The design of rigid cyclic tripyrrins: the importance of intermolecular interactions on aggregation and luminescence
Wang, Jun-Fei; Yao, Yuhang; Ning, Yingying; Meng, Yin-Shan; Hou, Chun-Liang; Zhang, Jing; Zhang, Jun-Long; Organic Chemistry Frontiers 5 (2018) 1877–; doi:10.1039/C8QO00313K

data_1554306
_publ_section_title
;
 The design of rigid cyclic tripyrrins: the importance of intermolecular
 interactions on aggregation and luminescence
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1877
_journal_paper_doi               10.1039/C8QO00313K
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C34 H7 Cl2 F10 N5 O2, 0.25(C8 H16 O2)'
_chemical_formula_sum            'C36 H11 Cl2 F10 N5 O2.5'
_chemical_formula_weight         814.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-10-24 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.153(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3689(5)
_cell_length_b                   19.2075(10)
_cell_length_c                   14.4005(9)
_cell_measurement_reflns_used    2733
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      27.2340
_cell_measurement_theta_min      3.3670
_cell_volume                     1751.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -5.00   87.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6191   77.0000    0.0000 92

  2 omega  -16.00   75.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6191   57.0000  -90.0000 91

  3 omega  -39.00   53.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7128   57.0000  120.0000 92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0446983000
_diffrn_orient_matrix_UB_12      0.0142500000
_diffrn_orient_matrix_UB_13      -0.0430652000
_diffrn_orient_matrix_UB_21      -0.0479144000
_diffrn_orient_matrix_UB_22      0.0267440000
_diffrn_orient_matrix_UB_23      0.0244330000
_diffrn_orient_matrix_UB_31      0.0908283000
_diffrn_orient_matrix_UB_32      0.0211073000
_diffrn_orient_matrix_UB_33      -0.0017671000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10154
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.214
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pinkish red'
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       plate
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.569
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0683
_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/[\s^2^(Fo^2^)+(0.1371P)^2^+1.0881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2181
_refine_ls_wR_factor_ref         0.2414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2267
_reflns_number_total             3185
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00313k2.cif
_cod_data_source_block           170309
_cod_original_formula_sum        'C36 H11 Cl2 F10 N5 O2.50'
_cod_database_code               1554306
_chemical_oxdiff_formula         'C34 H9 Cl2 F10 N5 O2'
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Fixed Sof: O0AA(0.25) C1(0.25) H1A(0.25) H1B(0.25) C0AA(0.25) H0AB(0.25)
 H0AA(0.25) C2AA(0.25) H2AB(0.25) H2AA(0.25) C1AA(0.25) H1AA(0.25) H1AB(0.25)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C0AA(H0AB,H0AA), C2AA(H2AB,H2AA), C1AA(H1AA,H1AB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C24(H24), C26(H26), C47(H47)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'