Controllable Self-Assembly of Macrocycles in Water for Isolating Aromatic Hydrocarbon Isomers.
Wu, Guangcheng; Wang, Cai-Yun; Jiao, Tianyu; Zhu, Huangtianzhi; Huang, Feihe; Li, Hao; Journal of the American Chemical Society 140 (2018) 5955–5961; doi:10.1021/jacs.8b01651

data_4132112
_publ_section_title
;
 Controllable Self-Assembly of Macrocycles in Water for Isolating Aromatic
 Hydrocarbon Isomers.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5955
_journal_page_last               5961
_journal_paper_doi               10.1021/jacs.8b01651
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '2(Cl), C34 H32 N6 O2'
_chemical_formula_sum            'C34 H32 Cl2 N6 O2'
_chemical_formula_weight         627.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   44.7259(13)
_cell_length_b                   26.8344(9)
_cell_length_c                   13.9270(4)
_cell_measurement_reflns_used    9678
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      39.72
_cell_measurement_theta_min      2.95
_cell_volume                     16715.1(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            185278
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.103
_diffrn_reflns_theta_min         2.865
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1291 before and 0.0767 after correction. The Ratio of minimum to maximum transmission is 0.6942. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.997
_exptl_crystal_description       block
_exptl_crystal_F_000             5248
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 5232 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.629(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     1561
_refine_ls_number_reflns         30262
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0923
_refine_ls_shift/su_max          0.011
_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          0.2626
_refine_ls_wR_factor_ref         0.3074
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                15745
_reflns_number_total             30262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01651_si_005.cif
_cod_data_source_block           mjl18015
_cod_depositor_comments
;

2020-05-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C136 H128 Cl8 N24 O8'
_cod_original_formula_weight         2510.22
_cod_original_formula_moiety         '8(Cl), 4(C34 H32 N6 O2)'
_cod_original_formula_units_Z            4
_cod_database_code               4132112
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.882
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C5-C11 = C5-C1 = C134-C1
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C11 \\sim C5 \\sim C1 \\sim C134: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.08
C101 \\sim C068 \\sim C0AA \\sim C14 \\sim C102 \\sim C139: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Riding coordinates:
 N192(H192)
4.b Secondary CH2 refined with riding coordinates:
 C081(H08A,H08B), C098(H09A,H09B), C117(H11A,H11B), C128(H12A,H12B), C129(H12C,
 H12D), C133(H13E,H13F), C134(H13C,H13D), C135(H13A,H13B), C142(H14A,H14B),
 C144(H14C,H14D), C157(H15A,H15B), C160(H16E,H16F), C162(H16C,H16D), C168(H16A,
 H16B), C174(H17A,H17B), C177(H17C,H17D), C178(H17E,H17F), C184(H18A,H18B),
 C222(H22A,H22B), C223(H22E,H22F), C225(H22C,H22D), C11(H11C,H11D), C1(H1A,H1B),
  C5(H5A,H5B)
4.c Aromatic/amide H refined with riding coordinates:
 C011(H011), C013(H013), C014(H014), C016(H016), N017(H017), C023(H023),
 C024(H024), C026(H026), C031(H031), C033(H033), C034(H034), N036(H036),
 C037(H037), C038(H038), C039(H039), C041(H041), N042(H042), C043(H043),
 C045(H045), C046(H046), C047(H047), N049(H049), C050(H050), C052(H052),
 C053(H053), C056(H056), C057(H057), C058(H058), C059(H059), C060(H060),
 C061(H061), C062(H062), C063(H063), C111(H111), C158(H158), C231(H231),
 C070(H070), C074(H074), C077(H077), N078(H078), C079(H079), C080(H080),
 C082(H082), C084(H084), C085(H085), N088(H088), C090(H090), C093(H093),
 C095(H095), C096(H096), C097(H097), C102(H102), C14(H14), C0AA(H0AA),
 C103(H103), C105(H105), C106(H106), C107(H107), C109(H109), C112(H112),
 C113(H113), C114(H114), C116(H116), C121(H121), C123(H123), C124(H124),
 C125(H125), C126(H126), C131(H131), C136(H136), C137(H137), C138(H138),
 C145(H145), C147(H147), C163(H163), C167(H167), N179(H179), C199(H199), C8(H8)
4.d Fitted hexagon refined as free rotating group:
 C066(C152,C149,C111,C158,C231), C101(C139,C102,C14,C0AA,C068)
;
_shelx_res_checksum              14845
_shelx_hkl_checksum              50815
_shelx_fab_checksum              76001
_olex2_submission_special_instructions 'No special instructions were received'