#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/78/1557806.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_1557806
loop_
_publ_author_name
'Cobos, Katherine'
'Rodríguez, Rafael'
'Domarco, Olaya'
'Fernández, Berta'
'Quiñoá, Emilio'
'Riguera, Ricardo'
'Freire, Félix'
_publ_section_title
;
 Polymeric Helical Structures à la Carte by Rational Design of Monomers
;
_journal_issue                   8
_journal_name_full               Macromolecules
_journal_page_first              3182
_journal_page_last               3193
_journal_paper_doi               10.1021/acs.macromol.0c00085
_journal_volume                  53
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_chemical_name_common            R-p-Ma
_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     dual
_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             2016-05-04T12:37:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5806(9)
_cell_length_b                   7.9701(11)
_cell_length_c                   22.102(3)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      2.72
_cell_measurement_wavelength     0.71073
_cell_volume                     1335.4(3)
_computing_cell_refinement       'SAINT V8.37A 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      -0.001273
_diffrn_orient_matrix_UB_12      -0.010224
_diffrn_orient_matrix_UB_13      0.045093
_diffrn_orient_matrix_UB_21      0.070126
_diffrn_orient_matrix_UB_22      0.105864
_diffrn_orient_matrix_UB_23      0.003354
_diffrn_orient_matrix_UB_31      -0.111725
_diffrn_orient_matrix_UB_32      0.066563
_diffrn_orient_matrix_UB_33      0.001592
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            47312
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_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         30.528
_diffrn_reflns_theta_min         2.717
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.87
_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    1.25
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1199 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     178
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0424
_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)+(0.0399P)²+0.2469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3307
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ma0c00085_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;Adding full bibliography for 1557803--1557808.cif.

 Adding full bibliography for 1557803--1557808.cif.
;
_cod_original_cell_volume        1335.3(3)
_cod_database_code               1557806
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.995
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
O1 O 0.33301(16) 0.46477(18) 0.25718(6) 0.0232(3) Uani 1 1 d . . . . .
H1A H 0.3595(15) 0.413(3) 0.2236(11) 0.035 Uiso 1 1 calc R U . . .
C1 C 0.4755(2) 0.5715(2) 0.27423(8) 0.0193(4) Uani 1 1 d . . . . .
H1 H 0.5135 0.6371 0.2379 0.023 Uiso 1 1 calc R U . . .
C2 C 0.4127(2) 0.6938(2) 0.32251(8) 0.0184(4) Uani 1 1 d . . . . .
O3 O 0.51052(16) 0.80788(16) 0.33985(5) 0.0219(3) Uani 1 1 d . . . . .
N4 N 0.24813(19) 0.6658(2) 0.34349(7) 0.0196(3) Uani 1 1 d . . . . .
H4 H 0.190(3) 0.586(3) 0.3222(10) 0.033(6) Uiso 1 1 d . . . . .
C5 C 0.1505(2) 0.7626(2) 0.38548(8) 0.0189(4) Uani 1 1 d . . . . .
C6 C 0.2281(2) 0.8704(3) 0.42715(9) 0.0238(4) Uani 1 1 d . . . . .
H6 H 0.3526 0.8844 0.4279 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1223(2) 0.9574(3) 0.46775(8) 0.0242(4) Uani 1 1 d . . . . .
H7 H 0.1753 1.0304 0.4965 0.029 Uiso 1 1 calc R U . . .
C8 C -0.0611(2) 0.9391(2) 0.46695(8) 0.0219(4) Uani 1 1 d . . . . .
C9 C -0.1369(2) 0.8291(3) 0.42534(9) 0.0248(4) Uani 1 1 d . . . . .
H9 H -0.2612 0.8144 0.4247 0.03 Uiso 1 1 calc R U . . .
C10 C -0.0326(2) 0.7414(2) 0.38508(8) 0.0231(4) Uani 1 1 d . . . . .
H10 H -0.0854 0.6664 0.357 0.028 Uiso 1 1 calc R U . . .
C11 C -0.1733(3) 1.0326(3) 0.50754(9) 0.0259(4) Uani 1 1 d . . . . .
C12 C -0.2723(3) 1.1079(3) 0.53900(10) 0.0363(5) Uani 1 1 d . . . . .
H12 H -0.3516 1.1682 0.5642 0.044 Uiso 1 1 calc R U . . .
C13 C 0.6314(2) 0.4705(2) 0.29690(8) 0.0194(4) Uani 1 1 d . . . . .
C14 C 0.6180(3) 0.3807(3) 0.35078(9) 0.0280(4) Uani 1 1 d . . . . .
H14 H 0.5146 0.3902 0.3748 0.034 Uiso 1 1 calc R U . . .
C15 C 0.7548(3) 0.2773(3) 0.36968(10) 0.0393(6) Uani 1 1 d . . . . .
H15 H 0.7444 0.216 0.4064 0.047 Uiso 1 1 calc R U . . .
C16 C 0.9060(3) 0.2634(3) 0.33509(10) 0.0414(6) Uani 1 1 d . . . . .
H16 H 0.9989 0.1916 0.3478 0.05 Uiso 1 1 calc R U . . .
C17 C 0.9224(2) 0.3534(3) 0.28228(11) 0.0360(6) Uani 1 1 d . . . . .
H17 H 1.027 0.3445 0.2589 0.043 Uiso 1 1 calc R U . . .
C18 C 0.7850(2) 0.4584(3) 0.26289(9) 0.0254(4) Uani 1 1 d . . . . .
H18 H 0.797 0.521 0.2266 0.03 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
C1 O1 H1A 109.5 . . ?
O1 C1 C13 111.19(15) . . ?
O1 C1 C2 109.31(14) . . ?
C13 C1 C2 110.64(14) . . ?
O1 C1 H1 108.5 . . ?
C13 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
O3 C2 N4 124.78(17) . . ?
O3 C2 C1 120.10(15) . . ?
N4 C2 C1 115.12(16) . . ?
C2 N4 C5 128.20(16) . . ?
C2 N4 H4 112.7(14) . . ?
C5 N4 H4 118.1(14) . . ?
C6 C5 C10 119.94(17) . . ?
C6 C5 N4 123.37(16) . . ?
C10 C5 N4 116.65(16) . . ?
C7 C6 C5 119.49(17) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 120.93(18) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 118.93(17) . . ?
C9 C8 C11 119.44(17) . . ?
C7 C8 C11 121.62(18) . . ?
C10 C9 C8 120.50(17) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 120.20(18) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
C12 C11 C8 176.7(2) . . ?
C11 C12 H12 180 . . ?
C18 C13 C14 119.16(17) . . ?
C18 C13 C1 120.80(17) . . ?
C14 C13 C1 119.94(16) . . ?
C15 C14 C13 120.54(19) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.23(19) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 119.9(2) . . ?
C13 C18 H18 120 . . ?
C17 C18 H18 120 . . ?
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
O1 C1 1.425(2) . ?
O1 H1A 0.87(2) . ?
C1 C13 1.515(2) . ?
C1 C2 1.522(2) . ?
C1 H1 1 . ?
C2 O3 1.235(2) . ?
C2 N4 1.349(2) . ?
N4 C5 1.416(2) . ?
N4 H4 0.90(2) . ?
C5 C6 1.390(3) . ?
C5 C10 1.399(2) . ?
C6 C7 1.389(3) . ?
C6 H6 0.95 . ?
C7 C8 1.398(3) . ?
C7 H7 0.95 . ?
C8 C9 1.394(3) . ?
C8 C11 1.444(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.186(3) . ?
C12 H12 0.95 . ?
C13 C18 1.390(2) . ?
C13 C14 1.393(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.95 . ?
C15 C16 1.383(3) . ?
C15 H15 0.95 . ?
C16 C17 1.376(4) . ?
C16 H16 0.95 . ?
C17 C18 1.403(3) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O3 0.87 1.91 2.7514(19) 162.1 3_645
N4 H4 O1 0.90(2) 2.04(2) 2.573(2) 116.2(18) .
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
O1 C1 C2 O3 -173.40(15) . . . . ?
C13 C1 C2 O3 63.8(2) . . . . ?
O1 C1 C2 N4 6.9(2) . . . . ?
C13 C1 C2 N4 -115.90(17) . . . . ?
O3 C2 N4 C5 4.2(3) . . . . ?
C1 C2 N4 C5 -176.13(16) . . . . ?
C2 N4 C5 C6 -22.6(3) . . . . ?
C2 N4 C5 C10 159.54(18) . . . . ?
C10 C5 C6 C7 -0.6(3) . . . . ?
N4 C5 C6 C7 -178.36(17) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C6 C7 C8 C11 -177.99(18) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C11 C8 C9 C10 178.41(18) . . . . ?
C8 C9 C10 C5 -0.3(3) . . . . ?
C6 C5 C10 C9 1.0(3) . . . . ?
N4 C5 C10 C9 178.91(17) . . . . ?
O1 C1 C13 C18 109.33(19) . . . . ?
C2 C1 C13 C18 -128.99(18) . . . . ?
O1 C1 C13 C14 -67.0(2) . . . . ?
C2 C1 C13 C14 54.7(2) . . . . ?
C18 C13 C14 C15 -1.4(3) . . . . ?
C1 C13 C14 C15 174.95(19) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C14 C13 C18 C17 1.5(3) . . . . ?
C1 C13 C18 C17 -174.84(17) . . . . ?
C16 C17 C18 C13 -0.5(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306283
