#------------------------------------------------------------------------------
#$Date: 2019-10-28 12:16:03 +0200 (Mon, 28 Oct 2019) $
#$Revision: 220067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/49/4514906.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_4514906
loop_
_publ_author_name
'Mishra, Nidhi'
'Singh, Anoop S.'
'Agrahari, Anand K.'
'Singh, Sumit K.'
'Singh, Mala'
'Tiwari, Vinod K.'
_publ_section_title
;
 Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions
 Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands.
;
_journal_issue                   5
_journal_name_full               'ACS combinatorial science'
_journal_page_first              389
_journal_page_last               399
_journal_paper_doi               10.1021/acscombsci.9b00004
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C13 H9 F N2'
_chemical_formula_sum            'C13 H9 F N2'
_chemical_formula_weight         212.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90.000(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.608(3)
_cell_length_b                   7.1350(9)
_cell_length_c                   10.0478(11)
_cell_measurement_reflns_used    4234
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.60
_cell_measurement_theta_min      2.75
_cell_volume                     2122.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1131
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30642
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_min         2.752
_diffrn_source                   x-ray
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             880.0
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0540
_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)+(0.0724P)²+0.7109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1508
_reflns_number_total             2648
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            co9b00004_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4514906
_shelx_shelxl_version_number     2018/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
F1 F 0.54974(5) 0.3082(3) -0.18224(17) 0.1066(7) Uani 1 1 d . .
N1 N 0.63486(6) 0.1918(2) -0.09401(15) 0.0472(4) Uani 1 1 d . .
H1 H 0.626676 0.196906 -0.176056 0.057 Uiso 1 1 calc R U
N2 N 0.63824(6) 0.2618(3) 0.12201(14) 0.0484(4) Uani 1 1 d . .
C7 C 0.66667(7) 0.1118(3) 0.09542(18) 0.0461(5) Uani 1 1 d . .
C2 C 0.66498(7) 0.0674(3) -0.03948(18) 0.0456(5) Uani 1 1 d . .
C3 C 0.69076(8) -0.0742(3) -0.0954(2) 0.0610(6) Uani 1 1 d . .
H3 H 0.689145 -0.102785 -0.185584 0.073 Uiso 1 1 calc R U
C8 C 0.59054(7) 0.4664(3) -0.01659(19) 0.0493(5) Uani 1 1 d . .
C6 C 0.69514(8) 0.0109(3) 0.1800(2) 0.0586(6) Uani 1 1 d . .
H6 H 0.696414 0.037195 0.270600 0.070 Uiso 1 1 calc R U
C1 C 0.62038(6) 0.3053(3) 0.00571(18) 0.0441(5) Uani 1 1 d . .
C10 C 0.55655(8) 0.4663(4) -0.1102(2) 0.0673(7) Uani 1 1 d . .
C5 C 0.72102(8) -0.1272(4) 0.1255(2) 0.0651(6) Uani 1 1 d . .
H5 H 0.740577 -0.194523 0.179893 0.078 Uiso 1 1 calc R U
C9 C 0.59590(9) 0.6306(4) 0.0562(3) 0.0680(7) Uani 1 1 d . .
H9 H 0.617828 0.636439 0.122373 0.082 Uiso 1 1 calc R U
C4 C 0.71893(9) -0.1704(4) -0.0102(3) 0.0686(7) Uani 1 1 d . .
H4 H 0.736955 -0.266216 -0.043670 0.082 Uiso 1 1 calc R U
C11 C 0.52915(11) 0.6157(5) -0.1344(3) 0.0948(10) Uani 1 1 d . .
H11 H 0.506363 0.608568 -0.197886 0.114 Uiso 1 1 calc R U
C13 C 0.56901(11) 0.7855(4) 0.0315(3) 0.0849(9) Uani 1 1 d . .
H13 H 0.573439 0.895578 0.079325 0.102 Uiso 1 1 calc R U
C12 C 0.53594(11) 0.7764(5) -0.0631(3) 0.0944(10) Uani 1 1 d . .
H12 H 0.517869 0.880546 -0.079199 0.113 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'
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
C1 N1 C2 107.23(15)
C1 N1 H1 126.4
C2 N1 H1 126.4
C1 N2 C7 104.71(15)
N2 C7 C2 109.94(17)
N2 C7 C6 130.26(18)
C2 C7 C6 119.8(2)
N1 C2 C3 131.89(18)
N1 C2 C7 105.36(17)
C3 C2 C7 122.74(19)
C4 C3 C2 116.4(2)
C4 C3 H3 121.8
C2 C3 H3 121.8
C10 C8 C9 116.3(2)
C10 C8 C1 123.0(2)
C9 C8 C1 120.74(19)
C5 C6 C7 117.8(2)
C5 C6 H6 121.1
C7 C6 H6 121.1
N2 C1 N1 112.75(18)
N2 C1 C8 124.12(18)
N1 C1 C8 123.00(17)
F1 C10 C11 117.9(2)
F1 C10 C8 118.3(2)
C11 C10 C8 123.8(3)
C6 C5 C4 121.7(2)
C6 C5 H5 119.1
C4 C5 H5 119.1
C13 C9 C8 120.8(2)
C13 C9 H9 119.6
C8 C9 H9 119.6
C3 C4 C5 121.5(2)
C3 C4 H4 119.3
C5 C4 H4 119.3
C10 C11 C12 118.4(3)
C10 C11 H11 120.8
C12 C11 H11 120.8
C12 C13 C9 119.9(3)
C12 C13 H13 120.0
C9 C13 H13 120.0
C11 C12 C13 120.7(3)
C11 C12 H12 119.7
C13 C12 H12 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C10 1.355(3)
N1 C1 1.358(2)
N1 C2 1.372(3)
N1 H1 0.8600
N2 C1 1.320(2)
N2 C7 1.387(3)
C7 C2 1.393(3)
C7 C6 1.397(3)
C2 C3 1.385(3)
C3 C4 1.378(3)
C3 H3 0.9300
C8 C10 1.378(3)
C8 C9 1.390(3)
C8 C1 1.467(3)
C6 C5 1.364(3)
C6 H6 0.9300
C10 C11 1.361(4)
C5 C4 1.399(4)
C5 H5 0.9300
C9 C13 1.385(4)
C9 H9 0.9300
C4 H4 0.9300
C11 C12 1.367(5)
C11 H11 0.9300
C13 C12 1.367(4)
C13 H13 0.9300
C12 H12 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
C1 N2 C7 C2 -0.2(2)
C1 N2 C7 C6 178.3(2)
C1 N1 C2 C3 -177.8(2)
C1 N1 C2 C7 1.0(2)
N2 C7 C2 N1 -0.4(2)
C6 C7 C2 N1 -179.16(18)
N2 C7 C2 C3 178.49(19)
C6 C7 C2 C3 -0.2(3)
N1 C2 C3 C4 178.2(2)
C7 C2 C3 C4 -0.4(3)
N2 C7 C6 C5 -177.4(2)
C2 C7 C6 C5 1.0(3)
C7 N2 C1 N1 0.9(2)
C7 N2 C1 C8 -175.12(18)
C2 N1 C1 N2 -1.2(2)
C2 N1 C1 C8 174.86(17)
C10 C8 C1 N2 -148.5(2)
C9 C8 C1 N2 32.5(3)
C10 C8 C1 N1 35.9(3)
C9 C8 C1 N1 -143.1(2)
C9 C8 C10 F1 -179.1(2)
C1 C8 C10 F1 1.8(4)
C9 C8 C10 C11 0.5(4)
C1 C8 C10 C11 -178.5(2)
C7 C6 C5 C4 -1.1(4)
C10 C8 C9 C13 -1.8(4)
C1 C8 C9 C13 177.3(2)
C2 C3 C4 C5 0.3(4)
C6 C5 C4 C3 0.4(4)
F1 C10 C11 C12 -179.5(3)
C8 C10 C11 C12 0.9(5)
C8 C9 C13 C12 1.7(4)
C10 C11 C12 C13 -1.0(5)
C9 C13 C12 C11 -0.2(5)
