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#$Date: 2025-08-18 23:06:14 +0200 (Mon, 18 Aug 2025) $
#$Revision: 301780 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/1/55/32/1553240.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_1553240
loop_
_publ_author_name
'Poh, Jian-Siang'
'Browne, Duncan L.'
'Ley, Steven V.'
_publ_section_title
;
 A multistep continuous flow synthesis machine for the preparation of
 pyrazoles via a metal-free amine-redox process.
;
_journal_issue                   1
_journal_name_full               'Reaction chemistry & engineering'
_journal_page_first              101
_journal_page_last               105
_journal_paper_doi               10.1039/c5re00082c
_journal_volume                  1
_journal_year                    2016
_chemical_formula_moiety         'C11 H10 F3 N3'
_chemical_formula_sum            'C11 H10 F3 N3'
_chemical_formula_weight         241.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-10-09 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.016(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2750(8)
_cell_length_b                   7.2650(5)
_cell_length_c                   12.6939(8)
_cell_measurement_reflns_used    3366
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      54.90
_cell_measurement_theta_min      3.77
_cell_volume                     1082.46(12)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.661
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.661
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4319
_diffrn_reflns_point_group_measured_fraction_full 0.661
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         54.992
_diffrn_reflns_theta_min         3.766
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    1.112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1295
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0480
_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)+(0.0586P)²+1.3872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1152
_reflns_number_total             1295
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5re00082c2.cif
_cod_data_source_block           sl1408
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1553240
_cambridge_user_name             'Jian-Siang Poh'
_cambridge_user_crsid            jsp47
_cambridge_supervisor_name       'Steven Ley'
_cambridge_supervisor_crsid      svl1000
_cambridge_crystallographer_name 'John Davies'
_cambridge_crystallographer_crsid jed2
_cambridge_sample_id             JSP-2-141
_cambridge_data_id               sl1408
_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_min   0.697
_shelx_estimated_absorpt_t_max   0.967
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.00537(17) 0.2568(3) 0.34545(16) 0.0257(6) Uani 1 1 d . .
N2 N -0.06881(18) 0.2184(3) 0.40700(17) 0.0289(6) Uani 1 1 d . .
N3 N 0.0074(2) 0.2817(4) 0.15853(19) 0.0356(7) Uani 1 1 d D .
H3A H -0.033(2) 0.287(4) 0.0895(11) 0.046(9) Uiso 1 1 d D .
H3B H 0.060(2) 0.367(3) 0.177(3) 0.048(10) Uiso 1 1 d D .
C1 C 0.4763(3) 0.2819(5) 0.5815(3) 0.0464(9) Uani 1 1 d . .
F1 F 0.49711(16) 0.1557(3) 0.66131(18) 0.0786(8) Uani 1 1 d . .
F2 F 0.54690(15) 0.2407(4) 0.52267(18) 0.0768(8) Uani 1 1 d . .
F3 F 0.51175(15) 0.4428(3) 0.62988(18) 0.0720(7) Uani 1 1 d . .
C2 C 0.3536(2) 0.2864(4) 0.5147(2) 0.0342(7) Uani 1 1 d . .
C3 C 0.2742(2) 0.3708(4) 0.5571(2) 0.0360(8) Uani 1 1 d . .
H3 H 0.2989 0.4330 0.6258 0.043 Uiso 1 1 calc R U
C4 C 0.1594(2) 0.3654(4) 0.5002(2) 0.0302(7) Uani 1 1 d . .
H4 H 0.1054 0.4251 0.5289 0.036 Uiso 1 1 calc R U
C5 C 0.1238(2) 0.2714(4) 0.4004(2) 0.0260(7) Uani 1 1 d . .
C6 C 0.2029(2) 0.1877(4) 0.3575(2) 0.0316(7) Uani 1 1 d . .
H6 H 0.1785 0.1246 0.2891 0.038 Uiso 1 1 calc R U
C7 C 0.3182(2) 0.1963(4) 0.4149(2) 0.0362(8) Uani 1 1 d . .
H7 H 0.3726 0.1400 0.3852 0.043 Uiso 1 1 calc R U
C8 C -0.0502(2) 0.2508(4) 0.2347(2) 0.0271(7) Uani 1 1 d . .
C9 C -0.1607(2) 0.2046(4) 0.2246(2) 0.0295(7) Uani 1 1 d . .
H9 H -0.2205 0.1881 0.1581 0.035 Uiso 1 1 calc R U
C10 C -0.1681(2) 0.1866(4) 0.3324(2) 0.0276(7) Uani 1 1 d . .
C11 C -0.2692(2) 0.1343(5) 0.3689(2) 0.0399(8) Uani 1 1 d . .
H11A H -0.2466 0.1251 0.4494 0.060 Uiso 1 1 calc R U
H11B H -0.2986 0.0153 0.3365 0.060 Uiso 1 1 calc R U
H11C H -0.3285 0.2283 0.3445 0.060 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C8 N1 N2 111.0(2)
C8 N1 C5 129.5(2)
N2 N1 C5 118.91(19)
C10 N2 N1 104.5(2)
C8 N3 H3A 117(2)
C8 N3 H3B 115(2)
H3A N3 H3B 113(3)
F3 C1 F2 106.1(3)
F3 C1 F1 106.8(3)
F2 C1 F1 105.0(3)
F3 C1 C2 112.4(3)
F2 C1 C2 113.5(3)
F1 C1 C2 112.5(2)
C7 C2 C3 119.8(3)
C7 C2 C1 120.3(3)
C3 C2 C1 119.7(3)
C4 C3 C2 120.6(3)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.3(3)
C3 C4 H4 120.4
C5 C4 H4 120.4
C6 C5 C4 120.3(2)
C6 C5 N1 120.6(2)
C4 C5 N1 119.1(2)
C5 C6 C7 119.8(3)
C5 C6 H6 120.1
C7 C6 H6 120.1
C2 C7 C6 120.1(3)
C2 C7 H7 119.9
C6 C7 H7 119.9
C9 C8 N1 106.6(2)
C9 C8 N3 132.5(2)
N1 C8 N3 120.9(2)
C8 C9 C10 106.1(2)
C8 C9 H9 127.0
C10 C9 H9 127.0
N2 C10 C9 111.8(2)
N2 C10 C11 119.7(2)
C9 C10 C11 128.4(2)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.372(3)
N1 N2 1.391(3)
N1 C5 1.421(3)
N2 C10 1.326(3)
N3 C8 1.372(4)
N3 H3A 0.871(10)
N3 H3B 0.875(10)
C1 F3 1.333(4)
C1 F2 1.333(4)
C1 F1 1.334(4)
C1 C2 1.496(4)
C2 C7 1.379(4)
C2 C3 1.386(4)
C3 C4 1.384(4)
C3 H3 0.9500
C4 C5 1.392(4)
C4 H4 0.9500
C5 C6 1.385(4)
C6 C7 1.390(4)
C6 H6 0.9500
C7 H7 0.9500
C8 C9 1.367(4)
C9 C10 1.404(4)
C9 H9 0.9500
C10 C11 1.495(4)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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
N3 H3A N2 0.871(10) 2.228(15) 3.053(3) 158(3) 4_565
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
C8 N1 N2 C10 1.0(3)
C5 N1 N2 C10 -171.0(2)
F3 C1 C2 C7 141.0(3)
F2 C1 C2 C7 20.7(4)
F1 C1 C2 C7 -98.5(4)
F3 C1 C2 C3 -43.5(4)
F2 C1 C2 C3 -163.8(3)
F1 C1 C2 C3 77.0(4)
C7 C2 C3 C4 0.1(4)
C1 C2 C3 C4 -175.4(3)
C2 C3 C4 C5 1.1(4)
C3 C4 C5 C6 -1.4(4)
C3 C4 C5 N1 176.3(2)
C8 N1 C5 C6 -34.9(4)
N2 N1 C5 C6 135.4(3)
C8 N1 C5 C4 147.4(3)
N2 N1 C5 C4 -42.3(3)
C4 C5 C6 C7 0.6(4)
N1 C5 C6 C7 -177.1(2)
C3 C2 C7 C6 -0.9(4)
C1 C2 C7 C6 174.6(3)
C5 C6 C7 C2 0.6(4)
N2 N1 C8 C9 -1.1(3)
C5 N1 C8 C9 169.8(3)
N2 N1 C8 N3 -179.0(2)
C5 N1 C8 N3 -8.1(4)
N1 C8 C9 C10 0.8(3)
N3 C8 C9 C10 178.3(3)
N1 N2 C10 C9 -0.5(3)
N1 N2 C10 C11 178.2(2)
C8 C9 C10 N2 -0.2(3)
C8 C9 C10 C11 -178.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12763783
