#------------------------------------------------------------------------------
#$Date: 2024-05-05 03:37:59 +0200 (Sun 05 de May de 2024) $
#$Revision: 291566 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/12/1571295.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_1571295
loop_
_publ_author_name
'Venkatesh, Yarra'
'Marotta, Nicholas P.'
'Lee, Virginia M.-Y.'
'Petersson, E. James'
_publ_section_title
;
 Highly tunable bimane-based fluorescent probes: design, synthesis, and
 application as a selective amyloid binding dye.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              6053
_journal_page_last               6063
_journal_paper_doi               10.1039/d4sc00024b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C17 H15 F N2 O2, 0.125(H2 O)'
_chemical_formula_sum            'C17 H15.25 F N2 O2.125'
_chemical_formula_weight         300.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-04
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2024-01-04 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   29.9395(3)
_cell_length_b                   27.5788(3)
_cell_length_c                   7.07968(9)
_cell_measurement_reflns_used    25458
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.3230
_cell_measurement_theta_min      2.9490
_cell_volume                     5845.66(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  63.00   0.50    2.00    --   47.04 -59.00  90.00  174
  2  ω     31.00 120.00   0.50    2.00    --   47.04  59.00-128.00  178
  3  ω   -159.00 -70.00   0.50    8.00    --  -86.25 -59.00  90.00  178
  4  ω    -71.00 -14.00   0.50    8.00    --  -86.25  59.00-128.00  114
  5  ω     35.00  65.00   0.50    8.00    --  107.75 -59.00  90.00   60
  6  ω     92.00 178.00   0.50    8.00    --  107.75  59.00-128.00  172
  7  ω    -30.00  28.00   0.50    2.00    --  -47.04  19.00  30.00  116
  8  ω    -30.00  28.00   0.50    2.00    --  -47.04  19.00-180.00  116
  9  ω    -30.00  28.00   0.50    2.00    --  -47.04  19.00-120.00  116
 10  ω    -63.00  25.00   0.50    2.00    --  -47.04  59.00-128.00  176
 11  ω   -118.00 -31.00   0.50    2.00    --  -47.04 -59.00  90.00  174
 12  ω    -25.00  70.00   0.50    2.00    --   47.04 -77.00-180.00  190
 13  ω    -74.00 -13.00   0.50    8.00    --  -86.25  61.00  30.00  122
 14  ω    -38.00 -11.00   0.50    8.00    --  -86.25  30.00   0.00   54
 15  ω     35.00 132.00   0.50    8.00    --  107.75 -79.00  69.59  194
 16  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00 -60.00   66
 17  ω     94.00 178.00   0.50    8.00    --  107.75  15.00 -90.00  168
 18  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00   0.00  136
 19  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00-142.39  194
 20  ω     91.00 178.00   0.50    8.00    --  107.75  61.00-180.00  174
 21  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00 -72.43  194
 22  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00   0.00   66
 23  ω     95.00 178.00   0.50    8.00    --  107.75  30.00   0.00  166
 24  ω     95.00 178.00   0.50    8.00    --  107.75  30.00 -60.00  166
 25  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00  60.00   66
 26  ω     95.00 178.00   0.50    8.00    --  107.75  45.00 -90.00  166
 27  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00  27.20  194
 28  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00 150.00   66
 29  ω     95.00 178.00   0.50    8.00    --  107.75  45.00  60.00  166
 30  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00 -90.00  136
 31  ω     85.00 178.00   0.50    8.00    --  107.75  77.00 120.00  186
 32  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00-180.00  136
 33  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00 150.00  136
 34  ω     35.00  68.00   0.50    8.00    --  107.75 -61.00-150.00   66
 35  ω     95.00 178.00   0.50    8.00    --  107.75  30.00  60.00  166
 36  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00 120.93  194
 37  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00 -60.00  136
 38  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00 -30.00  136
 39  ω     35.00 103.00   0.50    8.00    --  107.75 -77.00  30.00  136
 40  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00-100.39  194
 41  ω     35.00 132.00   0.50    8.00    --  107.75 -80.00 151.11  194
 42  ω     35.00 132.00   0.50    8.00    --  107.75 -79.00-159.50  194
 43  ω     95.00 178.00   0.50    8.00    --  107.75  45.00 150.00  166
 44  ω   -119.00 -24.00   0.50    2.00    --  -47.04 -77.00   0.00  190
 45  ω   -118.00 -32.00   0.50    2.00    --  -47.04 -57.00 -90.00  172
 46  ω   -119.00 -24.00   0.50    2.00    --  -47.04 -77.00  60.00  190
 47  ω     24.00 120.00   0.50    2.00    --   47.04  77.00 150.00  192
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0339910000
_diffrn_orient_matrix_UB_12      -0.0416122000
_diffrn_orient_matrix_UB_13      0.0208038000
_diffrn_orient_matrix_UB_21      0.0117558000
_diffrn_orient_matrix_UB_22      -0.0045253000
_diffrn_orient_matrix_UB_23      0.2111295000
_diffrn_orient_matrix_UB_31      -0.0367973000
_diffrn_orient_matrix_UB_32      0.0369825000
_diffrn_orient_matrix_UB_33      0.0485163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            35147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         4.359
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             2516
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0568P)²+4.6832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2938
_reflns_number_total             2976
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc00024b2.cif
_cod_data_source_block           99536
_cod_depositor_comments
'Adding full bibliography for 1571295--1571297.cif.'
_cod_original_cell_volume        5845.66(12)
_cod_database_code               1571295
_shelx_shelxl_version_number     2019/3
_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   0.937
_shelx_estimated_absorpt_t_min   0.820
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O18(0.125) H18A(0.125) H18B(0.125)
 Fixed X: H18A(0.51765) H18B(0.480539)
 Fixed Y: H18A(0.48566) H18B(0.51494)
 Fixed Z: H18A(1.10291) H18B(1.09311)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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 1.938
_oxdiff_exptl_absorpt_empirical_full_min 0.505
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
C1 C 0.67861(7) 0.64779(8) 0.4534(4) 0.0358(5) Uani 1 1 d . . . . .
C2 C 0.71618(7) 0.61481(8) 0.4363(3) 0.0353(5) Uani 1 1 d . . . . .
C3 C 0.70176(7) 0.56830(9) 0.4697(3) 0.0351(5) Uani 1 1 d . . . . .
C4 C 0.62079(8) 0.54111(8) 0.5565(3) 0.0336(5) Uani 1 1 d . . . . .
C5 C 0.58388(7) 0.57002(8) 0.5737(4) 0.0354(5) Uani 1 1 d . . . . .
C6 C 0.59638(7) 0.61995(8) 0.5385(3) 0.0319(4) Uani 1 1 d . . . . .
C7 C 0.53762(9) 0.55528(10) 0.6239(6) 0.0578(8) Uani 1 1 d . . . . .
H7A H 0.521313 0.546477 0.508818 0.087 Uiso 1 1 calc R U . . .
H7B H 0.522396 0.582309 0.686558 0.087 Uiso 1 1 calc R U . . .
H7C H 0.538637 0.527332 0.709238 0.087 Uiso 1 1 calc R U . . .
C8 C 0.62555(8) 0.48799(8) 0.5823(4) 0.0416(6) Uani 1 1 d . . . . .
H8A H 0.630290 0.472556 0.459250 0.062 Uiso 1 1 calc R U . . .
H8B H 0.598344 0.474979 0.640235 0.062 Uiso 1 1 calc R U . . .
H8C H 0.651163 0.481337 0.664519 0.062 Uiso 1 1 calc R U . . .
C9 C 0.76096(8) 0.63237(11) 0.3751(5) 0.0486(6) Uani 1 1 d . . . . .
H9A H 0.757845 0.664027 0.313581 0.073 Uiso 1 1 calc R U . . .
H9B H 0.773993 0.609168 0.285931 0.073 Uiso 1 1 calc R U . . .
H9C H 0.780494 0.635484 0.485510 0.073 Uiso 1 1 calc R U . . .
C10 C 0.72592(7) 0.52276(9) 0.4654(3) 0.0368(5) Uani 1 1 d . . . . .
H10 H 0.710392 0.493701 0.435747 0.044 Uiso 1 1 calc R U . . .
C11 C 0.76998(7) 0.52092(9) 0.5027(3) 0.0361(5) Uani 1 1 d . . . . .
H11 H 0.783903 0.550819 0.533956 0.043 Uiso 1 1 calc R U . . .
C12 C 0.79887(7) 0.47812(8) 0.5006(3) 0.0345(5) Uani 1 1 d . . . . .
C13 C 0.78439(7) 0.43154(9) 0.4495(3) 0.0359(5) Uani 1 1 d . . . . .
H13 H 0.754289 0.426568 0.411761 0.043 Uiso 1 1 calc R U . . .
C14 C 0.81386(8) 0.39270(9) 0.4540(4) 0.0391(5) Uani 1 1 d . . . . .
H14 H 0.804272 0.361050 0.419968 0.047 Uiso 1 1 calc R U . . .
C15 C 0.85742(8) 0.40110(9) 0.5089(4) 0.0384(5) Uani 1 1 d . . . . .
C16 C 0.87313(8) 0.44607(9) 0.5582(4) 0.0398(5) Uani 1 1 d . . . . .
H16 H 0.903400 0.450714 0.594133 0.048 Uiso 1 1 calc R U . . .
C17 C 0.84321(8) 0.48467(9) 0.5537(3) 0.0373(5) Uani 1 1 d . . . . .
H17 H 0.853269 0.516161 0.587623 0.045 Uiso 1 1 calc R U . . .
N1 N 0.65631(7) 0.56996(7) 0.5070(4) 0.0411(5) Uani 1 1 d . . . . .
N2 N 0.64203(6) 0.61730(7) 0.4984(4) 0.0410(5) Uani 1 1 d . . . . .
O1 O 0.67590(6) 0.69171(6) 0.4347(3) 0.0442(4) Uani 1 1 d . . . . .
O2 O 0.57457(5) 0.65726(6) 0.5415(3) 0.0374(4) Uani 1 1 d . . . . .
F1 F 0.88603(5) 0.36294(6) 0.5133(3) 0.0536(4) Uani 1 1 d . . . . .
O18 O 0.500000 0.500000 1.0229(17) 0.053(3) Uani 0.25 2 d S T P . .
H18A H 0.517650 0.485660 1.102909 0.079 Uiso 0.125 1 d . U P . .
H18B H 0.480539 0.514940 1.093109 0.079 Uiso 0.125 1 d . U P . .
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'
F F 0.0727 0.0534 '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
N2 C1 C2 104.22(18) . . ?
O1 C1 C2 131.6(2) . . ?
O1 C1 N2 124.2(2) . . ?
C1 C2 C9 121.2(2) . . ?
C3 C2 C1 109.11(19) . . ?
C3 C2 C9 129.5(2) . . ?
C2 C3 C10 130.4(2) . . ?
C2 C3 N1 108.07(19) . . ?
N1 C3 C10 121.5(2) . . ?
C5 C4 C8 130.0(2) . . ?
C5 C4 N1 108.1(2) . . ?
N1 C4 C8 122.0(2) . . ?
C4 C5 C6 109.28(19) . . ?
C4 C5 C7 127.9(2) . . ?
C6 C5 C7 122.8(2) . . ?
N2 C6 C5 103.76(18) . . ?
O2 C6 C5 131.4(2) . . ?
O2 C6 N2 124.86(19) . . ?
C11 C10 C3 121.2(2) . . ?
C10 C11 C12 127.4(2) . . ?
C13 C12 C11 123.9(2) . . ?
C17 C12 C11 117.1(2) . . ?
C17 C12 C13 118.9(2) . . ?
C14 C13 C12 120.3(2) . . ?
C15 C14 C13 118.5(2) . . ?
C16 C15 C14 123.2(2) . . ?
F1 C15 C14 118.2(2) . . ?
F1 C15 C16 118.6(2) . . ?
C15 C16 C17 117.7(2) . . ?
C12 C17 C16 121.4(2) . . ?
C4 N1 C3 142.1(2) . . ?
C4 N1 N2 108.70(18) . . ?
N2 N1 C3 109.15(18) . . ?
C6 N2 C1 140.38(18) . . ?
N1 N2 C1 109.45(18) . . ?
N1 N2 C6 110.16(17) . . ?
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
C1 C2 1.452(3) . ?
C1 N2 1.417(3) . ?
C1 O1 1.221(3) . ?
C2 C3 1.374(3) . ?
C2 C9 1.490(3) . ?
C3 C10 1.450(3) . ?
C3 N1 1.387(3) . ?
C4 C5 1.368(3) . ?
C4 C8 1.483(3) . ?
C4 N1 1.374(3) . ?
C5 C6 1.448(3) . ?
C5 C7 1.487(3) . ?
C6 N2 1.398(3) . ?
C6 O2 1.219(3) . ?
C10 C11 1.346(3) . ?
C11 C12 1.464(3) . ?
C12 C13 1.403(3) . ?
C12 C17 1.392(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.371(3) . ?
C15 F1 1.357(3) . ?
C16 C17 1.392(3) . ?
N1 N2 1.375(3) . ?
