#------------------------------------------------------------------------------
#$Date: 2021-03-28 09:00:31 +0300 (Sun, 28 Mar 2021) $
#$Revision: 263398 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/13/1561313.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1561313
loop_
_publ_author_name
'Shirmila, D. Angeline'
'Jonathan, D. Reuben'
'Priya, M. Krishna'
'Hemalatha, J.'
'Usha, G.'
_publ_section_title
;
 (2E)-2-(3,4-Dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one
;
_journal_coeditor_code           HB4379
_journal_issue                   3
_journal_name_full               IUCrData
_journal_page_first              x210309
_journal_paper_doi               10.1107/S2414314621003096
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C19 H18 O3'
_chemical_formula_moiety         'C19 H18 O3'
_chemical_formula_sum            'C19 H18 O3'
_chemical_formula_weight         294.33
_chemical_name_systematic
(2E)-2-(3,4-Dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9229(15)
_cell_length_b                   9.4474(19)
_cell_length_c                   20.875(4)
_cell_measurement_reflns_used    9801
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.91
_cell_volume                     1562.5(5)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/4 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX3 CMOS '
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34283
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_min         3.356
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.230
_refine_ls_abs_structure_details
;
Flack x determined using 1195 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_coef       0.35(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0566
_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)+(0.1074P)²+0.3866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1800
_reflns_number_gt                3101
_reflns_number_total             3886
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4379sup1.cif
_cod_data_source_block           I
_cod_database_code               1561313
_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   0.983
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O2 0.6008(3) 0.1479(3) 0.28091(12) 0.0624(7) Uani d 1 . .
O O3 0.8450(3) -0.0282(3) 0.26479(12) 0.0649(7) Uani d 1 . .
O O1 0.9071(4) 0.4782(3) 0.59032(11) 0.0649(7) Uani d 1 . .
C C13 0.7334(4) 0.2526(3) 0.37495(14) 0.0458(6) Uani d 1 . .
H H13 0.644379 0.315256 0.381066 0.055 Uiso calc 1 . .
C C14 0.7278(4) 0.1574(3) 0.32452(14) 0.0464(7) Uani d 1 . .
C C16 0.9976(4) 0.0639(3) 0.35657(16) 0.0519(7) Uani d 1 . .
H H16 1.087221 0.001746 0.350367 0.062 Uiso calc 1 . .
C C15 0.8614(4) 0.0615(3) 0.31555(14) 0.0479(7) Uani d 1 . .
C C8 0.8296(4) 0.4838(3) 0.48040(13) 0.0441(6) Uani d 1 . .
C C17 1.0009(4) 0.1591(3) 0.40715(15) 0.0503(7) Uani d 1 . .
H H17 1.092160 0.158070 0.435149 0.060 Uiso calc 1 . .
C C6 0.8282(4) 0.7030(3) 0.55210(13) 0.0446(6) Uani d 1 . .
C C12 0.8722(4) 0.2556(3) 0.41712(14) 0.0449(6) Uani d 1 . .
C C5 0.8007(4) 0.7892(3) 0.49871(15) 0.0475(7) Uani d 1 . .
C C11 0.8832(4) 0.3505(3) 0.47233(14) 0.0471(7) Uani d 1 . .
H H11 0.936499 0.311604 0.507916 0.057 Uiso calc 1 . .
C C7 0.8610(4) 0.5492(3) 0.54443(13) 0.0467(7) Uani d 1 . .
C C10 0.8113(5) 0.7267(3) 0.43275(15) 0.0533(7) Uani d 1 . .
H H10A 0.927775 0.728510 0.418478 0.064 Uiso calc 1 . .
H H10B 0.745607 0.784317 0.403441 0.064 Uiso calc 1 . .
C C9 0.7464(4) 0.5751(3) 0.43063(15) 0.0510(7) Uani d 1 . .
H H9A 0.625376 0.575024 0.437596 0.061 Uiso calc 1 . .
H H9B 0.767737 0.535552 0.388515 0.061 Uiso calc 1 . .
C C1 0.8256(4) 0.7620(4) 0.61349(16) 0.0545(8) Uani d 1 . .
H H1 0.844547 0.704442 0.648899 0.065 Uiso calc 1 . .
C C4 0.7687(4) 0.9330(4) 0.50842(18) 0.0566(8) Uani d 1 . .
H H4 0.748799 0.991456 0.473385 0.068 Uiso calc 1 . .
C C2 0.7953(5) 0.9042(4) 0.62230(18) 0.0616(9) Uani d 1 . .
H H2 0.794300 0.942688 0.663314 0.074 Uiso calc 1 . .
C C3 0.7665(5) 0.9893(4) 0.5695(2) 0.0636(9) Uani d 1 . .
H H3 0.745332 1.085375 0.575098 0.076 Uiso calc 1 . .
C C18 0.4641(5) 0.2440(5) 0.2858(2) 0.0755(12) Uani d 1 . .
H H18A 0.384295 0.225412 0.252249 0.113 Uiso calc 1 . .
H H18B 0.410051 0.232675 0.326635 0.113 Uiso calc 1 . .
H H18C 0.505437 0.339161 0.281840 0.113 Uiso calc 1 . .
C C19 0.9838(8) -0.1150(5) 0.2497(3) 0.0900(15) Uani d 1 . .
H H19A 0.956607 -0.172841 0.213369 0.135 Uiso calc 1 . .
H H19B 1.079682 -0.056856 0.239872 0.135 Uiso calc 1 . .
H H19C 1.009656 -0.174440 0.285713 0.135 Uiso calc 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O2 C18 . . 118.3(3) ?
C15 O3 C19 . . 117.5(3) ?
C14 C13 C12 . . 120.9(3) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
O2 C14 C13 . . 125.1(3) ?
O2 C14 C15 . . 115.2(3) ?
C13 C14 C15 . . 119.7(3) ?
C15 C16 C17 . . 119.9(3) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
O3 C15 C16 . . 124.6(3) ?
O3 C15 C14 . . 115.6(3) ?
C16 C15 C14 . . 119.8(3) ?
C11 C8 C7 . . 116.6(3) ?
C11 C8 C9 . . 126.3(3) ?
C7 C8 C9 . . 117.0(3) ?
C12 C17 C16 . . 121.9(3) ?
C12 C17 H17 . . 119.1 ?
C16 C17 H17 . . 119.1 ?
C5 C6 C1 . . 119.8(3) ?
C5 C6 C7 . . 120.8(2) ?
C1 C6 C7 . . 119.5(3) ?
C17 C12 C13 . . 117.9(3) ?
C17 C12 C11 . . 118.6(3) ?
C13 C12 C11 . . 123.5(3) ?
C4 C5 C6 . . 118.6(3) ?
C4 C5 C10 . . 121.7(3) ?
C6 C5 C10 . . 119.6(3) ?
C8 C11 C12 . . 131.0(3) ?
C8 C11 H11 . . 114.5 ?
C12 C11 H11 . . 114.5 ?
O1 C7 C6 . . 120.2(3) ?
O1 C7 C8 . . 121.5(3) ?
C6 C7 C8 . . 118.2(2) ?
C5 C10 C9 . . 112.2(3) ?
C5 C10 H10A . . 109.2 ?
C9 C10 H10A . . 109.2 ?
C5 C10 H10B . . 109.2 ?
C9 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
C8 C9 C10 . . 111.8(3) ?
C8 C9 H9A . . 109.2 ?
C10 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
C2 C1 C6 . . 121.0(3) ?
C2 C1 H1 . . 119.5 ?
C6 C1 H1 . . 119.5 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C1 C2 C3 . . 119.3(3) ?
C1 C2 H2 . . 120.4 ?
C3 C2 H2 . . 120.4 ?
C4 C3 C2 . . 120.6(3) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
O2 C18 H18A . . 109.5 ?
O2 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O2 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O3 C19 H19A . . 109.5 ?
O3 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O3 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C14 . 1.360(4) ?
O2 C18 . 1.417(4) ?
O3 C15 . 1.363(4) ?
O3 C19 . 1.407(5) ?
O1 C7 . 1.225(4) ?
C13 C14 . 1.385(4) ?
C13 C12 . 1.409(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.406(4) ?
C16 C15 . 1.378(5) ?
C16 C17 . 1.388(4) ?
C16 H16 . 0.9300 ?
C8 C11 . 1.340(4) ?
C8 C7 . 1.493(4) ?
C8 C9 . 1.502(4) ?
C17 C12 . 1.383(4) ?
C17 H17 . 0.9300 ?
C6 C5 . 1.397(4) ?
C6 C1 . 1.398(4) ?
C6 C7 . 1.485(4) ?
C12 C11 . 1.463(4) ?
C5 C4 . 1.397(4) ?
C5 C10 . 1.500(4) ?
C11 H11 . 0.9300 ?
C10 C9 . 1.523(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C1 C2 . 1.377(5) ?
C1 H1 . 0.9300 ?
C4 C3 . 1.381(5) ?
C4 H4 . 0.9300 ?
C2 C3 . 1.384(6) ?
C2 H2 . 0.9300 ?
C3 H3 . 0.9300 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 O3 2_665 0.93 2.52 3.385(4) 155 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C18 O2 C14 C13 . . . . 1.5(5) ?
C18 O2 C14 C15 . . . . -178.2(3) ?
C12 C13 C14 O2 . . . . -179.0(3) ?
C12 C13 C14 C15 . . . . 0.7(4) ?
C19 O3 C15 C16 . . . . -6.3(5) ?
C19 O3 C15 C14 . . . . 173.1(4) ?
C17 C16 C15 O3 . . . . -179.5(3) ?
C17 C16 C15 C14 . . . . 1.1(5) ?
O2 C14 C15 O3 . . . . -0.4(4) ?
C13 C14 C15 O3 . . . . 179.9(3) ?
O2 C14 C15 C16 . . . . 179.0(3) ?
C13 C14 C15 C16 . . . . -0.7(5) ?
C15 C16 C17 C12 . . . . -1.6(5) ?
C16 C17 C12 C13 . . . . 1.6(5) ?
C16 C17 C12 C11 . . . . 178.7(3) ?
C14 C13 C12 C17 . . . . -1.1(4) ?
C14 C13 C12 C11 . . . . -178.1(3) ?
C1 C6 C5 C4 . . . . -0.9(5) ?
C7 C6 C5 C4 . . . . 179.4(3) ?
C1 C6 C5 C10 . . . . 177.3(3) ?
C7 C6 C5 C10 . . . . -2.4(4) ?
C7 C8 C11 C12 . . . . 179.4(3) ?
C9 C8 C11 C12 . . . . -2.8(6) ?
C17 C12 C11 C8 . . . . 147.4(3) ?
C13 C12 C11 C8 . . . . -35.7(5) ?
C5 C6 C7 O1 . . . . 170.2(3) ?
C1 C6 C7 O1 . . . . -9.5(5) ?
C5 C6 C7 C8 . . . . -12.2(4) ?
C1 C6 C7 C8 . . . . 168.1(3) ?
C11 C8 C7 O1 . . . . -11.9(5) ?
C9 C8 C7 O1 . . . . 170.1(3) ?
C11 C8 C7 C6 . . . . 170.6(3) ?
C9 C8 C7 C6 . . . . -7.4(4) ?
C4 C5 C10 C9 . . . . -146.9(3) ?
C6 C5 C10 C9 . . . . 35.0(4) ?
C11 C8 C9 C10 . . . . -138.6(3) ?
C7 C8 C9 C10 . . . . 39.2(4) ?
C5 C10 C9 C8 . . . . -52.3(4) ?
C5 C6 C1 C2 . . . . 0.4(5) ?
C7 C6 C1 C2 . . . . -179.9(3) ?
C6 C5 C4 C3 . . . . 0.8(5) ?
C10 C5 C4 C3 . . . . -177.3(3) ?
C6 C1 C2 C3 . . . . 0.3(6) ?
C5 C4 C3 C2 . . . . -0.2(5) ?
C1 C2 C3 C4 . . . . -0.4(6) ?

_cod_database_fobs_code 1561313
