#------------------------------------------------------------------------------
#$Date: 2022-07-06 01:08:19 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276575 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/72/1567229.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_1567229
loop_
_publ_author_name
'Divya, Indira S.'
'Saravanan, Kandasamy'
'Haseba, Shodai'
'Sasaki, Toshiyuki'
'Koshima, Hideko'
'Wozniak, Krzysztof'
'Varughese, Sunil'
_publ_section_title
;
 Flexible organic crystals. Understanding the tractable co-existence of
 elastic and plastic bending
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC02969C
_journal_year                    2022
_chemical_formula_moiety         'C14 H8 F2 O2'
_chemical_formula_sum            'C14 H8 F2 O2'
_chemical_formula_weight         246.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-01-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-18 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1423(3)
_cell_length_b                   23.2488(14)
_cell_length_c                   4.0149(2)
_cell_measurement_reflns_used    656
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.65
_cell_measurement_theta_min      1.62
_cell_volume                     573.33(5)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7181
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         3.431
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0411
_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)+(0.0424P)²+0.0376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                987
_reflns_number_total             1315
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02969c6.cif
_cod_data_source_block           kb196_0m
_cod_database_code               1567229
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
;
_shelx_res_file
;
TITL KB196_0m_a.res in P2(1)2(1)2
    kb196_0m.res
    created by SHELXL-2018/3 at 14:58:09 on 18-Jan-2022
CELL 0.71073 6.1423 23.2488 4.0149 90 90 90
ZERR 2 0.0003 0.0014 0.0002 0 0 0
LATT -1
SYMM 0.5+X,0.5-Y,-Z
SYMM 0.5-X,0.5+Y,-Z
SYMM -X,-Y,+Z
SFAC C H F O
UNIT 28 16 4 4

L.S. 40
PLAN  5 0 0
SIZE 0.32 0.18 0.16
TEMP 25(2)
CONF
LIST 6
HTAB
BOND $H
fmap 2
acta
MORE -1
OMIT -3 55
OMIT 0 3 1
OMIT 0 2 0
REM <olex2.extras>
REM <HklSrc "%.\\KB196_0m.hkl">
REM </olex2.extras>

WGHT    0.042400    0.037600
FVAR       1.58286
C1    1    0.543256    0.531075    0.609790    11.00000    0.05358    0.05336 =
         0.05968   -0.00451    0.00000   -0.00659
C2    1    0.411721    0.577715    0.469742    11.00000    0.05478    0.04862 =
         0.04963   -0.00615    0.00634   -0.00427
C3    1    0.486839    0.634052    0.500056    11.00000    0.07294    0.05477 =
         0.06508   -0.00444   -0.00278   -0.01028
AFIX  43
H3    2    0.619056    0.641279    0.604883    11.00000   -1.20000
AFIX   0
C4    1    0.365611    0.679161    0.374976    11.00000    0.10774    0.04842 =
         0.07595    0.00022    0.00147   -0.00400
AFIX  43
H4    2    0.414493    0.716888    0.393368    11.00000   -1.20000
AFIX   0
C5    1    0.172557    0.666934    0.223963    11.00000    0.08615    0.06418 =
         0.06422    0.00173    0.00230    0.01720
C6    1    0.093417    0.612752    0.184781    11.00000    0.06242    0.07455 =
         0.07078   -0.00596   -0.00518    0.00831
AFIX  43
H6    2   -0.038506    0.606204    0.077616    11.00000   -1.20000
AFIX   0
C7    1    0.215228    0.567860    0.309181    11.00000    0.05857    0.05537 =
         0.06603   -0.00936    0.00095   -0.00581
AFIX  43
H7    2    0.164928    0.530359    0.285133    11.00000   -1.20000
AFIX   0
O1    4    0.715925    0.538843    0.752061    11.00000    0.06820    0.06555 =
         0.10597   -0.00274   -0.02609   -0.00691
F1    3    0.053308    0.711514    0.102322    11.00000    0.14268    0.08323 =
         0.11727    0.01310   -0.01351    0.04383
HKLF 4




REM  KB196_0m_a.res in P2(1)2(1)2
REM wR2 = 0.1053, GooF = S = 1.117, Restrained GooF = 1.117 for all data
REM R1 = 0.0411 for 987 Fo > 4sig(Fo) and 0.0598 for all 1315 data
REM 82 parameters refined using 0 restraints

END

WGHT      0.0424      0.0376

REM Instructions for potential hydrogen bonds
EQIV $2 x-1, y, z-1
HTAB C6 O1_$2

REM Highest difference peak  0.103,  deepest hole -0.145,  1-sigma level  0.034
Q1    1   0.3616  0.5709  0.2584  11.00000  0.05    0.10
Q2    1   0.7006  0.5346  0.5205  11.00000  0.05    0.10
Q3    1   0.5952  0.5366  0.8248  11.00000  0.05    0.10
Q4    1   0.1072  0.7399 -0.1643  11.00000  0.05    0.09
Q5    1   0.1048  0.7185 -0.2222  11.00000  0.05    0.09
;
_shelx_res_checksum              32652
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, 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_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 0.5433(3) 0.53108(9) 0.6098(6) 0.0555(6) Uani 1 1 d . . . . .
C2 C 0.4117(4) 0.57771(8) 0.4697(6) 0.0510(5) Uani 1 1 d . . . . .
C3 C 0.4868(4) 0.63405(9) 0.5001(6) 0.0643(7) Uani 1 1 d . . . . .
H3 H 0.619056 0.641279 0.604883 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3656(5) 0.67916(11) 0.3750(7) 0.0774(8) Uani 1 1 d . . . . .
H4 H 0.414493 0.716888 0.393368 0.093 Uiso 1 1 calc R U . . .
C5 C 0.1726(5) 0.66693(11) 0.2240(7) 0.0715(7) Uani 1 1 d . . . . .
C6 C 0.0934(4) 0.61275(11) 0.1848(7) 0.0693(7) Uani 1 1 d . . . . .
H6 H -0.038506 0.606204 0.077616 0.083 Uiso 1 1 calc R U . . .
C7 C 0.2152(4) 0.56786(10) 0.3092(6) 0.0600(6) Uani 1 1 d . . . . .
H7 H 0.164928 0.530359 0.285133 0.072 Uiso 1 1 calc R U . . .
O1 O 0.7159(3) 0.53884(7) 0.7521(5) 0.0799(7) Uani 1 1 d . . . . .
F1 F 0.0533(4) 0.71151(7) 0.1023(6) 0.1144(8) 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
C1 0.0536(13) 0.0534(12) 0.0597(14) -0.0045(10) 0.0000(12) -0.0066(10)
C2 0.0548(12) 0.0486(11) 0.0496(12) -0.0062(9) 0.0063(10) -0.0043(10)
C3 0.0729(14) 0.0548(13) 0.0651(15) -0.0044(11) -0.0028(14) -0.0103(12)
C4 0.108(2) 0.0484(13) 0.0759(17) 0.0002(13) 0.0015(17) -0.0040(14)
C5 0.0862(18) 0.0642(15) 0.0642(16) 0.0017(12) 0.0023(15) 0.0172(14)
C6 0.0624(14) 0.0746(16) 0.0708(16) -0.0060(13) -0.0052(13) 0.0083(12)
C7 0.0586(13) 0.0554(13) 0.0660(15) -0.0094(12) 0.0010(12) -0.0058(11)
O1 0.0682(11) 0.0656(11) 0.1060(16) -0.0027(10) -0.0261(11) -0.0069(8)
F1 0.1427(16) 0.0832(11) 0.1173(15) 0.0131(10) -0.0135(13) 0.0438(11)
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C1 120.3(2) . 4_665 ?
O1 C1 C1 116.1(2) . 4_665 ?
O1 C1 C2 123.41(19) . . ?
C3 C2 C1 118.7(2) . . ?
C7 C2 C1 122.42(18) . . ?
C7 C2 C3 118.9(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 123.8(2) . . ?
C6 C5 F1 118.2(3) . . ?
F1 C5 C4 118.0(3) . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C7 117.8(2) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.539(4) 4_665 ?
C1 C2 1.464(3) . ?
C1 O1 1.218(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.387(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(4) . ?
C5 C6 1.359(4) . ?
C5 F1 1.360(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C7 H7 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 C3 174.49(16) 4_665 . . . ?
C1 C1 C2 C7 -5.3(3) 4_665 . . . ?
C1 C2 C3 C4 -179.1(2) . . . . ?
C1 C2 C7 C6 178.9(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C2 C7 C6 -0.9(3) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C3 C4 C5 F1 179.7(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C2 0.2(4) . . . . ?
C7 C2 C3 C4 0.7(3) . . . . ?
O1 C1 C2 C3 -0.1(3) . . . . ?
O1 C1 C2 C7 -179.9(2) . . . . ?
F1 C5 C6 C7 -179.9(2) . . . . ?
