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#$Date: 2022-11-08 10:47:51 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106002.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_8106002
loop_
_publ_author_name
'Yu, Xiang'
'Peng, Lu'
'Wang, Xin'
'Chen, Ya-Fang'
_publ_section_title
;
 The crystal structure of
 (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl
 4-nitrobenzoate, C22H19NO7
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1269
_journal_page_last               1270
_journal_paper_doi               10.1515/ncrs-2019-0393
_journal_volume                  234
_journal_year                    2019
_chemical_formula_sum            'C22 H19 N O7'
_chemical_formula_weight         409.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 102.469(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5742(4)
_cell_length_b                   20.0688(12)
_cell_length_c                   13.2932(8)
_cell_measurement_reflns_used    2600
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      3.03
_cell_volume                     1973.0(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.814
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            81658
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         30.447
_diffrn_reflns_theta_min         3.035
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0726
_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)+(0.0518P)²+2.2885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1757
_refine_ls_wR_factor_ref         0.1777
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4438
_reflns_number_total             4882
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0393_suppl.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106002
_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   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 O 0.4098(2) 0.52727(7) 0.14215(12) 0.0408(4) Uani 1 1 d . . . . .
O2 O 0.2582(4) 0.61446(10) 0.1701(2) 0.0798(8) Uani 1 1 d . . . . .
O3 O 0.7009(3) 0.33155(8) 0.09057(14) 0.0508(5) Uani 1 1 d . . . . .
O4 O 0.3060(3) 0.40041(7) 0.39397(12) 0.0456(4) Uani 1 1 d . . . . .
O5 O 0.2941(4) 0.36713(9) 0.54588(15) 0.0724(7) Uani 1 1 d . . . . .
O6 O 0.1127(4) 0.69025(11) 0.64593(18) 0.0723(7) Uani 1 1 d . . . . .
O7 O 0.1919(4) 0.72439(10) 0.51883(19) 0.0852(8) Uani 1 1 d . . . . .
C1 C 0.4019(4) 0.59461(12) 0.1605(2) 0.0531(7) Uani 1 1 d . . . . .
C2 C 0.5651(5) 0.63380(12) 0.1665(2) 0.0548(7) Uani 1 1 d . . . . .
H2 H 0.561481 0.680510 0.177448 0.066 Uiso 1 1 calc R U . . .
C3 C 0.7177(4) 0.60586(11) 0.15708(18) 0.0473(6) Uani 1 1 d . . . . .
H3 H 0.822942 0.632428 0.161574 0.057 Uiso 1 1 calc R U . . .
C4 C 0.7261(3) 0.53550(11) 0.14006(15) 0.0372(5) Uani 1 1 d . . . . .
C5 C 0.5664(3) 0.49769(10) 0.13170(14) 0.0325(4) Uani 1 1 d . . . . .
C6 C 0.5556(3) 0.42938(10) 0.11403(14) 0.0323(4) Uani 1 1 d . . . . .
C7 C 0.7157(3) 0.39850(11) 0.10620(16) 0.0387(5) Uani 1 1 d . . . . .
C8 C 0.8773(4) 0.43488(13) 0.11383(19) 0.0468(6) Uani 1 1 d . . . . .
H8 H 0.984683 0.412436 0.107268 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8810(4) 0.50263(13) 0.13070(18) 0.0454(6) Uani 1 1 d . . . . .
H9 H 0.990646 0.526664 0.135871 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3823(3) 0.39017(10) 0.10885(16) 0.0361(5) Uani 1 1 d . . . . .
H10A H 0.278203 0.413712 0.065603 0.043 Uiso 1 1 calc R U . . .
H10B H 0.391997 0.345370 0.079326 0.043 Uiso 1 1 calc R U . . .
N24 N 0.1610(4) 0.68028(11) 0.57146(18) 0.0544(6) Uani 1 1 d . . . . .
C11 C 0.3605(3) 0.38504(10) 0.21286(16) 0.0345(5) Uani 1 1 d . . . . .
H11 H 0.339298 0.425397 0.245694 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3667(3) 0.33028(10) 0.26756(17) 0.0372(5) Uani 1 1 d . . . . .
C13 C 0.3363(4) 0.33230(10) 0.36947(18) 0.0433(6) Uani 1 1 d . . . . .
H13A H 0.442671 0.314362 0.418741 0.052 Uiso 1 1 calc R U . . .
H13B H 0.229628 0.304863 0.373963 0.052 Uiso 1 1 calc R U . . .
C14 C 0.2878(4) 0.41052(11) 0.48531(17) 0.0420(5) Uani 1 1 d . . . . .
C15 C 0.2557(3) 0.48194(10) 0.50344(16) 0.0376(5) Uani 1 1 d . . . . .
C16 C 0.2482(4) 0.53175(11) 0.43182(17) 0.0444(6) Uani 1 1 d . . . . .
H16 H 0.265159 0.520655 0.365067 0.053 Uiso 1 1 calc R U . . .
C17 C 0.2170(4) 0.59728(12) 0.45350(19) 0.0486(6) Uani 1 1 d . . . . .
H17 H 0.213701 0.631362 0.403531 0.058 Uiso 1 1 calc R U . . .
C18 C 0.1919(4) 0.61069(11) 0.54623(18) 0.0427(5) Uani 1 1 d . . . . .
C19 C 0.1954(4) 0.56236(12) 0.61747(17) 0.0436(5) Uani 1 1 d . . . . .
H19 H 0.173727 0.573471 0.683208 0.052 Uiso 1 1 calc R U . . .
C20 C 0.2301(4) 0.49730(11) 0.59580(16) 0.0413(5) Uani 1 1 d . . . . .
H20 H 0.235570 0.463722 0.646759 0.050 Uiso 1 1 calc R U . . .
C21 C 0.8637(5) 0.29654(15) 0.0870(3) 0.0720(9) Uani 1 1 d . . . . .
H21A H 0.838290 0.248706 0.079513 0.108 Uiso 1 1 calc R U . . .
H21B H 0.953517 0.304555 0.150910 0.108 Uiso 1 1 calc R U . . .
H21C H 0.910931 0.312353 0.028227 0.108 Uiso 1 1 calc R U . . .
C22 C 0.4016(5) 0.26075(11) 0.2372(2) 0.0561(8) Uani 1 1 d . . . . .
H22A H 0.449909 0.261638 0.174519 0.084 Uiso 1 1 calc R U . . .
H22B H 0.288367 0.235402 0.224268 0.084 Uiso 1 1 calc R U . . .
H22C H 0.489530 0.239526 0.292940 0.084 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'
O O 0.0106 0.0060 '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'
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
C5 O1 C1 121.3(2) . .
C7 O3 C21 116.6(2) . .
C14 O4 C13 115.20(17) . .
O2 C1 O1 115.0(3) . .
O2 C1 C2 126.8(2) . .
O1 C1 C2 118.2(2) . .
C3 C2 C1 121.3(2) . .
C3 C2 H2 119.4 . .
C1 C2 H2 119.4 . .
C2 C3 C4 120.3(2) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C9 C4 C5 117.9(2) . .
C9 C4 C3 123.7(2) . .
C5 C4 C3 118.4(2) . .
O1 C5 C6 115.29(19) . .
O1 C5 C4 120.57(18) . .
C6 C5 C4 124.1(2) . .
C7 C6 C5 115.7(2) . .
C7 C6 C10 121.76(18) . .
C5 C6 C10 122.5(2) . .
O3 C7 C6 114.1(2) . .
O3 C7 C8 124.3(2) . .
C6 C7 C8 121.6(2) . .
C9 C8 C7 120.6(2) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C4 C9 C8 120.0(2) . .
C4 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C11 C10 C6 105.81(17) . .
C11 C10 H10A 110.6 . .
C6 C10 H10A 110.6 . .
C11 C10 H10B 110.6 . .
C6 C10 H10B 110.6 . .
H10A C10 H10B 108.7 . .
O6 N24 O7 121.5(2) . .
O6 N24 C18 117.4(2) . .
O7 N24 C18 121.1(2) . .
C12 C11 C10 126.69(19) . .
C12 C11 H11 116.7 . .
C10 C11 H11 116.7 . .
C11 C12 C13 120.64(19) . .
C11 C12 C22 128.35(19) . .
C13 C12 C22 111.02(18) . .
C12 C13 O4 108.05(17) . .
C12 C13 H13A 110.1 . .
O4 C13 H13A 110.1 . .
C12 C13 H13B 110.1 . .
O4 C13 H13B 110.1 . .
H13A C13 H13B 108.4 . .
O5 C14 O4 122.6(2) . .
O5 C14 C15 125.9(2) . .
O4 C14 C15 111.48(18) . .
C20 C15 C16 118.8(2) . .
C20 C15 C14 116.04(19) . .
C16 C15 C14 125.10(19) . .
C15 C16 C17 122.2(2) . .
C15 C16 H16 118.9 . .
C17 C16 H16 118.9 . .
C18 C17 C16 117.2(2) . .
C18 C17 H17 121.4 . .
C16 C17 H17 121.4 . .
C17 C18 C19 121.7(2) . .
C17 C18 N24 118.1(2) . .
C19 C18 N24 120.2(2) . .
C18 C19 C20 120.7(2) . .
C18 C19 H19 119.6 . .
C20 C19 H19 119.6 . .
C15 C20 C19 119.3(2) . .
C15 C20 H20 120.3 . .
C19 C20 H20 120.3 . .
O3 C21 H21A 109.5 . .
O3 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
O3 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C12 C22 H22A 109.5 . .
C12 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C12 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.360(3) .
O1 C1 1.377(3) .
O2 C1 1.191(4) .
O3 C7 1.360(3) .
O3 C21 1.428(4) .
O4 C14 1.268(2) .
O4 C13 1.435(2) .
O5 C14 1.180(3) .
O6 N24 1.145(3) .
O7 N24 1.182(3) .
C1 C2 1.453(4) .
C2 C3 1.315(4) .
C2 H2 0.9500 .
C3 C4 1.434(3) .
C3 H3 0.9500 .
C4 C9 1.375(4) .
C4 C5 1.412(3) .
C5 C6 1.390(3) .
C6 C7 1.385(3) .
C6 C10 1.519(3) .
C7 C8 1.410(3) .
C8 C9 1.377(4) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C11 1.431(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
N24 C18 1.467(3) .
C11 C12 1.313(3) .
C11 H11 0.9500 .
C12 C13 1.423(3) .
C12 C22 1.492(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.482(3) .
C15 C20 1.320(3) .
C15 C16 1.373(3) .
C16 C17 1.378(3) .
C16 H16 0.9500 .
C17 C18 1.315(3) .
C17 H17 0.9500 .
C18 C19 1.352(3) .
C19 C20 1.375(3) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
