Synthesis and structure of oxetane containing tripeptide motifs
Nicola H. Powell; Guy J. Clarkson; Rebecca Notman; Piotr Raubo; Nathaniel G. Martin; Michael Shipman; Chem.Commun. 50 (2014) 8797–; doi:10.1039/C4cc03507K

data_7115369
_publ_section_title
;
 Synthesis and structure of oxetane containing tripeptide motifs
;
_journal_name_full               Chem.Commun.
_journal_page_first              8797
_journal_paper_doi               10.1039/C4cc03507K
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H29 N3 O4, 0.1(C O)'
_chemical_formula_sum            'C19.1 H29.4 N3 O4.1'
_chemical_formula_weight         366.65
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                96.096(5)
_cell_angle_beta                 104.312(5)
_cell_angle_gamma                90.121(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4127(4)
_cell_length_b                   9.5002(5)
_cell_length_c                   13.3202(8)
_cell_measurement_reflns_used    6740
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.6630
_cell_measurement_theta_min      4.6910
_cell_volume                     1025.26(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1859519000
_diffrn_orient_matrix_UB_12      -0.0242303000
_diffrn_orient_matrix_UB_13      -0.0463932000
_diffrn_orient_matrix_UB_21      -0.0288567000
_diffrn_orient_matrix_UB_22      0.0247866000
_diffrn_orient_matrix_UB_23      0.1103716000
_diffrn_orient_matrix_UB_31      -0.0181155000
_diffrn_orient_matrix_UB_32      0.1595389000
_diffrn_orient_matrix_UB_33      -0.0107757000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19052
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.230
_diffrn_reflns_theta_min         3.445
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).

The molecules contain chiral centres assigned by reference to 
unchanging chiral centres in the synthetic procedure.
;
_refine_ls_abs_structure_Flack   -0.11(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         8088
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0657P)^2^+0.2850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                6999
_reflns_number_total             8088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc03507k2.cif
_cod_data_source_block           np3
_cod_original_cell_volume        1025.27(10)
_cod_original_formula_sum        'C19.10 H29.40 N3 O4.10'
_cod_database_code               7115369
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C40 H40 N6 O8'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H110 of N110, H210 of N210, All C(H,H) groups, All N(H,H,
  H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H116 of N116, H216 of N216
2. Restrained distances
 N116-H116 = N216-H216
 0.9 with sigma of 0.02
3. Others
 Fixed Sof: O1(0.2) C2(0.2)
4.a Ternary CH refined with riding coordinates:
 C108(H108), C117(H117), C120(H120), C208(H208), C217(H217), C220(H220)
4.b Secondary CH2 refined with riding coordinates:
 C107(H10A,H10B), C111(H11A,H11B), C113(H11C,H11D), C115(H11E,H11F), C121(H12A,
 H12B), C207(H20A,H20B), C211(H21A,H21B), C213(H21C,H21D), C215(H21E,H21F),
 C221(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C101(H101), C102(H102), C103(H103), C104(H104), C105(H105), N110(H110),
 C201(H201), C202(H202), C203(H203), C204(H204), C205(H205), N210(H210)
4.d Idealised Me refined as rotating group:
 N108(H10C,H10D,H10E), C122(H12C,H12D,H12E), C123(H12F,H12G,H12H), N208(H20C,
 H20D,H20E), C222(H22C,H22D,H22E), C223(H22F,H22G,H22H)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'