Optimizing side chains for crystal growth from water: a case study of aromatic amide foldamers
Hu, Xiaobo; Dawson, Simon J.; Mandal, Pradeep K.; de Hatten, Xavier; Baptiste, Benoit; Huc, Ivan; Chem. Sci. 8 (2017) 3741–; doi:10.1039/C7SC00430C

data_1545533
_publ_section_title
;
 Optimizing side chains for crystal growth from water: a case study of
 aromatic amide foldamers
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3741
_journal_paper_doi               10.1039/C7SC00430C
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C56 H53.25 N8 O16.25'
_chemical_formula_sum            'C56.5 H55.25 N8 O17.25'
_chemical_formula_weight         1122.33
_chemical_properties_physical    ', Air-sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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
_audit_creation_date             2017-01-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-01-06 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                69.40(3)
_cell_angle_beta                 84.50(3)
_cell_angle_gamma                85.66(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4720(15)
_cell_length_b                   20.571(4)
_cell_length_c                   24.604(5)
_cell_measurement_reflns_used    7913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.070
_cell_measurement_theta_min      24.070
_cell_volume                     3520.1(14)
_computing_cell_refinement       'XDS (W. Kabsch, 2010)'
_computing_data_reduction        'XDS (W. Kabsch, 2010)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'ADSC Quantum Q315r'
_diffrn_measurement_method       'phi scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.77492
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.920
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28541
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        24.070
_diffrn_reflns_theta_max         24.070
_diffrn_reflns_theta_min         0.967
_diffrn_source                   'ESRF ID29'
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_description       needles
_exptl_crystal_F_000             1176
_exptl_crystal_recrystallization_method 'hanging drop vapor diffusion'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.491
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.643
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     728
_refine_ls_number_reflns         7913
_refine_ls_number_restraints     166
_refine_ls_restrained_S_all      1.661
_refine_ls_R_factor_all          0.1630
_refine_ls_R_factor_gt           0.1300
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3808
_refine_ls_wR_factor_ref         0.4082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5206
_reflns_number_total             7913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc00430c2.cif
_cod_data_source_block           q4-diol_sq_sq_sq
_cod_depositor_comments
'Adding full bibliography for 1545533--1545536.cif.'
_cod_original_cell_volume        3520.0(14)
_cod_original_formula_sum        'C56.50 H55.25 N8 O17.25'
_cod_database_code               1545533
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C53-C3
 1.54 with sigma of 0.02
 C38-C35
 1.54 with sigma of 0.02
 C36-C35
 1.54 with sigma of 0.02
 C01W-C01R
 1.54 with sigma of 0.02
 C35-C34
 1.54 with sigma of 0.02
 C53-C52
 1.54 with sigma of 0.02
 C21-C20
 1.54 with sigma of 0.02
 O17-C3
 1.24 with sigma of 0.02
 O01H-C01U = O020-C01X
 1.24 with sigma of 0.02
 O37-C36
 1.24 with sigma of 0.02
 O2AA-C38
 1.24 with sigma of 0.02
 O2BA-C54
 1.24 with sigma of 0.02
 C54-C53
 1.54 with sigma of 0.02
 C01W-C01U
 1.54 with sigma of 0.02
3. Rigid bond restraints
 C52, C53, C54, C3, O17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O01H, C01U, C01W, C01X, O020
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, O8, C50, C38B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C35 \\sim C36 \\sim O37 \\sim C38: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
O01H \\sim C01U \\sim C01W \\sim C01X \\sim O020: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
O56 \\sim C55 \\sim C21 \\sim C22 \\sim O23: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(O23) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C55)
\\sim Ueq, Uanis(O56) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C35) \\sim Ueq, : with sigma of 0.1 and sigma for terminal atoms of 0.2
: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C52) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Rigid body (RIGU) restrains
 O2BA, C54, H3C, O17, C53
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C55, O56, C20, C21, O23, C22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C52, C53, C54, C3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C53, C54, C3, O17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O17, C3, C53, C54, O2BA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C54(0.5) H54A(0.5) H54B(0.5) O56(0.5) H56(0.5) O37(0.5) H37(0.5)
 C51(0.5) H51A(0.5) H51B(0.5) H51C(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5)
 C3(0.5) H3A(0.5) H3C(0.5) O17(0.5) H17(0.5) O2AA(0.5) H2AA(0.5) O2BA(0.25)
 H2BA(0.25)
7.a Ternary CH refined with riding coordinates:
 C53(H53), C01W(H01W), C21(H21)
7.b Secondary CH2 refined with riding coordinates:
 C52(H52A,H52B), C54(H54A,H54B), C55(H55A,H55B), C01R(H01A,H01B), C01U(H01C,
 H01D), C01X(H01E,H01F), C20(H20A,H20B), C22(H22A,H22B), C34(H34A,H34B),
 C36(H36A,H36B), C38(H38A,H38B), C3(H3A,H3C)
7.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2B(H2B), C3B(H3B), C4B(H4B), N5(H5), N7(H7), C9B(H9B), C13B(H13B),
 C12B(H12B), C14B(H14B), C19B(H19B), C22B(H22C), C23B(H23B), C24B(H24B),
 C29B(H29B), C32B(H32B), C33B(H33B), C34B(H34C), C39B(H39B)
7.d Tetrahedral OH refined with riding coordinates:
 O56(H56), O01H(H01H), O020(H020), O23(H23), O37(H37), O17(H17), O2AA(H2AA),
 O2BA(H2BA)
7.e Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              3812
_shelx_hkl_checksum              82217
_shelx_fab_checksum              37801
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'