High-Pressure and Low-Temperature Polymorphism in C‒H···F‒C Hydrogen Bonded Monofluorotoluenes
Ridout, Joe; Probert, Michael R.; Crystal Growth & Design 13 (2013) 1943–; doi:10.1021/cg301773h

data_4507559
_publ_section_title
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 High-Pressure and Low-Temperature Polymorphism in
 C--H&#x00B7;&#x00B7;&#x00B7;F--C Hydrogen Bonded Monofluorotoluenes
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_journal_issue                   5
_journal_name_full               'Crystal Growth &amp; 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       '\f 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 \l/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/[\s^2^(Fo^2^)+(0.0500P)^2^+0.2338P] where P=(Fo^2^+2Fc^2^)/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 
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_cod_database_code               4507559
_olex2_refinement_description
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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)
;