#------------------------------------------------------------------------------
#$Date: 2021-05-27 06:33:13 +0200 (Thu 27 de May de 2021) $
#$Revision: 265534 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/29/7242924.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_7242924
loop_
_publ_author_name
'Akhmadiev, Nail S.'
'Mescheryakova, Ekaterina S.'
'Akhmetova, Vnira R.'
'Ibragimov, Askhat G.'
_publ_section_title
;
 Metal-free multicomponent synthesis of novel macrocyclic tetrathiadienes
 with cyano and amino groups
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              18768
_journal_page_last               18775
_journal_paper_doi               10.1039/D1RA02616J
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C10 H5 F N2'
_chemical_formula_sum            'C10 H5 F N2'
_chemical_formula_weight         172.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2020-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-20 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                107.194(8)
_cell_angle_beta                 99.036(9)
_cell_angle_gamma                102.848(8)
_cell_formula_units_Z            2
_cell_length_a                   6.9541(7)
_cell_length_b                   7.3664(5)
_cell_length_c                   9.1492(10)
_cell_measurement_reflns_used    1411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0147
_cell_measurement_theta_min      2.3951
_cell_volume                     423.86(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -92.00  -12.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.6098  -57.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00   13.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.6098  -19.0000   30.0000 110

#__ type_ start__ end____ width___ exp.time_
  3 omega  -71.00  -33.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.6098  115.0000   58.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -42.00   36.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.6098   57.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega    5.00   76.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -       24.5473 -115.0000  -58.0000 71
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0428398000
_diffrn_orient_matrix_UB_12      0.0182415000
_diffrn_orient_matrix_UB_13      0.0804229000
_diffrn_orient_matrix_UB_21      -0.0955171000
_diffrn_orient_matrix_UB_22      0.0020252000
_diffrn_orient_matrix_UB_23      0.0174240000
_diffrn_orient_matrix_UB_31      -0.0254958000
_diffrn_orient_matrix_UB_32      -0.1035371000
_diffrn_orient_matrix_UB_33      -0.0146284000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3675
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.084
_diffrn_reflns_theta_min         2.400
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       prizm
_exptl_crystal_F_000             176.0
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.17(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0460
_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)+(0.0623P)²+0.0418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1863
_reflns_number_total             2396
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra02616j2.cif
_cod_data_source_block           ans-257
_cod_original_cell_volume        423.86(7)
_cod_database_code               7242924
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
;
loop_
_space_group_symop_operation_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_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
C1 C 0.45413(17) 0.75582(15) 0.51296(12) 0.0371(3) Uani 1 1 d . . . . .
C2 C 0.51128(17) 0.89025(16) 0.67488(13) 0.0383(3) Uani 1 1 d . . . . .
C3 C 0.69530(17) 0.99448(16) 0.77126(12) 0.0379(3) Uani 1 1 d . . . . .
C4 C 0.5893(2) 0.71981(19) 0.41732(15) 0.0462(3) Uani 1 1 d . . . . .
C5 C 0.70847(18) 1.11995(18) 0.92842(14) 0.0460(3) Uani 1 1 d . . . . .
C6 C 0.88627(18) 0.99413(18) 0.73218(14) 0.0470(3) Uani 1 1 d . . . . .
F7 F 0.24899(18) 0.36543(14) 0.05995(10) 0.0871(4) Uani 1 1 d . . . . .
N8 N 0.7196(2) 1.22080(19) 1.05250(14) 0.0655(4) Uani 1 1 d . . . . .
C9 C 0.5198(2) 0.5884(2) 0.26389(16) 0.0562(4) Uani 1 1 d . . . . .
C10 C 0.2480(2) 0.65921(19) 0.44985(15) 0.0491(3) Uani 1 1 d . . . . .
N11 N 1.0405(2) 0.9958(2) 0.70443(17) 0.0743(4) Uani 1 1 d . . . . .
C12 C 0.1775(2) 0.5278(2) 0.29733(18) 0.0592(4) Uani 1 1 d . . . . .
C13 C 0.3156(3) 0.49484(19) 0.20890(15) 0.0563(4) Uani 1 1 d . . . . .
H2 H 0.399(2) 0.902(2) 0.7178(17) 0.046(3) Uiso 1 1 d . . . . .
H10 H 0.153(3) 0.684(2) 0.515(2) 0.065(4) Uiso 1 1 d . . . . .
H9 H 0.609(3) 0.559(3) 0.194(2) 0.077(5) Uiso 1 1 d . . . . .
H12 H 0.037(3) 0.462(3) 0.253(2) 0.087(6) Uiso 1 1 d . . . . .
H4 H 0.735(3) 0.784(2) 0.4552(18) 0.059(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'
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
C4 C1 C2 124.93(11) . . ?
C10 C1 C2 116.48(10) . . ?
C10 C1 C4 118.59(11) . . ?
C3 C2 C1 130.87(10) . . ?
C2 C3 C5 119.31(10) . . ?
C2 C3 C6 125.82(10) . . ?
C6 C3 C5 114.87(10) . . ?
C9 C4 C1 120.60(13) . . ?
N8 C5 C3 179.37(14) . . ?
N11 C6 C3 178.51(14) . . ?
C13 C9 C4 118.28(13) . . ?
C12 C10 C1 121.17(13) . . ?
C13 C12 C10 118.21(14) . . ?
F7 C13 C9 118.04(14) . . ?
F7 C13 C12 118.83(14) . . ?
C12 C13 C9 123.13(12) . . ?
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 1.4512(14) . ?
C1 C4 1.3970(16) . ?
C1 C10 1.3923(16) . ?
C2 C3 1.3465(16) . ?
C3 C5 1.4371(15) . ?
C3 C6 1.4289(16) . ?
C4 C9 1.3844(18) . ?
C5 N8 1.1380(16) . ?
C6 N11 1.1384(18) . ?
F7 C13 1.3482(14) . ?
C9 C13 1.371(2) . ?
C10 C12 1.3785(18) . ?
C12 C13 1.366(2) . ?
