#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/78/1557808.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_1557808
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-m-MA
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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             2016-04-29T13:21:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.302(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4442(12)
_cell_length_b                   7.7559(11)
_cell_length_c                   10.4879(13)
_cell_measurement_reflns_used    4870
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.54
_cell_measurement_wavelength     0.71073
_cell_volume                     652.13(16)
_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 1
_diffrn_measured_fraction_theta_max 0.988
_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      -0.124345
_diffrn_orient_matrix_UB_12      -0.00101
_diffrn_orient_matrix_UB_13      -0.038933
_diffrn_orient_matrix_UB_21      0.000964
_diffrn_orient_matrix_UB_22      0.126437
_diffrn_orient_matrix_UB_23      -0.018416
_diffrn_orient_matrix_UB_31      0.009805
_diffrn_orient_matrix_UB_32      -0.025232
_diffrn_orient_matrix_UB_33      -0.090724
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_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         27.567
_diffrn_reflns_theta_min         2.045
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.86
_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    1.28
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 848 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0421
_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)+(0.0494P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                2227
_reflns_number_total             2858
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ma0c00085_si_003.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_sg_symbol_H-M      'P 21'
_cod_database_code               1557808
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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 0.4446(2) 0.8708(2) 0.11510(17) 0.0237(5) Uani 1 1 d . . . . .
H1O H 0.372(3) 0.931(4) 0.045(2) 0.036 Uiso 1 1 calc R U . . .
C1 C 0.5457(3) 0.7600(3) 0.0635(2) 0.0189(6) Uani 1 1 d . . . . .
H1 H 0.4725 0.7027 -0.0196 0.023 Uiso 1 1 calc R U . . .
C2 C 0.6230(3) 0.6221(3) 0.1663(2) 0.0187(6) Uani 1 1 d . . . . .
O3 O 0.7041(2) 0.5035(2) 0.13696(16) 0.0212(4) Uani 1 1 d . . . . .
N4 N 0.5980(3) 0.6395(3) 0.28622(19) 0.0199(5) Uani 1 1 d . . . . .
H4 H 0.535(4) 0.730(5) 0.294(3) 0.039(9) Uiso 1 1 d . . . . .
C5 C 0.6498(3) 0.5301(4) 0.3997(2) 0.0192(6) Uani 1 1 d . . . . .
C6 C 0.7098(3) 0.3636(4) 0.3943(2) 0.0196(6) Uani 1 1 d . . . . .
H6 H 0.7176 0.3189 0.3122 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7584(3) 0.2633(3) 0.5104(2) 0.0210(6) Uani 1 1 d . . . . .
C8 C 0.7467(3) 0.3269(4) 0.6312(2) 0.0237(6) Uani 1 1 d . . . . .
H8 H 0.7802 0.2582 0.7102 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6851(3) 0.4925(4) 0.6346(2) 0.0248(6) Uani 1 1 d . . . . .
H9 H 0.6759 0.5368 0.7165 0.03 Uiso 1 1 calc R U . . .
C10 C 0.6372(3) 0.5934(3) 0.5206(2) 0.0223(6) Uani 1 1 d . . . . .
H10 H 0.5956 0.7064 0.5244 0.027 Uiso 1 1 calc R U . . .
C11 C 0.8212(3) 0.0901(4) 0.5043(2) 0.0224(6) Uani 1 1 d . . . . .
C12 C 0.8722(3) -0.0496(4) 0.4999(3) 0.0291(7) Uani 1 1 d . . . . .
H12 H 0.9135 -0.1628 0.4963 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6812(3) 0.8583(3) 0.0279(2) 0.0188(6) Uani 1 1 d . . . . .
C14 C 0.7917(3) 0.9632(4) 0.1230(3) 0.0263(7) Uani 1 1 d . . . . .
H14 H 0.7827 0.9727 0.2108 0.032 Uiso 1 1 calc R U . . .
C15 C 0.9145(4) 1.0536(4) 0.0898(3) 0.0351(8) Uani 1 1 d . . . . .
H15 H 0.9891 1.1249 0.1553 0.042 Uiso 1 1 calc R U . . .
C16 C 0.9302(3) 1.0417(4) -0.0368(3) 0.0366(8) Uani 1 1 d . . . . .
H16 H 1.015 1.1042 -0.0585 0.044 Uiso 1 1 calc R U . . .
C17 C 0.8210(4) 0.9376(4) -0.1320(3) 0.0321(7) Uani 1 1 d . . . . .
H17 H 0.8315 0.9276 -0.2193 0.039 Uiso 1 1 calc R U . . .
C18 C 0.6960(3) 0.8478(4) -0.0999(2) 0.0234(6) Uani 1 1 d . . . . .
H18 H 0.6201 0.7786 -0.1661 0.028 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 H1O 109.5 . . ?
O1 C1 C2 109.25(19) . . ?
O1 C1 C13 112.2(2) . . ?
C2 C1 C13 109.9(2) . . ?
O1 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
C13 C1 H1 108.5 . . ?
O3 C2 N4 124.5(2) . . ?
O3 C2 C1 119.7(2) . . ?
N4 C2 C1 115.8(2) . . ?
C2 N4 C5 129.0(2) . . ?
C2 N4 H4 115.9(19) . . ?
C5 N4 H4 115.1(19) . . ?
C10 C5 C6 119.6(2) . . ?
C10 C5 N4 117.5(2) . . ?
C6 C5 N4 122.8(2) . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 C11 120.0(2) . . ?
C6 C7 C11 119.3(2) . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C5 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
C12 C11 C7 179.7(3) . . ?
C11 C12 H12 180 . . ?
C18 C13 C14 118.9(2) . . ?
C18 C13 C1 120.8(2) . . ?
C14 C13 C1 120.3(2) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120 . . ?
C18 C17 H17 120 . . ?
C13 C18 C17 120.7(3) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
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 1.432(3) . ?
O1 H1O 0.93(3) . ?
C1 C2 1.514(4) . ?
C1 C13 1.516(4) . ?
C1 H1 1 . ?
C2 O3 1.242(3) . ?
C2 N4 1.346(3) . ?
N4 C5 1.414(3) . ?
N4 H4 0.90(3) . ?
C5 C10 1.395(3) . ?
C5 C6 1.395(4) . ?
C6 C7 1.393(3) . ?
C6 H6 0.95 . ?
C7 C8 1.392(3) . ?
C7 C11 1.452(4) . ?
C8 C9 1.390(4) . ?
C8 H8 0.95 . ?
C9 C10 1.379(3) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.172(4) . ?
C12 H12 0.95 . ?
C13 C18 1.387(3) . ?
C13 C14 1.394(4) . ?
C14 C15 1.383(4) . ?
C14 H14 0.95 . ?
C15 C16 1.378(4) . ?
C15 H15 0.95 . ?
C16 C17 1.386(4) . ?
C16 H16 0.95 . ?
C17 C18 1.391(4) . ?
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 H1O O3 0.93 1.9 2.746(2) 151.4 2_655
N4 H4 O1 0.90(3) 2.10(3) 2.580(3) 112(2) .
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 173.8(2) . . . . ?
C13 C1 C2 O3 -62.7(3) . . . . ?
O1 C1 C2 N4 -6.5(3) . . . . ?
C13 C1 C2 N4 116.9(2) . . . . ?
O3 C2 N4 C5 -2.4(4) . . . . ?
C1 C2 N4 C5 178.0(2) . . . . ?
C2 N4 C5 C10 167.5(2) . . . . ?
C2 N4 C5 C6 -13.2(4) . . . . ?
C10 C5 C6 C7 -0.7(4) . . . . ?
N4 C5 C6 C7 -180.0(2) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C7 C11 -179.8(2) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C11 C7 C8 C9 -179.6(2) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C5 0.1(4) . . . . ?
C6 C5 C10 C9 0.5(4) . . . . ?
N4 C5 C10 C9 179.7(2) . . . . ?
O1 C1 C13 C18 -124.7(2) . . . . ?
C2 C1 C13 C18 113.6(3) . . . . ?
O1 C1 C13 C14 54.3(3) . . . . ?
C2 C1 C13 C14 -67.5(3) . . . . ?
C18 C13 C14 C15 -0.6(4) . . . . ?
C1 C13 C14 C15 -179.5(2) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C14 C13 C18 C17 1.3(4) . . . . ?
C1 C13 C18 C17 -179.7(2) . . . . ?
C16 C17 C18 C13 -1.3(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306285
