#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:28:08 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/97/7249748.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_7249748
loop_
_publ_author_name
'Zheng, Yongpeng'
'Wu, Yaodan'
'Li, Jianxiao'
'Wu, Wanqing'
'Yang, Shaorong'
'Qi, Chaorong'
'Jiang, Huanfeng'
_publ_section_title
;
 Palladium-catalyzed amination oxidation of electron-rich olefins in green
 media
;
_journal_issue                   4
_journal_name_full               'Green Chemistry'
_journal_page_first              1018
_journal_page_last               1022
_journal_paper_doi               10.1039/D4GC05771F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C10 H11 F I N O2'
_chemical_formula_sum            'C10 H11 F I N O2'
_chemical_formula_weight         323.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-10 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                100.883(2)
_cell_angle_beta                 93.120(2)
_cell_angle_gamma                118.456(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5850(5)
_cell_length_b                   7.9584(4)
_cell_length_c                   10.8239(6)
_cell_measurement_reflns_used    5079
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.430
_cell_measurement_theta_min      3.003
_cell_volume                     556.16(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6262
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.452
_diffrn_reflns_theta_min         3.003
_exptl_absorpt_coefficient_mu    2.873
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0700 before and 0.0372 after correction. The Ratio of minimum to maximum transmission is 0.7786. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0180
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0116P)²+0.2823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0401
_refine_ls_wR_factor_ref         0.0410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2135
_reflns_number_total             2248
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc05771f2.cif
_cod_data_source_block           220191062_0m
_cod_depositor_comments          'Adding full bibliography for 7249748.cif.'
_cod_database_code               7249748
_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   0.803
_shelx_estimated_absorpt_t_min   0.611
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C9(H9), C7(H7)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
I1 I 0.92269(2) 0.86074(2) 0.67946(2) 0.02757(6) Uani 1 1 d . . . . .
F1 F 0.3257(2) 0.3965(2) 0.90494(14) 0.0449(4) Uani 1 1 d . . . . .
O2 O 0.2912(2) 0.7894(2) 0.21591(15) 0.0294(4) Uani 1 1 d . . . . .
O1 O 0.6164(2) 0.9211(2) 0.30706(16) 0.0327(4) Uani 1 1 d . . . . .
N1 N 0.5065(3) 0.7788(3) 0.51490(18) 0.0273(4) Uani 1 1 d . . . . .
H1 H 0.633737 0.862888 0.512445 0.033 Uiso 1 1 calc R . . . .
C10 C 0.6161(3) 0.6949(3) 0.6975(2) 0.0244(5) Uani 1 1 d . . . . .
C5 C 0.4609(3) 0.6830(3) 0.6124(2) 0.0227(4) Uani 1 1 d . . . . .
C3 C 0.4383(3) 0.8306(3) 0.3099(2) 0.0249(5) Uani 1 1 d . . . . .
C8 C 0.3715(4) 0.4930(4) 0.8098(2) 0.0308(5) Uani 1 1 d . . . . .
C6 C 0.2624(4) 0.5768(3) 0.6336(2) 0.0280(5) Uani 1 1 d . . . . .
H6 H 0.155243 0.569633 0.579137 0.034 Uiso 1 1 calc R . . . .
C4 C 0.3467(3) 0.7419(3) 0.4171(2) 0.0248(5) Uani 1 1 d . . . . .
H4A H 0.265628 0.800647 0.453242 0.030 Uiso 1 1 calc R . . . .
H4B H 0.254918 0.598139 0.384506 0.030 Uiso 1 1 calc R . . . .
C9 C 0.5716(3) 0.6003(3) 0.7964(2) 0.0285(5) Uani 1 1 d . . . . .
H9 H 0.677176 0.609574 0.853585 0.034 Uiso 1 1 calc R . . . .
C7 C 0.2154(4) 0.4809(4) 0.7316(2) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.078611 0.408722 0.744193 0.036 Uiso 1 1 calc R . . . .
C2 C 0.3581(4) 0.8655(4) 0.1044(2) 0.0326(5) Uani 1 1 d . . . . .
H2A H 0.435934 0.806967 0.062742 0.039 Uiso 1 1 calc R . . . .
H2B H 0.446688 1.010509 0.130001 0.039 Uiso 1 1 calc R . . . .
C1 C 0.1713(4) 0.8108(4) 0.0146(2) 0.0436(7) Uani 1 1 d . . . . .
H1A H 0.210880 0.860183 -0.061554 0.065 Uiso 1 1 calc GR . . . .
H1B H 0.095658 0.869471 0.056907 0.065 Uiso 1 1 calc GR . . . .
H1C H 0.085309 0.667066 -0.010322 0.065 Uiso 1 1 calc GR . . . .
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'
I I -0.4742 1.8119 '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
C3 O2 C2 116.15(18) . . ?
C5 N1 C4 120.39(19) . . ?
C5 C10 I1 120.63(17) . . ?
C9 C10 I1 118.11(16) . . ?
C9 C10 C5 121.2(2) . . ?
N1 C5 C10 120.9(2) . . ?
N1 C5 C6 121.9(2) . . ?
C6 C5 C10 117.2(2) . . ?
O2 C3 C4 110.05(19) . . ?
O1 C3 O2 124.6(2) . . ?
O1 C3 C4 125.3(2) . . ?
F1 C8 C9 119.1(2) . . ?
F1 C8 C7 118.5(2) . . ?
C7 C8 C9 122.4(2) . . ?
C7 C6 C5 122.2(2) . . ?
N1 C4 C3 109.51(18) . . ?
C8 C9 C10 118.6(2) . . ?
C8 C7 C6 118.3(2) . . ?
O2 C2 C1 107.3(2) . . ?
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
I1 C10 2.100(2) . ?
F1 C8 1.362(3) . ?
O2 C3 1.337(3) . ?
O2 C2 1.460(3) . ?
O1 C3 1.196(3) . ?
N1 C5 1.381(3) . ?
N1 C4 1.442(3) . ?
C10 C5 1.409(3) . ?
C10 C9 1.389(3) . ?
C5 C6 1.391(3) . ?
C3 C4 1.502(3) . ?
C8 C9 1.375(3) . ?
C8 C7 1.371(3) . ?
C6 C7 1.386(3) . ?
C2 C1 1.498(4) . ?
