#------------------------------------------------------------------------------
#$Date: 2019-11-24 05:37:09 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236845 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/22/7702200.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_7702200
loop_
_publ_author_name
'Hawes, Chris S.'
'Ó Máille, Gearóid M'
'Byrne, Kevin'
'Schmitt, Wolfgang'
'Gunnlaugsson, Thorfinnur'
_publ_section_title
;
 Tetraarylpyrrolo[3,2-b]pyrroles as versatile and responsive fluorescent
 linkers in metal-organic frameworks.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10080
_journal_page_last               10092
_journal_paper_doi               10.1039/c8dt01784k
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         '4(C2 H6 O S), C38 H26 N6 O4'
_chemical_formula_sum            'C46 H50 N6 O8 S4'
_chemical_formula_weight         943.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-04-28 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                84.9420(10)
_cell_angle_beta                 81.7040(10)
_cell_angle_gamma                88.700(2)
_cell_formula_units_Z            1
_cell_length_a                   5.5946(3)
_cell_length_b                   11.5848(6)
_cell_length_c                   18.1469(9)
_cell_measurement_reflns_used    3376
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.09
_cell_measurement_theta_min      2.76
_cell_volume                     1159.24(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      119.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11850
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.366
_diffrn_reflns_theta_min         1.765
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0383 before and 0.0333 after correction.
The Ratio of minimum to maximum transmission is 0.9268.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       rod
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         5789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0470P)²+0.3870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4162
_reflns_number_total             5789
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt01784k2.cif
_cod_data_source_block           H2L3
_cod_database_code               7702200
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C22(H22A,H22B,
 H22C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
S1 S 0.23988(10) 0.34816(5) 0.56495(3) 0.03537(14) Uani 1 1 d .
O3 O 0.1773(3) 0.23626(13) 0.53488(8) 0.0355(3) Uani 1 1 d .
C21 C 0.5581(4) 0.3561(2) 0.54677(17) 0.0542(7) Uani 1 1 d .
H21A H 0.6103 0.3616 0.4927 0.081 Uiso 1 1 calc GR
H21B H 0.6290 0.2864 0.5700 0.081 Uiso 1 1 calc GR
H21C H 0.6116 0.4248 0.5676 0.081 Uiso 1 1 calc GR
C20 C 0.2067(6) 0.3154(3) 0.66357(13) 0.0686(9) Uani 1 1 d .
H20A H 0.3071 0.2477 0.6753 0.103 Uiso 1 1 calc GR
H20B H 0.0371 0.2985 0.6826 0.103 Uiso 1 1 calc GR
H20C H 0.2576 0.3819 0.6871 0.103 Uiso 1 1 calc GR
S2 S 0.30211(11) 0.99865(6) 0.33151(3) 0.04341(16) Uani 1 1 d .
O4 O 0.3788(3) 0.88354(18) 0.30403(9) 0.0623(5) Uani 1 1 d .
C23 C -0.0175(4) 1.0026(2) 0.34212(13) 0.0391(5) Uani 1 1 d .
H23A H -0.0706 1.0050 0.2928 0.059 Uiso 1 1 calc GR
H23B H -0.0772 1.0718 0.3667 0.059 Uiso 1 1 calc GR
H23C H -0.0815 0.9332 0.3727 0.059 Uiso 1 1 calc GR
C22 C 0.3232(4) 0.9840(3) 0.42928(13) 0.0522(7) Uani 1 1 d .
H22A H 0.2125 0.9237 0.4543 0.078 Uiso 1 1 calc GR
H22B H 0.2796 1.0578 0.4505 0.078 Uiso 1 1 calc GR
H22C H 0.4890 0.9625 0.4367 0.078 Uiso 1 1 calc GR
O1 O 0.9947(3) 0.26826(13) 0.41226(8) 0.0352(3) Uani 1 1 d .
H1 H 1.064(5) 0.261(2) 0.4539(15) 0.053 Uiso 1 1 d R
O2 O 1.2569(2) 0.41345(13) 0.38151(7) 0.0326(3) Uani 1 1 d .
N1 N 0.6621(2) 0.56655(12) 0.05802(8) 0.0181(3) Uani 1 1 d .
N2 N 1.0563(2) 0.98437(12) 0.11741(8) 0.0183(3) Uani 1 1 d .
N3 N 1.3430(3) 1.11029(13) 0.12548(9) 0.0266(3) Uani 1 1 d .
C1 C 1.0917(3) 0.35695(16) 0.36750(10) 0.0241(4) Uani 1 1 d .
C2 C 0.9773(3) 0.38035(15) 0.29824(9) 0.0206(4) Uani 1 1 d .
C3 C 0.7665(3) 0.32543(15) 0.28850(10) 0.0221(4) Uani 1 1 d .
H3 H 0.6945 0.2693 0.3260 0.027 Uiso 1 1 calc R
C4 C 0.6613(3) 0.35225(15) 0.22438(10) 0.0205(4) Uani 1 1 d .
H4 H 0.5178 0.3140 0.2184 0.025 Uiso 1 1 calc R
C5 C 0.7632(3) 0.43496(14) 0.16815(9) 0.0179(3) Uani 1 1 d .
C6 C 0.9791(3) 0.48758(15) 0.17748(10) 0.0195(3) Uani 1 1 d .
H6 H 1.0546 0.5419 0.1394 0.023 Uiso 1 1 calc R
C7 C 1.0830(3) 0.46085(15) 0.24201(10) 0.0204(4) Uani 1 1 d .
H7 H 1.2281 0.4979 0.2479 0.025 Uiso 1 1 calc R
C8 C 0.6452(3) 0.45977(14) 0.10139(9) 0.0163(3) Uani 1 1 d .
C9 C 0.5183(3) 0.38249(15) 0.06802(9) 0.0185(3) Uani 1 1 d .
H9 H 0.4812 0.3043 0.0853 0.022 Uiso 1 1 calc R
C10 C 0.5442(3) 0.55565(14) -0.00298(9) 0.0177(3) Uani 1 1 d .
C11 C 0.7572(3) 0.67352(14) 0.07418(9) 0.0169(3) Uani 1 1 d .
C12 C 0.6639(3) 0.72680(15) 0.13773(9) 0.0192(3) Uani 1 1 d .
H12 H 0.5330 0.6927 0.1711 0.023 Uiso 1 1 calc R
C13 C 0.7614(3) 0.82987(15) 0.15261(9) 0.0190(3) Uani 1 1 d .
H13 H 0.6999 0.8661 0.1965 0.023 Uiso 1 1 calc R
C14 C 0.9504(3) 0.87956(14) 0.10240(9) 0.0180(3) Uani 1 1 d .
C15 C 1.0405(3) 0.82785(15) 0.03782(10) 0.0211(4) Uani 1 1 d .
H15 H 1.1672 0.8633 0.0034 0.025 Uiso 1 1 calc R
C16 C 0.9438(3) 0.72380(15) 0.02393(9) 0.0203(4) Uani 1 1 d .
H16 H 1.0054 0.6873 -0.0198 0.024 Uiso 1 1 calc R
C17 C 1.2963(3) 1.00865(16) 0.10462(11) 0.0244(4) Uani 1 1 d .
H17 H 1.4165 0.9577 0.0830 0.029 Uiso 1 1 calc R
C18 C 1.1204(3) 1.15447(15) 0.15336(10) 0.0227(4) Uani 1 1 d .
H18 H 1.0952 1.2279 0.1729 0.027 Uiso 1 1 calc R
C19 C 0.9418(3) 1.07860(15) 0.14915(10) 0.0215(4) Uani 1 1 d .
H19 H 0.7736 1.0884 0.1648 0.026 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'
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
O3 S1 C21 105.28(11) . .
O3 S1 C20 104.44(12) . .
C21 S1 C20 98.73(15) . .
S1 C21 H21A 109.5 . .
S1 C21 H21B 109.5 . .
S1 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
S1 C20 H20A 109.5 . .
S1 C20 H20B 109.5 . .
S1 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
O4 S2 C23 106.52(12) . .
O4 S2 C22 105.45(12) . .
C23 S2 C22 95.81(11) . .
S2 C23 H23A 109.5 . .
S2 C23 H23B 109.5 . .
S2 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
S2 C22 H22A 109.5 . .
S2 C22 H22B 109.5 . .
S2 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C1 O1 H1 109.6(17) . .
C8 N1 C11 128.89(14) . .
C10 N1 C8 107.41(13) . .
C10 N1 C11 123.39(14) . .
C17 N2 C14 125.57(15) . .
C17 N2 C19 106.48(14) . .
C19 N2 C14 127.92(14) . .
C17 N3 C18 104.69(15) . .
O1 C1 C2 113.31(16) . .
O2 C1 O1 123.34(17) . .
O2 C1 C2 123.35(17) . .
C3 C2 C1 122.05(16) . .
C3 C2 C7 119.05(16) . .
C7 C2 C1 118.90(16) . .
C2 C3 H3 119.8 . .
C4 C3 C2 120.34(16) . .
C4 C3 H3 119.8 . .
C3 C4 H4 119.4 . .
C3 C4 C5 121.10(16) . .
C5 C4 H4 119.4 . .
C4 C5 C6 118.18(15) . .
C4 C5 C8 118.89(15) . .
C6 C5 C8 122.90(15) . .
C5 C6 H6 119.8 . .
C7 C6 C5 120.45(16) . .
C7 C6 H6 119.8 . .
C2 C7 H7 119.6 . .
C6 C7 C2 120.84(16) . .
C6 C7 H7 119.6 . .
N1 C8 C5 123.48(14) . .
C9 C8 N1 109.57(14) . .
C9 C8 C5 126.79(15) . .
C8 C9 H9 127.2 . .
C8 C9 C10 105.54(14) . 2_665
C10 C9 H9 127.2 2_665 .
N1 C10 C9 142.52(15) . 2_665
C10 C10 N1 107.76(18) 2_665 .
C10 C10 C9 109.71(18) 2_665 2_665
C12 C11 N1 121.22(15) . .
C16 C11 N1 118.19(15) . .
C16 C11 C12 120.59(15) . .
C11 C12 H12 120.0 . .
C11 C12 C13 120.08(15) . .
C13 C12 H12 120.0 . .
C12 C13 H13 120.4 . .
C12 C13 C14 119.17(15) . .
C14 C13 H13 120.4 . .
C13 C14 N2 120.04(15) . .
C15 C14 N2 119.07(15) . .
C15 C14 C13 120.89(15) . .
C14 C15 H15 120.3 . .
C14 C15 C16 119.49(16) . .
C16 C15 H15 120.3 . .
C11 C16 C15 119.75(16) . .
C11 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
N2 C17 H17 123.8 . .
N3 C17 N2 112.47(16) . .
N3 C17 H17 123.8 . .
N3 C18 H18 124.6 . .
C19 C18 N3 110.83(16) . .
C19 C18 H18 124.6 . .
N2 C19 H19 127.2 . .
C18 C19 N2 105.54(15) . .
C18 C19 H19 127.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.5169(16) .
S1 C21 1.766(2) .
S1 C20 1.780(2) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
S2 O4 1.4968(19) .
S2 C23 1.770(2) .
S2 C22 1.788(2) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
O1 H1 0.89(3) .
O1 C1 1.327(2) .
O2 C1 1.213(2) .
N1 C8 1.404(2) .
N1 C10 1.384(2) .
N1 C11 1.429(2) .
N2 C14 1.427(2) .
N2 C17 1.360(2) .
N2 C19 1.381(2) .
N3 C17 1.311(2) .
N3 C18 1.380(2) .
C1 C2 1.492(2) .
C2 C3 1.393(2) .
C2 C7 1.394(2) .
C3 H3 0.9500 .
C3 C4 1.387(2) .
C4 H4 0.9500 .
C4 C5 1.403(2) .
C5 C6 1.403(2) .
C5 C8 1.465(2) .
C6 H6 0.9500 .
C6 C7 1.389(2) .
C7 H7 0.9500 .
C8 C9 1.386(2) .
C9 H9 0.9500 .
C9 C10 1.410(2) 2_665
C10 C9 1.410(2) 2_665
C10 C10 1.381(3) 2_665
C11 C12 1.386(2) .
C11 C16 1.386(2) .
C12 H12 0.9500 .
C12 C13 1.387(2) .
C13 H13 0.9500 .
C13 C14 1.392(2) .
C14 C15 1.388(2) .
C15 H15 0.9500 .
C15 C16 1.390(2) .
C16 H16 0.9500 .
C17 H17 0.9500 .
C18 H18 0.9500 .
C18 C19 1.360(2) .
C19 H19 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.89(3) 1.68(3) 2.5741(19) 175(3) 1_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 9.4(2) .
O1 C1 C2 C7 -171.47(16) .
O2 C1 C2 C3 -170.55(17) .
O2 C1 C2 C7 8.6(3) .
N1 C8 C9 C10 -0.32(18) 2_665
N1 C11 C12 C13 179.18(15) .
N1 C11 C16 C15 179.96(15) .
N2 C14 C15 C16 177.90(15) .
N3 C18 C19 N2 -0.2(2) .
C1 C2 C3 C4 177.91(16) .
C1 C2 C7 C6 -178.28(16) .
C2 C3 C4 C5 -0.1(3) .
C3 C2 C7 C6 0.9(3) .
C3 C4 C5 C6 1.8(3) .
C3 C4 C5 C8 179.80(16) .
C4 C5 C6 C7 -2.2(2) .
C4 C5 C8 N1 152.76(16) .
C4 C5 C8 C9 -32.5(2) .
C5 C6 C7 C2 0.8(3) .
C5 C8 C9 C10 -175.67(15) 2_665
C6 C5 C8 N1 -29.4(2) .
C6 C5 C8 C9 145.36(18) .
C7 C2 C3 C4 -1.2(3) .
C8 N1 C10 C9 179.6(2) 2_665
C8 N1 C10 C10 0.2(2) 2_665
C8 N1 C11 C12 -58.2(2) .
C8 N1 C11 C16 122.66(19) .
C8 C5 C6 C7 179.95(16) .
C10 N1 C8 C5 175.62(15) .
C10 N1 C8 C9 0.09(18) .
C10 N1 C11 C12 114.60(18) .
C10 N1 C11 C16 -64.5(2) .
C11 N1 C8 C5 -10.7(3) .
C11 N1 C8 C9 173.81(15) .
C11 N1 C10 C9 5.4(3) 2_665
C11 N1 C10 C10 -173.96(17) 2_665
C11 C12 C13 C14 1.1(3) .
C12 C11 C16 C15 0.8(3) .
C12 C13 C14 N2 -178.76(15) .
C12 C13 C14 C15 0.5(3) .
C13 C14 C15 C16 -1.3(3) .
C14 N2 C17 N3 -178.39(16) .
C14 N2 C19 C18 178.43(16) .
C14 C15 C16 C11 0.7(3) .
C16 C11 C12 C13 -1.7(3) .
C17 N2 C14 C13 139.89(18) .
C17 N2 C14 C15 -39.3(2) .
C17 N2 C19 C18 0.18(19) .
C17 N3 C18 C19 0.2(2) .
C18 N3 C17 N2 0.0(2) .
C19 N2 C14 C13 -38.0(3) .
C19 N2 C14 C15 142.73(18) .
C19 N2 C17 N3 -0.1(2) .
