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#$Date: 2023-07-12 11:15:45 +0300 (Wed, 12 Jul 2023) $
#$Revision: 285179 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107477.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_8107477
loop_
_publ_author_name
'Luo, Han-Lin'
'Li, Wen-Xuan'
'Bai, Xian-Yong'
'Meng, Qing-Guo'
'Hou, Yun'
_publ_section_title
;
 Crystal structure of
 (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one,
 C21H20FNO2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              495
_journal_page_last               497
_journal_paper_doi               10.1515/ncrs-2023-0053
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C21 H20 F N O2'
_chemical_formula_sum            'C21 H20 F N O2'
_chemical_formula_weight         337.38
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                103.880(7)
_cell_angle_beta                 100.987(7)
_cell_angle_gamma                115.090(7)
_cell_formula_units_Z            2
_cell_length_a                   9.2201(7)
_cell_length_b                   9.3195(8)
_cell_length_c                   11.4012(9)
_cell_measurement_reflns_used    2602
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6850
_cell_measurement_theta_min      2.6050
_cell_volume                     812.32(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5331
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         2.586
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.031(4)
_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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0421
_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)+(0.0613P)²+0.0106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2363
_reflns_number_total             3015
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0053_suppl.cif
_cod_data_source_block           L4
_cod_original_cell_volume        812.32(12)
_cod_database_code               8107477
_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   0.989
_shelx_estimated_absorpt_t_max   0.990
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
C1 C 0.56397(17) 1.19487(19) 0.63909(14) 0.0264(3) Uani 1 1 d . . . . .
C2 C 0.40275(17) 1.08726(18) 0.65534(14) 0.0268(3) Uani 1 1 d . . . . .
C3 C 0.24048(17) 1.01839(19) 0.54719(15) 0.0295(4) Uani 1 1 d . . . . .
H3A H 0.145851 0.984535 0.579472 0.035 Uiso 1 1 calc R U . . .
H3B H 0.222835 0.918155 0.482222 0.035 Uiso 1 1 calc R U . . .
C4 C 0.24340(17) 1.14812(19) 0.48648(15) 0.0310(4) Uani 1 1 d . . . . .
H4A H 0.146647 1.091689 0.408305 0.037 Uiso 1 1 calc R U . . .
H4B H 0.231542 1.234177 0.544562 0.037 Uiso 1 1 calc R U . . .
C5 C 0.40381(18) 1.2947(2) 0.35557(15) 0.0335(4) Uani 1 1 d . . . . .
H5 H 0.301791 1.274575 0.302513 0.040 Uiso 1 1 calc R U . . .
C6 C 0.55297(19) 1.3851(2) 0.33312(15) 0.0359(4) Uani 1 1 d . . . . .
H6 H 0.552333 1.425014 0.265812 0.043 Uiso 1 1 calc R U . . .
C7 C 0.70260(17) 1.41380(19) 0.41397(15) 0.0301(4) Uani 1 1 d . . . . .
C8 C 0.70804(17) 1.35272(18) 0.51109(14) 0.0278(4) Uani 1 1 d . . . . .
H8 H 0.810702 1.372226 0.562599 0.033 Uiso 1 1 calc R U . . .
C9 C 0.55638(16) 1.26018(17) 0.53188(14) 0.0246(3) Uani 1 1 d . . . . .
C10 C 0.40287(17) 1.23331(18) 0.45558(14) 0.0272(3) Uani 1 1 d . . . . .
C11 C 0.41659(18) 1.06564(19) 0.76909(15) 0.0290(4) Uani 1 1 d . . . . .
H11 H 0.527895 1.120775 0.824305 0.035 Uiso 1 1 calc R U . . .
C12 C 0.29142(18) 0.97297(19) 0.82209(14) 0.0284(3) Uani 1 1 d . . . . .
C13 C 0.33310(18) 1.03022(19) 0.95568(14) 0.0312(4) Uani 1 1 d . . . . .
H13 H 0.438261 1.124989 1.005246 0.037 Uiso 1 1 calc R U . . .
C14 C 0.22585(17) 0.95279(19) 1.01631(14) 0.0310(4) Uani 1 1 d . . . . .
H14 H 0.257798 0.998772 1.105025 0.037 Uiso 1 1 calc R U . . .
C15 C 0.06777(17) 0.80456(18) 0.94679(14) 0.0265(3) Uani 1 1 d . . . . .
C16 C 0.02699(18) 0.74408(18) 0.81312(14) 0.0295(4) Uani 1 1 d . . . . .
H16 H -0.075580 0.645934 0.763587 0.035 Uiso 1 1 calc R U . . .
C17 C 0.13453(17) 0.82593(19) 0.75324(14) 0.0299(4) Uani 1 1 d . . . . .
H17 H 0.101848 0.782103 0.664372 0.036 Uiso 1 1 calc R U . . .
C18 C -0.01093(18) 0.81091(19) 1.14081(14) 0.0315(4) Uani 1 1 d . . . . .
H18A H -0.050767 0.892291 1.143258 0.038 Uiso 1 1 calc R U . . .
H18B H 0.109467 0.873045 1.189358 0.038 Uiso 1 1 calc R U . . .
C19 C -0.10442(19) 0.6894(2) 1.20107(16) 0.0427(4) Uani 1 1 d . . . . .
H19A H -0.055334 0.616601 1.207199 0.051 Uiso 1 1 calc R U . . .
H19B H -0.089887 0.753469 1.287273 0.051 Uiso 1 1 calc R U . . .
C20 C -0.2997(2) 0.4894(2) 1.00609(17) 0.0417(4) Uani 1 1 d . . . . .
H20A H -0.419576 0.415885 0.957357 0.050 Uiso 1 1 calc R U . . .
H20B H -0.249243 0.417988 1.013519 0.050 Uiso 1 1 calc R U . . .
C21 C -0.21681(18) 0.6007(2) 0.93542(16) 0.0386(4) Uani 1 1 d . . . . .
H21A H -0.227185 0.529976 0.853037 0.046 Uiso 1 1 calc R U . . .
H21B H -0.275024 0.663445 0.920018 0.046 Uiso 1 1 calc R U . . .
F1 F 0.85045(10) 1.50772(11) 0.39625(10) 0.0426(3) Uani 1 1 d . . . . .
N1 N -0.03751(14) 0.71990(15) 1.00812(11) 0.0294(3) Uani 1 1 d . . . . .
O1 O 0.70278(12) 1.23344(15) 0.71052(11) 0.0407(3) Uani 1 1 d . . . . .
O2 O -0.28086(13) 0.58668(15) 1.13005(11) 0.0442(3) Uani 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 C2 122.63(14) . .
O1 C1 C9 119.11(12) . .
C2 C1 C9 118.26(12) . .
C11 C2 C1 115.68(13) . .
C11 C2 C3 126.61(13) . .
C1 C2 C3 117.67(13) . .
C2 C3 C4 112.29(12) . .
C10 C4 C3 113.42(11) . .
C6 C5 C10 121.66(14) . .
C7 C6 C5 117.84(15) . .
F1 C7 C8 118.71(13) . .
F1 C7 C6 118.51(14) . .
C8 C7 C6 122.78(14) . .
C7 C8 C9 118.79(13) . .
C10 C9 C8 120.44(14) . .
C10 C9 C1 121.21(12) . .
C8 C9 C1 118.34(12) . .
C5 C10 C9 118.42(13) . .
C5 C10 C4 121.53(13) . .
C9 C10 C4 119.96(14) . .
C2 C11 C12 132.54(14) . .
C17 C12 C13 115.80(14) . .
C17 C12 C11 126.44(14) . .
C13 C12 C11 117.68(13) . .
C14 C13 C12 122.87(14) . .
C13 C14 C15 121.22(14) . .
N1 C15 C16 122.22(13) . .
N1 C15 C14 121.53(13) . .
C16 C15 C14 116.19(13) . .
C17 C16 C15 121.90(14) . .
C16 C17 C12 121.97(14) . .
N1 C18 C19 110.84(13) . .
O2 C19 C18 112.40(13) . .
O2 C20 C21 111.75(13) . .
N1 C21 C20 111.38(13) . .
C15 N1 C21 119.16(12) . .
C15 N1 C18 118.67(12) . .
C21 N1 C18 112.14(11) . .
C20 O2 C19 108.31(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2258(17) .
C1 C2 1.476(2) .
C1 C9 1.493(2) .
C2 C11 1.350(2) .
C2 C3 1.5078(19) .
C3 C4 1.524(2) .
C4 C10 1.503(2) .
C5 C6 1.386(2) .
C5 C10 1.393(2) .
C6 C7 1.381(2) .
C7 F1 1.3576(16) .
C7 C8 1.363(2) .
C8 C9 1.399(2) .
C9 C10 1.396(2) .
C11 C12 1.454(2) .
C12 C17 1.399(2) .
C12 C13 1.402(2) .
C13 C14 1.368(2) .
C14 C15 1.410(2) .
C15 N1 1.3884(19) .
C15 C16 1.404(2) .
C16 C17 1.378(2) .
C18 N1 1.4611(18) .
C18 C19 1.506(2) .
C19 O2 1.4226(18) .
C20 O2 1.417(2) .
C20 C21 1.507(2) .
C21 N1 1.4603(18) .
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
C21 H21A O1 0.97 2.57 3.428(2) 146.9 1_445 yes
C18 H18B O1 0.97 2.56 3.2577(18) 129.3 2_677 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C11 14.7(2) . . . .
C9 C1 C2 C11 -164.67(13) . . . .
O1 C1 C2 C3 -167.49(13) . . . .
C9 C1 C2 C3 13.15(18) . . . .
C11 C2 C3 C4 137.96(15) . . . .
C1 C2 C3 C4 -39.59(16) . . . .
C2 C3 C4 C10 48.01(17) . . . .
C10 C5 C6 C7 -0.4(2) . . . .
C5 C6 C7 F1 -177.48(12) . . . .
C5 C6 C7 C8 2.1(2) . . . .
F1 C7 C8 C9 178.13(12) . . . .
C6 C7 C8 C9 -1.5(2) . . . .
C7 C8 C9 C10 -0.9(2) . . . .
C7 C8 C9 C1 -179.60(13) . . . .
O1 C1 C9 C10 -173.86(13) . . . .
C2 C1 C9 C10 5.5(2) . . . .
O1 C1 C9 C8 4.8(2) . . . .
C2 C1 C9 C8 -175.84(12) . . . .
C6 C5 C10 C9 -1.9(2) . . . .
C6 C5 C10 C4 174.85(14) . . . .
C8 C9 C10 C5 2.6(2) . . . .
C1 C9 C10 C5 -178.82(13) . . . .
C8 C9 C10 C4 -174.24(12) . . . .
C1 C9 C10 C4 4.4(2) . . . .
C3 C4 C10 C5 151.69(14) . . . .
C3 C4 C10 C9 -31.6(2) . . . .
C1 C2 C11 C12 179.24(14) . . . .
C3 C2 C11 C12 1.6(3) . . . .
C2 C11 C12 C17 30.0(3) . . . .
C2 C11 C12 C13 -153.15(16) . . . .
C17 C12 C13 C14 -2.5(2) . . . .
C11 C12 C13 C14 -179.71(13) . . . .
C12 C13 C14 C15 2.7(2) . . . .
C13 C14 C15 N1 176.33(12) . . . .
C13 C14 C15 C16 -1.0(2) . . . .
N1 C15 C16 C17 -177.96(12) . . . .
C14 C15 C16 C17 -0.7(2) . . . .
C15 C16 C17 C12 0.7(2) . . . .
C13 C12 C17 C16 0.8(2) . . . .
C11 C12 C17 C16 177.73(13) . . . .
N1 C18 C19 O2 -55.64(17) . . . .
O2 C20 C21 N1 56.09(17) . . . .
C16 C15 N1 C21 -21.0(2) . . . .
C14 C15 N1 C21 161.80(13) . . . .
C16 C15 N1 C18 -163.89(12) . . . .
C14 C15 N1 C18 18.95(19) . . . .
C20 C21 N1 C15 165.35(13) . . . .
C20 C21 N1 C18 -49.55(17) . . . .
C19 C18 N1 C15 -165.63(12) . . . .
C19 C18 N1 C21 49.08(16) . . . .
C21 C20 O2 C19 -60.79(16) . . . .
C18 C19 O2 C20 60.98(17) . . . .
