Nonribosomal biosynthesis of backbone-modified peptides
David L. Niquille; Douglas A. Hansen; Takahiro Mori; David Fercher; Hajo Kries; Donald Hilvert; Nature Chemistry 10 (2018) 282–287; doi:10.1038/nchem.2891

data_1551399
_publ_section_title
;
 Nonribosomal biosynthesis of backbone-modified peptides
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              282
_journal_page_last               287
_journal_paper_doi               10.1038/nchem.2891
_journal_volume                  10
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H16 N2 O2'
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.19770(6)
_cell_length_b                   9.65236(5)
_cell_length_c                   18.11426(9)
_cell_measurement_reflns_used    59851
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.7750
_cell_measurement_theta_min      4.8570
_cell_volume                     1258.484(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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     40.00 125.00   0.50    0.70    --   50.21  38.00 -90.00  170
  2  \w     82.00 169.00   0.50    0.70    --   94.00  46.00 -53.45  174
  3  \w     98.00 178.00   0.50    0.70    --  107.75  38.00 -90.00  160
  4  \w     98.00 178.00   0.50    0.70    --  107.75  38.00-180.00  160
  5  \w     98.00 178.00   0.50    0.70    --  107.75  38.00-120.00  160
  6  \w     98.00 178.00   0.50    0.70    --  107.75  38.00  30.00  160
  7  \w     98.00 178.00   0.50    0.70    --  107.75  38.00  90.00  160
  8  \w     98.00 178.00   0.50    0.70    --  107.75  38.00  60.00  160
  9  \w     98.00 178.00   0.50    0.70    --  107.75  38.00 120.00  160
 10  \w     98.00 178.00   0.50    0.70    --  107.75  38.00   0.00  160
 11  \w     98.00 178.00   0.50    0.70    --  107.75  38.00-150.00  160
 12  \w     85.00 173.00   0.50    0.70    --  107.75  77.00 -30.00  176
 13  \w     93.00 178.00   0.50    0.70    --  107.75  57.00 -90.00  170
 14  \w     85.00 173.00   0.50    0.70    --  107.75  77.00  90.00  176
 15  \w     93.00 178.00   0.50    0.70    --  107.75  57.00 -60.00  170
 16  \w     85.00 173.00   0.50    0.70    --  107.75  77.00  60.00  176
 17  \w     93.00 178.00   0.50    0.70    --  107.75  57.00  90.00  170
 18  \w     85.00 173.00   0.50    0.70    --  107.75  77.00 120.00  176
 19  \w     93.00 178.00   0.50    0.70    --  107.75  57.00 120.00  170
 20  \w     85.00 173.00   0.50    0.70    --  107.75  77.00  30.00  176
 21  \w     93.00 178.00   0.50    0.70    --  107.75  57.00 -30.00  170
 22  \w     85.00 173.00   0.50    0.70    --  107.75  77.00-180.00  176
 23  \w     93.00 178.00   0.50    0.70    --  107.75  57.00-180.00  170
 24  \w     85.00 173.00   0.50    0.70    --  107.75  77.00-150.00  176
 25  \w     85.00 173.00   0.50    0.70    --  107.75  77.00-120.00  176
 26  \w     85.00 173.00   0.50    0.70    --  107.75  77.00 -60.00  176
 27  \w     85.00 173.00   0.50    0.70    --  107.75  77.00 -90.00  176
 28  \w     85.00 173.00   0.50    0.70    --  107.75  77.00   0.00  176
 29  \w     93.00 178.00   0.50    0.70    --  107.75  57.00 150.00  170
 30  \w     85.00 173.00   0.50    0.70    --  107.75  77.00 150.00  176
 31  \w     39.00 111.00   0.50    0.70    --  107.75 -99.00  60.00  144
 32  \w     57.00 122.00   0.50    0.70    --   50.21-178.00 -30.00  130
 33  \w     39.00 111.00   0.50    0.70    --  107.75 -99.00 -30.00  144
 34  \w     43.00 130.00   0.50    0.70    --  107.75 -77.00-120.00  174
 35  \w     38.00 121.00   0.50    0.70    --  107.75-125.00 -90.00  166
 36  \w     39.00 111.00   0.50    0.70    --  107.75 -99.00-150.00  144
 37  \w     37.00  84.00   0.50    0.70    --  107.75 -57.00-150.00   94
 38  \w     37.00  84.00   0.50    0.70    --  107.75 -57.00 -60.00   94
 39  \w     37.00  84.00   0.50    0.70    --  107.75 -57.00 -30.00   94
 40  \w     37.00  84.00   0.50    0.70    --  107.75 -57.00  60.00   94
 41  \w     39.00 111.00   0.50    0.70    --  107.75 -99.00 150.00  144
 42  \w     37.00  84.00   0.50    0.70    --  107.75 -57.00 120.00   94
 43  \w     39.00 111.00   0.50    0.70    --  107.75 -99.00  90.00  144
 44  \w     37.00 165.00   0.50    0.70    --  107.75   0.00 150.00  256
 45  \w     50.00 140.00   0.50    0.70    --   74.00  80.00   6.23  180
 46  \w     53.00 140.00   0.50    0.70    --   74.00  74.00-147.43  174
 47  \w     40.00 127.00   0.50    0.70    --   62.00  77.00-157.94  174
 48  \w     36.00 121.00   0.50    0.70    --   50.21  57.00   0.00  170
 49  \w     40.00 125.00   0.50    0.70    --   50.21  38.00 -30.00  170
 50  \w     40.00 125.00   0.50    0.70    --   50.21  19.00 -90.00  170
 51  \w     37.00 165.00   0.50    0.70    --  107.75   0.00  90.00  256
 52  \w     40.00 125.00   0.50    0.70    --   50.21  19.00 120.00  170
 53  \w     37.00 165.00   0.50    0.70    --  107.75   0.00  30.00  256
 54  \w     37.00 165.00   0.50    0.70    --  107.75   0.00-180.00  256
 55  \w     37.00 165.00   0.50    0.70    --  107.75   0.00-150.00  256
 56  \w     37.00 165.00   0.50    0.70    --  107.75   0.00-120.00  256
 57  \w     39.00 111.00   0.50    0.70    --  107.75 -99.00 -90.00  144
 58  \w     37.00 165.00   0.50    0.70    --  107.75   0.00   0.00  256
 59  \w     37.00 165.00   0.50    0.70    --  107.75   0.00 -30.00  256
 60  \w     37.00 165.00   0.50    0.70    --  107.75   0.00  60.00  256
 61  \w     37.00 165.00   0.50    0.70    --  107.75   0.00 -60.00  256
 62  \w     37.00 165.00   0.50    0.70    --  107.75   0.00 120.00  256
 63  \w     37.00 165.00   0.50    0.70    --  107.75   0.00 -90.00  256
 64  \w     40.00 125.00   0.50    0.70    --   50.21  38.00   0.00  170
 65  \w     40.00 125.00   0.50    0.70    --   50.21  19.00  90.00  170
 66  \w     25.00 117.00   0.50    0.70    --   50.00  83.00 108.43  184
 67  \w     29.00 121.00   0.50    0.70    --   54.00  83.00 136.95  184
 68  \w     29.00 121.00   0.50    0.70    --   54.00  83.00  29.42  184
 69  \w      6.00  46.00   0.50    0.70    --   34.00  89.00 -25.94   80
 70  \w    -95.00  -9.00   0.50    0.70    --  -70.00 125.00  40.00  172
 71  \w   -125.00 -40.00   0.50    0.70    --  -50.21 -38.00-180.00  170
 72  \w   -121.00 -35.00   0.50    0.70    --  -50.21 -57.00 -60.00  172
 73  \w   -115.00 -28.00   0.50    0.70    --  -50.21 -77.00 -60.00  174
 74  \w   -121.00 -35.00   0.50    0.70    --  -50.21 -57.00-180.00  172
 75  \w   -115.00 -28.00   0.50    0.70    --  -50.21 -77.00-120.00  174
 76  \w   -120.00 -38.00   0.50    0.70    --  -50.21-178.00-180.00  164
 77  \w   -131.00 -42.00   0.50    0.70    --  -66.00 -79.00-153.88  178
 78  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00 -51.34  176
 79  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00  60.00  176
 80  \w   -136.00 -45.00   0.50    0.70    --  -70.00 -82.00 121.22  182
 81  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00   0.00  176
 82  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00 -90.00  176
 83  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00-120.00  176
 84  \w   -136.00 -49.00   0.50    0.70    --  -70.00 -74.00 -28.97  174
 85  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00  90.00  176
 86  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00 150.00  176
 87  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -78.00 163.34  176
 88  \w   -141.00 -55.00   0.50    0.70    --  -70.00 -57.00   0.00  172
 89  \w   -137.00 -50.00   0.50    0.70    --  -70.00 -71.00 -52.29  174
 90  \w   -140.00 -70.00   0.50    0.70    --  -70.00-125.00-150.00  140
 91  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00 -60.00  176
 92  \w   -139.00 -82.00   0.50    0.70    --  -70.00 -99.00 120.00  114
 93  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00 120.00  176
 94  \w   -141.00 -55.00   0.50    0.70    --  -70.00 -57.00  30.00  172
 95  \w   -138.00 -51.00   0.50    0.70    --  -70.00 -68.00 -15.26  174
 96  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00-180.00  176
 97  \w   -137.00 -49.00   0.50    0.70    --  -70.00 -72.00-110.74  176
 98  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00  30.00  176
 99  \w   -135.00 -47.00   0.50    0.70    --  -70.00 -77.00-150.00  176
100  \w   -137.00 -49.00   0.50    0.70    --  -70.00 -72.00 -52.62  176
101  \w   -136.00 -45.00   0.50    0.70    --  -70.00 -83.00 -70.25  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0154561000
_diffrn_orient_matrix_UB_12      -0.0055934000
_diffrn_orient_matrix_UB_13      -0.0847704000
_diffrn_orient_matrix_UB_21      0.0460381000
_diffrn_orient_matrix_UB_22      0.1558522000
_diffrn_orient_matrix_UB_23      -0.0015934000
_diffrn_orient_matrix_UB_31      0.2084494000
_diffrn_orient_matrix_UB_32      -0.0339774000
_diffrn_orient_matrix_UB_33      0.0066411000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            90375
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.040
_diffrn_reflns_theta_min         4.883
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1075 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0443P)^2^+0.3076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2628
_reflns_number_total             2704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nchem.2891-s4.cif
_cod_data_source_block           h070617_1_1
_cod_original_cell_volume        1258.485(14)
_cod_database_code               1551399
_chemical_oxdiff_formula         'C14 H16 N2 O2'
_diffrn_oxdiff_ac3_digest_frames
;
01118377b3a281d1d4eb6d9e2349b46fd61764233b4
;
_diffrn_oxdiff_ac3_digest_hkl
;
018b23ca53190a95dc2e4273a0573c18439900
;
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1
 0.93 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7)
;
_shelx_res_checksum              49839