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_7059971
_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 H14 N2 O'
_chemical_formula_sum            'C19 H14 N2 O'
_chemical_formula_weight         286.32
_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             2020-02-19
_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                 102.686(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8495(2)
_cell_length_b                   5.05830(10)
_cell_length_c                   16.2521(3)
_cell_measurement_reflns_used    5311
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7060
_cell_measurement_theta_min      5.5720
_cell_volume                     709.74(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.991
_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    3.87    --  -47.82  19.00 -30.00   88
  2  \w    -43.00 -14.00   0.50   18.00    --  -86.25  45.00 -30.00   58
  3  \w    -83.00  -5.00   0.50    3.87    --  -47.82 114.00 124.00  156
  4  \w     27.00  90.00   0.50    3.87    --   47.82-114.00  32.00  126
  5  \w     59.00 121.00   0.50    3.87    --   47.82-175.00-105.00  124
  6  \w     59.00 148.00   0.50   18.00    --  107.75-175.00-105.00  178
  7  \w     35.00 108.00   0.50   18.00    --  107.75-114.00  32.00  146
  8  \w     35.00 106.00   0.50   18.00    --  107.75-101.00  42.08  142
  9  \w     35.00  79.00   0.50   18.00    --  107.75 -61.00  90.00   88
 10  \w     35.00 106.00   0.50   18.00    --  107.75 -94.00  60.00  142
 11  \w     35.00 106.00   0.50   18.00    --  107.75 -94.00   0.00  142
 12  \w     35.00 106.00   0.50   18.00    --  107.75 -94.00-150.00  142
 13  \w     35.00 106.00   0.50   18.00    --  107.75 -94.00 -90.00  142
 14  \w     35.00 108.00   0.50   18.00    --  107.75-109.00 -51.96  146
 15  \w     35.00 106.00   0.50   18.00    --  107.75 -94.00-120.00  142
 16  \w     94.00 178.00   0.50   18.00    --  107.75  15.00 -60.00  168
 17  \w     95.00 178.00   0.50   18.00    --  107.75 125.00-150.00  166
 18  \w     95.00 178.00   0.50   18.00    --  107.75  30.00   0.00  166
 19  \w    102.00 178.00   0.50   18.00    --  107.75 114.00 124.00  152
 20  \w     95.00 178.00   0.50   18.00    --  107.75  45.00  60.00  166
 21  \w     95.00 178.00   0.50   18.00    --  107.75 125.00 -30.00  166
 22  \w     95.00 178.00   0.50   18.00    --  107.75  45.00-120.00  166
 23  \w     95.00 178.00   0.50   18.00    --  107.75 125.00 -60.00  166
 24  \w     91.00 178.00   0.50   18.00    --  107.75  61.00  30.00  174
 25  \w     95.00 178.00   0.50   18.00    --  107.75  45.00 150.00  166
 26  \w     85.00 178.00   0.50   18.00    --  107.75  77.00  90.00  186
 27  \w     91.00 178.00   0.50   18.00    --  107.75  61.00 -60.00  174
 28  \w     85.00 178.00   0.50   18.00    --  107.75  77.00-180.00  186
 29  \w     91.00 178.00   0.50   18.00    --  107.75  61.00-150.00  174
 30  \w     64.00 147.00   0.50   18.00    --  107.75 175.00 -97.00  166
 31  \w    -26.00  30.00   0.50    3.87    --   47.82 -19.00-120.00  112
 32  \w     35.00 112.00   0.50   18.00    --  107.75-125.00 150.00  154
 33  \w     35.00 107.00   0.50   18.00    --  107.75-104.00 166.68  144
 34  \w   -119.00 -43.00   0.50    3.87    --  -47.82-175.00-105.00  152
 35  \w   -119.00 -25.00   0.50    3.87    --  -47.82 -77.00 -30.00  188
 36  \w   -119.00 -81.50   0.50    3.87    --  -47.82 -77.00  60.00   75
;
_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      0.1677205000
_diffrn_orient_matrix_UB_12      -0.0599551000
_diffrn_orient_matrix_UB_13      -0.0065967000
_diffrn_orient_matrix_UB_21      -0.0421290000
_diffrn_orient_matrix_UB_22      -0.2938421000
_diffrn_orient_matrix_UB_23      -0.0159387000
_diffrn_orient_matrix_UB_31      -0.0443233000
_diffrn_orient_matrix_UB_32      0.0531749000
_diffrn_orient_matrix_UB_33      -0.0955635000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13880
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.368
_diffrn_reflns_theta_min         2.787
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57412
_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    1.340
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane and Chloroform'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1163 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0305P)^2^+0.2788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                2823
_reflns_number_total             2943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03105d2.cif
_cod_data_source_block           n1
_cod_depositor_comments
'Adding full bibliography for 7059971--7059973.cif.'
_cod_database_code               7059971
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H14N2O
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.912
_diffrn_oxdiff_digest_frames
;
01e4108e1641e6aad062c5ab9057ce0f6c0002677d4
;
_diffrn_oxdiff_digest_hkl
;
018bcf4812d030638a775b5a87c7e08df369bb
;
_reflns_odcompleteness_completeness 99.88
_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),
 C17(H17), C18(H18), C19(H19)
;
_shelx_res_checksum              2327
_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 2.127
_oxdiff_exptl_absorpt_empirical_full_min 0.615