Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues.
Wauters, I.; Goossens, H.; Delbeke, E.; Muylaert, K.; Roman, B. I.; Van Hecke, K.; Van Speybroeck, V.; Stevens, C. V.; The Journal of organic chemistry 80 (2015) 8046–8054; doi:10.1021/acs.joc.5b01161

data_4031331
_publ_section_title
;
 Beyond the Diketopiperazine Family with Alternatively Bridged
 Brevianamide F Analogues.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8046
_journal_page_last               8054
_journal_paper_doi               10.1021/acs.joc.5b01161
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H16 Cl N3 O'
_chemical_formula_sum            'C16 H16 Cl N3 O'
_chemical_formula_weight         301.77
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-11-28
_audit_creation_method
;
  Olex2 1.2
  (compiled Nov  5 2012 18:22:26, GUI svn.r4372)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.20516(13)
_cell_length_b                   10.1306(2)
_cell_length_c                   19.4721(3)
_cell_measurement_reflns_used    4345
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.8513
_cell_measurement_theta_min      4.3605
_cell_volume                     1421.32(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9946
_diffrn_measured_fraction_theta_max 0.9946
_diffrn_measurement_details
;
  1 omega  -53.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   48.0000  122.0000 82

  2 omega  -46.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   48.0000   26.0000 37

  3 omega   40.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -48.0000  -26.0000 26

  4 omega   84.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   48.0000 -153.0000 86

  5 omega   43.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -48.0000 -122.0000 26

  6 omega   83.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   48.0000  -57.0000 95

  7 omega   50.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798 -125.0000 -180.0000 46

  8 omega -119.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -120.0000 35

  9 omega -125.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  150.0000 44

 10 omega -125.00  -98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  120.0000 27

 11 omega   34.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -90.0000 29

 12 omega   34.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000   30.0000 36

 13 omega   37.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000   90.0000 65

 14 omega   34.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -60.0000 53

 15 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000   60.0000 26

 16 omega   48.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000 -180.0000 43
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0679083000
_diffrn_orient_matrix_UB_12      0.0599246000
_diffrn_orient_matrix_UB_13      -0.0682526000
_diffrn_orient_matrix_UB_21      0.1623681000
_diffrn_orient_matrix_UB_22      -0.0668730000
_diffrn_orient_matrix_UB_23      -0.0380010000
_diffrn_orient_matrix_UB_31      -0.1213565000
_diffrn_orient_matrix_UB_32      -0.1227349000
_diffrn_orient_matrix_UB_33      -0.0125754000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6527
_diffrn_reflns_theta_full        72.02
_diffrn_reflns_theta_max         72.02
_diffrn_reflns_theta_min         4.92
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.395
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
   model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2609
_exptl_crystal_size_mid          0.1869
_exptl_crystal_size_min          0.0724
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.1506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0716
_reflns_number_gt                2637
_reflns_number_total             2728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01161_si_001.cif
_cod_data_source_block           cs001
_cod_depositor_comments          'Adding full bibliography for 4031331.cif.'
_cod_database_code               4031331
_chemical_oxdiff_formula         'C16 H17 N3 O1 Cl1'
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H5 of C5, H8 of C8, H13 of C13, H11 of C11, {H15A,H15B} of C15, {H4A,H4B}
  of C4, H9 of C9, {H14A,H14B} of C14, {H16A,H16B} of C16, H10 of C10
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.01
 N2-H2
 0.88 with sigma of 0.01
3.a Ternary CH refined with riding coordinates and stretchable bonds:
 C5(H5), C13(H13)
3.b Secondary CH2 refined with riding coordinates and stretchable bonds:
 C4(H4A,H4B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates and stretchable bonds:
 C8(H8), C9(H9), C10(H10), C11(H11)
;