#------------------------------------------------------------------------------
#$Date: 2025-03-28 01:14:15 +0200 (Fri, 28 Mar 2025) $
#$Revision: 298625 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/42/1574257.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_1574257
loop_
_publ_author_name
'Ji, Tingting'
'Yang, Xuesong'
'Chen, Quanliang'
'Zhang, Hongyu'
_publ_section_title
;
 Decimeter-Length Elastic Organic Crystals Capable of Mechanical
 Post-Processing and Optical Waveguide Modulating at 77 K
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D4SC07313D
_journal_year                    2025
_chemical_formula_moiety         'C12 H10 F3 N3 O2'
_chemical_formula_sum            'C12 H10 F3 N3 O2'
_chemical_formula_weight         285.23
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-30 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4921(4)
_cell_length_b                   17.9826(6)
_cell_length_c                   5.17080(10)
_cell_measurement_reflns_used    8234
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.541
_cell_measurement_theta_min      2.723
_cell_volume                     1254.56(6)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            17868
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.619
_diffrn_reflns_theta_min         2.722
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   none
_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    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3479
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0455
_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)+(0.0317P)²+0.2770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2483
_reflns_number_total             3479
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc07313d6.cif
_cod_data_source_block           1
_cod_database_code               1574257
_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   0.987
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C9-C11 \\sim C9-C10
 with sigma of 0.02
 C14-C12 \\sim C14-C13
 with sigma of 0.02
 O2-C11 \\sim O1-C10
 with sigma of 0.02
 O2-C12 \\sim O1-C13
 with sigma of 0.02
 C9-O2 \\sim C9-O1
 with sigma of 0.04
 C14-O2 \\sim C14-O1
 with sigma of 0.04
 C11-C12 \\sim C10-C13
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C11) = Uanis(C10) = Uanis(C9)
4. Others
 Sof(H9BC)=Sof(H9BD)=Sof(H14C)=Sof(H14D)=Sof(O1)=Sof(C10)=Sof(H10A)=Sof(H10B)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=1-FVAR(1)
 Sof(H9AA)=Sof(H9AB)=Sof(H14A)=Sof(H14B)=Sof(O2)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9AA,H9AB), C9(H9BC,H9BD), C14(H14A,H14B), C14(H14C,H14D), C11(H11A,H11B),
 C12(H12A,H12B), C10(H10A,H10B), C13(H13A,H13B)
5.b Aromatic/amide H refined with riding coordinates:
 N005(H005)
5.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
F1 F 0.41929(15) 0.75106(11) -0.5074(5) 0.0811(6) Uani 1 1 d . . . . .
F2 F 0.53370(12) 0.68489(11) -0.1480(5) 0.0783(6) Uani 1 1 d . . . . .
F3 F 0.14774(10) 0.60975(10) -0.2269(4) 0.0675(5) Uani 1 1 d . . . . .
O3 O -0.02583(15) 0.46540(11) 0.6545(5) 0.0602(5) Uani 1 1 d . . . . .
H3 H -0.021431 0.494505 0.776085 0.090 Uiso 1 1 calc R U . . .
N1 N 0.1750(2) 0.74490(18) -0.7158(8) 0.0857(9) Uani 1 1 d . . . . .
N2 N 0.5283(2) 0.56632(17) 0.3313(7) 0.0783(8) Uani 1 1 d . . . . .
N005 N 0.25437(16) 0.53868(13) 0.1351(5) 0.0556(6) Uani 1 1 d . . . . .
H005 H 0.190632 0.538847 0.136396 0.067 Uiso 1 1 calc R U . . .
C1 C 0.2198(2) 0.71688(16) -0.5569(6) 0.0581(7) Uani 1 1 d . . . . .
C2 C 0.2803(2) 0.68164(14) -0.3645(6) 0.0469(6) Uani 1 1 d . . . . .
C3 C 0.3804(2) 0.70074(15) -0.3452(7) 0.0534(7) Uani 1 1 d . . . . .
C4 C 0.43780(19) 0.66636(15) -0.1655(7) 0.0521(6) Uani 1 1 d . . . . .
C5 C 0.40032(19) 0.61251(14) 0.0021(6) 0.0448(6) Uani 1 1 d . . . . .
C6 C 0.29960(18) 0.59043(14) -0.0143(6) 0.0435(6) Uani 1 1 d . . . . .
C7 C 0.24342(17) 0.62798(14) -0.2024(6) 0.0463(6) Uani 1 1 d . . . . .
C8 C 0.4692(2) 0.58462(16) 0.1885(6) 0.0535(7) Uani 1 1 d . . . . .
C9 C 0.3035(2) 0.48279(16) 0.2936(7) 0.0617(7) Uani 1 1 d D . . . .
H9AA H 0.362041 0.466252 0.201312 0.074 Uiso 0.498(9) 1 calc R U P A 1
H9AB H 0.325928 0.506906 0.450798 0.074 Uiso 0.498(9) 1 calc R U P A 1
H9BC H 0.304969 0.498567 0.472926 0.074 Uiso 0.502(9) 1 calc R U P A 2
H9BD H 0.371077 0.475491 0.235168 0.074 Uiso 0.502(9) 1 calc R U P A 2
C14 C 0.0257(2) 0.39866(17) 0.7155(7) 0.0639(9) Uani 1 1 d D . . . .
H14A H 0.061385 0.405489 0.876652 0.077 Uiso 0.498(9) 1 calc R U P A 1
H14B H -0.021974 0.358980 0.740901 0.077 Uiso 0.498(9) 1 calc R U P A 1
H14C H -0.007616 0.356987 0.634185 0.077 Uiso 0.502(9) 1 calc R U P A 2
H14D H 0.024091 0.390928 0.901086 0.077 Uiso 0.502(9) 1 calc R U P A 2
O2 O 0.1645(3) 0.4376(3) 0.5000(15) 0.0589(18) Uani 0.498(9) 1 d D . P A 1
C11 C 0.2479(6) 0.4178(5) 0.3669(17) 0.0617(7) Uani 0.498(9) 1 d D . P A 1
H11A H 0.229395 0.390163 0.213187 0.074 Uiso 0.498(9) 1 calc R U P A 1
H11B H 0.288764 0.385895 0.474011 0.074 Uiso 0.498(9) 1 calc R U P A 1
C12 C 0.0934(5) 0.3773(4) 0.5208(16) 0.0523(18) Uani 0.498(9) 1 d D . P A 1
H12A H 0.059349 0.369998 0.357629 0.063 Uiso 0.498(9) 1 calc R U P A 1
H12B H 0.126534 0.331405 0.567818 0.063 Uiso 0.498(9) 1 calc R U P A 1
O1 O 0.1448(3) 0.4113(3) 0.3504(11) 0.0507(15) Uani 0.502(9) 1 d D . P A 2
C10 C 0.2451(6) 0.4112(5) 0.2671(18) 0.0617(7) Uani 0.502(9) 1 d D . P A 2
H10A H 0.246184 0.396810 0.086402 0.074 Uiso 0.502(9) 1 calc R U P A 2
H10B H 0.279890 0.372893 0.362980 0.074 Uiso 0.502(9) 1 calc R U P A 2
C13 C 0.1330(6) 0.4009(5) 0.6253(17) 0.064(2) Uani 0.502(9) 1 d D . P A 2
H13A H 0.166714 0.441021 0.714530 0.076 Uiso 0.502(9) 1 calc R U P A 2
H13B H 0.164977 0.354723 0.674685 0.076 Uiso 0.502(9) 1 calc R U P A 2
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'
N N 0.0061 0.0033 '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
C14 O3 H3 109.5 . . ?
C6 N005 H005 116.9 . . ?
C6 N005 C9 126.2(2) . . ?
C9 N005 H005 116.9 . . ?
N1 C1 C2 177.3(4) . . ?
C3 C2 C1 119.4(3) . . ?
C7 C2 C1 121.9(3) . . ?
C7 C2 C3 118.7(2) . . ?
F1 C3 C2 120.0(3) . . ?
F1 C3 C4 120.8(3) . . ?
C4 C3 C2 119.2(3) . . ?
F2 C4 C3 118.9(3) . . ?
F2 C4 C5 118.8(3) . . ?
C3 C4 C5 122.3(2) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 C8 115.3(2) . . ?
C6 C5 C8 124.4(3) . . ?
N005 C6 C5 126.2(2) . . ?
N005 C6 C7 118.8(2) . . ?
C7 C6 C5 115.1(2) . . ?
F3 C7 C2 117.7(2) . . ?
F3 C7 C6 117.9(2) . . ?
C2 C7 C6 124.4(2) . . ?
N2 C8 C5 175.3(3) . . ?
N005 C9 H9AA 107.8 . . ?
N005 C9 H9AB 107.8 . . ?
N005 C9 H9BC 110.2 . . ?
N005 C9 H9BD 110.2 . . ?
N005 C9 C10 107.4(4) . . ?
H9AA C9 H9AB 107.1 . . ?
H9BC C9 H9BD 108.5 . . ?
C11 C9 N005 118.1(4) . . ?
C11 C9 H9AA 107.8 . . ?
C11 C9 H9AB 107.8 . . ?
C10 C9 H9BC 110.2 . . ?
C10 C9 H9BD 110.2 . . ?
O3 C14 H14A 109.0 . . ?
O3 C14 H14B 109.0 . . ?
O3 C14 H14C 109.2 . . ?
O3 C14 H14D 109.2 . . ?
O3 C14 C13 112.0(4) . . ?
H14A C14 H14B 107.8 . . ?
H14C C14 H14D 107.9 . . ?
C12 C14 O3 112.8(4) . . ?
C12 C14 H14A 109.0 . . ?
C12 C14 H14B 109.0 . . ?
C13 C14 H14C 109.2 . . ?
C13 C14 H14D 109.2 . . ?
C11 O2 C12 112.8(5) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
O2 C11 C9 110.5(6) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C14 C12 O2 106.1(6) . . ?
C14 C12 H12A 110.5 . . ?
C14 C12 H12B 110.5 . . ?
O2 C12 H12A 110.5 . . ?
O2 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C10 O1 C13 113.8(6) . . ?
C9 C10 H10A 107.8 . . ?
C9 C10 H10B 107.8 . . ?
O1 C10 C9 117.9(6) . . ?
O1 C10 H10A 107.8 . . ?
O1 C10 H10B 107.8 . . ?
H10A C10 H10B 107.2 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
O1 C13 C14 114.3(6) . . ?
O1 C13 H13A 108.7 . . ?
O1 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
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
F1 C3 1.341(3) . ?
F2 C4 1.339(3) . ?
F3 C7 1.338(3) . ?
O3 H3 0.8200 . ?
O3 C14 1.423(3) . ?
N1 C1 1.138(4) . ?
N2 C8 1.135(4) . ?
N005 H005 0.8600 . ?
N005 C6 1.355(3) . ?
N005 C9 1.456(3) . ?
C1 C2 1.434(4) . ?
C2 C3 1.397(4) . ?
C2 C7 1.372(4) . ?
C3 C4 1.358(4) . ?
C4 C5 1.394(4) . ?
C5 C6 1.418(4) . ?
C5 C8 1.430(4) . ?
C6 C7 1.406(4) . ?
C9 H9AA 0.9700 . ?
C9 H9AB 0.9700 . ?
C9 H9BC 0.9700 . ?
C9 H9BD 0.9700 . ?
C9 C11 1.439(8) . ?
C9 C10 1.515(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C12 1.412(7) . ?
C14 C13 1.520(8) . ?
O2 C11 1.366(8) . ?
O2 C12 1.451(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O1 C10 1.420(8) . ?
O1 C13 1.443(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
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
F1 C3 C4 F2 1.7(5) . . . . ?
F1 C3 C4 C5 -178.5(3) . . . . ?
F2 C4 C5 C6 -178.7(3) . . . . ?
F2 C4 C5 C8 3.0(4) . . . . ?
O3 C14 C12 O2 60.9(7) . . . . ?
O3 C14 C13 O1 -59.6(9) . . . . ?
N005 C6 C7 F3 -1.0(4) . . . . ?
N005 C6 C7 C2 179.7(3) . . . . ?
N005 C9 C11 O2 -58.2(7) . . . . ?
N005 C9 C10 O1 -61.5(7) . . . . ?
C1 C2 C3 F1 -0.7(4) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
C1 C2 C7 F3 -0.8(4) . . . . ?
C1 C2 C7 C6 178.6(3) . . . . ?
C2 C3 C4 F2 180.0(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C2 C7 F3 -179.0(3) . . . . ?
C3 C2 C7 C6 0.3(4) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C3 C4 C5 C8 -176.9(3) . . . . ?
C4 C5 C6 N005 179.6(3) . . . . ?
C4 C5 C6 C7 -1.6(4) . . . . ?
C5 C6 C7 F3 -179.8(2) . . . . ?
C5 C6 C7 C2 0.8(4) . . . . ?
C6 N005 C9 C11 -158.9(5) . . . . ?
C6 N005 C9 C10 -140.0(4) . . . . ?
C7 C2 C3 F1 177.6(3) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C8 C5 C6 N005 -2.3(4) . . . . ?
C8 C5 C6 C7 176.5(2) . . . . ?
C9 N005 C6 C5 -16.7(5) . . . . ?
C9 N005 C6 C7 164.5(3) . . . . ?
C11 O2 C12 C14 164.9(6) . . . . ?
C12 O2 C11 C9 165.1(8) . . . . ?
C10 O1 C13 C14 -178.4(6) . . . . ?
C13 O1 C10 C9 -82.1(10) . . . . ?
