#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/88/2208873.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_2208873
loop_
_publ_author_name
'Hamaker, Christopher G.'
'McCully, Charles S.'
_publ_section_title
;
 3-Acetyl-7-(diethylamino)coumarin
;
_journal_coeditor_code           DN2031
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2072
_journal_page_last               o2074
_journal_paper_doi               10.1107/S1600536806014899
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H17 N1 O3'
_chemical_formula_moiety         'C15 H17 N1 O3'
_chemical_formula_sum            'C15 H17 N O3'
_chemical_formula_weight         259.3
_chemical_name_systematic
;
3-Acetyl-7-(diethylamino)coumarin
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.524(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.269(2)
_cell_length_b                   7.5203(8)
_cell_length_c                   22.0868(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      13.90
_cell_measurement_theta_min      7.31
_cell_volume                     2719.8(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'MERCURY (Bruno et al.,  2002) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            3217
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1085P)²+0.3073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1992
_reflns_number_gt                1984
_reflns_number_total             3118
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2031.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2208873
_cod_database_fobs_code          2208873
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
C C2 0.24645(12) -0.0212(3) 0.50400(10) 0.0411(4) Uani d . 1
C C3 0.24620(12) 0.0570(3) 0.44395(9) 0.0406(4) Uani d . 1
C C4 0.31476(12) 0.1420(3) 0.44062(9) 0.0417(5) Uani d . 1
H H4 0.3136 0.1941 0.4022 0.05 Uiso calc R 1
C C5 0.46020(12) 0.2355(3) 0.49209(10) 0.0440(5) Uani d . 1
H H5 0.462 0.2898 0.4547 0.053 Uiso calc R 1
C C6 0.52837(12) 0.2375(3) 0.54421(10) 0.0435(5) Uani d . 1
H H6 0.5755 0.2927 0.5419 0.052 Uiso calc R 1
C C7 0.52814(12) 0.1553(3) 0.60256(9) 0.0393(4) Uani d . 1
C C8 0.45510(12) 0.0734(3) 0.60396(9) 0.0413(5) Uani d . 1
H H8 0.4528 0.0189 0.6411 0.05 Uiso calc R 1
C C9 0.38745(11) 0.0744(2) 0.55036(9) 0.0367(4) Uani d . 1
C C10 0.38671(12) 0.1539(2) 0.49277(9) 0.0384(4) Uani d . 1
C C12 0.17408(13) 0.0451(3) 0.38463(10) 0.0496(5) Uani d . 1
C C14 0.09845(15) -0.0521(4) 0.38423(13) 0.0640(7) Uani d . 1
H H14A 0.0756 0.0028 0.414 0.096 Uiso calc R 1
H H14B 0.1117 -0.1738 0.3963 0.096 Uiso calc R 1
H H14C 0.0594 -0.0478 0.3421 0.096 Uiso calc R 1
C C16 0.67185(12) 0.2468(3) 0.65512(11) 0.0498(5) Uani d . 1
H H16A 0.6791 0.2333 0.6136 0.06 Uiso calc R 1
H H16B 0.718 0.191 0.6865 0.06 Uiso calc R 1
C C17 0.67079(17) 0.4430(3) 0.67040(13) 0.0681(7) Uani d . 1
H H17A 0.7212 0.4965 0.6703 0.102 Uiso calc R 1
H H17B 0.6644 0.4571 0.7117 0.102 Uiso calc R 1
H H17C 0.6261 0.4995 0.6388 0.102 Uiso calc R 1
C C18 0.59596(15) 0.0824(3) 0.71587(10) 0.0565(6) Uani d . 1
H H18A 0.5433 0.1062 0.7213 0.068 Uiso calc R 1
H H18B 0.6374 0.1419 0.7502 0.068 Uiso calc R 1
C C19 0.6117(2) -0.1152(4) 0.72090(14) 0.0796(9) Uani d . 1
H H19A 0.6102 -0.1569 0.7616 0.119 Uiso calc R 1
H H19B 0.6644 -0.1394 0.7168 0.119 Uiso calc R 1
H H19C 0.5704 -0.1751 0.6875 0.119 Uiso calc R 1
N N15 0.59663(10) 0.1560(2) 0.65482(8) 0.0468(4) Uani d . 1
O O1 0.31849(8) -0.00729(18) 0.55500(6) 0.0431(4) Uani d . 1
O O11 0.19136(9) -0.0979(2) 0.51581(8) 0.0592(5) Uani d . 1
O O13 0.17832(11) 0.1158(3) 0.33609(8) 0.0806(6) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 2 3
3 1 -10
3 -1 -10
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 C2 O1 . 115.04(18) ?
O11 C2 C3 . 128.1(2) ?
O1 C2 C3 . 116.88(17) ?
O11 C2 O11 7_546 85.53(13) ?
O1 C2 O11 7_546 85.63(11) ?
C3 C2 O11 7_546 98.30(12) ?
C4 C3 C2 . 119.19(18) ?
C4 C3 C12 . 118.36(18) ?
C2 C3 C12 . 122.44(18) ?
C3 C4 C10 . 122.78(18) ?
C3 C4 H4 . 118.6 ?
C10 C4 H4 . 118.6 ?
C6 C5 C10 . 122.28(18) ?
C6 C5 H5 . 118.9 ?
C10 C5 H5 . 118.9 ?
C5 C6 C7 . 120.55(18) ?
C5 C6 H6 . 119.7 ?
C7 C6 H6 . 119.7 ?
N15 C7 C8 . 121.54(17) ?
N15 C7 C6 . 120.69(17) ?
C8 C7 C6 . 117.78(17) ?
C9 C8 C7 . 119.98(17) ?
C9 C8 H8 . 120 ?
C7 C8 H8 . 120 ?
O1 C9 C8 . 116.98(16) ?
O1 C9 C10 . 120.05(17) ?
C8 C9 C10 . 122.97(17) ?
C9 C10 C4 . 117.91(17) ?
C9 C10 C5 . 116.44(17) ?
C4 C10 C5 . 125.62(17) ?
O13 C12 C14 . 120.3(2) ?
O13 C12 C3 . 118.5(2) ?
C14 C12 C3 . 121.2(2) ?
C12 C14 H14A . 109.5 ?
C12 C14 H14B . 109.5 ?
H14A C14 H14B . 109.5 ?
C12 C14 H14C . 109.5 ?
H14A C14 H14C . 109.5 ?
H14B C14 H14C . 109.5 ?
N15 C16 C17 . 112.4(2) ?
N15 C16 H16A . 109.1 ?
C17 C16 H16A . 109.1 ?
N15 C16 H16B . 109.1 ?
C17 C16 H16B . 109.1 ?
H16A C16 H16B . 107.9 ?
C16 C17 H17A . 109.5 ?
C16 C17 H17B . 109.5 ?
H17A C17 H17B . 109.5 ?
C16 C17 H17C . 109.5 ?
H17A C17 H17C . 109.5 ?
H17B C17 H17C . 109.5 ?
N15 C18 C19 . 112.8(2) ?
N15 C18 H18A . 109 ?
C19 C18 H18A . 109 ?
N15 C18 H18B . 109 ?
C19 C18 H18B . 109 ?
H18A C18 H18B . 107.8 ?
C18 C19 H19A . 109.5 ?
C18 C19 H19B . 109.5 ?
H19A C19 H19B . 109.5 ?
C18 C19 H19C . 109.5 ?
H19A C19 H19C . 109.5 ?
H19B C19 H19C . 109.5 ?
C7 N15 C18 . 121.34(17) ?
C7 N15 C16 . 122.29(17) ?
C18 N15 C16 . 116.05(17) y
C9 O1 C2 . 123.15(15) ?
C2 O11 C2 7_546 94.47(13) ?
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
C2 O11 . 1.210(2) ?
C2 O1 . 1.392(2) ?
C2 C3 . 1.450(3) ?
C2 O11 7_546 3.139(3) ?
C3 C4 . 1.368(3) ?
C3 C12 . 1.496(3) ?
C4 C10 . 1.403(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.360(3) ?
C5 C10 . 1.414(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.431(3) ?
C6 H6 . 0.93 ?
C7 N15 . 1.365(2) y
C7 C8 . 1.413(3) ?
C8 C9 . 1.374(3) ?
C8 H8 . 0.93 ?
C9 O1 . 1.373(2) ?
C9 C10 . 1.402(3) ?
C12 O13 . 1.220(3) ?
C12 C14 . 1.494(3) ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C16 N15 . 1.466(3) y
C16 C17 . 1.515(3) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 N15 . 1.461(3) y
C18 C19 . 1.508(4) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
O11 C2 7_546 3.139(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
C6 H6 O11 3 0.93 2.40 3.312(2) 168
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_4
_geom_torsion
O11 C2 C3 C4 . . 178.6(2)
O1 C2 C3 C4 . . -1.2(3)
O11 C2 C3 C4 7_546 . -90.54(18)
O11 C2 C3 C12 . . -2.7(3)
O1 C2 C3 C12 . . 177.38(17)
O11 C2 C3 C12 7_546 . 88.09(19)
C2 C3 C4 C10 . . 1.4(3)
C12 C3 C4 C10 . . -177.24(18)
C10 C5 C6 C7 . . 0.1(3)
C5 C6 C7 N15 . . 179.57(19)
C5 C6 C7 C8 . . -0.2(3)
N15 C7 C8 C9 . . -179.64(18)
C6 C7 C8 C9 . . 0.1(3)
C7 C8 C9 O1 . . -179.93(17)
C7 C8 C9 C10 . . 0.1(3)
O1 C9 C10 C4 . . -1.8(3)
C8 C9 C10 C4 . . 178.17(18)
O1 C9 C10 C5 . . 179.83(17)
C8 C9 C10 C5 . . -0.2(3)
C3 C4 C10 C9 . . 0.1(3)
C3 C4 C10 C5 . . 178.28(19)
C6 C5 C10 C9 . . 0.1(3)
C6 C5 C10 C4 . . -178.11(19)
C4 C3 C12 O13 . . -2.0(3)
C2 C3 C12 O13 . . 179.3(2)
C4 C3 C12 C14 . . 177.5(2)
C2 C3 C12 C14 . . -1.1(3)
C8 C7 N15 C18 . . -4.1(3)
C6 C7 N15 C18 . . 176.2(2)
C8 C7 N15 C16 . . -177.30(18)
C6 C7 N15 C16 . . 3.0(3)
C19 C18 N15 C7 . . 85.9(3)
C19 C18 N15 C16 . . -100.5(3)
C17 C16 N15 C7 . . 84.1(2)
C17 C16 N15 C18 . . -89.4(2)
C8 C9 O1 C2 . . -177.95(17)
C10 C9 O1 C2 . . 2.0(3)
O11 C2 O1 C9 . . 179.62(17)
C3 C2 O1 C9 . . -0.5(3)
O11 C2 O1 C9 7_546 . 96.62(16)
O1 C2 O11 C2 . 7_546 -83.06(16)
C3 C2 O11 C2 . 7_546 97.0(2)
O11 C2 O11 C2 7_546 7_546 0
