#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/51/7105104.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_7105104
loop_
_publ_author_name
'Savarimuthu Philip Anthony'
'Sunil Varughese'
'Sylvia M. Draper'
_publ_section_title
;
 Switching and tuning organic solid-state luminescence via a
 supramolecular approach
;
_journal_name_full               'Chem. Commun.'
_journal_page_first              7500
_journal_page_last               7502
_journal_paper_doi               10.1039/b914027a
_journal_year                    2009
_chemical_formula_moiety         'C22 H16 N2 O2, C4 H9 N'
_chemical_formula_sum            'C26 H25 N3 O2'
_chemical_formula_weight         411.49
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.704(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.461(1)
_cell_length_b                   25.424(2)
_cell_length_c                   11.161(1)
_cell_measurement_reflns_used    1860
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      41.651
_cell_measurement_theta_min      4.771
_cell_volume                     2180.0(3)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'Material Studio 4.3'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX CCD Area detector'
_diffrn_measurement_method       'phi and omega scan'
_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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12692
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick 1997'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blocks
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0611
_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)+(0.0926P)²+0.6140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1832
_reflns_number_gt                2648
_reflns_number_total             3855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b914027a.txt
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'multi scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7105104
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_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
O1A O 0.1814(3) 0.46947(11) 1.0359(3) 0.0962(9) Uani 1 1 d . . .
H1A H 0.1773 0.4814 0.9657 0.144 Uiso 1 1 d R . .
O1B O 0.3283(3) 0.40883(10) 1.2036(3) 0.0849(7) Uani 1 1 d . . .
N3 N 0.2889(4) 0.48044(12) 0.8023(3) 0.0850(9) Uani 1 1 d . . .
N5 N 0.9220(3) 0.31121(9) 0.8965(2) 0.0468(6) Uani 1 1 d . . .
C1 C 0.2924(4) 0.43339(13) 1.0952(3) 0.0612(8) Uani 1 1 d . . .
C2 C 0.3868(3) 0.42153(11) 1.0265(3) 0.0492(7) Uani 1 1 d . . .
C3 C 0.3368(4) 0.45379(12) 0.9025(3) 0.0575(7) Uani 1 1 d . . .
C4 C 0.5023(3) 0.38217(11) 1.0757(3) 0.0472(6) Uani 1 1 d . . .
H4 H 0.5151 0.3618 1.1529 0.057 Uiso 1 1 calc R . .
C6 C 0.8217(3) 0.32951(10) 0.9442(2) 0.0403(6) Uani 1 1 d . . .
C7 C 0.7603(3) 0.38073(10) 0.9167(3) 0.0478(6) Uani 1 1 d . . .
H7 H 0.7911 0.4042 0.8692 0.057 Uiso 1 1 calc R . .
C8 C 0.6560(3) 0.39823(10) 0.9565(3) 0.0496(7) Uani 1 1 d . . .
H8 H 0.6134 0.4333 0.9336 0.060 Uiso 1 1 calc R . .
C9 C 0.6111(3) 0.36561(10) 1.0297(3) 0.0421(6) Uani 1 1 d . . .
C10 C 0.6808(3) 0.31489(10) 1.0633(3) 0.0447(6) Uani 1 1 d . . .
H10 H 0.6580 0.2922 1.1179 0.054 Uiso 1 1 calc R . .
C11 C 0.7816(3) 0.29660(10) 1.0198(3) 0.0426(6) Uani 1 1 d . . .
H11 H 0.8236 0.2615 1.0416 0.051 Uiso 1 1 calc R . .
C12 C 0.8882(3) 0.32942(9) 0.7619(3) 0.0405(6) Uani 1 1 d . . .
C13 C 1.0231(3) 0.34081(11) 0.7512(3) 0.0513(7) Uani 1 1 d . . .
H13 H 1.1402 0.3369 0.8348 0.062 Uiso 1 1 calc R . .
C14 C 0.9878(4) 0.35780(12) 0.6197(4) 0.0647(8) Uani 1 1 d . . .
H14 H 1.0814 0.3653 0.6131 0.078 Uiso 1 1 calc R . .
C15 C 0.8204(4) 0.36419(12) 0.4979(3) 0.0666(8) Uani 1 1 d . . .
H15 H 0.7981 0.3760 0.4076 0.080 Uiso 1 1 calc R . .
C16 C 0.6858(4) 0.35357(11) 0.5069(3) 0.0595(8) Uani 1 1 d . . .
H16 H 0.5693 0.3586 0.4232 0.071 Uiso 1 1 calc R . .
C17 C 0.7187(3) 0.33549(10) 0.6377(3) 0.0498(7) Uani 1 1 d . . .
H17 H 0.6243 0.3271 0.6425 0.060 Uiso 1 1 calc R . .
C18 C 1.0670(3) 0.27764(10) 0.9890(3) 0.0417(6) Uani 1 1 d . . .
C19 C 1.1780(3) 0.28665(11) 1.1384(3) 0.0510(7) Uani 1 1 d . . .
H19 H 1.1576 0.3155 1.1806 0.061 Uiso 1 1 calc R . .
C20 C 1.3187(3) 0.25403(12) 1.2272(3) 0.0588(8) Uani 1 1 d . . .
H20 H 1.3931 0.2600 1.3307 0.071 Uiso 1 1 calc R . .
C21 C 1.3517(4) 0.21313(12) 1.1671(3) 0.0593(8) Uani 1 1 d . . .
H21 H 1.4483 0.1906 1.2287 0.071 Uiso 1 1 calc R . .
C22 C 1.2452(4) 0.20480(11) 1.0183(3) 0.0582(8) Uani 1 1 d . . .
H22 H 1.2705 0.1772 0.9762 0.070 Uiso 1 1 calc R . .
C23 C 1.1021(3) 0.23602(11) 0.9292(3) 0.0508(7) Uani 1 1 d . . .
H23 H 1.0266 0.2292 0.8263 0.061 Uiso 1 1 calc R . .
N24 N 0.7907(9) 0.55531(18) 0.5424(4) 0.192(3) Uani 1 1 d . . .
H24 H 0.7395 0.5781 0.4724 0.231 Uiso 1 1 d R . .
C25 C 0.7468(8) 0.5027(2) 0.5292(5) 0.134(2) Uani 1 1 d . . .
H25A H 0.8009 0.4826 0.4896 0.161 Uiso 1 1 calc R . .
H25B H 0.6190 0.4984 0.4607 0.161 Uiso 1 1 calc R . .
C26 C 0.8099(5) 0.48301(14) 0.6758(4) 0.0846(11) Uani 1 1 d . . .
H26A H 0.8729 0.4494 0.6961 0.101 Uiso 1 1 calc R . .
H26B H 0.7114 0.4772 0.6827 0.101 Uiso 1 1 calc R . .
C27 C 0.9283(3) 0.52381(10) 0.7821(3) 0.0458(6) Uani 1 1 d . . .
H27A H 0.8820 0.5380 0.8354 0.055 Uiso 1 1 calc R . .
H27B H 1.0448 0.5086 0.8552 0.055 Uiso 1 1 calc R . .
C28 C 0.9408(5) 0.56588(14) 0.6982(4) 0.0778(10) Uani 1 1 d . . .
H28A H 1.0526 0.5640 0.7097 0.093 Uiso 1 1 calc R . .
H28B H 0.9303 0.6010 0.7308 0.093 Uiso 1 1 calc R . .
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
_geom_angle_publ_flag
C1 O1A H1A 109.5 . . ?
C6 N5 C12 120.45(19) . . ?
C6 N5 C18 120.01(19) . . ?
C12 N5 C18 119.34(19) . . ?
O1B C1 O1A 124.1(3) . . ?
O1B C1 C2 119.8(3) . . ?
O1A C1 C2 116.1(3) . . ?
C4 C2 C3 123.7(2) . . ?
C4 C2 C1 121.6(3) . . ?
C3 C2 C1 114.6(2) . . ?
N3 C3 C2 176.4(3) . . ?
C2 C4 C9 130.3(3) . . ?
C2 C4 H4 114.8 . . ?
C9 C4 H4 114.8 . . ?
C7 C6 C11 118.2(2) . . ?
C7 C6 N5 120.9(2) . . ?
C11 C6 N5 120.9(2) . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 121.3(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 116.7(2) . . ?
C8 C9 C4 123.7(2) . . ?
C10 C9 C4 119.5(2) . . ?
C11 C10 C9 122.1(2) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C6 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C13 C12 C17 118.6(2) . . ?
C13 C12 N5 120.8(2) . . ?
C17 C12 N5 120.6(2) . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C19 C18 C23 118.8(2) . . ?
C19 C18 N5 120.7(2) . . ?
C23 C18 N5 120.5(2) . . ?
C18 C19 C20 120.3(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.3(2) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
C25 N24 C28 108.7(4) . . ?
C25 N24 H24 125.5 . . ?
C28 N24 H24 125.8 . . ?
N24 C25 C26 108.1(4) . . ?
N24 C25 H25A 110.1 . . ?
C26 C25 H25A 110.1 . . ?
N24 C25 H25B 110.1 . . ?
C26 C25 H25B 110.1 . . ?
H25A C25 H25B 108.4 . . ?
C25 C26 C27 106.3(3) . . ?
C25 C26 H26A 110.5 . . ?
C27 C26 H26A 110.5 . . ?
C25 C26 H26B 110.5 . . ?
C27 C26 H26B 110.5 . . ?
H26A C26 H26B 108.7 . . ?
C28 C27 C26 107.7(2) . . ?
C28 C27 H27A 110.2 . . ?
C26 C27 H27A 110.2 . . ?
C28 C27 H27B 110.2 . . ?
C26 C27 H27B 110.2 . . ?
H27A C27 H27B 108.5 . . ?
C27 C28 N24 103.6(3) . . ?
C27 C28 H28A 111.0 . . ?
N24 C28 H28A 111.0 . . ?
C27 C28 H28B 111.0 . . ?
N24 C28 H28B 111.0 . . ?
H28A C28 H28B 109.0 . . ?
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
O1A C1 1.253(4) . ?
O1A H1A 0.8201 . ?
O1B C1 1.221(4) . ?
N3 C3 1.150(4) . ?
N5 C6 1.411(3) . ?
N5 C12 1.419(3) . ?
N5 C18 1.422(3) . ?
C1 C2 1.509(4) . ?
C2 C4 1.340(4) . ?
C2 C3 1.431(4) . ?
C4 C9 1.455(3) . ?
C4 H4 0.9500 . ?
C6 C7 1.385(4) . ?
C6 C11 1.390(3) . ?
C7 C8 1.372(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(4) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 C17 1.386(3) . ?
C13 C14 1.371(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.361(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.376(3) . ?
C18 C23 1.390(3) . ?
C19 C20 1.379(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.369(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.366(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
N24 C25 1.384(6) . ?
N24 C28 1.494(5) . ?
N24 H24 0.8601 . ?
C25 C26 1.464(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.479(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.471(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653169
