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_1545534
_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
'C172 H112 Ca1.5 N32 O61 S8, Ca0.5 O3.5, 46.5(O)'
_chemical_formula_sum            'C172 H112 Ca2 N32 O111 S8'
_chemical_formula_weight         4739.57
_chemical_properties_physical    ', Air-sensitive'
_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
_audit_creation_date             2016-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2016-12-09 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.407(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.1155(11)
_cell_length_b                   45.9981(11)
_cell_length_c                   33.3135(14)
_cell_measurement_reflns_used    20891
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      44.6340
_cell_measurement_theta_min      2.4810
_cell_volume                     49307(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'SUPERFLIP (Palatinus, 2007)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            121998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        44.726
_diffrn_reflns_theta_max         44.726
_diffrn_reflns_theta_min         2.381
_diffrn_source                   'Rigaku FRX'
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       prism
_exptl_crystal_F_000             19392
_exptl_crystal_recrystallization_method 'Hanging drop vapor diffusion'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.000003(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.480
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2558
_refine_ls_number_reflns         19582
_refine_ls_number_restraints     551
_refine_ls_restrained_S_all      1.462
_refine_ls_R_factor_all          0.2003
_refine_ls_R_factor_gt           0.1324
_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          0.3635
_refine_ls_wR_factor_ref         0.4119
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10778
_reflns_number_total             19582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc00430c2.cif
_cod_data_source_block           h190
_cod_depositor_comments
'Adding full bibliography for 1545533--1545536.cif.'
_cod_database_code               1545534
_exptl_absorpt_special_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C1B, C2B, C3B, C4B, C5B, C6B, N1B, C7B, C8B, C9B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N4B, C28B, C29B, C30B, C31B, C32B, C33B, C34B, C35B, C36B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C37B, C38B, C39B, C40B, C41B, C42B, N5B, C43B, C44B, C45B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C46B, C47B, C48B, C49B, C50B, C51B, N6B, C52B, C53B, C54B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N7B, C55B, C56B, C57B, C58B, C59B, C60B, C61B, C62B, C63B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N8B, C64B, C65B, C66B, C67B, C68B, C69B, C70B, C71B, C72B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C64E, C65E, C66E, C67E, C68E, C69E, N8E, C70E, C71E, C72E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C46E, C47E, C48E, C49E, C50E, C51E, N6E, C52E, C53E, C54E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C19E, C20E, C21E, C22E, C23E, C24E, N3E, C25E, C26E, C27E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N7E, C55E, C56E, C57E, C58E, C59E, C60E, C61E, C62E, C63E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C28E, C29E, C30E, C31E, C32E, C33E, N4E, C34E, C35E, C36E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O4A \\sim N4A \\sim C4A: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
O9D \\sim O10D \\sim C9D: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
O1B \\sim N1A \\sim C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B \\sim C6B \\sim
N1B \\sim C7B \\sim C8B \\sim C9B \\sim C4BA: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
O5D \\sim N5D \\sim C5D: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
C1E \\sim C2E \\sim C3E \\sim C4E \\sim C5E \\sim C6E \\sim N1E \\sim C7E \\sim
C8E \\sim C9E: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C10E \\sim C11E \\sim C12E \\sim C13E \\sim C14E \\sim C15E \\sim N2E \\sim
C16E \\sim C17E \\sim C18E: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
O56 \\sim O52 \\sim O2C: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1) \\sim Ueq, Uanis(O2BA) \\sim Ueq, Uanis(O4CA) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
Uanis(O8CA) \\sim Ueq, : with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Fixed Sof: Ca1G(0.75) Ca2G(0.75)
5.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1D(H1D), N2A(H2A), N2D(H2D), N3A(H3A), N3D(H3D), N4A(H4A),
 N4D(H4D), N5A(H5A), N5D(H5D), N6A(H6A), N6D(H6D), N7A(H7A), N7D(H7D), N8A(H8A),
  N8D(H8D), C2B(H2B), C3B(H3B), C4B(H4B), C8B(H8B), C2E(H2E), C3E(H3E),
 C4E(H4E), C8E(H8E), C11B(H11B), C12B(H12B), C13B(H13B), C17B(H17B), C11E(H11E),
  C12E(H12E), C13E(H13E), C17E(H17E), C20B(H20B), C21B(H21B), C22B(H22B),
 C26B(H26B), C20E(H20E), C21E(H21E), C22E(H22E), C26E(H26E), C29E(H29E),
 C30E(H30E), C31E(H31E), C35E(H35E), C29B(H29B), C30B(H30B), C31B(H31B),
 C35B(H35B), C38B(H38B), C39B(H39B), C40B(H40B), C44B(H44B), C38E(H38E),
 C39E(H39E), C40E(H40E), C44E(H44E), C47E(H47E), C48E(H48E), C49E(H49E),
 C53E(H53E), C47B(H47B), C48B(H48B), C49B(H49B), C53B(H53B), C56B(H56B),
 C56E(H56E), C57B(H57B), C57E(H57E), C58B(H58B), C58E(H58E), C62B(H62B),
 C62E(H62E), C65E(H65E), C66E(H66E), C67E(H67E), C71E(H71E), C65B(H65B),
 C66B(H66B), C67B(H67B), C71B(H71B)
5.b Tetrahedral OH refined with riding coordinates:
 O10A(H10A), O10D(H10D)
5.c Naphthalene refined as free rotating group:
 C1B(C2B,C3B,C4B,C5B,C6B,N1B,C7B,C8B,C9B), C1E(C2E,C3E,C4E,C5E,C6E,N1E,C7E,C8E,
 C9E), C10B(C11B,C12B,C13B,C14B,C15B,N2B,C16B,C17B,C18B), C10E(C11E,C12E,C13E,
 C14E,C15E,N2E,C16E,C17E,C18E), C19B(C20B,C21B,C22B,C23B,C24B,N3B,C25B,C26B,
 C27B), C19E(C20E,C21E,C22E,C23E,C24E,N3E,C25E,C26E,C27E), C28E(C29E,C30E,C31E,
 C32E,C33E,N4E,C34E,C35E,C36E), C37B(C38B,C39B,C40B,C41B,C42B,N5B,C43B,C44B,
 C45B), C46E(C47E,C48E,C49E,C50E,C51E,N6E,C52E,C53E,C54E), C64E(C65E,C66E,C67E,
 C68E,C69E,N8E,C70E,C71E,C72E)
5.d Idealised Me refined as rotating group:
 C0A(H0AA,H0AB,H0AC), C0D(H0DA,H0DB,H0DC), C4BA(H4BA,H4BB,H4BC), C8(H8C,H8F,
 H8G), C39(H39A,H39C,H39D), C84(H84A,H84B,H84C), C138(H13A,H13C,H13D),
 C142(H14A,H14B,H14C), C157(H15A,H15B,H15C), C162(H16A,H16B,H16C)
;
_shelx_res_checksum              77162
_shelx_hkl_checksum              4346
_shelx_fab_checksum              2496
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'