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#$Date: 2023-03-06 12:18:52 +0200 (Mon, 06 Mar 2023) $
#$Revision: 281668 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106848.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_8106848
loop_
_publ_author_name
'Al-Abdullah, Ebtehal S.'
'Ghabbour, Hazem A.'
'Al-Jabal, Maher M.'
'Fun, Hoong-Kun'
'El-Emam, Ali A.'
_publ_section_title
;
 Crystal structure of
 N′-(adamantan-2-ylidene)-isonicotinohydrazide, C16H19N3O
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              273
_journal_page_last               275
_journal_paper_doi               10.1515/ncrs-2015-0118
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0251(7)
_cell_length_b                   10.1627(9)
_cell_length_c                   17.0686(16)
_cell_measurement_reflns_used    4654
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.43
_cell_measurement_theta_min      2.33
_cell_volume                     1392.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12950
_diffrn_reflns_theta_full        33.16
_diffrn_reflns_theta_max         33.16
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(9)
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.1058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                3230
_reflns_number_total             4046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0118_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106848
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16514(13) 0.58777(11) 0.39484(7) 0.0146(3) Uani 1 1 d . . .
N1 N 0.23852(15) 0.78709(13) 0.49212(8) 0.0095(3) Uani 1 1 d . . .
N2 N 0.36193(15) 0.72089(13) 0.45016(8) 0.0099(3) Uani 1 1 d . . .
N3 N 0.70268(19) 0.37745(16) 0.30832(10) 0.0222(4) Uani 1 1 d . . .
C1 C 0.45221(19) 0.93516(16) 0.55573(10) 0.0124(3) Uani 1 1 d . . .
H1A H 0.5392 0.8881 0.5245 0.015 Uiso 1 1 calc R . .
C2 C 0.4473(2) 1.08226(17) 0.53342(11) 0.0188(4) Uani 1 1 d . . .
H2A H 0.5575 1.1227 0.5435 0.023 Uiso 1 1 calc R . .
H2B H 0.4222 1.0914 0.4769 0.023 Uiso 1 1 calc R . .
C3 C 0.3138(2) 1.15345(16) 0.58156(10) 0.0155(3) Uani 1 1 d . . .
H3A H 0.3123 1.2488 0.5671 0.019 Uiso 1 1 calc R . .
C4 C 0.1437(2) 1.09247(16) 0.56399(12) 0.0178(4) Uani 1 1 d . . .
H4A H 0.1174 1.1028 0.5077 0.021 Uiso 1 1 calc R . .
H4B H 0.0564 1.1383 0.5946 0.021 Uiso 1 1 calc R . .
C5 C 0.14561(19) 0.94550(16) 0.58552(10) 0.0121(3) Uani 1 1 d . . .
H5A H 0.0353 0.9046 0.5732 0.015 Uiso 1 1 calc R . .
C6 C 0.28218(19) 0.87848(15) 0.53929(10) 0.0094(3) Uani 1 1 d . . .
C7 C 0.4875(2) 0.92129(17) 0.64432(11) 0.0181(4) Uani 1 1 d . . .
H7A H 0.4879 0.8270 0.6589 0.022 Uiso 1 1 calc R . .
H7B H 0.5988 0.9582 0.6564 0.022 Uiso 1 1 calc R . .
C8 C 0.3544(2) 0.99406(16) 0.69190(11) 0.0162(3) Uani 1 1 d . . .
H8A H 0.3788 0.9852 0.7491 0.019 Uiso 1 1 calc R . .
C9 C 0.1841(2) 0.93121(17) 0.67339(10) 0.0167(4) Uani 1 1 d . . .
H9A H 0.1859 0.8369 0.6878 0.020 Uiso 1 1 calc R . .
H9B H 0.0959 0.9750 0.7045 0.020 Uiso 1 1 calc R . .
C10 C 0.3524(2) 1.13957(17) 0.66916(11) 0.0166(3) Uani 1 1 d . . .
H10A H 0.4621 1.1796 0.6808 0.020 Uiso 1 1 calc R . .
H10B H 0.2668 1.1865 0.7002 0.020 Uiso 1 1 calc R . .
C11 C 0.31161(18) 0.61749(15) 0.40514(10) 0.0101(3) Uani 1 1 d . . .
C12 C 0.45008(19) 0.53800(16) 0.36979(10) 0.0108(3) Uani 1 1 d . . .
C13 C 0.5968(2) 0.59304(16) 0.34086(10) 0.0137(3) Uani 1 1 d . . .
H13A H 0.6134 0.6856 0.3413 0.016 Uiso 1 1 calc R . .
C14 C 0.7183(2) 0.50888(19) 0.31132(11) 0.0205(4) Uani 1 1 d . . .
H14A H 0.8185 0.5468 0.2921 0.025 Uiso 1 1 calc R . .
C15 C 0.5594(2) 0.32714(17) 0.33452(11) 0.0190(4) Uani 1 1 d . . .
H15A H 0.5446 0.2345 0.3317 0.023 Uiso 1 1 calc R . .
C16 C 0.4307(2) 0.40221(15) 0.36565(10) 0.0135(3) Uani 1 1 d . . .
H16A H 0.3313 0.3615 0.3838 0.016 Uiso 1 1 calc R . .
H1N2 H 0.466(2) 0.7362(17) 0.4582(12) 0.008(4) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C6 N1 N2 118.63(13) . .
C11 N2 N1 116.80(12) . .
C11 N2 H1N2 121.2(12) . .
N1 N2 H1N2 121.2(13) . .
C15 N3 C14 116.66(15) . .
C6 C1 C2 107.53(13) . .
C6 C1 C7 108.27(14) . .
C2 C1 C7 109.55(14) . .
C6 C1 H1A 110.5 . .
C2 C1 H1A 110.5 . .
C7 C1 H1A 110.5 . .
C3 C2 C1 110.05(14) . .
C3 C2 H2A 109.7 . .
C1 C2 H2A 109.7 . .
C3 C2 H2B 109.7 . .
C1 C2 H2B 109.7 . .
H2A C2 H2B 108.2 . .
C4 C3 C2 109.14(14) . .
C4 C3 C10 109.53(15) . .
C2 C3 C10 109.78(14) . .
C4 C3 H3A 109.5 . .
C2 C3 H3A 109.5 . .
C10 C3 H3A 109.5 . .
C3 C4 C5 109.74(13) . .
C3 C4 H4A 109.7 . .
C5 C4 H4A 109.7 . .
C3 C4 H4B 109.7 . .
C5 C4 H4B 109.7 . .
H4A C4 H4B 108.2 . .
C6 C5 C4 108.66(14) . .
C6 C5 C9 108.71(14) . .
C4 C5 C9 109.06(14) . .
C6 C5 H5A 110.1 . .
C4 C5 H5A 110.1 . .
C9 C5 H5A 110.1 . .
N1 C6 C1 130.02(14) . .
N1 C6 C5 117.21(14) . .
C1 C6 C5 112.75(14) . .
C8 C7 C1 110.29(14) . .
C8 C7 H7A 109.6 . .
C1 C7 H7A 109.6 . .
C8 C7 H7B 109.6 . .
C1 C7 H7B 109.6 . .
H7A C7 H7B 108.1 . .
C10 C8 C7 109.84(14) . .
C10 C8 C9 109.85(14) . .
C7 C8 C9 108.04(14) . .
C10 C8 H8A 109.7 . .
C7 C8 H8A 109.7 . .
C9 C8 H8A 109.7 . .
C5 C9 C8 109.80(14) . .
C5 C9 H9A 109.7 . .
C8 C9 H9A 109.7 . .
C5 C9 H9B 109.7 . .
C8 C9 H9B 109.7 . .
H9A C9 H9B 108.2 . .
C8 C10 C3 109.79(14) . .
C8 C10 H10A 109.7 . .
C3 C10 H10A 109.7 . .
C8 C10 H10B 109.7 . .
C3 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
O1 C11 N2 123.69(14) . .
O1 C11 C12 121.31(14) . .
N2 C11 C12 114.98(13) . .
C16 C12 C13 118.35(14) . .
C16 C12 C11 118.15(14) . .
C13 C12 C11 123.51(14) . .
C14 C13 C12 118.27(15) . .
C14 C13 H13A 120.9 . .
C12 C13 H13A 120.9 . .
N3 C14 C13 124.03(17) . .
N3 C14 H14A 118.0 . .
C13 C14 H14A 118.0 . .
N3 C15 C16 123.91(16) . .
N3 C15 H15A 118.0 . .
C16 C15 H15A 118.0 . .
C12 C16 C15 118.75(15) . .
C12 C16 H16A 120.6 . .
C15 C16 H16A 120.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.2262(18) .
N1 C6 1.278(2) .
N1 N2 1.3951(17) .
N2 C11 1.363(2) .
N2 H1N2 0.857(19) .
N3 C15 1.336(2) .
N3 C14 1.343(3) .
C1 C6 1.507(2) .
C1 C2 1.543(2) .
C1 C7 1.545(3) .
C1 H1A 1.0000 .
C2 C3 1.532(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.529(2) .
C3 C10 1.533(3) .
C3 H3A 1.0000 .
C4 C5 1.538(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.513(2) .
C5 C9 1.538(2) .
C5 H5A 1.0000 .
C7 C8 1.533(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C10 1.529(3) .
C8 C9 1.541(2) .
C8 H8A 1.0000 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.501(2) .
C12 C16 1.391(2) .
C12 C13 1.394(2) .
C13 C14 1.392(2) .
C13 H13A 0.9500 .
C14 H14A 0.9500 .
C15 C16 1.390(2) .
C15 H15A 0.9500 .
C16 H16A 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 N1 N2 C11 175.08(15) . . . .
C6 C1 C2 C3 59.39(18) . . . .
C7 C1 C2 C3 -58.05(17) . . . .
C1 C2 C3 C4 -60.73(18) . . . .
C1 C2 C3 C10 59.33(18) . . . .
C2 C3 C4 C5 59.73(19) . . . .
C10 C3 C4 C5 -60.48(18) . . . .
C3 C4 C5 C6 -58.18(18) . . . .
C3 C4 C5 C9 60.18(18) . . . .
N2 N1 C6 C1 3.5(3) . . . .
N2 N1 C6 C5 -178.30(13) . . . .
C2 C1 C6 N1 118.45(19) . . . .
C7 C1 C6 N1 -123.27(18) . . . .
C2 C1 C6 C5 -59.80(18) . . . .
C7 C1 C6 C5 58.48(18) . . . .
C4 C5 C6 N1 -118.82(16) . . . .
C9 C5 C6 N1 122.61(16) . . . .
C4 C5 C6 C1 59.68(18) . . . .
C9 C5 C6 C1 -58.90(18) . . . .
C6 C1 C7 C8 -59.14(18) . . . .
C2 C1 C7 C8 57.84(17) . . . .
C1 C7 C8 C10 -58.85(18) . . . .
C1 C7 C8 C9 60.96(18) . . . .
C6 C5 C9 C8 59.10(17) . . . .
C4 C5 C9 C8 -59.22(17) . . . .
C10 C8 C9 C5 58.98(18) . . . .
C7 C8 C9 C5 -60.82(18) . . . .
C7 C8 C10 C3 59.71(17) . . . .
C9 C8 C10 C3 -59.00(18) . . . .
C4 C3 C10 C8 59.79(17) . . . .
C2 C3 C10 C8 -60.03(17) . . . .
N1 N2 C11 O1 6.3(2) . . . .
N1 N2 C11 C12 -172.07(13) . . . .
O1 C11 C12 C16 -36.7(2) . . . .
N2 C11 C12 C16 141.75(15) . . . .
O1 C11 C12 C13 143.26(17) . . . .
N2 C11 C12 C13 -38.3(2) . . . .
C16 C12 C13 C14 -1.8(2) . . . .
C11 C12 C13 C14 178.31(16) . . . .
C15 N3 C14 C13 1.1(3) . . . .
C12 C13 C14 N3 0.5(3) . . . .
C14 N3 C15 C16 -1.6(3) . . . .
C13 C12 C16 C15 1.4(2) . . . .
C11 C12 C16 C15 -178.69(15) . . . .
N3 C15 C16 C12 0.3(3) . . . .
