#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/49/4034975.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_4034975
loop_
_publ_author_name
'Zhao, Yilong'
'Zhou, Yuhan'
'Zhang, Chunxia'
'Li, Dong'
'Sun, Puhua'
'Li, Jianzhe'
'Wang, Huan'
'Liu, Jianhui'
'Qu, Jingping'
_publ_section_title
;
 Base-Controlled Regiodivergent Azidation of Trifluoromethyl Alkenyl
 Triflates: Transition-Metal-Free Access to CF₃-Containing
 Allyl Azides and Alkenyl Azides.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2858
_journal_page_last               2868
_journal_paper_doi               10.1021/acs.joc.7b03294
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C13 H14 F3 N3 O3'
_chemical_formula_weight         317.27
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   22.0462(10)
_cell_length_b                   22.0462(10)
_cell_length_c                   12.8478(12)
_cell_measurement_reflns_used    0.8
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      0.2
_cell_measurement_theta_min      0.3
_cell_volume                     6244.5(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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            46568
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0714
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0660P)²+7.4477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1775
_reflns_number_gt                1886
_reflns_number_total             2744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03294_si_002.cif
_cod_data_source_block           2q
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Tetragonal' was changed to
'tetragonal' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'I4(1)/a  '
_cod_database_code               4034975
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
O2 O 0.12050(10) 0.56425(9) 0.05962(15) 0.0716(6) Uani 1 1 d .
O3 O 0.15260(11) 0.51389(11) -0.11935(17) 0.0859(7) Uani 1 1 d .
C6 C 0.01251(12) 0.59102(13) -0.2007(2) 0.0596(7) Uani 1 1 d .
O1 O 0.02000(11) 0.62870(12) 0.07798(17) 0.0916(8) Uani 1 1 d .
C8 C 0.10031(13) 0.54693(13) -0.1211(2) 0.0608(8) Uani 1 1 d .
C9 C 0.08396(13) 0.57167(13) -0.0255(2) 0.0579(7) Uani 1 1 d .
F3 F -0.08171(12) 0.62476(12) -0.64039(17) 0.1230(9) Uani 1 1 d .
C7 C 0.06483(13) 0.55644(13) -0.2076(2) 0.0625(8) Uani 1 1 d .
H7A H 0.0760 0.5396 -0.2711 0.075 Uiso 1 1 calc R
F2 F -0.01571(12) 0.66973(12) -0.5479(2) 0.1240(9) Uani 1 1 d .
C11 C -0.02146(14) 0.58047(14) -0.3854(2) 0.0659(8) Uani 1 1 d .
H11A H 0.0131 0.5582 -0.4020 0.079 Uiso 1 1 calc R
N3 N -0.09730(14) 0.53367(14) -0.5014(2) 0.0861(9) Uani 1 1 d .
F1 F 0.00216(12) 0.58124(13) -0.60672(18) 0.1274(9) Uani 1 1 d .
C5 C -0.00357(14) 0.61593(14) -0.1059(2) 0.0670(8) Uani 1 1 d .
H5A H -0.0385 0.6393 -0.1009 0.080 Uiso 1 1 calc R
C12 C -0.06739(14) 0.59114(14) -0.4680(2) 0.0669(8) Uani 1 1 d .
H12A H -0.0983 0.6192 -0.4416 0.080 Uiso 1 1 calc R
N2 N -0.12516(17) 0.51024(16) -0.4313(3) 0.0964(10) Uani 1 1 d .
C4 C 0.03191(14) 0.60638(14) -0.0182(2) 0.0642(8) Uani 1 1 d .
C13 C -0.04089(18) 0.61639(18) -0.5653(3) 0.0866(10) Uani 1 1 d .
C10 C -0.02736(13) 0.60088(14) -0.2906(2) 0.0636(8) Uani 1 1 d .
H10A H -0.0613 0.6248 -0.2784 0.076 Uiso 1 1 calc R
C2 C 0.1073(2) 0.5123(2) 0.1194(3) 0.1247(17) Uani 1 1 d .
H2A H 0.1348 0.5100 0.1771 0.187 Uiso 1 1 calc R
H2B H 0.1117 0.4768 0.0769 0.187 Uiso 1 1 calc R
H2C H 0.0664 0.5148 0.1448 0.187 Uiso 1 1 calc R
N1 N -0.1520(2) 0.4845(2) -0.3726(4) 0.1512(19) Uani 1 1 d .
C3 C 0.1750(2) 0.4913(2) -0.2139(3) 0.1217(17) Uani 1 1 d .
H3B H 0.2115 0.4687 -0.2013 0.183 Uiso 1 1 calc R
H3C H 0.1836 0.5245 -0.2600 0.183 Uiso 1 1 calc R
H3D H 0.1453 0.4652 -0.2451 0.183 Uiso 1 1 calc R
C1 C -0.0348(2) 0.6598(3) 0.0937(4) 0.152(2) Uani 1 1 d .
H1A H -0.0374 0.6726 0.1650 0.228 Uiso 1 1 calc R
H1B H -0.0682 0.6334 0.0779 0.228 Uiso 1 1 calc R
H1C H -0.0362 0.6947 0.0490 0.228 Uiso 1 1 calc R
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
C9 O2 C2 114.3(3)
C8 O3 C3 118.2(3)
C5 C6 C7 119.2(3)
C5 C6 C10 118.7(3)
C7 C6 C10 122.0(3)
C4 O1 C1 118.4(3)
O3 C8 C7 125.2(3)
O3 C8 C9 114.4(3)
C7 C8 C9 120.4(3)
O2 C9 C4 120.0(3)
O2 C9 C8 120.4(3)
C4 C9 C8 119.5(3)
C8 C7 C6 120.4(3)
C10 C11 C12 123.0(3)
N2 N3 C12 111.9(3)
C6 C5 C4 120.7(3)
C13 C12 N3 104.4(3)
C13 C12 C11 113.1(3)
N3 C12 C11 111.9(3)
N1 N2 N3 173.7(4)
O1 C4 C9 115.1(3)
O1 C4 C5 125.2(3)
C9 C4 C5 119.8(3)
F3 C13 F2 106.5(3)
F3 C13 F1 105.7(3)
F2 C13 F1 106.6(3)
F3 C13 C12 113.3(3)
F2 C13 C12 110.9(3)
F1 C13 C12 113.4(3)
C11 C10 C6 128.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C9 1.368(3)
O2 C2 1.409(4)
O3 C8 1.364(4)
O3 C3 1.403(4)
C6 C5 1.383(4)
C6 C7 1.385(4)
C6 C10 1.467(4)
O1 C4 1.356(3)
O1 C1 1.403(5)
C8 C7 1.375(4)
C8 C9 1.391(4)
C9 C4 1.382(4)
F3 C13 1.333(4)
F2 C13 1.319(4)
C11 C10 1.305(4)
C11 C12 1.485(4)
N3 N2 1.207(5)
N3 C12 1.492(4)
F1 C13 1.336(4)
C5 C4 1.388(4)
C12 C13 1.488(5)
N2 N1 1.114(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328804
