#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/04/2230469.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_2230469
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
'Xu, Kai'
'Zhang, Yan'
_publ_section_title
;
 Methyl
 4'-isobutyl-2,2'-dimethyl-1,3-dioxo-2,3-dihydro-1H,4'H-spiro[isoquinoline-4,5'-oxazole]-4'-carboxylate
;
_journal_coeditor_code           RZ2597
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1519
_journal_page_last               o1520
_journal_paper_doi               10.1107/S1600536811019003
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H22 N2 O5'
_chemical_formula_moiety         'C19 H22 N2 O5'
_chemical_formula_sum            'C19 H22 N2 O5'
_chemical_formula_weight         358.39
_chemical_name_systematic
;
Methyl 4'-isobutyl-2,2'-dimethyl-1,3-dioxo-2,3-dihydro-1H,4'H-
spiro[isoquinoline-4,5'-oxazole]-4'-carboxylate
;
_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                93.4950(10)
_cell_angle_beta                 109.8920(10)
_cell_angle_gamma                98.4260(10)
_cell_formula_units_Z            2
_cell_length_a                   8.67640(10)
_cell_length_b                   8.93660(10)
_cell_length_c                   12.0684(2)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.05
_cell_measurement_theta_min      2.32
_cell_volume                     864.23(2)
_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
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and 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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25638
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         1.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         6231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0637P)²+0.1577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                5381
_reflns_number_total             6231
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2597.cif
_cod_data_source_block           I
_cod_original_cell_volume        864.22(2)
_cod_database_code               2230469
_cod_database_fobs_code          2230469
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.56369(10) -0.13923(8) 0.36689(7) 0.02808(16) Uani d . 1 1 . .
O O2 0.61673(8) 0.30662(7) 0.21139(6) 0.01906(13) Uani d . 1 1 . .
O O3 0.70178(7) 0.17637(7) 0.03819(5) 0.01584(12) Uani d . 1 1 . .
O O4 1.13223(8) 0.01941(7) 0.19476(6) 0.02001(13) Uani d . 1 1 . .
O O5 1.02241(8) 0.00373(7) 0.33903(6) 0.01843(13) Uani d . 1 1 . .
N N1 0.60176(9) 0.08767(8) 0.29574(6) 0.01547(13) Uani d . 1 1 . .
N N2 0.98015(8) 0.26379(8) 0.11623(6) 0.01398(13) Uani d . 1 1 . .
C C1 0.71382(9) -0.05589(9) 0.12763(7) 0.01375(14) Uani d . 1 1 . .
C C2 0.75196(10) -0.12948(9) 0.03755(7) 0.01669(15) Uani d . 1 1 . .
H H2A 0.7913 -0.0729 -0.0126 0.020 Uiso calc R 1 1 . .
C C3 0.73110(11) -0.28759(10) 0.02283(8) 0.01903(16) Uani d . 1 1 . .
H H3A 0.7556 -0.3364 -0.0378 0.023 Uiso calc R 1 1 . .
C C4 0.67396(11) -0.37359(10) 0.09800(8) 0.01860(16) Uani d . 1 1 . .
H H4A 0.6621 -0.4792 0.0884 0.022 Uiso calc R 1 1 . .
C C5 0.63485(10) -0.30090(9) 0.18736(7) 0.01695(15) Uani d . 1 1 . .
H H5A 0.5961 -0.3578 0.2376 0.020 Uiso calc R 1 1 . .
C C6 0.65376(10) -0.14210(9) 0.20173(7) 0.01444(14) Uani d . 1 1 . .
C C7 0.60524(10) -0.06867(10) 0.29540(7) 0.01696(15) Uani d . 1 1 . .
C C8 0.64684(9) 0.17845(9) 0.21858(7) 0.01427(14) Uani d . 1 1 . .
C C9 0.74719(9) 0.11548(9) 0.15004(7) 0.01297(13) Uani d . 1 1 . .
C C10 0.94372(9) 0.18962(9) 0.21130(7) 0.01221(13) Uani d . 1 1 . .
C C11 0.84438(10) 0.25402(9) 0.02944(7) 0.01396(14) Uani d . 1 1 . .
C C12 0.81958(11) 0.31809(10) -0.08488(7) 0.01760(15) Uani d . 1 1 . .
H H12A 0.9226 0.3774 -0.0823 0.026 Uiso calc R 1 1 . .
H H12B 0.7366 0.3818 -0.0976 0.026 Uiso calc R 1 1 . .
H H12C 0.7834 0.2365 -0.1486 0.026 Uiso calc R 1 1 . .
C C13 0.98781(9) 0.30600(9) 0.32243(7) 0.01391(14) Uani d . 1 1 . .
H H13A 0.9391 0.3950 0.2979 0.017 Uiso calc R 1 1 . .
H H13B 0.9362 0.2612 0.3753 0.017 Uiso calc R 1 1 . .
C C14 1.17540(9) 0.35881(9) 0.39278(7) 0.01424(14) Uani d . 1 1 . .
H H14A 1.2278 0.2682 0.4053 0.017 Uiso calc R 1 1 . .
C C15 1.19883(11) 0.43954(11) 0.51412(8) 0.02220(17) Uani d . 1 1 . .
H H15A 1.3156 0.4677 0.5597 0.033 Uiso calc R 1 1 . .
H H15B 1.1464 0.3723 0.5551 0.033 Uiso calc R 1 1 . .
H H15C 1.1492 0.5293 0.5039 0.033 Uiso calc R 1 1 . .
C C16 1.26352(11) 0.46363(11) 0.32908(8) 0.02157(17) Uani d . 1 1 . .
H H16A 1.3776 0.4980 0.3794 0.032 Uiso calc R 1 1 . .
H H16B 1.2091 0.5499 0.3110 0.032 Uiso calc R 1 1 . .
H H16C 1.2593 0.4089 0.2568 0.032 Uiso calc R 1 1 . .
C C17 1.04488(9) 0.06210(9) 0.24456(7) 0.01415(14) Uani d . 1 1 . .
C C18 1.10003(13) -0.12653(12) 0.37361(10) 0.0282(2) Uani d . 1 1 . .
H H18A 1.0943 -0.1492 0.4490 0.042 Uiso calc R 1 1 . .
H H18B 1.2145 -0.1044 0.3798 0.042 Uiso calc R 1 1 . .
H H18C 1.0429 -0.2127 0.3151 0.042 Uiso calc R 1 1 . .
C C19 0.52591(11) 0.15905(10) 0.37250(8) 0.02020(16) Uani d . 1 1 . .
H H19A 0.6016 0.2477 0.4198 0.030 Uiso calc R 1 1 . .
H H19B 0.5024 0.0878 0.4235 0.030 Uiso calc R 1 1 . .
H H19C 0.4243 0.1883 0.3243 0.030 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
C11 O3 C9 . . 107.44(6) ?
C17 O5 C18 . . 115.39(7) ?
C8 N1 C7 . . 124.82(7) ?
C8 N1 C19 . . 116.23(7) ?
C7 N1 C19 . . 118.50(7) ?
C11 N2 C10 . . 108.20(6) ?
C2 C1 C6 . . 119.53(7) ?
C2 C1 C9 . . 120.39(7) ?
C6 C1 C9 . . 119.97(7) ?
C3 C2 C1 . . 119.87(8) ?
C3 C2 H2A . . 120.1 ?
C1 C2 H2A . . 120.1 ?
C2 C3 C4 . . 120.66(8) ?
C2 C3 H3A . . 119.7 ?
C4 C3 H3A . . 119.7 ?
C5 C4 C3 . . 119.68(8) ?
C5 C4 H4A . . 120.2 ?
C3 C4 H4A . . 120.2 ?
C4 C5 C6 . . 119.92(8) ?
C4 C5 H5A . . 120.0 ?
C6 C5 H5A . . 120.0 ?
C1 C6 C5 . . 120.33(8) ?
C1 C6 C7 . . 121.22(7) ?
C5 C6 C7 . . 118.43(7) ?
O1 C7 N1 . . 120.23(8) ?
O1 C7 C6 . . 122.86(8) ?
N1 C7 C6 . . 116.85(7) ?
O2 C8 N1 . . 121.17(8) ?
O2 C8 C9 . . 121.21(7) ?
N1 C8 C9 . . 117.46(7) ?
O3 C9 C1 . . 109.04(6) ?
O3 C9 C8 . . 106.82(6) ?
C1 C9 C8 . . 113.48(6) ?
O3 C9 C10 . . 102.23(6) ?
C1 C9 C10 . . 113.79(6) ?
C8 C9 C10 . . 110.63(6) ?
N2 C10 C17 . . 110.09(6) ?
N2 C10 C13 . . 110.48(6) ?
C17 C10 C13 . . 108.90(6) ?
N2 C10 C9 . . 103.04(6) ?
C17 C10 C9 . . 109.24(6) ?
C13 C10 C9 . . 114.95(6) ?
N2 C11 O3 . . 118.54(7) ?
N2 C11 C12 . . 127.35(7) ?
O3 C11 C12 . . 114.11(7) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C10 . . 115.65(6) ?
C14 C13 H13A . . 108.4 ?
C10 C13 H13A . . 108.4 ?
C14 C13 H13B . . 108.4 ?
C10 C13 H13B . . 108.4 ?
H13A C13 H13B . . 107.4 ?
C16 C14 C15 . . 109.57(7) ?
C16 C14 C13 . . 113.42(7) ?
C15 C14 C13 . . 109.33(7) ?
C16 C14 H14A . . 108.1 ?
C15 C14 H14A . . 108.1 ?
C13 C14 H14A . . 108.1 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O4 C17 O5 . . 124.41(7) ?
O4 C17 C10 . . 125.85(7) ?
O5 C17 C10 . . 109.73(7) ?
O5 C18 H18A . . 109.5 ?
O5 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O5 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N1 C19 H19A . . 109.5 ?
N1 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
N1 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 C7 . 1.2178(10) ?
O2 C8 . 1.2133(10) ?
O3 C11 . 1.3675(10) ?
O3 C9 . 1.4365(9) ?
O4 C17 . 1.2033(10) ?
O5 C17 . 1.3431(10) ?
O5 C18 . 1.4424(11) ?
N1 C8 . 1.3875(10) ?
N1 C7 . 1.4016(11) ?
N1 C19 . 1.4711(11) ?
N2 C11 . 1.2694(10) ?
N2 C10 . 1.4608(10) ?
C1 C2 . 1.3948(11) ?
C1 C6 . 1.3958(11) ?
C1 C9 . 1.5062(11) ?
C2 C3 . 1.3904(12) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3925(12) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.3886(12) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3976(11) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.4833(12) ?
C8 C9 . 1.5284(11) ?
C9 C10 . 1.6262(11) ?
C10 C17 . 1.5295(11) ?
C10 C13 . 1.5462(11) ?
C11 C12 . 1.4859(11) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.5422(11) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C16 . 1.5268(12) ?
C14 C15 . 1.5270(12) ?
C14 H14A . 0.9800 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 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
_geom_hbond_publ_flag
C2 H2A O4 2_755 0.93 2.56 3.4353(11) 158 yes
C4 H4A O2 1_545 0.93 2.56 3.2878(11) 136 yes
C12 H12C O4 2_755 0.96 2.59 3.3600(11) 138 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
C6 C1 C2 C3 . . . . -0.47(12) ?
C9 C1 C2 C3 . . . . 175.68(7) ?
C1 C2 C3 C4 . . . . -0.65(13) ?
C2 C3 C4 C5 . . . . 1.05(13) ?
C3 C4 C5 C6 . . . . -0.31(12) ?
C2 C1 C6 C5 . . . . 1.20(12) ?
C9 C1 C6 C5 . . . . -174.97(7) ?
C2 C1 C6 C7 . . . . -177.48(7) ?
C9 C1 C6 C7 . . . . 6.35(11) ?
C4 C5 C6 C1 . . . . -0.81(12) ?
C4 C5 C6 C7 . . . . 177.91(7) ?
C8 N1 C7 O1 . . . . 179.82(8) ?
C19 N1 C7 O1 . . . . -8.22(12) ?
C8 N1 C7 C6 . . . . -2.85(12) ?
C19 N1 C7 C6 . . . . 169.11(7) ?
C1 C6 C7 O1 . . . . -174.64(8) ?
C5 C6 C7 O1 . . . . 6.66(13) ?
C1 C6 C7 N1 . . . . 8.11(11) ?
C5 C6 C7 N1 . . . . -170.60(7) ?
C7 N1 C8 O2 . . . . 168.43(8) ?
C19 N1 C8 O2 . . . . -3.69(11) ?
C7 N1 C8 C9 . . . . -16.05(11) ?
C19 N1 C8 C9 . . . . 171.82(7) ?
C11 O3 C9 C1 . . . . -114.79(7) ?
C11 O3 C9 C8 . . . . 122.21(7) ?
C11 O3 C9 C10 . . . . 5.96(8) ?
C2 C1 C9 O3 . . . . 40.97(9) ?
C6 C1 C9 O3 . . . . -142.90(7) ?
C2 C1 C9 C8 . . . . 159.89(7) ?
C6 C1 C9 C8 . . . . -23.97(10) ?
C2 C1 C9 C10 . . . . -72.42(9) ?
C6 C1 C9 C10 . . . . 103.71(8) ?
O2 C8 C9 O3 . . . . -35.81(10) ?
N1 C8 C9 O3 . . . . 148.68(7) ?
O2 C8 C9 C1 . . . . -156.00(7) ?
N1 C8 C9 C1 . . . . 28.49(9) ?
O2 C8 C9 C10 . . . . 74.70(9) ?
N1 C8 C9 C10 . . . . -100.81(8) ?
C11 N2 C10 C17 . . . . 122.44(7) ?
C11 N2 C10 C13 . . . . -117.25(7) ?
C11 N2 C10 C9 . . . . 6.03(8) ?
O3 C9 C10 N2 . . . . -7.21(7) ?
C1 C9 C10 N2 . . . . 110.20(7) ?
C8 C9 C10 N2 . . . . -120.67(7) ?
O3 C9 C10 C17 . . . . -124.22(6) ?
C1 C9 C10 C17 . . . . -6.82(9) ?
C8 C9 C10 C17 . . . . 122.32(7) ?
O3 C9 C10 C13 . . . . 113.04(7) ?
C1 C9 C10 C13 . . . . -129.55(7) ?
C8 C9 C10 C13 . . . . -0.41(9) ?
C10 N2 C11 O3 . . . . -2.63(10) ?
C10 N2 C11 C12 . . . . 177.58(8) ?
C9 O3 C11 N2 . . . . -2.67(10) ?
C9 O3 C11 C12 . . . . 177.15(7) ?
N2 C10 C13 C14 . . . . -72.97(8) ?
C17 C10 C13 C14 . . . . 48.05(9) ?
C9 C10 C13 C14 . . . . 170.96(6) ?
C10 C13 C14 C16 . . . . 71.60(9) ?
C10 C13 C14 C15 . . . . -165.79(7) ?
C18 O5 C17 O4 . . . . -5.16(12) ?
C18 O5 C17 C10 . . . . 174.99(7) ?
N2 C10 C17 O4 . . . . -5.43(11) ?
C13 C10 C17 O4 . . . . -126.69(8) ?
C9 C10 C17 O4 . . . . 107.03(9) ?
N2 C10 C17 O5 . . . . 174.42(6) ?
C13 C10 C17 O5 . . . . 53.16(8) ?
C9 C10 C17 O5 . . . . -73.12(8) ?
