#------------------------------------------------------------------------------
#$Date: 2019-06-28 03:15:22 +0300 (Fri, 28 Jun 2019) $
#$Revision: 216599 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/37/7123736.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7123736
loop_
_publ_author_name
'Basuyaux, Gaëtan'
'Desmarchelier, Alaric'
'Gontard, Geoffrey'
'Vanthuyne, Nicolas'
'Moussa, Jamal'
'Amouri, Hani Haniel'
'Raynal, Matthieu'
'Bouteiller, Laurent'
_publ_section_title
;
 Extra hydrogen bonding interactions by peripheral indole groups stabilize
 benzene-1,3,5-tricarboxamide helical assemblies
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03906F
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C51 H54 N6 O9'
_chemical_formula_sum            'C51 H54 N6 O9'
_chemical_formula_weight         895.00
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-04-10 deposited with the CCDC.    2019-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   19.4557(4)
_cell_length_b                   19.4557(4)
_cell_length_c                   7.0842(2)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      4.55
_cell_volume                     2322.28(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         micro-source
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25067
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.648
_diffrn_reflns_theta_min         4.545
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS : Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0325
_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/[σ²(Fo²)+(0.0554P)²+0.3398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2614
_reflns_number_total             2747
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc03906f2.cif
_cod_data_source_block           (S)-BTA_Trp-i-Pr
_cod_original_cell_volume        2322.28(12)
_cod_database_code               7123736
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.08249(9) 0.20902(8) 0.6626(2) 0.0234(3) Uani 1 1 d . .
O2 O 0.17102(10) 0.28029(10) 0.1209(3) 0.0338(4) Uani 1 1 d . .
O3 O 0.24947(10) 0.40060(9) 0.2511(3) 0.0316(4) Uani 1 1 d . .
N1 N 0.16697(10) 0.20428(10) 0.4499(3) 0.0218(4) Uani 1 1 d . .
H1A H 0.178251 0.173210 0.382429 0.026 Uiso 1 1 calc R U
N2 N 0.32324(12) 0.26512(12) 0.9696(3) 0.0328(5) Uani 1 1 d . .
H2 H 0.304159 0.237715 1.074290 0.039 Uiso 1 1 calc R U
C1 C 0.08229(12) 0.03224(12) 0.5443(3) 0.0183(4) Uani 1 1 d . .
H1B H 0.138213 0.054014 0.544075 0.022 Uiso 1 1 calc R U
C2 C 0.05041(12) 0.08219(12) 0.5445(3) 0.0177(4) Uani 1 1 d . .
C3 C 0.10179(12) 0.17091(12) 0.5561(3) 0.0186(4) Uani 1 1 d . .
C4 C 0.22058(13) 0.28985(12) 0.4399(3) 0.0238(5) Uani 1 1 d . .
H4 H 0.205380 0.315095 0.542230 0.029 Uiso 1 1 calc R U
C5 C 0.20968(13) 0.32108(13) 0.2504(4) 0.0248(5) Uani 1 1 d . .
C6 C 0.24000(16) 0.44118(15) 0.0865(4) 0.0354(6) Uani 1 1 d . .
H6 H 0.183216 0.412409 0.045434 0.043 Uiso 1 1 calc R U
C7 C 0.2916(2) 0.44264(19) -0.0742(5) 0.0492(8) Uani 1 1 d . .
H7A H 0.284720 0.469809 -0.182783 0.074 Uiso 1 1 calc R U
H7B H 0.347326 0.470925 -0.034505 0.074 Uiso 1 1 calc R U
H7C H 0.276299 0.388128 -0.109546 0.074 Uiso 1 1 calc R U
C8 C 0.26153(18) 0.52312(15) 0.1553(5) 0.0461(7) Uani 1 1 d . .
H8A H 0.256371 0.553396 0.051186 0.069 Uiso 1 1 calc R U
H8B H 0.225779 0.518500 0.258164 0.069 Uiso 1 1 calc R U
H8C H 0.316405 0.550556 0.201190 0.069 Uiso 1 1 calc R U
C9 C 0.30757(13) 0.31250(15) 0.4715(4) 0.0293(5) Uani 1 1 d . .
H9A H 0.319369 0.277967 0.391471 0.035 Uiso 1 1 calc R U
H9B H 0.342067 0.367855 0.428573 0.035 Uiso 1 1 calc R U
C10 C 0.32857(14) 0.30599(13) 0.6704(4) 0.0268(5) Uani 1 1 d . .
C11 C 0.28169(14) 0.25363(14) 0.8062(4) 0.0296(5) Uani 1 1 d . .
H11 H 0.227507 0.214527 0.789143 0.036 Uiso 1 1 calc R U
C12 C 0.39947(14) 0.32618(15) 0.9445(4) 0.0313(5) Uani 1 1 d . .
C13 C 0.40509(14) 0.35404(14) 0.7584(4) 0.0284(5) Uani 1 1 d . .
C14 C 0.47720(15) 0.41820(15) 0.6964(4) 0.0356(6) Uani 1 1 d . .
H14 H 0.482676 0.438050 0.571458 0.043 Uiso 1 1 calc R U
C15 C 0.54012(16) 0.45182(17) 0.8216(5) 0.0445(7) Uani 1 1 d . .
H15 H 0.588910 0.496134 0.782526 0.053 Uiso 1 1 calc R U
C16 C 0.53348(17) 0.42198(19) 1.0046(5) 0.0475(8) Uani 1 1 d . .
H16 H 0.578319 0.445458 1.085841 0.057 Uiso 1 1 calc R U
C17 C 0.46351(17) 0.35946(17) 1.0691(4) 0.0408(6) Uani 1 1 d . .
H17 H 0.458914 0.339657 1.193794 0.049 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 O3 C6 117.5(2) . .
C3 N1 C4 123.17(18) . .
C11 N2 C12 109.1(2) . .
C2 C1 C2 120.0(2) . 3
C1 C2 C1 120.0(2) . 2
C1 C2 C3 122.00(19) . .
C1 C2 C3 117.88(18) 2 .
O1 C3 N1 123.48(19) . .
O1 C3 C2 119.56(18) . .
N1 C3 C2 116.96(18) . .
N1 C4 C5 109.49(19) . .
N1 C4 C9 112.13(18) . .
C5 C4 C9 111.42(19) . .
O2 C5 O3 125.1(2) . .
O2 C5 C4 125.0(2) . .
O3 C5 C4 109.9(2) . .
O3 C6 C7 110.3(2) . .
O3 C6 C8 105.5(2) . .
C7 C6 C8 113.1(2) . .
C10 C9 C4 115.0(2) . .
C11 C10 C13 105.5(2) . .
C11 C10 C9 128.3(2) . .
C13 C10 C9 126.2(2) . .
N2 C11 C10 110.8(2) . .
N2 C12 C17 130.4(3) . .
N2 C12 C13 107.3(2) . .
C17 C12 C13 122.3(2) . .
C14 C13 C12 119.1(2) . .
C14 C13 C10 133.6(3) . .
C12 C13 C10 107.3(2) . .
C15 C14 C13 118.4(3) . .
C14 C15 C16 121.4(3) . .
C17 C16 C15 121.4(3) . .
C16 C17 C12 117.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.240(3) .
O2 C5 1.200(3) .
O3 C5 1.340(3) .
O3 C6 1.471(3) .
N1 C3 1.331(3) .
N1 C4 1.459(3) .
N2 C11 1.365(3) .
N2 C12 1.371(3) .
C1 C2 1.390(3) .
C1 C2 1.404(3) 3
C2 C3 1.503(3) .
C4 C5 1.531(4) .
C4 C9 1.537(3) .
C6 C7 1.508(4) .
C6 C8 1.512(4) .
C9 C10 1.490(4) .
C10 C11 1.366(4) .
C10 C13 1.445(3) .
C12 C17 1.394(4) .
C12 C13 1.409(4) .
C13 C14 1.403(4) .
C14 C15 1.383(4) .
C15 C16 1.400(5) .
C16 C17 1.373(4) .
