#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/75/4507557.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_4507557
loop_
_publ_author_name
'Ridout, Joe'
'Probert, Michael R.'
_publ_section_title
;
 High-Pressure and Low-Temperature Polymorphism in
 C--H···F--C Hydrogen Bonded Monofluorotoluenes
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1943
_journal_paper_doi               10.1021/cg301773h
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C7 H7 F'
_chemical_formula_sum            'C7 H7 F'
_chemical_formula_weight         110.13
_chemical_name_systematic        3-fluorotoluene
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-11-19
_audit_creation_method
;
  Olex2 1.2
  (compiled Nov  5 2012 18:22:26, GUI svn.r4372)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.4526(12)
_cell_length_b                   13.538(3)
_cell_length_c                   14.735(4)
_cell_measurement_reflns_used    1996
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      18.45
_cell_measurement_theta_min      3.36
_cell_volume                     1087.7(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.711
_diffrn_measured_fraction_theta_max 0.711
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_collimation    'Multilayer mirrors'
_diffrn_radiation_monochromator  'Bruker Helios multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ag K\a'
_diffrn_radiation_wavelength     0.56087
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6993
_diffrn_reflns_theta_full        18.57
_diffrn_reflns_theta_max         18.57
_diffrn_reflns_theta_min         2.37
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_target            Ag
_diffrn_source_type              'Incoatec IuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.5843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0800 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.7848.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'Crystallised using high-pressure in a diamond anvil cell.'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0433P)²+1.6291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1549
_reflns_number_gt                390
_reflns_number_total             593
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301773h_si_004.cif
_cod_data_source_block           final
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1087.7(4)
_cod_database_code               4507557
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.063) H3(0.076) H6(0.099) H5(0.099) H7(0.099) H2(0.068)
 H4(0.07)
 Fixed X: H1(-0.1622) H3(0.5104) H6(-0.0725) H5(-0.1902) H7(-0.3011)
 H2(0.4407) H4(0.2442)
 Fixed Y: H1(0.8049) H3(0.8725) H6(1.0371) H5(1.0387) H7(0.9708) H2(0.7133)
 H4(0.997)
 Fixed Z: H1(0.3036) H3(0.4805) H6(0.2919) H5(0.3889) H7(0.3132) H2(0.4321)
 H4(0.4431)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.0925(6) 0.65388(19) 0.3342(3) 0.0904(13) Uani 1 1 d .
C1 C 0.0150(7) 0.9153(3) 0.3664(4) 0.0465(14) Uani 1 1 d .
C2 C -0.0256(7) 0.8200(3) 0.3388(4) 0.0525(14) Uani 1 1 d .
H1 H -0.1622 0.8049 0.3036 0.063 Uiso 1 1 calc R
C5 C 0.3743(8) 0.8586(3) 0.4447(4) 0.0634(17) Uani 1 1 d .
H3 H 0.5104 0.8725 0.4805 0.076 Uiso 1 1 calc R
C7 C -0.1524(8) 0.9980(4) 0.3375(4) 0.0657(17) Uani 1 1 d .
H6 H -0.0725 1.0371 0.2919 0.099 Uiso 1 1 calc R
H5 H -0.1902 1.0387 0.3889 0.099 Uiso 1 1 calc R
H7 H -0.3011 0.9708 0.3132 0.099 Uiso 1 1 calc R
C4 C 0.3349(8) 0.7643(4) 0.4160(4) 0.0564(16) Uani 1 1 d .
H2 H 0.4407 0.7133 0.4321 0.068 Uiso 1 1 calc R
C6 C 0.2161(8) 0.9334(3) 0.4215(4) 0.0581(17) Uani 1 1 d .
H4 H 0.2442 0.9970 0.4431 0.070 Uiso 1 1 calc R
C3 C 0.1352(8) 0.7475(3) 0.3631(4) 0.0533(15) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.115(3) 0.0597(19) 0.096(4) -0.017(2) -0.0036(19) -0.0094(15)
C1 0.046(3) 0.054(3) 0.040(4) -0.002(3) 0.0017(19) -0.002(2)
C2 0.044(3) 0.068(3) 0.045(4) -0.005(3) -0.006(2) -0.009(2)
C5 0.050(3) 0.061(3) 0.079(5) 0.007(3) -0.019(2) -0.012(2)
C7 0.061(3) 0.074(3) 0.063(5) 0.012(3) 0.000(2) 0.013(2)
C4 0.051(3) 0.055(3) 0.063(5) 0.011(3) 0.002(2) 0.002(2)
C6 0.061(3) 0.051(3) 0.062(5) 0.003(3) -0.013(3) -0.010(2)
C3 0.064(3) 0.040(3) 0.056(5) -0.006(3) 0.010(2) -0.009(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0096 0.0061 '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 C7 121.1(4)
C2 C1 C6 117.9(4)
C6 C1 C7 120.9(4)
C3 C2 C1 119.7(4)
C4 C5 C6 121.0(4)
C3 C4 C5 117.5(4)
C5 C6 C1 120.8(5)
F1 C3 C2 118.6(4)
F1 C3 C4 118.3(4)
C4 C3 C2 123.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C3 1.357(5)
C1 C2 1.371(6)
C1 C7 1.506(6)
C1 C6 1.386(6)
C2 C3 1.365(6)
C5 C4 1.362(7)
C5 C6 1.374(6)
C4 C3 1.359(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9606
