#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/25/8102531.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102531
loop_
_publ_author_name
'Xiaochuan Li'
'Woo Taik Lim'
'Sung-Hoon Kim'
'Young-A Son'
_publ_section_title
;
 Crystal structure of 3-carboxyethyl-7-diethylaminocoumarin, C16H19NO4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              593
_journal_volume                  224
_journal_year                    2009
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_chemical_name_systematic
;
3-Carboxyethyl-7-diethylaminocoumarin, 
C₁₆H₁₉NO₄ 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.36(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7440(13)
_cell_length_b                   15.846(3)
_cell_length_c                   13.375(3)
_cell_measurement_reflns_used    3705
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.5
_cell_volume                     1417.5(5)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1999)'
_computing_publication_material
'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'ADSC Quantum210'
_diffrn_measurement_method       'two φ and two ω scans with 2° steps'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'synchrotron radiation'
_diffrn_radiation_type           'synchrotron radiation'
_diffrn_radiation_wavelength     0.90000
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3705
_diffrn_reflns_theta_full        30.35
_diffrn_reflns_theta_max         30.35
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             616
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.21(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         1903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0669
_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)+(0.1137P)²+0.3108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1698
_refine_ls_wR_factor_ref         0.1759
_reflns_number_gt                1820
_reflns_number_total             1903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2739.cff
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'NONE' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_database_code               8102531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0894(2) 0.60909(8) 0.93454(10) 0.0324(5) Uani 1 1 d . . .
O2 O 1.2433(2) 0.71660(9) 1.01541(10) 0.0363(5) Uani 1 1 d . . .
O3 O 0.6908(2) 0.81595(8) 1.06463(10) 0.0333(5) Uani 1 1 d . . .
O4 O 1.0082(2) 0.81339(9) 1.14060(11) 0.0399(5) Uani 1 1 d . . .
N1 N 0.7981(3) 0.38150(10) 0.73439(11) 0.0336(6) Uani 1 1 d . . .
C1 C 0.5482(4) 0.26566(13) 0.73554(16) 0.0406(6) Uani 1 1 d . . .
H1A H 0.6490 0.2226 0.7439 0.061 Uiso 1 1 calc R . .
H1B H 0.4291 0.2435 0.6976 0.061 Uiso 1 1 calc R . .
H1C H 0.5189 0.2838 0.8005 0.061 Uiso 1 1 calc R . .
C2 C 0.6234(3) 0.34014(13) 0.67963(14) 0.0343(6) Uani 1 1 d . . .
H2A H 0.6571 0.3207 0.6151 0.041 Uiso 1 1 calc R . .
H2B H 0.5165 0.3812 0.6665 0.041 Uiso 1 1 calc R . .
C3 C 1.0472(3) 0.40868(14) 0.61688(15) 0.0399(6) Uani 1 1 d . . .
H3A H 0.9472 0.4015 0.5596 0.060 Uiso 1 1 calc R . .
H3B H 1.1743 0.3901 0.6000 0.060 Uiso 1 1 calc R . .
H3C H 1.0555 0.4672 0.6355 0.060 Uiso 1 1 calc R . .
C4 C 0.9912(3) 0.35682(13) 0.70477(15) 0.0356(6) Uani 1 1 d . . .
H4A H 0.9865 0.2976 0.6861 0.043 Uiso 1 1 calc R . .
H4B H 1.0939 0.3636 0.7620 0.043 Uiso 1 1 calc R . .
C5 C 0.5715(3) 0.53557(12) 0.89029(14) 0.0322(6) Uani 1 1 d . . .
H5 H 0.4456 0.5487 0.9072 0.039 Uiso 1 1 calc R . .
C6 C 0.5926(3) 0.46752(12) 0.82963(14) 0.0325(6) Uani 1 1 d . . .
H6 H 0.4814 0.4346 0.8074 0.039 Uiso 1 1 calc R . .
C7 C 0.7815(3) 0.44616(12) 0.79986(13) 0.0313(6) Uani 1 1 d . . .
C8 C 0.9476(3) 0.49510(13) 0.83948(13) 0.0317(6) Uani 1 1 d . . .
H8 H 1.0744 0.4817 0.8239 0.038 Uiso 1 1 calc R . .
C9 C 0.9222(3) 0.56272(12) 0.90120(14) 0.0312(6) Uani 1 1 d . . .
C10 C 0.7357(3) 0.58612(12) 0.92771(14) 0.0312(6) Uani 1 1 d . . .
C11 C 0.7248(3) 0.65933(12) 0.98691(13) 0.0313(6) Uani 1 1 d . . .
H11 H 0.6012 0.6763 1.0036 0.038 Uiso 1 1 calc R . .
C12 C 1.0858(3) 0.68110(12) 0.99430(14) 0.0322(6) Uani 1 1 d . . .
C13 C 0.8907(3) 0.70605(12) 1.02051(14) 0.0316(6) Uani 1 1 d . . .
C14 C 0.8761(3) 0.78307(12) 1.08209(14) 0.0317(6) Uani 1 1 d . . .
C15 C 0.6555(3) 0.89054(12) 1.12375(15) 0.0349(6) Uani 1 1 d . . .
H15A H 0.7443 0.9359 1.1096 0.042 Uiso 1 1 calc R . .
H15B H 0.6791 0.8778 1.1952 0.042 Uiso 1 1 calc R . .
C16 C 0.4419(3) 0.91564(13) 1.09400(15) 0.0371(6) Uani 1 1 d . . .
H16A H 0.4228 0.9318 1.0242 0.056 Uiso 1 1 calc R . .
H16B H 0.4098 0.9624 1.1346 0.056 Uiso 1 1 calc R . .
H16C H 0.3562 0.8689 1.1040 0.056 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C12 123.37(15) . . ?
C14 O3 C15 115.58(15) . . ?
C7 N1 C2 122.21(17) . . ?
C7 N1 C4 121.65(17) . . ?
C2 N1 C4 115.67(16) . . ?
N1 C2 C1 113.62(16) . . ?
N1 C4 C3 112.52(17) . . ?
C6 C5 C10 121.56(19) . . ?
C5 C6 C7 121.21(19) . . ?
N1 C7 C8 121.96(19) . . ?
N1 C7 C6 120.59(18) . . ?
C8 C7 C6 117.45(17) . . ?
C9 C8 C7 119.99(19) . . ?
O1 C9 C8 116.83(18) . . ?
O1 C9 C10 120.25(17) . . ?
C8 C9 C10 122.90(19) . . ?
C9 C10 C5 116.81(18) . . ?
C9 C10 C11 118.22(19) . . ?
C5 C10 C11 124.94(19) . . ?
C13 C11 C10 121.98(19) . . ?
O2 C12 O1 115.92(18) . . ?
O2 C12 C13 127.81(18) . . ?
O1 C12 C13 116.23(17) . . ?
C11 C13 C12 119.93(18) . . ?
C11 C13 C14 121.18(19) . . ?
C12 C13 C14 118.88(18) . . ?
O4 C14 O3 123.35(18) . . ?
O4 C14 C13 126.2(2) . . ?
O3 C14 C13 110.40(17) . . ?
O3 C15 C16 106.81(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.372(3) . ?
O1 C12 1.395(2) . ?
O2 C12 1.203(2) . ?
O3 C14 1.346(3) . ?
O3 C15 1.459(2) . ?
O4 C14 1.207(3) . ?
N1 C7 1.362(2) . ?
N1 C2 1.460(3) . ?
N1 C4 1.462(3) . ?
C1 C2 1.519(3) . ?
C3 C4 1.521(3) . ?
C5 C6 1.368(3) . ?
C5 C10 1.406(3) . ?
C6 C7 1.424(3) . ?
C7 C8 1.409(3) . ?
C8 C9 1.377(3) . ?
C9 C10 1.400(3) . ?
C10 C11 1.412(3) . ?
C11 C13 1.368(3) . ?
C12 C13 1.459(3) . ?
C13 C14 1.483(3) . ?
C15 C16 1.498(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 107142
