#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:03:52 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179611 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/75/4507558.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_4507558
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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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-alpha
  (compiled 2012.02.07 svn.r2199, GUI svn.r4069)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.67(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.223(9)
_cell_length_b                   7.623(10)
_cell_length_c                   12.098(16)
_cell_measurement_reflns_used    719
_cell_measurement_temperature    179
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      3.19
_cell_volume                     641.4(14)
_computing_cell_refinement       'SAINT V7.68A (Bruker, 2001)'
_computing_data_collection       'SMART v5.049 (Bruker, 1999)'
_computing_data_reduction        'SAINT V7.68A (Bruker, 2001)'
_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      179
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.710
_diffrn_measured_fraction_theta_max 0.710
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1033
_diffrn_reflns_theta_full        24.35
_diffrn_reflns_theta_max         24.35
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.5029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.1078 before and 0.0349 after correction.
The Ratio of minimum to maximum transmission is 0.6691.
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    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             232
_exptl_crystal_recrystallization_method
'Cryo-crystallised in a Lindemann tube.'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0489
_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)+(0.0960P)²+0.0998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1520
_reflns_number_gt                631
_reflns_number_total             747
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301773h_si_005.cif
_cod_data_source_block           final
_cod_original_cell_volume        641.4(15)
_cod_database_code               4507558
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.057) H2(0.065) H3(0.07) H4(0.063) H6(0.103) H5(0.103)
 H7(0.103)
 Fixed X: H1(0.2578) H2(-0.2244) H3(-0.2326) H4(0) H6(0.3816) H5(0.2515)
 H7(0.3961)
 Fixed Y: H1(0.0071) H2(0.2725) H3(0.3926) H4(0.3189) H6(0.2141) H5(0.0633)
 H7(0.0247)
 Fixed Z: H1(0.2504) H2(0.2535) H3(0.0749) H4(-0.0154) H6(0.0414) H5(-0.0262)
 H7(0.0935)
;
#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+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
C2 C 0.1606(3) 0.0843(3) 0.21410(19) 0.0478(7) Uani 1 1 d .
H1 H 0.2578 0.0071 0.2504 0.057 Uiso 1 1 calc R
F1 F 0.0237(2) 0.0572(2) 0.37014(11) 0.0792(7) Uani 1 1 d .
C1 C 0.1572(3) 0.1557(3) 0.10712(19) 0.0455(7) Uani 1 1 d .
C4 C -0.1311(3) 0.2444(3) 0.21639(19) 0.0545(7) Uani 1 1 d .
H2 H -0.2244 0.2725 0.2535 0.065 Uiso 1 1 calc R
C3 C 0.0183(4) 0.1297(3) 0.26497(18) 0.0506(7) Uani 1 1 d .
C5 C -0.1351(4) 0.3151(3) 0.1102(2) 0.0580(8) Uani 1 1 d .
H3 H -0.2326 0.3926 0.0749 0.070 Uiso 1 1 calc R
C6 C 0.0059(3) 0.2710(3) 0.05619(18) 0.0523(7) Uani 1 1 d .
H4 H 0.0000 0.3189 -0.0154 0.063 Uiso 1 1 calc R
C7 C 0.3105(4) 0.1104(3) 0.0487(2) 0.0686(9) Uani 1 1 d .
H6 H 0.3816 0.2141 0.0414 0.103 Uiso 1 1 calc R
H5 H 0.2515 0.0633 -0.0262 0.103 Uiso 1 1 calc R
H7 H 0.3961 0.0247 0.0935 0.103 Uiso 1 1 calc R
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
C2 0.0407(14) 0.0457(13) 0.0511(14) 0.0018(9) 0.0020(11) -0.0006(10)
F1 0.0846(13) 0.1051(13) 0.0465(9) 0.0154(7) 0.0151(8) -0.0135(9)
C1 0.0432(13) 0.0423(12) 0.0491(13) -0.0056(9) 0.0089(10) -0.0064(9)
C4 0.0375(14) 0.0692(15) 0.0560(15) -0.0156(11) 0.0112(12) -0.0034(11)
C3 0.0509(15) 0.0587(14) 0.0372(12) -0.0017(9) 0.0034(11) -0.0130(11)
C5 0.0481(15) 0.0581(15) 0.0582(15) 0.0003(10) -0.0018(13) 0.0101(11)
C6 0.0574(16) 0.0523(13) 0.0416(12) 0.0018(9) 0.0039(11) -0.0032(11)
C7 0.067(2) 0.0702(17) 0.0750(18) -0.0129(13) 0.0299(15) -0.0082(13)
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
C3 C2 C1 119.1(2)
C2 C1 C6 117.8(2)
C2 C1 C7 120.9(2)
C6 C1 C7 121.3(2)
C5 C4 C3 117.1(2)
C2 C3 F1 118.2(2)
C2 C3 C4 123.9(2)
F1 C3 C4 117.9(2)
C4 C5 C6 120.5(2)
C5 C6 C1 121.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 C1 1.398(4)
C2 C3 1.377(4)
F1 C3 1.378(3)
C1 C6 1.408(3)
C1 C7 1.507(4)
C4 C3 1.390(4)
C4 C5 1.386(4)
C5 C6 1.391(4)
