#------------------------------------------------------------------------------
#$Date: 2020-11-06 13:50:57 +0100 (vie 06 de nov de 2020) $
#$Revision: 258936 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/99/7059973.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_7059973
loop_
_publ_author_name
'Younes, Eyad A.'
'Hussein, Nour'
'Shtaiwi, Majed'
'Shahrokhi, Farshid'
'Abu Safieh, Kayed A.'
'Zhao, Yuming'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  28.00   0.50    4.57    --  -47.82  19.00 -60.00   88
  2  ω    -16.00  28.00   0.50    4.57    --  -47.82  19.00-120.00   88
  3  ω    -16.00  10.00   0.50    4.57    --  -47.82  19.00-150.00   52
  4  ω    -43.00 -18.00   0.50   22.00    --  -86.25  45.00-120.00   50
  5  ω    -41.00 -15.00   0.50   22.00    --  -86.25  45.00 -90.00   52
  6  ω    -85.00 -50.00   0.50    4.57    --  -47.82 134.00 -75.00   70
  7  ω    109.00 134.00   0.50   22.00    --  107.75 134.00 104.00   50
  8  ω     97.00 126.00   0.50   22.00    --  107.75  45.00  30.00   58
  9  ω    139.00 177.00   0.50   22.00    --  107.75  45.00  30.00   76
 10  ω    109.00 134.00   0.50   22.00    --  107.75 134.00 -75.00   50
 11  ω    142.00 168.00   0.50   22.00    --  107.75  61.00 -90.00   52
 12  ω    102.00 127.00   0.50   22.00    --  107.75  61.00 -90.00   50
 13  ω     96.00 177.00   0.50   22.00    --  107.75  45.00 -60.00  162
 14  ω     95.00 176.00   0.50   22.00    --  107.75  15.00 120.00  162
 15  ω     68.00 107.00   0.50   22.00    --  107.75-102.00  -2.82   78
 16  ω     86.00 111.00   0.50   22.00    --  107.75-125.00 -30.00   50
 17  ω     71.00 106.00   0.50   22.00    --  107.75-125.00-120.00   70
 18  ω     78.00 104.00   0.50   22.00    --  107.75 -94.00-150.00   52
 19  ω     49.00 119.00   0.50   22.00    --  107.75-134.00-142.00  140
 20  ω     53.00  79.00   0.50   22.00    --  107.75 -61.00-150.00   52
 21  ω     35.00  74.00   0.50   22.00    --  107.75 -94.00-150.00   78
 22  ω     38.00 103.00   0.50   22.00    --  107.75 -94.00 -90.00  130
 23  ω     50.00  76.00   0.50   22.00    --  107.75 -61.00   0.00   52
 24  ω     36.00  82.00   0.50   22.00    --  107.75 -94.00 -30.00   92
 25  ω     39.00  80.00   0.50   22.00    --  107.75-134.00  37.00   82
 26  ω     36.00  79.00   0.50   22.00    --  107.75 -61.00  90.00   86
 27  ω     46.00  71.00   0.50    4.57    --   47.82-134.00  37.00   50
 28  ω     35.00  76.00   0.50   22.00    --  107.75-125.00 -30.00   82
 29  ω     43.00  79.00   0.50    4.57    --   47.82-134.00-142.00   72
 30  ω    -93.00 -68.00   0.50    4.57    --  -47.82-134.00  37.00   50
 31  ω   -117.00 -70.00   0.50    4.57    --  -47.82-134.00-142.00   94
 32  ω   -138.00-113.00   0.50   22.00    --  -86.25-134.00  37.00   50
 33  ω   -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       'ω 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/[σ²(Fo²)+(0.1002P)²+0.7535P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.947
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.5259(2) 0.22677(7) 0.16781(17) 0.0420(4) Uani 1 1 d . . . . .
O2 O 0.5580(3) 0.43311(8) 0.5900(2) 0.0519(5) Uani 1 1 d . . . . .
O3 O 0.7947(3) 0.47676(9) 0.6130(2) 0.0629(6) Uani 1 1 d . . . . .
O4 O 1.2080(3) 0.37555(12) 0.4524(3) 0.0747(7) Uani 1 1 d . . . . .
O5 O 1.1015(3) 0.32135(10) 0.2519(3) 0.0719(7) Uani 1 1 d . . . . .
N1 N 0.0424(3) 0.19092(11) 0.2501(3) 0.0530(6) Uani 1 1 d . . . . .
N2 N 0.4719(2) 0.22437(8) 0.38401(19) 0.0288(4) Uani 1 1 d . . . . .
H2 H 0.492(4) 0.2395(13) 0.465(3) 0.042(7) Uiso 1 1 d . . . . .
N3 N 0.6937(3) 0.43587(9) 0.5711(2) 0.0442(5) Uani 1 1 d . . . . .
N4 N 1.0913(3) 0.34789(11) 0.3603(3) 0.0560(6) Uani 1 1 d . . . . .
C1 C 0.4217(2) 0.12688(9) 0.4721(2) 0.0300(4) Uani 1 1 d . . . . .
C2 C 0.5804(3) 0.09701(9) 0.5096(2) 0.0300(4) Uani 1 1 d . . . . .
C3 C 0.7017(3) 0.10852(9) 0.4404(2) 0.0321(4) Uani 1 1 d . . . . .
H3 H 0.676655 0.136797 0.362441 0.039 Uiso 1 1 calc R . . . .
C4 C 0.8544(3) 0.07956(10) 0.4840(3) 0.0394(5) Uani 1 1 d . . . . .
H4 H 0.934387 0.088091 0.436560 0.047 Uiso 1 1 calc R . . . .
C5 C 0.8940(3) 0.03748(11) 0.5980(3) 0.0446(6) Uani 1 1 d . . . . .
H5 H 1.001122 0.018009 0.628309 0.053 Uiso 1 1 calc R . . . .
C6 C 0.7796(3) 0.02436(10) 0.6654(3) 0.0435(6) Uani 1 1 d . . . . .
H6 H 0.806906 -0.004818 0.741302 0.052 Uiso 1 1 calc R . . . .
C7 C 0.6207(3) 0.05348(9) 0.6243(2) 0.0351(5) Uani 1 1 d . . . . .
C8 C 0.5020(3) 0.04137(11) 0.6960(2) 0.0425(6) Uani 1 1 d . . . . .
H8 H 0.525691 0.011024 0.768645 0.051 Uiso 1 1 calc R . . . .
C9 C 0.3559(3) 0.07214(12) 0.6630(3) 0.0442(6) Uani 1 1 d . . . . .
H9 H 0.280570 0.064617 0.715868 0.053 Uiso 1 1 calc R . . . .
C10 C 0.3145(3) 0.11548(11) 0.5502(2) 0.0373(5) Uani 1 1 d . . . . .
H10 H 0.211403 0.137008 0.527949 0.045 Uiso 1 1 calc R . . . .
C11 C 0.3724(2) 0.17089(9) 0.3437(2) 0.0304(4) Uani 1 1 d . . . . .
H11 H 0.397450 0.152722 0.258056 0.037 Uiso 1 1 calc R . . . .
C12 C 0.1865(3) 0.18332(10) 0.2908(2) 0.0388(5) Uani 1 1 d . . . . .
C13 C 0.5459(3) 0.24781(9) 0.2920(2) 0.0307(4) Uani 1 1 d . . . . .
C14 C 0.6612(3) 0.29873(9) 0.3514(2) 0.0317(4) Uani 1 1 d . . . . .
C15 C 0.6234(3) 0.34270(9) 0.4355(2) 0.0309(4) Uani 1 1 d . . . . .
H15 H 0.520259 0.341687 0.456169 0.037 Uiso 1 1 calc R . . . .
C16 C 0.7384(3) 0.38794(10) 0.4886(2) 0.0362(5) Uani 1 1 d . . . . .
C17 C 0.8919(3) 0.39076(11) 0.4666(3) 0.0416(5) Uani 1 1 d . . . . .
H17 H 0.970944 0.421459 0.507606 0.050 Uiso 1 1 calc R . . . .
C18 C 0.9252(3) 0.34710(11) 0.3825(3) 0.0420(6) Uani 1 1 d . . . . .
C19 C 0.8132(3) 0.30144(10) 0.3208(3) 0.0391(5) Uani 1 1 d . . . . .
H19 H 0.838793 0.272852 0.259472 0.047 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
C11 N2 H2 121(2) . . ?
C13 N2 H2 117(2) . . ?
C13 N2 C11 121.10(17) . . ?
O2 N3 O3 124.4(2) . . ?
O2 N3 C16 117.9(2) . . ?
O3 N3 C16 117.7(2) . . ?
O4 N4 C18 117.0(3) . . ?
O5 N4 O4 125.4(2) . . ?
O5 N4 C18 117.6(3) . . ?
C2 C1 C11 118.93(17) . . ?
C10 C1 C2 120.1(2) . . ?
C10 C1 C11 120.92(19) . . ?
C1 C2 C7 118.39(18) . . ?
C3 C2 C1 123.56(19) . . ?
C3 C2 C7 118.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 119.1(2) . . ?
C6 C7 C8 121.7(2) . . ?
C8 C7 C2 119.2(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.3(2) . . ?
C10 C9 H9 119.9 . . ?
C1 C10 C9 120.7(2) . . ?
C1 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N2 C11 C1 112.35(16) . . ?
N2 C11 H11 107.5 . . ?
N2 C11 C12 111.16(18) . . ?
C1 C11 H11 107.5 . . ?
C12 C11 C1 110.68(17) . . ?
C12 C11 H11 107.5 . . ?
N1 C12 C11 177.7(3) . . ?
O1 C13 N2 121.8(2) . . ?
O1 C13 C14 121.37(18) . . ?
N2 C13 C14 116.75(17) . . ?
C15 C14 C13 122.48(18) . . ?
C15 C14 C19 119.6(2) . . ?
C19 C14 C13 117.90(19) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.9(2) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 N3 118.6(2) . . ?
C17 C16 N3 118.2(2) . . ?
C17 C16 C15 123.2(2) . . ?
C16 C17 H17 121.7 . . ?
C18 C17 C16 116.7(2) . . ?
C18 C17 H17 121.7 . . ?
C17 C18 N4 118.1(2) . . ?
C17 C18 C19 123.4(2) . . ?
C19 C18 N4 118.5(2) . . ?
C14 C19 H19 120.9 . . ?
C18 C19 C14 118.1(2) . . ?
C18 C19 H19 120.9 . . ?
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 C13 1.230(2) . ?
O2 N3 1.211(3) . ?
O3 N3 1.230(3) . ?
O4 N4 1.232(4) . ?
O5 N4 1.225(4) . ?
N1 C12 1.142(3) . ?
N2 H2 0.80(3) . ?
N2 C11 1.455(3) . ?
N2 C13 1.348(3) . ?
N3 C16 1.473(3) . ?
N4 C18 1.477(3) . ?
C1 C2 1.422(3) . ?
C1 C10 1.376(3) . ?
C1 C11 1.523(3) . ?
C2 C3 1.415(3) . ?
C2 C7 1.427(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.360(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.413(3) . ?
C7 C8 1.416(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.349(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.412(4) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.483(3) . ?
C13 C14 1.492(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.403(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(3) . ?
C16 C17 1.373(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.369(4) . ?
C18 C19 1.389(4) . ?
C19 H19 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.80(3) 2.00(3) 2.804(2) 175(3) 4_566 yes
