Synthetic Factors Governing Access to Tris(β-diketimine) Cyclophanes versus Tripodal Tri-β-aminoenones
Eaton, Mary C.; Knight, Brian J.; Brahmi, Robin; Ferreira, Ricardo B.; Catalano, Vincent J.; Rheingold, Arnold L.; Ghiviriga, Ion; Murray, Leslie J.; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01708

data_4038924
_publ_section_title
;
 Synthetic Factors Governing Access to Tris(\b-diketimine) Cyclophanes
 versus Tripodal Tri-\b-aminoenones
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01708
_journal_year                    2020
_chemical_formula_moiety         'C48 H72 N6, C7 H8'
_chemical_formula_sum            'C55 H80 N6'
_chemical_formula_weight         825.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.290(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7848(18)
_cell_length_b                   30.833(3)
_cell_length_c                   16.9686(18)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.809
_cell_measurement_theta_min      2.27
_cell_volume                     9820.2(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            89454
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         1.270
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.2080
_exptl_absorpt_correction_T_min  0.1801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0822 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.8659.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_description       block
_exptl_crystal_F_000             3616
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1131
_refine_ls_number_reflns         22543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0663
_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^)+(0.1142P)^2^+2.6540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.2086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14816
_reflns_number_total             22543
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01708_si_002.cif
_cod_data_source_block           murray03_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        9820.4(17)
_cod_database_code               4038924
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.981
_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
2.a Secondary CH2 refined with riding coordinates:
 C83(H00A,H00B), C66(H01U,H01V), C46(H01A,H01B), C95(H01W,H01X), C13(H01C,
 H01D), C45(H01E,H01F), C18(H01G,H01H), C90(H,H01Y), C73(H01Z,HA), C37(H01I,
 H01J), C94(H01,HB), C27(H01K,H01L), C82(H3AA,HC), C75(H4AA,HD), C9(H01M,H01N),
 C48(H01O,H01P), C34(H01Q,H01R), C26(H01S,H01T), C92(H5AA,HE), C58(H7AA,HH),
 C7(H02A,H02B), C55(H8AA,HI), C40(H02F,H02G), C64(H9AA,HJ)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H001), N7(H004), N10(H005), N12(H007), N2(H008), N3(H009), C105(H027),
 C109(H3CA), C106(H032), C102(H033), C108(H034), C107(H035), C101(H03P),
 C99(H03Q), C100(H03R), C98(H03S)
2.c Idealised Me refined as rotating group:
 C91(H6AA,HF,HG), C24(H02C,H02D,H02E), C49(H0BA,HK,HL), C25(H02H,H02I,H02J),
 C47(H02K,H02L,H02M), C89(H1BA,HM,HN), C38(H02N,H02O,H02P), C87(H2BA,HO,HP),
 C74(H3BA,HQ,HR), C77(H4BA,HS,HT), C14(H02Q,H02R,H02S), C81(H5BA,HU,HV),
 C96(H6BA,HW,HX), C8(H02T,H02U,H02V), C33(H02W,H02X,H02Y), C29(H02Z,HY,HZ),
 C54(H4CA,H5CA,H7BA), C93(H6CA,H7CA,H8BA), C39(H02,H8CA,H9CA), C31(H0AA,H0DA,
 H1DA), C1(H1AA,H2DA,H3DA), C6(H2AA,H4DA,H5DA), C59(H6DA,H7DA,H9BA), C52(H0CA,
 H8DA,H9DA), C79(H0EA,H1CA,H1EA), C65(H2CA,H2EA,H3EA), C20(H03A,H03B,H03C),
 C88(H03J,H03K,H03L), C4(H03D,H03E,H03F), C110(H03M,H03N,H03O), C22(H03G,H03H,
 H03I), C103(H03T,H03U,H03V)
;
_shelx_res_checksum              83111
_shelx_hkl_checksum              4962
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'