#------------------------------------------------------------------------------
#$Date: 2021-03-09 00:49:28 +0200 (Tue, 09 Mar 2021) $
#$Revision: 262889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518542.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_4518542
loop_
_publ_author_name
'Liang, Juncong'
'Hao, Aiyou'
'Xing, Pengyao'
'Zhao, Yanli'
_publ_section_title
;
 Inverse Evolution of Helicity from the Molecular to the Macroscopic Level
 Based on N-Terminal Aromatic Amino Acids
;
_journal_name_full               'ACS Nano'
_journal_paper_doi               10.1021/acsnano.0c10876
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H17 N O6'
_chemical_formula_sum            'C19 H17 N O6'
_chemical_formula_weight         355.33
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.621(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6539(2)
_cell_length_b                   7.8453(2)
_cell_length_c                   13.4413(4)
_cell_measurement_reflns_used    6169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9580
_cell_measurement_theta_min      3.4230
_cell_volume                     874.43(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -37.00 -12.00   1.00    0.10    --  -48.45   4.00 -30.00   25
  2  ω   -119.00 -61.00   1.00    0.10    --  -48.45  -4.00 151.00   58
  3  ω     25.00  66.00   1.00    0.10    --   48.45   4.00 -30.00   41
  4  ω   -104.00 -72.00   1.00    0.40    --  -86.25   4.00 -30.00   32
  5  ω     41.00  87.00   1.00    0.40    --  106.49  -4.00 151.00   46
  6  ω    105.00 140.00   1.00    0.40    --  106.49   4.00 -30.00   35
  7  ω    -69.00 -36.00   1.00    0.10    --  -48.45 -19.00   0.00   33
  8  ω    -74.00 -44.00   1.00    0.10    --  -48.45 -29.00  92.81   30
  9  ω    -52.00 -26.00   1.00    0.10    --  -48.45 -77.00 150.00   26
 10  ω    -55.00 -28.00   1.00    0.10    --  -48.45 -77.00  30.00   27
 11  ω    -53.00 -27.00   1.00    0.10    --  -48.45 -77.00 -90.00   26
 12  ω    -53.00 -28.00   1.00    0.10    --  -48.45 -77.00  60.00   25
 13  ω    -51.00 -26.00   1.00    0.10    --  -48.45 -77.00 120.00   25
 14  ω    -54.00 -26.00   1.00    0.10    --  -48.45 -77.00-180.00   28
 15  ω     43.00  69.00   1.00    0.10    --   48.45  38.00  60.00   26
 16  ω     38.00  72.00   1.00    0.10    --   48.45  38.00   0.00   34
 17  ω     37.00  71.00   1.00    0.10    --   48.45  57.00 -30.00   34
 18  ω    -21.00  61.00   1.00    0.10    --   48.45 -38.00   0.00   82
 19  ω     41.00  83.00   1.00    0.10    --   48.45  38.00  90.00   42
 20  ω    -99.00 -65.00   1.00    0.40    --  -86.25 -72.00  72.73   34
 21  ω    -89.00 -63.00   1.00    0.40    --  -86.25 -77.00   0.00   26
 22  ω    -88.00 -63.00   1.00    0.40    --  -86.25 -77.00  30.00   25
 23  ω    -96.00 -66.00   1.00    0.40    --  -86.25 -72.00  63.75   30
 24  ω   -155.00-130.00   1.00    0.40    --  -86.25 -77.00  30.00   25
 25  ω    -86.00 -61.00   1.00    0.40    --  -86.25 -83.00   1.17   25
 26  ω    -91.00 -65.00   1.00    0.40    --  -86.25 -75.00 -43.90   26
 27  ω    -88.00 -63.00   1.00    0.40    --  -86.25 -77.00 120.00   25
 28  ω   -145.00 -93.00   1.00    0.40    --  -86.25 -77.00 120.00   52
 29  ω    -92.00 -66.00   1.00    0.40    --  -86.25 -77.00 150.00   26
 30  ω   -159.00-102.00   1.00    0.40    --  -86.25 -83.00   1.17   57
 31  ω    -91.00 -65.00   1.00    0.40    --  -86.25 -73.00  13.29   26
 32  ω   -101.00 -64.00   1.00    0.40    --  -86.25 -77.00-180.00   37
 33  ω    -96.00 -64.00   1.00    0.40    --  -86.25 -82.00  55.48   32
 34  ω    -87.00 -62.00   1.00    0.40    --  -86.25 -80.00  56.27   25
 35  ω   -105.00 -65.00   1.00    0.40    --  -86.25 -72.00  55.26   40
 36  ω    -98.00 -66.00   1.00    0.40    --  -86.25 -73.00  31.32   32
 37  ω    -92.00 -65.00   1.00    0.40    --  -86.25 -77.00  90.00   27
 38  ω   -155.00 -63.00   1.00    0.40    --  -86.25 -81.00 106.14   92
 39  ω    -90.00 -65.00   1.00    0.40    --  -86.25 -77.00  60.00   25
 40  ω    -89.00 -64.00   1.00    0.40    --  -86.25 -77.00 -30.00   25
 41  ω     34.00 121.00   1.00    0.40    --  106.49 -57.00 -30.00   87
 42  ω    110.00 175.00   1.00    0.40    --  106.49  57.00   0.00   65
 43  ω     41.00 108.00   1.00    0.40    --  106.49-125.00 150.00   67
 44  ω     93.00 147.00   1.00    0.40    --  106.49  38.00 150.00   54
 45  ω     84.00 109.00   1.00    0.40    --  106.49 -99.00-180.00   25
 46  ω    130.00 156.00   1.00    0.40    --  106.49  38.00   0.00   26
 47  ω     34.00  73.00   1.00    0.40    --  106.49 -99.00-180.00   39
 48  ω     76.00 104.00   1.00    0.40    --  106.49 -99.00 -30.00   28
 49  ω     34.00  67.00   1.00    0.40    --  106.49 -99.00 -30.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1417590000
_diffrn_orient_matrix_UB_12      0.0051986000
_diffrn_orient_matrix_UB_13      -0.1001657000
_diffrn_orient_matrix_UB_21      -0.1198274000
_diffrn_orient_matrix_UB_22      0.0093003000
_diffrn_orient_matrix_UB_23      0.0653216000
_diffrn_orient_matrix_UB_31      0.0095522000
_diffrn_orient_matrix_UB_32      0.1960666000
_diffrn_orient_matrix_UB_33      -0.0004194000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10596
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.033
_diffrn_reflns_theta_min         3.432
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.28(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3004
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0430
_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)+(0.0645P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                2625
_reflns_number_total             3004
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nn0c10876_si_002.cif
_cod_data_source_block           200117c
_cod_database_code               4518542
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CNO
_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.
;
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.959
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.132
_oxdiff_exptl_absorpt_empirical_full_min 0.482
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 0.6020(2) 0.4266(3) 0.73680(16) 0.0418(6) Uani 1 1 d . . . . .
O2 O 0.8553(2) 0.5225(3) 0.80533(17) 0.0433(6) Uani 1 1 d . . . . .
O3 O 0.9700(3) 0.2988(4) 1.13720(19) 0.0547(7) Uani 1 1 d . . . . .
H3 H 1.0073 0.2034 1.1534 0.082 Uiso 1 1 calc GR . . . .
O4 O 0.8217(3) 0.1642(3) 0.9957(2) 0.0524(7) Uani 1 1 d . . . . .
O5 O 0.8398(3) 0.8253(4) 1.0333(3) 0.0695(9) Uani 1 1 d . . . . .
H5 H 0.8219 0.9273 1.0227 0.104 Uiso 1 1 calc GR . . . .
O6 O 0.6031(4) 0.8348(4) 1.0606(3) 0.0876(11) Uani 1 1 d . . . . .
N1 N 0.6897(3) 0.4615(4) 0.90598(19) 0.0356(6) Uani 1 1 d . . . . .
H1 H 0.5904 0.4473 0.9041 0.043 Uiso 1 1 calc R . . . .
C1 C 0.7264(3) 0.4746(4) 0.8157(2) 0.0320(6) Uani 1 1 d . . . . .
C2 C 0.8648(3) 0.2930(4) 1.0453(2) 0.0351(7) Uani 1 1 d . . . . .
C3 C 0.8081(3) 0.4699(4) 1.0053(2) 0.0319(6) Uani 1 1 d . . . . .
H3A H 0.9014 0.5326 0.9967 0.038 Uiso 1 1 calc R . . . .
C4 C 0.4727(3) 0.3664(5) 0.5582(2) 0.0377(7) Uani 1 1 d . . . . .
H4 H 0.4763 0.2438 0.5726 0.045 Uiso 1 1 calc R . . . .
C5 C 0.7423(4) 0.5685(4) 1.0827(3) 0.0388(7) Uani 1 1 d . . . . .
H5A H 0.6399 0.5192 1.0835 0.047 Uiso 1 1 calc R . . . .
H5B H 0.8164 0.5557 1.1517 0.047 Uiso 1 1 calc R . . . .
C6 C 0.4743(4) 0.3942(4) 0.4473(3) 0.0392(7) Uani 1 1 d . . . . .
C7 C 0.3274(4) 0.4639(5) 0.3885(2) 0.0429(8) Uani 1 1 d . . . . .
C8 C 0.7188(4) 0.7547(5) 1.0577(3) 0.0408(8) Uani 1 1 d . . . . .
C9 C 0.3082(4) 0.4355(5) 0.5577(3) 0.0413(7) Uani 1 1 d . . . . .
C10 C 0.6169(3) 0.4517(5) 0.6336(2) 0.0389(7) Uani 1 1 d . . . . .
H10A H 0.7164 0.4014 0.6279 0.047 Uiso 1 1 calc R . . . .
H10B H 0.6181 0.5725 0.6184 0.047 Uiso 1 1 calc R . . . .
C11 C 0.2242(3) 0.4884(5) 0.4570(3) 0.0464(8) Uani 1 1 d . . . . .
C12 C 0.5969(5) 0.3639(5) 0.4023(3) 0.0501(9) Uani 1 1 d . . . . .
H12 H 0.6954 0.3200 0.4414 0.060 Uiso 1 1 calc R . . . .
C13 C 0.2376(4) 0.4471(6) 0.6372(3) 0.0544(10) Uani 1 1 d . . . . .
H13 H 0.2917 0.4094 0.7036 0.065 Uiso 1 1 calc R . . . .
C14 C 0.3026(5) 0.4988(6) 0.2838(3) 0.0614(11) Uani 1 1 d . . . . .
H14 H 0.2049 0.5436 0.2441 0.074 Uiso 1 1 calc R . . . .
C15 C 0.0704(4) 0.5573(6) 0.4369(4) 0.0610(11) Uani 1 1 d . . . . .
H15 H 0.0146 0.5929 0.3703 0.073 Uiso 1 1 calc R . . . .
C16 C 0.5698(5) 0.4005(6) 0.2979(3) 0.0663(12) Uani 1 1 d . . . . .
H16 H 0.6512 0.3801 0.2667 0.080 Uiso 1 1 calc R . . . .
C17 C 0.0024(5) 0.5720(7) 0.5171(4) 0.0712(13) Uani 1 1 d . . . . .
H17 H -0.0996 0.6200 0.5047 0.085 Uiso 1 1 calc R . . . .
C18 C 0.4256(5) 0.4660(7) 0.2395(3) 0.0711(12) Uani 1 1 d . . . . .
H18 H 0.4102 0.4887 0.1694 0.085 Uiso 1 1 calc R . . . .
C19 C 0.0827(4) 0.5168(7) 0.6160(4) 0.0685(12) Uani 1 1 d . . . . .
H19 H 0.0335 0.5261 0.6688 0.082 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
_geom_angle_publ_flag
C1 O1 C10 117.0(2) . . ?
C1 N1 C3 123.2(2) . . ?
O1 C1 N1 110.6(2) . . ?
O2 C1 O1 123.5(3) . . ?
O2 C1 N1 125.9(3) . . ?
O3 C2 C3 111.7(3) . . ?
O4 C2 O3 124.8(3) . . ?
O4 C2 C3 123.4(3) . . ?
N1 C3 C2 111.1(3) . . ?
N1 C3 C5 110.5(2) . . ?
C2 C3 C5 111.5(3) . . ?
C6 C4 C9 102.5(3) . . ?
C6 C4 C10 110.9(3) . . ?
C10 C4 C9 115.8(3) . . ?
C8 C5 C3 113.1(3) . . ?
C7 C6 C4 110.4(3) . . ?
C12 C6 C4 129.1(3) . . ?
C12 C6 C7 120.4(3) . . ?
C6 C7 C11 108.3(3) . . ?
C14 C7 C6 120.0(3) . . ?
C14 C7 C11 131.7(3) . . ?
O5 C8 C5 113.7(3) . . ?
O6 C8 O5 121.7(4) . . ?
O6 C8 C5 124.6(3) . . ?
C11 C9 C4 109.7(3) . . ?
C13 C9 C4 129.9(3) . . ?
C13 C9 C11 120.4(3) . . ?
O1 C10 C4 107.4(2) . . ?
C9 C11 C7 109.0(3) . . ?
C15 C11 C7 130.5(3) . . ?
C15 C11 C9 120.4(3) . . ?
C6 C12 C16 118.6(4) . . ?
C9 C13 C19 118.6(4) . . ?
C18 C14 C7 119.0(4) . . ?
C17 C15 C11 118.8(4) . . ?
C18 C16 C12 121.4(4) . . ?
C15 C17 C19 121.2(4) . . ?
C16 C18 C14 120.6(4) . . ?
C17 C19 C13 120.5(4) . . ?
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 1.331(3) . ?
O1 C10 1.443(4) . ?
O2 C1 1.223(3) . ?
O3 C2 1.308(4) . ?
O4 C2 1.210(4) . ?
O5 C8 1.306(4) . ?
O6 C8 1.192(4) . ?
N1 C1 1.343(4) . ?
N1 C3 1.434(4) . ?
C2 C3 1.518(5) . ?
C3 C5 1.530(4) . ?
C4 C6 1.511(5) . ?
C4 C9 1.521(4) . ?
C4 C10 1.519(4) . ?
C5 C8 1.500(5) . ?
C6 C7 1.401(5) . ?
C6 C12 1.383(5) . ?
C7 C11 1.467(5) . ?
C7 C14 1.389(5) . ?
C9 C11 1.402(5) . ?
C9 C13 1.378(5) . ?
C11 C15 1.390(5) . ?
C12 C16 1.386(5) . ?
C13 C19 1.399(6) . ?
C14 C18 1.384(6) . ?
C15 C17 1.373(7) . ?
C16 C18 1.370(6) . ?
C17 C19 1.381(7) . ?
