From Foldable Open Chains to Shape-Persistent Macrocycles: Synthesis, Impact on 2D Ordering, and Stimulated Self-Assembly.
Kim, Soobin; Castillo, Henry D.; Lee, Milim; Mortensen, Riley D.; Tait, Steven L.; Lee, Dongwhan; Journal of the American Chemical Society 140 (2018) 4726–4735; doi:10.1021/jacs.8b01805

data_4132133
_publ_section_title
;
 From Foldable Open Chains to Shape-Persistent Macrocycles: Synthesis,
 Impact on 2D Ordering, and Stimulated Self-Assembly.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4726
_journal_page_last               4735
_journal_paper_doi               10.1021/jacs.8b01805
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         '2(C H Cl3), C68 H68 N12 O4'
_chemical_formula_sum            'C70 H72 Cl6 N12 O4'
_chemical_formula_weight         1358.09
_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             2018-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                66.511(4)
_cell_angle_beta                 88.482(3)
_cell_angle_gamma                67.769(4)
_cell_formula_units_Z            1
_cell_length_a                   11.1142(4)
_cell_length_b                   13.0030(5)
_cell_length_c                   13.8223(5)
_cell_measurement_reflns_used    4582
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      28.6790
_cell_measurement_theta_min      3.9310
_cell_volume                     1677.58(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.818
_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    -39.00  60.00   1.00   10.71    --  -11.04  57.00 150.00   99
  2  \w    -80.00  16.00   1.00   10.71    --  -11.04 -57.00   0.00   96
  3  \w     34.00  99.00   1.00   10.71    --   11.51-178.00   0.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0450673000
_diffrn_orient_matrix_UB_12      -0.0549882000
_diffrn_orient_matrix_UB_13      -0.0015339000
_diffrn_orient_matrix_UB_21      0.0479136000
_diffrn_orient_matrix_UB_22      -0.0027154000
_diffrn_orient_matrix_UB_23      0.0348826000
_diffrn_orient_matrix_UB_31      -0.0230351000
_diffrn_orient_matrix_UB_32      -0.0344228000
_diffrn_orient_matrix_UB_33      0.0444981000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11711
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.477
_diffrn_reflns_theta_min         3.444
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       needle
_exptl_crystal_F_000             710
_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.246
_refine_diff_density_max         1.484
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0876
_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^)+(0.1330P)^2^+4.6084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2446
_refine_ls_wR_factor_ref         0.2639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5984
_reflns_number_total             7633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01805_si_002.cif
_cod_data_source_block           exp_64
_cod_original_cell_volume        1677.59(13)
_cod_database_code               4132133
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C70H72Cl6N12O4
_reflns_odcompleteness_completeness 98.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C017(H017)
2.b Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C00Z(H00C,H00D), C010(H01A,H01B), C011(H01C,H01D), C012(H01E,
 H01F), C013(H01G,H01H), C014(H01I,H01J), C016(H01N,H01O), C018(H01P,H01Q),
 C01A(H01U,H01V)
2.c Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00L(H00L), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00V(H00V), C00X(H00X)
2.d Idealised Me refined as rotating group:
 C015(H01K,H01L,H01M), C019(H01R,H01S,H01T)
;
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.659