#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239434.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_2239434
loop_
_publ_author_name
'Raghuvarman, B.'
'Srinivasan, J.'
'Bakthadoss, M.'
'Aravindhan, S.'
_publ_section_title
;
 Methyl
 1-phenyl-3-p-tolyl-1,9b-dihydro-3H-chromeno[4,3-c]isoxazole-3a(4H)-carboxylate
;
_journal_coeditor_code           SU2676
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o281
_journal_page_last               o282
_journal_paper_doi               10.1107/S1600536814002438
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C25 H23 N O4'
_chemical_formula_moiety         'C25 H23 N O4'
_chemical_formula_sum            'C25 H23 N O4'
_chemical_formula_weight         401.44
_chemical_name_systematic
'Methyl 1-phenyl-3-p-tolyl-1,9b-dihydro-3H-chromeno[4,3-c]isoxazole-3a(4H)-carboxylate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 110.456(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0674(7)
_cell_length_b                   7.8105(4)
_cell_length_c                   19.7680(9)
_cell_measurement_reflns_used    3415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      1.55
_cell_volume                     2035.01(18)
_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)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18922
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.387
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0508
_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)+(0.0678P)²+0.5852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1509
_reflns_number_gt                3415
_reflns_number_total             5086
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2676sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2035.01(17)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2239434
_cod_database_fobs_code          2239434
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C C1 0.28173(13) 0.2285(2) 0.03324(9) 0.0428(4) Uani d . 1 1
C C2 0.21242(16) 0.2949(3) -0.03043(10) 0.0549(5) Uani d . 1 1
H H2 0.1432 0.2921 -0.0385 0.066 Uiso calc R 1 1
C C3 0.24774(18) 0.3646(3) -0.08108(10) 0.0641(6) Uani d . 1 1
H H3 0.2020 0.4092 -0.1236 0.077 Uiso calc R 1 1
C C4 0.35030(19) 0.3690(3) -0.06946(10) 0.0610(6) Uani d . 1 1
H H4 0.3737 0.4181 -0.1036 0.073 Uiso calc R 1 1
C C5 0.41795(16) 0.3000(2) -0.00667(10) 0.0499(5) Uani d . 1 1
H H5 0.4870 0.3013 0.0007 0.060 Uiso calc R 1 1
C C6 0.38480(13) 0.2284(2) 0.04573(9) 0.0396(4) Uani d . 1 1
C C7 0.46000(12) 0.1483(2) 0.11273(8) 0.0362(4) Uani d . 1 1
H H7 0.4920 0.0503 0.0983 0.043 Uiso calc R 1 1
C C8 0.41150(12) 0.0860(2) 0.16788(8) 0.0354(4) Uani d . 1 1
C C9 0.31056(13) 0.1770(2) 0.15550(9) 0.0433(4) Uani d . 1 1
H H9A 0.2788 0.1283 0.1874 0.052 Uiso calc R 1 1
H H9B 0.3234 0.2971 0.1677 0.052 Uiso calc R 1 1
C C10 0.49094(12) 0.1477(2) 0.24007(8) 0.0363(4) Uani d . 1 1
H H10 0.5482 0.0676 0.2548 0.044 Uiso calc R 1 1
C C11 0.64415(12) 0.2269(2) 0.16687(9) 0.0366(4) Uani d . 1 1
C C12 0.67274(15) 0.1419(2) 0.11511(10) 0.0486(4) Uani d . 1 1
H H12 0.6236 0.1026 0.0729 0.058 Uiso calc R 1 1
C C13 0.77511(17) 0.1158(3) 0.12682(13) 0.0592(6) Uani d . 1 1
H H13 0.7940 0.0584 0.0923 0.071 Uiso calc R 1 1
C C14 0.84856(16) 0.1735(3) 0.18855(13) 0.0594(5) Uani d . 1 1
H H14 0.9168 0.1567 0.1956 0.071 Uiso calc R 1 1
C C15 0.82042(14) 0.2561(3) 0.23968(12) 0.0544(5) Uani d . 1 1
H H15 0.8701 0.2944 0.2818 0.065 Uiso calc R 1 1
C C16 0.71910(13) 0.2836(2) 0.22953(10) 0.0435(4) Uani d . 1 1
H H16 0.7012 0.3401 0.2647 0.052 Uiso calc R 1 1
C C17 0.45771(12) 0.1822(2) 0.30376(8) 0.0387(4) Uani d . 1 1
C C18 0.43833(14) 0.3468(2) 0.32141(10) 0.0469(4) Uani d . 1 1
H H18 0.4412 0.4378 0.2919 0.056 Uiso calc R 1 1
C C19 0.41461(14) 0.3771(3) 0.38296(10) 0.0529(5) Uani d . 1 1
H H19 0.4031 0.4887 0.3946 0.063 Uiso calc R 1 1
C C20 0.40780(14) 0.2438(3) 0.42726(10) 0.0526(5) Uani d . 1 1
C C21 0.42430(16) 0.0803(3) 0.40799(10) 0.0591(5) Uani d . 1 1
H H21 0.4178 -0.0114 0.4361 0.071 Uiso calc R 1 1
C C22 0.45034(15) 0.0490(3) 0.34767(9) 0.0516(5) Uani d . 1 1
H H22 0.4630 -0.0626 0.3367 0.062 Uiso calc R 1 1
C C23 0.3852(2) 0.2806(4) 0.49513(12) 0.0751(7) Uani d . 1 1
H H23A 0.3697 0.1754 0.5142 0.113 Uiso calc R 1 1
H H23B 0.3282 0.3567 0.4840 0.113 Uiso calc R 1 1
H H23C 0.4433 0.3329 0.5303 0.113 Uiso calc R 1 1
C C24 0.39583(14) -0.1064(2) 0.16638(9) 0.0438(4) Uani d . 1 1
C C25 0.3720(2) -0.3606(3) 0.09983(16) 0.0832(8) Uani d . 1 1
H H25A 0.4320 -0.4181 0.1303 0.125 Uiso calc R 1 1
H H25B 0.3570 -0.3961 0.0507 0.125 Uiso calc R 1 1
H H25C 0.3161 -0.3891 0.1149 0.125 Uiso calc R 1 1
N N1 0.54050(10) 0.27177(18) 0.15286(7) 0.0368(3) Uani d . 1 1
O O1 0.24239(9) 0.16260(17) 0.08243(6) 0.0490(3) Uani d . 1 1
O O2 0.52327(8) 0.30692(14) 0.21877(6) 0.0401(3) Uani d . 1 1
O O3 0.3903(2) -0.1874(2) 0.21509(9) 0.1145(9) Uani d . 1 1
O O4 0.38844(14) -0.17740(17) 0.10527(8) 0.0697(5) 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 C6 121.96(15)
O1 C1 C2 116.73(16)
C6 C1 C2 121.31(17)
C3 C2 C1 119.17(19)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 120.76(18)
C2 C3 H3 119.6
C4 C3 H3 119.6
C3 C4 C5 119.41(19)
C3 C4 H4 120.3
C5 C4 H4 120.3
C4 C5 C6 121.32(19)
C4 C5 H5 119.3
C6 C5 H5 119.3
C1 C6 C5 118.01(16)
C1 C6 C7 121.70(15)
C5 C6 C7 120.26(16)
N1 C7 C6 111.58(13)
N1 C7 C8 105.54(12)
C6 C7 C8 113.59(13)
N1 C7 H7 108.7
C6 C7 H7 108.7
C8 C7 H7 108.7
C24 C8 C9 109.67(14)
C24 C8 C10 112.27(13)
C9 C8 C10 109.47(13)
C24 C8 C7 113.13(13)
C9 C8 C7 110.69(13)
C10 C8 C7 101.35(12)
O1 C9 C8 112.46(14)
O1 C9 H9A 109.1
C8 C9 H9A 109.1
O1 C9 H9B 109.1
C8 C9 H9B 109.1
H9A C9 H9B 107.8
O2 C10 C17 108.13(13)
O2 C10 C8 101.51(12)
C17 C10 C8 119.25(13)
O2 C10 H10 109.1
C17 C10 H10 109.1
C8 C10 H10 109.1
C16 C11 C12 118.91(16)
C16 C11 N1 119.98(14)
C12 C11 N1 120.78(15)
C13 C12 C11 119.71(18)
C13 C12 H12 120.1
C11 C12 H12 120.1
C14 C13 C12 120.97(18)
C14 C13 H13 119.5
C12 C13 H13 119.5
C15 C14 C13 119.32(18)
C15 C14 H14 120.3
C13 C14 H14 120.3
C14 C15 C16 121.0(2)
C14 C15 H15 119.5
C16 C15 H15 119.5
C15 C16 C11 120.13(17)
C15 C16 H16 119.9
C11 C16 H16 119.9
C22 C17 C18 118.46(16)
C22 C17 C10 120.09(16)
C18 C17 C10 121.39(15)
C17 C18 C19 120.50(18)
C17 C18 H18 119.7
C19 C18 H18 119.7
C20 C19 C18 121.11(19)
C20 C19 H19 119.4
C18 C19 H19 119.4
C21 C20 C19 117.84(17)
C21 C20 C23 122.1(2)
C19 C20 C23 120.1(2)
C20 C21 C22 121.52(19)
C20 C21 H21 119.2
C22 C21 H21 119.2
C17 C22 C21 120.52(19)
C17 C22 H22 119.7
C21 C22 H22 119.7
C20 C23 H23A 109.5
C20 C23 H23B 109.5
H23A C23 H23B 109.5
C20 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
O3 C24 O4 121.62(18)
O3 C24 C8 124.52(17)
O4 C24 C8 113.86(15)
O4 C25 H25A 109.5
O4 C25 H25B 109.5
H25A C25 H25B 109.5
O4 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
C11 N1 O2 110.86(12)
C11 N1 C7 118.62(13)
O2 N1 C7 105.67(11)
C1 O1 C9 112.99(13)
N1 O2 C10 105.79(11)
C24 O4 C25 116.71(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.376(2)
C1 C6 1.383(2)
C1 C2 1.395(2)
C2 C3 1.376(3)
C2 H2 0.9300
C3 C4 1.380(3)
C3 H3 0.9300
C4 C5 1.383(3)
C4 H4 0.9300
C5 C6 1.393(2)
C5 H5 0.9300
C6 C7 1.512(2)
C7 N1 1.488(2)
C7 C8 1.553(2)
C7 H7 0.9800
C8 C24 1.518(2)
C8 C9 1.529(2)
C8 C10 1.550(2)
C9 O1 1.432(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 O2 1.4368(19)
C10 C17 1.513(2)
C10 H10 0.9800
C11 C16 1.389(2)
C11 C12 1.392(2)
C11 N1 1.429(2)
C12 C13 1.391(3)
C12 H12 0.9300
C13 C14 1.371(3)
C13 H13 0.9300
C14 C15 1.369(3)
C14 H14 0.9300
C15 C16 1.385(2)
C15 H15 0.9300
C16 H16 0.9300
C17 C22 1.382(3)
C17 C18 1.384(2)
C18 C19 1.390(2)
C18 H18 0.9300
C19 C20 1.385(3)
C19 H19 0.9300
C20 C21 1.376(3)
C20 C23 1.511(3)
C21 C22 1.386(2)
C21 H21 0.9300
C22 H22 0.9300
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
C24 O3 1.178(2)
C24 O4 1.300(2)
C25 O4 1.447(2)
C25 H25A 0.9600
C25 H25B 0.9600
C25 H25C 0.9600
N1 O2 1.4326(16)
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 H2 Cg5 4_565 0.93 2.91 3.757(2) 151 yes
C25 H25B Cg3 1_545 0.96 2.71 3.450(3) 134 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
O1 C1 C2 C3 179.09(17)
C6 C1 C2 C3 -1.3(3)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 1.1(3)
C3 C4 C5 C6 -1.1(3)
O1 C1 C6 C5 -179.12(16)
C2 C1 C6 C5 1.2(3)
O1 C1 C6 C7 3.0(3)
C2 C1 C6 C7 -176.68(16)
C4 C5 C6 C1 -0.1(3)
C4 C5 C6 C7 177.88(17)
C1 C6 C7 N1 -125.26(16)
C5 C6 C7 N1 56.9(2)
C1 C6 C7 C8 -6.1(2)
C5 C6 C7 C8 176.00(15)
N1 C7 C8 C24 -134.90(14)
C6 C7 C8 C24 102.56(16)
N1 C7 C8 C9 101.55(15)
C6 C7 C8 C9 -20.99(18)
N1 C7 C8 C10 -14.50(15)
C6 C7 C8 C10 -137.04(14)
C24 C8 C9 O1 -72.08(17)
C10 C8 C9 O1 164.32(13)
C7 C8 C9 O1 53.43(18)
C24 C8 C10 O2 156.94(13)
C9 C8 C10 O2 -81.01(14)
C7 C8 C10 O2 35.94(14)
C24 C8 C10 C17 -84.50(19)
C9 C8 C10 C17 37.5(2)
C7 C8 C10 C17 154.50(15)
C16 C11 C12 C13 -0.2(3)
N1 C11 C12 C13 173.12(16)
C11 C12 C13 C14 -0.3(3)
C12 C13 C14 C15 0.8(3)
C13 C14 C15 C16 -0.7(3)
C14 C15 C16 C11 0.1(3)
C12 C11 C16 C15 0.3(3)
N1 C11 C16 C15 -173.06(16)
O2 C10 C17 C22 -161.69(15)
C8 C10 C17 C22 83.2(2)
O2 C10 C17 C18 15.5(2)
C8 C10 C17 C18 -99.61(19)
C22 C17 C18 C19 1.6(3)
C10 C17 C18 C19 -175.59(15)
C17 C18 C19 C20 -1.3(3)
C18 C19 C20 C21 -0.6(3)
C18 C19 C20 C23 178.06(19)
C19 C20 C21 C22 2.2(3)
C23 C20 C21 C22 -176.5(2)
C18 C17 C22 C21 -0.1(3)
C10 C17 C22 C21 177.14(17)
C20 C21 C22 C17 -1.8(3)
C9 C8 C24 O3 -80.1(3)
C10 C8 C24 O3 41.9(3)
C7 C8 C24 O3 155.8(2)
C9 C8 C24 O4 99.69(18)
C10 C8 C24 O4 -138.38(16)
C7 C8 C24 O4 -24.4(2)
C16 C11 N1 O2 -25.1(2)
C12 C11 N1 O2 161.65(14)
C16 C11 N1 C7 -147.58(15)
C12 C11 N1 C7 39.2(2)
C6 C7 N1 C11 -123.39(15)
C8 C7 N1 C11 112.79(15)
C6 C7 N1 O2 111.56(14)
C8 C7 N1 O2 -12.26(15)
C6 C1 O1 C9 29.8(2)
C2 C1 O1 C9 -150.52(16)
C8 C9 O1 C1 -58.64(19)
C11 N1 O2 C10 -92.54(14)
C7 N1 O2 C10 37.19(14)
C17 C10 O2 N1 -172.31(12)
C8 C10 O2 N1 -46.05(13)
O3 C24 O4 C25 0.6(3)
C8 C24 O4 C25 -179.18(19)
