#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:59:10 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180525 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/94/7219448.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7219448
loop_
_publ_author_name
'Pramanik, Animesh'
'Pathak, Sudipta'
'Das, Doyel'
'Kundu, Ashis'
'Maity, Subhendu'
'Guchhait, Nikhil'
_publ_section_title
;
 Synthesis of 4-Hydroxyindole Fused Isocoumarin Derivatives and Their
 Fluorescence “Turn-Off” Sensing Cu(II) Ions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA01060H
_journal_year                    2015
_chemical_formula_sum            'C28 H24 N2 O3'
_chemical_formula_weight         436.49
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-11-27 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.072(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            7
_cell_length_a                   20.4475(13)
_cell_length_b                   14.4995(10)
_cell_length_c                   13.9270(9)
_cell_measurement_temperature    293(2)
_cell_volume                     3967.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24613
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1610
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0438
_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)+(0.0571P)²+0.4461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                2909
_reflns_number_total             4530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra01060h2.cif
_cod_data_source_block           sp1
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7219448
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O2 O 0.77237(5) 0.36541(7) 0.81889(7) 0.0504(3) Uani 1 1 d .
N1 N 0.74891(6) 0.46711(8) 1.03806(8) 0.0430(3) Uani 1 1 d .
O1 O 0.73583(7) 0.24200(9) 0.72878(9) 0.0778(4) Uani 1 1 d .
O3 O 0.88178(6) 0.51847(8) 0.82636(9) 0.0665(3) Uani 1 1 d .
C1 C 0.73324(7) 0.39949(10) 0.96320(9) 0.0418(3) Uani 1 1 d .
C15 C 0.79507(7) 0.52592(10) 1.01876(10) 0.0447(3) Uani 1 1 d .
C7 C 0.68521(7) 0.27016(10) 0.86037(10) 0.0476(4) Uani 1 1 d .
C10 C 0.81148(7) 0.49819(10) 0.93275(10) 0.0450(3) Uani 1 1 d .
C2 C 0.68543(7) 0.32466(9) 0.94467(10) 0.0435(3) Uani 1 1 d .
C17 C 0.66169(7) 0.51532(10) 1.12400(11) 0.0459(3) Uani 1 1 d .
C3 C 0.63944(8) 0.30160(11) 0.99910(12) 0.0525(4) Uani 1 1 d .
C9 C 0.77225(7) 0.41823(10) 0.90058(9) 0.0431(3) Uani 1 1 d .
C16 C 0.72857(8) 0.46875(12) 1.13070(10) 0.0459(3) Uani 1 1 d .
C22 C 0.63799(8) 0.51238(13) 1.20776(13) 0.0597(4) Uani 1 1 d .
C11 C 0.86434(8) 0.54360(11) 0.89983(11) 0.0523(4) Uani 1 1 d .
C8 C 0.73101(8) 0.28884(11) 0.79791(11) 0.0532(4) Uani 1 1 d .
C14 C 0.82422(10) 0.60735(12) 1.08033(12) 0.0577(4) Uani 1 1 d .
C6 C 0.64012(9) 0.19612(11) 0.83363(13) 0.0586(4) Uani 1 1 d .
C26 C 0.5000 0.85964(17) 0.7500 0.0573(6) Uani 1 2 d S
N2 N 0.5000 0.95439(17) 0.7500 0.0874(8) Uani 1 2 d S
C18 C 0.62511(9) 0.56278(13) 1.04160(15) 0.0701(5) Uani 1 1 d .
C5 C 0.59632(8) 0.22738(12) 0.97185(13) 0.0610(4) Uani 1 1 d .
C4 C 0.59631(9) 0.17467(12) 0.88911(14) 0.0648(5) Uani 1 1 d .
C25 C 0.54789(9) 0.81094(14) 0.71649(12) 0.0653(5) Uani 1 1 d .
C13 C 0.85378(12) 0.67278(13) 1.01781(15) 0.0720(5) Uani 1 1 d .
C21 C 0.57967(10) 0.55799(15) 1.21036(18) 0.0785(6) Uani 1 1 d .
C12 C 0.89870(11) 0.62338(16) 0.96414(16) 0.0741(5) Uani 1 1 d .
C19 C 0.56522(11) 0.60807(16) 1.0444(2) 0.0937(7) Uani 1 1 d .
C24 C 0.54719(14) 0.71646(16) 0.71712(16) 0.0903(7) Uani 1 1 d .
C20 C 0.54369(11) 0.60538(16) 1.1287(2) 0.0915(7) Uani 1 1 d .
C23 C 0.5000 0.6688(3) 0.7500 0.1115(13) Uani 1 2 d S
H16B H 0.7665(7) 0.5026(10) 1.1801(11) 0.051(4) Uiso 1 1 d .
H16A H 0.7276(7) 0.4057(12) 1.1534(11) 0.055(4) Uiso 1 1 d .
H3 H 0.6366(8) 0.3390(11) 1.0569(12) 0.063(4) Uiso 1 1 d .
H14B H 0.8589(9) 0.5863(11) 1.1368(13) 0.063(5) Uiso 1 1 d .
H4 H 0.5632(8) 0.2118(11) 1.0115(12) 0.065(5) Uiso 1 1 d .
H6 H 0.6413(8) 0.1603(12) 0.7756(13) 0.067(5) Uiso 1 1 d .
H14A H 0.7903(9) 0.6372(12) 1.1043(13) 0.069(5) Uiso 1 1 d .
H5 H 0.5655(9) 0.1195(14) 0.8715(13) 0.087(6) Uiso 1 1 d .
H12A H 0.9164(9) 0.6645(13) 0.9220(14) 0.080(5) Uiso 1 1 d .
H13B H 0.8789(9) 0.7215(13) 1.0598(14) 0.080(5) Uiso 1 1 d .
H18 H 0.6419(8) 0.5627(11) 0.9815(12) 0.063(5) Uiso 1 1 d .
H12B H 0.9371(11) 0.5978(15) 1.0129(16) 0.094(7) Uiso 1 1 d .
H13A H 0.8151(10) 0.7028(13) 0.9657(15) 0.086(6) Uiso 1 1 d .
H22 H 0.6639(9) 0.4758(13) 1.2690(13) 0.081(6) Uiso 1 1 d .
H21 H 0.5636(10) 0.5570(14) 1.2713(16) 0.099(7) Uiso 1 1 d .
H19 H 0.5437(11) 0.6364(17) 0.9833(18) 0.112(8) Uiso 1 1 d .
H20 H 0.5027(12) 0.6389(16) 1.1296(17) 0.116(7) Uiso 1 1 d .
H30 H 0.5298(9) 0.9843(13) 0.7255(13) 0.074(5) Uiso 1 1 d .
H25 H 0.5824(9) 0.8467(12) 0.6909(13) 0.079(5) Uiso 1 1 d .
H24 H 0.5837(13) 0.6843(18) 0.6964(19) 0.126(8) Uiso 1 1 d .
H23 H 0.5000 0.606(3) 0.7500 0.138(14) Uiso 1 2 d S
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C9 O2 C8 118.95(11) . .
C15 N1 C1 108.75(10) . .
C15 N1 C16 123.36(12) . .
C1 N1 C16 127.26(12) . .
C9 C1 N1 106.42(12) . .
C9 C1 C2 121.74(12) . .
N1 C1 C2 131.80(12) . .
N1 C15 C10 109.70(12) . .
N1 C15 C14 125.27(13) . .
C10 C15 C14 125.04(13) . .
C6 C7 C2 120.06(14) . .
C6 C7 C8 117.76(14) . .
C2 C7 C8 122.17(13) . .
C15 C10 C9 105.06(12) . .
C15 C10 C11 121.48(13) . .
C9 C10 C11 133.12(13) . .
C3 C2 C7 117.85(14) . .
C3 C2 C1 127.48(13) . .
C7 C2 C1 114.66(12) . .
C18 C17 C22 119.02(15) . .
C18 C17 C16 123.63(13) . .
C22 C17 C16 117.31(14) . .
C5 C3 C2 120.79(15) . .
C1 C9 O2 123.73(13) . .
C1 C9 C10 110.05(12) . .
O2 C9 C10 126.22(12) . .
N1 C16 C17 115.37(12) . .
C21 C22 C17 121.16(19) . .
O3 C11 C10 122.99(15) . .
O3 C11 C12 121.73(14) . .
C10 C11 C12 115.25(14) . .
O1 C8 O2 116.29(14) . .
O1 C8 C7 125.17(15) . .
O2 C8 C7 118.54(12) . .
C15 C14 C13 108.97(13) . .
C4 C6 C7 120.68(16) . .
N2 C26 C25 120.57(12) . 2_656
N2 C26 C25 120.57(12) . .
C25 C26 C25 118.9(2) 2_656 .
C17 C18 C19 119.47(19) . .
C3 C5 C4 120.95(16) . .
C6 C4 C5 119.66(16) . .
C24 C25 C26 119.8(2) . .
C12 C13 C14 112.25(17) . .
C20 C21 C22 119.7(2) . .
C11 C12 C13 114.09(16) . .
C20 C19 C18 120.2(2) . .
C23 C24 C25 121.2(2) . .
C21 C20 C19 120.4(2) . .
C24 C23 C24 119.2(3) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C9 1.3720(15) .
O2 C8 1.3770(18) .
N1 C15 1.3530(17) .
N1 C1 1.4021(17) .
N1 C16 1.4613(17) .
O1 C8 1.2043(17) .
O3 C11 1.2283(17) .
C1 C9 1.3624(18) .
C1 C2 1.435(2) .
C15 C10 1.3898(19) .
C15 C14 1.484(2) .
C7 C6 1.397(2) .
C7 C2 1.4142(19) .
C7 C8 1.469(2) .
C10 C9 1.410(2) .
C10 C11 1.444(2) .
C2 C3 1.402(2) .
C17 C18 1.369(2) .
C17 C22 1.382(2) .
C17 C16 1.505(2) .
C3 C5 1.376(2) .
C22 C21 1.373(3) .
C11 C12 1.512(3) .
C14 C13 1.522(2) .
C6 C4 1.371(2) .
C26 N2 1.374(3) .
C26 C25 1.389(2) 2_656
C26 C25 1.389(2) .
C18 C19 1.399(3) .
C5 C4 1.383(2) .
C25 C24 1.370(3) .
C13 C12 1.515(3) .
C21 C20 1.358(3) .
C19 C20 1.364(3) .
C24 C23 1.365(3) .
C23 C24 1.365(3) 2_656
