#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:03:52 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179611 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/75/4507559.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_4507559
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_absolute_configuration unk
_chemical_formula_moiety         'C7 H7 F'
_chemical_formula_sum            'C7 H7 F'
_chemical_formula_weight         110.13
_chemical_name_systematic        4-fluorotoluene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-11-19
_audit_creation_method
;
  Olex2 1.2-alpha
  (compiled 2012.02.07 svn.r2199, GUI svn.r4069)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.215(4)
_cell_length_b                   4.7872(8)
_cell_length_c                   8.9622(19)
_cell_measurement_reflns_used    872
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      19.61
_cell_measurement_theta_min      3.02
_cell_volume                     567.0(2)
_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
;
XM, 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 0.701
_diffrn_measured_fraction_theta_max 0.701
_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  0.0503
_diffrn_reflns_av_unetI/netI     0.1061
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3013
_diffrn_reflns_theta_full        18.33
_diffrn_reflns_theta_max         18.33
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_target            Ag
_diffrn_source_type              'Incoatec IuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_correction_T_min  0.5374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.1072 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.7218.
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    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cylinder
_exptl_crystal_F_000             232
_exptl_crystal_recrystallization_method
'Crystallised at high-pressure using a diamond anvil cell.'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_size_rad          0.25
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         540
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.2338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                369
_reflns_number_total             540
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301773h_si_006.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_database_code               4507559
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H4(0.056) H3(0.06) H1(0.079) H2(0.075) H5(0.104) H7(0.104)
 H6(0.104)
 Fixed X: H4(0.4246) H3(0.297) H1(0.4175) H2(0.289) H5(0.5781) H7(0.5451)
 H6(0.5005)
 Fixed Y: H4(0.6655) H3(0.3341) H1(0.6579) H2(0.3378) H5(0.8305) H7(0.9233)
 H6(1.0752)
 Fixed Z: H4(-0.0778) H3(-0.08) H1(0.3636) H2(0.3637) H5(0.0917) H7(0.2523)
 H6(0.112)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y+1/2, z+1/2'
4 'x+1/2, -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
F1 F 0.2066(3) 0.1153(5) 0.1454(8) 0.0734(14) Uani 1 1 d .
C6 C 0.3987(9) 0.5973(19) 0.0115(7) 0.047(3) Uani 1 1 d .
H4 H 0.4246 0.6655 -0.0778 0.056 Uiso 1 1 calc R
C5 C 0.3226(10) 0.403(2) 0.0095(8) 0.050(3) Uani 1 1 d .
H3 H 0.2970 0.3341 -0.0800 0.060 Uiso 1 1 calc R
C2 C 0.3937(11) 0.5926(19) 0.2724(9) 0.066(4) Uani 1 1 d .
H1 H 0.4175 0.6579 0.3636 0.079 Uiso 1 1 calc R
C3 C 0.3165(11) 0.400(2) 0.2740(9) 0.062(3) Uani 1 1 d .
H2 H 0.2890 0.3378 0.3637 0.075 Uiso 1 1 calc R
C1 C 0.4374(5) 0.6935(8) 0.1468(16) 0.0513(19) Uani 1 1 d .
C4 C 0.2837(5) 0.3083(9) 0.1502(13) 0.0522(19) Uani 1 1 d .
C7 C 0.5230(6) 0.8991(8) 0.1511(14) 0.069(2) Uani 1 1 d .
H5 H 0.5781 0.8305 0.0917 0.104 Uiso 1 1 calc R
H7 H 0.5451 0.9233 0.2523 0.104 Uiso 1 1 calc R
H6 H 0.5005 1.0752 0.1120 0.104 Uiso 1 1 calc R
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
C5 C6 C1 120.3(6)
C6 C5 C4 117.7(8)
C1 C2 C3 124.3(9)
C4 C3 C2 118.4(9)
C6 C1 C7 121.1(10)
C2 C1 C6 116.6(6)
C2 C1 C7 122.3(11)
F1 C4 C5 116.7(10)
C3 C4 F1 120.8(10)
C3 C4 C5 122.5(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C4 1.376(7)
C6 C5 1.371(15)
C6 C1 1.394(17)
C5 C4 1.434(14)
C2 C3 1.377(15)
C2 C1 1.355(16)
C3 C4 1.269(16)
C1 C7 1.500(9)
