##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_journal_date_recd_electronic     2021-02-18
_journal_date_accepted     2021-02-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2021
_journal_volume     77
_journal_issue      4
_journal_page_first     331
_journal_page_last     334
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989021002218
_journal_coeditor_code     WM5600
_publ_contact_author_name     'Ulrich Lüning'
_publ_contact_author_address
;
Otto-Diels-Institut für Organische Chemie
Christian-Albrechts-Universität zu Kiel
Otto-Hahn-Platz 4
D-24098 Kiel
Germany
;
_publ_contact_author_email     luening@oc.uni-kiel.de
_publ_contact_author_fax     +431-880-1558
_publ_contact_author_phone     +431-880-2440
_publ_section_title
;
Synthesis and crystal structure of allyl
7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Vanessa Nowatschin' .
;
Otto-Diels-Institut für Organische Chemie
Christian-Albrechts-Universität zu Kiel
Otto-Hahn-Platz 4
D-24098 Kiel
Germany
;
    'Näther, Christian' .
;
Institut für Anorganische Chemie
Christian-Albrechts-Universität zu Kiel
Max-Eyth Str. 2
D-24118 Kiel
Germany
;
    'Lüning, Ulrich' .
;
Otto-Diels-Institut für Organische Chemie
Christian-Albrechts-Universität zu Kiel
Otto-Hahn-Platz 4
D-24098 Kiel
Germany
;
_publ_section_synopsis
;
The crystal structure of the title compound, C₁₇H₁₉NO₄, consists of
nearly planar molecules that are linked by intermolecular C---H...O hydrogen
bonding into chains along the b-axis direction.
;
_chemical_name_systematic
;
Allyl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate
;
_chemical_name_common
;
Allyl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate
;
_chemical_formula_moiety     'C17 H19 N O4'
_chemical_formula_sum     'C17 H19 N O4'
_chemical_formula_iupac     'C17 H19 N O4'
_chemical_formula_weight     301.33
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/c 1'
_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     13.72487(9)
_cell_length_b     13.05333(9)
_cell_length_c     8.55970(6)
_cell_angle_alpha     90
_cell_angle_beta     95.5220(6)
_cell_angle_gamma     90
_cell_volume     1526.399(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     18730
_cell_measurement_theta_min     3.2190
_cell_measurement_theta_max     79.4630
_cell_measurement_temperature     99.99(10)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.08
_exptl_crystal_size_mid     0.06
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.311
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     0.768
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_absorpt_correction_T_min     0.79615
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     99.99(10)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean     10.0000
_diffrn_reflns_number     26198
_diffrn_reflns_av_R_equivalents     0.0245
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_theta_min     3.235
_diffrn_reflns_theta_max     74.459
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     9
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     3125
_reflns_number_gt     2975
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0345
_refine_ls_R_factor_gt     0.0332
_refine_ls_wR_factor_gt     0.0887
_refine_ls_wR_factor_ref     0.0898
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     3125
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0452P)²+0.4857P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.271
_refine_diff_density_min     -0.176
_refine_ls_extinction_method
;
SHELXL (Sheldrick, 2015b)
;
_refine_ls_extinction_coef     0.00051(13)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'N' 'N' 0.0311 0.0180
                         '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'
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009) and DIAMOND (Brandenburg,
2014)
;
_computing_publication_material
;
publcif (Westrip, 2010)
;
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 0.42522(5) 0.43406(5) 0.62496(8) 0.02005(16) Uani d 1 . .
    O O2 0.30849(5) 0.49523(5) 0.45723(9) 0.02685(18) Uani d 1 . .
    O O3 0.14546(5) 0.22199(6) 0.48871(10) 0.03164(19) Uani d 1 . .
    O O4 0.15018(5) 0.37908(6) 0.38321(9) 0.02571(18) Uani d 1 . .
    N N1 0.69931(6) 0.32538(6) 0.96569(9) 0.02028(19) Uani d 1 . .
    C C1 0.33583(7) 0.42197(7) 0.53540(11) 0.0200(2) Uani d 1 . .
    C C2 0.28755(7) 0.32340(7) 0.54870(11) 0.0200(2) Uani d 1 . .
    C C3 0.33465(7) 0.24639(7) 0.63486(11) 0.0208(2) Uani d 1 . .
    H H3 0.302995 0.181966 0.640621 0.025 Uiso calc 1 . .
    C C4 0.42814(7) 0.25947(7) 0.71496(11) 0.0196(2) Uani d 1 . .
    C C5 0.48286(7) 0.18288(7) 0.80087(11) 0.0213(2) Uani d 1 . .
    H H5 0.457233 0.115320 0.802308 0.026 Uiso calc 1 . .
    C C6 0.57144(7) 0.20301(7) 0.88188(11) 0.0208(2) Uani d 1 . .
    H H6 0.606652 0.149382 0.937029 0.025 Uiso calc 1 . .
    C C7 0.61162(7) 0.30412(7) 0.88437(11) 0.0187(2) Uani d 1 . .
    C C8 0.55922(7) 0.38049(7) 0.79458(11) 0.0194(2) Uani d 1 . .
    H H8 0.584776 0.448004 0.791190 0.023 Uiso calc 1 . .
    C C9 0.47128(7) 0.35691(7) 0.71221(11) 0.0184(2) Uani d 1 . .
    C C10 0.18826(7) 0.30202(8) 0.47158(11) 0.0220(2) Uani d 1 . .
    C C11 0.05028(7) 0.36342(9) 0.31361(13) 0.0278(2) Uani d 1 . .
    H H11A 0.005740 0.353447 0.396689 0.033 Uiso calc 1 . .
    H H11B 0.046669 0.302041 0.245361 0.033 Uiso calc 1 . .
    C C12 0.02189(8) 0.45623(9) 0.22007(14) 0.0333(3) Uani d 1 . .
    H H12 0.056563 0.471426 0.132052 0.040 Uiso calc 1 . .
    C C13 -0.04888(9) 0.51877(10) 0.25251(17) 0.0408(3) Uani d 1 . .
    H H13A -0.084753 0.505412 0.339854 0.049 Uiso calc 1 . .
    H H13B -0.064001 0.577191 0.188542 0.049 Uiso calc 1 . .
    C C14 0.74215(7) 0.42822(8) 0.96559(12) 0.0237(2) Uani d 1 . .
    H H14A 0.730319 0.457818 0.858963 0.028 Uiso calc 1 . .
    H H14B 0.813825 0.423083 0.991818 0.028 Uiso calc 1 . .
    C C15 0.69959(9) 0.49949(8) 1.08247(13) 0.0303(2) Uani d 1 . .
    H H15A 0.630056 0.511206 1.049963 0.045 Uiso calc 1 . .
    H H15B 0.734605 0.564996 1.085692 0.045 Uiso calc 1 . .
    H H15C 0.706714 0.468117 1.186964 0.045 Uiso calc 1 . .
    C C16 0.74742(7) 0.25546(8) 1.08276(11) 0.0231(2) Uani d 1 . .
    H H16A 0.699758 0.202771 1.109081 0.028 Uiso calc 1 . .
    H H16B 0.767645 0.294469 1.179671 0.028 Uiso calc 1 . .
    C C17 0.83648(8) 0.20262(9) 1.02778(14) 0.0324(3) Uani d 1 . .
    H H17A 0.816019 0.157826 0.938740 0.049 Uiso calc 1 . .
    H H17B 0.868653 0.161646 1.113786 0.049 Uiso calc 1 . .
    H H17C 0.882291 0.254245 0.995308 0.049 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 . 1.3916(11) ?
    O1 C9 . 1.3714(11) ?
    O2 C1 . 1.2062(12) ?
    O3 C10 . 1.2142(13) ?
    O4 C10 . 1.3346(12) ?
    O4 C11 . 1.4558(11) ?
    N1 C7 . 1.3597(12) ?
    N1 C14 . 1.4655(13) ?
    N1 C16 . 1.4648(12) ?
    C1 C2 . 1.4567(13) ?
    C2 C3 . 1.3713(14) ?
    C2 C10 . 1.4824(13) ?
    C3 H3 . 0.9500 ?
    C3 C4 . 1.4059(13) ?
    C4 C5 . 1.4134(13) ?
    C4 C9 . 1.4041(13) ?
    C5 H5 . 0.9500 ?
    C5 C6 . 1.3660(14) ?
    C6 H6 . 0.9500 ?
    C6 C7 . 1.4297(14) ?
    C7 C8 . 1.4125(13) ?
    C8 H8 . 0.9500 ?
    C8 C9 . 1.3729(13) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C11 C12 . 1.4833(15) ?
    C12 H12 . 0.9500 ?
    C12 C13 . 1.3188(19) ?
    C13 H13A . 0.9500 ?
    C13 H13B . 0.9500 ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C14 C15 . 1.5233(15) ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C16 C17 . 1.5173(14) ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
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
    C9 O1 C1 . . 123.53(8) ?
    C10 O4 C11 . . 115.36(8) ?
    C7 N1 C14 . . 121.47(8) ?
    C7 N1 C16 . . 122.79(8) ?
    C16 N1 C14 . . 114.62(8) ?
    O1 C1 C2 . . 116.15(8) ?
    O2 C1 O1 . . 115.24(8) ?
    O2 C1 C2 . . 128.61(9) ?
    C1 C2 C10 . . 122.49(9) ?
    C3 C2 C1 . . 119.67(9) ?
    C3 C2 C10 . . 117.84(9) ?
    C2 C3 H3 . . 118.9 ?
    C2 C3 C4 . . 122.29(9) ?
    C4 C3 H3 . . 118.9 ?
    C3 C4 C5 . . 125.60(9) ?
    C9 C4 C3 . . 117.93(9) ?
    C9 C4 C5 . . 116.46(9) ?
    C4 C5 H5 . . 119.0 ?
    C6 C5 C4 . . 122.04(9) ?
    C6 C5 H5 . . 119.0 ?
    C5 C6 H6 . . 119.7 ?
    C5 C6 C7 . . 120.55(9) ?
    C7 C6 H6 . . 119.7 ?
    N1 C7 C6 . . 121.14(9) ?
    N1 C7 C8 . . 120.91(9) ?
    C8 C7 C6 . . 117.90(9) ?
    C7 C8 H8 . . 120.1 ?
    C9 C8 C7 . . 119.84(9) ?
    C9 C8 H8 . . 120.1 ?
    O1 C9 C4 . . 120.09(8) ?
    O1 C9 C8 . . 116.83(8) ?
    C8 C9 C4 . . 123.08(9) ?
    O3 C10 O4 . . 123.31(9) ?
    O3 C10 C2 . . 122.88(9) ?
    O4 C10 C2 . . 113.80(8) ?
    O4 C11 H11A . . 110.3 ?
    O4 C11 H11B . . 110.3 ?
    O4 C11 C12 . . 107.12(8) ?
    H11A C11 H11B . . 108.5 ?
    C12 C11 H11A . . 110.3 ?
    C12 C11 H11B . . 110.3 ?
    C11 C12 H12 . . 118.2 ?
    C13 C12 C11 . . 123.54(12) ?
    C13 C12 H12 . . 118.2 ?
    C12 C13 H13A . . 120.0 ?
    C12 C13 H13B . . 120.0 ?
    H13A C13 H13B . . 120.0 ?
    N1 C14 H14A . . 109.1 ?
    N1 C14 H14B . . 109.1 ?
    N1 C14 C15 . . 112.32(8) ?
    H14A C14 H14B . . 107.9 ?
    C15 C14 H14A . . 109.1 ?
    C15 C14 H14B . . 109.1 ?
    C14 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    C14 C15 H15C . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    N1 C16 H16A . . 108.9 ?
    N1 C16 H16B . . 108.9 ?
    N1 C16 C17 . . 113.25(8) ?
    H16A C16 H16B . . 107.7 ?
    C17 C16 H16A . . 108.9 ?
    C17 C16 H16B . . 108.9 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
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
    O1 C1 C2 C3 . . . . -5.62(13) ?
    O1 C1 C2 C10 . . . . 174.60(8) ?
    O2 C1 C2 C3 . . . . 174.72(10) ?
    O2 C1 C2 C10 . . . . -5.06(16) ?
    O4 C11 C12 C13 . . . . -115.91(12) ?
    N1 C7 C8 C9 . . . . 179.35(8) ?
    C1 O1 C9 C4 . . . . -0.28(13) ?
    C1 O1 C9 C8 . . . . 180.00(8) ?
    C1 C2 C3 C4 . . . . 1.44(14) ?
    C1 C2 C10 O3 . . . . -176.05(10) ?
    C1 C2 C10 O4 . . . . 3.33(13) ?
    C2 C3 C4 C5 . . . . -177.39(9) ?
    C2 C3 C4 C9 . . . . 3.51(14) ?
    C3 C2 C10 O3 . . . . 4.17(15) ?
    C3 C2 C10 O4 . . . . -176.45(8) ?
    C3 C4 C5 C6 . . . . -176.79(9) ?
    C3 C4 C9 O1 . . . . -4.15(13) ?
    C3 C4 C9 C8 . . . . 175.56(9) ?
    C4 C5 C6 C7 . . . . 0.96(14) ?
    C5 C4 C9 O1 . . . . 176.67(8) ?
    C5 C4 C9 C8 . . . . -3.62(14) ?
    C5 C6 C7 N1 . . . . 179.41(8) ?
    C5 C6 C7 C8 . . . . -3.06(14) ?
    C6 C7 C8 C9 . . . . 1.82(13) ?
    C7 N1 C14 C15 . . . . 81.70(11) ?
    C7 N1 C16 C17 . . . . 107.68(11) ?
    C7 C8 C9 O1 . . . . -178.72(8) ?
    C7 C8 C9 C4 . . . . 1.57(14) ?
    C9 O1 C1 O2 . . . . -175.17(8) ?
    C9 O1 C1 C2 . . . . 5.12(13) ?
    C9 C4 C5 C6 . . . . 2.31(14) ?
    C10 O4 C11 C12 . . . . -179.62(9) ?
    C10 C2 C3 C4 . . . . -178.77(9) ?
    C11 O4 C10 O3 . . . . 3.12(14) ?
    C11 O4 C10 C2 . . . . -176.26(8) ?
    C14 N1 C7 C6 . . . . 178.43(8) ?
    C14 N1 C7 C8 . . . . 0.97(13) ?
    C14 N1 C16 C17 . . . . -84.26(11) ?
    C16 N1 C7 C6 . . . . -14.31(13) ?
    C16 N1 C7 C8 . . . . 168.23(8) ?
    C16 N1 C14 C15 . . . . -86.53(10) ?
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
    C6 H6 O2 2_646 0.95 2.45 3.3958(12) 171.2
_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     ?
_shelx_estimated_absorpt_T_max     ?
