Carbonylation as a novel method for the assembly of pyrazine based oligoamide alpha-helix mimetics.
Van Mileghem, Seger; Egle, Brecht; Gilles, Philippe; Veryser, Cedrick; Van Meervelt, Luc; De Borggraeve, Wim M.; Organic & biomolecular chemistry 15 (2017) 373–378; doi:10.1039/c6ob02358d

data_7155397
_publ_section_title
;
 Carbonylation as a novel method for the assembly of pyrazine based
 oligoamide alpha-helix mimetics.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              373
_journal_page_last               378
_journal_paper_doi               10.1039/c6ob02358d
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C19 H26 N6 O5, H2 O'
_chemical_formula_sum            'C19 H28 N6 O6'
_chemical_formula_weight         436.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-10-27 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7469(6)
_cell_length_b                   8.5054(3)
_cell_length_c                   28.7562(10)
_cell_measurement_reflns_used    9644
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      28.2800
_cell_measurement_theta_min      2.9930
_cell_volume                     4340.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_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    -20.00  25.00   1.00   30.00    --  -16.84 -99.00-150.00   45
  2  \w    -50.00  40.00   1.00   30.00    --   18.87 -57.00-150.00   90
  3  \w    -11.00  89.00   1.00   30.00    --   18.87  77.00 -30.00  100
  4  \w    -42.00  56.00   1.00   30.00    --  -16.84  38.00  30.00   98
  5  \w     35.00  60.00   1.00   30.00    --   18.87 178.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0367968000
_diffrn_orient_matrix_UB_12      0.0159067000
_diffrn_orient_matrix_UB_13      -0.0083520000
_diffrn_orient_matrix_UB_21      0.0121099000
_diffrn_orient_matrix_UB_22      -0.0159956000
_diffrn_orient_matrix_UB_23      -0.0230420000
_diffrn_orient_matrix_UB_31      -0.0097162000
_diffrn_orient_matrix_UB_32      -0.0802807000
_diffrn_orient_matrix_UB_33      0.0029364000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            28743
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.748
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.336
_exptl_crystal_description       needle
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0857P)^2^+3.1025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3619
_reflns_number_total             4434
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02358d2.cif
_cod_data_source_block           wdb1003
_cod_depositor_comments
'Adding full bibliography for 7155396--7155398.cif.'
_cod_database_code               7155397
_chemical_oxdiff_formula         'C18 H24 N6 O5'
_chemical_oxdiff_usercomment     PG20
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.951
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O31(H31A,H31B)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C27(H27)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C26(H26A,H26B)
2.d Aromatic/amide H refined with riding coordinates:
 C5(H5), N16(H16), C23(H23)
2.e X=CH2 refined with riding coordinates:
 N30(H30A,H30B)
2.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id PG20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.677