#------------------------------------------------------------------------------
#$Date: 2022-02-26 05:16:06 +0200 (Sat, 26 Feb 2022) $
#$Revision: 273176 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/64/1566424.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_1566424
loop_
_publ_author_name
'Surya Prakash Rao, H.'
'M, Prabakaran'
'Muthukumaran, Jayaraman'
_publ_section_title
;
 Ethyl
 10-cyano-7-hydroxy-6-oxo-3-phenyl-8,9,10,10a-tetrahydro-6H-benzo[c]chromene-10-carboxylate
;
_journal_coeditor_code           HB4401
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x220199
_journal_paper_doi               10.1107/S2414314622001997
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C23 H19 N O5'
_chemical_formula_moiety         'C23 H19 N O5'
_chemical_formula_sum            'C23 H19 N O5'
_chemical_formula_weight         389.39
_chemical_name_systematic
'Ethyl 10-cyano-7-hydroxy-6-oxo-3-phenyl-8,9,10,10a-tetrahydro-6H-benzo[c]chromene-10-carboxylate'
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.946(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7089(8)
_cell_length_b                   14.3510(12)
_cell_length_c                   14.2749(15)
_cell_measurement_reflns_used    2883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1084
_cell_measurement_theta_min      2.9845
_cell_volume                     1902.6(3)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020) and
Mercury
(Macrae et al.,  2020)
;
_computing_publication_material
;
ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020) and
Mercury
(Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10689
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.173
_diffrn_reflns_theta_min         2.991
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysalisPro; Agilent, 2014)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1567
_reflns_number_gt                3119
_reflns_number_total             4413
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4401sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1566424
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.53859(10) 0.16733(8) 0.92065(7) 0.0410(3) Uani d 1 . .
O O2 0.63028(12) 0.27465(8) 0.84841(8) 0.0509(3) Uani d 1 . .
C C14 0.44382(14) 0.18379(10) 0.74486(11) 0.0347(3) Uani d 1 . .
O O5 0.27716(13) -0.06937(8) 0.61784(10) 0.0595(4) Uani d 1 . .
C C15 0.36436(14) 0.09212(10) 0.73953(10) 0.0332(3) Uani d 1 . .
H H15 0.431514 0.042889 0.734017 0.040 Uiso calc 1 . .
O O3 0.50815(13) 0.31695(9) 0.66833(9) 0.0588(4) Uani d 1 . .
H H3 0.561932 0.325224 0.723781 0.088 Uiso calc 1 . .
C C9 0.42029(14) 0.11197(10) 0.92053(11) 0.0337(3) Uani d 1 . .
C C10 0.32907(15) 0.07558(10) 0.83485(11) 0.0347(3) Uani d 1 . .
C C7 0.29134(15) 0.04148(11) 1.02203(11) 0.0366(4) Uani d 1 . .
C C4 0.27309(15) 0.02080(11) 1.11980(11) 0.0382(4) Uani d 1 . .
C C19 0.28311(17) 0.11903(13) 0.55664(11) 0.0447(4) Uani d 1 . .
H H19A 0.360887 0.079214 0.550748 0.054 Uiso calc 1 . .
H H19B 0.203779 0.112652 0.497179 0.054 Uiso calc 1 . .
C C16 0.11816(17) 0.14945(12) 0.65498(12) 0.0450(4) Uani d 1 . .
C C13 0.54193(15) 0.21194(11) 0.83729(11) 0.0375(4) Uani d 1 . .
C C20 0.23367(15) 0.08697(11) 0.64512(11) 0.0377(4) Uani d 1 . .
C C8 0.40422(15) 0.09584(10) 1.01183(11) 0.0366(4) Uani d 1 . .
H H8 0.469369 0.121527 1.066950 0.044 Uiso calc 1 . .
C C21 0.17320(17) -0.01170(12) 0.62229(11) 0.0437(4) Uani d 1 . .
O O4 0.05006(13) -0.03278(10) 0.60776(10) 0.0649(4) Uani d 1 . .
C C12 0.19570(17) 0.00624(12) 0.93635(12) 0.0443(4) Uani d 1 . .
H H12 0.117331 -0.029036 0.940506 0.053 Uiso calc 1 . .
C C18 0.33369(17) 0.21905(12) 0.56740(12) 0.0467(4) Uani d 1 . .
H H18A 0.381800 0.232559 0.518170 0.056 Uiso calc 1 . .
H H18B 0.250752 0.259856 0.555766 0.056 Uiso calc 1 . .
C C17 0.43402(16) 0.23902(11) 0.66616(12) 0.0410(4) Uani d 1 . .
C C11 0.21487(17) 0.02259(12) 0.84563(12) 0.0443(4) Uani d 1 . .
H H11 0.149569 -0.002549 0.790253 0.053 Uiso calc 1 . .
C C6 0.20395(18) -0.05906(13) 1.13558(13) 0.0507(4) Uani d 1 . .
H H6 0.166517 -0.099657 1.083600 0.061 Uiso calc 1 . .
C C3 0.32765(18) 0.08032(12) 1.19927(12) 0.0466(4) Uani d 1 . .
H H3A 0.375026 0.134713 1.191218 0.056 Uiso calc 1 . .
C C2 0.2424(2) -0.02057(16) 1.30377(15) 0.0627(5) Uani d 1 . .
H H2 0.231601 -0.034154 1.364935 0.075 Uiso calc 1 . .
C C1 0.1887(2) -0.08045(15) 1.22642(15) 0.0637(5) Uani d 1 . .
H H1 0.142442 -0.135050 1.235243 0.076 Uiso calc 1 . .
C C5 0.3116(2) 0.05875(15) 1.29030(14) 0.0579(5) Uani d 1 . .
H H5 0.348412 0.098916 1.342756 0.070 Uiso calc 1 . .
C C22 0.2376(2) -0.16616(14) 0.59282(18) 0.0714(6) Uani d 1 . .
H H22A 0.150569 -0.169084 0.538150 0.086 Uiso calc 1 . .
H H22B 0.220030 -0.197877 0.648226 0.086 Uiso calc 1 . .
C C23 0.3565(3) -0.21069(18) 0.5666(2) 0.1099(10) Uani d 1 . .
H H23A 0.372605 -0.179133 0.511451 0.165 Uiso calc 1 . .
H H23B 0.333040 -0.274743 0.550071 0.165 Uiso calc 1 . .
H H23C 0.442123 -0.207456 0.621170 0.165 Uiso calc 1 . .
N N1 0.03398(17) 0.20167(13) 0.66178(13) 0.0658(5) Uani d 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'
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'
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
C13 O1 C9 . . 119.76(11) ?
C17 C14 C13 . . 117.57(14) ?
C17 C14 C15 . . 123.65(13) ?
C13 C14 C15 . . 118.68(13) ?
C21 O5 C22 . . 117.30(14) ?
C14 C15 C10 . . 109.62(12) ?
C14 C15 C20 . . 111.00(12) ?
C10 C15 C20 . . 115.36(12) ?
C8 C9 C10 . . 123.53(14) ?
C8 C9 O1 . . 114.50(12) ?
C10 C9 O1 . . 121.96(13) ?
C9 C10 C11 . . 115.70(14) ?
C9 C10 C15 . . 118.66(13) ?
C11 C10 C15 . . 125.57(13) ?
C8 C7 C12 . . 117.11(14) ?
C8 C7 C4 . . 121.65(13) ?
C12 C7 C4 . . 121.25(14) ?
C6 C4 C3 . . 117.61(15) ?
C6 C4 C7 . . 121.05(15) ?
C3 C4 C7 . . 121.33(15) ?
C18 C19 C20 . . 111.65(14) ?
N1 C16 C20 . . 176.08(18) ?
O2 C13 O1 . . 115.36(13) ?
O2 C13 C14 . . 125.24(14) ?
O1 C13 C14 . . 119.40(13) ?
C16 C20 C21 . . 109.13(13) ?
C16 C20 C19 . . 108.83(12) ?
C21 C20 C19 . . 107.00(13) ?
C16 C20 C15 . . 109.78(13) ?
C21 C20 C15 . . 113.11(12) ?
C19 C20 C15 . . 108.88(12) ?
C9 C8 C7 . . 120.33(13) ?
O4 C21 O5 . . 125.08(16) ?
O4 C21 C20 . . 125.09(16) ?
O5 C21 C20 . . 109.79(13) ?
C11 C12 C7 . . 121.50(15) ?
C17 C18 C19 . . 112.50(13) ?
O3 C17 C14 . . 124.59(14) ?
O3 C17 C18 . . 112.66(13) ?
C14 C17 C18 . . 122.73(14) ?
C12 C11 C10 . . 121.79(14) ?
C4 C6 C1 . . 121.87(18) ?
C5 C3 C4 . . 120.32(17) ?
C5 C2 C1 . . 119.68(18) ?
C2 C1 C6 . . 119.68(19) ?
C2 C5 C3 . . 120.84(18) ?
O5 C22 C23 . . 107.97(17) ?
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
O1 C13 . 1.3599(18) ?
O1 C9 . 1.3961(17) ?
O2 C13 . 1.2212(18) ?
C14 C17 . 1.355(2) ?
C14 C13 . 1.442(2) ?
C14 C15 . 1.516(2) ?
O5 C21 . 1.321(2) ?
O5 C22 . 1.457(2) ?
C15 C10 . 1.516(2) ?
C15 C20 . 1.5604(19) ?
O3 C17 . 1.3255(19) ?
C9 C8 . 1.377(2) ?
C9 C10 . 1.386(2) ?
C10 C11 . 1.390(2) ?
C7 C8 . 1.387(2) ?
C7 C12 . 1.397(2) ?
C7 C4 . 1.487(2) ?
C4 C6 . 1.379(2) ?
C4 C3 . 1.395(2) ?
C19 C18 . 1.510(2) ?
C19 C20 . 1.546(2) ?
C16 N1 . 1.134(2) ?
C16 C20 . 1.474(2) ?
C20 C21 . 1.531(2) ?
C21 O4 . 1.1913(18) ?
C12 C11 . 1.381(2) ?
C18 C17 . 1.489(2) ?
C6 C1 . 1.382(2) ?
C3 C5 . 1.388(2) ?
C2 C5 . 1.363(3) ?
C2 C1 . 1.376(3) ?
C22 C23 . 1.460(3) ?
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
O3 H3 O2 . 0.82 1.86 2.5702(16) 145 yes
C11 H11 O4 . 0.93 2.54 3.399(2) 154 yes
C18 H18B O1 4_565 0.97 2.60 3.4289(19) 144 yes
C19 H19B O2 4_565 0.97 2.60 3.285(2) 128 yes
C15 H15 Cg2 3_657 0.98 2.95 3.7685(17) 142 yes
C23 H23B Cg3 2_546 0.96 2.82 3.686(3) 151 yes

_cod_database_fobs_code 1566424
