#------------------------------------------------------------------------------
#$Date: 2019-11-28 20:04:50 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244473 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/89/7238939.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_7238939
loop_
_publ_author_name
'Bag, Subhendu Sekhar'
'Ghorai, Samir'
'Jana, Subhashis'
'Mukherjee, Chandan'
_publ_section_title
;
 Solvatochromic fluorescent cyanophenoxazine: design, synthesis,
 photophysical properties and fluorescence light-up sensing of ct-DNA
;
_journal_issue                   16
_journal_name_full               'RSC Advances'
_journal_page_first              5374
_journal_paper_doi               10.1039/c3ra23463k
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C21 H24 N2 O'
_chemical_formula_sum            'C21 H24 N2 O'
_chemical_formula_weight         320.42
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.012(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   34.3374(12)
_cell_length_b                   6.0181(2)
_cell_length_c                   18.6307(6)
_cell_measurement_temperature    296(2)
_cell_volume                     3735.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20752
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0856
_refine_ls_shift/su_max          0.372
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1701P)²+4.5130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2631
_refine_ls_wR_factor_ref         0.2862
_reflns_number_gt                2306
_reflns_number_total             3093
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ra23463k.txt
_cod_data_source_block           cm00301_0m
_cod_database_code               7238939
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
C12 C 0.11243(9) 0.1382(5) 0.29665(15) 0.0501(8) Uani 1 1 d .
C8 C 0.16296(9) 0.3533(5) 0.38188(16) 0.0530(8) Uani 1 1 d .
C13 C 0.15200(9) 0.2013(5) 0.32434(16) 0.0509(8) Uani 1 1 d .
C6 C 0.23248(10) 0.3032(5) 0.38268(16) 0.0532(8) Uani 1 1 d .
C10 C 0.09477(9) 0.3718(5) 0.39221(16) 0.0524(8) Uani 1 1 d .
C9 C 0.13438(9) 0.4333(5) 0.41616(16) 0.0538(8) Uani 1 1 d .
H9 H 0.1420 0.5301 0.4560 0.065 Uiso 1 1 calc R
C11 C 0.08463(10) 0.2264(5) 0.33258(16) 0.0535(8) Uani 1 1 d .
H11 H 0.0578 0.1857 0.3157 0.064 Uiso 1 1 calc R
C5 C 0.27332(10) 0.3337(5) 0.41239(17) 0.0568(8) Uani 1 1 d .
C1 C 0.22080(10) 0.1399(5) 0.32812(17) 0.0537(8) Uani 1 1 d .
C2 C 0.24836(11) 0.0068(6) 0.30743(19) 0.0631(9) Uani 1 1 d .
H2 H 0.2399 -0.1043 0.2724 0.076 Uiso 1 1 calc R
C7 C 0.28644(10) 0.5061(6) 0.4660(2) 0.0636(9) Uani 1 1 d .
C4 C 0.30171(11) 0.2016(6) 0.3896(2) 0.0690(10) Uani 1 1 d .
H4 H 0.3290 0.2256 0.4091 0.083 Uiso 1 1 calc R
C3 C 0.28912(12) 0.0371(6) 0.3386(2) 0.0716(10) Uani 1 1 d .
H3 H 0.3078 -0.0545 0.3247 0.086 Uiso 1 1 calc R
C14 C 0.09982(10) -0.0115(5) 0.22780(16) 0.0572(9) Uani 1 1 d .
C16 C 0.11984(13) -0.2387(6) 0.2412(2) 0.0767(11) Uani 1 1 d .
H16A H 0.1485 -0.2208 0.2536 0.115 Uiso 1 1 calc R
H16B H 0.1118 -0.3274 0.1973 0.115 Uiso 1 1 calc R
H16C H 0.1119 -0.3112 0.2813 0.115 Uiso 1 1 calc R
C17 C 0.11171(16) 0.1018(7) 0.16286(19) 0.0912(14) Uani 1 1 d .
H17A H 0.1000 0.2475 0.1558 0.137 Uiso 1 1 calc R
H17B H 0.1022 0.0152 0.1188 0.137 Uiso 1 1 calc R
H17C H 0.1404 0.1138 0.1732 0.137 Uiso 1 1 calc R
C15 C 0.05461(12) -0.0501(9) 0.2071(2) 0.0972(15) Uani 1 1 d .
H15A H 0.0467 -0.1210 0.2475 0.146 Uiso 1 1 calc R
H15B H 0.0476 -0.1435 0.1641 0.146 Uiso 1 1 calc R
H15C H 0.0410 0.0898 0.1966 0.146 Uiso 1 1 calc R
C18 C 0.06320(10) 0.4583(6) 0.43153(18) 0.0632(9) Uani 1 1 d .
C20 C 0.0247(2) 0.473(2) 0.3838(5) 0.285(8) Uani 1 1 d .
H20A H 0.0218 0.6142 0.3589 0.428 Uiso 1 1 calc R
H20B H 0.0048 0.4601 0.4120 0.428 Uiso 1 1 calc R
H20C H 0.0211 0.3558 0.3479 0.428 Uiso 1 1 calc R
C19 C 0.0720(3) 0.6818(16) 0.4590(8) 0.308(9) Uani 1 1 d .
H19A H 0.0890 0.7534 0.4319 0.462 Uiso 1 1 calc R
H19B H 0.0855 0.6767 0.5105 0.462 Uiso 1 1 calc R
H19C H 0.0474 0.7638 0.4528 0.462 Uiso 1 1 calc R
C21 C 0.0622(4) 0.324(2) 0.4918(7) 0.378(12) Uani 1 1 d .
H21A H 0.0589 0.4146 0.5322 0.567 Uiso 1 1 calc R
H21B H 0.0869 0.2425 0.5064 0.567 Uiso 1 1 calc R
H21C H 0.0402 0.2216 0.4783 0.567 Uiso 1 1 calc R
N1 N 0.20295(8) 0.4243(5) 0.40343(17) 0.0688(9) Uani 1 1 d .
N2 N 0.29567(10) 0.6465(6) 0.5078(2) 0.0880(11) Uani 1 1 d .
O1 O 0.18119(7) 0.1190(4) 0.29101(13) 0.0710(8) Uani 1 1 d .
H1N H 0.2098(12) 0.539(8) 0.438(2) 0.091(12) Uiso 1 1 d .
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
C13 C12 C11 116.1(3)
C13 C12 C14 121.5(3)
C11 C12 C14 122.3(3)
C9 C8 C13 119.7(3)
C9 C8 N1 121.2(3)
C13 C8 N1 119.0(3)
C12 C13 C8 121.7(3)
C12 C13 O1 118.9(3)
C8 C13 O1 119.2(3)
N1 C6 C5 124.0(3)
N1 C6 C1 118.3(3)
C5 C6 C1 117.7(3)
C9 C10 C11 117.7(3)
C9 C10 C18 120.7(3)
C11 C10 C18 121.6(3)
C10 C9 C8 120.9(3)
C10 C11 C12 123.7(3)
C6 C5 C4 120.9(3)
C6 C5 C7 119.3(3)
C4 C5 C7 119.8(3)
C2 C1 O1 118.3(3)
C2 C1 C6 121.4(3)
O1 C1 C6 120.2(3)
C1 C2 C3 120.1(3)
N2 C7 C5 177.7(4)
C3 C4 C5 119.7(3)
C4 C3 C2 120.1(3)
C16 C14 C15 107.2(3)
C16 C14 C17 109.5(3)
C15 C14 C17 108.6(3)
C16 C14 C12 111.3(3)
C15 C14 C12 111.3(3)
C17 C14 C12 108.9(3)
C21 C18 C20 110.2(8)
C21 C18 C19 107.4(9)
C20 C18 C19 104.4(8)
C21 C18 C10 110.2(4)
C20 C18 C10 112.6(4)
C19 C18 C10 111.9(4)
C6 N1 C8 119.7(3)
C1 O1 C13 118.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C12 C13 1.385(4)
C12 C11 1.397(4)
C12 C14 1.541(4)
C8 C9 1.381(4)
C8 C13 1.390(4)
C8 N1 1.401(4)
C13 O1 1.392(4)
C6 N1 1.378(4)
C6 C5 1.389(5)
C6 C1 1.401(4)
C10 C9 1.376(4)
C10 C11 1.391(4)
C10 C18 1.538(4)
C5 C4 1.401(5)
C5 C7 1.435(5)
C1 C2 1.364(4)
C1 O1 1.374(4)
C2 C3 1.391(5)
C7 N2 1.141(4)
C4 C3 1.368(5)
C14 C16 1.524(5)
C14 C15 1.524(5)
C14 C17 1.528(5)
C18 C21 1.391(8)
C18 C20 1.407(7)
C18 C19 1.445(8)
