#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:52:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180521 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/90/7219016.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_7219016
loop_
_publ_author_name
'Ghosh, Sirina'
'Bedi, Anjan'
'Zade, Sanjio S.'
_publ_section_title
;
 Thienopyrrole and Selenophenopyrrole Donor Fused with Benzotriazole
 Acceptor: Microwave Assisted Synthesis and Electrochemical Polymerization
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA14850A
_journal_year                    2014
_chemical_formula_moiety         'C22 H23 N5 S2'
_chemical_formula_sum            'C22 H23 N5 S2'
_chemical_formula_weight         421.59
_chemical_name_systematic        methylthienopyrrole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-31
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2014-08-27 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.452(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5447(4)
_cell_length_b                   14.8256(5)
_cell_length_c                   15.3905(6)
_cell_measurement_reflns_used    2482
_cell_measurement_temperature    295.73(10)
_cell_measurement_theta_max      26.7440
_cell_measurement_theta_min      2.5780
_cell_volume                     2126.62(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.73(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9160
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9845
_diffrn_measured_fraction_theta_max 0.9845
_diffrn_measurement_details
;
  1 omega   57.00   95.00   1.0000   40.8500
omega____ theta____ kappa____ phi______ frames
    -       27.5074 -128.0000  153.0000 38

  2 omega  -48.00   50.00   1.0000   40.8500
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -38.0000  -60.0000 98

  3 omega  -22.00   63.00   1.0000   40.8500
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -57.0000   30.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0297867000
_diffrn_orient_matrix_UB_12      0.0016859000
_diffrn_orient_matrix_UB_13      -0.0463654000
_diffrn_orient_matrix_UB_21      0.0685806000
_diffrn_orient_matrix_UB_22      0.0102193000
_diffrn_orient_matrix_UB_23      -0.0082165000
_diffrn_orient_matrix_UB_31      0.0139232000
_diffrn_orient_matrix_UB_32      -0.0467069000
_diffrn_orient_matrix_UB_33      -0.0034562000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7193
_diffrn_reflns_theta_full        26.996159
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.93
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3167
_exptl_crystal_description       plate
_exptl_crystal_F_000             889.2461
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane-DCM'
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.307021
_refine_diff_density_min         -0.454207
_refine_diff_density_rms         0.075553
_refine_ls_d_res_high            0.782862
_refine_ls_d_res_low             10.554282
_refine_ls_goodness_of_fit_ref   1.075578
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075578
_refine_ls_R_factor_all          0.086826
_refine_ls_R_factor_gt           0.058301
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0546P)²+0.8365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.156560
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -12
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -8
_reflns_number_gt                3011
_reflns_number_total             4473
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4ra14850a2.cif
_cod_data_source_block           Methyle
_cod_original_cell_volume        2126.61(15)
_cod_database_code               7219016
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         C22H23N5S2
_reflns_odcompleteness_completeness 98.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-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_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
C1 C 0.0016(3) 0.2802(2) 0.2527(2) 0.0598(8) Uani 1.000000 .
H1a H -0.0812(3) 0.2841(2) 0.2797(2) 0.0717(9) Uiso 1.000000 R
H1b H -0.0027(3) 0.2227(2) 0.2221(2) 0.0717(9) Uiso 1.000000 R
C2 C -0.0046(3) 0.3558(2) 0.1860(2) 0.0633(8) Uani 1.000000 .
H2a H 0.0090(3) 0.4129(2) 0.2175(2) 0.0760(10) Uiso 1.000000 R
H2b H 0.0733(3) 0.3485(2) 0.1553(2) 0.0760(10) Uiso 1.000000 R
C3 C -0.1455(3) 0.3582(2) 0.1182(2) 0.0609(8) Uani 1.000000 .
H3a H -0.1658(3) 0.2983(2) 0.0933(2) 0.0731(9) Uiso 1.000000 R
H3b H -0.2216(3) 0.3741(2) 0.1482(2) 0.0731(9) Uiso 1.000000 R
C4 C -0.1470(3) 0.4243(2) 0.0430(2) 0.0624(8) Uani 1.000000 .
H4a H -0.1219(3) 0.4837(2) 0.0679(2) 0.0748(10) Uiso 1.000000 R
H4b H -0.0744(3) 0.4066(2) 0.0109(2) 0.0748(10) Uiso 1.000000 R
C5 C -0.2903(4) 0.4295(2) -0.0215(2) 0.0755(10) Uani 1.000000 .
H5a H -0.3173(4) 0.3695(2) -0.0442(2) 0.0906(12) Uiso 1.000000 R
H5b H -0.3620(4) 0.4497(2) 0.0103(2) 0.0906(12) Uiso 1.000000 R
C6 C -0.2917(5) 0.4915(3) -0.0983(3) 0.1142(16) Uani 1.000000 .
H6a H -0.227(3) 0.4692(13) -0.1331(13) 0.171(2) Uiso 1.000000 G
H6b H -0.3869(10) 0.4943(19) -0.1346(13) 0.171(2) Uiso 1.000000 G
H6c H -0.262(4) 0.5507(7) -0.0765(3) 0.171(2) Uiso 1.000000 G
C7 C 0.7771(4) 0.1130(2) 0.3252(2) 0.0718(9) Uani 1.000000 .
H7 H 0.8308(4) 0.0754(2) 0.2966(2) 0.0862(11) Uiso 1.000000 R
C8 C 0.8339(4) 0.1553(2) 0.4028(2) 0.0689(9) Uani 1.000000 .
H8 H 0.9289(4) 0.1506(2) 0.4336(2) 0.0827(11) Uiso 1.000000 R
C9 C 0.7267(3) 0.20801(19) 0.43031(19) 0.0537(7) Uani 1.000000 .
C10 C 0.5947(3) 0.20269(18) 0.37387(18) 0.0508(7) Uani 1.000000 .
C11 C 0.4983(3) 0.25669(17) 0.40969(17) 0.0469(6) Uani 1.000000 .
C12 C 0.5802(3) 0.29643(18) 0.48866(17) 0.0465(6) Uani 1.000000 .
C13 C 0.5113(3) 0.36046(17) 0.53666(16) 0.0471(7) Uani 1.000000 .
C14 C 0.3612(3) 0.37379(17) 0.51149(17) 0.0477(7) Uani 1.000000 .
C15 C 0.3263(3) 0.44048(18) 0.56869(18) 0.0528(7) Uani 1.000000 .
C16 C 0.4523(4) 0.46805(18) 0.62423(17) 0.0536(7) Uani 1.000000 .
C17 C 0.4354(4) 0.5423(2) 0.67989(19) 0.0643(9) Uani 1.000000 .
H17 H 0.5095(4) 0.5697(2) 0.72050(19) 0.0771(11) Uiso 1.000000 R
C18 C 0.2963(4) 0.5671(2) 0.6651(2) 0.0725(10) Uani 1.000000 .
H18 H 0.2641(4) 0.6143(2) 0.6954(2) 0.0870(12) Uiso 1.000000 R
C19 C 0.2811(3) 0.33019(18) 0.43428(17) 0.0475(6) Uani 1.000000 .
C20 C 0.3505(3) 0.27474(17) 0.38252(17) 0.0462(6) Uani 1.000000 .
C21 C 0.8403(4) 0.2710(3) 0.5776(2) 0.0780(10) Uani 1.000000 .
H21a H 0.8916(16) 0.3261(8) 0.5740(8) 0.1170(15) Uiso 1.000000 G
H21b H 0.8045(4) 0.2709(16) 0.6313(2) 0.1170(15) Uiso 1.000000 G
H21c H 0.9036(14) 0.2207(9) 0.5780(9) 0.1170(15) Uiso 1.000000 G
C22 C 0.7136(3) 0.4426(2) 0.6463(2) 0.0644(8) Uani 1.000000 .
H22a H 0.7515(8) 0.4001(9) 0.6925(10) 0.0966(12) Uiso 1.000000 G
H22b H 0.7700(6) 0.4409(14) 0.6017(4) 0.0966(12) Uiso 1.000000 G
H22c H 0.7168(4) 0.5021(6) 0.6711(13) 0.0966(12) Uiso 1.000000 G
N1 N 0.2539(3) 0.24653(15) 0.31038(15) 0.0516(6) Uani 1.000000 .
N2 N 0.1315(3) 0.28398(16) 0.32182(15) 0.0529(6) Uani 1.000000 .
N3 N 0.1406(3) 0.33572(16) 0.39425(15) 0.0539(6) Uani 1.000000 .
N4 N 0.5666(3) 0.41919(15) 0.60654(14) 0.0516(6) Uani 1.000000 .
N5 N 0.7204(3) 0.26416(16) 0.50102(15) 0.0530(6) Uani 1.000000 .
S1 S 0.59820(9) 0.13408(5) 0.28379(5) 0.0640(3) Uani 1.000000 .
S2 S 0.18278(10) 0.50397(6) 0.58510(5) 0.0679(3) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1b C1 H1a 107.9
C2 C1 H1a 109.26(17)
C2 C1 H1b 109.26(16)
N2 C1 H1a 109.26(15)
N2 C1 H1b 109.26(15)
N2 C1 C2 111.8(2)
H2a C2 C1 109.07(16)
H2b C2 C1 109.07(17)
H2b C2 H2a 107.8
C3 C2 C1 112.6(3)
C3 C2 H2a 109.07(17)
C3 C2 H2b 109.07(17)
H3a C3 C2 108.80(17)
H3b C3 C2 108.80(17)
H3b C3 H3a 107.7
C4 C3 C2 113.8(3)
C4 C3 H3a 108.80(17)
C4 C3 H3b 108.80(17)
H4a C4 C3 108.94(17)
H4b C4 C3 108.94(17)
H4b C4 H4a 107.8
C5 C4 C3 113.2(3)
C5 C4 H4a 108.94(19)
C5 C4 H4b 108.94(18)
H5a C5 C4 108.80(19)
H5b C5 C4 108.80(18)
H5b C5 H5a 107.7
C6 C5 C4 113.8(3)
C6 C5 H5a 108.8(2)
C6 C5 H5b 108.8(2)
H6a C6 C5 109.5
H6b C6 C5 109.5
H6b C6 H6a 109.5
H6c C6 C5 109.5
H6c C6 H6a 109.5
H6c C6 H6b 109.5
C8 C7 H7 122.60(19)
S1 C7 H7 122.60(11)
S1 C7 C8 114.8(2)
H8 C8 C7 125.06(19)
C9 C8 C7 109.9(3)
C9 C8 H8 125.1(2)
C10 C9 C8 113.7(3)
N5 C9 C8 136.2(3)
N5 C9 C10 110.1(2)
C11 C10 C9 107.8(2)
S1 C10 C9 111.7(2)
S1 C10 C11 140.5(2)
C12 C11 C10 106.4(3)
C20 C11 C10 133.2(3)
C20 C11 C12 120.4(2)
C13 C12 C11 118.8(3)
N5 C12 C11 108.0(2)
N5 C12 C13 133.2(3)
C14 C13 C12 119.8(2)
N4 C13 C12 131.7(3)
N4 C13 C14 108.5(2)
C15 C14 C13 106.7(2)
C19 C14 C13 119.7(2)
C19 C14 C15 133.1(3)
C16 C15 C14 107.7(3)
S2 C15 C14 140.8(3)
S2 C15 C16 111.2(2)
C17 C16 C15 113.9(3)
N4 C16 C15 110.0(2)
N4 C16 C17 135.9(3)
H17 C17 C16 124.9(2)
C18 C17 C16 110.1(3)
C18 C17 H17 124.94(19)
H18 C18 C17 122.72(19)
S2 C18 C17 114.6(2)
S2 C18 H18 122.72(12)
C20 C19 C14 120.3(3)
N3 C19 C14 130.9(2)
N3 C19 C20 108.6(2)
C19 C20 C11 120.5(3)
N1 C20 C11 130.5(2)
N1 C20 C19 109.0(2)
H21b C21 H21a 109.5
H21c C21 H21a 109.5
H21c C21 H21b 109.5
N5 C21 H21a 109.5
N5 C21 H21b 109.5
N5 C21 H21c 109.5
H22b C22 H22a 109.5
H22c C22 H22a 109.5
H22c C22 H22b 109.5
N4 C22 H22a 109.5
N4 C22 H22b 109.5
N4 C22 H22c 109.5
N2 N1 C20 103.0(2)
N1 N2 C1 121.3(2)
N3 N2 C1 121.6(2)
N3 N2 N1 116.4(2)
N2 N3 C19 102.9(2)
C16 N4 C13 107.1(2)
C22 N4 C13 130.3(2)
C22 N4 C16 121.7(2)
C12 N5 C9 107.6(2)
C21 N5 C9 121.3(2)
C21 N5 C12 130.4(2)
C10 S1 C7 89.93(15)
C18 S2 C15 90.22(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 H1a 0.9700
C1 H1b 0.9700
C1 C2 1.512(4)
C1 N2 1.451(4)
C2 H2a 0.9700
C2 H2b 0.9700
C2 C3 1.514(4)
C3 H3a 0.9700
C3 H3b 0.9700
C3 C4 1.514(4)
C4 H4a 0.9700
C4 H4b 0.9700
C4 C5 1.509(4)
C5 H5a 0.9700
C5 H5b 0.9700
C5 C6 1.495(5)
C6 H6a 0.9600
C6 H6b 0.9600
C6 H6c 0.9600
C7 H7 0.9300
C7 C8 1.355(5)
C7 S1 1.718(4)
C8 H8 0.9300
C8 C9 1.423(4)
C9 C10 1.369(4)
C9 N5 1.382(3)
C10 C11 1.418(4)
C10 S1 1.726(3)
C11 C12 1.423(4)
C11 C20 1.407(4)
C12 C13 1.446(4)
C12 N5 1.395(3)
C13 C14 1.415(4)
C13 N4 1.396(3)
C14 C15 1.410(4)
C14 C19 1.422(4)
C15 C16 1.378(4)
C15 S2 1.725(3)
C16 C17 1.425(4)
C16 N4 1.385(4)
C17 H17 0.9300
C17 C18 1.349(5)
C18 H18 0.9300
C18 S2 1.729(4)
C19 C20 1.406(3)
C19 N3 1.352(4)
C20 N1 1.348(3)
C21 H21a 0.9600
C21 H21b 0.9600
C21 H21c 0.9600
C21 N5 1.459(4)
C22 H22a 0.9600
C22 H22b 0.9600
C22 H22c 0.9600
C22 N4 1.446(4)
N1 N2 1.339(3)
N2 N3 1.340(3)
