#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/55/7205579.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_7205579
loop_
_publ_author_name
'Yao, Dandan'
'Zhao, Shanshan'
'Guo, Jianhua'
'Zhang, Zuolun'
'Zhang, Hongyu'
'Liu, Yu'
'Wang, Yue'
_publ_section_title
;
 Hydroxyphenyl-benzothiazole based full color organic emitting
 materials generated by facile molecular modification
;
_journal_issue                   11
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              3568
_journal_paper_doi               10.1039/c1jm00009h
_journal_volume                  21
_journal_year                    2011
_chemical_formula_sum            'C25 H16 N2 O S'
_chemical_formula_weight         392.46
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.949(2)
_cell_length_b                   15.759(3)
_cell_length_c                   13.031(3)
_cell_measurement_reflns_used    4382
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.07
_cell_volume                     1930.6(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Omega scan'
_diffrn_measurement_method       10.0
_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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18395
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9592
_exptl_absorpt_correction_T_min  0.9416
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colorless
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0408
_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)+(0.0541P)²+0.3109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                3214
_reflns_number_total             4382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C1JM00009H.TXT
_cod_data_source_block           pCzOH
_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.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1930.5(7)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7205579
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45031(17) 0.02839(11) 1.22899(13) 0.0465(4) Uani 1 1 d . . .
C2 C 0.4915(2) -0.03933(12) 1.30052(16) 0.0627(5) Uani 1 1 d . . .
H2 H 0.5697 -0.0726 1.3030 0.075 Uiso 1 1 calc R . .
C3 C 0.4130(2) -0.05558(14) 1.36749(18) 0.0752(6) Uani 1 1 d . . .
H3 H 0.4389 -0.1004 1.4165 0.090 Uiso 1 1 calc R . .
C4 C 0.2962(2) -0.00641(16) 1.36330(18) 0.0767(6) Uani 1 1 d . . .
H4 H 0.2437 -0.0198 1.4085 0.092 Uiso 1 1 calc R . .
C5 C 0.2556(2) 0.06177(13) 1.29402(17) 0.0641(5) Uani 1 1 d . . .
H5 H 0.1779 0.0950 1.2928 0.077 Uiso 1 1 calc R . .
C6 C 0.33463(17) 0.07949(10) 1.22571(13) 0.0463(4) Uani 1 1 d . . .
C7 C 0.39636(15) 0.14218(10) 1.09498(13) 0.0408(3) Uani 1 1 d . . .
C8 C 0.39153(15) 0.20204(10) 1.00881(12) 0.0400(3) Uani 1 1 d . . .
C9 C 0.28932(16) 0.26740(10) 0.98185(13) 0.0431(4) Uani 1 1 d . . .
C10 C 0.28448(16) 0.32393(10) 0.89932(13) 0.0445(4) Uani 1 1 d . . .
H10 H 0.2168 0.3670 0.8818 0.053 Uiso 1 1 calc R . .
C11 C 0.37984(16) 0.31651(10) 0.84301(13) 0.0430(4) Uani 1 1 d . . .
C12 C 0.48055(17) 0.25176(11) 0.86757(14) 0.0474(4) Uani 1 1 d . . .
H12 H 0.5440 0.2466 0.8291 0.057 Uiso 1 1 calc R . .
C13 C 0.48520(16) 0.19561(10) 0.94921(13) 0.0451(4) Uani 1 1 d . . .
H13 H 0.5523 0.1522 0.9653 0.054 Uiso 1 1 calc R . .
C14 C 0.37857(15) 0.46443(10) 0.77210(14) 0.0446(4) Uani 1 1 d . . .
C15 C 0.38852(18) 0.51245(11) 0.86303(15) 0.0525(4) Uani 1 1 d . . .
H15 H 0.3894 0.4870 0.9277 0.063 Uiso 1 1 calc R . .
C16 C 0.3971(2) 0.59970(12) 0.85458(18) 0.0637(5) Uani 1 1 d . . .
H16 H 0.4046 0.6336 0.9147 0.076 Uiso 1 1 calc R . .
C17 C 0.3946(2) 0.63744(13) 0.75749(19) 0.0680(6) Uani 1 1 d . . .
H17 H 0.4007 0.6962 0.7537 0.082 Uiso 1 1 calc R . .
C18 C 0.38324(19) 0.58957(12) 0.66746(17) 0.0603(5) Uani 1 1 d . . .
H18 H 0.3811 0.6156 0.6029 0.072 Uiso 1 1 calc R . .
C19 C 0.37490(16) 0.50138(11) 0.67338(14) 0.0481(4) Uani 1 1 d . . .
C20 C 0.36679(16) 0.43315(11) 0.59804(14) 0.0488(4) Uani 1 1 d . . .
C21 C 0.35437(19) 0.42952(15) 0.48790(16) 0.0616(5) Uani 1 1 d . . .
H21 H 0.3516 0.4791 0.4486 0.074 Uiso 1 1 calc R . .
C22 C 0.3464(2) 0.35192(17) 0.43879(16) 0.0688(6) Uani 1 1 d . . .
H22 H 0.3379 0.3493 0.3656 0.083 Uiso 1 1 calc R . .
C23 C 0.35092(19) 0.27729(15) 0.49617(16) 0.0650(5) Uani 1 1 d . . .
H23 H 0.3471 0.2256 0.4610 0.078 Uiso 1 1 calc R . .
C24 C 0.36101(18) 0.27804(12) 0.60457(15) 0.0557(4) Uani 1 1 d . . .
H24 H 0.3624 0.2279 0.6426 0.067 Uiso 1 1 calc R . .
C25 C 0.36891(16) 0.35667(11) 0.65427(13) 0.0462(4) Uani 1 1 d . . .
N1 N 0.30661(14) 0.14380(9) 1.14887(11) 0.0478(3) Uani 1 1 d . . .
N2 N 0.37588(14) 0.37596(9) 0.76040(11) 0.0457(3) Uani 1 1 d . . .
O1 O 0.19176(14) 0.27698(8) 1.03195(11) 0.0613(4) Uani 1 1 d . . .
H1 H 0.2027 0.2399 1.0781 0.092 Uiso 1 1 calc R . .
S1 S 0.52411(5) 0.06191(3) 1.13278(4) 0.05150(15) Uani 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'
S S 0.1246 0.1234 '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
C2 C1 C6 121.63(16) . . ?
C2 C1 S1 128.28(14) . . ?
C6 C1 S1 110.09(12) . . ?
C3 C2 C1 117.79(19) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.07(19) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 121.70(19) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 117.98(19) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C1 114.40(14) . . ?
N1 C6 C5 125.77(16) . . ?
C1 C6 C5 119.80(16) . . ?
N1 C7 C8 123.17(14) . . ?
N1 C7 S1 115.19(12) . . ?
C8 C7 S1 121.64(11) . . ?
C13 C8 C9 118.18(14) . . ?
C13 C8 C7 121.45(14) . . ?
C9 C8 C7 120.35(14) . . ?
O1 C9 C10 117.24(14) . . ?
O1 C9 C8 122.56(14) . . ?
C10 C9 C8 120.18(14) . . ?
C11 C10 C9 120.17(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.52(14) . . ?
C10 C11 N2 119.61(14) . . ?
C12 C11 N2 119.87(14) . . ?
C13 C12 C11 119.33(15) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C8 121.61(15) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
C15 C14 C19 122.17(16) . . ?
C15 C14 N2 129.15(15) . . ?
C19 C14 N2 108.64(15) . . ?
C14 C15 C16 117.70(17) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 121.08(18) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.42(18) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C14 118.70(18) . . ?
C18 C19 C20 134.16(17) . . ?
C14 C19 C20 107.11(15) . . ?
C21 C20 C25 118.67(18) . . ?
C21 C20 C19 134.05(17) . . ?
C25 C20 C19 107.25(15) . . ?
C22 C21 C20 119.15(19) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 121.22(19) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 121.5(2) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 117.26(18) . . ?
C23 C24 H24 121.4 . . ?
C25 C24 H24 121.4 . . ?
C24 C25 N2 129.31(16) . . ?
C24 C25 C20 122.19(17) . . ?
N2 C25 C20 108.48(15) . . ?
C7 N1 C6 111.28(14) . . ?
C25 N2 C14 108.50(13) . . ?
C25 N2 C11 126.06(14) . . ?
C14 N2 C11 125.44(14) . . ?
C9 O1 H1 109.5 . . ?
C1 S1 C7 89.04(8) . . ?
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
C1 C2 1.388(2) . ?
C1 C6 1.394(2) . ?
C1 S1 1.7299(17) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.387(2) . ?
C7 N1 1.3045(19) . ?
C7 C8 1.455(2) . ?
C7 S1 1.7459(16) . ?
C8 C13 1.398(2) . ?
C8 C9 1.409(2) . ?
C9 O1 1.3438(18) . ?
C9 C10 1.385(2) . ?
C10 C11 1.381(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(2) . ?
C11 N2 1.4177(19) . ?
C12 C13 1.373(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.382(2) . ?
C14 C19 1.402(2) . ?
C14 N2 1.402(2) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.391(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.396(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.440(3) . ?
C20 C21 1.401(3) . ?
C20 C25 1.407(2) . ?
C21 C22 1.370(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.388(3) . ?
C24 H24 0.9300 . ?
C25 N2 1.395(2) . ?
O1 H1 0.8200 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653742
