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_7115368
_publ_section_title
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 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         'C16 H31 N3 O4'
_chemical_formula_sum            'C16 H31 N3 O4'
_chemical_formula_weight         329.44
_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                77.134(3)
_cell_angle_beta                 81.935(2)
_cell_angle_gamma                80.958(2)
_cell_formula_units_Z            4
_cell_length_a                   8.5557(2)
_cell_length_b                   14.0932(5)
_cell_length_c                   16.3070(4)
_cell_measurement_reflns_used    14859
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.9310
_cell_measurement_theta_min      4.7270
_cell_volume                     1881.71(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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1334878000
_diffrn_orient_matrix_UB_12      0.0103104000
_diffrn_orient_matrix_UB_13      0.0505107000
_diffrn_orient_matrix_UB_21      0.1132723000
_diffrn_orient_matrix_UB_22      -0.0761444000
_diffrn_orient_matrix_UB_23      -0.0419720000
_diffrn_orient_matrix_UB_31      0.0547428000
_diffrn_orient_matrix_UB_32      0.0829817000
_diffrn_orient_matrix_UB_33      -0.0720519000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34050
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.435
_diffrn_reflns_theta_min         3.244
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45750
_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    1.163
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 5638 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   0.12(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     866
_refine_ls_number_reflns         14895
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0644
_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^)+(0.1026P)^2^+0.5133P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1836
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.917
_reflns_Friedel_fraction_max     0.859
_reflns_number_gt                13615
_reflns_number_total             14895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc03507k2.cif
_cod_data_source_block           np2
_cod_original_cell_volume        1881.70(9)
_cod_database_code               7115368
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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, All N(H) groups, All N(H,H,H) groups
2. Restrained distances
 N113-H113 = N213-H213 = N313-H313 = N413-H413
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C102(H102), C105(H105), C114(H114), C118(H118), C202(H202), C205(H205),
 C214(H214), C218(H218), C302(H302), C305(H305), C314(H314), C318(H318),
 C402(H402), C405(H405), C414(H414), C418(H418)
3.b Secondary CH2 refined with riding coordinates:
 C104(H10G,H10H), C108(H10L,H10M), C110(H11A,H11B), C112(H11C,H11D), C119(H11E,
 H11F), C204(H20G,H20H), C208(H20L,H20M), C210(H21A,H21B), C212(H21C,H21D),
 C219(H21E,H21F), C304(H30G,H30H), C308(H30L,H30M), C310(H31A,H31B), C312(H31C,
 H31D), C319(H31E,H31F), C404(H40G,H40H), C408(H40L,H40M), C410(H41A,H41B),
 C412(H41C,H41D), C419(H41E,H41F)
3.c Aromatic/amide H refined with riding coordinates:
 N107(H107), N207(H207), N307(H307), N407(H407)
3.d Idealised Me refined as rotating group:
 C101(H10A,H10B,H10C), C103(H10D,H10E,H10F), N105(H10I,H10J,H10K), C120(H12A,
 H12B,H12C), C121(H12D,H12E,H12F), C201(H20A,H20B,H20C), C203(H20D,H20E,H20F),
 N205(H20I,H20J,H20K), C220(H22A,H22B,H22C), C221(H22D,H22E,H22F), C301(H30A,
 H30B,H30C), C303(H30D,H30E,H30F), N305(H30I,H30J,H30K), C320(H32A,H32B,H32C),
 C321(H32D,H32E,H32F), C401(H40A,H40B,H40C), C403(H40D,H40E,H40F), N405(H40I,
 H40J,H40K), C420(H42A,H42B,H42C), C421(H42D,H42E,H42F)
;