#------------------------------------------------------------------------------
#$Date: 2019-11-17 12:30:52 +0100 (dom 17 de nov de 2019) $
#$Revision: 230175 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/79/7057923.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_7057923
loop_
_publ_author_name
'Zhang, Zhenfeng'
'Ma, Nana'
_publ_section_title
;
 A scarce CC⋯CN π-hole interaction in (E)-isomers
 of 3-[(4-halogenphenyl)amino]-2-cyanoprop-2-enoates
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19995
_journal_paper_doi               10.1039/C8NJ04000A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C12 H11 F N2 O2'
_chemical_formula_sum            'C12 H11 F N2 O2'
_chemical_formula_weight         234.23
_chemical_name_systematic
;
ethyl (2E)-2-cyano-3-[(4-fluorophenyl)amino]prop-2-enoate
;
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc1pjlsl
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-08-07 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                80.459(4)
_cell_angle_beta                 85.215(4)
_cell_angle_gamma                73.346(4)
_cell_formula_units_Z            4
_cell_length_a                   7.0897(3)
_cell_length_b                   11.9762(6)
_cell_length_c                   14.5170(7)
_cell_measurement_reflns_used    5944
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.8870
_cell_measurement_theta_min      3.8840
_cell_volume                     1163.72(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia,2012)'
_computing_publication_material  'Bruker SHELXTL(Bruker, 2002)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30162
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         29.126
_diffrn_reflns_theta_min         3.371
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9427
_exptl_absorpt_correction_T_min  0.9157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0040(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0671
_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)+(0.0322P)²+0.5416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3746
_reflns_number_total             5793
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj04000a4.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7057923--7057924.cif.'
_cod_database_code               7057923
_shelx_shelxl_version_number     2017/1
_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   0.970
_shelx_estimated_absorpt_t_max   0.980
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
N2 N 0.2597(4) 0.59144(17) 0.58081(14) 0.0646(6) Uani 1 1 d . .
N2' N 0.2848(4) 0.72712(18) 0.37606(15) 0.0672(6) Uani 1 1 d . .
O2' O 0.3235(2) 0.99566(12) 0.27530(9) 0.0469(4) Uani 1 1 d . .
O2 O 0.2191(2) 0.32888(12) 0.69032(10) 0.0525(4) Uani 1 1 d . .
F1 F 0.2353(3) 0.48168(14) -0.00622(9) 0.0805(5) Uani 1 1 d . .
O1 O 0.2221(3) 0.20445(13) 0.59008(11) 0.0594(5) Uani 1 1 d . .
F1' F 0.1717(3) 0.84824(15) 0.97148(10) 0.0902(6) Uani 1 1 d . .
N1 N 0.2540(3) 0.47608(16) 0.37191(12) 0.0442(4) Uani 1 1 d . .
N1' N 0.2499(3) 0.84332(16) 0.59171(12) 0.0459(4) Uani 1 1 d . .
O1' O 0.2771(3) 1.11963(14) 0.38009(11) 0.0707(5) Uani 1 1 d . .
C2 C 0.2395(3) 0.39851(17) 0.53365(14) 0.0402(5) Uani 1 1 d . .
C3 C 0.2403(3) 0.39076(18) 0.44122(14) 0.0408(5) Uani 1 1 d . .
C5 C 0.2479(3) 0.47397(17) 0.27543(14) 0.0402(5) Uani 1 1 d . .
C1' C 0.2924(3) 1.02259(18) 0.36210(15) 0.0444(5) Uani 1 1 d . .
C4 C 0.2512(3) 0.50399(18) 0.56182(14) 0.0443(5) Uani 1 1 d . .
C2' C 0.2764(3) 0.92131(18) 0.43024(14) 0.0422(5) Uani 1 1 d . .
C4' C 0.2818(3) 0.81440(19) 0.39844(15) 0.0465(5) Uani 1 1 d . .
C5' C 0.2303(3) 0.84960(18) 0.68849(14) 0.0418(5) Uani 1 1 d . .
C3' C 0.2607(3) 0.92997(19) 0.52333(15) 0.0439(5) Uani 1 1 d . .
C6 C 0.1579(4) 0.40241(19) 0.24146(16) 0.0491(6) Uani 1 1 d . .
C6' C 0.1631(3) 0.9546(2) 0.72401(16) 0.0478(5) Uani 1 1 d . .
C1 C 0.2261(3) 0.29971(17) 0.60483(14) 0.0421(5) Uani 1 1 d . .
C8 C 0.2406(4) 0.4788(2) 0.08773(15) 0.0543(6) Uani 1 1 d . .
C10 C 0.3338(4) 0.5484(2) 0.21422(17) 0.0547(6) Uani 1 1 d . .
C11' C 0.3203(4) 1.0940(2) 0.20182(16) 0.0508(6) Uani 1 1 d . .
C10' C 0.2769(4) 0.7439(2) 0.74934(17) 0.0503(6) Uani 1 1 d . .
C7' C 0.1428(4) 0.9536(2) 0.81966(17) 0.0543(6) Uani 1 1 d . .
C7 C 0.1556(4) 0.4046(2) 0.14579(16) 0.0545(6) Uani 1 1 d . .
C8' C 0.1915(4) 0.8482(2) 0.87727(15) 0.0557(6) Uani 1 1 d . .
C9' C 0.2583(4) 0.7434(2) 0.84395(17) 0.0569(6) Uani 1 1 d . .
C9 C 0.3294(4) 0.5510(2) 0.11948(17) 0.0611(7) Uani 1 1 d . .
C11 C 0.2021(5) 0.2388(2) 0.76734(17) 0.0610(7) Uani 1 1 d . .
C12' C 0.3691(4) 1.0454(3) 0.11121(16) 0.0721(8) Uani 1 1 d . .
H12D H 0.274723 1.005112 0.101797 0.108 Uiso 1 1 calc R U
H12F H 0.498618 0.991231 0.113128 0.108 Uiso 1 1 calc R U
H12E H 0.365254 1.108816 0.060718 0.108 Uiso 1 1 calc R U
C12 C 0.2307(5) 0.2799(3) 0.85404(17) 0.0869(10) Uani 1 1 d . .
H12B H 0.145363 0.357978 0.855754 0.130 Uiso 1 1 calc R U
H12A H 0.365276 0.280936 0.855770 0.130 Uiso 1 1 calc R U
H12C H 0.200155 0.227637 0.907059 0.130 Uiso 1 1 calc R U
H6' H 0.125(3) 1.026(2) 0.6847(15) 0.051(6) Uiso 1 1 d . .
H10' H 0.324(3) 0.675(2) 0.7218(15) 0.056(7) Uiso 1 1 d . .
H1 H 0.272(3) 0.537(2) 0.3871(15) 0.052(7) Uiso 1 1 d . .
H3 H 0.232(3) 0.3190(18) 0.4231(13) 0.042(6) Uiso 1 1 d . .
H3' H 0.256(3) 1.0029(19) 0.5457(15) 0.051(6) Uiso 1 1 d . .
H9' H 0.293(4) 0.668(2) 0.8866(18) 0.077(8) Uiso 1 1 d . .
H11C H 0.421(3) 1.131(2) 0.2171(16) 0.060(7) Uiso 1 1 d . .
H11D H 0.185(4) 1.150(2) 0.2030(15) 0.059(7) Uiso 1 1 d . .
H6 H 0.092(3) 0.355(2) 0.2822(16) 0.060(7) Uiso 1 1 d . .
H7 H 0.087(4) 0.355(2) 0.1205(16) 0.067(7) Uiso 1 1 d . .
H9 H 0.388(4) 0.601(2) 0.0750(19) 0.087(9) Uiso 1 1 d . .
H10 H 0.397(4) 0.594(2) 0.2417(17) 0.074(8) Uiso 1 1 d . .
H1' H 0.261(3) 0.771(2) 0.5753(16) 0.062(7) Uiso 1 1 d . .
H7' H 0.093(4) 1.022(2) 0.8477(17) 0.069(8) Uiso 1 1 d . .
H11A H 0.301(3) 0.166(2) 0.7562(16) 0.059(7) Uiso 1 1 d . .
H11B H 0.063(5) 0.228(3) 0.769(2) 0.100(11) Uiso 1 1 d . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1' O2' C11' 115.38(16)
C1 O2 C11 116.01(17)
C3 N1 C5 126.92(19)
C3 N1 H1 116.6(15)
C5 N1 H1 116.4(15)
C3' N1' C5' 126.60(19)
C3' N1' H1' 117.4(15)
C5' N1' H1' 115.9(15)
C3 C2 C4 119.97(18)
C3 C2 C1 120.95(18)
C4 C2 C1 119.08(18)
N1 C3 C2 124.8(2)
N1 C3 H3 116.0(12)
C2 C3 H3 119.2(12)
C6 C5 C10 120.0(2)
C6 C5 N1 122.20(18)
C10 C5 N1 117.8(2)
O1' C1' O2' 123.28(19)
O1' C1' C2' 125.2(2)
O2' C1' C2' 111.55(17)
N2 C4 C2 177.2(2)
C3' C2' C4' 121.21(19)
C3' C2' C1' 119.57(19)
C4' C2' C1' 119.21(18)
N2' C4' C2' 177.6(2)
C6' C5' C10' 119.6(2)
C6' C5' N1' 123.03(19)
C10' C5' N1' 117.4(2)
N1' C3' C2' 125.0(2)
N1' C3' H3' 113.2(13)
C2' C3' H3' 121.8(13)
C5 C6 C7 119.6(2)
C5 C6 H6 120.9(14)
C7 C6 H6 119.4(14)
C5' C6' C7' 119.8(2)
C5' C6' H6' 120.9(14)
C7' C6' H6' 119.2(14)
O1 C1 O2 123.93(18)
O1 C1 C2 125.52(19)
O2 C1 C2 110.56(17)
C7 C8 C9 122.7(2)
C7 C8 F1 118.6(2)
C9 C8 F1 118.8(2)
C9 C10 C5 120.1(2)
C9 C10 H10 123.6(15)
C5 C10 H10 116.3(15)
O2' C11' C12' 107.4(2)
O2' C11' H11C 106.3(13)
C12' C11' H11C 112.3(13)
O2' C11' H11D 107.5(13)
C12' C11' H11D 112.0(13)
H11C C11' H11D 111.0(19)
C9' C10' C5' 120.5(2)
C9' C10' H10' 123.0(14)
C5' C10' H10' 116.5(14)
C8' C7' C6' 119.0(2)
C8' C7' H7' 117.5(15)
C6' C7' H7' 123.5(15)
C8 C7 C6 118.9(2)
C8 C7 H7 120.9(14)
C6 C7 H7 120.1(14)
C9' C8' F1' 119.1(2)
C9' C8' C7' 122.3(2)
F1' C8' C7' 118.6(2)
C8' C9' C10' 118.8(2)
C8' C9' H9' 121.4(15)
C10' C9' H9' 119.8(15)
C8 C9 C10 118.7(2)
C8 C9 H9 118.8(17)
C10 C9 H9 122.5(17)
O2 C11 C12 107.6(2)
O2 C11 H11A 107.4(14)
C12 C11 H11A 113.2(14)
O2 C11 H11B 108.8(17)
C12 C11 H11B 109.7(17)
H11A C11 H11B 110(2)
C11' C12' H12D 109.5
C11' C12' H12F 109.5
H12D C12' H12F 109.5
C11' C12' H12E 109.5
H12D C12' H12E 109.5
H12F C12' H12E 109.5
C11 C12 H12B 109.5
C11 C12 H12A 109.5
H12B C12 H12A 109.5
C11 C12 H12C 109.5
H12B C12 H12C 109.5
H12A C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C4 1.145(3)
N2' C4' 1.139(3)
O2' C1' 1.337(2)
O2' C11' 1.448(2)
O2 C1 1.337(2)
O2 C11 1.442(3)
F1 C8 1.362(2)
O1 C1 1.204(2)
F1' C8' 1.363(3)
N1 C3 1.329(2)
N1 C5 1.410(3)
N1 H1 0.85(2)
N1' C3' 1.326(3)
N1' C5' 1.413(3)
N1' H1' 0.92(2)
O1' C1' 1.206(2)
C2 C3 1.360(3)
C2 C4 1.417(3)
C2 C1 1.456(3)
C3 H3 0.96(2)
C5 C6 1.375(3)
C5 C10 1.384(3)
C1' C2' 1.458(3)
C2' C3' 1.365(3)
C2' C4' 1.421(3)
C5' C6' 1.380(3)
C5' C10' 1.389(3)
C3' H3' 0.97(2)
C6 C7 1.386(3)
C6 H6 0.94(2)
C6' C7' 1.382(3)
C6' H6' 0.93(2)
C8 C7 1.356(3)
C8 C9 1.360(3)
C10 C9 1.373(3)
C10 H10 0.95(3)
C11' C12' 1.500(3)
C11' H11C 0.99(2)
C11' H11D 1.00(2)
C10' C9' 1.368(3)
C10' H10' 0.94(2)
C7' C8' 1.364(3)
C7' H7' 0.94(3)
C7 H7 1.00(2)
C8' C9' 1.362(3)
C9' H9' 0.99(3)
C9 H9 0.96(3)
C11 C12 1.474(4)
C11 H11A 0.97(2)
C11 H11B 1.03(3)
C12' H12D 0.9600
C12' H12F 0.9600
C12' H12E 0.9600
C12 H12B 0.9600
C12 H12A 0.9600
C12 H12C 0.9600
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
_geom_hbond_publ_flag
N1 H1 N2' 0.85(2) 2.28(2) 3.087(3) 160(2) . yes
N1' H1' N2 0.92(2) 2.14(3) 3.027(3) 163(2) . yes
C3 H3 O1' 0.96(2) 2.49(2) 3.439(3) 169.6(16) 1_545 yes
C3' H3' O1 0.97(2) 2.54(2) 3.509(3) 174.3(17) 1_565 yes
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
C5 N1 C3 C2 -177.4(2)
C4 C2 C3 N1 0.9(3)
C1 C2 C3 N1 -179.3(2)
C3 N1 C5 C6 24.1(3)
C3 N1 C5 C10 -156.8(2)
C11' O2' C1' O1' -5.4(3)
C11' O2' C1' C2' 173.62(19)
O1' C1' C2' C3' -6.4(4)
O2' C1' C2' C3' 174.59(19)
O1' C1' C2' C4' 175.0(2)
O2' C1' C2' C4' -4.0(3)
C3' N1' C5' C6' 19.5(3)
C3' N1' C5' C10' -162.2(2)
C5' N1' C3' C2' -178.9(2)
C4' C2' C3' N1' 0.2(4)
C1' C2' C3' N1' -178.4(2)
C10 C5 C6 C7 0.6(4)
N1 C5 C6 C7 179.6(2)
C10' C5' C6' C7' 0.0(3)
N1' C5' C6' C7' 178.3(2)
C11 O2 C1 O1 -1.2(3)
C11 O2 C1 C2 179.0(2)
C3 C2 C1 O1 2.9(4)
C4 C2 C1 O1 -177.3(2)
C3 C2 C1 O2 -177.25(19)
C4 C2 C1 O2 2.5(3)
C6 C5 C10 C9 0.0(4)
N1 C5 C10 C9 -179.1(2)
C1' O2' C11' C12' 176.8(2)
C6' C5' C10' C9' -0.6(3)
N1' C5' C10' C9' -179.0(2)
C5' C6' C7' C8' 0.5(4)
C9 C8 C7 C6 0.4(4)
F1 C8 C7 C6 -179.1(2)
C5 C6 C7 C8 -0.8(4)
C6' C7' C8' C9' -0.5(4)
C6' C7' C8' F1' 179.8(2)
F1' C8' C9' C10' 179.7(2)
C7' C8' C9' C10' -0.1(4)
C5' C10' C9' C8' 0.7(4)
C7 C8 C9 C10 0.2(4)
F1 C8 C9 C10 179.7(2)
C5 C10 C9 C8 -0.4(4)
C1 O2 C11 C12 170.5(2)
