# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
R.Pratap
; Department of Chemistry,
University of Delhi,
North Campus,
Delhi 110007,
India
;
R.Raghunandan
; Department of Chemsitry
Lucknow University
Lucknow-226 009
India
;
A.Kumar
; Department of Chemsitry
Lucknow University
Lucknow-226 009
India
;
V.Ram ''
#TrackingRef '9a_oxa.CIF'

_publ_contact_author             'Dr. Resmi Raghunandan'
_publ_contact_author_email       resmiraghu@rediffmail.com
_publ_contact_author_name        'Dr. Resmi Raghunandan'

data_8a
_database_code_depnum_ccdc_archive 'CCDC 838368'
#_journal_name_full nJc

_chemical_name_systematic        
;
5-Prop-2-ynylidene-6,7-dihydro-5H-1,4
-dioxa-benzo[g]cyclopenta[a]phenanthrene
;
_chemical_formula_sum            'C21 H13 N O2'
_chemical_formula_weight         311.32
_exptl_crystal_colour            yellow
_chemical_melting_point          203
_exptl_crystal_description       'rectangular block'
_exptl_crystal_preparation       
;
By slow evaporation from chloroform, methanol and acetone solution at RT.
;
_cell_length_a                   12.388(2)
_cell_length_b                   12.6450(1)
_cell_length_c                   10.535(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.90(2)
_cell_angle_gamma                90.00
_cell_volume                     1520.2(4)
_symmetry_space_group_name_H-M   'P 2(1)/c'

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'

_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.360
_diffrn_ambient_temperature      293(2)
_refine_ls_R_factor_all          0.2678
_refine_ls_R_factor_gt           0.1374
_refine_ls_wR_factor_ref         0.5108
_refine_ls_wR_factor_gt          0.3997

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.2580(11) -0.0788(11) 1.3469(12) 0.095(4) Uani 1 1 d . . .
H2 H 0.2693 -0.0925 1.4380 0.114 Uiso 1 1 calc R . .
C3 C 0.3355(9) -0.0219(9) 1.2996(11) 0.067(3) Uani 1 1 d . . .
H3 H 0.4093 0.0037 1.3548 0.081 Uiso 1 1 calc R . .
C5 C 0.4606(8) 0.1267(7) 1.0135(9) 0.047(2) Uani 1 1 d . . .
C6 C 0.4293(8) 0.1745(8) 0.7695(9) 0.061(3) Uani 1 1 d . . .
H6A H 0.5134 0.1639 0.8026 0.073 Uiso 1 1 calc R . .
H6B H 0.4150 0.2501 0.7653 0.073 Uiso 1 1 calc R . .
C7 C 0.3702(9) 0.1271(9) 0.6214(10) 0.071(3) Uani 1 1 d . . .
H7A H 0.3923 0.1668 0.5564 0.085 Uiso 1 1 calc R . .
H7B H 0.3927 0.0538 0.6201 0.085 Uiso 1 1 calc R . .
C8 C 0.1666(9) 0.1660(8) 0.4460(10) 0.068(3) Uani 1 1 d . . .
H8 H 0.1986 0.1754 0.3803 0.081 Uiso 1 1 calc R . .
C9 C 0.0450(10) 0.1798(8) 0.4146(12) 0.080(4) Uani 1 1 d . . .
H9 H -0.0043 0.2017 0.3268 0.096 Uiso 1 1 calc R . .
C10 C -0.0003(10) 0.1614(8) 0.5113(11) 0.067(3) Uani 1 1 d . . .
H10 H -0.0808 0.1673 0.4861 0.080 Uiso 1 1 calc R . .
C11 C 0.0690(8) 0.1343(8) 0.6460(11) 0.066(3) Uani 1 1 d . . .
H11 H 0.0367 0.1277 0.7118 0.079 Uiso 1 1 calc R . .
C12 C 0.1313(8) -0.0245(8) 0.8838(11) 0.066(3) Uani 1 1 d . . .
H12 H 0.0806 -0.0282 0.7917 0.079 Uiso 1 1 calc R . .
C13 C 0.1051(9) -0.0759(8) 0.9746(11) 0.066(3) Uani 1 1 d . . .
H13 H 0.0385 -0.1184 0.9468 0.079 Uiso 1 1 calc R . .
C14 C 0.5725(8) 0.1636(7) 1.0692(10) 0.063(3) Uani 1 1 d . . .
H14 H 0.6071 0.1886 1.0110 0.076 Uiso 1 1 calc R . .
C15 C 0.6371(8) 0.1648(8) 1.2122(11) 0.059(3) Uani 1 1 d . . .
C3A C 0.2821(8) -0.0117(7) 1.1584(9) 0.052(2) Uani 1 1 d . . .
C5A C 0.3862(8) 0.1272(7) 0.8670(10) 0.056(3) Uani 1 1 d . . .
C7A C 0.2370(9) 0.1366(8) 0.5856(12) 0.067(3) Uani 1 1 d . . .
C11A C 0.1924(8) 0.1165(7) 0.6818(10) 0.052(2) Uani 1 1 d . . .
C13A C 0.1766(9) -0.0673(9) 1.1130(10) 0.064(3) Uani 1 1 d . . .
C3B C 0.3091(7) 0.0381(7) 1.0629(10) 0.052(3) Uani 1 1 d . . .
C11B C 0.2730(7) 0.0936(7) 0.8255(10) 0.050(2) Uani 1 1 d . . .
C11C C 0.2368(7) 0.0383(7) 0.9209(11) 0.058(3) Uani 1 1 d . . .
N1 N 0.6865(7) 0.1671(8) 1.3303(9) 0.079(3) Uani 1 1 d . . .
O1 O 0.1614(6) -0.1097(6) 1.2282(8) 0.081(2) Uani 1 1 d . . .
O4 O 0.4190(5) 0.0880(5) 1.1056(7) 0.064(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.103(10) 0.092(10) 0.061(7) 0.009(7) 0.000(7) 0.039(8)
C3 0.057(6) 0.067(7) 0.078(8) -0.012(6) 0.026(6) -0.002(6)
C5 0.053(6) 0.039(5) 0.047(5) 0.011(4) 0.015(4) 0.003(4)
C6 0.053(6) 0.057(6) 0.063(6) 0.002(5) 0.011(5) -0.010(5)
C7 0.071(7) 0.054(6) 0.065(7) -0.009(5) 0.001(6) -0.003(5)
C8 0.073(7) 0.049(6) 0.061(7) 0.006(5) 0.004(6) 0.000(5)
C9 0.072(8) 0.052(6) 0.069(7) 0.007(6) -0.023(6) 0.002(6)
C10 0.060(6) 0.060(7) 0.054(6) 0.002(5) -0.007(5) 0.002(5)
C11 0.048(5) 0.049(6) 0.074(7) -0.007(5) -0.006(5) 0.005(5)
C12 0.048(6) 0.048(6) 0.084(7) 0.014(6) 0.006(5) -0.001(5)
C13 0.061(6) 0.053(6) 0.066(7) -0.010(5) 0.004(5) -0.010(5)
C14 0.043(5) 0.053(6) 0.068(7) 0.002(5) -0.005(5) 0.002(5)
C15 0.043(5) 0.049(6) 0.071(7) -0.017(5) 0.007(5) 0.000(4)
C3A 0.062(6) 0.044(5) 0.038(5) 0.001(5) 0.005(4) 0.005(5)
C5A 0.043(5) 0.039(5) 0.067(7) -0.003(5) 0.000(5) 0.003(4)
C7A 0.060(6) 0.044(6) 0.066(7) -0.006(5) -0.010(5) 0.006(5)
C11A 0.056(6) 0.043(5) 0.045(6) -0.005(5) 0.007(5) -0.002(5)
C13A 0.078(7) 0.059(7) 0.041(6) -0.002(5) 0.006(5) 0.006(6)
C3B 0.031(4) 0.039(5) 0.076(7) 0.005(5) 0.009(4) 0.005(4)
C11B 0.048(5) 0.032(5) 0.056(6) 0.014(4) 0.005(4) -0.008(4)
C11C 0.033(5) 0.032(5) 0.083(7) -0.013(5) -0.006(5) 0.005(4)
N1 0.059(5) 0.088(7) 0.063(6) -0.011(5) -0.005(5) -0.005(5)
O1 0.065(5) 0.077(5) 0.082(6) -0.002(4) 0.009(4) 0.006(4)
O4 0.047(4) 0.049(4) 0.064(4) -0.002(3) -0.014(3) -0.007(3)

_geom_special_details            
;
# All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.408(13) . ?
C2 C3 1.436(17) . ?
C2 H2 0.9300 . ?
C3 C3A 1.379(13) . ?
C3 H3 0.9300 . ?
C5 O4 1.354(11) . ?
C5 C14 1.360(12) . ?
C5 C5A 1.458(13) . ?
C6 C5A 1.458(14) . ?
C6 C7 1.563(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7A 1.548(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.423(16) . ?
C8 C7A 1.436(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.361(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(13) . ?
C10 H10 0.9300 . ?
C11 C11A 1.442(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.298(14) . ?
C12 C11C 1.446(13) . ?
C12 H12 0.9300 . ?
C13 C13A 1.385(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.405(14) . ?
C14 H14 0.9300 . ?
C15 N1 1.153(12) . ?
C3A C3B 1.336(13) . ?
C3A C13A 1.394(14) . ?
C5A C11B 1.364(12) . ?
C7A C11A 1.353(15) . ?
C11A C11B 1.481(12) . ?
C13A O1 1.405(12) . ?
C3B O4 1.406(10) . ?
C3B C11C 1.413(13) . ?
C11B C11C 1.433(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 C3 106.4(10) . . ?
O1 C2 H2 126.8 . . ?
C3 C2 H2 126.8 . . ?
C3A C3 C2 108.4(9) . . ?
C3A C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
O4 C5 C14 115.0(8) . . ?
O4 C5 C5A 120.0(8) . . ?
C14 C5 C5A 125.0(9) . . ?
C5A C6 C7 112.8(8) . . ?
C5A C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5A C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7A C7 C6 104.7(9) . . ?
C7A C7 H7A 110.8 . . ?
C6 C7 H7A 110.8 . . ?
C7A C7 H7B 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C7A 115.9(10) . . ?
C9 C8 H8 122.1 . . ?
C7A C8 H8 122.1 . . ?
C10 C9 C8 120.8(10) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 122.5(10) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C11A 118.6(11) . . ?
C10 C11 H11 120.7 . . ?
C11A C11 H11 120.7 . . ?
C13 C12 C11C 122.4(10) . . ?
C13 C12 H12 118.8 . . ?
C11C C12 H12 118.8 . . ?
C12 C13 C13A 119.7(10) . . ?
C12 C13 H13 120.2 . . ?
C13A C13 H13 120.2 . . ?
C5 C14 C15 121.7(10) . . ?
C5 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
N1 C15 C14 177.5(10) . . ?
C3B C3A C3 134.5(10) . . ?
C3B C3A C13A 117.1(9) . . ?
C3 C3A C13A 108.4(9) . . ?
C11B C5A C5 119.1(10) . . ?
C11B C5A C6 121.0(9) . . ?
C5 C5A C6 119.6(8) . . ?
C11A C7A C8 123.6(10) . . ?
C11A C7A C7 120.7(9) . . ?
C8 C7A C7 115.7(11) . . ?
C7A C11A C11 118.3(9) . . ?
C7A C11A C11B 119.5(9) . . ?
C11 C11A C11B 121.5(9) . . ?
C13 C13A C3A 122.1(10) . . ?
C13 C13A O1 129.3(10) . . ?
C3A C13A O1 108.6(8) . . ?
C3A C3B O4 117.8(9) . . ?
C3A C3B C11C 123.9(9) . . ?
O4 C3B C11C 118.3(9) . . ?
C5A C11B C11C 119.4(8) . . ?
C5A C11B C11A 117.8(9) . . ?
C11C C11B C11A 122.8(8) . . ?
C3B C11C C11B 120.1(8) . . ?
C3B C11C C12 114.7(10) . . ?
C11B C11C C12 125.1(9) . . ?
C13A O1 C2 108.0(9) . . ?
C5 O4 C3B 121.6(7) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C3A 4.9(12) . . . . ?
C5A C6 C7 C7A 52.4(11) . . . . ?
C7A C8 C9 C10 -2.6(15) . . . . ?
C8 C9 C10 C11 3.6(17) . . . . ?
C9 C10 C11 C11A -5.2(16) . . . . ?
C11C C12 C13 C13A 3.1(17) . . . . ?
O4 C5 C14 C15 -2.5(13) . . . . ?
C5A C5 C14 C15 177.2(9) . . . . ?
C5 C14 C15 N1 -42(27) . . . . ?
C2 C3 C3A C3B 175.0(11) . . . . ?
C2 C3 C3A C13A -4.4(12) . . . . ?
O4 C5 C5A C11B 3.6(13) . . . . ?
C14 C5 C5A C11B -176.1(9) . . . . ?
O4 C5 C5A C6 176.5(8) . . . . ?
C14 C5 C5A C6 -3.2(15) . . . . ?
C7 C6 C5A C11B -32.9(13) . . . . ?
C7 C6 C5A C5 154.3(8) . . . . ?
C9 C8 C7A C11A 3.8(15) . . . . ?
C9 C8 C7A C7 -177.0(9) . . . . ?
C6 C7 C7A C11A -40.0(13) . . . . ?
C6 C7 C7A C8 140.7(9) . . . . ?
C8 C7A C11A C11 -5.5(15) . . . . ?
C7 C7A C11A C11 175.4(9) . . . . ?
C8 C7A C11A C11B -176.0(9) . . . . ?
C7 C7A C11A C11B 4.8(14) . . . . ?
C10 C11 C11A C7A 6.0(14) . . . . ?
C10 C11 C11A C11B 176.3(9) . . . . ?
C12 C13 C13A C3A -5.4(17) . . . . ?
C12 C13 C13A O1 175.5(10) . . . . ?
C3B C3A C13A C13 3.4(15) . . . . ?
C3 C3A C13A C13 -177.1(10) . . . . ?
C3B C3A C13A O1 -177.3(8) . . . . ?
C3 C3A C13A O1 2.3(12) . . . . ?
C3 C3A C3B O4 5.2(17) . . . . ?
C13A C3A C3B O4 -175.4(8) . . . . ?
C3 C3A C3B C11C -178.7(10) . . . . ?
C13A C3A C3B C11C 0.7(15) . . . . ?
C5 C5A C11B C11C -13.2(13) . . . . ?
C6 C5A C11B C11C 174.0(9) . . . . ?
C5 C5A C11B C11A 166.8(8) . . . . ?
C6 C5A C11B C11A -6.0(13) . . . . ?
C7A C11A C11B C5A 21.5(13) . . . . ?
C11 C11A C11B C5A -148.7(9) . . . . ?
C7A C11A C11B C11C -158.5(9) . . . . ?
C11 C11A C11B C11C 31.3(14) . . . . ?
C3A C3B C11C C11B -179.7(9) . . . . ?
O4 C3B C11C C11B -3.6(13) . . . . ?
C3A C3B C11C C12 -2.7(14) . . . . ?
O4 C3B C11C C12 173.4(7) . . . . ?
C5A C11B C11C C3B 13.3(14) . . . . ?
C11A C11B C11C C3B -166.6(8) . . . . ?
C5A C11B C11C C12 -163.3(9) . . . . ?
C11A C11B C11C C12 16.7(15) . . . . ?
C13 C12 C11C C3B 0.7(14) . . . . ?
C13 C12 C11C C11B 177.5(10) . . . . ?
C13 C13A O1 C2 -179.9(11) . . . . ?
C3A C13A O1 C2 0.8(11) . . . . ?
C3 C2 O1 C13A -3.5(12) . . . . ?
C14 C5 O4 C3B -173.9(8) . . . . ?
C5A C5 O4 C3B 6.3(13) . . . . ?
C3A C3B O4 C5 170.2(8) . . . . ?
C11C C3B O4 C5 -6.2(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.150

#===END
_chemical_name_common            
;5-Prop-2-ynylidene-6,7-dihydro-5H-1,4 -dioxa-
benzo(g)cyclopenta(a)phenanthrene
;