#------------------------------------------------------------------------------
#$Date: 2019-01-11 01:21:49 +0200 (Fri, 11 Jan 2019) $
#$Revision: 212899 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/27/7122779.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_7122779
loop_
_publ_author_name
'Zhang, Chengkai'
'Zhao, Yanqian'
'Li, Dandan'
'Liu, Jiejie'
'Han, Heguo'
'He, Daoyu'
'Tian, Xiaohe'
'Li, Shengli'
'Wu, Jieying'
'Tian, Yupeng'
_publ_section_title
;
 Aggregation-induced emission (AIE)-active molecules bearing singlet
 oxygen generation activities: the tunable singlet-triplet energy gap
 matters
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09230C
_journal_year                    2019
_chemical_formula_moiety         '4(C32 H34 N3 O4), 8(F6 P)'
_chemical_formula_sum            'C128 H136 F48 N12 O16 P8'
_chemical_formula_weight         3258.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-31
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-11-09 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.143(8)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   19.940(10)
_cell_length_b                   21.080(11)
_cell_length_c                   8.921(5)
_cell_measurement_reflns_used    1067
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.91
_cell_measurement_theta_min      2.52
_cell_volume                     3636(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12642
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.429
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1321 before and 0.0607 after correction.
The Ratio of minimum to maximum transmission is 0.8076.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       block
_exptl_crystal_F_000             1668
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0007(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1946
_refine_ls_R_factor_gt           0.1000
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2738
_refine_ls_wR_factor_ref         0.3297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1314
_reflns_number_total             3173
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc09230c2.cif
_cod_data_source_block           20180522w_0m
_cod_database_code               7122779
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C17(H17), C14(H14), C8(H8), C7(H7), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.5493(3) 0.9315(2) 0.6085(7) 0.1237(18) Uani 1 1 d . . .
O2 O 0.6016(4) 0.8483(3) 0.7285(8) 0.176(3) Uani 1 1 d . . .
N1 N 0.5000 0.4339(2) 0.2500 0.0630(15) Uani 1 2 d S T P
N2 N 0.6390(3) 0.3248(2) 0.5508(7) 0.0939(17) Uani 1 1 d . . .
C12 C 0.5463(2) 0.4677(2) 0.3565(6) 0.0595(13) Uani 1 1 d . . .
C10 C 0.5000 0.5678(3) 0.2500 0.0599(18) Uani 1 2 d S T P
C11 C 0.5482(2) 0.5325(2) 0.3594(6) 0.0671(14) Uani 1 1 d . . .
H11 H 0.5816 0.5533 0.4342 0.081 Uiso 1 1 calc R . .
C9 C 0.5000 0.6384(3) 0.2500 0.068(2) Uani 1 2 d S T P
C5 C 0.5000 0.8377(3) 0.2500 0.080(2) Uani 1 2 d S T P
C13 C 0.5957(3) 0.4283(2) 0.4691(6) 0.0669(14) Uani 1 1 d . . .
C17 C 0.6418(3) 0.4519(3) 0.5964(7) 0.0804(16) Uani 1 1 d . . .
H17 H 0.6447 0.4955 0.6132 0.096 Uiso 1 1 calc R . .
C14 C 0.5960(3) 0.3624(3) 0.4494(8) 0.0848(18) Uani 1 1 d . . .
H14 H 0.5658 0.3442 0.3640 0.102 Uiso 1 1 calc R . .
C8 C 0.5381(3) 0.6725(2) 0.3712(7) 0.0828(17) Uani 1 1 d . . .
H8 H 0.5650 0.6509 0.4555 0.099 Uiso 1 1 calc R . .
C7 C 0.5383(3) 0.7381(3) 0.3733(8) 0.095(2) Uani 1 1 d . . .
H7 H 0.5648 0.7590 0.4595 0.114 Uiso 1 1 calc R . .
C6 C 0.5000 0.7738(4) 0.2500 0.082(2) Uani 1 2 d S T P
C15 C 0.6813(4) 0.3482(4) 0.6720(9) 0.100(2) Uani 1 1 d . . .
H15 H 0.7101 0.3207 0.7402 0.120 Uiso 1 1 calc R . .
C16 C 0.6850(3) 0.4105(4) 0.7028(7) 0.103(2) Uani 1 1 d . . .
H16 H 0.7152 0.4261 0.7915 0.123 Uiso 1 1 calc R . .
C1 C 0.5956(4) 0.9038(4) 0.7168(10) 0.116(3) Uani 1 1 d . . .
C4 C 0.5467(4) 0.8751(3) 0.3747(10) 0.111(2) Uani 1 1 d . . .
H4A H 0.5880 0.8510 0.4201 0.133 Uiso 1 1 calc R . .
H4B H 0.5603 0.9142 0.3329 0.133 Uiso 1 1 calc R . .
C2 C 0.6345(4) 0.9510(3) 0.8370(9) 0.120(2) Uani 1 1 d . . .
H2A H 0.6566 0.9823 0.7872 0.180 Uiso 1 1 calc GR . .
H2B H 0.6688 0.9289 0.9134 0.180 Uiso 1 1 calc GR . .
H2C H 0.6025 0.9715 0.8861 0.180 Uiso 1 1 calc GR . .
C18 C 0.6357(4) 0.2554(3) 0.5194(11) 0.139(3) Uani 1 1 d . . .
H18A H 0.5900 0.2402 0.5156 0.208 Uiso 1 1 calc GR . .
H18B H 0.6684 0.2339 0.6001 0.208 Uiso 1 1 calc GR . .
H18C H 0.6466 0.2475 0.4221 0.208 Uiso 1 1 calc GR . .
C3 C 0.5083(4) 0.8891(4) 0.4918(11) 0.131(3) Uani 1 1 d . . .
H3A H 0.4645 0.9091 0.4434 0.157 Uiso 1 1 calc R . .
H3B H 0.4988 0.8501 0.5402 0.157 Uiso 1 1 calc R . .
P1 P 0.74241(10) 0.62630(9) 0.7086(2) 0.0969(8) Uani 1 1 d . . .
F1 F 0.7546(4) 0.5810(3) 0.5807(7) 0.222(3) Uani 1 1 d . . .
F2 F 0.8244(3) 0.6264(3) 0.7766(7) 0.178(2) Uani 1 1 d . . .
F3 F 0.7504(6) 0.6834(3) 0.6280(11) 0.283(5) Uani 1 1 d . . .
F4 F 0.7367(3) 0.6595(3) 0.8580(9) 0.204(3) Uani 1 1 d . . .
F5 F 0.6620(3) 0.6158(3) 0.6587(8) 0.198(3) Uani 1 1 d . . .
F6 F 0.7420(3) 0.5607(3) 0.8038(7) 0.190(2) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1020 0.0940 '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
C1 O1 C3 115.3(7) . .
C12 N1 C12 116.5(5) . 2_655
C14 N2 C18 117.5(6) . .
C15 N2 C14 121.1(6) . .
C15 N2 C18 121.4(6) . .
N1 C12 C11 123.4(5) . .
N1 C12 C13 114.1(4) . .
C11 C12 C13 122.5(5) . .
C11 C10 C11 116.1(6) 2_655 .
C11 C10 C9 122.0(3) 2_655 .
C11 C10 C9 122.0(3) . .
C12 C11 C10 120.3(5) . .
C8 C9 C10 121.8(3) 2_655 .
C8 C9 C10 121.8(3) . .
C8 C9 C8 116.3(7) 2_655 .
C6 C5 C4 122.0(3) . .
C6 C5 C4 122.0(3) . 2_655
C4 C5 C4 116.0(7) 2_655 .
C17 C13 C12 124.1(5) . .
C17 C13 C14 116.3(5) . .
C14 C13 C12 119.6(5) . .
C13 C17 C16 120.5(6) . .
N2 C14 C13 121.5(6) . .
C9 C8 C7 122.5(6) . .
C8 C7 C6 122.0(6) . .
C5 C6 C7 122.6(4) . .
C5 C6 C7 122.6(4) . 2_655
C7 C6 C7 114.7(7) . 2_655
N2 C15 C16 122.4(6) . .
C15 C16 C17 118.2(6) . .
O1 C1 C2 112.1(7) . .
O2 C1 O1 123.4(8) . .
O2 C1 C2 124.1(8) . .
C3 C4 C5 107.4(6) . .
O1 C3 C4 109.4(6) . .
F1 P1 F2 87.2(4) . .
F1 P1 F5 92.1(4) . .
F1 P1 F6 83.2(4) . .
F2 P1 F6 86.4(3) . .
F3 P1 F1 95.3(5) . .
F3 P1 F2 87.8(5) . .
F3 P1 F4 95.4(5) . .
F3 P1 F5 102.0(5) . .
F3 P1 F6 174.1(5) . .
F4 P1 F1 167.9(4) . .
F4 P1 F2 87.5(3) . .
F4 P1 F5 91.3(3) . .
F4 P1 F6 85.6(4) . .
F5 P1 F2 170.3(4) . .
F5 P1 F6 83.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.301(8) .
O1 C3 1.461(8) .
O2 C1 1.178(8) .
N1 C12 1.354(5) 2_655
N1 C12 1.354(5) .
N2 C14 1.342(7) .
N2 C15 1.295(8) .
N2 C18 1.487(8) .
C12 C11 1.368(7) .
C12 C13 1.478(7) .
C10 C11 1.404(6) .
C10 C11 1.404(6) 2_655
C10 C9 1.489(9) .
C9 C8 1.365(6) 2_655
C9 C8 1.365(6) .
C5 C6 1.345(10) .
C5 C4 1.490(8) .
C5 C4 1.490(8) 2_655
C13 C17 1.368(7) .
C13 C14 1.401(7) .
C17 C16 1.417(8) .
C8 C7 1.382(7) .
C7 C6 1.397(7) .
C6 C7 1.397(7) 2_655
C15 C16 1.341(9) .
C1 C2 1.528(10) .
C4 C3 1.469(10) .
P1 F1 1.553(6) .
P1 F2 1.598(6) .
P1 F3 1.431(7) .
P1 F4 1.534(6) .
P1 F5 1.572(6) .
P1 F6 1.625(6) .
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
N1 C12 C11 C10 1.0(7) . .
N1 C12 C13 C17 -172.5(4) . .
N1 C12 C13 C14 6.5(7) . .
N2 C15 C16 C17 -1.2(10) . .
C12 N1 C12 C11 -0.5(3) 2_655 .
C12 N1 C12 C13 -179.8(4) 2_655 .
C12 C13 C17 C16 176.9(5) . .
C12 C13 C14 N2 -178.6(5) . .
C10 C9 C8 C7 -179.6(4) . .
C11 C12 C13 C17 8.3(8) . .
C11 C12 C13 C14 -172.8(5) . .
C11 C10 C11 C12 -0.5(3) 2_655 .
C11 C10 C9 C8 -12.1(4) . .
C11 C10 C9 C8 167.9(4) 2_655 .
C11 C10 C9 C8 167.9(4) . 2_655
C11 C10 C9 C8 -12.1(4) 2_655 2_655
C9 C10 C11 C12 179.5(3) . .
C9 C8 C7 C6 -0.8(9) . .
C5 C4 C3 O1 -174.0(6) . .
C13 C12 C11 C10 -179.8(4) . .
C13 C17 C16 C15 2.5(9) . .
C17 C13 C14 N2 0.5(8) . .
C14 N2 C15 C16 -0.4(10) . .
C14 C13 C17 C16 -2.1(8) . .
C8 C9 C8 C7 0.4(4) 2_655 .
C8 C7 C6 C5 -179.6(4) . .
C8 C7 C6 C7 0.4(4) . 2_655
C6 C5 C4 C3 -93.0(6) . .
C15 N2 C14 C13 0.8(9) . .
C1 O1 C3 C4 -83.1(8) . .
C4 C5 C6 C7 6.5(5) 2_655 2_655
C4 C5 C6 C7 6.5(5) . .
C4 C5 C6 C7 -173.5(5) . 2_655
C4 C5 C6 C7 -173.5(5) 2_655 .
C4 C5 C4 C3 87.0(6) 2_655 .
C18 N2 C14 C13 -179.7(6) . .
C18 N2 C15 C16 -179.9(6) . .
C3 O1 C1 O2 -5.3(12) . .
C3 O1 C1 C2 -178.0(6) . .
