#------------------------------------------------------------------------------
#$Date: 2023-07-04 00:54:26 +0300 (Tue, 04 Jul 2023) $
#$Revision: 284758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/18/7131812.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_7131812
loop_
_publ_author_name
'Sharma, Ruchi'
'Jain, Swati'
'Sihag, Naveen'
'Yadav, M. Ramu'
_publ_section_title
;
 Ligand-free Pd-catalyzed double Heck reaction of
 N-(o-bromoaryl)acrylamides with
 α-F/CF₃-acrylates.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc01740k
_journal_year                    2023
_chemical_formula_moiety         'C8 H8 F2 O4'
_chemical_formula_sum            'C8 H8 F2 O4'
_chemical_formula_weight         206.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-12-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-29 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                102.961(2)
_cell_angle_beta                 109.449(2)
_cell_angle_gamma                96.622(2)
_cell_formula_units_Z            1
_cell_length_a                   5.6570(4)
_cell_length_b                   6.5148(4)
_cell_length_c                   6.5836(5)
_cell_measurement_reflns_used    3817
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      3.28
_cell_volume                     218.14(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      301.00
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.9962
_diffrn_reflns_Laue_measured_fraction_max 0.9967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5448
_diffrn_reflns_point_group_measured_fraction_full 0.9962
_diffrn_reflns_point_group_measured_fraction_max 0.9967
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         3.28
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1562 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9049.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       block
_exptl_crystal_F_000             106.0
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.1849
_refine_diff_density_min         -0.1439
_refine_diff_density_rms         0.0341
_refine_ls_d_res_high            0.7981
_refine_ls_d_res_low             6.2116
_refine_ls_goodness_of_fit_ref   1.1251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     65
_refine_ls_number_reflns         898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1251
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0347P)²+0.0503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              7
_reflns_limit_k_min              -8
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                824
_reflns_number_total             901
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc01740k2.cif
_cod_data_source_block           VS_297SPOT1_0m_a_a
_cod_database_code               7131812
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
F1 F 0.46333(15) 0.63635(12) 0.72375(15) 0.0513(3) Uani 1.000000 .
O1 O 0.68246(17) 0.33845(15) 0.83798(16) 0.0440(3) Uani 1.000000 .
O2 O 0.3181(2) 0.08784(16) 0.6800(2) 0.0584(3) Uani 1.000000 .
C1 C 0.8213(3) 0.1778(2) 0.9099(3) 0.0513(4) Uani 1.000000 .
H1a H 0.9968(6) 0.2452(4) 1.0006(16) 0.0769(6) Uiso 1.000000 GR
H1b H 0.7450(13) 0.1119(13) 0.9960(16) 0.0769(6) Uiso 1.000000 GR
H1c H 0.8142(18) 0.0699(10) 0.7807(3) 0.0769(6) Uiso 1.000000 GR
C2 C 0.4325(2) 0.2682(2) 0.7237(2) 0.0376(3) Uani 1.000000 .
C3 C 0.3064(2) 0.4421(2) 0.6547(2) 0.0363(3) Uani 1.000000 .
C4 C 0.0596(2) 0.4147(2) 0.5334(2) 0.0371(3) Uani 1.000000 .
H4 H -0.0424(2) 0.2779(2) 0.4889(2) 0.0445(4) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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 O1 C1 115.42(10) . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
O2 C2 O1 125.28(12) . . ?
C3 C2 O1 111.80(11) . . ?
C3 C2 O2 122.91(12) . . ?
C2 C3 F1 114.82(11) . . ?
C4 C3 F1 120.84(11) . . ?
C4 C3 C2 124.33(12) . . ?
C4 C4 C3 123.62(15) 2_566 . ?
H4 C4 C3 118.19(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
F1 C3 1.3454(14) . ?
O1 C1 1.4495(16) . ?
O1 C2 1.3278(15) . ?
O2 C2 1.1967(16) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C2 C3 1.4830(18) . ?
C3 C4 1.3249(19) . ?
C4 C4 1.441(2) 2_566 ?
C4 H4 0.9300 . ?
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
F1 C3 C2 O1 -1.60(12) . . . . ?
F1 C3 C2 O2 178.17(12) . . . . ?
F1 C3 C4 C4 -0.04(14) . . . 2_566 ?
O1 C2 C3 C4 177.99(11) . . . . ?
O2 C2 C3 C4 -2.24(17) . . . . ?
C2 C3 C4 C4 -179.62(15) . . . 2_566 ?
C3 C4 C4 C3 180.00(19) . . 2_566 2_566 ?
