#------------------------------------------------------------------------------
#$Date: 2021-09-06 13:33:18 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268693 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/27/7242771.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_7242771
loop_
_publ_author_name
'Giri, Prasenjit'
'Mazumder, Abhrojyoti'
'Dey, Dibyendu'
'Garani, Souvik'
'Raveendran, Anju'
'Panda, Manas K.'
_publ_section_title
;
 Light-fueled rapid macroscopic motion of a green fluorescent organic
 crystal
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              5876
_journal_page_last               5881
_journal_paper_doi               10.1039/D1CE00460C
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C17 H12 F2 N2 O'
_chemical_formula_weight         298.29
_chemical_name_systematic        E-ArF2
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8711(3)
_cell_length_b                   11.1490(10)
_cell_length_c                   32.557(3)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.94
_cell_measurement_theta_min      2.50
_cell_volume                     1405.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            48393
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.989
_diffrn_reflns_theta_min         1.931
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_process_details   'multi scan'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       Acicular
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.163
_refine_ls_abs_structure_details
;
 Flack x determined using 1125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.24(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0396
_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)+(0.0788P)²+0.2887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2945
_reflns_number_total             3029
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00460c12.cif
_cod_data_source_block           E-ARF2
_cod_depositor_comments          'Adding full bibliography for 7242771.cif.'
_cod_database_code               7242771
_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
F2 F -0.0300(7) 0.27257(19) 0.46568(6) 0.0749(7) Uani 1 1 d . . . . .
F1 F 0.3301(9) 0.6461(2) 0.51358(6) 0.0873(9) Uani 1 1 d . . . . .
O2 O 0.8084(10) 0.6821(2) 0.15187(7) 0.0745(9) Uani 1 1 d . . . . .
N1 N 0.9558(7) 0.49546(19) 0.17322(7) 0.0431(5) Uani 1 1 d . . . . .
H1 H 1.0501 0.4301 0.1648 0.052 Uiso 1 1 calc R U . . .
N2 N 0.6548(12) 0.7693(3) 0.35770(9) 0.0759(11) Uani 1 1 d . . . . .
C1 C 1.0718(13) 0.5517(3) 0.10307(9) 0.0708(11) Uani 1 1 d . . . . .
H1A H 0.8893 0.5554 0.0832 0.106 Uiso 1 1 calc R U . . .
H1B H 1.1648 0.4720 0.1039 0.106 Uiso 1 1 calc R U . . .
H1C H 1.2508 0.6073 0.0956 0.106 Uiso 1 1 calc R U . . .
C2 C 0.9315(9) 0.5841(3) 0.14478(8) 0.0496(7) Uani 1 1 d . . . . .
C3 C 0.8484(6) 0.4956(2) 0.21446(7) 0.0345(5) Uani 1 1 d . . . . .
C4 C 0.6829(7) 0.5924(2) 0.23321(7) 0.0376(5) Uani 1 1 d . . . . .
H4 H 0.6377 0.6618 0.2183 0.045 Uiso 1 1 calc R U . . .
C5 C 0.5866(7) 0.5846(2) 0.27400(8) 0.0369(5) Uani 1 1 d . . . . .
H5 H 0.4768 0.6496 0.2863 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6498(6) 0.4815(2) 0.29734(8) 0.0355(5) Uani 1 1 d . . . . .
C7 C 0.5448(7) 0.4662(2) 0.33992(8) 0.0383(5) Uani 1 1 d . . . . .
H7 H 0.5081 0.3871 0.3479 0.046 Uiso 1 1 calc R U . . .
C8 C 0.4923(7) 0.5485(2) 0.36961(7) 0.0360(5) Uani 1 1 d . . . . .
C9 C 0.3691(6) 0.5190(2) 0.41161(7) 0.0365(5) Uani 1 1 d . . . . .
C10 C 0.2213(7) 0.4070(2) 0.41914(8) 0.0422(6) Uani 1 1 d . . . . .
H10 H 0.1954 0.3513 0.3981 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1144(8) 0.3807(3) 0.45852(8) 0.0473(7) Uani 1 1 d . . . . .
C12 C 0.1454(9) 0.4582(3) 0.49085(8) 0.0521(7) Uani 1 1 d . . . . .
H12 H 0.0731 0.4378 0.5172 0.062 Uiso 1 1 calc R U . . .
C13 C 0.5782(9) 0.6721(3) 0.36228(8) 0.0482(7) Uani 1 1 d . . . . .
C14 C 0.4008(8) 0.6008(3) 0.44353(8) 0.0458(6) Uani 1 1 d . . . . .
H14 H 0.4953 0.6764 0.4390 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2887(10) 0.5673(3) 0.48222(8) 0.0528(7) Uani 1 1 d . . . . .
C16 C 0.8099(7) 0.3847(2) 0.27768(8) 0.0385(5) Uani 1 1 d . . . . .
H16 H 0.8498 0.3144 0.2923 0.046 Uiso 1 1 calc R U . . .
C17 C 0.9095(7) 0.3916(2) 0.23714(8) 0.0394(6) Uani 1 1 d . . . . .
H17 H 1.0181 0.3265 0.2248 0.047 Uiso 1 1 calc R U . . .
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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 129.1(2) . . ?
C2 N1 H1 115.5 . . ?
C3 N1 H1 115.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 N1 123.6(3) . . ?
O2 C2 C1 121.9(3) . . ?
N1 C2 C1 114.5(3) . . ?
C17 C3 C4 119.3(2) . . ?
C17 C3 N1 117.1(2) . . ?
C4 C3 N1 123.7(2) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C16 117.5(2) . . ?
C5 C6 C7 124.4(2) . . ?
C16 C6 C7 118.0(2) . . ?
C8 C7 C6 130.2(2) . . ?
C8 C7 H7 114.9 . . ?
C6 C7 H7 114.9 . . ?
C7 C8 C13 119.9(2) . . ?
C7 C8 C9 123.8(2) . . ?
C13 C8 C9 116.1(2) . . ?
C14 C9 C10 119.5(2) . . ?
C14 C9 C8 121.0(2) . . ?
C10 C9 C8 119.5(2) . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
F2 C11 C12 117.9(2) . . ?
F2 C11 C10 118.3(3) . . ?
C12 C11 C10 123.8(3) . . ?
C15 C12 C11 116.1(2) . . ?
C15 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
N2 C13 C8 177.4(4) . . ?
C15 C14 C9 118.4(3) . . ?
C15 C14 H14 120.8 . . ?
C9 C14 H14 120.8 . . ?
F1 C15 C12 118.0(3) . . ?
F1 C15 C14 118.3(3) . . ?
C12 C15 C14 123.7(3) . . ?
C17 C16 C6 121.3(2) . . ?
C17 C16 H16 119.4 . . ?
C6 C16 H16 119.4 . . ?
C16 C17 C3 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C3 C17 H17 119.8 . . ?
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
F2 C11 1.349(4) . ?
F1 C15 1.356(3) . ?
O2 C2 1.214(4) . ?
N1 C2 1.358(3) . ?
N1 C3 1.405(3) . ?
N1 H1 0.8600 . ?
N2 C13 1.134(4) . ?
C1 C2 1.507(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C17 1.395(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C16 1.399(3) . ?
C6 C7 1.455(3) . ?
C7 C8 1.349(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.437(4) . ?
C8 C9 1.485(3) . ?
C9 C14 1.388(4) . ?
C9 C10 1.395(4) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C12 C15 1.366(5) . ?
C12 H12 0.9300 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
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
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
N1 H1 N2 0.86 2.25 3.105(4) 174.4 3_745
C1 H1B N2 0.96 2.68 3.559(5) 153.2 3_745
C4 H4 O2 0.93 2.27 2.872(3) 121.6 .
C10 H10 O2 0.93 2.49 3.412(3) 170.8 3_645
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
C3 N1 C2 O2 0.8(6) . . . . ?
C3 N1 C2 C1 -179.4(3) . . . . ?
C2 N1 C3 C17 -179.2(3) . . . . ?
C2 N1 C3 C4 1.6(5) . . . . ?
C17 C3 C4 C5 0.9(4) . . . . ?
N1 C3 C4 C5 -179.9(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C16 -1.1(4) . . . . ?
C4 C5 C6 C7 -177.8(3) . . . . ?
C5 C6 C7 C8 -27.2(4) . . . . ?
C16 C6 C7 C8 156.1(3) . . . . ?
C6 C7 C8 C13 -7.0(4) . . . . ?
C6 C7 C8 C9 177.2(3) . . . . ?
C7 C8 C9 C14 163.8(3) . . . . ?
C13 C8 C9 C14 -12.1(4) . . . . ?
C7 C8 C9 C10 -15.8(4) . . . . ?
C13 C8 C9 C10 168.3(3) . . . . ?
C14 C9 C10 C11 -0.8(4) . . . . ?
C8 C9 C10 C11 178.9(3) . . . . ?
C9 C10 C11 F2 179.7(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
F2 C11 C12 C15 -179.2(3) . . . . ?
C10 C11 C12 C15 0.6(5) . . . . ?
C10 C9 C14 C15 1.0(4) . . . . ?
C8 C9 C14 C15 -178.6(3) . . . . ?
C11 C12 C15 F1 -178.8(3) . . . . ?
C11 C12 C15 C14 -0.3(5) . . . . ?
C9 C14 C15 F1 178.0(3) . . . . ?
C9 C14 C15 C12 -0.5(5) . . . . ?
C5 C6 C16 C17 1.6(4) . . . . ?
C7 C6 C16 C17 178.5(2) . . . . ?
C6 C16 C17 C3 -0.8(4) . . . . ?
C4 C3 C17 C16 -0.5(4) . . . . ?
N1 C3 C17 C16 -179.7(2) . . . . ?
