#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209576.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_7209576
loop_
_publ_author_name
'Anthony, Savarimuthu Philip'
'Varughese, Sunil'
_publ_section_title
;
 Diaminotriazine substituted diphenyl ether: reversible structural
 transformation and solvent dependent solid state fluorescence
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              4117
_journal_paper_doi               10.1039/c3ce00014a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C18 H16 N10 O, H2 O'
_chemical_formula_sum            'C18 H18 N10 O2'
_chemical_formula_weight         406.42
_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                 115.635(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.882(4)
_cell_length_b                   7.619(2)
_cell_length_c                   17.176(4)
_cell_measurement_reflns_used    3276
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      47.89
_cell_measurement_theta_min      2.89
_cell_volume                     1873.8(8)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0775
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10566
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1997'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blocks
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0489
_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)+(0.0472P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2069
_reflns_number_total             3290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce00014a.txt
_cod_data_source_block           w
_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 2.4.2 from
2011-04-26.

'_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7209576
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
O1 O 0.41371(10) 0.5769(2) 0.38449(9) 0.0484(5) Uani 1 1 d
N8 N 0.06325(12) 0.7391(2) 0.46293(11) 0.0357(5) Uani 1 1 d
N9 N -0.07844(14) 0.8387(3) 0.45097(14) 0.0452(6) Uani 1 1 d
N10 N 0.01534(13) 0.6948(2) 0.57548(12) 0.0409(5) Uani 1 1 d
N11 N 0.11381(18) 0.5478(3) 0.69633(14) 0.0537(7) Uani 1 1 d
N12 N 0.16414(13) 0.5896(2) 0.59136(11) 0.0400(5) Uani 1 1 d
N20 N 0.38264(12) 0.4651(2) 0.00435(11) 0.0372(5) Uani 1 1 d
N21 N 0.41003(17) 0.4744(3) -0.11614(16) 0.0520(6) Uani 1 1 d
N22 N 0.26586(13) 0.3775(2) -0.13415(11) 0.0362(5) Uani 1 1 d
N23 N 0.12762(14) 0.2686(3) -0.14232(14) 0.0457(6) Uani 1 1 d
N24 N 0.23388(12) 0.3694(2) -0.01085(11) 0.0346(5) Uani 1 1 d
C1 C 0.34303(15) 0.5900(3) 0.41197(14) 0.0374(6) Uani 1 1 d
C2 C 0.25691(17) 0.6574(3) 0.36019(16) 0.0452(7) Uani 1 1 d
C3 C 0.19218(17) 0.6789(3) 0.39316(15) 0.0424(6) Uani 1 1 d
C4 C 0.21255(15) 0.6318(3) 0.47785(13) 0.0347(5) Uani 1 1 d
C5 C 0.29972(16) 0.5617(3) 0.52770(15) 0.0400(6) Uani 1 1 d
C6 C 0.36495(17) 0.5407(3) 0.49543(15) 0.0427(6) Uani 1 1 d
C7 C 0.14270(15) 0.6557(3) 0.51304(14) 0.0337(5) Uani 1 1 d
C9 C 0.00181(16) 0.7559(3) 0.49792(14) 0.0362(5) Uani 1 1 d
C11 C 0.09729(16) 0.6134(3) 0.61914(14) 0.0375(6) Uani 1 1 d
C13 C 0.38938(15) 0.5399(3) 0.29805(13) 0.0371(6) Uani 1 1 d
C14 C 0.43298(17) 0.6330(3) 0.25744(15) 0.0406(6) Uani 1 1 d
C15 C 0.41171(16) 0.5966(3) 0.17250(15) 0.0391(6) Uani 1 1 d
C16 C 0.34731(14) 0.4668(3) 0.12758(13) 0.0331(5) Uani 1 1 d
C17 C 0.30656(16) 0.3707(3) 0.17122(14) 0.0373(6) Uani 1 1 d
C18 C 0.32713(17) 0.4078(3) 0.25579(15) 0.0399(6) Uani 1 1 d
C19 C 0.31987(15) 0.4327(3) 0.03463(13) 0.0312(5) Uani 1 1 d
C21 C 0.35071(15) 0.4376(3) -0.08126(13) 0.0355(6) Uani 1 1 d
C23 C 0.21197(15) 0.3383(3) -0.09466(14) 0.0334(5) Uani 1 1 d
H2 H 0.2424(15) 0.690(3) 0.3059(15) 0.049(7) Uiso 1 1 d
H3 H 0.1296(17) 0.730(3) 0.3568(14) 0.053(7) Uiso 1 1 d
H5 H 0.3154(14) 0.528(3) 0.5845(14) 0.040(6) Uiso 1 1 d
H6 H 0.4213(16) 0.494(3) 0.5291(14) 0.045(7) Uiso 1 1 d
H9A H -0.0896(17) 0.885(3) 0.3928(16) 0.064(8) Uiso 1 1 d
H9B H -0.1213(17) 0.848(3) 0.4684(14) 0.045(7) Uiso 1 1 d
H11A H 0.072(2) 0.562(4) 0.7117(17) 0.064(9) Uiso 1 1 d
H11B H 0.169(2) 0.496(3) 0.7266(16) 0.069(9) Uiso 1 1 d
H14 H 0.4745(16) 0.726(3) 0.2853(14) 0.055(7) Uiso 1 1 d
H15 H 0.4379(15) 0.668(3) 0.1422(13) 0.039(6) Uiso 1 1 d
H17 H 0.2646(14) 0.273(3) 0.1431(12) 0.032(6) Uiso 1 1 d
H18 H 0.2973(15) 0.340(3) 0.2826(14) 0.043(6) Uiso 1 1 d
H21A H 0.478(2) 0.499(4) -0.0748(19) 0.101(10) Uiso 1 1 d
H21B H 0.3883(17) 0.461(3) -0.1692(17) 0.060(9) Uiso 1 1 d
H23A H 0.1164(14) 0.225(3) -0.1921(14) 0.036(7) Uiso 1 1 d
H23B H 0.093(2) 0.231(4) -0.1120(19) 0.083(10) Uiso 1 1 d
O90 O -0.01938(14) 0.9224(3) 0.30446(12) 0.0657(6) Uani 1 1 d
H90A H 0.020(2) 0.848(4) 0.362(2) 0.112(12) Uiso 1 1 d
H90B H 0.002(3) 1.042(6) 0.318(3) 0.18(2) 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 O1 C1 118.83(16)
C7 N8 C9 114.73(19)
C9 N10 C11 114.63(19)
C7 N12 C11 114.10(18)
C19 N20 C21 113.91(18)
C23 N22 C21 114.20(18)
C19 N24 C23 114.47(18)
C2 C1 C6 120.8(2)
C2 C1 O1 122.1(2)
C6 C1 O1 117.1(2)
C1 C2 C3 119.3(2)
C2 C3 C4 121.3(2)
C5 C4 C3 117.6(2)
C5 C4 C7 121.3(2)
C3 C4 C7 121.1(2)
C6 C5 C4 121.4(2)
C1 C6 C5 119.5(2)
N12 C7 N8 125.8(2)
N12 C7 C4 116.98(19)
N8 C7 C4 117.25(19)
N9 C9 N10 117.8(2)
N9 C9 N8 117.3(2)
N10 C9 N8 124.9(2)
N11 C11 N10 117.1(2)
N11 C11 N12 117.0(2)
N10 C11 N12 125.9(2)
C14 C13 C18 121.0(2)
C14 C13 O1 118.0(2)
C18 C13 O1 121.0(2)
C13 C14 C15 119.2(2)
C14 C15 C16 121.0(2)
C15 C16 C17 118.5(2)
C15 C16 C19 121.6(2)
C17 C16 C19 119.9(2)
C18 C17 C16 120.5(2)
C17 C18 C13 119.7(2)
N20 C19 N24 125.95(19)
N20 C19 C16 117.81(19)
N24 C19 C16 116.24(18)
N22 C21 N21 117.5(2)
N22 C21 N20 125.9(2)
N21 C21 N20 116.6(2)
N22 C23 N23 118.0(2)
N22 C23 N24 125.2(2)
N23 C23 N24 116.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.392(2)
O1 C1 1.397(2)
N8 C7 1.341(3)
N8 C9 1.355(3)
N9 C9 1.336(3)
N10 C9 1.338(3)
N10 C11 1.340(3)
N11 C11 1.333(3)
N12 C7 1.335(3)
N12 C11 1.351(3)
N20 C19 1.332(3)
N20 C21 1.348(3)
N21 C21 1.347(3)
N22 C23 1.336(3)
N22 C21 1.339(3)
N23 C23 1.341(3)
N24 C19 1.336(3)
N24 C23 1.348(3)
C1 C2 1.368(3)
C1 C6 1.373(3)
C2 C3 1.381(3)
C3 C4 1.394(3)
C4 C5 1.382(3)
C4 C7 1.486(3)
C5 C6 1.380(3)
C13 C14 1.374(3)
C13 C18 1.377(3)
C14 C15 1.376(3)
C15 C16 1.391(3)
C16 C17 1.392(3)
C16 C19 1.485(3)
C17 C18 1.373(3)
