#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/04/2230414.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_2230414
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
'Huang, Chengmei'
'Yu, Haitao'
_publ_section_title
;
 5-Methoxy-1,2',3-trimethyl-4,6-dioxa-2-azaspiro[bicyclo[3.2.0]hept-2-ene-7,4'-isoquinoline]-1',3'(2'H,4'H)-dione
;
_journal_coeditor_code           LH5241
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1340
_journal_page_last               o1341
_journal_paper_doi               10.1107/S1600536811016266
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H16 N2 O5'
_chemical_formula_moiety         'C16 H16 N2 O5'
_chemical_formula_sum            'C16 H16 N2 O5'
_chemical_formula_weight         316.31
_chemical_name_systematic
;
5-Methoxy-1,2',3-trimethyl-4,6-dioxa-2-azaspiro[bicyclo[3.2.0]hept-2-ene-
7,4'-isoquinoline]-1',3'(2'H,4'H)-dione
;
_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                 105.2940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.36430(10)
_cell_length_b                   29.8703(6)
_cell_length_c                   6.78020(10)
_cell_measurement_reflns_used    9541
_cell_measurement_temperature    100
_cell_measurement_theta_max      38.92
_cell_measurement_theta_min      2.73
_cell_volume                     1438.65(4)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            44501
_diffrn_reflns_theta_full        39.07
_diffrn_reflns_theta_max         39.07
_diffrn_reflns_theta_min         2.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_correction_T_min  0.9510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.374
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         8265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0485
_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)+(0.0561P)²+0.4048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                6842
_reflns_number_total             8265
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5241.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230414
_cod_database_fobs_code          2230414
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_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 0.98692(10) 0.07763(2) 1.21672(11) 0.01961(12) Uani d . 1 1 . .
O O2 0.97185(10) 0.22835(2) 1.29761(11) 0.02036(12) Uani d . 1 1 . .
O O3 0.64272(8) 0.074342(18) 0.93351(9) 0.01245(10) Uani d . 1 1 . .
O O4 0.80974(8) 0.037356(19) 0.72911(9) 0.01405(10) Uani d . 1 1 . .
O O5 0.50850(8) 0.06418(2) 0.59672(9) 0.01442(10) Uani d . 1 1 . .
N N1 0.99366(9) 0.15373(2) 1.23860(10) 0.01288(11) Uani d . 1 1 . .
N N2 0.98329(9) 0.10159(2) 0.78175(11) 0.01329(11) Uani d . 1 1 . .
C C1 0.91387(11) 0.11323(3) 1.15734(11) 0.01266(12) Uani d . 1 1 . .
C C2 0.89437(11) 0.19420(3) 1.22005(11) 0.01288(12) Uani d . 1 1 . .
C C3 0.68983(10) 0.19200(2) 1.11676(11) 0.01123(11) Uani d . 1 1 . .
C C4 0.57505(11) 0.22751(2) 1.14283(12) 0.01418(12) Uani d . 1 1 . .
H H4A 0.6279 0.2526 1.2171 0.017 Uiso calc R 1 1 . .
C C5 0.38157(12) 0.22526(3) 1.05764(13) 0.01604(13) Uani d . 1 1 . .
H H5A 0.3048 0.2489 1.0743 0.019 Uiso calc R 1 1 . .
C C6 0.30314(11) 0.18742(3) 0.94723(12) 0.01532(13) Uani d . 1 1 . .
H H6A 0.1739 0.1860 0.8893 0.018 Uiso calc R 1 1 . .
C C7 0.41660(11) 0.15171(3) 0.92290(11) 0.01323(12) Uani d . 1 1 . .
H H7A 0.3630 0.1264 0.8506 0.016 Uiso calc R 1 1 . .
C C8 0.61080(10) 0.15391(2) 1.00719(10) 0.01055(11) Uani d . 1 1 . .
C C9 0.73909(10) 0.11699(2) 0.97884(11) 0.01041(11) Uani d . 1 1 . .
C C10 0.67607(10) 0.07134(2) 0.73762(11) 0.01101(11) Uani d . 1 1 . .
C C11 0.98054(11) 0.05895(3) 0.76219(12) 0.01374(12) Uani d . 1 1 . .
C C12 0.79021(10) 0.11558(2) 0.76495(11) 0.01075(11) Uani d . 1 1 . .
C C13 0.72971(12) 0.15463(3) 0.62183(12) 0.01482(13) Uani d . 1 1 . .
H H13A 0.7495 0.1475 0.4909 0.022 Uiso calc R 1 1 . .
H H13B 0.8025 0.1806 0.6771 0.022 Uiso calc R 1 1 . .
H H13C 0.5986 0.1607 0.6063 0.022 Uiso calc R 1 1 . .
C C14 1.18102(12) 0.15176(3) 1.38319(13) 0.01961(15) Uani d . 1 1 . .
H H14A 1.2585 0.1311 1.3338 0.029 Uiso calc R 1 1 . .
H H14B 1.1695 0.1420 1.5143 0.029 Uiso calc R 1 1 . .
H H14C 1.2376 0.1809 1.3961 0.029 Uiso calc R 1 1 . .
C C15 0.51787(13) 0.05535(3) 0.39061(13) 0.02037(15) Uani d . 1 1 . .
H H15A 0.3927 0.0530 0.3024 0.031 Uiso calc R 1 1 . .
H H15B 0.5840 0.0278 0.3874 0.031 Uiso calc R 1 1 . .
H H15C 0.5831 0.0794 0.3447 0.031 Uiso calc R 1 1 . .
C C16 1.14282(12) 0.02931(3) 0.76728(17) 0.02177(17) Uani d . 1 1 . .
H H16A 1.2575 0.0462 0.8101 0.033 Uiso calc R 1 1 . .
H H16B 1.1314 0.0173 0.6333 0.033 Uiso calc R 1 1 . .
H H16C 1.1448 0.0053 0.8618 0.033 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
C10 O3 C9 . . 93.33(5) ?
C11 O4 C10 . . 105.68(6) ?
C10 O5 C15 . . 116.23(6) ?
C1 N1 C2 . . 123.91(6) ?
C1 N1 C14 . . 116.97(7) ?
C2 N1 C14 . . 118.08(7) ?
C11 N2 C12 . . 106.79(6) ?
O1 C1 N1 . . 121.77(7) ?
O1 C1 C9 . . 122.53(7) ?
N1 C1 C9 . . 115.52(6) ?
O2 C2 N1 . . 120.65(7) ?
O2 C2 C3 . . 122.79(7) ?
N1 C2 C3 . . 116.38(6) ?
C4 C3 C8 . . 120.27(7) ?
C4 C3 C2 . . 118.63(7) ?
C8 C3 C2 . . 120.95(6) ?
C5 C4 C3 . . 119.93(7) ?
C5 C4 H4A . . 120.0 ?
C3 C4 H4A . . 120.0 ?
C4 C5 C6 . . 119.74(7) ?
C4 C5 H5A . . 120.1 ?
C6 C5 H5A . . 120.1 ?
C7 C6 C5 . . 120.57(7) ?
C7 C6 H6A . . 119.7 ?
C5 C6 H6A . . 119.7 ?
C6 C7 C8 . . 119.88(7) ?
C6 C7 H7A . . 120.1 ?
C8 C7 H7A . . 120.1 ?
C7 C8 C3 . . 119.60(7) ?
C7 C8 C9 . . 121.75(6) ?
C3 C8 C9 . . 118.62(6) ?
O3 C9 C8 . . 112.58(6) ?
O3 C9 C1 . . 111.58(6) ?
C8 C9 C1 . . 112.49(6) ?
O3 C9 C12 . . 90.22(5) ?
C8 C9 C12 . . 116.44(6) ?
C1 C9 C12 . . 111.66(6) ?
O5 C10 O3 . . 108.56(6) ?
O5 C10 O4 . . 111.53(6) ?
O3 C10 O4 . . 112.06(6) ?
O5 C10 C12 . . 125.39(6) ?
O3 C10 C12 . . 93.25(5) ?
O4 C10 C12 . . 104.67(6) ?
N2 C11 O4 . . 118.12(7) ?
N2 C11 C16 . . 127.02(7) ?
O4 C11 C16 . . 114.85(7) ?
N2 C12 C13 . . 112.88(6) ?
N2 C12 C10 . . 104.58(6) ?
C13 C12 C10 . . 121.57(6) ?
N2 C12 C9 . . 113.37(6) ?
C13 C12 C9 . . 117.72(6) ?
C10 C12 C9 . . 83.13(5) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N1 C14 H14A . . 109.5 ?
N1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O5 C15 H15A . . 109.5 ?
O5 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O5 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C11 C16 H16A . . 109.5 ?
C11 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C11 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 C1 . 1.2116(10) ?
O2 C2 . 1.2183(9) ?
O3 C10 . 1.4158(9) ?
O3 C9 . 1.4512(9) ?
O4 C11 . 1.3784(9) ?
O4 C10 . 1.4257(9) ?
O5 C10 . 1.3636(9) ?
O5 C15 . 1.4416(10) ?
N1 C1 . 1.3933(10) ?
N1 C2 . 1.4012(10) ?
N1 C14 . 1.4679(10) ?
N2 C11 . 1.2799(10) ?
N2 C12 . 1.4574(10) ?
C1 C9 . 1.5206(10) ?
C2 C3 . 1.4857(10) ?
C3 C4 . 1.3961(10) ?
C3 C8 . 1.3990(10) ?
C4 C5 . 1.3907(12) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3941(12) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.3914(11) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.3946(10) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.4972(10) ?
C9 C12 . 1.5921(10) ?
C10 C12 . 1.5508(10) ?
C11 C16 . 1.4804(11) ?
C12 C13 . 1.5075(10) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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 . . . . -161.40(8) ?
C14 N1 C1 O1 . . . . 6.68(11) ?
C2 N1 C1 C9 . . . . 23.35(10) ?
C14 N1 C1 C9 . . . . -168.56(7) ?
C1 N1 C2 O2 . . . . 178.82(8) ?
C14 N1 C2 O2 . . . . 10.86(11) ?
C1 N1 C2 C3 . . . . 3.52(10) ?
C14 N1 C2 C3 . . . . -164.44(7) ?
O2 C2 C3 C4 . . . . -12.66(11) ?
N1 C2 C3 C4 . . . . 162.54(7) ?
O2 C2 C3 C8 . . . . 171.75(7) ?
N1 C2 C3 C8 . . . . -13.05(10) ?
C8 C3 C4 C5 . . . . -0.74(11) ?
C2 C3 C4 C5 . . . . -176.36(7) ?
C3 C4 C5 C6 . . . . 0.27(12) ?
C4 C5 C6 C7 . . . . 0.53(12) ?
C5 C6 C7 C8 . . . . -0.85(12) ?
C6 C7 C8 C3 . . . . 0.38(11) ?
C6 C7 C8 C9 . . . . -177.87(7) ?
C4 C3 C8 C7 . . . . 0.41(10) ?
C2 C3 C8 C7 . . . . 175.93(7) ?
C4 C3 C8 C9 . . . . 178.71(7) ?
C2 C3 C8 C9 . . . . -5.77(10) ?
C10 O3 C9 C8 . . . . 116.84(6) ?
C10 O3 C9 C1 . . . . -115.57(6) ?
C10 O3 C9 C12 . . . . -2.09(5) ?
C7 C8 C9 O3 . . . . -23.21(9) ?
C3 C8 C9 O3 . . . . 158.52(6) ?
C7 C8 C9 C1 . . . . -150.32(7) ?
C3 C8 C9 C1 . . . . 31.42(9) ?
C7 C8 C9 C12 . . . . 78.99(8) ?
C3 C8 C9 C12 . . . . -99.28(7) ?
O1 C1 C9 O3 . . . . 17.35(10) ?
N1 C1 C9 O3 . . . . -167.44(6) ?
O1 C1 C9 C8 . . . . 144.99(8) ?
N1 C1 C9 C8 . . . . -39.81(9) ?
O1 C1 C9 C12 . . . . -81.94(9) ?
N1 C1 C9 C12 . . . . 93.26(7) ?
C15 O5 C10 O3 . . . . -173.45(6) ?
C15 O5 C10 O4 . . . . -49.51(9) ?
C15 O5 C10 C12 . . . . 78.38(9) ?
C9 O3 C10 O5 . . . . -126.97(6) ?
C9 O3 C10 O4 . . . . 109.41(6) ?
C9 O3 C10 C12 . . . . 2.15(6) ?
C11 O4 C10 O5 . . . . 142.09(6) ?
C11 O4 C10 O3 . . . . -95.97(7) ?
C11 O4 C10 C12 . . . . 3.77(7) ?
C12 N2 C11 O4 . . . . 0.91(9) ?
C12 N2 C11 C16 . . . . 179.69(8) ?
C10 O4 C11 N2 . . . . -3.21(9) ?
C10 O4 C11 C16 . . . . 177.86(7) ?
C11 N2 C12 C13 . . . . -132.59(7) ?
C11 N2 C12 C10 . . . . 1.60(8) ?
C11 N2 C12 C9 . . . . 90.33(7) ?
O5 C10 C12 N2 . . . . -133.99(7) ?
O3 C10 C12 N2 . . . . 110.46(6) ?
O4 C10 C12 N2 . . . . -3.35(7) ?
O5 C10 C12 C13 . . . . -4.83(10) ?
O3 C10 C12 C13 . . . . -120.39(7) ?
O4 C10 C12 C13 . . . . 125.81(7) ?
O5 C10 C12 C9 . . . . 113.59(7) ?
O3 C10 C12 C9 . . . . -1.97(5) ?
O4 C10 C12 C9 . . . . -115.78(6) ?
O3 C9 C12 N2 . . . . -101.04(6) ?
C8 C9 C12 N2 . . . . 143.45(6) ?
C1 C9 C12 N2 . . . . 12.37(8) ?
O3 C9 C12 C13 . . . . 124.09(7) ?
C8 C9 C12 C13 . . . . 8.58(9) ?
C1 C9 C12 C13 . . . . -122.51(7) ?
O3 C9 C12 C10 . . . . 1.92(5) ?
C8 C9 C12 C10 . . . . -113.59(6) ?
C1 C9 C12 C10 . . . . 115.32(6) ?
