#------------------------------------------------------------------------------
#$Date: 2022-07-30 04:56:58 +0300 (Sat, 30 Jul 2022) $
#$Revision: 277011 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244138
loop_
_publ_author_name
'Missioui, Mohcine'
'Guerrab, Walid'
'Alsubari, Abdulsalam'
'Mague, Joel T.'
'Ramli, Youssef'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 2-azido-N-(4-fluorophenyl)acetamide
;
_journal_coeditor_code           VM2266
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              855
_journal_page_last               859
_journal_paper_doi               10.1107/S2056989022006764
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C8 H7 F N4 O'
_chemical_formula_moiety         'C8 H7 F N4 O'
_chemical_formula_sum            'C8 H7 F N4 O'
_chemical_formula_weight         194.18
_chemical_name_systematic
;
2-Azido-N-(4-fluorophenyl)acetamide
;
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 112.378(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.8398(7)
_cell_length_b                   19.0207(11)
_cell_length_c                   9.3307(5)
_cell_measurement_reflns_used    8481
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      68.2848
_cell_measurement_theta_min      2.3229
_cell_volume                     1778.93(18)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT  (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12623
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.495
_diffrn_reflns_theta_min         4.411
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.997
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.237
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL 2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0533
_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)+(0.0828P)²+0.4718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                2545
_reflns_number_total             3224
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2266sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2244138
_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_min   0.654
_shelx_estimated_absorpt_t_max   0.868
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.75450(16) 0.51934(8) 0.5506(2) 0.1053(6) Uani d 1 . .
O O1 0.37628(16) 0.27865(8) 0.11857(16) 0.0704(5) Uani d 1 . .
N N1 0.38854(15) 0.30447(8) 0.36111(17) 0.0528(4) Uani d 1 . .
H H1 0.357573 0.292390 0.429765 0.063 Uiso calc 1 . .
N N2 0.23792(19) 0.15768(11) 0.1118(2) 0.0780(6) Uani d 1 . .
N N3 0.1406(2) 0.15796(10) -0.0097(2) 0.0673(5) Uani d 1 . .
N N4 0.0587(3) 0.15058(17) -0.1238(3) 0.1192(11) Uani d 1 . .
C C1 0.48107(18) 0.36020(10) 0.4020(2) 0.0494(4) Uani d 1 . .
C C2 0.5065(2) 0.40201(11) 0.2943(2) 0.0614(5) Uani d 1 . .
H H2 0.461604 0.394037 0.188729 0.074 Uiso calc 1 . .
C C3 0.5994(2) 0.45573(12) 0.3457(3) 0.0725(6) Uani d 1 . .
H H3 0.617810 0.483972 0.274916 0.087 Uiso calc 1 . .
C C4 0.6637(2) 0.46685(11) 0.5015(3) 0.0702(6) Uani d 1 . .
C C5 0.6383(2) 0.42787(12) 0.6092(3) 0.0675(6) Uani d 1 . .
H H5 0.681609 0.437309 0.714400 0.081 Uiso calc 1 . .
C C6 0.54707(19) 0.37419(11) 0.5590(2) 0.0569(5) Uani d 1 . .
H H6 0.529166 0.346752 0.631306 0.068 Uiso calc 1 . .
C C7 0.34277(18) 0.26790(10) 0.2280(2) 0.0517(5) Uani d 1 . .
C C8 0.2417(2) 0.21221(12) 0.2228(3) 0.0655(6) Uani d 1 . .
H H8A 0.265262 0.191575 0.324847 0.079 Uiso calc 1 . .
H H8B 0.154166 0.233482 0.193244 0.079 Uiso calc 1 . .
F F2 1.2344(2) 0.51818(12) 0.9845(3) 0.1438(9) Uani d 1 . .
O O2 0.86230(17) 0.27797(9) 0.55142(18) 0.0760(5) Uani d 1 . .
N N5 0.87105(16) 0.30220(9) 0.79296(17) 0.0546(4) Uani d 1 . .
H H5A 0.839332 0.289670 0.860681 0.065 Uiso calc 1 . .
N N6 0.6704(2) 0.18385(13) 0.4918(2) 0.0899(7) Uani d 1 . .
N N7 0.5847(2) 0.14001(11) 0.4654(2) 0.0670(5) Uani d 1 . .
N N8 0.5019(2) 0.10061(15) 0.4215(3) 0.0952(8) Uani d 1 . .
C C9 0.96341(19) 0.35814(10) 0.8354(2) 0.0536(5) Uani d 1 . .
C C10 0.9881(2) 0.40031(12) 0.7283(3) 0.0644(5) Uani d 1 . .
H H10 0.943298 0.392439 0.622692 0.077 Uiso calc 1 . .
C C11 1.0801(3) 0.45421(14) 0.7798(4) 0.0827(7) Uani d 1 . .
H H11 1.098105 0.482845 0.709361 0.099 Uiso calc 1 . .
C C12 1.1445(3) 0.46493(15) 0.9364(4) 0.0907(8) Uani d 1 . .
C C13 1.1195(3) 0.42528(16) 1.0435(3) 0.0904(8) Uani d 1 . .
H H13 1.162906 0.434404 1.148769 0.108 Uiso calc 1 . .
C C14 1.0292(2) 0.37163(13) 0.9929(3) 0.0713(6) Uani d 1 . .
H H14 1.011492 0.343792 1.064795 0.086 Uiso calc 1 . .
C C15 0.82697(19) 0.26628(10) 0.6592(2) 0.0539(5) Uani d 1 . .
C C16 0.7313(2) 0.20775(12) 0.6530(2) 0.0636(5) Uani d 1 . .
H H16A 0.778421 0.169287 0.719587 0.076 Uiso calc 1 . .
H H16B 0.662987 0.224593 0.687969 0.076 Uiso calc 1 . .
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'
F F 0.0727 0.0534 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 127.90(16) ?
C7 N1 H1 . . 116.0 ?
C1 N1 H1 . . 116.0 ?
N3 N2 C8 . . 116.02(19) ?
N4 N3 N2 . . 171.2(3) ?
C2 C1 C6 . . 119.27(18) ?
C2 C1 N1 . . 123.51(17) ?
C6 C1 N1 . . 117.20(17) ?
C3 C2 C1 . . 119.3(2) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C4 C3 C2 . . 119.4(2) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
F1 C4 C5 . . 118.5(2) ?
F1 C4 C3 . . 119.0(2) ?
C5 C4 C3 . . 122.4(2) ?
C4 C5 C6 . . 118.4(2) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
C5 C6 C1 . . 121.11(19) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
O1 C7 N1 . . 124.23(19) ?
O1 C7 C8 . . 122.15(17) ?
N1 C7 C8 . . 113.61(16) ?
N2 C8 C7 . . 110.25(17) ?
N2 C8 H8A . . 109.6 ?
C7 C8 H8A . . 109.6 ?
N2 C8 H8B . . 109.6 ?
C7 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
C15 N5 C9 . . 127.53(16) ?
C15 N5 H5A . . 116.2 ?
C9 N5 H5A . . 116.2 ?
N7 N6 C16 . . 115.87(19) ?
N8 N7 N6 . . 171.2(2) ?
C10 C9 C14 . . 119.6(2) ?
C10 C9 N5 . . 123.08(18) ?
C14 C9 N5 . . 117.35(18) ?
C11 C10 C9 . . 119.4(2) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C12 C11 C10 . . 119.1(3) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C13 C12 F2 . . 119.4(3) ?
C13 C12 C11 . . 122.5(2) ?
F2 C12 C11 . . 118.2(3) ?
C12 C13 C14 . . 118.5(3) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C13 C14 C9 . . 120.9(2) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 119.6 ?
O2 C15 N5 . . 124.02(19) ?
O2 C15 C16 . . 121.86(18) ?
N5 C15 C16 . . 114.10(16) ?
N6 C16 C15 . . 107.63(17) ?
N6 C16 H16A . . 110.2 ?
C15 C16 H16A . . 110.2 ?
N6 C16 H16B . . 110.2 ?
C15 C16 H16B . . 110.2 ?
H16A C16 H16B . . 108.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C4 . 1.353(3) ?
O1 C7 . 1.224(2) ?
N1 C7 . 1.343(2) ?
N1 C1 . 1.409(2) ?
N1 H1 . 0.8600 ?
N2 N3 . 1.220(3) ?
N2 C8 . 1.455(3) ?
N3 N4 . 1.105(3) ?
C1 C2 . 1.389(3) ?
C1 C6 . 1.390(3) ?
C2 C3 . 1.386(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.368(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.359(3) ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.511(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
F2 C12 . 1.358(3) ?
O2 C15 . 1.225(2) ?
N5 C15 . 1.341(2) ?
N5 C9 . 1.411(3) ?
N5 H5A . 0.8600 ?
N6 N7 . 1.202(3) ?
N6 C16 . 1.465(3) ?
N7 N8 . 1.120(3) ?
C9 C10 . 1.385(3) ?
C9 C14 . 1.391(3) ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.374(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.358(4) ?
C13 C14 . 1.368(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.508(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 4_566 0.86 2.17 2.921(2) 146 yes
N5 H5A O2 4_566 0.86 2.13 2.885(2) 146 yes
C4 F1 Cg1 3_666 1.353(3) 3.755(3) 3.563(2) 71.45(2) y
C12 F2 Cg2 3_767 1.358(3) 3.983(3) 3.942(2) 78.45(18) y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . 22.8(3) ?
C7 N1 C1 C6 . . . . -158.76(19) ?
C6 C1 C2 C3 . . . . 1.5(3) ?
N1 C1 C2 C3 . . . . 179.95(18) ?
C1 C2 C3 C4 . . . . -0.4(3) ?
C2 C3 C4 F1 . . . . 179.9(2) ?
C2 C3 C4 C5 . . . . -1.3(4) ?
F1 C4 C5 C6 . . . . -179.38(19) ?
C3 C4 C5 C6 . . . . 1.8(4) ?
C4 C5 C6 C1 . . . . -0.6(3) ?
C2 C1 C6 C5 . . . . -1.0(3) ?
N1 C1 C6 C5 . . . . -179.57(18) ?
C1 N1 C7 O1 . . . . -0.3(3) ?
C1 N1 C7 C8 . . . . -178.95(18) ?
N3 N2 C8 C7 . . . . -106.1(2) ?
O1 C7 C8 N2 . . . . 24.7(3) ?
N1 C7 C8 N2 . . . . -156.63(18) ?
C15 N5 C9 C10 . . . . 23.2(3) ?
C15 N5 C9 C14 . . . . -158.3(2) ?
C14 C9 C10 C11 . . . . 1.4(3) ?
N5 C9 C10 C11 . . . . 179.8(2) ?
C9 C10 C11 C12 . . . . -0.3(4) ?
C10 C11 C12 C13 . . . . -1.2(5) ?
C10 C11 C12 F2 . . . . 180.0(2) ?
F2 C12 C13 C14 . . . . -179.6(3) ?
C11 C12 C13 C14 . . . . 1.6(5) ?
C12 C13 C14 C9 . . . . -0.5(4) ?
C10 C9 C14 C13 . . . . -1.0(4) ?
N5 C9 C14 C13 . . . . -179.5(2) ?
C9 N5 C15 O2 . . . . -0.3(3) ?
C9 N5 C15 C16 . . . . 178.13(18) ?
N7 N6 C16 C15 . . . . -175.4(2) ?
O2 C15 C16 N6 . . . . -13.6(3) ?
N5 C15 C16 N6 . . . . 168.00(19) ?

_cod_database_fobs_code 2244138
