#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/71/1507185.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_1507185
loop_
_publ_author_name
'Koch, Michael'
'Blacque, Olivier'
'Venkatesan, Koushik'
_publ_section_title
;
 Syntheses and tunable emission properties of 2-alkynyl azulenes.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1580
_journal_page_last               1583
_journal_paper_doi               10.1021/ol300327b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C18 H7 F5'
_chemical_formula_sum            'C18 H7 F5'
_chemical_formula_weight         318.24
_chemical_name_systematic        ' 2-[(pentafluorophenyl)ethynyl]azulene'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 104.535(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0895(3)
_cell_length_b                   30.5179(9)
_cell_length_c                   6.8117(2)
_cell_measurement_reflns_used    5465
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      32.56
_cell_measurement_theta_min      2.66
_cell_volume                     1426.59(9)
_computing_cell_refinement
;
CrysAlisPro, version 1.171.33.55 (Agilent, 2011)
;
_computing_data_collection
;
CrysAlisPro, version 1.171.33.55 (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlisPro, version 1.171.33.55 (Agilent, 2011)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
; 
WinGX (Farrugia, 1999), PLATON for Windows (Spek, 2003) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement  ' SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    ' SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 10.4498
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12383
_diffrn_reflns_theta_full        29.56
_diffrn_reflns_theta_max         29.56
_diffrn_reflns_theta_min         2.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Version 1.171.33.55 (Agilent, 2011)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by Clark & Reid (1995).
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0385
_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)+(0.0663P)²+0.0524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1199
_reflns_number_gt                1512
_reflns_number_total             2007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300327b_si_002.cif
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1507185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.5000 0.17917(4) 0.2500 0.0328(3) Uani 1 2 d S
C2 C 0.32730(16) 0.15667(3) 0.19007(15) 0.0338(3) Uani 1 1 d .
C3 C 0.32830(16) 0.11148(4) 0.19004(16) 0.0334(3) Uani 1 1 d .
C4 C 0.5000 0.08757(5) 0.2500 0.0311(3) Uani 1 2 d S
C5 C 0.5000 0.04080(5) 0.2500 0.0369(4) Uani 1 2 d S
C6 C 0.5000 0.00179(5) 0.2500 0.0385(4) Uani 1 2 d S
C7 C 0.5000 -0.04483(5) 0.2500 0.0332(3) Uani 1 2 d S
C8 C 0.33354(16) -0.07151(4) 0.19442(15) 0.0343(3) Uani 1 1 d .
H8 H 0.2057 -0.0616 0.1517 0.041 Uiso 1 1 calc R
C9 C 0.39200(18) -0.11516(3) 0.21392(15) 0.0305(2) Uani 1 1 d .
C10 C 0.2692(2) -0.15143(4) 0.17253(17) 0.0414(3) Uani 1 1 d .
H10 H 0.1368 -0.1453 0.1284 0.050 Uiso 1 1 calc R
C11 C 0.3183(2) -0.19570(4) 0.18850(18) 0.0508(4) Uani 1 1 d .
H11 H 0.2141 -0.2151 0.1527 0.061 Uiso 1 1 calc R
C12 C 0.5000 -0.21486(5) 0.2500 0.0574(6) Uani 1 2 d S
H12 H 0.5000 -0.2453 0.2500 0.069 Uiso 1 2 calc SR
F1 F 0.5000 0.22298(3) 0.2500 0.0474(3) Uani 1 2 d S
F2 F 0.15950(10) 0.17889(2) 0.13277(11) 0.0521(2) Uani 1 1 d .
F3 F 0.15768(10) 0.09055(2) 0.13063(11) 0.0518(2) Uani 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'
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
F1 C1 C2 120.00(7) . .
C2 C1 C2 120.00(13) . 2_655
F2 C2 C1 119.59(10) . .
F2 C2 C3 120.69(10) . .
C1 C2 C3 119.72(10) . .
F3 C3 C2 118.25(10) . .
F3 C3 C4 119.80(10) . .
C2 C3 C4 121.95(10) . .
C3 C4 C3 116.65(13) 2_655 .
C3 C4 C5 121.67(7) 2_655 .
C3 C4 C5 121.67(7) . .
C6 C5 C4 180.0 . .
C5 C6 C7 180.0 . .
C8 C7 C8 109.18(14) . 2_655
C8 C7 C6 125.41(7) . .
C9 C8 C7 108.61(10) . .
C9 C8 H8 125.7 . .
C7 C8 H8 125.7 . .
C8 C9 C10 125.83(12) . .
C8 C9 C9 106.80(7) . 2_655
C10 C9 C9 127.37(8) . 2_655
C9 C10 C11 128.59(14) . .
C9 C10 H10 115.7 . .
C11 C10 H10 115.7 . .
C12 C11 C10 129.10(13) . .
C12 C11 H11 115.5 . .
C10 C11 H11 115.5 . .
C11 C12 C11 129.89(16) 2_655 .
C11 C12 H12 115.1 2_655 .
C11 C12 H12 115.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1 1.3369(15) .
C1 C2 1.3735(13) .
C2 F2 1.3394(13) .
C2 C3 1.3792(16) .
C3 F3 1.3376(13) .
C3 C4 1.3898(14) .
C4 C5 1.427(2) .
C5 C6 1.191(2) .
C6 C7 1.423(2) .
C7 C8 1.4053(14) .
C8 C9 1.3915(14) .
C8 H8 0.9300 .
C9 C10 1.3926(17) .
C9 C9 1.486(2) 2_655
C10 C11 1.3928(18) .
C10 H10 0.9300 .
C11 C12 1.3802(17) .
C11 H11 0.9300 .
C12 H12 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101570259
