#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:56:27 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261591 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241597.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_7241597
loop_
_publ_author_name
'Guo, Shengmei'
'Zhang, Yuyang'
'Huang, Jianyan'
'Kong, Lin'
'Yang, Jiaxiang'
_publ_section_title
;
 High dual-state blue emission of a functionalized pyrazoline derivative
 for picric acid detection
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              221
_journal_page_last               226
_journal_paper_doi               10.1039/D0CE01195A
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration ab
_chemical_formula_sum            'C23 H22 F N3'
_chemical_formula_weight         359.44
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc23grx8
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-08-31 deposited with the CCDC.	2020-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8960(12)
_cell_length_b                   8.9130(18)
_cell_length_c                   36.162(7)
_cell_measurement_reflns_used    5328
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.52
_cell_measurement_theta_min      2.25
_cell_volume                     1900.4(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            26548
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.13
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_correction_T_min  0.9838
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(18)
_refine_ls_extinction_coef       0.0059(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0190P)²+1.0336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                2653
_reflns_number_total             3342
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ce01195a2.cif
_cod_data_source_block           333
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7241597.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               7241597
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.0231(5) 0.2570(3) 0.09173(8) 0.0486(7) Uani 1 1 d . . .
C9 C 0.0311(6) 0.1123(3) 0.18052(8) 0.0530(8) Uani 1 1 d . . .
C22 C -0.3702(6) -0.2346(4) 0.04659(8) 0.0584(9) Uani 1 1 d . . .
C8 C 0.1377(5) 0.1105(3) 0.21676(8) 0.0545(8) Uani 1 1 d . . .
C18 C -0.1210(5) -0.1380(3) 0.09174(9) 0.0575(8) Uani 1 1 d . . .
H18 H 0.0188 -0.1394 0.1037 0.069 Uiso 1 1 calc R . .
C20 C -0.4925(5) -0.0369(4) 0.08479(8) 0.0558(8) Uani 1 1 d . . .
H20 H -0.6048 0.0303 0.0920 0.067 Uiso 1 1 calc R . .
C6 C 0.3221(6) 0.2018(4) 0.22544(8) 0.0616(9) Uani 1 1 d . . .
H6 H 0.3819 0.2641 0.2073 0.074 Uiso 1 1 calc R . .
C16 C -0.0715(7) 0.3487(4) 0.03112(9) 0.0693(10) Uani 1 1 d . . .
H16 H -0.1737 0.3539 0.0116 0.083 Uiso 1 1 calc R . .
C19 C -0.2824(5) -0.0346(3) 0.10222(7) 0.0460(7) Uani 1 1 d . . .
C11 C -0.2294(5) 0.0838(3) 0.13062(8) 0.0540(8) Uani 1 1 d . . .
H11 H -0.3548 0.1558 0.1317 0.065 Uiso 1 1 calc R . .
C13 C 0.2262(5) 0.3372(4) 0.08919(9) 0.0613(8) Uani 1 1 d . . .
H13 H 0.3280 0.3359 0.1088 0.074 Uiso 1 1 calc R . .
C7 C 0.0552(6) 0.0190(4) 0.24491(9) 0.0649(9) Uani 1 1 d . . .
H7 H -0.0669 -0.0442 0.2401 0.078 Uiso 1 1 calc R . .
C21 C -0.5352(6) -0.1386(4) 0.05675(9) 0.0619(9) Uani 1 1 d . . .
H21 H -0.6757 -0.1407 0.0451 0.074 Uiso 1 1 calc R . .
C15 C 0.1308(7) 0.4238(4) 0.02867(9) 0.0660(9) Uani 1 1 d . . .
H15 H 0.1682 0.4777 0.0075 0.079 Uiso 1 1 calc R . .
C3 C 0.3329(6) 0.1128(4) 0.28852(9) 0.0642(9) Uani 1 1 d . . .
C23 C -0.1637(6) -0.2395(4) 0.06386(9) 0.0664(9) Uani 1 1 d . . .
H23 H -0.0548 -0.3095 0.0569 0.080 Uiso 1 1 calc R . .
C10 C -0.1796(6) 0.0258(4) 0.16988(8) 0.0616(9) Uani 1 1 d . . .
H10A H -0.3042 0.0475 0.1866 0.074 Uiso 1 1 calc R . .
H10B H -0.1514 -0.0814 0.1698 0.074 Uiso 1 1 calc R . .
C17 C -0.1269(6) 0.2650(4) 0.06226(8) 0.0616(9) Uani 1 1 d . . .
H17 H -0.2646 0.2143 0.0633 0.074 Uiso 1 1 calc R . .
C4 C 0.1506(7) 0.0200(4) 0.27987(9) 0.0724(10) Uani 1 1 d . . .
H4 H 0.0917 -0.0429 0.2980 0.087 Uiso 1 1 calc R . .
C5 C 0.4182(6) 0.2024(4) 0.26000(9) 0.0656(10) Uani 1 1 d . . .
H5 H 0.5427 0.2637 0.2645 0.079 Uiso 1 1 calc R . .
C14 C 0.2764(6) 0.4175(4) 0.05805(10) 0.0694(10) Uani 1 1 d . . .
H14 H 0.4132 0.4692 0.0568 0.083 Uiso 1 1 calc R . .
C1 C 0.3229(8) 0.0296(5) 0.35272(9) 0.1009(16) Uani 1 1 d . . .
H1A H 0.1632 0.0500 0.3539 0.151 Uiso 1 1 calc R . .
H1B H 0.3924 0.0551 0.3759 0.151 Uiso 1 1 calc R . .
H1C H 0.3463 -0.0750 0.3477 0.151 Uiso 1 1 calc R . .
C2 C 0.6291(7) 0.1970(6) 0.33117(11) 0.1033(15) Uani 1 1 d . . .
H2A H 0.7464 0.1616 0.3150 0.155 Uiso 1 1 calc R . .
H2B H 0.6734 0.1805 0.3564 0.155 Uiso 1 1 calc R . .
H2C H 0.6056 0.3024 0.3272 0.155 Uiso 1 1 calc R . .
N2 N 0.1166(4) 0.1868(3) 0.15349(7) 0.0570(7) Uani 1 1 d . . .
N3 N -0.0155(4) 0.1650(3) 0.12229(7) 0.0608(7) Uani 1 1 d . . .
N1 N 0.4229(6) 0.1174(4) 0.32373(8) 0.0894(11) Uani 1 1 d . . .
F1 F -0.4091(4) -0.3309(2) 0.01795(5) 0.0828(7) 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'
N N 0.0061 0.0033 '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
C17 C12 C13 118.0(3) . . ?
C17 C12 N3 122.3(3) . . ?
C13 C12 N3 119.5(3) . . ?
N2 C9 C8 121.5(3) . . ?
N2 C9 C10 113.1(3) . . ?
C8 C9 C10 125.4(3) . . ?
C21 C22 F1 119.0(3) . . ?
C21 C22 C23 122.5(3) . . ?
F1 C22 C23 118.4(3) . . ?
C7 C8 C6 116.8(3) . . ?
C7 C8 C9 120.9(3) . . ?
C6 C8 C9 122.3(3) . . ?
C23 C18 C19 121.0(3) . . ?
C21 C20 C19 120.3(3) . . ?
C5 C6 C8 122.0(3) . . ?
C15 C16 C17 121.3(3) . . ?
C18 C19 C20 118.7(3) . . ?
C18 C19 C11 120.9(3) . . ?
C20 C19 C11 120.3(3) . . ?
N3 C11 C19 112.3(2) . . ?
N3 C11 C10 100.9(2) . . ?
C19 C11 C10 115.7(3) . . ?
C14 C13 C12 120.5(3) . . ?
C4 C7 C8 121.5(3) . . ?
C22 C21 C20 119.0(3) . . ?
C14 C15 C16 118.4(3) . . ?
N1 C3 C4 121.5(3) . . ?
N1 C3 C5 121.7(3) . . ?
C4 C3 C5 116.8(3) . . ?
C22 C23 C18 118.4(3) . . ?
C9 C10 C11 102.7(2) . . ?
C12 C17 C16 120.0(3) . . ?
C7 C4 C3 121.5(3) . . ?
C6 C5 C3 121.4(3) . . ?
C13 C14 C15 121.8(3) . . ?
C9 N2 N3 109.1(2) . . ?
N2 N3 C12 118.1(2) . . ?
N2 N3 C11 112.3(2) . . ?
C12 N3 C11 125.9(2) . . ?
C3 N1 C1 120.0(4) . . ?
C3 N1 C2 121.0(4) . . ?
C1 N1 C2 118.8(3) . . ?
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
C12 C17 1.387(4) . ?
C12 C13 1.397(4) . ?
C12 N3 1.395(4) . ?
C9 N2 1.285(4) . ?
C9 C8 1.454(4) . ?
C9 C10 1.512(4) . ?
C22 C21 1.347(4) . ?
C22 F1 1.365(3) . ?
C22 C23 1.369(5) . ?
C8 C7 1.392(4) . ?
C8 C6 1.394(4) . ?
C18 C23 1.377(4) . ?
C18 C19 1.378(4) . ?
C20 C21 1.383(4) . ?
C20 C19 1.390(4) . ?
C6 C5 1.372(4) . ?
C16 C15 1.370(5) . ?
C16 C17 1.390(4) . ?
C19 C11 1.505(4) . ?
C11 N3 1.485(4) . ?
C11 C10 1.539(4) . ?
C13 C14 1.366(4) . ?
C7 C4 1.384(4) . ?
C15 C14 1.367(5) . ?
C3 N1 1.380(4) . ?
C3 C4 1.392(5) . ?
C3 C5 1.398(5) . ?
C1 N1 1.435(5) . ?
C2 N1 1.433(5) . ?
N2 N3 1.385(3) . ?
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
N2 C9 C8 C7 -174.2(3) . . . . ?
C10 C9 C8 C7 3.2(5) . . . . ?
N2 C9 C8 C6 7.4(5) . . . . ?
C10 C9 C8 C6 -175.1(3) . . . . ?
C7 C8 C6 C5 -0.2(5) . . . . ?
C9 C8 C6 C5 178.2(3) . . . . ?
C23 C18 C19 C20 1.7(4) . . . . ?
C23 C18 C19 C11 -175.2(3) . . . . ?
C21 C20 C19 C18 -1.8(4) . . . . ?
C21 C20 C19 C11 175.2(3) . . . . ?
C18 C19 C11 N3 50.0(4) . . . . ?
C20 C19 C11 N3 -127.0(3) . . . . ?
C18 C19 C11 C10 -65.1(4) . . . . ?
C20 C19 C11 C10 117.9(3) . . . . ?
C17 C12 C13 C14 -1.7(5) . . . . ?
N3 C12 C13 C14 174.2(3) . . . . ?
C6 C8 C7 C4 0.6(5) . . . . ?
C9 C8 C7 C4 -177.8(3) . . . . ?
F1 C22 C21 C20 -177.4(3) . . . . ?
C23 C22 C21 C20 2.5(5) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C17 C16 C15 C14 -1.5(5) . . . . ?
C21 C22 C23 C18 -2.6(5) . . . . ?
F1 C22 C23 C18 177.3(3) . . . . ?
C19 C18 C23 C22 0.4(5) . . . . ?
N2 C9 C10 C11 -8.7(4) . . . . ?
C8 C9 C10 C11 173.6(3) . . . . ?
N3 C11 C10 C9 12.2(3) . . . . ?
C19 C11 C10 C9 133.6(3) . . . . ?
C13 C12 C17 C16 1.1(5) . . . . ?
N3 C12 C17 C16 -174.6(3) . . . . ?
C15 C16 C17 C12 0.4(5) . . . . ?
C8 C7 C4 C3 0.2(5) . . . . ?
N1 C3 C4 C7 177.7(4) . . . . ?
C5 C3 C4 C7 -1.4(5) . . . . ?
C8 C6 C5 C3 -1.1(5) . . . . ?
N1 C3 C5 C6 -177.3(3) . . . . ?
C4 C3 C5 C6 1.9(5) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C16 C15 C14 C13 0.9(5) . . . . ?
C8 C9 N2 N3 178.3(3) . . . . ?
C10 C9 N2 N3 0.5(4) . . . . ?
C9 N2 N3 C12 168.4(3) . . . . ?
C9 N2 N3 C11 8.6(4) . . . . ?
C17 C12 N3 N2 -166.9(3) . . . . ?
C13 C12 N3 N2 17.4(4) . . . . ?
C17 C12 N3 C11 -10.1(5) . . . . ?
C13 C12 N3 C11 174.2(3) . . . . ?
C19 C11 N3 N2 -137.1(3) . . . . ?
C10 C11 N3 N2 -13.3(3) . . . . ?
C19 C11 N3 C12 65.0(4) . . . . ?
C10 C11 N3 C12 -171.2(3) . . . . ?
C4 C3 N1 C1 -2.4(5) . . . . ?
C5 C3 N1 C1 176.7(4) . . . . ?
C4 C3 N1 C2 171.3(4) . . . . ?
C5 C3 N1 C2 -9.6(6) . . . . ?
