#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:19:26 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266130 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/05/7060543.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_7060543
loop_
_publ_author_name
'Moussallem, Chady'
'Allain, Magali'
'Gohier, Frédéric'
'Frère, Pierre'
_publ_section_title
;
 Preponderant role of pentafluorophenyl moieties for tuning the electronic
 properties of extended benzodifuran-azomethine derivatives
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8647
_journal_page_last               8653
_journal_paper_doi               10.1039/D1NJ01132D
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C32 H10 F15 N3 O2'
_chemical_formula_sum            'C32 H10 F15 N3 O2'
_chemical_formula_weight         753.43
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-09-30T17:39:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2021-02-11 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                69.48(1)
_cell_angle_beta                 66.48(2)
_cell_angle_gamma                63.37(1)
_cell_formula_units_Z            2
_cell_length_a                   11.334(3)
_cell_length_b                   12.585(1)
_cell_length_c                   12.741(3)
_cell_measurement_reflns_used    7595
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.27
_cell_volume                     1456.6(6)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND 3.2g (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1477
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            48840
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         6657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_gt           0.0739
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0259P)²+2.4579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                2905
_reflns_number_total             6657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1nj01132d2.cif
_cod_data_source_block           sad_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7060542--7060544.cif.'
_cod_original_cell_volume        1456.6(5)
_cod_database_code               7060543
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.4915(5) 0.8723(4) 0.9513(4) 0.0429(11) Uani 1 d . . .
C2 C 0.6292(5) 0.8209(4) 0.9351(4) 0.0428(10) Uani 1 d . . .
C3 C 0.6890(4) 0.9064(3) 0.8437(4) 0.0389(10) Uani 1 d . . .
C4 C 0.8219(4) 0.9076(3) 0.7891(4) 0.0408(10) Uani 1 d . . .
H4 H 0.8981 0.845 0.8099 0.049 Uiso 1 calc R . .
C5 C 0.8326(4) 1.0082(3) 0.7020(3) 0.0349(9) Uani 1 d . . .
C6 C 0.7209(4) 1.1040(3) 0.6647(4) 0.0367(10) Uani 1 d . . .
C7 C 0.5874(4) 1.1033(3) 0.7218(4) 0.0417(10) Uani 1 d . . .
H7 H 0.5108 1.1655 0.701 0.05 Uiso 1 calc R . .
C8 C 0.5771(4) 1.0040(4) 0.8109(4) 0.0401(10) Uani 1 d . . .
C9 C 0.9181(4) 1.1397(3) 0.5587(3) 0.0363(10) Uani 1 d . . .
C10 C 0.7807(4) 1.1862(3) 0.5707(4) 0.0378(10) Uani 1 d . . .
C11 C 0.2640(5) 0.8957(4) 1.0438(4) 0.0443(11) Uani 1 d . . .
H11 H 0.2421 0.9745 0.9992 0.053 Uiso 1 calc R . .
C12 C 0.1520(5) 0.8533(4) 1.1250(4) 0.0463(11) Uani 1 d . . .
C13 C 0.1679(6) 0.7338(5) 1.1848(4) 0.0585(13) Uani 1 d . . .
C14 C 0.0564(8) 0.7010(5) 1.2570(5) 0.0736(17) Uani 1 d . . .
C15 C -0.0736(7) 0.7860(7) 1.2717(5) 0.0740(18) Uani 1 d . . .
C16 C -0.0946(6) 0.9048(6) 1.2168(5) 0.0661(15) Uani 1 d . . .
C17 C 0.0177(5) 0.9360(4) 1.1454(4) 0.0537(12) Uani 1 d . . .
C18 C 0.7029(5) 0.6987(4) 0.9953(4) 0.0429(11) Uani 1 d . . .
C19 C 0.7915(5) 0.6802(4) 1.0547(4) 0.0491(11) Uani 1 d . . .
C20 C 0.8606(5) 0.5671(5) 1.1107(4) 0.0587(13) Uani 1 d . . .
C21 C 0.8433(6) 0.4674(4) 1.1064(4) 0.0680(16) Uani 1 d . . .
C22 C 0.7574(6) 0.4811(4) 1.0485(5) 0.0659(15) Uani 1 d . . .
C23 C 0.6873(5) 0.5963(4) 0.9937(4) 0.0541(12) Uani 1 d . . .
C24 C 0.7125(4) 1.2961(3) 0.4931(4) 0.0379(10) Uani 1 d . . .
C25 C 0.6386(5) 1.2925(4) 0.4314(4) 0.0450(11) Uani 1 d . . .
C26 C 0.5740(5) 1.3923(4) 0.3569(4) 0.0497(12) Uani 1 d . . .
C27 C 0.5852(4) 1.5009(4) 0.3417(4) 0.0462(11) Uani 1 d . . .
C28 C 0.6600(4) 1.5085(4) 0.3983(4) 0.0459(11) Uani 1 d . . .
C29 C 0.7218(4) 1.4091(4) 0.4733(4) 0.0401(10) Uani 1 d . . .
C30 C 1.1433(5) 1.1305(4) 0.4823(4) 0.0458(11) Uani 1 d . . .
H30 H 1.1698 1.0516 0.5261 0.055 Uiso 1 calc R . .
C31 C 1.3806(5) 1.1183(5) 0.4192(6) 0.0789(17) Uani 1 d . . .
H31A H 1.4008 1.156 0.4604 0.118 Uiso 1 calc R . .
H31B H 1.44 1.1227 0.3403 0.118 Uiso 1 calc R . .
H31C H 1.3953 1.0347 0.4578 0.118 Uiso 1 calc R . .
C32 C 1.1982(6) 1.3061(4) 0.3544(5) 0.0784(17) Uani 1 d . . .
H32A H 1.1127 1.3285 0.3393 0.118 Uiso 1 calc R . .
H32B H 1.2682 1.3145 0.2816 0.118 Uiso 1 calc R . .
H32C H 1.1868 1.3581 0.4004 0.118 Uiso 1 calc R . .
N1 N 0.3917(4) 0.8279(3) 1.0318(3) 0.0467(9) Uani 1 d . . .
N2 N 1.0147(4) 1.1889(3) 0.4852(3) 0.0420(9) Uani 1 d . . .
N3 N 1.2386(4) 1.1809(3) 0.4179(3) 0.0532(10) Uani 1 d . . .
O1 O 0.4549(3) 0.9849(2) 0.8774(2) 0.0451(7) Uani 1 d . . .
O2 O 0.9543(3) 1.0295(2) 0.6370(2) 0.0398(7) Uani 1 d . . .
F1 F 0.2922(4) 0.6463(3) 1.1735(3) 0.0826(10) Uani 1 d . . .
F2 F 0.0742(4) 0.5850(3) 1.3116(3) 0.1125(14) Uani 1 d . . .
F3 F -0.1844(4) 0.7550(4) 1.3425(3) 0.1167(15) Uani 1 d . . .
F4 F -0.2217(4) 0.9903(4) 1.2337(3) 0.0998(12) Uani 1 d . . .
F5 F -0.0061(3) 1.0549(3) 1.0920(3) 0.0692(8) Uani 1 d . . .
F6 F 0.8114(3) 0.7757(3) 1.0609(3) 0.0705(8) Uani 1 d . . .
F7 F 0.9455(3) 0.5529(3) 1.1684(3) 0.0902(11) Uani 1 d . . .
F8 F 0.9100(4) 0.3564(3) 1.1622(3) 0.1055(13) Uani 1 d . . .
F9 F 0.7398(4) 0.3840(3) 1.0448(3) 0.1082(13) Uani 1 d . . .
F10 F 0.6060(3) 0.6058(2) 0.9351(3) 0.0753(9) Uani 1 d . . .
F11 F 0.6279(3) 1.1856(2) 0.4429(2) 0.0640(8) Uani 1 d . . .
F12 F 0.5024(3) 1.3830(3) 0.3004(3) 0.0781(9) Uani 1 d . . .
F13 F 0.5225(3) 1.6003(2) 0.2694(2) 0.0686(8) Uani 1 d . . .
F14 F 0.6689(3) 1.6161(2) 0.3835(3) 0.0674(8) Uani 1 d . . .
F15 F 0.7860(3) 1.4229(2) 0.5330(2) 0.0603(7) Uani 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 0 '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 0.006 '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
C2 C1 N1 127.9(4) . . ?
C2 C1 O1 111.9(4) . . ?
N1 C1 O1 120.2(4) . . ?
C1 C2 C3 106.7(3) . . ?
C1 C2 C18 125.8(4) . . ?
C3 C2 C18 127.5(4) . . ?
C4 C3 C8 120.3(4) . . ?
C4 C3 C2 134.7(4) . . ?
C8 C3 C2 105.0(4) . . ?
C5 C4 C3 115.2(4) . . ?
C5 C4 H4 122.4 . . ?
C3 C4 H4 122.4 . . ?
C4 C5 O2 125.2(3) . . ?
C4 C5 C6 124.7(4) . . ?
O2 C5 C6 110.1(3) . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 C10 135.0(4) . . ?
C5 C6 C10 105.3(3) . . ?
C8 C7 C6 115.3(4) . . ?
C8 C7 H7 122.4 . . ?
C6 C7 H7 122.4 . . ?
C7 C8 O1 124.5(4) . . ?
C7 C8 C3 124.8(4) . . ?
O1 C8 C3 110.7(3) . . ?
N2 C9 C10 128.2(4) . . ?
N2 C9 O2 120.4(3) . . ?
C10 C9 O2 111.3(3) . . ?
C9 C10 C6 107.3(3) . . ?
C9 C10 C24 124.3(4) . . ?
C6 C10 C24 128.2(4) . . ?
N1 C11 C12 122.3(4) . . ?
N1 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C17 C12 C13 115.6(4) . . ?
C17 C12 C11 119.1(4) . . ?
C13 C12 C11 125.2(5) . . ?
F1 C13 C14 117.2(5) . . ?
F1 C13 C12 121.3(4) . . ?
C14 C13 C12 121.5(5) . . ?
F2 C14 C15 119.4(6) . . ?
F2 C14 C13 120.4(6) . . ?
C15 C14 C13 120.2(5) . . ?
F3 C15 C14 120.9(6) . . ?
F3 C15 C16 118.5(6) . . ?
C14 C15 C16 120.6(5) . . ?
F4 C16 C15 121.3(5) . . ?
F4 C16 C17 120.3(5) . . ?
C15 C16 C17 118.4(6) . . ?
F5 C17 C16 117.2(5) . . ?
F5 C17 C12 119.1(4) . . ?
C16 C17 C12 123.6(5) . . ?
C19 C18 C23 116.6(4) . . ?
C19 C18 C2 122.2(4) . . ?
C23 C18 C2 121.3(4) . . ?
F6 C19 C20 117.2(4) . . ?
F6 C19 C18 120.1(4) . . ?
C20 C19 C18 122.7(5) . . ?
F7 C20 C19 120.9(5) . . ?
F7 C20 C21 120.0(5) . . ?
C19 C20 C21 119.1(5) . . ?
F8 C21 C22 120.4(6) . . ?
F8 C21 C20 119.2(6) . . ?
C22 C21 C20 120.4(4) . . ?
F9 C22 C21 120.4(5) . . ?
F9 C22 C23 120.0(6) . . ?
C21 C22 C23 119.6(5) . . ?
F10 C23 C18 120.4(4) . . ?
F10 C23 C22 117.8(5) . . ?
C18 C23 C22 121.8(5) . . ?
C25 C24 C29 115.4(4) . . ?
C25 C24 C10 121.5(4) . . ?
C29 C24 C10 123.1(4) . . ?
F11 C25 C24 119.2(4) . . ?
F11 C25 C26 117.0(4) . . ?
C24 C25 C26 123.8(4) . . ?
F12 C26 C27 120.8(4) . . ?
F12 C26 C25 120.9(4) . . ?
C27 C26 C25 118.4(4) . . ?
F13 C27 C28 120.4(4) . . ?
F13 C27 C26 119.6(4) . . ?
C28 C27 C26 120.0(4) . . ?
F14 C28 C27 119.3(4) . . ?
F14 C28 C29 119.8(4) . . ?
C27 C28 C29 120.9(4) . . ?
F15 C29 C28 118.7(4) . . ?
F15 C29 C24 119.7(4) . . ?
C28 C29 C24 121.5(4) . . ?
N2 C30 N3 121.6(4) . . ?
N2 C30 H30 119.2 . . ?
N3 C30 H30 119.2 . . ?
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N3 C32 H32A 109.5 . . ?
N3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C11 N1 C1 119.2(4) . . ?
C30 N2 C9 120.4(3) . . ?
C30 N3 C31 121.6(4) . . ?
C30 N3 C32 120.0(4) . . ?
C31 N3 C32 118.0(4) . . ?
C8 O1 C1 105.7(3) . . ?
C5 O2 C9 105.9(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
C1 C2 1.352(6) . ?
C1 N1 1.371(5) . ?
C1 O1 1.385(4) . ?
C2 C3 1.455(5) . ?
C2 C18 1.478(6) . ?
C3 C4 1.389(6) . ?
C3 C8 1.399(5) . ?
C4 C5 1.376(5) . ?
C4 H4 0.93 . ?
C5 O2 1.388(5) . ?
C5 C6 1.411(5) . ?
C6 C7 1.396(6) . ?
C6 C10 1.440(5) . ?
C7 C8 1.376(5) . ?
C7 H7 0.93 . ?
C8 O1 1.383(5) . ?
C9 N2 1.357(5) . ?
C9 C10 1.359(5) . ?
C9 O2 1.391(4) . ?
C10 C24 1.478(5) . ?
C11 N1 1.286(5) . ?
C11 C12 1.463(6) . ?
C11 H11 0.93 . ?
C12 C17 1.386(7) . ?
C12 C13 1.391(6) . ?
C13 F1 1.333(6) . ?
C13 C14 1.374(7) . ?
C14 F2 1.338(6) . ?
C14 C15 1.363(8) . ?
C15 F3 1.353(6) . ?
C15 C16 1.365(8) . ?
C16 F4 1.344(6) . ?
C16 C17 1.369(7) . ?
C17 F5 1.358(5) . ?
C18 C19 1.381(6) . ?
C18 C23 1.385(6) . ?
C19 F6 1.351(5) . ?
C19 C20 1.372(6) . ?
C20 F7 1.347(6) . ?
C20 C21 1.377(7) . ?
C21 F8 1.347(5) . ?
C21 C22 1.362(8) . ?
C22 F9 1.341(6) . ?
C22 C23 1.386(7) . ?
C23 F10 1.346(5) . ?
C24 C25 1.381(6) . ?
C24 C29 1.399(5) . ?
C25 F11 1.357(5) . ?
C25 C26 1.382(6) . ?
C26 F12 1.342(5) . ?
C26 C27 1.368(6) . ?
C27 F13 1.354(4) . ?
C27 C28 1.363(6) . ?
C28 F14 1.344(5) . ?
C28 C29 1.371(6) . ?
C29 F15 1.335(5) . ?
C30 N2 1.297(5) . ?
C30 N3 1.336(5) . ?
C30 H30 0.93 . ?
C31 N3 1.444(6) . ?
C31 H31A 0.96 . ?
C31 H31B 0.96 . ?
C31 H31C 0.96 . ?
C32 N3 1.450(6) . ?
C32 H32A 0.96 . ?
C32 H32B 0.96 . ?
C32 H32C 0.96 . ?
