#------------------------------------------------------------------------------
#$Date: 2019-11-24 05:37:09 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236845 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/21/7702198.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_7702198
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         'C40 H36 N4, C7 H8'
_chemical_formula_sum            'C47 H44 N4'
_chemical_formula_weight         664.86
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-01-23 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                94.749(17)
_cell_angle_beta                 94.10(2)
_cell_angle_gamma                102.130(17)
_cell_formula_units_Z            1
_cell_length_a                   6.259(3)
_cell_length_b                   10.267(5)
_cell_length_c                   14.832(8)
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      4.44
_cell_volume                     924.8(8)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.92
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10234
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.043
_diffrn_reflns_theta_min         4.427
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0638 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.8417.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       rod
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0888P)²+0.1035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2786
_reflns_number_total             3350
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt01784k2.cif
_cod_data_source_block           L1
_cod_original_cell_volume        924.7(8)
_cod_database_code               7702198
_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   0.979
_shelx_estimated_absorpt_t_min   0.910
_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
2. Others
 Fixed Sof: C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5) C22(0.5) C23(0.5) H23(0.5)
 C24(0.5) H24(0.5) C25(0.5) H25(0.5) C26(0.5) H26(0.5) C27(0.5) H27(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8355(2) 0.06206(15) 0.17464(9) 0.0386(3) Uani 1 1 d . . . .
N2 N 0.09874(19) 0.50115(12) 0.39374(7) 0.0245(3) Uani 1 1 d . . . .
C1 C 0.7346(2) 0.12294(15) 0.21610(10) 0.0296(3) Uani 1 1 d . . . .
C2 C 0.6057(2) 0.19830(14) 0.26769(9) 0.0265(3) Uani 1 1 d . . . .
C3 C 0.4252(2) 0.23517(14) 0.22437(9) 0.0277(3) Uani 1 1 d . . . .
H3 H 0.3887 0.2119 0.1610 0.033 Uiso 1 1 calc R . . .
C4 C 0.2993(2) 0.30584(14) 0.27404(9) 0.0268(3) Uani 1 1 d . . . .
H4 H 0.1768 0.3309 0.2443 0.032 Uiso 1 1 calc R . . .
C5 C 0.3515(2) 0.34079(13) 0.36815(9) 0.0246(3) Uani 1 1 d . . . .
C6 C 0.5345(2) 0.30347(14) 0.40999(9) 0.0250(3) Uani 1 1 d . . . .
H6 H 0.5719 0.3270 0.4733 0.030 Uiso 1 1 calc R . . .
C7 C 0.6620(2) 0.23317(14) 0.36121(9) 0.0260(3) Uani 1 1 d . . . .
H7 H 0.7857 0.2089 0.3906 0.031 Uiso 1 1 calc R . . .
C8 C 0.2160(2) 0.40860(14) 0.42449(9) 0.0246(3) Uani 1 1 d . . . .
C9 C -0.0210(2) 0.53513(14) 0.46376(9) 0.0235(3) Uani 1 1 d . . . .
C10 C -0.1689(2) 0.61618(14) 0.48736(9) 0.0248(3) Uani 1 1 d . . . .
H10 H -0.2247 0.6753 0.4507 0.030 Uiso 1 1 calc R . . .
C11 C 0.1092(2) 0.56361(14) 0.31116(9) 0.0241(3) Uani 1 1 d . . . .
C12 C -0.0848(2) 0.56281(14) 0.25889(9) 0.0254(3) Uani 1 1 d . . . .
H12 H -0.2217 0.5192 0.2774 0.030 Uiso 1 1 calc R . . .
C13 C -0.0777(2) 0.62615(14) 0.17925(9) 0.0256(3) Uani 1 1 d . . . .
H13 H -0.2112 0.6259 0.1444 0.031 Uiso 1 1 calc R . . .
C14 C 0.1205(2) 0.69001(13) 0.14933(9) 0.0242(3) Uani 1 1 d . . . .
C15 C 0.3137(2) 0.68896(15) 0.20325(9) 0.0273(3) Uani 1 1 d . . . .
H15 H 0.4510 0.7313 0.1845 0.033 Uiso 1 1 calc R . . .
C16 C 0.3093(2) 0.62772(15) 0.28329(9) 0.0269(3) Uani 1 1 d . . . .
H16 H 0.4423 0.6295 0.3190 0.032 Uiso 1 1 calc R . . .
C17 C 0.1344(2) 0.75712(14) 0.06025(9) 0.0269(3) Uani 1 1 d . . . .
C18 C 0.2645(3) 0.90265(15) 0.07934(10) 0.0336(3) Uani 1 1 d . . . .
H18A H 0.1927 0.9515 0.1233 0.050 Uiso 1 1 calc GR . . .
H18B H 0.2695 0.9455 0.0227 0.050 Uiso 1 1 calc GR . . .
H18C H 0.4142 0.9037 0.1043 0.050 Uiso 1 1 calc GR . . .
C19 C 0.2518(3) 0.67866(16) -0.00598(10) 0.0325(3) Uani 1 1 d . . . .
H19A H 0.3998 0.6799 0.0210 0.049 Uiso 1 1 calc GR . . .
H19B H 0.2614 0.7203 -0.0631 0.049 Uiso 1 1 calc GR . . .
H19C H 0.1687 0.5859 -0.0180 0.049 Uiso 1 1 calc GR . . .
C20 C -0.0926(2) 0.75893(17) 0.01460(10) 0.0331(3) Uani 1 1 d . . . .
H20A H -0.1766 0.6668 -0.0006 0.050 Uiso 1 1 calc GR . . .
H20B H -0.0755 0.8039 -0.0410 0.050 Uiso 1 1 calc GR . . .
H20C H -0.1707 0.8072 0.0563 0.050 Uiso 1 1 calc GR . . .
C21 C -0.1177(16) 1.0540(9) 0.6285(6) 0.063(2) Uani 0.5 1 d . P A -1
H21A H -0.1330 0.9792 0.6662 0.094 Uiso 0.5 1 calc GR P A -1
H21B H -0.2551 1.0855 0.6240 0.094 Uiso 0.5 1 calc GR P A -1
H21C H 0.0017 1.1272 0.6561 0.094 Uiso 0.5 1 calc GR P A -1
C22 C -0.0671(9) 1.0088(4) 0.5362(3) 0.0401(10) Uani 0.5 1 d . P A -1
C23 C -0.2341(10) 0.9559(6) 0.4698(5) 0.0437(13) Uani 0.5 1 d . P A -1
H23 H -0.3815 0.9455 0.4847 0.052 Uiso 0.5 1 calc R P A -1
C24 C -0.1954(8) 0.9169(4) 0.3817(3) 0.0536(10) Uani 0.5 1 d . P A -1
H24 H -0.3160 0.8800 0.3380 0.064 Uiso 0.5 1 calc R P A -1
C25 C 0.0099(12) 0.9306(7) 0.3573(6) 0.0544(17) Uani 0.5 1 d . P A -1
H25 H 0.0353 0.9067 0.2964 0.065 Uiso 0.5 1 calc R P A -1
C26 C 0.1864(9) 0.9811(5) 0.4235(5) 0.0615(14) Uani 0.5 1 d . P A -1
H26 H 0.3333 0.9879 0.4087 0.074 Uiso 0.5 1 calc R P A -1
C27 C 0.1436(11) 1.0208(6) 0.5105(6) 0.0518(17) Uani 0.5 1 d . P A -1
H27 H 0.2638 1.0577 0.5544 0.062 Uiso 0.5 1 calc R P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
C8 N2 C11 129.14(11) .
C9 N2 C8 107.14(11) .
C9 N2 C11 123.43(12) .
N1 C1 C2 179.36(17) .
C3 C2 C1 119.80(13) .
C3 C2 C7 120.45(13) .
C7 C2 C1 119.75(13) .
C2 C3 H3 120.1 .
C4 C3 C2 119.89(13) .
C4 C3 H3 120.1 .
C3 C4 H4 119.7 .
C3 C4 C5 120.65(13) .
C5 C4 H4 119.7 .
C4 C5 C8 122.63(13) .
C6 C5 C4 118.39(12) .
C6 C5 C8 118.91(12) .
C5 C6 H6 119.2 .
C7 C6 C5 121.59(13) .
C7 C6 H6 119.2 .
C2 C7 H7 120.5 .
C6 C7 C2 119.02(13) .
C6 C7 H7 120.5 .
N2 C8 C5 124.17(12) .
C10 C8 N2 109.61(12) 2_566
C10 C8 C5 126.02(13) 2_566
N2 C9 C10 142.45(13) .
C9 C9 N2 108.33(15) 2_566
C9 C9 C10 109.22(15) 2_566
C8 C10 C9 105.69(12) 2_566
C8 C10 H10 127.2 2_566
C9 C10 H10 127.2 .
C12 C11 N2 119.11(12) .
C12 C11 C16 119.65(13) .
C16 C11 N2 121.22(13) .
C11 C12 H12 120.1 .
C11 C12 C13 119.79(13) .
C13 C12 H12 120.1 .
C12 C13 H13 119.1 .
C12 C13 C14 121.74(13) .
C14 C13 H13 119.1 .
C13 C14 C15 117.25(13) .
C13 C14 C17 122.99(13) .
C15 C14 C17 119.75(12) .
C14 C15 H15 119.1 .
C16 C15 C14 121.73(13) .
C16 C15 H15 119.1 .
C11 C16 H16 120.1 .
C15 C16 C11 119.83(13) .
C15 C16 H16 120.1 .
C14 C17 C19 108.63(12) .
C18 C17 C14 109.85(12) .
C18 C17 C19 109.58(12) .
C20 C17 C14 112.42(12) .
C20 C17 C18 107.95(12) .
C20 C17 C19 108.37(12) .
C17 C18 H18A 109.5 .
C17 C18 H18B 109.5 .
C17 C18 H18C 109.5 .
H18A C18 H18B 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
C17 C19 H19A 109.5 .
C17 C19 H19B 109.5 .
C17 C19 H19C 109.5 .
H19A C19 H19B 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C17 C20 H20A 109.5 .
C17 C20 H20B 109.5 .
C17 C20 H20C 109.5 .
H20A C20 H20B 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
H21A C21 H21B 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C22 C21 H21A 109.5 .
C22 C21 H21B 109.5 .
C22 C21 H21C 109.5 .
C23 C22 C21 120.2(6) .
C23 C22 C27 116.1(6) .
C27 C22 C21 123.7(7) .
C22 C23 H23 118.8 .
C22 C23 C24 122.4(5) .
C24 C23 H23 118.8 .
C23 C24 H24 119.5 .
C25 C24 C23 121.0(5) .
C25 C24 H24 119.5 .
C24 C25 H25 120.6 .
C24 C25 C26 118.8(6) .
C26 C25 H25 120.6 .
C25 C26 H26 120.4 .
C27 C26 C25 119.1(5) .
C27 C26 H26 120.4 .
C22 C27 C26 122.6(8) .
C22 C27 H27 118.7 .
C26 C27 H27 118.7 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.151(2) .
N2 C8 1.4025(19) .
N2 C9 1.3869(18) .
N2 C11 1.4281(19) .
C1 C2 1.445(2) .
C2 C3 1.396(2) .
C2 C7 1.404(2) .
C3 H3 0.9500 .
C3 C4 1.387(2) .
C4 H4 0.9500 .
C4 C5 1.409(2) .
C5 C6 1.402(2) .
C5 C8 1.4679(19) .
C6 H6 0.9500 .
C6 C7 1.386(2) .
C7 H7 0.9500 .
C8 C10 1.393(2) 2_566
C9 C9 1.383(3) 2_566
C9 C10 1.412(2) .
C10 C8 1.393(2) 2_566
C10 H10 0.9500 .
C11 C12 1.391(2) .
C11 C16 1.395(2) .
C12 H12 0.9500 .
C12 C13 1.394(2) .
C13 H13 0.9500 .
C13 C14 1.397(2) .
C14 C15 1.403(2) .
C14 C17 1.539(2) .
C15 H15 0.9500 .
C15 C16 1.388(2) .
C16 H16 0.9500 .
C17 C18 1.537(2) .
C17 C19 1.5410(19) .
C17 C20 1.534(2) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C21 C22 1.485(11) .
C22 C23 1.372(7) .
C22 C27 1.382(9) .
C23 H23 0.9500 .
C23 C24 1.388(9) .
C24 H24 0.9500 .
C24 C25 1.341(9) .
C25 H25 0.9500 .
C25 C26 1.405(10) .
C26 H26 0.9500 .
C26 C27 1.383(10) .
C27 H27 0.9500 .
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_1
_geom_torsion_site_symmetry_4
N2 C9 C10 C8 179.90(18) . 2_566
N2 C11 C12 C13 178.45(12) . .
N2 C11 C16 C15 -179.18(12) . .
C1 C2 C3 C4 179.05(13) . .
C1 C2 C7 C6 -178.90(13) . .
C2 C3 C4 C5 -0.1(2) . .
C3 C2 C7 C6 0.7(2) . .
C3 C4 C5 C6 0.6(2) . .
C3 C4 C5 C8 -176.38(13) . .
C4 C5 C6 C7 -0.4(2) . .
C4 C5 C8 N2 -32.9(2) . .
C4 C5 C8 C10 141.36(15) . 2_566
C5 C6 C7 C2 -0.2(2) . .
C6 C5 C8 N2 150.13(14) . .
C6 C5 C8 C10 -35.6(2) . 2_566
C7 C2 C3 C4 -0.5(2) . .
C8 N2 C9 C9 -0.09(18) . 2_566
C8 N2 C9 C10 179.38(18) . .
C8 N2 C11 C12 130.54(15) . .
C8 N2 C11 C16 -50.9(2) . .
C8 C5 C6 C7 176.65(13) . .
C9 N2 C8 C5 175.60(12) . .
C9 N2 C8 C10 0.50(16) . 2_566
C9 N2 C11 C12 -56.39(18) . .
C9 N2 C11 C16 122.12(15) . .
C9 C9 C10 C8 -0.63(19) 2_566 2_566
C11 N2 C8 C5 -10.5(2) . .
C11 N2 C8 C10 174.44(13) . 2_566
C11 N2 C9 C9 -174.47(14) . 2_566
C11 N2 C9 C10 5.0(3) . .
C11 C12 C13 C14 0.7(2) . .
C12 C11 C16 C15 -0.7(2) . .
C12 C13 C14 C15 -0.5(2) . .
C12 C13 C14 C17 178.09(12) . .
C13 C14 C15 C16 -0.3(2) . .
C13 C14 C17 C18 126.45(14) . .
C13 C14 C17 C19 -113.71(15) . .
C13 C14 C17 C20 6.22(19) . .
C14 C15 C16 C11 0.9(2) . .
C15 C14 C17 C18 -54.98(17) . .
C15 C14 C17 C19 64.87(16) . .
C15 C14 C17 C20 -175.21(12) . .
C16 C11 C12 C13 -0.1(2) . .
C17 C14 C15 C16 -178.92(12) . .
C21 C22 C23 C24 177.5(5) . .
C21 C22 C27 C26 -178.2(6) . .
C22 C23 C24 C25 -0.6(8) . .
C23 C22 C27 C26 -0.5(9) . .
C23 C24 C25 C26 2.2(8) . .
C24 C25 C26 C27 -2.9(9) . .
C25 C26 C27 C22 2.2(9) . .
C27 C22 C23 C24 -0.3(9) . .
