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_7059973
_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_formula_moiety         'C19 H12 N4 O5'
_chemical_formula_sum            'C19 H12 N4 O5'
_chemical_formula_weight         376.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-20
_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                 110.706(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3646(2)
_cell_length_b                   22.9273(6)
_cell_length_c                   9.4978(2)
_cell_measurement_reflns_used    5183
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.7380
_cell_measurement_theta_min      5.9600
_cell_volume                     1703.81(8)
_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 0.981
_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    -16.00  28.00   0.50    4.57    --  -47.82  19.00 -60.00   88
  2  \w    -16.00  28.00   0.50    4.57    --  -47.82  19.00-120.00   88
  3  \w    -16.00  10.00   0.50    4.57    --  -47.82  19.00-150.00   52
  4  \w    -43.00 -18.00   0.50   22.00    --  -86.25  45.00-120.00   50
  5  \w    -41.00 -15.00   0.50   22.00    --  -86.25  45.00 -90.00   52
  6  \w    -85.00 -50.00   0.50    4.57    --  -47.82 134.00 -75.00   70
  7  \w    109.00 134.00   0.50   22.00    --  107.75 134.00 104.00   50
  8  \w     97.00 126.00   0.50   22.00    --  107.75  45.00  30.00   58
  9  \w    139.00 177.00   0.50   22.00    --  107.75  45.00  30.00   76
 10  \w    109.00 134.00   0.50   22.00    --  107.75 134.00 -75.00   50
 11  \w    142.00 168.00   0.50   22.00    --  107.75  61.00 -90.00   52
 12  \w    102.00 127.00   0.50   22.00    --  107.75  61.00 -90.00   50
 13  \w     96.00 177.00   0.50   22.00    --  107.75  45.00 -60.00  162
 14  \w     95.00 176.00   0.50   22.00    --  107.75  15.00 120.00  162
 15  \w     68.00 107.00   0.50   22.00    --  107.75-102.00  -2.82   78
 16  \w     86.00 111.00   0.50   22.00    --  107.75-125.00 -30.00   50
 17  \w     71.00 106.00   0.50   22.00    --  107.75-125.00-120.00   70
 18  \w     78.00 104.00   0.50   22.00    --  107.75 -94.00-150.00   52
 19  \w     49.00 119.00   0.50   22.00    --  107.75-134.00-142.00  140
 20  \w     53.00  79.00   0.50   22.00    --  107.75 -61.00-150.00   52
 21  \w     35.00  74.00   0.50   22.00    --  107.75 -94.00-150.00   78
 22  \w     38.00 103.00   0.50   22.00    --  107.75 -94.00 -90.00  130
 23  \w     50.00  76.00   0.50   22.00    --  107.75 -61.00   0.00   52
 24  \w     36.00  82.00   0.50   22.00    --  107.75 -94.00 -30.00   92
 25  \w     39.00  80.00   0.50   22.00    --  107.75-134.00  37.00   82
 26  \w     36.00  79.00   0.50   22.00    --  107.75 -61.00  90.00   86
 27  \w     46.00  71.00   0.50    4.57    --   47.82-134.00  37.00   50
 28  \w     35.00  76.00   0.50   22.00    --  107.75-125.00 -30.00   82
 29  \w     43.00  79.00   0.50    4.57    --   47.82-134.00-142.00   72
 30  \w    -93.00 -68.00   0.50    4.57    --  -47.82-134.00  37.00   50
 31  \w   -117.00 -70.00   0.50    4.57    --  -47.82-134.00-142.00   94
 32  \w   -138.00-113.00   0.50   22.00    --  -86.25-134.00  37.00   50
 33  \w   -116.00 -76.00   0.50    4.57    --  -47.82-125.00 150.00   80
;
_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      -0.0329378000
_diffrn_orient_matrix_UB_12      0.0215585000
_diffrn_orient_matrix_UB_13      0.1410259000
_diffrn_orient_matrix_UB_21      0.0115423000
_diffrn_orient_matrix_UB_22      0.0636298000
_diffrn_orient_matrix_UB_23      -0.0475607000
_diffrn_orient_matrix_UB_31      -0.1937211000
_diffrn_orient_matrix_UB_32      0.0000685000
_diffrn_orient_matrix_UB_33      -0.0891248000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14535
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.273
_diffrn_reflns_theta_min         3.856
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane and Chloroform'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0611
_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^)+(0.1002P)^2^+0.7535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1757
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2982
_reflns_number_total             3550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03105d2.cif
_cod_data_source_block           n3
_cod_depositor_comments
'Adding full bibliography for 7059971--7059973.cif.'
_cod_database_code               7059973
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H13N4O2
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.852
_diffrn_oxdiff_digest_frames
;
0174854a45ab953e30bc815101d11dac120002576ae
;
_diffrn_oxdiff_digest_hkl
;
01d7d6991a8f0450c68ae52a85cf0da1f67286
;
_reflns_odcompleteness_completeness 99.89
_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), C17(H17),
 C19(H19)
;
_shelx_res_checksum              11008
_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 1.824
_oxdiff_exptl_absorpt_empirical_full_min 0.552