#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/71/1507184.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_1507184
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 H11 F'
_chemical_formula_sum            'C18 H11 F'
_chemical_formula_weight         246.27
_chemical_name_systematic        ' 2-[(4-fluorophenyl)ethynyl]azulene'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.138(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.5696(2)
_cell_length_b                   5.8934(2)
_cell_length_c                   14.6636(5)
_cell_measurement_reflns_used    3097
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      32.52
_cell_measurement_theta_min      2.73
_cell_volume                     643.94(4)
_computing_cell_refinement
;
CrysAlisPro, version 1.171.35.11 (Agilent, 2011)
;
_computing_data_collection
;
CrysAlisPro, version 1.171.35.11 (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlisPro, version 1.171.35.11 (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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5828
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Version 1.171.35.11 (Agilent, 2011)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by Clark & Reid (1995).
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.033
_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     172
_refine_ls_number_reflns         1751
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0474P)²+0.0969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                1566
_reflns_number_total             1751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300327b_si_002.cif
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1507184
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.5746(3) -0.1582(4) 0.33748(15) 0.0393(5) Uani 1 1 d .
C2 C 0.4954(3) -0.1071(5) 0.26331(15) 0.0391(5) Uani 1 1 d .
C3 C 0.4061(2) -0.0603(4) 0.17048(14) 0.0339(5) Uani 1 1 d .
C4 C 0.3093(3) 0.1374(4) 0.13898(13) 0.0324(4) Uani 1 1 d .
H4 H 0.2891 0.2608 0.1753 0.039 Uiso 1 1 calc R
C5 C 0.2486(2) 0.1153(4) 0.04311(13) 0.0283(4) Uani 1 1 d .
C6 C 0.1468(2) 0.2726(4) -0.01339(14) 0.0310(4) Uani 1 1 d .
H6 H 0.1167 0.4031 0.0161 0.037 Uiso 1 1 calc R
C7 C 0.0836(3) 0.2621(4) -0.10798(14) 0.0351(5) Uani 1 1 d .
H7 H 0.0167 0.3864 -0.1334 0.042 Uiso 1 1 calc R
C8 C 0.1070(3) 0.0900(4) -0.17011(15) 0.0383(5) Uani 1 1 d .
H8 H 0.0546 0.1174 -0.2314 0.046 Uiso 1 1 calc R
C9 C 0.1966(3) -0.1161(4) -0.15449(15) 0.0380(5) Uani 1 1 d .
H9 H 0.1949 -0.2071 -0.2065 0.046 Uiso 1 1 calc R
C10 C 0.2878(2) -0.2040(4) -0.07211(14) 0.0326(4) Uani 1 1 d .
H10 H 0.3398 -0.3458 -0.0762 0.039 Uiso 1 1 calc R
C11 C 0.3123(2) -0.1094(4) 0.01591(13) 0.0289(4) Uani 1 1 d .
C12 C 0.4073(2) -0.2092(4) 0.09568(14) 0.0337(5) Uani 1 1 d .
H12 H 0.4623 -0.3508 0.0990 0.040 Uiso 1 1 calc R
C13 C 0.6693(3) -0.2259(4) 0.42704(14) 0.0340(5) Uani 1 1 d .
C14 C 0.6708(3) -0.0895(4) 0.50499(15) 0.0399(5) Uani 1 1 d .
H14 H 0.6124 0.0500 0.4988 0.048 Uiso 1 1 calc R
C15 C 0.7580(3) -0.1592(5) 0.59122(16) 0.0463(6) Uani 1 1 d .
H15 H 0.7579 -0.0688 0.6432 0.056 Uiso 1 1 calc R
C16 C 0.8448(3) -0.3645(5) 0.59857(15) 0.0445(6) Uani 1 1 d .
C17 C 0.8481(3) -0.5048(4) 0.52370(15) 0.0416(5) Uani 1 1 d .
H17 H 0.9085 -0.6428 0.5308 0.050 Uiso 1 1 calc R
C18 C 0.7589(3) -0.4347(4) 0.43753(14) 0.0370(5) Uani 1 1 d .
H18 H 0.7585 -0.5274 0.3862 0.044 Uiso 1 1 calc R
F1 F 0.9300(2) -0.4346(4) 0.68235(10) 0.0719(6) 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
C2 C1 C13 178.6(3)
C1 C2 C3 175.4(3)
C12 C3 C4 109.54(18)
C12 C3 C2 123.6(2)
C4 C3 C2 126.9(2)
C5 C4 C3 108.10(18)
C5 C4 H4 125.9
C3 C4 H4 125.9
C6 C5 C4 125.88(19)
C6 C5 C11 127.49(18)
C4 C5 C11 106.62(17)
C5 C6 C7 128.8(2)
C5 C6 H6 115.6
C7 C6 H6 115.6
C6 C7 C8 128.6(2)
C6 C7 H7 115.7
C8 C7 H7 115.7
C9 C8 C7 129.9(2)
C9 C8 H8 115.0
C7 C8 H8 115.0
C10 C9 C8 128.7(2)
C10 C9 H9 115.6
C8 C9 H9 115.6
C9 C10 C11 128.8(2)
C9 C10 H10 115.6
C11 C10 H10 115.6
C10 C11 C12 125.2(2)
C10 C11 C5 127.62(18)
C12 C11 C5 107.16(18)
C11 C12 C3 108.57(19)
C11 C12 H12 125.7
C3 C12 H12 125.7
C14 C13 C18 118.84(19)
C14 C13 C1 121.2(2)
C18 C13 C1 119.9(2)
C15 C14 C13 120.8(2)
C15 C14 H14 119.6
C13 C14 H14 119.6
C16 C15 C14 118.6(2)
C16 C15 H15 120.7
C14 C15 H15 120.7
F1 C16 C15 119.2(2)
F1 C16 C17 118.0(2)
C15 C16 C17 122.8(2)
C16 C17 C18 118.2(2)
C16 C17 H17 120.9
C18 C17 H17 120.9
C17 C18 C13 120.7(2)
C17 C18 H18 119.6
C13 C18 H18 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.185(3)
C1 C13 1.438(3)
C2 C3 1.436(3)
C3 C12 1.406(3)
C3 C4 1.410(3)
C4 C5 1.406(3)
C4 H4 0.9300
C5 C6 1.384(3)
C5 C11 1.487(3)
C6 C7 1.387(3)
C6 H6 0.9300
C7 C8 1.395(3)
C7 H7 0.9300
C8 C9 1.391(3)
C8 H8 0.9300
C9 C10 1.382(3)
C9 H9 0.9300
C10 C11 1.388(3)
C10 H10 0.9300
C11 C12 1.391(3)
C12 H12 0.9300
C13 C14 1.396(3)
C13 C18 1.400(3)
C14 C15 1.382(3)
C14 H14 0.9300
C15 C16 1.372(4)
C15 H15 0.9300
C16 F1 1.348(3)
C16 C17 1.378(3)
C17 C18 1.387(3)
C17 H17 0.9300
C18 H18 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651802
2 PubChem 139039958
