#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:14:47 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229045 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/05/7230531.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_7230531
loop_
_publ_author_name
'Chakraborty, Shaunak'
'Desiraju, Gautam R.'
_publ_section_title
;
 Exploring the structural landscape with ‘partial’
 fluoro-substitution as a probe
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              2793
_journal_paper_doi               10.1039/C8CE00336J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C9 H6.55 F1.45 O2'
_chemical_formula_sum            'C9 H6.55 F1.45 O2'
_chemical_formula_weight         174.31
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.79(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.7420(13)
_cell_length_b                   6.613(3)
_cell_length_c                   31.174(15)
_cell_measurement_reflns_used    1524
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     771.4(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1472
_diffrn_reflns_av_unetI/netI     0.1075
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            4687
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.149
_exptl_absorpt_coefficient_mu    0.128
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       plate
_exptl_crystal_F_000             358.5
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1183P)²+0.1494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1304
_reflns_number_total             1698
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00336j2.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 7230514--7230540.cif.'
_cod_database_code               7230531
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6522(6) 0.2248(3) 0.03457(7) 0.0227(5) Uani 1 1 d . . . . .
C2 C 0.7711(6) 0.3991(4) 0.06003(7) 0.0236(5) Uani 1 1 d . . . . .
H2 H 0.8857 0.5055 0.0464 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7195(6) 0.4095(3) 0.10228(7) 0.0214(5) Uani 1 1 d . . . . .
H3 H 0.6018 0.3010 0.1148 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8291(6) 0.5736(3) 0.13082(6) 0.0216(5) Uani 1 1 d . . . . .
C5 C 0.7861(6) 0.5542(4) 0.17511(7) 0.0246(5) Uani 1 1 d . . . . .
H5 H 0.6876 0.4355 0.1857 0.029 Uiso 0.546(7) 1 calc R U P A 1
F1 F 0.6448(9) 0.3803(5) 0.18998(9) 0.0323(12) Uani 0.454(7) 1 d . . P A 2
C6 C 0.8847(6) 0.7053(4) 0.20394(7) 0.0294(6) Uani 1 1 d . . . . .
H6 H 0.8560 0.6896 0.2333 0.035 Uiso 1 1 calc R U . . .
C7 C 1.0265(6) 0.8788(4) 0.18698(7) 0.0284(6) Uani 1 1 d . . . . .
C8 C 1.0709(6) 0.9090(4) 0.14360(7) 0.0274(6) Uani 1 1 d . . . . .
H8 H 1.1642 1.0297 0.1333 0.033 Uiso 1 1 calc R U . . .
C9 C 0.9734(6) 0.7558(4) 0.11586(7) 0.0240(5) Uani 1 1 d . . . . .
H9 H 1.0041 0.7736 0.0865 0.029 Uiso 1 1 calc R U . . .
O1 O 0.4854(5) 0.0802(3) 0.05155(5) 0.0295(5) Uani 1 1 d . . . . .
O2 O 0.7293(5) 0.2288(3) -0.00560(5) 0.0323(5) Uani 1 1 d . . . . .
H2A H 0.6366 0.1317 -0.0177 0.048 Uiso 1 1 calc R U . . .
F2 F 1.1262(4) 1.0299(3) 0.21447(5) 0.0437(5) 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'
O O 0.0106 0.0060 '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
O1 C1 O2 122.8(2)
O1 C1 C2 121.14(19)
O2 C1 C2 116.08(18)
C3 C2 C1 121.8(2)
C3 C2 H2 119.1
C1 C2 H2 119.1
C2 C3 C4 126.6(2)
C2 C3 H3 116.7
C4 C3 H3 116.7
C5 C4 C9 117.2(2)
C5 C4 C3 119.9(2)
C9 C4 C3 122.86(18)
F1 C5 C6 119.5(2)
F1 C5 C4 117.9(2)
C6 C5 C4 122.6(2)
C6 C5 H5 118.7
C4 C5 H5 118.7
C7 C6 C5 116.9(2)
C7 C6 H6 121.6
C5 C6 H6 121.6
F2 C7 C6 118.3(2)
F2 C7 C8 118.3(2)
C6 C7 C8 123.4(2)
C7 C8 C9 118.3(2)
C7 C8 H8 120.8
C9 C8 H8 120.8
C8 C9 C4 121.5(2)
C8 C9 H9 119.2
C4 C9 H9 119.2
C1 O2 H2A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.262(3)
C1 O2 1.289(2)
C1 C2 1.466(3)
C2 C3 1.336(3)
C2 H2 0.9300
C3 C4 1.458(3)
C3 H3 0.9300
C4 C5 1.398(3)
C4 C9 1.403(3)
C5 F1 1.350(4)
C5 C6 1.390(3)
C5 H5 0.9300
C6 C7 1.373(4)
C6 H6 0.9300
C7 F2 1.365(3)
C7 C8 1.379(3)
C8 C9 1.378(3)
C8 H8 0.9300
C9 H9 0.9300
O2 H2A 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 0.93 2.61 3.538(3) 172.7 3_765
O2 H2A O1 0.82 1.81 2.615(2) 167.9 3_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 2.3(3)
O2 C1 C2 C3 -177.4(2)
C1 C2 C3 C4 179.3(2)
C2 C3 C4 C5 -174.0(2)
C2 C3 C4 C9 7.1(4)
C9 C4 C5 F1 179.5(2)
C3 C4 C5 F1 0.5(3)
C9 C4 C5 C6 -1.0(3)
C3 C4 C5 C6 -179.9(2)
F1 C5 C6 C7 -179.9(2)
C4 C5 C6 C7 0.5(3)
C5 C6 C7 F2 -180.0(2)
C5 C6 C7 C8 0.6(4)
F2 C7 C8 C9 179.4(2)
C6 C7 C8 C9 -1.1(4)
C7 C8 C9 C4 0.6(3)
C5 C4 C9 C8 0.4(3)
C3 C4 C9 C8 179.3(2)
