#------------------------------------------------------------------------------
#$Date: 2023-09-01 00:59:48 +0300 (Fri, 01 Sep 2023) $
#$Revision: 285932 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/20/7132078.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_7132078
loop_
_publ_author_name
'Gao, Cheng-Feng'
'Chen, Yue-Ji'
'Nie, Jing'
'Zhang, Fa-Guang'
'Cheung, Chi Wai'
'Ma, Jun-An'
_publ_section_title
;
 Synthesis of di/trifluoromethyl cyclopropane-dicarbonitriles via [2 + 1]
 annulation of fluoro-based diazoethanes with (alkylidene)malononitriles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03897A
_journal_year                    2023
_chemical_formula_moiety         'C18 H12 F2 N2 O2 S'
_chemical_formula_sum            'C18 H12 F2 N2 O2 S'
_chemical_formula_weight         358.36
_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             2021-10-10
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-03-31 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                94.158(2)
_cell_angle_beta                 102.480(2)
_cell_angle_gamma                96.271(2)
_cell_formula_units_Z            2
_cell_length_a                   6.3811(4)
_cell_length_b                   9.4160(6)
_cell_length_c                   14.1943(10)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.49
_cell_measurement_theta_min      2.51
_cell_volume                     823.65(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34354
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.693
_diffrn_reflns_theta_min         2.187
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1629 before and 0.0985 after correction.
The Ratio of minimum to maximum transmission is 0.6282.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0540
_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)+(0.0954P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1578
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3615
_reflns_number_total             4636
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03897a2.cif
_cod_data_source_block           cyj91231
_cod_database_code               7132078
_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   0.953
_shelx_estimated_absorpt_t_min   0.921
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00D), C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
;
_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
S001 S 0.86561(6) 0.41254(4) 0.61086(3) 0.02273(14) Uani 1 1 d . . . . .
F002 F 0.53392(15) 0.26980(11) 0.65647(8) 0.0285(2) Uani 1 1 d . . . . .
F003 F 0.84301(17) 0.20271(10) 0.72150(8) 0.0308(3) Uani 1 1 d . . . . .
O004 O 1.08920(19) 0.45081(15) 0.65831(10) 0.0337(3) Uani 1 1 d . . . . .
O005 O 0.7311(2) 0.52115(13) 0.58387(10) 0.0318(3) Uani 1 1 d . . . . .
N006 N 0.7821(2) 0.48329(17) 1.03859(11) 0.0297(3) Uani 1 1 d . . . . .
N007 N 0.3068(3) 0.19413(17) 0.83447(13) 0.0338(4) Uani 1 1 d . . . . .
C008 C 0.7098(2) 0.44950(17) 0.95818(13) 0.0222(3) Uani 1 1 d . . . . .
C009 C 0.6124(2) 0.40692(16) 0.85669(12) 0.0203(3) Uani 1 1 d . . . . .
C00A C 0.8391(3) 0.28285(17) 0.51329(12) 0.0234(3) Uani 1 1 d . . . . .
C00B C 0.7425(2) 0.31859(17) 0.69984(12) 0.0211(3) Uani 1 1 d . . . . .
C00C C 0.6659(3) 0.67929(17) 0.82446(12) 0.0220(3) Uani 1 1 d . . . . .
C00D C 0.7631(2) 0.42348(16) 0.78623(12) 0.0200(3) Uani 1 1 d . . . . .
H00D H 0.912081 0.464820 0.816851 0.024 Uiso 1 1 calc R U . . .
C00E C 0.6005(2) 0.52493(16) 0.78642(12) 0.0207(3) Uani 1 1 d . . . . .
H00E H 0.476386 0.507517 0.730769 0.025 Uiso 1 1 calc R U . . .
C00F C 0.6378(3) 0.2482(2) 0.44893(13) 0.0301(4) Uani 1 1 d . . . . .
H00F H 0.519696 0.293216 0.457597 0.036 Uiso 1 1 calc R U . . .
C00G C 1.0182(3) 0.2202(2) 0.50032(15) 0.0311(4) Uani 1 1 d . . . . .
H00G H 1.151350 0.244725 0.543740 0.037 Uiso 1 1 calc R U . . .
C00H C 0.4392(3) 0.28843(17) 0.84202(13) 0.0237(3) Uani 1 1 d . . . . .
C00I C 0.8640(3) 0.75096(19) 0.81857(15) 0.0310(4) Uani 1 1 d . . . . .
H00I H 0.961271 0.701924 0.793041 0.037 Uiso 1 1 calc R U . . .
C00J C 0.5207(3) 0.75406(19) 0.86109(13) 0.0278(4) Uani 1 1 d . . . . .
H00J H 0.386747 0.706956 0.864121 0.033 Uiso 1 1 calc R U . . .
C00K C 0.7728(4) 0.9697(2) 0.88825(15) 0.0390(5) Uani 1 1 d . . . . .
H00K H 0.809227 1.066722 0.910004 0.047 Uiso 1 1 calc R U . . .
C00L C 0.9169(3) 0.8960(2) 0.85085(17) 0.0394(5) Uani 1 1 d . . . . .
H00L H 1.050074 0.943718 0.847232 0.047 Uiso 1 1 calc R U . . .
C00M C 0.5745(4) 0.8994(2) 0.89334(15) 0.0358(4) Uani 1 1 d . . . . .
H00M H 0.477132 0.949005 0.918293 0.043 Uiso 1 1 calc R U . . .
C00N C 0.9948(4) 0.1197(2) 0.42098(16) 0.0396(5) Uani 1 1 d . . . . .
H00N H 1.114039 0.077951 0.410023 0.048 Uiso 1 1 calc R U . . .
C00O C 0.7967(4) 0.0817(2) 0.35874(16) 0.0409(5) Uani 1 1 d . . . . .
H00O H 0.781940 0.012295 0.306862 0.049 Uiso 1 1 calc R U . . .
C00P C 0.6186(4) 0.1454(2) 0.37216(15) 0.0381(5) Uani 1 1 d . . . . .
H00P H 0.485252 0.118735 0.329233 0.046 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 0.0033 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'
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'
S S 0.1246 0.1234 '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
O004 S001 C00A 110.34(8) . . ?
O004 S001 C00B 104.94(8) . . ?
O005 S001 O004 120.45(8) . . ?
O005 S001 C00A 110.47(8) . . ?
O005 S001 C00B 104.41(8) . . ?
C00A S001 C00B 104.74(8) . . ?
N006 C008 C009 178.44(16) . . ?
C008 C009 C00D 116.30(13) . . ?
C008 C009 C00E 117.74(14) . . ?
C008 C009 C00H 112.83(14) . . ?
C00D C009 C00E 57.71(10) . . ?
C00H C009 C00D 121.58(14) . . ?
C00H C009 C00E 120.27(14) . . ?
C00F C00A S001 118.75(13) . . ?
C00G C00A S001 119.38(14) . . ?
C00G C00A C00F 121.85(17) . . ?
F002 C00B S001 107.82(11) . . ?
F002 C00B C00D 112.68(13) . . ?
F003 C00B S001 109.06(11) . . ?
F003 C00B F002 107.00(12) . . ?
F003 C00B C00D 112.66(13) . . ?
C00D C00B S001 107.48(10) . . ?
C00I C00C C00E 121.17(15) . . ?
C00J C00C C00E 119.20(14) . . ?
C00J C00C C00I 119.52(16) . . ?
C009 C00D H00D 114.4 . . ?
C00B C00D C009 122.24(13) . . ?
C00B C00D H00D 114.4 . . ?
C00E C00D C009 61.44(10) . . ?
C00E C00D C00B 119.73(14) . . ?
C00E C00D H00D 114.4 . . ?
C009 C00E H00E 114.6 . . ?
C00C C00E C009 120.38(14) . . ?
C00C C00E H00E 114.6 . . ?
C00D C00E C009 60.85(10) . . ?
C00D C00E C00C 121.53(13) . . ?
C00D C00E H00E 114.6 . . ?
C00A C00F H00F 120.9 . . ?
C00P C00F C00A 118.27(18) . . ?
C00P C00F H00F 120.9 . . ?
C00A C00G H00G 120.8 . . ?
C00A C00G C00N 118.46(19) . . ?
C00N C00G H00G 120.8 . . ?
N007 C00H C009 177.05(19) . . ?
C00C C00I H00I 120.0 . . ?
C00C C00I C00L 119.95(18) . . ?
C00L C00I H00I 120.0 . . ?
C00C C00J H00J 119.9 . . ?
C00C C00J C00M 120.27(17) . . ?
C00M C00J H00J 119.9 . . ?
C00L C00K H00K 120.0 . . ?
C00L C00K C00M 119.96(18) . . ?
C00M C00K H00K 120.0 . . ?
C00I C00L H00L 119.8 . . ?
C00K C00L C00I 120.35(18) . . ?
C00K C00L H00L 119.8 . . ?
C00J C00M H00M 120.0 . . ?
C00K C00M C00J 119.94(18) . . ?
C00K C00M H00M 120.0 . . ?
C00G C00N H00N 119.9 . . ?
C00O C00N C00G 120.29(19) . . ?
C00O C00N H00N 119.9 . . ?
C00N C00O H00O 119.6 . . ?
C00N C00O C00P 120.80(19) . . ?
C00P C00O H00O 119.6 . . ?
C00F C00P C00O 120.3(2) . . ?
C00F C00P H00P 119.9 . . ?
C00O C00P H00P 119.9 . . ?
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
S001 O004 1.4340(13) . ?
S001 O005 1.4269(12) . ?
S001 C00A 1.7453(18) . ?
S001 C00B 1.8531(17) . ?
F002 C00B 1.3537(18) . ?
F003 C00B 1.3465(17) . ?
N006 C008 1.142(2) . ?
N007 C00H 1.139(2) . ?
C008 C009 1.448(2) . ?
C009 C00D 1.535(2) . ?
C009 C00E 1.543(2) . ?
C009 C00H 1.451(2) . ?
C00A C00F 1.396(2) . ?
C00A C00G 1.383(2) . ?
C00B C00D 1.491(2) . ?
C00C C00E 1.495(2) . ?
C00C C00I 1.389(2) . ?
C00C C00J 1.386(2) . ?
C00D H00D 0.9800 . ?
C00D C00E 1.485(2) . ?
C00E H00E 0.9800 . ?
C00F H00F 0.9300 . ?
C00F C00P 1.380(3) . ?
C00G H00G 0.9300 . ?
C00G C00N 1.388(3) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.390(3) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.392(3) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.380(3) . ?
C00K C00M 1.382(3) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00N C00O 1.371(3) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.384(3) . ?
C00P H00P 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
S001 C00A C00F C00P -179.90(14) . . . . ?
S001 C00A C00G C00N -178.52(14) . . . . ?
S001 C00B C00D C009 156.59(12) . . . . ?
S001 C00B C00D C00E 83.49(15) . . . . ?
F002 C00B C00D C009 37.9(2) . . . . ?
F002 C00B C00D C00E -35.16(19) . . . . ?
F003 C00B C00D C009 -83.25(17) . . . . ?
F003 C00B C00D C00E -156.35(13) . . . . ?
O004 S001 C00A C00F -170.08(13) . . . . ?
O004 S001 C00A C00G 8.24(17) . . . . ?
O004 S001 C00B F002 -175.40(10) . . . . ?
O004 S001 C00B F003 -59.55(13) . . . . ?
O004 S001 C00B C00D 62.87(12) . . . . ?
O005 S001 C00A C00F -34.42(16) . . . . ?
O005 S001 C00A C00G 143.91(14) . . . . ?
O005 S001 C00B F002 57.01(12) . . . . ?
O005 S001 C00B F003 172.85(10) . . . . ?
O005 S001 C00B C00D -64.72(12) . . . . ?
C008 C009 C00D C00B 143.52(15) . . . . ?
C008 C009 C00D C00E -107.56(16) . . . . ?
C008 C009 C00E C00C -6.5(2) . . . . ?
C008 C009 C00E C00D 105.07(15) . . . . ?
C009 C00D C00E C00C 109.70(17) . . . . ?
C00A S001 C00B F002 -59.15(12) . . . . ?
C00A S001 C00B F003 56.69(13) . . . . ?
C00A S001 C00B C00D 179.11(10) . . . . ?
C00A C00F C00P C00O -1.6(3) . . . . ?
C00A C00G C00N C00O -1.6(3) . . . . ?
C00B S001 C00A C00F 77.47(14) . . . . ?
C00B S001 C00A C00G -104.20(14) . . . . ?
C00B C00D C00E C009 112.87(15) . . . . ?
C00B C00D C00E C00C -137.43(16) . . . . ?
C00C C00I C00L C00K -0.4(3) . . . . ?
C00C C00J C00M C00K 0.5(3) . . . . ?
C00D C009 C00E C00C -111.54(16) . . . . ?
C00E C009 C00D C00B -108.92(16) . . . . ?
C00E C00C C00I C00L 177.32(17) . . . . ?
C00E C00C C00J C00M -177.42(16) . . . . ?
C00F C00A C00G C00N -0.2(3) . . . . ?
C00G C00A C00F C00P 1.8(3) . . . . ?
C00G C00N C00O C00P 1.8(3) . . . . ?
C00H C009 C00D C00B -0.8(2) . . . . ?
C00H C009 C00D C00E 108.15(17) . . . . ?
C00H C009 C00E C00C 138.07(16) . . . . ?
C00H C009 C00E C00D -110.39(17) . . . . ?
C00I C00C C00E C009 102.98(19) . . . . ?
C00I C00C C00E C00D 30.6(2) . . . . ?
C00I C00C C00J C00M -1.1(3) . . . . ?
C00J C00C C00E C009 -80.80(19) . . . . ?
C00J C00C C00E C00D -153.17(16) . . . . ?
C00J C00C C00I C00L 1.1(3) . . . . ?
C00L C00K C00M C00J 0.2(3) . . . . ?
C00M C00K C00L C00I -0.3(3) . . . . ?
C00N C00O C00P C00F -0.2(3) . . . . ?
