#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/24/2242429.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_2242429
loop_
_publ_author_name
'Ouédraogo, Mohammad'
'Abou, Akoun'
'Djandé, Abdoulaye'
'Ouari, Olivier'
'Zoueu, T. Jérémie'
_publ_section_title
;
 2-Oxo-2H-chromen-7-yl 4-tert-butylbenzoate
;
_journal_coeditor_code           SJ5549
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              530
_journal_page_last               534
_journal_paper_doi               10.1107/S2056989018004188
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C20 H18 O4'
_chemical_formula_moiety         'C20 H18 O4'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.34
_chemical_melting_point_gt       406
_chemical_melting_point_lt       408
_chemical_name_common            'Coumarin ester'
_chemical_name_systematic
;
2-Oxo-2H-chromen-7-yl 4-tert-butylbenzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.627(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.684(2)
_cell_length_b                   6.5431(5)
_cell_length_c                   13.6688(14)
_cell_measurement_reflns_used    1499
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      63.4210
_cell_measurement_theta_min      4.7300
_cell_volume                     1667.7(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek,2009) and Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015), publCIF (Westrip, 2010) and WinGX
(Farrugia,
2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2014 (Burla et al., 2015)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 5.3048
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9647
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.722
_diffrn_reflns_theta_min         4.743
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.71393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .04
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0569
_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)+(0.0981P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1610
_refine_ls_wR_factor_ref         0.2015
_reflns_number_gt                1710
_reflns_number_total             3005
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj5549sup1.cif
_cod_data_source_block           I
_cod_database_code               2242429
_cod_database_fobs_code          2242429
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O O3 0.05338(12) 0.1955(3) 0.65709(16) 0.0967(6) Uani d 1
O O1 -0.19810(13) 0.3433(3) 0.65369(16) 0.1016(7) Uani d 1
O O4 0.04152(14) 0.5177(3) 0.6031(2) 0.1233(9) Uani d 1
C C7 -0.01924(18) 0.1455(4) 0.64140(19) 0.0869(8) Uani d 1
C C4 -0.15790(19) 0.0068(4) 0.61057(19) 0.0905(8) Uani d 1
C C6 -0.07476(18) 0.2783(4) 0.6568(2) 0.0904(8) Uani d 1
H H6 -0.0662 0.4119 0.6776 0.108 Uiso calc 1
C C11 0.15865(18) 0.3838(4) 0.63538(19) 0.0860(8) Uani d 1
C C5 -0.14356(18) 0.2044(4) 0.63979(19) 0.0869(8) Uani d 1
C C9 -0.1001(2) -0.1235(4) 0.5982(2) 0.0974(9) Uani d 1
H H9 -0.1086 -0.2586 0.5797 0.117 Uiso calc 1
C C10 0.0789(2) 0.3799(4) 0.6300(2) 0.0907(8) Uani d 1
C C12 0.1920(2) 0.5629(4) 0.6107(2) 0.0974(9) Uani d 1
H H12 0.1645 0.6774 0.5935 0.117 Uiso calc 1
C C14 0.3083(2) 0.4064(5) 0.6350(2) 0.0971(9) Uani d 1
C C8 -0.0311(2) -0.0549(4) 0.6129(2) 0.0933(8) Uani d 1
H H8 0.0073 -0.1419 0.6038 0.112 Uiso calc 1
C C3 -0.2317(2) -0.0532(5) 0.5957(2) 0.1066(10) Uani d 1
H H3 -0.2432 -0.1866 0.5774 0.128 Uiso calc 1
O O2 -0.31255(16) 0.4209(5) 0.6509(2) 0.1421(11) Uani d 1
C C13 0.2657(2) 0.5738(5) 0.6111(2) 0.1024(10) Uani d 1
H H13 0.2872 0.6965 0.5950 0.123 Uiso calc 1
C C16 0.20033(19) 0.2163(4) 0.6614(2) 0.0957(9) Uani d 1
H H16 0.1788 0.0951 0.6794 0.115 Uiso calc 1
C C15 0.2743(2) 0.2284(5) 0.6607(2) 0.1034(10) Uani d 1
H H15 0.3018 0.1140 0.6781 0.124 Uiso calc 1
C C1 -0.2694(2) 0.2881(6) 0.6378(3) 0.1124(10) Uani d 1
C C2 -0.2839(2) 0.0826(6) 0.6080(3) 0.1137(11) Uani d 1
H H2 -0.3314 0.0415 0.5968 0.136 Uiso calc 1
C C17 0.3902(2) 0.4102(6) 0.6331(3) 0.1112(10) Uani d 1
C C18 0.4185(3) 0.6214(7) 0.6053(4) 0.1529(18) Uani d 1
H H18A 0.3973 0.6606 0.5423 0.229 Uiso calc 1
H H18B 0.4062 0.7200 0.6535 0.229 Uiso calc 1
H H18C 0.4697 0.6157 0.6028 0.229 Uiso calc 1
C C19 0.4251(3) 0.3551(9) 0.7329(4) 0.170(2) Uani d 1
H H19A 0.4763 0.3583 0.7302 0.256 Uiso calc 1
H H19B 0.4107 0.4518 0.7807 0.256 Uiso calc 1
H H19C 0.4103 0.2205 0.7508 0.256 Uiso calc 1
C C20 0.4126(3) 0.2572(8) 0.5546(4) 0.166(2) Uani d 1
H H20A 0.3901 0.2942 0.4920 0.249 Uiso calc 1
H H20B 0.4638 0.2604 0.5512 0.249 Uiso calc 1
H H20C 0.3979 0.1219 0.5717 0.249 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C10 O3 C7 121.3(2)
C1 O1 C5 121.1(3)
C6 C7 C8 122.2(3)
C6 C7 O3 124.1(3)
C8 C7 O3 113.7(3)
C5 C4 C9 118.2(3)
C5 C4 C3 117.8(3)
C9 C4 C3 124.0(3)
C5 C6 C7 117.1(3)
C5 C6 H6 121.5
C7 C6 H6 121.5
C16 C11 C12 118.8(3)
C16 C11 C10 123.2(3)
C12 C11 C10 118.0(3)
C4 C5 C6 122.8(3)
C4 C5 O1 121.6(3)
C6 C5 O1 115.6(2)
C8 C9 C4 120.8(3)
C8 C9 H9 119.6
C4 C9 H9 119.6
O4 C10 O3 123.5(3)
O4 C10 C11 124.8(3)
O3 C10 C11 111.7(2)
C11 C12 C13 120.6(3)
C11 C12 H12 119.7
C13 C12 H12 119.7
C13 C14 C15 117.4(4)
C13 C14 C17 123.0(3)
C15 C14 C17 119.6(3)
C9 C8 C7 119.0(3)
C9 C8 H8 120.5
C7 C8 H8 120.5
C2 C3 C4 120.1(3)
C2 C3 H3 119.9
C4 C3 H3 119.9
C12 C13 C14 121.4(3)
C12 C13 H13 119.3
C14 C13 H13 119.3
C11 C16 C15 120.1(3)
C11 C16 H16 120.0
C15 C16 H16 120.0
C14 C15 C16 121.7(3)
C14 C15 H15 119.2
C16 C15 H15 119.2
O2 C1 O1 115.8(3)
O2 C1 C2 127.2(4)
O1 C1 C2 117.0(4)
C3 C2 C1 122.3(4)
C3 C2 H2 118.8
C1 C2 H2 118.8
C19 C17 C14 110.7(3)
C19 C17 C18 107.5(4)
C14 C17 C18 112.2(3)
C19 C17 C20 110.6(4)
C14 C17 C20 108.4(3)
C18 C17 C20 107.3(4)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C10 1.357(3)
O3 C7 1.399(4)
O1 C1 1.383(4)
O1 C5 1.387(3)
O4 C10 1.184(3)
C7 C6 1.379(4)
C7 C8 1.382(4)
C4 C5 1.375(4)
C4 C9 1.395(5)
C4 C3 1.436(5)
C6 C5 1.379(4)
C6 H6 0.9300
C11 C16 1.378(4)
C11 C12 1.379(4)
C11 C10 1.488(5)
C9 C8 1.369(5)
C9 H9 0.9300
C12 C13 1.380(5)
C12 H12 0.9300
C14 C13 1.381(4)
C14 C15 1.383(4)
C14 C17 1.531(5)
C8 H8 0.9300
C3 C2 1.338(5)
C3 H3 0.9300
O2 C1 1.206(4)
C13 H13 0.9300
C16 C15 1.385(5)
C16 H16 0.9300
C15 H15 0.9300
C1 C2 1.426(5)
C2 H2 0.9300
C17 C19 1.517(5)
C17 C18 1.536(5)
C17 C20 1.545(5)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 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
C8 H8 O4 1_545 0.93 2.32 3.114(4) 143.5
C15 H15 O2 2_546 0.93 2.65 3.310(4) 128.1
C6 H6 O4 . 0.93 2.41 2.813(4) 105.8
C10 O4 Cg2 2_556 1.184(3) 3.760(3) 3.560(3) 71.23(18)
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
C10 O3 C7 C6 -41.5(4)
C10 O3 C7 C8 141.3(3)
C8 C7 C6 C5 -1.7(4)
O3 C7 C6 C5 -178.7(2)
C9 C4 C5 C6 0.3(4)
C3 C4 C5 C6 179.7(3)
C9 C4 C5 O1 180.0(2)
C3 C4 C5 O1 -0.6(4)
C7 C6 C5 C4 1.2(4)
C7 C6 C5 O1 -178.5(2)
C1 O1 C5 C4 -0.5(4)
C1 O1 C5 C6 179.2(3)
C5 C4 C9 C8 -1.3(4)
C3 C4 C9 C8 179.4(3)
C7 O3 C10 O4 9.6(4)
C7 O3 C10 C11 -168.7(2)
C16 C11 C10 O4 -175.9(3)
C12 C11 C10 O4 2.4(5)
C16 C11 C10 O3 2.3(4)
C12 C11 C10 O3 -179.4(2)
C16 C11 C12 C13 0.6(4)
C10 C11 C12 C13 -177.8(3)
C4 C9 C8 C7 0.7(4)
C6 C7 C8 C9 0.8(4)
O3 C7 C8 C9 178.1(3)
C5 C4 C3 C2 1.5(5)
C9 C4 C3 C2 -179.2(3)
C11 C12 C13 C14 0.8(5)
C15 C14 C13 C12 -1.5(5)
C17 C14 C13 C12 177.9(3)
C12 C11 C16 C15 -1.1(5)
C10 C11 C16 C15 177.2(3)
C13 C14 C15 C16 0.9(5)
C17 C14 C15 C16 -178.5(3)
C11 C16 C15 C14 0.4(5)
C5 O1 C1 O2 -179.1(3)
C5 O1 C1 C2 0.8(5)
C4 C3 C2 C1 -1.2(5)
O2 C1 C2 C3 180.0(4)
O1 C1 C2 C3 0.1(6)
C13 C14 C17 C19 122.1(4)
C15 C14 C17 C19 -58.5(5)
C13 C14 C17 C18 1.9(5)
C15 C14 C17 C18 -178.7(4)
C13 C14 C17 C20 -116.5(4)
C15 C14 C17 C20 62.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139088523
