#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/98/2229810.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_2229810
loop_
_publ_author_name
'Swaminathan, K.'
'Sethusankar, K.'
'Murugan, G.'
'Bakthadoss, M.'
_publ_section_title
;
 3-(3-Chlorophenyl)-1-methyl-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile
;
_journal_coeditor_code           RK2265
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o799
_journal_paper_doi               10.1107/S1600536811007495
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C18 H15 Cl N2 O2'
_chemical_formula_sum            'C18 H15 Cl N2 O2'
_chemical_formula_weight         326.77
_chemical_name_systematic
;
3-(3-Chlorophenyl)-1-methyl-3,3a,4,9b-tetrahydro-1H-
chromeno[4,3-c]isoxazole-3a-carbonitrile
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.354(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0141(4)
_cell_length_b                   9.2358(3)
_cell_length_c                   17.5945(6)
_cell_measurement_reflns_used    4926
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      0.998
_cell_volume                     1589.60(10)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_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      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20534
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.68
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9515
_exptl_absorpt_correction_T_min  0.9284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.632
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0512
_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)+(0.0641P)²+0.5250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                3390
_reflns_number_total             4926
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2265.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229810
_cod_database_fobs_code          2229810
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_disorder_assembly
_atom_site_disorder_group
C C1 0.71130(16) 0.55309(17) 0.60426(9) 0.0414(3) Uani d . 1 . .
C C2 0.7392(2) 0.5485(2) 0.53022(11) 0.0558(5) Uani d . 1 . .
H H2 0.6764 0.5081 0.4890 0.067 Uiso calc R 1 . .
C C3 0.8604(2) 0.6042(3) 0.51838(13) 0.0661(6) Uani d . 1 . .
H H3 0.8786 0.6031 0.4687 0.079 Uiso calc R 1 . .
C C4 0.9552(2) 0.6618(3) 0.57932(14) 0.0666(6) Uani d . 1 . .
H H4 1.0375 0.6980 0.5710 0.080 Uiso calc R 1 . .
C C5 0.92754(19) 0.6654(2) 0.65242(12) 0.0527(4) Uani d . 1 . .
H H5 0.9924 0.7029 0.6936 0.063 Uiso calc R 1 . .
C C6 0.80402(15) 0.61383(17) 0.66604(9) 0.0391(3) Uani d . 1 . .
C C7 0.77527(14) 0.61740(15) 0.74613(8) 0.0347(3) Uani d . 1 . .
H H7 0.8576 0.5912 0.7847 0.042 Uiso calc R 1 . .
C C8 0.65603(14) 0.51912(15) 0.75457(8) 0.0345(3) Uani d . 1 . .
C C9 0.54349(15) 0.53043(18) 0.68020(9) 0.0400(3) Uani d . 1 . .
H H9A 0.4677 0.4683 0.6851 0.048 Uiso calc R 1 . .
H H9B 0.5100 0.6292 0.6743 0.048 Uiso calc R 1 . .
C C10 0.60629(16) 0.58987(17) 0.82461(9) 0.0392(3) Uani d . 1 . .
H H10 0.5095 0.6157 0.8079 0.047 Uiso calc R 1 . .
C C11 0.62489(15) 0.49933(17) 0.89708(9) 0.0382(3) Uani d . 1 . .
C C12 0.74430(16) 0.50552(19) 0.95373(10) 0.0435(4) Uani d . 1 . .
H H12 0.8145 0.5681 0.9483 0.052 Uiso calc R 1 . .
C C13 0.75772(19) 0.4174(2) 1.01837(10) 0.0503(4) Uani d . 1 . .
C C14 0.6564(2) 0.3247(2) 1.02857(12) 0.0584(5) Uani d . 1 . .
H H14 0.6676 0.2664 1.0726 0.070 Uiso calc R 1 . .
C C15 0.5385(2) 0.3195(2) 0.97269(12) 0.0621(5) Uani d . 1 . .
H H15 0.4687 0.2569 0.9788 0.075 Uiso calc R 1 . .
C C16 0.52159(19) 0.4062(2) 0.90713(11) 0.0512(4) Uani d . 1 . .
H H16 0.4406 0.4020 0.8697 0.061 Uiso calc R 1 . .
C C17 0.8261(2) 0.86941(19) 0.78734(11) 0.0531(4) Uani d . 1 . .
H H17A 0.7878 0.9520 0.8080 0.080 Uiso calc R 1 . .
H H17B 0.8582 0.8975 0.7418 0.080 Uiso calc R 1 . .
H H17C 0.9010 0.8321 0.8257 0.080 Uiso calc R 1 . .
C C18 0.69897(16) 0.36725(17) 0.76710(10) 0.0405(3) Uani d . 1 . .
N N1 0.72137(14) 0.75768(14) 0.76661(7) 0.0396(3) Uani d . 1 . .
N N2 0.72938(17) 0.24949(17) 0.77403(11) 0.0618(4) Uani d . 1 . .
O O1 0.59142(12) 0.48990(13) 0.61273(7) 0.0470(3) Uani d . 1 . .
O O2 0.68515(14) 0.71908(12) 0.84078(7) 0.0481(3) Uani d . 1 . .
Cl Cl1 0.90798(6) 0.42666(9) 1.08998(4) 0.0900(2) Uani 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'
Cl Cl 0.1484 0.1585 '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
O1 C1 C6 . . 122.77(14) ?
O1 C1 C2 . . 116.42(15) ?
C6 C1 C2 . . 120.75(17) ?
C3 C2 C1 . . 119.44(19) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 120.68(19) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C5 C4 C3 . . 119.7(2) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 C6 . . 121.15(19) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C1 C6 C5 . . 118.25(16) ?
C1 C6 C7 . . 120.97(14) ?
C5 C6 C7 . . 120.71(15) ?
N1 C7 C6 . . 113.74(12) ?
N1 C7 C8 . . 99.38(11) ?
C6 C7 C8 . . 112.88(12) ?
N1 C7 H7 . . 110.1 ?
C6 C7 H7 . . 110.1 ?
C8 C7 H7 . . 110.1 ?
C18 C8 C7 . . 111.76(12) ?
C18 C8 C9 . . 109.29(12) ?
C7 C8 C9 . . 108.78(12) ?
C18 C8 C10 . . 114.32(13) ?
C7 C8 C10 . . 102.39(11) ?
C9 C8 C10 . . 110.04(12) ?
O1 C9 C8 . . 112.07(12) ?
O1 C9 H9A . . 109.2 ?
C8 C9 H9A . . 109.2 ?
O1 C9 H9B . . 109.2 ?
C8 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
O2 C10 C11 . . 109.49(12) ?
O2 C10 C8 . . 104.48(12) ?
C11 C10 C8 . . 115.63(12) ?
O2 C10 H10 . . 109.0 ?
C11 C10 H10 . . 109.0 ?
C8 C10 H10 . . 109.0 ?
C12 C11 C16 . . 119.17(16) ?
C12 C11 C10 . . 121.27(14) ?
C16 C11 C10 . . 119.56(15) ?
C13 C12 C11 . . 119.03(16) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C14 C13 C12 . . 122.17(17) ?
C14 C13 Cl1 . . 118.99(15) ?
C12 C13 Cl1 . . 118.84(14) ?
C15 C14 C13 . . 118.59(17) ?
C15 C14 H14 . . 120.7 ?
C13 C14 H14 . . 120.7 ?
C14 C15 C16 . . 120.76(17) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C15 C16 C11 . . 120.27(17) ?
C15 C16 H16 . . 119.9 ?
C11 C16 H16 . . 119.9 ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N2 C18 C8 . . 177.46(19) ?
C17 N1 O2 . . 104.46(12) ?
C17 N1 C7 . . 113.60(13) ?
O2 N1 C7 . . 100.14(10) ?
C1 O1 C9 . . 115.99(12) ?
C10 O2 N1 . . 104.90(11) ?
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
C1 O1 . 1.371(2) ?
C1 C6 . 1.388(2) ?
C1 C2 . 1.390(2) ?
C2 C3 . 1.375(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.393(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.498(2) ?
C7 N1 . 1.4775(19) ?
C7 C8 . 1.532(2) ?
C7 H7 . 0.9800 ?
C8 C18 . 1.470(2) ?
C8 C9 . 1.537(2) ?
C8 C10 . 1.567(2) ?
C9 O1 . 1.423(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O2 . 1.4257(19) ?
C10 C11 . 1.503(2) ?
C10 H10 . 0.9800 ?
C11 C12 . 1.384(2) ?
C11 C16 . 1.385(2) ?
C12 C13 . 1.381(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.369(3) ?
C13 Cl1 . 1.7459(19) ?
C14 C15 . 1.366(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.385(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 N1 . 1.461(2) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 N2 . 1.129(2) ?
N1 O2 . 1.4711(17) ?
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
O1 C1 C2 C3 . . . . -177.20(17) ?
C6 C1 C2 C3 . . . . 0.3(3) ?
C1 C2 C3 C4 . . . . 1.3(3) ?
C2 C3 C4 C5 . . . . -0.9(3) ?
C3 C4 C5 C6 . . . . -1.0(3) ?
O1 C1 C6 C5 . . . . 175.18(15) ?
C2 C1 C6 C5 . . . . -2.2(2) ?
O1 C1 C6 C7 . . . . -1.9(2) ?
C2 C1 C6 C7 . . . . -179.23(15) ?
C4 C5 C6 C1 . . . . 2.5(3) ?
C4 C5 C6 C7 . . . . 179.59(17) ?
C1 C6 C7 N1 . . . . -98.81(17) ?
C5 C6 C7 N1 . . . . 84.21(18) ?
C1 C6 C7 C8 . . . . 13.4(2) ?
C5 C6 C7 C8 . . . . -163.53(14) ?
N1 C7 C8 C18 . . . . -158.11(12) ?
C6 C7 C8 C18 . . . . 81.06(15) ?
N1 C7 C8 C9 . . . . 81.13(13) ?
C6 C7 C8 C9 . . . . -39.70(16) ?
N1 C7 C8 C10 . . . . -35.30(13) ?
C6 C7 C8 C10 . . . . -156.14(12) ?
C18 C8 C9 O1 . . . . -63.51(17) ?
C7 C8 C9 O1 . . . . 58.76(16) ?
C10 C8 C9 O1 . . . . 170.19(12) ?
C18 C8 C10 O2 . . . . 127.25(13) ?
C7 C8 C10 O2 . . . . 6.19(14) ?
C9 C8 C10 O2 . . . . -109.34(13) ?
C18 C8 C10 C11 . . . . 6.83(18) ?
C7 C8 C10 C11 . . . . -114.23(14) ?
C9 C8 C10 C11 . . . . 130.25(14) ?
O2 C10 C11 C12 . . . . -28.6(2) ?
C8 C10 C11 C12 . . . . 89.10(18) ?
O2 C10 C11 C16 . . . . 152.35(14) ?
C8 C10 C11 C16 . . . . -89.99(18) ?
C16 C11 C12 C13 . . . . 0.7(2) ?
C10 C11 C12 C13 . . . . -178.38(15) ?
C11 C12 C13 C14 . . . . -0.4(3) ?
C11 C12 C13 Cl1 . . . . -179.51(13) ?
C12 C13 C14 C15 . . . . 0.1(3) ?
Cl1 C13 C14 C15 . . . . 179.19(15) ?
C13 C14 C15 C16 . . . . -0.1(3) ?
C14 C15 C16 C11 . . . . 0.4(3) ?
C12 C11 C16 C15 . . . . -0.7(3) ?
C10 C11 C16 C15 . . . . 178.42(16) ?
C6 C7 N1 C17 . . . . -77.41(16) ?
C8 C7 N1 C17 . . . . 162.38(12) ?
C6 C7 N1 O2 . . . . 171.80(12) ?
C8 C7 N1 O2 . . . . 51.59(12) ?
C6 C1 O1 C9 . . . . 20.4(2) ?
C2 C1 O1 C9 . . . . -162.18(15) ?
C8 C9 O1 C1 . . . . -49.34(18) ?
C11 C10 O2 N1 . . . . 150.44(12) ?
C8 C10 O2 N1 . . . . 26.01(14) ?
C17 N1 O2 C10 . . . . -167.72(13) ?
C7 N1 O2 C10 . . . . -49.94(13) ?
