Design, synthesis and conformational analyses of bifacial benzamide based foldamers
Rodriguez-Marin, Silvia; Murphy, Natasha S.; Shepherd, Helena J.; Wilson, Andrew J.; RSC Adv. 5 (2015) 104187–; doi:10.1039/C5RA20451H

data_7223435
_publ_section_title
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 Design, synthesis and conformational analyses of bifacial benzamide based
 foldamers
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_journal_issue                   126
_journal_name_full               'RSC Adv.'
_journal_page_first              104187
_journal_paper_doi               10.1039/C5RA20451H
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C26 H36 N2 O6'
_chemical_formula_sum            'C26 H36 N2 O6'
_chemical_formula_weight         472.57
_chemical_name_systematic
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 4-(4-amino-2,5-diisobutoxyamido)-3-isobutoxybenzoic acid 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-25
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_audit_update_record
;
2015-09-22 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.877(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.224(3)
_cell_length_b                   16.806(2)
_cell_length_c                   15.8146(19)
_cell_measurement_reflns_used    6077
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.42
_cell_volume                     5401.2(12)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19204
_diffrn_reflns_theta_full        26.13
_diffrn_reflns_theta_max         26.13
_diffrn_reflns_theta_min         2.37
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0501 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.9317.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.038
_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     332
_refine_ls_number_reflns         5305
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+2.3585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                4102
_reflns_number_total             5305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra20451h2.cif
_cod_data_source_block           nm6_551_0m
_cod_original_cell_volume        5401.0(11)
_cod_database_code               7223435
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  H7A of C7, H15 of C15, H9 of C9, H4A of C4, H18 of C18, H3 of C3, {H8A,H8B}
  of C8, H7 of N7, {H19A,H19B} of C19, {H23A,H23B} of C23, H20 of C20, {H24,
  H24A} of C24
 At 1.5 times of:
  H4 of O4, {H26D,H26E,H26F} of C26A, {H10A,H10B,H10C} of C10, {H26A,H26B,
  H26C} of C26, {H22A,H22B,H22C} of C22, {H25A,H25B,H25C} of C25, {H11A,H11B,
  H11C} of C11, {H21A,H21B,H21C} of C21
2. Restrained distances
 C26A-C24 ~ C26-C24
 with sigma of 0.02
3. Restrained planarity
 H9B, N9, H9A, C16
 with sigma of 0.001
4. Others
 Fixed Sof: H24(0.75) H24A(0.25) C26(0.75) H26A(0.75) H26B(0.75) H26C(0.75)
 C26A(0.25) H26D(0.25) H26E(0.25) H26F(0.25)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C20(H20), C24(H24), C24(H24A)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C23(H23A,H23B), C19(H19A,H19B)
5.c Aromatic/amide H refined with riding coordinates:
 N7(H7), C4(H4A), C18(H18), C3(H3), C7(H7A), C15(H15)
5.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C11(H11A,H11B,H11C), C22(H22A,H22B,
 H22C), C26(H26A,H26B,H26C), C10(H10A,H10B,H10C), C26A(H26D,H26E,H26F)
5.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
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