#------------------------------------------------------------------------------
#$Date: 2022-06-10 11:34:20 +0300 (Fri, 10 Jun 2022) $
#$Revision: 275956 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105377.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_8105377
loop_
_publ_author_name
'Zhang, Min'
'Lin, Jin-Yuan'
'Liu, Jing'
'Ruan, Ban-Feng'
_publ_section_title
;
 The crystal structure of
 (E)-2-(4-((4-fluorobenzyl)oxy)styryl)-4,6-dimethoxybenzaldehyde,
 C24H21FO4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1059
_journal_page_last               1061
_journal_paper_doi               10.1515/ncrs-2020-0168
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C24 H21 F O4'
_chemical_formula_sum            'C24 H21 F O4'
_chemical_formula_weight         392.41
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.977(6)
_cell_angle_beta                 92.867(6)
_cell_angle_gamma                97.501(6)
_cell_formula_units_Z            2
_cell_length_a                   6.9734(5)
_cell_length_b                   9.0402(7)
_cell_length_c                   16.0963(12)
_cell_measurement_reflns_used    1918
_cell_measurement_temperature    293.2(4)
_cell_measurement_theta_max      27.7130
_cell_measurement_theta_min      3.8600
_cell_volume                     991.15(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.2(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.8689
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -77.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   25.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   53.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega   40.00   67.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   65.00   91.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   -3.00   96.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
  7 omega   -1.00   90.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  120.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0035135000
_diffrn_orient_matrix_UB_12      0.0632504000
_diffrn_orient_matrix_UB_13      0.0325150000
_diffrn_orient_matrix_UB_21      -0.0813020000
_diffrn_orient_matrix_UB_22      0.0224896000
_diffrn_orient_matrix_UB_23      -0.0204224000
_diffrn_orient_matrix_UB_31      -0.0629134000
_diffrn_orient_matrix_UB_32      -0.0439335000
_diffrn_orient_matrix_UB_33      0.0229472000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6688
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0808
_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
'calc w=1/[σ²(Fo²)+(0.0488P)²+0.0883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                2598
_reflns_number_total             3898
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2020-0168_suppl.cif
_cod_data_source_block           rbf_z32
_cod_original_cell_volume        991.14(12)
_cod_database_code               8105377
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C10(H10), C11(H11), C7(H7), C13(H13), C14(H14), C22(H22),
 C8(H8), C17(H17), C18(H18), C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2016-11-30
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.5972(3) 1.2267(2) 0.10727(12) 0.0379(4) Uani 1 d . . .
C2 C 0.4099(3) 1.1884(2) 0.06510(12) 0.0395(5) Uani 1 d . . .
C3 C 0.3003(3) 1.0513(2) 0.06741(12) 0.0414(5) Uani 1 d . . .
H3 H 0.1775 1.0275 0.0395 0.050 Uiso 1 calc . . R
C4 C 0.3739(3) 0.9491(2) 0.11153(12) 0.0398(5) Uani 1 d . . .
C5 C 0.5543(3) 0.9838(2) 0.15437(12) 0.0404(5) Uani 1 d . . .
H5 H 0.5999 0.9147 0.1849 0.048 Uiso 1 calc . . R
C6 C 0.6693(3) 1.1215(2) 0.15246(12) 0.0379(4) Uani 1 d . . .
C7 C 0.8611(3) 1.1553(2) 0.19862(13) 0.0448(5) Uani 1 d . . .
H7 H 0.9244 1.2533 0.2017 0.054 Uiso 1 calc . . R
C8 C 0.9530(3) 1.0644(2) 0.23565(13) 0.0492(5) Uani 1 d . . .
H8 H 0.8916 0.9653 0.2302 0.059 Uiso 1 calc . . R
C9 C 1.1402(3) 1.0978(2) 0.28477(12) 0.0402(5) Uani 1 d . . .
C10 C 1.2654(3) 1.2314(2) 0.28871(12) 0.0415(5) Uani 1 d . . .
H10 H 1.2343 1.3020 0.2558 0.050 Uiso 1 calc . . R
C11 C 1.4351(3) 1.2625(2) 0.34013(12) 0.0440(5) Uani 1 d . . .
H11 H 1.5165 1.3531 0.3418 0.053 Uiso 1 calc . . R
C12 C 1.4836(3) 1.1584(2) 0.38909(12) 0.0398(5) Uani 1 d . . .
C13 C 1.3651(3) 1.0220(2) 0.38363(14) 0.0501(6) Uani 1 d . . .
H13 H 1.3984 0.9498 0.4150 0.060 Uiso 1 calc . . R
C14 C 1.1985(3) 0.9938(2) 0.33183(14) 0.0516(6) Uani 1 d . . .
H14 H 1.1212 0.9008 0.3281 0.062 Uiso 1 calc . . R
C15 C 1.7612(3) 1.3210(2) 0.45948(15) 0.0613(7) Uani 1 d . . .
H15A H 1.6841 1.4018 0.4746 0.074 Uiso 1 calc . . R
H15B H 1.8226 1.3369 0.4082 0.074 Uiso 1 calc . . R
C16 C 1.9124(3) 1.3218(2) 0.52927(14) 0.0484(5) Uani 1 d . . .
C17 C 1.8995(3) 1.3974(2) 0.60911(15) 0.0574(6) Uani 1 d . . .
H17 H 1.7925 1.4466 0.6207 0.069 Uiso 1 calc . . R
C18 C 2.0418(4) 1.4022(3) 0.67276(15) 0.0633(7) Uani 1 d . . .
H18 H 2.0318 1.4539 0.7267 0.076 Uiso 1 calc . . R
C19 C 2.1950(3) 1.3303(3) 0.65446(17) 0.0675(7) Uani 1 d . . .
C20 C 2.2142(4) 1.2535(4) 0.57634(19) 0.0880(9) Uani 1 d . . .
H20 H 2.3218 1.2046 0.5654 0.106 Uiso 1 calc . . R
C21 C 2.0708(3) 1.2497(3) 0.51377(16) 0.0743(8) Uani 1 d . . .
H21 H 2.0818 1.1973 0.4601 0.089 Uiso 1 calc . . R
C22 C 0.7051(3) 1.3726(2) 0.09843(13) 0.0462(5) Uani 1 d . . .
H22 H 0.6400 1.4313 0.0671 0.055 Uiso 1 calc . . R
C23 C 0.1566(3) 1.2617(3) -0.01881(15) 0.0554(6) Uani 1 d . . .
H23A H 0.1489 1.1728 -0.0608 0.083 Uiso 1 calc . . GR
H23B H 0.1299 1.3457 -0.0452 0.083 Uiso 1 calc . . GR
H23C H 0.0632 1.2447 0.0218 0.083 Uiso 1 calc . . GR
C24 C 0.3203(3) 0.7009(2) 0.14818(16) 0.0627(7) Uani 1 d . . .
H24A H 0.4383 0.6757 0.1250 0.094 Uiso 1 calc . . GR
H24B H 0.2236 0.6129 0.1384 0.094 Uiso 1 calc . . GR
H24C H 0.3437 0.7358 0.2077 0.094 Uiso 1 calc . . GR
F1 F 2.3377(2) 1.3340(2) 0.71552(11) 0.1143(7) Uani 1 d . . .
O1 O 0.8673(2) 1.42731(16) 0.12631(10) 0.0588(4) Uani 1 d . . .
O2 O 0.34692(19) 1.29427(15) 0.02269(10) 0.0551(4) Uani 1 d . . .
O3 O 0.25379(19) 0.81695(15) 0.10873(10) 0.0550(4) Uani 1 d . . .
O4 O 1.64147(19) 1.17957(15) 0.44637(9) 0.0530(4) Uani 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'
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
C4 O3 C24 118.83(15) . .
C2 O2 C23 117.99(14) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C4 C5 C6 120.74(17) . .
C12 O4 C15 118.06(15) . .
C6 C1 C2 118.61(16) . .
C6 C1 C22 124.49(17) . .
C2 C1 C22 116.87(17) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C2 C3 C4 119.58(17) . .
C5 C6 C1 119.18(16) . .
C5 C6 C7 119.54(17) . .
C1 C6 C7 121.27(16) . .
C10 C9 C8 123.69(17) . .
C14 C9 C10 116.53(17) . .
C14 C9 C8 119.77(16) . .
C9 C10 H10 119.1 . .
C11 C10 C9 121.79(17) . .
C11 C10 H10 119.1 . .
C10 C11 H11 120.1 . .
C10 C11 C12 119.78(17) . .
C12 C11 H11 120.1 . .
O3 C4 C5 124.69(17) . .
O3 C4 C3 114.42(16) . .
C5 C4 C3 120.88(16) . .
C6 C7 H7 116.1 . .
C8 C7 C6 127.74(18) . .
C8 C7 H7 116.1 . .
O4 C12 C11 125.37(16) . .
O4 C12 C13 115.15(16) . .
C13 C12 C11 119.46(17) . .
O2 C2 C1 116.24(16) . .
O2 C2 C3 122.76(16) . .
C3 C2 C1 120.99(17) . .
C12 C13 H13 120.2 . .
C14 C13 C12 119.51(18) . .
C14 C13 H13 120.2 . .
C9 C14 H14 118.6 . .
C13 C14 C9 122.80(17) . .
C13 C14 H14 118.6 . .
C1 C22 H22 115.6 . .
O1 C22 C1 128.79(19) . .
O1 C22 H22 115.6 . .
C9 C8 H8 115.8 . .
C7 C8 C9 128.44(18) . .
C7 C8 H8 115.8 . .
O2 C23 H23A 109.5 . .
O2 C23 H23B 109.5 . .
O2 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C17 C16 C15 121.5(2) . .
C21 C16 C17 118.2(2) . .
C21 C16 C15 120.3(2) . .
C16 C17 H17 119.2 . .
C16 C17 C18 121.6(2) . .
C18 C17 H17 119.2 . .
O4 C15 C16 108.33(16) . .
O4 C15 H15A 110.0 . .
O4 C15 H15B 110.0 . .
C16 C15 H15A 110.0 . .
C16 C15 H15B 110.0 . .
H15A C15 H15B 108.4 . .
C17 C18 H18 121.0 . .
C19 C18 C17 118.1(2) . .
C19 C18 H18 121.0 . .
C16 C21 H21 119.5 . .
C16 C21 C20 121.1(2) . .
C20 C21 H21 119.5 . .
O3 C24 H24A 109.5 . .
O3 C24 H24B 109.5 . .
O3 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
F1 C19 C20 118.0(3) . .
C18 C19 F1 119.4(3) . .
C18 C19 C20 122.6(2) . .
C21 C20 H20 120.7 . .
C19 C20 C21 118.5(2) . .
C19 C20 H20 120.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C4 1.360(2) .
O3 C24 1.423(2) .
O2 C2 1.363(2) .
O2 C23 1.429(2) .
C5 H5 0.9300 .
C5 C6 1.395(2) .
C5 C4 1.378(2) .
O4 C12 1.374(2) .
O4 C15 1.413(2) .
C1 C6 1.411(3) .
C1 C2 1.417(2) .
C1 C22 1.461(3) .
C3 H3 0.9300 .
C3 C4 1.383(3) .
C3 C2 1.375(3) .
C6 C7 1.469(2) .
C9 C10 1.386(3) .
C9 C14 1.384(3) .
C9 C8 1.463(2) .
C10 H10 0.9300 .
C10 C11 1.381(2) .
O1 C22 1.208(2) .
C11 H11 0.9300 .
C11 C12 1.381(3) .
C7 H7 0.9300 .
C7 C8 1.301(3) .
C12 C13 1.379(3) .
C13 H13 0.9300 .
C13 C14 1.367(2) .
C14 H14 0.9300 .
C22 H22 0.9300 .
C8 H8 0.9300 .
F1 C19 1.357(2) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C16 C17 1.371(3) .
C16 C15 1.501(3) .
C16 C21 1.368(3) .
C17 H17 0.9300 .
C17 C18 1.381(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C18 H18 0.9300 .
C18 C19 1.343(4) .
C21 H21 0.9300 .
C21 C20 1.376(3) .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C19 C20 1.360(4) .
C20 H20 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
C5 C6 C7 C8 8.4(3) . . . .
O4 C12 C13 C14 176.4(2) . . . .
C1 C6 C7 C8 -172.7(2) . . . .
C6 C5 C4 O3 178.82(18) . . . .
C6 C5 C4 C3 -1.7(3) . . . .
C6 C1 C2 O2 179.75(17) . . . .
C6 C1 C2 C3 -0.4(3) . . . .
C6 C1 C22 O1 0.3(3) . . . .
C6 C7 C8 C9 -177.2(2) . . . .
C9 C10 C11 C12 0.2(3) . . . .
C10 C9 C14 C13 3.5(3) . . . .
C10 C9 C8 C7 -10.4(4) . . . .
C10 C11 C12 O4 -175.84(18) . . . .
C10 C11 C12 C13 2.4(3) . . . .
C11 C12 C13 C14 -2.0(3) . . . .
C4 C5 C6 C1 1.2(3) . . . .
C4 C5 C6 C7 -179.91(19) . . . .
C4 C3 C2 O2 179.78(19) . . . .
C4 C3 C2 C1 0.0(3) . . . .
C12 O4 C15 C16 175.29(18) . . . .
C12 C13 C14 C9 -1.0(4) . . . .
C2 C1 C6 C5 -0.1(3) . . . .
C2 C1 C6 C7 -179.03(17) . . . .
C2 C1 C22 O1 -177.8(2) . . . .
C2 C3 C4 O3 -179.36(17) . . . .
C2 C3 C4 C5 1.1(3) . . . .
C14 C9 C10 C11 -3.1(3) . . . .
C14 C9 C8 C7 168.5(2) . . . .
C22 C1 C6 C5 -178.18(18) . . . .
C22 C1 C6 C7 2.9(3) . . . .
C22 C1 C2 O2 -2.1(3) . . . .
C22 C1 C2 C3 177.76(18) . . . .
C8 C9 C10 C11 175.8(2) . . . .
C8 C9 C14 C13 -175.4(2) . . . .
F1 C19 C20 C21 -179.6(2) . . . .
C23 O2 C2 C1 -178.36(18) . . . .
C23 O2 C2 C3 1.8(3) . . . .
C16 C17 C18 C19 0.0(3) . . . .
C16 C21 C20 C19 0.2(4) . . . .
C17 C16 C15 O4 -103.3(2) . . . .
C17 C16 C21 C20 -0.4(4) . . . .
C17 C18 C19 F1 179.5(2) . . . .
C17 C18 C19 C20 -0.1(4) . . . .
C15 O4 C12 C11 2.7(3) . . . .
C15 O4 C12 C13 -175.6(2) . . . .
C15 C16 C17 C18 -177.88(19) . . . .
C15 C16 C21 C20 177.8(2) . . . .
C18 C19 C20 C21 0.1(4) . . . .
C21 C16 C17 C18 0.3(3) . . . .
C21 C16 C15 O4 78.6(3) . . . .
C24 O3 C4 C5 -3.9(3) . . . .
C24 O3 C4 C3 176.5(2) . . . .
