#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/57/2225706.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_2225706
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Goh, Jia Hao'
'Yu, Haitao'
'Zhang, Yan'
_publ_section_title
;
 4-[(2,4-Dimethyl-1,3-oxazol-5-yl)methyl]-4-hydroxy-2-methylisoquinoline-1,3(2H,4H)-dione
;
_journal_coeditor_code           SJ2737
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o724
_journal_page_last               o725
_journal_paper_doi               10.1107/S1600536810007397
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H16 N2 O4'
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_name_systematic
;
4-[(2,4-Dimethyl-1,3-oxazol-5-yl)methyl]-4-hydroxy-2-methylisoquinoline-
1,3(2H,4H)-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.997(3)
_cell_angle_beta                 90.025(3)
_cell_angle_gamma                112.663(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3866(5)
_cell_length_b                   8.8044(5)
_cell_length_c                   10.6734(7)
_cell_measurement_reflns_used    1833
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.74
_cell_measurement_theta_min      4.39
_cell_volume                     701.80(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6623
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0731P)²+0.0844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                2401
_reflns_number_total             3198
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2737.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        701.80(7)
_cod_database_code               2225706
_cod_database_fobs_code          2225706
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
O O1 1.23014(16) 0.40877(16) 0.32581(13) 0.0234(3) Uani d . 1 . .
O O2 0.76462(17) 0.27268(17) 0.04028(14) 0.0269(3) Uani d . 1 . .
O O3 1.13932(17) 0.07862(17) 0.33591(13) 0.0224(3) Uani d . 1 . .
O O4 0.78937(15) 0.36205(15) 0.40053(12) 0.0185(3) Uani d . 1 . .
N N1 0.99911(18) 0.34315(18) 0.18332(15) 0.0175(3) Uani d . 1 . .
N N2 0.50707(18) 0.22071(19) 0.33559(15) 0.0186(3) Uani d . 1 . .
C C1 1.0928(2) 0.3023(2) 0.26656(17) 0.0175(4) Uani d . 1 . .
C C2 0.8503(2) 0.2243(2) 0.10092(18) 0.0187(4) Uani d . 1 . .
C C3 0.8116(2) 0.0419(2) 0.08846(17) 0.0175(4) Uani d . 1 . .
C C4 0.6900(2) -0.0817(2) -0.01212(19) 0.0217(4) Uani d . 1 . .
C C5 0.6559(2) -0.2517(3) -0.0275(2) 0.0249(4) Uani d . 1 . .
C C6 0.7436(3) -0.3003(2) 0.0555(2) 0.0249(4) Uani d . 1 . .
C C7 0.8637(2) -0.1782(2) 0.15593(19) 0.0209(4) Uani d . 1 . .
C C8 0.8972(2) -0.0063(2) 0.17380(17) 0.0171(4) Uani d . 1 . .
C C9 1.0118(2) 0.1260(2) 0.29105(18) 0.0175(4) Uani d . 1 . .
C C10 0.8979(2) 0.1419(3) 0.40732(18) 0.0191(4) Uani d . 1 . .
C C11 0.7513(2) 0.1891(2) 0.38373(17) 0.0172(4) Uani d . 1 . .
C C12 0.5796(2) 0.1033(2) 0.34423(17) 0.0180(4) Uani d . 1 . .
C C13 0.6360(2) 0.3692(2) 0.36869(17) 0.0179(4) Uani d . 1 . .
C C14 1.0594(3) 0.5246(2) 0.1865(2) 0.0238(4) Uani d . 1 . .
C C15 0.4717(3) -0.0836(2) 0.3101(2) 0.0238(4) Uani d . 1 . .
C C16 0.6387(2) 0.5395(2) 0.3724(2) 0.0216(4) Uani d . 1 . .
H H1O3 1.243(4) 0.142(3) 0.321(3) 0.054(8) Uiso d . 1 . .
H H4A 0.637(3) -0.043(3) -0.065(2) 0.033(6) Uiso d . 1 . .
H H5A 0.574(3) -0.336(3) -0.097(2) 0.031(6) Uiso d . 1 . .
H H6A 0.722(3) -0.420(3) 0.045(2) 0.029(6) Uiso d . 1 . .
H H7A 0.924(3) -0.208(2) 0.217(2) 0.019(5) Uiso d . 1 . .
H H10A 0.855(3) 0.032(3) 0.430(2) 0.024(5) Uiso d . 1 . .
H H10B 0.979(3) 0.226(3) 0.484(2) 0.024(5) Uiso d . 1 . .
H H14A 1.064(3) 0.595(3) 0.277(3) 0.045(7) Uiso d . 1 . .
H H14B 0.985(3) 0.538(3) 0.127(3) 0.048(7) Uiso d . 1 . .
H H14C 1.175(4) 0.565(3) 0.154(3) 0.052(8) Uiso d . 1 . .
H H15A 0.436(3) -0.124(3) 0.215(3) 0.037(6) Uiso d . 1 . .
H H15B 0.530(3) -0.148(3) 0.337(2) 0.040(7) Uiso d . 1 . .
H H15C 0.360(3) -0.114(3) 0.349(3) 0.047(7) Uiso d . 1 . .
H H16A 0.526(3) 0.529(3) 0.344(2) 0.037(6) Uiso d . 1 . .
H H16B 0.682(3) 0.622(3) 0.461(3) 0.039(6) Uiso d . 1 . .
H H16C 0.718(4) 0.594(3) 0.314(3) 0.053(8) Uiso 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
C9 O3 H1O3 . . 111.7(18) ?
C13 O4 C11 . . 105.09(13) ?
C1 N1 C2 . . 124.28(14) ?
C1 N1 C14 . . 116.33(15) ?
C2 N1 C14 . . 119.36(14) ?
C13 N2 C12 . . 105.17(14) ?
O1 C1 N1 . . 120.67(16) ?
O1 C1 C9 . . 121.09(15) ?
N1 C1 C9 . . 118.01(15) ?
O2 C2 N1 . . 120.21(16) ?
O2 C2 C3 . . 123.36(17) ?
N1 C2 C3 . . 116.36(14) ?
C8 C3 C4 . . 120.28(16) ?
C8 C3 C2 . . 120.80(16) ?
C4 C3 C2 . . 118.91(16) ?
C5 C4 C3 . . 119.75(18) ?
C5 C4 H4A . . 123.9(14) ?
C3 C4 H4A . . 116.4(14) ?
C4 C5 C6 . . 120.24(18) ?
C4 C5 H5A . . 119.7(13) ?
C6 C5 H5A . . 120.0(13) ?
C7 C6 C5 . . 120.25(18) ?
C7 C6 H6A . . 118.6(13) ?
C5 C6 H6A . . 121.1(13) ?
C6 C7 C8 . . 120.05(18) ?
C6 C7 H7A . . 122.2(12) ?
C8 C7 H7A . . 117.7(12) ?
C7 C8 C3 . . 119.42(17) ?
C7 C8 C9 . . 120.71(16) ?
C3 C8 C9 . . 119.63(15) ?
O3 C9 C8 . . 112.25(14) ?
O3 C9 C1 . . 111.38(14) ?
C8 C9 C1 . . 111.91(14) ?
O3 C9 C10 . . 105.32(14) ?
C8 C9 C10 . . 109.17(14) ?
C1 C9 C10 . . 106.39(14) ?
C11 C10 C9 . . 115.98(15) ?
C11 C10 H10A . . 110.1(12) ?
C9 C10 H10A . . 106.9(13) ?
C11 C10 H10B . . 111.0(12) ?
C9 C10 H10B . . 106.8(12) ?
H10A C10 H10B . . 105.3(17) ?
C12 C11 O4 . . 107.30(14) ?
C12 C11 C10 . . 135.61(17) ?
O4 C11 C10 . . 117.05(15) ?
C11 C12 N2 . . 108.95(15) ?
C11 C12 C15 . . 129.76(17) ?
N2 C12 C15 . . 121.29(15) ?
N2 C13 O4 . . 113.49(15) ?
N2 C13 C16 . . 129.41(16) ?
O4 C13 C16 . . 117.08(15) ?
N1 C14 H14A . . 110.5(14) ?
N1 C14 H14B . . 109.2(15) ?
H14A C14 H14B . . 112(2) ?
N1 C14 H14C . . 110.9(15) ?
H14A C14 H14C . . 110(2) ?
H14B C14 H14C . . 104(2) ?
C12 C15 H15A . . 108.7(13) ?
C12 C15 H15B . . 112.9(14) ?
H15A C15 H15B . . 111(2) ?
C12 C15 H15C . . 113.7(15) ?
H15A C15 H15C . . 104(2) ?
H15B C15 H15C . . 106(2) ?
C13 C16 H16A . . 110.0(14) ?
C13 C16 H16B . . 112.3(13) ?
H16A C16 H16B . . 111(2) ?
C13 C16 H16C . . 112.0(16) ?
H16A C16 H16C . . 106(2) ?
H16B C16 H16C . . 105(2) ?
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 . 1.219(2) ?
O2 C2 . 1.219(2) ?
O3 C9 . 1.4096(19) ?
O3 H1O3 . 0.87(3) ?
O4 C13 . 1.3590(19) ?
O4 C11 . 1.395(2) ?
N1 C1 . 1.381(2) ?
N1 C2 . 1.405(2) ?
N1 C14 . 1.469(2) ?
N2 C13 . 1.300(2) ?
N2 C12 . 1.407(2) ?
C1 C9 . 1.524(2) ?
C2 C3 . 1.482(2) ?
C3 C8 . 1.395(2) ?
C3 C4 . 1.398(3) ?
C4 C5 . 1.379(3) ?
C4 H4A . 0.91(2) ?
C5 C6 . 1.391(3) ?
C5 H5A . 0.96(2) ?
C6 C7 . 1.388(3) ?
C6 H6A . 0.98(2) ?
C7 C8 . 1.392(2) ?
C7 H7A . 0.97(2) ?
C8 C9 . 1.510(2) ?
C9 C10 . 1.579(3) ?
C10 C11 . 1.481(2) ?
C10 H10A . 0.99(2) ?
C10 H10B . 1.00(2) ?
C11 C12 . 1.352(2) ?
C12 C15 . 1.491(3) ?
C13 C16 . 1.481(3) ?
C14 H14A . 1.01(3) ?
C14 H14B . 0.94(3) ?
C14 H14C . 0.99(3) ?
C15 H15A . 1.00(3) ?
C15 H15B . 0.97(2) ?
C15 H15C . 0.99(3) ?
C16 H16A . 0.95(2) ?
C16 H16B . 1.01(3) ?
C16 H16C . 0.98(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 H1O3 N2 1_655 0.87(3) 2.04(3) 2.847(2) 153(3) yes
C16 H16A O1 1_455 0.96(3) 2.28(3) 3.162(2) 153(2) yes
C16 H16B O1 2_766 1.01(3) 2.50(3) 3.270(2) 132.9(19) yes
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
C2 N1 C1 O1 . . . . 172.69(16) ?
C14 N1 C1 O1 . . . . -9.2(3) ?
C2 N1 C1 C9 . . . . -12.7(2) ?
C14 N1 C1 C9 . . . . 165.40(16) ?
C1 N1 C2 O2 . . . . 172.40(17) ?
C14 N1 C2 O2 . . . . -5.6(3) ?
C1 N1 C2 C3 . . . . -10.5(2) ?
C14 N1 C2 C3 . . . . 171.54(16) ?
O2 C2 C3 C8 . . . . -170.30(17) ?
N1 C2 C3 C8 . . . . 12.7(2) ?
O2 C2 C3 C4 . . . . 11.0(3) ?
N1 C2 C3 C4 . . . . -166.05(16) ?
C8 C3 C4 C5 . . . . -0.6(3) ?
C2 C3 C4 C5 . . . . 178.13(17) ?
C3 C4 C5 C6 . . . . -0.8(3) ?
C4 C5 C6 C7 . . . . 1.1(3) ?
C5 C6 C7 C8 . . . . -0.1(3) ?
C6 C7 C8 C3 . . . . -1.3(3) ?
C6 C7 C8 C9 . . . . 173.05(17) ?
C4 C3 C8 C7 . . . . 1.6(3) ?
C2 C3 C8 C7 . . . . -177.07(16) ?
C4 C3 C8 C9 . . . . -172.78(16) ?
C2 C3 C8 C9 . . . . 8.5(3) ?
C7 C8 C9 O3 . . . . 29.8(2) ?
C3 C8 C9 O3 . . . . -155.84(15) ?
C7 C8 C9 C1 . . . . 155.93(16) ?
C3 C8 C9 C1 . . . . -29.7(2) ?
C7 C8 C9 C10 . . . . -86.56(19) ?
C3 C8 C9 C10 . . . . 87.76(19) ?
O1 C1 C9 O3 . . . . -27.0(2) ?
N1 C1 C9 O3 . . . . 158.35(15) ?
O1 C1 C9 C8 . . . . -153.60(16) ?
N1 C1 C9 C8 . . . . 31.8(2) ?
O1 C1 C9 C10 . . . . 87.24(19) ?
N1 C1 C9 C10 . . . . -87.39(18) ?
O3 C9 C10 C11 . . . . -179.26(15) ?
C8 C9 C10 C11 . . . . -58.5(2) ?
C1 C9 C10 C11 . . . . 62.40(19) ?
C13 O4 C11 C12 . . . . -0.42(18) ?
C13 O4 C11 C10 . . . . 177.85(15) ?
C9 C10 C11 C12 . . . . 95.1(3) ?
C9 C10 C11 O4 . . . . -82.6(2) ?
O4 C11 C12 N2 . . . . 0.00(19) ?
C10 C11 C12 N2 . . . . -177.81(19) ?
O4 C11 C12 C15 . . . . 178.81(18) ?
C10 C11 C12 C15 . . . . 1.0(4) ?
C13 N2 C12 C11 . . . . 0.4(2) ?
C13 N2 C12 C15 . . . . -178.48(17) ?
C12 N2 C13 O4 . . . . -0.7(2) ?
C12 N2 C13 C16 . . . . 177.28(19) ?
C11 O4 C13 N2 . . . . 0.75(19) ?
C11 O4 C13 C16 . . . . -177.54(16) ?
