#------------------------------------------------------------------------------
#$Date: 2020-06-24 04:13:03 +0300 (Wed, 24 Jun 2020) $
#$Revision: 253388 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/84/1558400.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_1558400
loop_
_publ_author_name
'Fernandez, Zulema'
'Fernández, Berta'
'Quiñoá, Emilio'
'Riguera, Ricardo'
'Freire, Felix'
_publ_section_title
;
 Chiral Information Harvesting in Helical Poly(acetylene) Derivatives
 Using Oligo(p-phenyleneethynylene)s as Spacers
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02685A
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H19 N O2'
_chemical_formula_sum            'C25 H19 N O2'
_chemical_formula_weight         365.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-06-21T18:34:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-05-11 deposited with the CCDC.	2020-06-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2753(2)
_cell_length_b                   8.2287(2)
_cell_length_c                   45.0822(11)
_cell_measurement_reflns_used    7950
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.52
_cell_measurement_wavelength     0.71073
_cell_volume                     1956.97(10)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_UB_11      -0.12947
_diffrn_orient_matrix_UB_12      -0.088748
_diffrn_orient_matrix_UB_13      -0.000317
_diffrn_orient_matrix_UB_21      0.138017
_diffrn_orient_matrix_UB_22      -0.082911
_diffrn_orient_matrix_UB_23      0.001475
_diffrn_orient_matrix_UB_31      -0.011053
_diffrn_orient_matrix_UB_32      0.004253
_diffrn_orient_matrix_UB_33      0.02213
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            28768
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         1.807
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.24
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1346 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0379P)²+0.3837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0862
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3752
_reflns_number_total             4486
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02685a2.cif
_cod_data_source_block           shelx
_cod_database_code               1558400
_shelx_estimated_absorpt_t_min   0.96
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5771(4) 0.7277(2) 0.13088(4) 0.0174(4) Uani 1 1 d . . . . .
H1 H 0.731(6) 0.741(3) 0.1383(6) 0.046(8) Uiso 1 1 d . . . . .
C2 C 0.3704(4) 0.7584(2) 0.14797(4) 0.0165(4) Uani 1 1 d . . . . .
O3 O 0.1507(3) 0.74903(19) 0.13986(3) 0.0221(4) Uani 1 1 d . . . . .
C4 C 0.4303(4) 0.8044(3) 0.18021(4) 0.0191(4) Uani 1 1 d . . . . .
H4 H 0.3096 0.8912 0.1867 0.023 Uiso 1 1 calc R U . . .
O5 O 0.6823(3) 0.86173(18) 0.18428(3) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.7167(5) 1.0237(3) 0.17395(5) 0.0312(6) Uani 1 1 d . . . . .
H6A H 0.7006 1.0261 0.1523 0.047 Uiso 1 1 calc R U . . .
H6B H 0.8855 1.0623 0.1797 0.047 Uiso 1 1 calc R U . . .
H6C H 0.5875 1.0943 0.1828 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3972(4) 0.6584(3) 0.20016(4) 0.0173(4) Uani 1 1 d . . . . .
C12 C 0.5778(4) 0.5354(3) 0.20017(5) 0.0223(5) Uani 1 1 d . . . . .
H12 H 0.7179 0.541 0.187 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5543(5) 0.4045(3) 0.21940(5) 0.0281(5) Uani 1 1 d . . . . .
H13 H 0.6793 0.3214 0.2195 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3479(5) 0.3949(3) 0.23847(5) 0.0289(6) Uani 1 1 d . . . . .
H14 H 0.3316 0.3056 0.2517 0.035 Uiso 1 1 calc R U . . .
C15 C 0.1667(4) 0.5158(3) 0.23813(5) 0.0299(6) Uani 1 1 d . . . . .
H15 H 0.0244 0.5086 0.251 0.036 Uiso 1 1 calc R U . . .
C16 C 0.1906(4) 0.6475(3) 0.21919(5) 0.0239(5) Uani 1 1 d . . . . .
H16 H 0.0655 0.7305 0.2192 0.029 Uiso 1 1 calc R U . . .
C21 C 0.5714(4) 0.6792(2) 0.10070(4) 0.0156(4) Uani 1 1 d . . . . .
C22 C 0.3791(4) 0.5814(2) 0.08955(4) 0.0177(5) Uani 1 1 d . . . . .
H22 H 0.245 0.5469 0.1021 0.021 Uiso 1 1 calc R U . . .
C23 C 0.3830(4) 0.5346(3) 0.06020(4) 0.0181(4) Uani 1 1 d . . . . .
H23 H 0.2511 0.4676 0.0527 0.022 Uiso 1 1 calc R U . . .
C24 C 0.5779(4) 0.5841(2) 0.04131(4) 0.0173(4) Uani 1 1 d . . . . .
C25 C 0.7705(4) 0.6829(3) 0.05274(4) 0.0185(5) Uani 1 1 d . . . . .
H25 H 0.9043 0.718 0.0402 0.022 Uiso 1 1 calc R U . . .
C26 C 0.7674(4) 0.7296(3) 0.08215(4) 0.0179(4) Uani 1 1 d . . . . .
H26 H 0.8992 0.7964 0.0898 0.021 Uiso 1 1 calc R U . . .
C27 C 0.5812(4) 0.5306(3) 0.01097(5) 0.0192(5) Uani 1 1 d . . . . .
C28 C 0.5800(4) 0.4798(3) -0.01382(5) 0.0193(4) Uani 1 1 d . . . . .
C31 C 0.5825(4) 0.4210(2) -0.04380(4) 0.0174(4) Uani 1 1 d . . . . .
C32 C 0.3973(4) 0.3125(3) -0.05405(5) 0.0200(5) Uani 1 1 d . . . . .
H32 H 0.2656 0.2783 -0.0411 0.024 Uiso 1 1 calc R U . . .
C33 C 0.4050(4) 0.2551(3) -0.08279(5) 0.0208(5) Uani 1 1 d . . . . .
H33 H 0.2779 0.182 -0.0895 0.025 Uiso 1 1 calc R U . . .
C34 C 0.5980(4) 0.3033(3) -0.10216(4) 0.0198(5) Uani 1 1 d . . . . .
C35 C 0.7807(4) 0.4135(3) -0.09205(5) 0.0215(5) Uani 1 1 d . . . . .
H35 H 0.9112 0.4488 -0.1051 0.026 Uiso 1 1 calc R U . . .
C36 C 0.7727(4) 0.4712(3) -0.06342(5) 0.0203(5) Uani 1 1 d . . . . .
H36 H 0.8979 0.546 -0.0569 0.024 Uiso 1 1 calc R U . . .
C37 C 0.6153(5) 0.2353(3) -0.13155(5) 0.0241(5) Uani 1 1 d . . . . .
C38 C 0.6341(5) 0.1757(3) -0.15536(5) 0.0291(6) Uani 1 1 d . . . . .
H38 H 0.6492 0.1279 -0.1745 0.035 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 '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
_geom_angle_publ_flag
C2 N1 C21 125.40(18) . . ?
C2 N1 H1 119.9(18) . . ?
C21 N1 H1 114.7(18) . . ?
O3 C2 N1 125.58(19) . . ?
O3 C2 C4 119.71(18) . . ?
N1 C2 C4 114.69(17) . . ?
O5 C4 C11 107.13(17) . . ?
O5 C4 C2 113.35(16) . . ?
C11 C4 C2 110.10(17) . . ?
O5 C4 H4 108.7 . . ?
C11 C4 H4 108.7 . . ?
C2 C4 H4 108.7 . . ?
C4 O5 C6 112.78(17) . . ?
O5 C6 H6A 109.5 . . ?
O5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C11 C16 119.4(2) . . ?
C12 C11 C4 120.01(18) . . ?
C16 C11 C4 120.6(2) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120 . . ?
C14 C13 H13 120 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C22 C21 C26 119.83(18) . . ?
C22 C21 N1 121.73(18) . . ?
C26 C21 N1 118.43(18) . . ?
C23 C22 C21 119.88(19) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C25 118.65(19) . . ?
C23 C24 C27 120.0(2) . . ?
C25 C24 C27 121.3(2) . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 120.1(2) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C28 C27 C24 177.2(2) . . ?
C27 C28 C31 178.9(2) . . ?
C36 C31 C32 118.64(19) . . ?
C36 C31 C28 120.1(2) . . ?
C32 C31 C28 121.2(2) . . ?
C33 C32 C31 120.5(2) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 120.7(2) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C35 118.79(19) . . ?
C33 C34 C37 120.7(2) . . ?
C35 C34 C37 120.5(2) . . ?
C36 C35 C34 120.5(2) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C31 120.9(2) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
C38 C37 C34 178.0(2) . . ?
C37 C38 H38 180 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.359(3) . ?
N1 C21 1.418(3) . ?
N1 H1 0.88(3) . ?
C2 O3 1.218(2) . ?
C2 C4 1.535(3) . ?
C4 O5 1.422(2) . ?
C4 C11 1.511(3) . ?
C4 H4 1 . ?
O5 C6 1.423(3) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C11 C12 1.390(3) . ?
C11 C16 1.390(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.95 . ?
C13 C14 1.390(3) . ?
C13 H13 0.95 . ?
C14 C15 1.379(3) . ?
C14 H14 0.95 . ?
C15 C16 1.385(3) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C21 C22 1.389(3) . ?
C21 C26 1.393(3) . ?
C22 C23 1.378(3) . ?
C22 H22 0.95 . ?
C23 C24 1.396(3) . ?
C23 H23 0.95 . ?
C24 C25 1.400(3) . ?
C24 C27 1.437(3) . ?
C25 C26 1.381(3) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C27 C28 1.193(3) . ?
C28 C31 1.436(3) . ?
C31 C36 1.400(3) . ?
C31 C32 1.401(3) . ?
C32 C33 1.380(3) . ?
C32 H32 0.95 . ?
C33 C34 1.399(3) . ?
C33 H33 0.95 . ?
C34 C35 1.400(3) . ?
C34 C37 1.441(3) . ?
C35 C36 1.375(3) . ?
C35 H35 0.95 . ?
C36 H36 0.95 . ?
C37 C38 1.184(3) . ?
C38 H38 0.95 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 N1 C2 O3 -0.1(3) . . . . ?
C21 N1 C2 C4 178.37(18) . . . . ?
O3 C2 C4 O5 -160.76(19) . . . . ?
N1 C2 C4 O5 20.6(3) . . . . ?
O3 C2 C4 C11 79.3(2) . . . . ?
N1 C2 C4 C11 -99.3(2) . . . . ?
C11 C4 O5 C6 -162.44(17) . . . . ?
C2 C4 O5 C6 75.9(2) . . . . ?
O5 C4 C11 C12 -48.7(2) . . . . ?
C2 C4 C11 C12 75.0(2) . . . . ?
O5 C4 C11 C16 129.6(2) . . . . ?
C2 C4 C11 C16 -106.7(2) . . . . ?
C16 C11 C12 C13 -1.2(3) . . . . ?
C4 C11 C12 C13 177.13(19) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C12 C11 C16 C15 0.5(3) . . . . ?
C4 C11 C16 C15 -177.8(2) . . . . ?
C2 N1 C21 C22 -33.5(3) . . . . ?
C2 N1 C21 C26 147.5(2) . . . . ?
C26 C21 C22 C23 0.1(3) . . . . ?
N1 C21 C22 C23 -178.86(19) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C22 C23 C24 C27 178.48(19) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C27 C24 C25 C26 -178.30(19) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
N1 C21 C26 C25 179.06(19) . . . . ?
C36 C31 C32 C33 0.8(3) . . . . ?
C28 C31 C32 C33 -178.9(2) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C33 C34 C35 -1.3(3) . . . . ?
C32 C33 C34 C37 176.0(2) . . . . ?
C33 C34 C35 C36 1.1(3) . . . . ?
C37 C34 C35 C36 -176.2(2) . . . . ?
C34 C35 C36 C31 0.0(3) . . . . ?
C32 C31 C36 C35 -1.0(3) . . . . ?
C28 C31 C36 C35 178.7(2) . . . . ?
