#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/02/4510211.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_4510211
loop_
_publ_author_name
'Lumpi, Daniel'
'Glöcklhofer, Florian'
'Holzer, Brigitte'
'Stöger, Berthold'
'Hametner, Christian'
'Reider, Georg A.'
'Fröhlich, Johannes'
_publ_section_title
;
 Systematic Investigations on 1,2,3-Triazole-Based Compounds Capable of
 Second Harmonic Generation
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1018
_journal_paper_doi               10.1021/cg4014762
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C12 H13 N3 O2 S'
_chemical_formula_weight         263.3
_chemical_name_systematic        ' ?'
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7982(8)
_cell_length_b                   13.6159(8)
_cell_length_c                   7.1310(4)
_cell_measurement_reflns_used    23765
_cell_measurement_temperature    100
_cell_measurement_theta_max      37.2
_cell_measurement_theta_min      2.2
_cell_volume                     1242.64(13)
_computing_cell_refinement       unknown
_computing_data_collection       unknown
_computing_data_reduction        unknown
_computing_molecular_graphics    unknown
_computing_structure_solution    unknown
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            53360
_diffrn_reflns_theta_full        37.55
_diffrn_reflns_theta_max         37.55
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.55
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_details
'  3070 of Friedel pairs used in the refinement'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    2.00
_refine_ls_goodness_of_fit_ref   1.92
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_constraints    1
_refine_ls_number_parameters     215
_refine_ls_number_reflns         6545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.0226
_refine_ls_shift/su_mean         0.0021
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0367
_refine_ls_wR_factor_ref         0.0370
_reflns_number_gt                5940
_reflns_number_total             6545
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            12ba_EMSO2M-4P.cif
_cod_data_source_block           12ba
_cod_original_sg_symbol_Hall     'P -2xabc;-2yab;2zc'
_cod_original_formula_sum        'C12 H13 N3 O2 S1'
_cod_database_code               4510211
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,z+1/2
3 x+1/2,-y+1/2,z
4 -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_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
S1 S 0.969518(13) 0.158759(14) 0.340058 Uani 0.01530(4) 4 1 d
O1 O 1.02339(5) 0.08227(6) 0.44141(13) Uani 0.02470(19) 4 1 d
O2 O 0.97985(5) 0.25829(5) 0.40822(11) Uani 0.02223(17) 4 1 d
C1 C 0.43453(5) -0.06018(6) 0.34607(14) Uani 0.01479(16) 4 1 d
C2 C 0.37313(6) 0.02063(6) 0.39327(13) Uani 0.01795(19) 4 1 d
C3 C 0.26478(6) 0.01201(7) 0.37884(13) Uani 0.0210(2) 4 1 d
C4 C 0.21953(6) -0.07529(7) 0.32091(15) Uani 0.0216(2) 4 1 d
C5 C 0.28227(7) -0.15559(7) 0.27510(14) Uani 0.0207(2) 4 1 d
C6 C 0.39051(7) -0.14828(6) 0.28561(13) Uani 0.01751(19) 4 1 d
C7 C 0.60725(5) 0.02777(5) 0.35094(14) Uani 0.01441(16) 4 1 d
C8 C 0.70767(6) -0.00785(6) 0.36874(12) Uani 0.01510(18) 4 1 d
C9 C 0.81016(6) 0.03669(6) 0.36722(12) Uani 0.01559(18) 4 1 d
C10 C 0.83502(5) 0.12998(6) 0.32706(13) Uani 0.01453(16) 4 1 d
C11 C 0.76210(7) 0.21055(7) 0.26884(15) Uani 0.0185(2) 4 1 d
C12 C 1.01145(7) 0.15578(7) 0.10497(15) Uani 0.0209(2) 4 1 d
N1 N 0.54551(5) -0.05295(5) 0.35998(12) Uani 0.01482(15) 4 1 d
N2 N 0.60416(5) -0.13523(6) 0.38477(13) Uani 0.02066(19) 4 1 d
N3 N 0.70177(6) -0.10787(5) 0.39069(13) Uani 0.02048(19) 4 1 d
H5 H 0.2494(11) -0.2135(11) 0.231(2) Uiso 0.028(4) 4 1 d
H111 H 0.7154(10) 0.1872(10) 0.1774(18) Uiso 0.015(3) 4 1 d
H7 H 0.5826(9) 0.0909(10) 0.345(2) Uiso 0.026(3) 4 1 d
H4 H 0.1490(10) -0.0819(9) 0.315(2) Uiso 0.025(3) 4 1 d
H2 H 0.4073(9) 0.0795(9) 0.438(2) Uiso 0.021(3) 4 1 d
H112 H 0.7961(12) 0.2604(11) 0.216(2) Uiso 0.033(4) 4 1 d
H113 H 0.7281(11) 0.2297(12) 0.369(3) Uiso 0.041(4) 4 1 d
H9 H 0.8640(10) -0.0078(9) 0.4024(19) Uiso 0.019(3) 4 1 d
H121 H 0.9959(10) 0.0911(11) 0.052(2) Uiso 0.021(3) 4 1 d
H6 H 0.4308(12) -0.2034(11) 0.248(2) Uiso 0.029(3) 4 1 d
H3 H 0.2246(11) 0.0639(11) 0.417(2) Uiso 0.027(4) 4 1 d
H122 H 0.9727(11) 0.2090(12) 0.036(2) Uiso 0.029(4) 4 1 d
H123 H 1.0856(13) 0.1705(11) 0.109(3) Uiso 0.034(4) 4 1 d
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
S 0.1246 0.1234 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 117.67(4)
O1 S1 C10 109.36(4)
O1 S1 C12 108.34(5)
O2 S1 C10 108.33(4)
O2 S1 C12 108.29(5)
C10 S1 C12 103.99(4)
C2 C1 C6 121.77(7)
C2 C1 N1 119.34(7)
C6 C1 N1 118.89(7)
C1 C2 C3 118.43(8)
C1 C2 H2 118.6(7)
C3 C2 H2 122.9(7)
C2 C3 C4 120.64(8)
C2 C3 H3 118.1(9)
C4 C3 H3 121.1(9)
C3 C4 C5 120.11(8)
C3 C4 H4 120.9(8)
C5 C4 H4 118.9(8)
C4 C5 C6 120.30(8)
C4 C5 H5 118.3(9)
C6 C5 H5 121.3(9)
C1 C6 C5 118.74(8)
C1 C6 H6 123.2(9)
C5 C6 H6 118.0(9)
C8 C7 N1 104.69(6)
C8 C7 H7 130.9(8)
N1 C7 H7 124.2(8)
C7 C8 C9 134.22(7)
C7 C8 N3 107.93(6)
C9 C8 N3 117.85(7)
C8 C9 C10 127.94(7)
C8 C9 H9 112.8(7)
C10 C9 H9 119.2(7)
S1 C10 C9 115.47(6)
S1 C10 C11 117.29(6)
C9 C10 C11 127.22(7)
C10 C11 H111 109.9(8)
C10 C11 H112 111.8(10)
C10 C11 H113 107.6(12)
H111 C11 H112 106.1(13)
H111 C11 H113 110.5(13)
H112 C11 H113 111.0(15)
S1 C12 H121 109.0(9)
S1 C12 H122 107.5(9)
S1 C12 H123 105.3(11)
H121 C12 H122 111.0(12)
H121 C12 H123 113.4(12)
H122 C12 H123 110.3(12)
C1 N1 C7 129.26(6)
C1 N1 N2 120.10(6)
C7 N1 N2 110.64(6)
N1 N2 N3 107.31(7)
C8 N3 N2 109.41(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4430(8)
S1 O2 1.4458(8)
S1 C10 1.7678(7)
S1 C12 1.7607(11)
C1 C2 1.3935(11)
C1 C6 1.3936(12)
C1 N1 1.4273(9)
C2 C3 1.3954(12)
C2 H2 0.967(13)
C3 C4 1.3852(14)
C3 H3 0.917(14)
C4 C5 1.3953(13)
C4 H4 0.908(13)
C5 C6 1.3909(12)
C5 H5 0.948(15)
C6 H6 0.949(15)
C7 C8 1.3796(10)
C7 N1 1.3551(10)
C7 H7 0.917(13)
C8 C9 1.4450(10)
C8 N3 1.3729(11)
C9 C10 1.3404(11)
C9 H9 0.951(12)
C10 C11 1.4990(12)
C11 H111 0.940(13)
C11 H112 0.889(16)
C11 H113 0.87(2)
C12 H121 0.979(14)
C12 H122 1.008(16)
C12 H123 0.970(16)
N1 N2 1.3601(10)
N2 N3 1.3042(10)
#BEGIN Loops that were not found in dictionaries:
loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
1 0.95(4) 1 0 0 0 1 0 0 0 1
2 0.05(4) -1 0 0 0 -1 0 0 0 -1
#END Loops that were not found in dictionaries
