#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/06/2230615.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_2230615
loop_
_publ_author_name
'Li, Hong-Da'
'Yin, Bing-Zhu'
_publ_section_title
;
 7-Diethylamino-2-oxo-2H-chromene-3-carbaldehyde
;
_journal_coeditor_code           DN2698
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1713
_journal_paper_doi               10.1107/S160053681102294X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H15 N O3'
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_chemical_name_systematic
;
7-Diethylamino-2-oxo-2H-chromene-3-carbaldehyde
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 92.39(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.488(17)
_cell_length_b                   7.844(6)
_cell_length_c                   12.599(12)
_cell_measurement_reflns_used    6542
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.15
_cell_volume                     2517(4)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2002)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11514
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.3544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                1724
_reflns_number_total             2850
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2698.cif
_cod_data_source_block           I
_cod_original_cell_volume        2517(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2230615
_cod_database_fobs_code          2230615
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.24299(4) 0.00447(14) 0.88750(8) 0.0556(3) Uani d . 1 1 . .
O O2 0.17217(5) -0.12688(18) 0.82505(10) 0.0787(4) Uani d . 1 1 . .
O O3 0.12022(6) -0.24463(18) 1.11710(12) 0.0874(5) Uani d . 1 1 . .
N N1 0.40226(6) 0.2780(2) 0.99586(12) 0.0747(5) Uani d . 1 1 . .
C C1 0.19772(6) -0.0872(2) 0.90386(13) 0.0562(4) Uani d D 1 1 . .
C C2 0.18575(6) -0.12332(19) 1.01323(12) 0.0533(4) Uani d D 1 1 . .
C C3 0.21890(6) -0.0707(2) 1.09396(12) 0.0546(4) Uani d . 1 1 . .
H H3 0.2105 -0.0940 1.1636 0.066 Uiso calc R 1 1 . .
C C4 0.26540(6) 0.01794(19) 1.07523(11) 0.0503(4) Uani d . 1 1 . .
C C5 0.27674(6) 0.05510(19) 0.96975(11) 0.0478(4) Uani d . 1 1 A .
C C6 0.32073(6) 0.1413(2) 0.94200(12) 0.0533(4) Uani d . 1 1 . .
H H6 0.3261 0.1652 0.8710 0.064 Uiso calc R 1 1 A .
C C7 0.35790(6) 0.1938(2) 1.02108(13) 0.0578(4) Uani d . 1 1 A .
C C8 0.34695(7) 0.1572(2) 1.12853(13) 0.0636(5) Uani d . 1 1 . .
H H8 0.3707 0.1906 1.1826 0.076 Uiso calc R 1 1 A .
C C9 0.30257(7) 0.0747(2) 1.15318(12) 0.0613(4) Uani d . 1 1 A .
H H9 0.2963 0.0546 1.2243 0.074 Uiso calc R 1 1 . .
C C10 0.13764(7) -0.2172(2) 1.03121(16) 0.0679(5) Uani d . 1 1 . .
H H10 0.1189 -0.2592 0.9719 0.081 Uiso calc R 1 1 . .
C C11A 0.4515(3) 0.2676(10) 1.0761(7) 0.086(2) Uani d PD 0.46 1 A 1
H H11A 0.4478 0.1756 1.1267 0.103 Uiso calc PR 0.46 1 A 1
H H11B 0.4836 0.2509 1.0387 0.103 Uiso calc PR 0.46 1 A 1
C C12A 0.4513(2) 0.4378(8) 1.1303(5) 0.1030(17) Uani d PD 0.46 1 A 1
H H12A 0.4539 0.5266 1.0784 0.154 Uiso calc PR 0.46 1 A 1
H H12B 0.4807 0.4448 1.1805 0.154 Uiso calc PR 0.46 1 A 1
H H12C 0.4193 0.4510 1.1669 0.154 Uiso calc PR 0.46 1 A 1
C C11B 0.4390(2) 0.3468(8) 1.0753(5) 0.0750(15) Uani d P 0.54 1 A 2
H H11C 0.4204 0.3835 1.1370 0.090 Uiso calc PR 0.54 1 A 2
H H11D 0.4570 0.4445 1.0469 0.090 Uiso calc PR 0.54 1 A 2
C C12B 0.4784(2) 0.2088(8) 1.1068(5) 0.125(2) Uani d P 0.54 1 A 2
H H12D 0.4602 0.1130 1.1354 0.188 Uiso calc PR 0.54 1 A 2
H H12E 0.5031 0.2527 1.1595 0.188 Uiso calc PR 0.54 1 A 2
H H12F 0.4966 0.1734 1.0455 0.188 Uiso calc PR 0.54 1 A 2
C C13 0.41299(8) 0.3169(3) 0.88577(15) 0.0742(5) Uani d . 1 1 A .
H H13A 0.4374 0.4116 0.8847 0.089 Uiso calc R 1 1 . .
H H13B 0.3806 0.3533 0.8495 0.089 Uiso calc R 1 1 . .
C C14 0.43552(9) 0.1696(3) 0.8251(2) 0.1025(8) Uani d . 1 1 . .
H H14A 0.4692 0.1394 0.8563 0.154 Uiso calc R 1 1 A .
H H14B 0.4393 0.2024 0.7524 0.154 Uiso calc R 1 1 . .
H H14C 0.4123 0.0735 0.8280 0.154 Uiso calc R 1 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
C5 O1 C1 . . 122.47(12) ?
C7 N1 C11B . . 122.7(3) ?
C7 N1 C13 . . 121.03(15) ?
C11B N1 C13 . . 116.1(3) ?
C7 N1 C11A . . 118.2(3) ?
C13 N1 C11A . . 116.3(3) ?
O2 C1 O1 . . 115.93(15) ?
O2 C1 C2 . . 127.14(17) ?
O1 C1 C2 . . 116.93(14) ?
C3 C2 C1 . . 120.15(16) ?
C3 C2 C10 . . 122.59(16) ?
C1 C2 C10 . . 117.26(16) ?
C2 C3 C4 . . 121.88(14) ?
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
C3 C4 C5 . . 118.13(14) ?
C3 C4 C9 . . 126.03(14) ?
C5 C4 C9 . . 115.84(15) ?
C6 C5 O1 . . 116.32(13) ?
C6 C5 C4 . . 123.28(14) ?
O1 C5 C4 . . 120.40(15) ?
C5 C6 C7 . . 119.92(15) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
N1 C7 C6 . . 121.26(15) ?
N1 C7 C8 . . 121.26(16) ?
C6 C7 C8 . . 117.48(16) ?
C9 C8 C7 . . 120.99(16) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C4 . . 122.47(15) ?
C8 C9 H9 . . 118.8 ?
C4 C9 H9 . . 118.8 ?
O3 C10 C2 . . 125.00(19) ?
O3 C10 H10 . . 117.5 ?
C2 C10 H10 . . 117.5 ?
C12A C11A N1 . . 103.2(5) ?
C12A C11A H11A . . 111.1 ?
N1 C11A H11A . . 111.1 ?
C12A C11A H11B . . 111.1 ?
N1 C11A H11B . . 111.1 ?
H11A C11A H11B . . 109.1 ?
N1 C11B C12B . . 108.5(5) ?
N1 C11B H11C . . 110.0 ?
C12B C11B H11C . . 110.0 ?
N1 C11B H11D . . 110.0 ?
C12B C11B H11D . . 110.0 ?
H11C C11B H11D . . 108.4 ?
C11B C12B H12D . . 109.5 ?
C11B C12B H12E . . 109.5 ?
H12D C12B H12E . . 109.5 ?
C11B C12B H12F . . 109.5 ?
H12D C12B H12F . . 109.5 ?
H12E C12B H12F . . 109.5 ?
N1 C13 C14 . . 114.33(19) ?
N1 C13 H13A . . 108.7 ?
C14 C13 H13A . . 108.7 ?
N1 C13 H13B . . 108.7 ?
C14 C13 H13B . . 108.7 ?
H13A C13 H13B . . 107.6 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 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
O1 C5 . 1.3774(19) ?
O1 C1 . 1.382(2) ?
O2 C1 . 1.205(2) ?
O3 C10 . 1.206(2) ?
N1 C7 . 1.358(2) ?
N1 C11B . 1.446(6) ?
N1 C13 . 1.457(3) ?
N1 C11A . 1.581(8) ?
C1 C2 . 1.452(3) ?
C2 C3 . 1.359(2) ?
C2 C10 . 1.456(3) ?
C3 C4 . 1.402(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.402(2) ?
C4 C9 . 1.408(2) ?
C5 C6 . 1.367(2) ?
C6 C7 . 1.408(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.423(2) ?
C8 C9 . 1.351(2) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11A C12A . 1.500(8) ?
C11A H11A . 0.9700 ?
C11A H11B . 0.9700 ?
C12A H12A . 0.9600 ?
C12A H12B . 0.9600 ?
C12A H12C . 0.9600 ?
C11B C12B . 1.517(7) ?
C11B H11C . 0.9700 ?
C11B H11D . 0.9700 ?
C12B H12D . 0.9600 ?
C12B H12E . 0.9600 ?
C12B H12F . 0.9600 ?
C13 C14 . 1.512(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 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 O3 4_557 0.93 2.58 3.367(4) 143.4
C9 H9 O1 6_556 0.93 2.55 3.432(3) 157.6
C13 H13B O2 4_556 0.97 2.53 3.388(3) 146.9
