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#$Date: 2020-03-04 02:30:23 +0200 (Wed, 04 Mar 2020) $
#$Revision: 248688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038017.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_4038017
loop_
_publ_author_name
'Khan, Mehebub Ali'
'Ghosh, Soumen'
'Bera, Sachinath'
'Hoque, Anamika'
'Sk, Ismail'
'Ansari, Shagufi Naz'
'Mobin, Shaikh M.'
'Alam, Md Akhtarul'
_publ_section_title
;
 A Crystallographic Elucidation of Stimuli Controlled Molecular Rotation
 for Reversible Sol-Gel Transformation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02944
_journal_year                    2020
_chemical_formula_sum            'C21 H15 F5 N3 O3'
_chemical_formula_weight         452.36
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.347(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9689(4)
_cell_length_b                   24.8459(12)
_cell_length_c                   12.2965(6)
_cell_measurement_reflns_used    1081
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.87
_cell_measurement_theta_min      2.89
_cell_volume                     2079.88(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19757
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.9590
_exptl_crystal_colour            lightyellow
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rodshaped
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0640
_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)+(0.0823P)²+0.9847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1950
_reflns_number_gt                2601
_reflns_number_total             3664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02944_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038017
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C14 C 0.2953(4) 0.33616(12) 0.5617(3) 0.0587(8) Uani 1 1 d . . .
C15 C 0.3319(5) 0.28567(12) 0.6104(3) 0.0638(8) Uani 1 1 d . . .
C16 C 0.3999(4) 0.28131(13) 0.7245(3) 0.0648(8) Uani 1 1 d . . .
C17 C 0.4312(5) 0.32716(14) 0.7899(3) 0.0640(8) Uani 1 1 d . . .
C18 C 0.3939(4) 0.37728(13) 0.7396(2) 0.0578(7) Uani 1 1 d . . .
C13 C 0.3255(4) 0.38388(12) 0.6244(2) 0.0535(7) Uani 1 1 d . . .
C12 C 0.2892(4) 0.43898(12) 0.5791(3) 0.0587(7) Uani 1 1 d . . .
H12 H 0.2927 0.4677 0.6280 0.070 Uiso 1 1 calc R . .
C11 C 0.1757(4) 0.51439(12) 0.3326(2) 0.0580(7) Uani 1 1 d . . .
C10 C 0.1441(4) 0.57307(11) 0.3016(2) 0.0508(7) Uani 1 1 d . . .
C1 C 0.0781(4) 0.58684(12) 0.1857(2) 0.0564(7) Uani 1 1 d . . .
C2 C 0.0470(4) 0.64021(13) 0.1544(2) 0.0601(8) Uani 1 1 d . . .
H2 H 0.0012 0.6485 0.0796 0.072 Uiso 1 1 calc R . .
C3 C 0.0834(4) 0.68255(12) 0.2339(2) 0.0537(7) Uani 1 1 d . . .
C4 C 0.0553(5) 0.73816(13) 0.2035(3) 0.0667(8) Uani 1 1 d . . .
H4 H 0.0083 0.7474 0.1293 0.080 Uiso 1 1 calc R . .
C5 C 0.0967(5) 0.77789(14) 0.2825(3) 0.0748(9) Uani 1 1 d . . .
H5 H 0.0782 0.8137 0.2610 0.090 Uiso 1 1 calc R . .
C6 C 0.1672(5) 0.76507(14) 0.3961(3) 0.0734(9) Uani 1 1 d . . .
H6 H 0.1953 0.7924 0.4488 0.088 Uiso 1 1 calc R . .
C7 C 0.1939(5) 0.71239(13) 0.4285(3) 0.0658(8) Uani 1 1 d . . .
H7 H 0.2394 0.7043 0.5034 0.079 Uiso 1 1 calc R . .
C8 C 0.1528(4) 0.66961(12) 0.3489(2) 0.0533(7) Uani 1 1 d . . .
C9 C 0.1797(4) 0.61429(12) 0.3798(2) 0.0548(7) Uani 1 1 d . . .
H9 H 0.2225 0.6056 0.4546 0.066 Uiso 1 1 calc R . .
C20 C 0.3165(8) 0.5644(2) 0.8703(4) 0.1191(17) Uani 1 1 d . . .
H20C H 0.3582 0.5682 0.9495 0.179 Uiso 1 1 calc R . .
H20B H 0.2968 0.5269 0.8518 0.179 Uiso 1 1 calc R . .
H20A H 0.1956 0.5836 0.8451 0.179 Uiso 1 1 calc R . .
C19 C 0.6535(7) 0.6048(2) 0.8875(4) 0.1174(17) Uani 1 1 d . . .
H19B H 0.6452 0.6026 0.9643 0.176 Uiso 1 1 calc R . .
H19A H 0.6775 0.6415 0.8693 0.176 Uiso 1 1 calc R . .
H19C H 0.7592 0.5825 0.8751 0.176 Uiso 1 1 calc R . .
C21 C 0.4428(6) 0.58557(13) 0.7066(3) 0.0731(9) Uani 1 1 d . . .
H21 H 0.5434 0.5995 0.6761 0.088 Uiso 1 1 calc R . .
N2 N 0.2526(4) 0.44815(10) 0.4735(2) 0.0601(6) Uani 1 1 d . . .
N3 N 0.2224(4) 0.50176(10) 0.4435(2) 0.0601(7) Uani 1 1 d . . .
H3 H 0.2327 0.5265 0.4933 0.072 Uiso 1 1 calc R . .
N1 N 0.4668(4) 0.58624(11) 0.8163(2) 0.0716(8) Uani 1 1 d . . .
O1 O 0.1583(4) 0.47891(9) 0.25946(19) 0.0813(7) Uani 1 1 d . . .
O2 O 0.0439(4) 0.54862(10) 0.10344(18) 0.0783(7) Uani 1 1 d . . .
O3 O 0.2944(4) 0.56759(12) 0.6411(2) 0.0977(9) Uani 1 1 d . . .
F1 F 0.2290(3) 0.33774(8) 0.45030(16) 0.0861(7) Uani 1 1 d . . .
F2 F 0.3003(3) 0.24090(8) 0.54688(19) 0.0882(6) Uani 1 1 d . . .
F3 F 0.4351(3) 0.23221(8) 0.7728(2) 0.0918(7) Uani 1 1 d . . .
F4 F 0.4984(4) 0.32337(10) 0.90110(16) 0.0945(7) Uani 1 1 d . . .
F5 F 0.4261(3) 0.42147(8) 0.80634(15) 0.0791(6) Uani 1 1 d . . .
H1 H 0.097(7) 0.515(2) 0.148(4) 0.146(19) 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'
F F 0.0171 0.0103 '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
F1 C14 C15 117.1(3) . . ?
F1 C14 C13 120.7(3) . . ?
C15 C14 C13 122.2(3) . . ?
F2 C15 C16 120.0(3) . . ?
F2 C15 C14 120.1(3) . . ?
C16 C15 C14 119.9(3) . . ?
F3 C16 C17 119.7(3) . . ?
F3 C16 C15 120.3(3) . . ?
C17 C16 C15 120.1(3) . . ?
F4 C17 C16 120.5(3) . . ?
F4 C17 C18 120.3(3) . . ?
C16 C17 C18 119.2(3) . . ?
F5 C18 C17 117.6(3) . . ?
F5 C18 C13 119.4(3) . . ?
C17 C18 C13 123.0(3) . . ?
C18 C13 C14 115.7(3) . . ?
C18 C13 C12 118.8(3) . . ?
C14 C13 C12 125.5(3) . . ?
N2 C12 C13 121.6(3) . . ?
N2 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
O1 C11 N3 121.5(3) . . ?
O1 C11 C10 120.9(3) . . ?
N3 C11 C10 117.6(3) . . ?
C9 C10 C1 118.7(3) . . ?
C9 C10 C11 122.8(3) . . ?
C1 C10 C11 118.5(3) . . ?
O2 C1 C2 117.8(3) . . ?
O2 C1 C10 122.2(3) . . ?
C2 C1 C10 120.0(3) . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C8 119.1(3) . . ?
C2 C3 C4 122.7(3) . . ?
C8 C3 C4 118.2(3) . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C3 118.5(3) . . ?
C9 C8 C7 122.5(3) . . ?
C3 C8 C7 119.0(3) . . ?
C10 C9 C8 122.1(3) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
N1 C20 H20C 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
N1 C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
O3 C21 N1 124.6(4) . . ?
O3 C21 H21 117.7 . . ?
N1 C21 H21 117.7 . . ?
C12 N2 N3 115.1(3) . . ?
C11 N3 N2 118.4(3) . . ?
C11 N3 H3 120.8 . . ?
N2 N3 H3 120.8 . . ?
C21 N1 C20 120.8(3) . . ?
C21 N1 C19 120.7(4) . . ?
C20 N1 C19 118.3(3) . . ?
C1 O2 H1 100(3) . . ?
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
C14 F1 1.349(4) . ?
C14 C15 1.390(4) . ?
C14 C13 1.405(4) . ?
C15 F2 1.350(4) . ?
C15 C16 1.386(5) . ?
C16 F3 1.356(4) . ?
C16 C17 1.384(5) . ?
C17 F4 1.351(4) . ?
C17 C18 1.390(4) . ?
C18 F5 1.360(4) . ?
C18 C13 1.405(4) . ?
C13 C12 1.479(4) . ?
C12 N2 1.290(4) . ?
C12 H12 0.9300 . ?
C11 O1 1.246(4) . ?
C11 N3 1.369(4) . ?
C11 C10 1.511(4) . ?
C10 C9 1.390(4) . ?
C10 C1 1.442(4) . ?
C1 O2 1.370(4) . ?
C1 C2 1.385(4) . ?
C2 C3 1.421(4) . ?
C2 H2 0.9300 . ?
C3 C8 1.430(4) . ?
C3 C4 1.434(4) . ?
C4 C5 1.371(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.432(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.427(4) . ?
C9 H9 0.9300 . ?
C20 N1 1.460(5) . ?
C20 H20C 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20A 0.9600 . ?
C19 N1 1.478(5) . ?
C19 H19B 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
C21 O3 1.250(4) . ?
C21 N1 1.323(4) . ?
C21 H21 0.9300 . ?
N2 N3 1.386(3) . ?
N3 H3 0.8600 . ?
O2 H1 1.02(5) . ?
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
_geom_torsion_publ_flag
F1 C14 C15 F2 -0.3(4) . . . . ?
C13 C14 C15 F2 179.9(3) . . . . ?
F1 C14 C15 C16 -179.9(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
F2 C15 C16 F3 0.1(5) . . . . ?
C14 C15 C16 F3 179.7(3) . . . . ?
F2 C15 C16 C17 -179.6(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
F3 C16 C17 F4 0.7(5) . . . . ?
C15 C16 C17 F4 -179.6(3) . . . . ?
F3 C16 C17 C18 -179.8(3) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
F4 C17 C18 F5 -0.5(4) . . . . ?
C16 C17 C18 F5 179.9(3) . . . . ?
F4 C17 C18 C13 179.4(3) . . . . ?
C16 C17 C18 C13 -0.1(5) . . . . ?
F5 C18 C13 C14 -179.7(2) . . . . ?
C17 C18 C13 C14 0.3(4) . . . . ?
F5 C18 C13 C12 -0.4(4) . . . . ?
C17 C18 C13 C12 179.6(3) . . . . ?
F1 C14 C13 C18 179.7(3) . . . . ?
C15 C14 C13 C18 -0.4(4) . . . . ?
F1 C14 C13 C12 0.5(5) . . . . ?
C15 C14 C13 C12 -179.6(3) . . . . ?
C18 C13 C12 N2 170.3(3) . . . . ?
C14 C13 C12 N2 -10.5(4) . . . . ?
O1 C11 C10 C9 -173.8(3) . . . . ?
N3 C11 C10 C9 6.7(4) . . . . ?
O1 C11 C10 C1 4.8(4) . . . . ?
N3 C11 C10 C1 -174.7(3) . . . . ?
C9 C10 C1 O2 178.6(3) . . . . ?
C11 C10 C1 O2 -0.1(4) . . . . ?
C9 C10 C1 C2 -1.5(4) . . . . ?
C11 C10 C1 C2 179.8(3) . . . . ?
O2 C1 C2 C3 -178.4(3) . . . . ?
C10 C1 C2 C3 1.7(4) . . . . ?
C1 C2 C3 C8 -0.4(4) . . . . ?
C1 C2 C3 C4 179.0(3) . . . . ?
C2 C3 C4 C5 -178.4(3) . . . . ?
C8 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C2 C3 C8 C9 -1.0(4) . . . . ?
C4 C3 C8 C9 179.6(3) . . . . ?
C2 C3 C8 C7 178.5(3) . . . . ?
C4 C3 C8 C7 -0.9(4) . . . . ?
C6 C7 C8 C9 179.7(3) . . . . ?
C6 C7 C8 C3 0.2(4) . . . . ?
C1 C10 C9 C8 0.1(4) . . . . ?
C11 C10 C9 C8 178.8(3) . . . . ?
C3 C8 C9 C10 1.1(4) . . . . ?
C7 C8 C9 C10 -178.4(3) . . . . ?
C13 C12 N2 N3 -179.8(2) . . . . ?
O1 C11 N3 N2 0.7(4) . . . . ?
C10 C11 N3 N2 -179.8(2) . . . . ?
C12 N2 N3 C11 -177.6(3) . . . . ?
O3 C21 N1 C20 0.9(6) . . . . ?
O3 C21 N1 C19 175.7(4) . . . . ?
