#------------------------------------------------------------------------------
#$Date: 2017-05-05 00:48:28 +0300 (Fri, 05 May 2017) $
#$Revision: 196143 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/24/4032440.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_4032440
loop_
_publ_author_name
'Adam, Abdulselam'
'Haberhauer, Gebhard'
'Wölper, Christoph'
_publ_section_title
;
 Bio-inspired Herringbone Foldamers: Strategy for Changing the Structure
 of Helices.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4203
_journal_page_last               4215
_journal_paper_doi               10.1021/acs.joc.7b00185
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C39 H39 N9 O3'
_chemical_formula_sum            'C39 H39 N9 O3'
_chemical_formula_weight         681.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   14.2403(3)
_cell_length_b                   14.2403(3)
_cell_length_c                   32.6696(9)
_cell_measurement_reflns_used    7833
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.86
_cell_volume                     5737.4(2)
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_data_collection       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_structure_refinement  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_diffrn_ambient_temperature      200(1)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17966
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0477
_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/[σ²(Fo²)+(0.0699P)²+2.3246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                2112
_reflns_number_total             2931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00185_si_002.cif
_cod_data_source_block           hab_9ndx
_cod_depositor_comments
'Adding full bibliography for 4032437--4032440.cif.'
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               4032440
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 1.00682(8) 0.68367(8) 0.04577(4) 0.0542(3) Uani 1 1 d .
N1 N 0.82830(10) 0.56049(9) 0.04256(4) 0.0463(3) Uani 1 1 d .
H1 H 0.7795 0.4916 0.0393 0.056 Uiso 1 1 d R
N2 N 0.86440(9) 0.39031(9) 0.04418(3) 0.0393(3) Uani 1 1 d .
N3 N 1.01600(9) 0.38659(10) 0.05431(4) 0.0421(3) Uani 1 1 d .
C1 C 0.79208(12) 0.63849(12) 0.04457(5) 0.0473(4) Uani 1 1 d .
H1A H 0.8150 0.6842 0.0197 0.057 Uiso 1 1 d R
H1B H 0.8244 0.6862 0.0687 0.057 Uiso 1 1 d R
C2 C 0.93317(11) 0.58826(11) 0.04538(4) 0.0404(3) Uani 1 1 d .
C3 C 0.95087(10) 0.49536(11) 0.04806(4) 0.0397(3) Uani 1 1 d .
C4 C 1.04503(11) 0.49420(11) 0.05465(4) 0.0426(3) Uani 1 1 d .
C5 C 0.90695(10) 0.32800(11) 0.04790(4) 0.0403(3) Uani 1 1 d .
C6 C 1.15823(12) 0.58368(14) 0.06093(6) 0.0596(4) Uani 1 1 d .
H6A H 1.1887 0.5685 0.0852 0.089 Uiso 1 1 d R
H6B H 1.1585 0.6521 0.0648 0.089 Uiso 1 1 d R
H6C H 1.2021 0.5895 0.0369 0.089 Uiso 1 1 d R
C7 C 1.08569(12) 0.33980(13) 0.06114(5) 0.0484(4) Uani 1 1 d .
H7A H 1.1620 0.3966 0.0564 0.058 Uiso 1 1 d R
H7B H 1.0671 0.2815 0.0408 0.058 Uiso 1 1 d R
C8 C 1.07583(11) 0.29343(12) 0.10375(5) 0.0456(4) Uani 1 1 d .
C9 C 1.02973(17) 0.31711(17) 0.13606(6) 0.0712(5) Uani 1 1 d .
H9 H 1.0020 0.3648 0.1321 0.085 Uiso 1 1 d R
C10 C 1.0229(2) 0.2724(2) 0.17437(6) 0.0831(7) Uani 1 1 d .
H10 H 0.9903 0.2894 0.1964 0.100 Uiso 1 1 d R
C11 C 1.06271(17) 0.20421(16) 0.18072(6) 0.0710(5) Uani 1 1 d .
H11 H 1.0586 0.1739 0.2070 0.085 Uiso 1 1 d R
C12 C 1.10877(16) 0.18018(15) 0.14866(7) 0.0693(5) Uani 1 1 d .
H12 H 1.1363 0.1323 0.1527 0.083 Uiso 1 1 d R
C13 C 1.11575(14) 0.22448(14) 0.11047(6) 0.0600(4) Uani 1 1 d .
H13 H 1.1485 0.2073 0.0886 0.072 Uiso 1 1 d R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_3
C2 N1 C1 122.93(12) .
C5 N2 C3 105.11(11) .
C5 N3 C4 107.44(11) .
C5 N3 C7 124.73(12) .
C4 N3 C7 127.79(12) .
N1 C1 C5 108.48(11) 2_655
O1 C2 N1 122.19(13) .
O1 C2 C3 123.90(12) .
N1 C2 C3 113.91(11) .
C4 C3 N2 110.38(12) .
C4 C3 C2 129.20(12) .
N2 C3 C2 120.42(11) .
C3 C4 N3 105.22(11) .
C3 C4 C6 131.41(14) .
N3 C4 C6 123.37(13) .
N2 C5 N3 111.85(12) .
N2 C5 C1 125.17(11) 3_665
N3 C5 C1 122.97(12) 3_665
N3 C7 C8 113.70(12) .
C9 C8 C13 118.17(16) .
C9 C8 C7 123.42(14) .
C13 C8 C7 118.41(14) .
C8 C9 C10 120.95(18) .
C11 C10 C9 120.44(19) .
C10 C11 C12 118.95(18) .
C11 C12 C13 120.83(18) .
C8 C13 C12 120.65(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.2333(16) .
N1 C2 1.3434(18) .
N1 C1 1.4411(18) .
N2 C5 1.3063(17) .
N2 C3 1.3886(17) .
N3 C5 1.3623(17) .
N3 C4 1.3732(19) .
N3 C7 1.4628(18) .
C1 C5 1.485(2) 2_655
C2 C3 1.468(2) .
C3 C4 1.3664(19) .
C4 C6 1.487(2) .
C5 C1 1.485(2) 3_665
C7 C8 1.517(2) .
C8 C9 1.371(2) .
C8 C13 1.376(2) .
C9 C10 1.385(3) .
C10 C11 1.363(3) .
C11 C12 1.367(3) .
C12 C13 1.379(3) .
