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_1545536
_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
'C205.5 H135.5 Ca6 N32 O78, 3.5(O), 0.25(Ca O4)'
_chemical_formula_sum            'C205.5 H135.5 Ca6.25 N32 O82.5'
_chemical_formula_weight         4623.45
_chemical_properties_physical    ', Air-sensitive'
_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   geom
_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
;
2017-01-05 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.859(7)
_cell_length_b                   29.286(6)
_cell_length_c                   51.432(10)
_cell_measurement_reflns_used    27211
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.284
_cell_measurement_theta_min      26.284
_cell_volume                     52506(18)
_computing_cell_refinement       'XDS (W. Kabsch, 2010)'
_computing_data_collection       'MXCUBE SOLEIL Proxima1'
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'DECTRIS PILATUS 6M'
_diffrn_measurement_method       'phi scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.8856
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            313219
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.284
_diffrn_reflns_theta_max         26.284
_diffrn_reflns_theta_min         1.226
_diffrn_source                   'SOLEIL, Proxima1'
_exptl_absorpt_coefficient_mu    0.383
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             19020
_exptl_crystal_recrystallization_method 'hanging drop vapor diffusion'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.841
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       0.00082(15)
_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   2.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2720
_refine_ls_number_reflns         27211
_refine_ls_number_restraints     219
_refine_ls_restrained_S_all      2.889
_refine_ls_R_factor_all          0.1603
_refine_ls_R_factor_gt           0.1568
_refine_ls_shift/su_max          0.093
_refine_ls_shift/su_mean         0.012
_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          0.5004
_refine_ls_wR_factor_ref         0.5118
_reflns_Friedel_coverage         0.000
_reflns_number_gt                25357
_reflns_number_total             27211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc00430c2.cif
_cod_data_source_block           h104_sq
_cod_depositor_comments
'Adding full bibliography for 1545533--1545536.cif.'
_cod_original_formula_sum        'C205.50 H135.50 Ca6.25 N32 O82.50'
_cod_database_code               1545536
_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
2. Restrained distances
 O3DA-C3A
 1.398 with sigma of 0.02
 C7-O3DA
 1.45 with sigma of 0.02
 C9D-C10D
 1.54 with sigma of 0.02
 C64C-C25D
 1.54 with sigma of 0.02
 C22H-C21H
 1.54 with sigma of 0.02
 C9H-C10H
 1.54 with sigma of 0.02
 C14H-C13H
 1.54 with sigma of 0.02
 O7D-C6D
 1.24 with sigma of 0.03
 O12D-C10D
 1.24 with sigma of 0.03
 C64G-C25H
 1.54 with sigma of 0.02
 C30H-C29H
 1.54 with sigma of 0.02
 C5H-C14G
 1.54 with sigma of 0.02
 C2H-C1H
 1.54 with sigma of 0.02
 C18H-C17H
 1.54 with sigma of 0.02
 O28D-C26D
 1.43 with sigma of 0.02
3. Rigid bond restraints
 O23H, O24H, C21H, C22H
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2E, O5E, O8E, N1F, C1F, C3E, C4E, C6E, C7E, C9E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N77G, C71G, C72G, C73G, C74G, C75G, C76G, C78G, C79G, C80G
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O27H, O28H, C25H, C26H
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N57G, C51G, C52G, C53G, C54G, C55G, C56G, C58G, C59G, C60G
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O8F, N8F, C8F
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N47G, C41G, C42G, C43G, C44G, C45G, C46G, C48G, C49G, C50G
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N37G, C31G, C32G, C33G, C34G, C35G, C36G, C38G, C39G, C40G
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N5B, C5B, C38C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2E, O5E, O8E, N1F, C1E, C1F, C3E, C4E, C6E, C7E, C9E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O5A, O8A, N1B, C1B, C3A, C4A, C6A, C7A, C9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C29D, C74C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O11D, O12D, C9D, C10D
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C34C \\sim C13D \\sim C14D \\sim O16D \\sim O15D: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
Uanis(O28D) \\sim Ueq, Uanis(O27D) \\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
 O5A, C3A, C4A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: Ca00(0.5) Ca0A(0.5) O38W(0.5) O1TZ(0.5) O39W(0.5) O92W(0.5)
 H60G(0.5) Ca16(0.25) O71W(0.25) O2(0.25) O0AA(0.25) C3(0.5) O4(0.25) O7(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C1D(H1DA,H1DB), C1H(H1HA,H1HB), C3A(H3AA,H3AB), C3E(H3EA,H3EB), C4A(H4AA,
 H4AB), C4E(H4EA,H4EB), C5D(H5DA,H5DB), C5H(H5HA,H5HB), C6A(H6AA,H6AB),
 C6E(H6EA,H6EB), C7A(H7AA,H7AB), C7E(H7EA,H7EB), C9A(H9AA,H9AB), C9D(H9DA,H9DB),
  C9E(H9EA,H9EB), C9H(H9HA,H9HB), C13D(H13A,H13B), C13H(H13D,H13E), C17D(H17A,
 H17B), C17H(H17C,H17D), C21D(H21A,H21B), C21H(H21C,H21D), C25D(H25A,H25B),
 C25H(H25C,H25D), C29H(H29A,H29B)
7.b Aromatic/amide H refined with riding coordinates:
 N1B(H1B), N1F(H1F), N2B(H2B), N2F(H2F), N3B(H3B), N3F(H3F), N4B(H4B),
 N4F(H4F), N5B(H5B), N5F(H5F), N6B(H6B), N6F(H6F), N7B(H7B), N7F(H7F), N8B(H8B),
  N8F(H8F), C2C(H2C), C3C(H3C), C9C(H9C), C10C(H10C), C2G(H2G), C3G(H3G),
 C9G(H9G), C10G(H10G), C12C(H12C), C13C(H13C), C19C(H19C), C20C(H20C),
 C12G(H12G), C13G(H13G), C19G(H19G), C20G(H20G), C22C(H22C), C23C(H23C),
 C29C(H29C), C30C(H30C), C22G(H22G), C23G(H23G), C29G(H29G), C30G(H30G),
 C32C(H32C), C33C(H33C), C39C(H39C), C40C(H40C), C32G(H32G), C33G(H33G),
 C39G(H39G), C40G(H40G), C42C(H42C), C43C(H43C), C49C(H49C), C50C(H50C),
 C42G(H42G), C43G(H43G), C49G(H49G), C50G(H50G), C52C(H52C), C53C(H53C),
 C59C(H59C), C60C(H60C), C52G(H52G), C53G(H53G), C59G(H59G), C60G(H60G),
 C62C(H62C), C63C(H63C), C69C(H69C), C70C(H70C), C62G(H62G), C63G(H63G),
 C69G(H69G), C70G(H70G), C72C(H72C), C73C(H73C), C79C(H79C), C80C(H80C),
 C72G(H72G), C73G(H73G), C79G(H79G), C80G(H80G)
7.c Naphthalene refined as free rotating group:
 C1C(C2C,C3C,C4C,C5C,C6C,N7C,C8C,C9C,C10C), C1G(C2G,C3G,C4G,C5G,C6G,N7G,C8G,
 C9G,C10G), C11C(C12C,C13C,C14C,C15C,C16C,N17C,C18C,C19C,C20C), C21C(C22C,C23C,
 C24C,C25C,C26C,N27C,C28C,C29C,C30C), C21G(C22G,C23G,C24G,C25G,C26G,N27G,C28G,
 C29G,C30G), C31C(C32C,C33C,C34C,C35C,C36C,N37C,C38C,C39C,C40C), C41C(C42C,C43C,
 C44C,C45C,C46C,N47C,C48C,C49C,C50C), C51C(C52C,C53C,C54C,C55C,C56C,N57C,C58C,
 C59C,C60C), C61C(C62C,C63C,C64C,C65C,C66C,N67C,C68C,C69C,C70C), C71C(C72C,C73C,
 C74C,C75C,C76C,N77C,C78C,C79C,C80C)
7.d Idealised Me refined as rotating group:
 C1E(H1EA,H1EB,H1EC), C7(H7A,H7C,H7D)
;
_shelx_res_checksum              99071
_shelx_hkl_checksum              71795
_shelx_fab_checksum              80917
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'