#------------------------------------------------------------------------------
#$Date: 2024-09-29 02:59:04 +0200 (Sun 29 de Sep de 2024) $
#$Revision: 294938 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/94/7249404.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_7249404
loop_
_publ_author_name
'Khorasani, Fereshteh'
'Ranjbar-Karimi, Reza'
'Mohammadiannejad, Kazem'
_publ_section_title
;
 Utilizing perhalopyridine-based alkynes as suitable precursors for the
 synthesis of novel poly(1,2,3-triazolyl)-substituted perhalopyridines
;
_journal_issue                   42
_journal_name_full               'RSC Advances'
_journal_page_first              30873
_journal_page_last               30885
_journal_paper_doi               10.1039/D4RA05861E
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C14 H9 F2 N O3'
_chemical_formula_sum            'C14 H9 F2 N O3'
_chemical_formula_weight         277.22
_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
_audit_creation_date             2024-04-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.91(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.806(8)
_cell_length_b                   4.4215(9)
_cell_length_c                   16.055(3)
_cell_measurement_reflns_used    5882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.995
_cell_measurement_theta_min      2.250
_cell_volume                     1285.3(7)
_computing_cell_refinement       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    PLATON
_computing_publication_material  DIAMOND
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  Marresearch
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5882
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.250
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.03288
_exptl_absorpt_correction_T_min  0.97557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, R. H. (1995).Acta Cryst.A51,33+-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0786
_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)+(0.0446P)²+1.2663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1623
_reflns_number_total             2214
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra05861e2.cif
_cod_data_source_block           abs
_cod_database_code               7249404
_shelx_shelxl_version_number     2016/6
_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
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C013(H01A,H01B), C018(H01C,H01D), C019(H01E,H01F)
2.b :
 C015(H015), C016(H016), C022(H022)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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
F001 F 0.58125(11) 0.5351(5) 0.14474(15) 0.0679(7) Uani 1 1 d . . . . .
F002 F 0.72404(12) 0.0610(5) 0.00746(15) 0.0704(7) Uani 1 1 d . . . . .
C003 C 0.7074(2) 0.6365(8) 0.1914(2) 0.0496(9) Uani 1 1 d . . . . .
C004 C 0.64565(19) 0.4909(8) 0.1364(2) 0.0502(9) Uani 1 1 d . . . . .
O005 O 0.83826(13) 0.3740(6) 0.11336(18) 0.0622(7) Uani 1 1 d . . . . .
N006 N 0.77162(16) 0.6052(7) 0.1848(2) 0.0528(8) Uani 1 1 d . . . . .
O007 O 0.70111(14) 0.8205(6) 0.25470(18) 0.0659(8) Uani 1 1 d . . . . .
C008 C 0.77437(19) 0.4192(8) 0.1228(2) 0.0508(9) Uani 1 1 d . . . . .
C009 C 0.7144(2) 0.2583(8) 0.0656(2) 0.0501(9) Uani 1 1 d . . . . .
O010 O 0.58320(14) 0.1522(7) 0.02247(17) 0.0652(8) Uani 1 1 d . . . . .
C011 C 0.64732(19) 0.2924(8) 0.0711(2) 0.0483(8) Uani 1 1 d . . . . .
C012 C 0.9596(2) 0.4947(11) 0.1434(3) 0.0719(12) Uani 1 1 d . . . . .
C013 C 0.5721(2) 0.0039(10) -0.0614(3) 0.0642(11) Uani 1 1 d . . . . .
H01A H 0.608495 -0.155363 -0.049538 0.077 Uiso 1 1 calc R U . . .
H01B H 0.523563 -0.089018 -0.086196 0.077 Uiso 1 1 calc R U . . .
C014 C 0.8131(2) 0.7540(10) 0.3849(3) 0.0629(11) Uani 1 1 d . . . . .
C015 C 0.8506(3) 0.5940(12) 0.4417(3) 0.0833(14) Uani 1 1 d . . . . .
H015 H 0.880747 0.465136 0.487418 0.100 Uiso 1 1 calc R U . . .
C016 C 0.5829(2) 0.3726(12) -0.1812(3) 0.0764(12) Uani 1 1 d . . . . .
H016 H 0.586890 0.503736 -0.224226 0.092 Uiso 1 1 calc R U . . .
C017 C 0.5779(2) 0.2086(10) -0.1273(3) 0.0604(10) Uani 1 1 d . . . . .
C018 C 0.7666(2) 0.9633(9) 0.3173(3) 0.0676(11) Uani 1 1 d . . . . .
H01C H 0.753307 1.128981 0.347269 0.081 Uiso 1 1 calc R U . . .
H01D H 0.793822 1.046746 0.284152 0.081 Uiso 1 1 calc R U . . .
C019 C 0.8988(2) 0.5609(10) 0.1686(3) 0.0696(12) Uani 1 1 d . . . . .
H01E H 0.912581 0.517146 0.232612 0.083 Uiso 1 1 calc R U . . .
H01F H 0.885306 0.772775 0.157971 0.083 Uiso 1 1 calc R U . . .
C022 C 1.0084(3) 0.4465(14) 0.1237(4) 0.0999(17) Uani 1 1 d . . . . .
H022 H 1.047801 0.407476 0.107789 0.120 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
N006 C003 C004 122.9(3) . . ?
N006 C003 O007 120.6(3) . . ?
O007 C003 C004 116.5(3) . . ?
F001 C004 C011 118.9(3) . . ?
C003 C004 F001 120.6(3) . . ?
C003 C004 C011 120.5(3) . . ?
C008 O005 C019 115.7(3) . . ?
C008 N006 C003 117.6(3) . . ?
C003 O007 C018 117.6(3) . . ?
O005 C008 C009 116.5(3) . . ?
N006 C008 O005 120.6(3) . . ?
N006 C008 C009 122.9(3) . . ?
F002 C009 C008 118.2(3) . . ?
F002 C009 C011 121.9(3) . . ?
C008 C009 C011 119.9(3) . . ?
C011 O010 C013 120.4(3) . . ?
C009 C011 C004 116.1(3) . . ?
O010 C011 C004 115.3(3) . . ?
O010 C011 C009 128.5(3) . . ?
C022 C012 C019 179.0(6) . . ?
O010 C013 H01A 109.2 . . ?
O010 C013 H01B 109.2 . . ?
H01A C013 H01B 107.9 . . ?
C017 C013 O010 112.2(3) . . ?
C017 C013 H01A 109.2 . . ?
C017 C013 H01B 109.2 . . ?
C015 C014 C018 177.4(5) . . ?
C014 C015 H015 180.0 . . ?
C017 C016 H016 180.0 . . ?
C016 C017 C013 179.3(5) . . ?
O007 C018 C014 111.6(3) . . ?
O007 C018 H01C 109.3 . . ?
O007 C018 H01D 109.3 . . ?
C014 C018 H01C 109.3 . . ?
C014 C018 H01D 109.3 . . ?
H01C C018 H01D 108.0 . . ?
O005 C019 C012 107.1(3) . . ?
O005 C019 H01E 110.3 . . ?
O005 C019 H01F 110.3 . . ?
C012 C019 H01E 110.3 . . ?
C012 C019 H01F 110.3 . . ?
H01E C019 H01F 108.6 . . ?
C012 C022 H022 180.0 . . ?
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
F001 C004 1.349(4) . ?
F002 C009 1.347(4) . ?
C003 C004 1.347(5) . ?
C003 N006 1.326(4) . ?
C003 O007 1.346(4) . ?
C004 C011 1.379(5) . ?
O005 C008 1.349(4) . ?
O005 C019 1.430(5) . ?
N006 C008 1.310(4) . ?
O007 C018 1.427(5) . ?
C008 C009 1.370(5) . ?
C009 C011 1.374(5) . ?
O010 C011 1.343(4) . ?
O010 C013 1.433(4) . ?
C012 C019 1.448(6) . ?
C012 C022 1.152(6) . ?
C013 H01A 0.9700 . ?
C013 H01B 0.9700 . ?
C013 C017 1.432(6) . ?
C014 C015 1.155(6) . ?
C014 C018 1.440(6) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C017 1.163(6) . ?
C018 H01C 0.9700 . ?
C018 H01D 0.9700 . ?
C019 H01E 0.9700 . ?
C019 H01F 0.9700 . ?
C022 H022 0.9300 . ?
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
F001 C004 C011 C009 179.6(3) . . . . ?
F001 C004 C011 O010 -1.8(5) . . . . ?
F002 C009 C011 C004 176.9(3) . . . . ?
F002 C009 C011 O010 -1.4(6) . . . . ?
C003 C004 C011 C009 -0.9(5) . . . . ?
C003 C004 C011 O010 177.7(3) . . . . ?
C003 N006 C008 O005 -179.1(3) . . . . ?
C003 N006 C008 C009 -0.1(5) . . . . ?
C003 O007 C018 C014 -74.8(4) . . . . ?
C004 C003 N006 C008 -1.3(5) . . . . ?
C004 C003 O007 C018 176.4(3) . . . . ?
O005 C008 C009 F002 2.5(5) . . . . ?
O005 C008 C009 C011 -180.0(3) . . . . ?
N006 C003 C004 F001 -178.7(3) . . . . ?
N006 C003 C004 C011 1.8(6) . . . . ?
N006 C003 O007 C018 -3.9(5) . . . . ?
N006 C008 C009 F002 -176.5(3) . . . . ?
N006 C008 C009 C011 1.0(6) . . . . ?
O007 C003 C004 F001 1.0(5) . . . . ?
O007 C003 C004 C011 -178.5(3) . . . . ?
O007 C003 N006 C008 179.0(3) . . . . ?
C008 O005 C019 C012 -175.6(3) . . . . ?
C008 C009 C011 C004 -0.5(5) . . . . ?
C008 C009 C011 O010 -178.8(3) . . . . ?
C011 O010 C013 C017 -60.4(5) . . . . ?
C013 O010 C011 C004 163.8(3) . . . . ?
C013 O010 C011 C009 -17.9(6) . . . . ?
C019 O005 C008 N006 -5.6(5) . . . . ?
C019 O005 C008 C009 175.3(3) . . . . ?
