#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/79/2237902.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_2237902
loop_
_publ_author_name
'Paramasivam, S.'
'Srinivasan, J.'
'Seshadri, P. R.'
'Bakthadoss, M.'
_publ_section_title
;
 rac-Methyl
 3-(2-methoxyphenyl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carboxylate
;
_journal_coeditor_code           IS5259
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o664
_journal_paper_doi               10.1107/S1600536813008635
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C19 H17 N O5'
_chemical_formula_moiety         'C19 H17 N O5'
_chemical_formula_sum            'C19 H17 N O5'
_chemical_formula_weight         339.34
_chemical_name_systematic
'rac-Methyl 3-(2-methoxyphenyl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-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                81.308(2)
_cell_angle_beta                 67.801(2)
_cell_angle_gamma                69.085(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4804(4)
_cell_length_b                   9.6401(4)
_cell_length_c                   10.7013(5)
_cell_measurement_reflns_used    3462
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.06
_cell_volume                     845.71(7)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII area-detector'
_diffrn_measurement_method       'ω and φ 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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12631
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.185
_refine_ls_extinction_coef       0.093(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0400
_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)+(0.0548P)²+0.1820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                3012
_reflns_number_total             3462
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5259.cif
_cod_data_source_block           I
_cod_original_cell_volume        845.71(6)
_cod_database_code               2237902
_cod_database_fobs_code          2237902
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
C C1 0.76808(16) 0.07314(16) 0.63411(13) 0.0495(3) Uani d . 1 1
C C2 0.7901(2) -0.0399(2) 0.55433(17) 0.0684(5) Uani d . 1 1
H H2 0.8490 -0.1376 0.5680 0.082 Uiso calc R 1 1
C C3 0.7231(2) -0.0043(3) 0.4548(2) 0.0868(7) Uani d . 1 1
H H3 0.7355 -0.0791 0.4021 0.104 Uiso calc R 1 1
C C4 0.6378(3) 0.1410(3) 0.4322(2) 0.0881(6) Uani d . 1 1
H H4 0.5961 0.1633 0.3630 0.106 Uiso calc R 1 1
C C5 0.6143(2) 0.2526(2) 0.51121(16) 0.0660(4) Uani d . 1 1
H H5 0.5564 0.3500 0.4957 0.079 Uiso calc R 1 1
C C6 0.67764(16) 0.21950(16) 0.61527(13) 0.0471(3) Uani d . 1 1
C C7 0.65159(14) 0.32946(14) 0.70800(12) 0.0408(3) Uani d . 1 1
C C8 0.70310(13) 0.27662(13) 0.82869(12) 0.0364(3) Uani d . 1 1
C C9 0.86085(15) 0.14797(14) 0.78248(14) 0.0441(3) Uani d . 1 1
H H9A 0.9423 0.1821 0.7119 0.053 Uiso calc R 1 1
H H9B 0.8986 0.1103 0.8575 0.053 Uiso calc R 1 1
C C10 0.57037(15) 0.22930(13) 0.94184(12) 0.0402(3) Uani d . 1 1
C C11 0.5050(2) 0.09585(19) 1.14593(15) 0.0660(4) Uani d . 1 1
H H11A 0.4436 0.1773 1.2068 0.099 Uiso calc R 1 1
H H11B 0.5573 0.0116 1.1917 0.099 Uiso calc R 1 1
H H11C 0.4343 0.0707 1.1153 0.099 Uiso calc R 1 1
C C12 0.70663(14) 0.42463(13) 0.86467(12) 0.0385(3) Uani d . 1 1
H H12 0.6616 0.4354 0.9629 0.046 Uiso calc R 1 1
C C13 0.87197(14) 0.44101(14) 0.81075(13) 0.0410(3) Uani d . 1 1
C C14 0.92427(19) 0.51937(18) 0.69297(15) 0.0559(4) Uani d . 1 1
H H14 0.8557 0.5657 0.6447 0.067 Uiso calc R 1 1
C C15 1.0783(2) 0.5294(2) 0.64626(18) 0.0781(5) Uani d . 1 1
H H15 1.1132 0.5817 0.5667 0.094 Uiso calc R 1 1
C C16 1.1786(2) 0.4619(3) 0.7180(2) 0.0845(6) Uani d . 1 1
H H16 1.2815 0.4692 0.6866 0.101 Uiso calc R 1 1
C C17 1.12966(19) 0.3833(2) 0.8361(2) 0.0708(5) Uani d . 1 1
H H17 1.1990 0.3378 0.8837 0.085 Uiso calc R 1 1
C C18 0.97535(16) 0.37288(15) 0.88296(15) 0.0493(3) Uani d . 1 1
C C19 1.0138(3) 0.2223(2) 1.0745(2) 0.0877(6) Uani d . 1 1
H H19A 1.1042 0.1442 1.0219 0.132 Uiso calc R 1 1
H H19B 0.9531 0.1807 1.1551 0.132 Uiso calc R 1 1
H H19C 1.0517 0.2909 1.0983 0.132 Uiso calc R 1 1
N N1 0.59522(14) 0.47046(13) 0.69528(12) 0.0500(3) Uani d . 1 1
O O1 0.83574(12) 0.03193(10) 0.73258(10) 0.0533(3) Uani d . 1 1
O O2 0.59926(11) 0.53548(10) 0.80421(10) 0.0503(3) Uani d . 1 1
O O3 0.43272(12) 0.27371(14) 0.94996(11) 0.0638(3) Uani d . 1 1
O O4 0.62574(12) 0.13826(11) 1.03084(10) 0.0543(3) Uani d . 1 1
O O5 0.91320(14) 0.29842(12) 0.99727(11) 0.0631(3) Uani d . 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
O1 C1 C2 116.64(14)
O1 C1 C6 122.61(12)
C2 C1 C6 120.73(15)
C3 C2 C1 118.83(18)
C3 C2 H2 120.6
C1 C2 H2 120.6
C2 C3 C4 120.97(17)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C4 C3 120.49(18)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 119.91(19)
C4 C5 H5 120.0
C6 C5 H5 120.0
C1 C6 C5 119.02(14)
C1 C6 C7 117.43(12)
C5 C6 C7 123.53(14)
N1 C7 C6 126.69(12)
N1 C7 C8 114.75(11)
C6 C7 C8 118.48(11)
C7 C8 C9 106.98(10)
C7 C8 C10 109.18(9)
C9 C8 C10 112.00(10)
C7 C8 C12 99.03(9)
C9 C8 C12 118.65(10)
C10 C8 C12 109.87(9)
O1 C9 C8 109.50(10)
O1 C9 H9A 109.8
C8 C9 H9A 109.8
O1 C9 H9B 109.8
C8 C9 H9B 109.8
H9A C9 H9B 108.2
O3 C10 O4 124.43(12)
O3 C10 C8 123.42(12)
O4 C10 C8 112.11(10)
O4 C11 H11A 109.5
O4 C11 H11B 109.5
H11A C11 H11B 109.5
O4 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O2 C12 C13 110.92(10)
O2 C12 C8 102.91(9)
C13 C12 C8 114.29(10)
O2 C12 H12 109.5
C13 C12 H12 109.5
C8 C12 H12 109.5
C14 C13 C18 119.30(12)
C14 C13 C12 122.56(12)
C18 C13 C12 118.14(11)
C13 C14 C15 120.48(16)
C13 C14 H14 119.8
C15 C14 H14 119.8
C16 C15 C14 119.62(16)
C16 C15 H15 120.2
C14 C15 H15 120.2
C15 C16 C17 121.24(15)
C15 C16 H16 119.4
C17 C16 H16 119.4
C16 C17 C18 119.23(16)
C16 C17 H17 120.4
C18 C17 H17 120.4
O5 C18 C17 124.89(14)
O5 C18 C13 114.98(12)
C17 C18 C13 120.13(15)
O5 C19 H19A 109.5
O5 C19 H19B 109.5
H19A C19 H19B 109.5
O5 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C7 N1 O2 107.98(10)
C1 O1 C9 116.02(10)
N1 O2 C12 108.84(9)
C10 O4 C11 115.35(12)
C18 O5 C19 118.13(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3718(17)
C1 C2 1.394(2)
C1 C6 1.395(2)
C2 C3 1.379(3)
C2 H2 0.9300
C3 C4 1.382(3)
C3 H3 0.9300
C4 C5 1.372(3)
C4 H4 0.9300
C5 C6 1.402(2)
C5 H5 0.9300
C6 C7 1.4544(19)
C7 N1 1.2775(17)
C7 C8 1.5053(16)
C8 C9 1.5237(16)
C8 C10 1.5327(16)
C8 C12 1.5476(16)
C9 O1 1.4352(16)
C9 H9A 0.9700
C9 H9B 0.9700
C10 O3 1.1918(15)
C10 O4 1.3225(15)
C11 O4 1.4531(17)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 O2 1.4521(15)
C12 C13 1.5102(16)
C12 H12 0.9800
C13 C14 1.3829(19)
C13 C18 1.3959(18)
C14 C15 1.388(2)
C14 H14 0.9300
C15 C16 1.370(3)
C15 H15 0.9300
C16 C17 1.380(3)
C16 H16 0.9300
C17 C18 1.392(2)
C17 H17 0.9300
C18 O5 1.3604(18)
C19 O5 1.4296(19)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
N1 O2 1.4229(15)
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
C17 H17 O3 1_655 0.93 2.42 3.3084(19) 159
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
O1 C1 C2 C3 179.39(14)
C6 C1 C2 C3 1.0(2)
C1 C2 C3 C4 1.1(3)
C2 C3 C4 C5 -1.8(3)
C3 C4 C5 C6 0.3(3)
O1 C1 C6 C5 179.24(12)
C2 C1 C6 C5 -2.5(2)
O1 C1 C6 C7 -2.07(18)
C2 C1 C6 C7 176.20(12)
C4 C5 C6 C1 1.8(2)
C4 C5 C6 C7 -176.77(15)
C1 C6 C7 N1 168.16(12)
C5 C6 C7 N1 -13.2(2)
C1 C6 C7 C8 -8.22(17)
C5 C6 C7 C8 170.40(12)
N1 C7 C8 C9 -138.72(11)
C6 C7 C8 C9 38.09(14)
N1 C7 C8 C10 99.88(12)
C6 C7 C8 C10 -83.31(13)
N1 C7 C8 C12 -14.94(13)
C6 C7 C8 C12 161.87(10)
C7 C8 C9 O1 -59.44(13)
C10 C8 C9 O1 60.16(13)
C12 C8 C9 O1 -170.16(10)
C7 C8 C10 O3 -23.21(17)
C9 C8 C10 O3 -141.51(13)
C12 C8 C10 O3 84.40(15)
C7 C8 C10 O4 158.97(10)
C9 C8 C10 O4 40.67(14)
C12 C8 C10 O4 -93.43(12)
C7 C8 C12 O2 22.79(11)
C9 C8 C12 O2 137.86(11)
C10 C8 C12 O2 -91.49(11)
C7 C8 C12 C13 -97.56(11)
C9 C8 C12 C13 17.51(15)
C10 C8 C12 C13 148.16(10)
O2 C12 C13 C14 -17.90(17)
C8 C12 C13 C14 97.88(15)
O2 C12 C13 C18 162.62(11)
C8 C12 C13 C18 -81.60(14)
C18 C13 C14 C15 0.5(2)
C12 C13 C14 C15 -178.98(14)
C13 C14 C15 C16 -0.4(3)
C14 C15 C16 C17 0.3(3)
C15 C16 C17 C18 -0.1(3)
C16 C17 C18 O5 179.75(16)
C16 C17 C18 C13 0.2(2)
C14 C13 C18 O5 -179.97(12)
C12 C13 C18 O5 -0.47(18)
C14 C13 C18 C17 -0.4(2)
C12 C13 C18 C17 179.12(13)
C6 C7 N1 O2 -176.52(11)
C8 C7 N1 O2 -0.02(14)
C2 C1 O1 C9 159.71(12)
C6 C1 O1 C9 -21.95(17)
C8 C9 O1 C1 53.68(14)
C7 N1 O2 C12 16.69(13)
C13 C12 O2 N1 97.46(11)
C8 C12 O2 N1 -25.18(12)
O3 C10 O4 C11 -1.54(19)
C8 C10 O4 C11 176.26(11)
C17 C18 O5 C19 -1.3(2)
C13 C18 O5 C19 178.27(14)
