N-(Cyano(naphthalen-1-yl)methyl)benzamides: synthesis, crystal structures, and colorimetric sensing of fluoride anions
Younes, Eyad A.; Hussein, Nour; Shtaiwi, Majed; Shahrokhi, Farshid; Abu Safieh, Kayed A.; Zhao, Yuming; New Journal of Chemistry 44 (2020) 16546–16556; doi:10.1039/D0NJ03105D

data_7059972
_publ_section_title
;
 N-(Cyano(naphthalen-1-yl)methyl)benzamides: synthesis, crystal
 structures, and colorimetric sensing of fluoride anions
;
_journal_issue                   38
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16546
_journal_page_last               16556
_journal_paper_doi               10.1039/D0NJ03105D
_journal_volume                  44
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H13 N3 O3'
_chemical_formula_sum            'C19 H13 N3 O3'
_chemical_formula_weight         331.32
_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
_audit_creation_date             2020-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-26 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.4463(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.98087(4)
_cell_length_b                   14.03570(14)
_cell_length_c                   11.32877(11)
_cell_measurement_reflns_used    13528
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.9070
_cell_measurement_theta_min      3.8670
_cell_volume                     789.611(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     33.00 119.00   0.50    0.05    --   47.82  57.00  90.00  172
  2  \w     91.00 178.00   0.50    0.30    --  107.75  61.00 120.00  174
  3  \w     95.00 178.00   0.50    0.30    --  107.75  45.00 150.00  166
  4  \w     85.00 178.00   0.50    0.30    --  107.75  77.00   0.00  186
  5  \w     95.00 178.00   0.50    0.30    --  107.75  30.00 120.00  166
  6  \w     95.00 178.00   0.50    0.30    --  107.75  45.00   0.00  166
  7  \w     95.00 178.00   0.50    0.30    --  107.75  30.00  90.00  166
  8  \w     88.00 178.00   0.50    0.30    --  107.75  70.00 -47.12  180
  9  \w     91.00 178.00   0.50    0.30    --  107.75  61.00 -90.00  174
 10  \w     95.00 178.00   0.50    0.30    --  107.75  45.00-150.00  166
 11  \w    -16.00  28.00   0.50    0.05    --  -47.82  19.00-150.00   88
 12  \w    -16.00  28.00   0.50    0.05    --  -47.82  19.00   0.00   88
 13  \w    -43.00 -14.00   0.50    0.30    --  -86.25  45.00  30.00   58
 14  \w   -113.00 -13.00   0.50    0.30    --  -86.25  87.00  18.00  200
 15  \w    -75.00  25.00   0.50    0.05    --  -47.82  87.00  18.00  200
 16  \w    101.00 178.00   0.50    0.30    --  107.75  87.00  18.00  154
 17  \w     95.00 178.00   0.50    0.30    --  107.75 125.00  60.00  166
 18  \w     95.00 178.00   0.50    0.30    --  107.75 125.00 120.00  166
 19  \w     35.00 112.00   0.50    0.30    --  107.75-125.00  60.00  154
 20  \w     35.00 112.00   0.50    0.30    --  107.75-125.00 -60.00  154
 21  \w     35.00 112.00   0.50    0.30    --  107.75-125.00 -90.00  154
 22  \w     35.00 106.00   0.50    0.30    --  107.75 -94.00-150.00  142
 23  \w     35.00 106.00   0.50    0.30    --  107.75 -94.00 -90.00  142
 24  \w     34.00  96.00   0.50    0.05    --   47.82-125.00-120.00  124
 25  \w    -21.00  75.00   0.50    0.05    --   47.82 -87.00 -98.00  192
 26  \w     35.00 135.00   0.50    0.30    --  107.75 -87.00 -98.00  200
 27  \w     35.00 106.00   0.50    0.30    --  107.75 -94.00 -30.00  142
 28  \w     35.00 106.00   0.50    0.30    --  107.75 -94.00 150.00  142
 29  \w     35.00 106.00   0.50    0.30    --  107.75 -94.00  90.00  142
 30  \w     35.00  79.00   0.50    0.30    --  107.75 -61.00 -30.00   88
 31  \w     35.00  79.00   0.50    0.30    --  107.75 -61.00 -90.00   88
 32  \w     35.00  79.00   0.50    0.30    --  107.75 -61.00-180.00   88
 33  \w     35.00  79.00   0.50    0.30    --  107.75 -61.00   0.00   88
 34  \w     35.00  79.00   0.50    0.30    --  107.75 -61.00  60.00   88
 35  \w     35.00  79.00   0.50    0.30    --  107.75 -61.00 120.00   88
 36  \w    -26.00  30.00   0.50    0.05    --   47.82 -19.00 -30.00  112
 37  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 -60.00  188
 38  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00-180.00  188
 39  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00-150.00  188
 40  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 -90.00  188
 41  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 -30.00  188
 42  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 120.00  188
 43  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00  90.00  188
 44  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00  30.00  188
 45  \w   -119.00 -33.00   0.50    0.05    --  -47.82 -57.00 -30.00  172
 46  \w   -159.00 -79.00   0.50    0.30    --  -86.25 -87.00 -98.00  160
 47  \w   -119.00 -73.00   0.50    0.05    --  -47.82-125.00 -30.00   92
 48  \w   -119.00 -73.00   0.50    0.05    --  -47.82-125.00  30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0643672000
_diffrn_orient_matrix_UB_12      -0.0751427000
_diffrn_orient_matrix_UB_13      -0.0972535000
_diffrn_orient_matrix_UB_21      -0.2294073000
_diffrn_orient_matrix_UB_22      0.0633766000
_diffrn_orient_matrix_UB_23      -0.0548799000
_diffrn_orient_matrix_UB_31      0.1985214000
_diffrn_orient_matrix_UB_32      0.0488479000
_diffrn_orient_matrix_UB_33      -0.0783820000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19960
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.399
_diffrn_reflns_theta_min         3.914
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.95155
_exptl_absorpt_correction_T_min  0.95155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane and Chloroform'
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.06
_exptl_crystal_size_rad          0.053
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0309
_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/[\s^2^(Fo^2^)+(0.0405P)^2^+0.1253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                3242
_reflns_number_total             3300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03105d2.cif
_cod_data_source_block           n2
_cod_depositor_comments
'Adding full bibliography for 7059971--7059973.cif.'
_cod_original_cell_volume        789.610(13)
_cod_database_code               7059972
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H14N2O
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.845
_diffrn_oxdiff_digest_frames
;
015033dbaa6088fb2d60ac4f111bbb2deb00121efc1
;
_diffrn_oxdiff_digest_hkl
;
01c51d3a9adec9d075c8ac12d259991d18a712
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C18(H18), C19(H19)
;
_shelx_res_checksum              96277
_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.836