(0.5) H8B(0.5) H8C(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5)
 H10A(0.5) H10B(0.5) C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) H12B(0.5)
 H12C(0.5) C13(0.5) H13A(0.5) H13B(0.5) C14(0.5) H14A(0.5) H14B(0.5) C15(0.5)
 H15A(0.5) H15B(0.5) C16(0.5) H16A(0.5) H16B(0.5) H16C(0.5) O1(0.5) C1(0.5)
 C2(0.5)
6.a Riding coordinates:
 N1(H1)
6.b Ternary CH refined with riding coordinates:
 C6(H6A)
6.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2(H2A,H2B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B),
 C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C1(H1A,H1B), C2(H2A,H2B),
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C1(H1A,
 H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,
 H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C15(H15A,H15B), C22(H22A,H22B), C37(H37A,H37B), C44(H44A,H44B), C1(H1A,
 H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,
 H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C15(H15A,H15B), C22(H22A,H22B), C37(H37A,H37B), C44(H44A,H44B), C1(H1A,
 H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,
 H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B)
6.d Me refined with riding coordinates:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C12(H12A,H12B,H12C), C1(H1A,H1B,H1C),
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C46(H46A,H46B,H46C), C52(H52A,H52B,H52C),
 C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C58(H58A,H58B,H58C), C59(H59A,H59B,
 H59C), C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C47(H47A,H47B,
 H47C), C58(H58A,H58B,H58C), C58A(H58D,H58E,H58F), C2(H2AA,H2AB,H2AC), C2(H2BD,
 H2BE,H2BF), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C1(H1AA,H1AB,H1AC),
 C1(H1BD,H1BE,H1BF), C2(H2AA,H2AB,H2AC)
6.e Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), N7(H7), N8(H8), N9(H9), N10(H10),
 C5(H5A), C7(H7A), C10(H10A), C12(H12), C17(H17), C18(H18), C20(H20), C21(H21),
 C27(H27), C29(H29), C32(H32), C34(H34), C39(H39), C40(H40), C42(H42), C43(H43),
  N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), N7(H7), N8(H8), N9(H9),
 N10(H10), C5(H5A), C7(H7A), C10(H10A), C12(H12), C17(H17), C18(H18), C20(H20),
 C21(H21), C27(H27), C29(H29), C32(H32), C34(H34), C39(H39), C40(H40), C42(H42),
  C43(H43)
6.f Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C16(H16A,H16B,H16C), C4(H4A,H4B,H4C), C8(H8A,H8B,H8C),
 C16(H16A,H16B,H16C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C),
  C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C50(H50A,H50B,H50C), C51(H51A,H51B,
 H51C), C56(H56A,H56B,H56C), C60(H60A,H60B,H60C), C12(H12A,H12B,H12C), C46(H46A,
 H46B,H46C), C48(H48A,H48B,H48C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C),
 C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C56(H56A,H56B,
 H56C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C59A(H59D,H59E,H59F),
 C60A(H60D,H60E,H60F), C1(H1AA,H1AB,H1AC), C1(H1BD,H1BE,H1BF), C4(H4A,H4B,H4C),
 C8(H8A,H8B,H8C), C2(H2BD,H2BE,H2BF)
;
_shelx_res_checksum              29262
_shelx_fab_checksum              82407
_olex2_date_sample_data_collection 2019-02-25
_olex2_date_sample_submission    2019-02-15
_olex2_exptl_crystal_mounting_method 'in paratone-N on a micromount'
_olex2_submission_original_sample_id 'SB-1-100 plus TBA (2) Malonate -2 '
_olex2_submission_special_instructions 'No special instructions were received'