#------------------------------------------------------------------------------
#$Date: 2020-03-05 00:34:03 +0100 (jue 05 de mar de 2020) $
#$Revision: 248812 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/58/7125879.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_7125879
loop_
_publ_author_name
'Zhuang, Jiabao'
'Yang, Hanxiao'
'Li, Yue'
'Wang, Bing'
'Li, Nan'
'Zhao, Na'
_publ_section_title
;
 Efficient photosensitizers with aggregation-induced emission
 characteristics for lysosome- and Gram-positive bacteria-targeted
 photodynamic therapy.
;
_journal_issue                   17
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2630
_journal_page_last               2633
_journal_paper_doi               10.1039/d0cc00394h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C21 H22 N3 O2'
_chemical_formula_sum            'C21 H22 N3 O2'
_chemical_formula_weight         348.41
_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             2019-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-15 deposited with the CCDC.	2020-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                112.503(4)
_cell_angle_beta                 95.468(4)
_cell_angle_gamma                100.753(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5347(3)
_cell_length_b                   11.4519(5)
_cell_length_c                   14.2937(6)
_cell_measurement_reflns_used    6391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3480
_cell_measurement_theta_min      4.2230
_cell_volume                     954.35(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00 105.00   1.00    3.48    --   37.78  77.00  60.00   94
  2  ω    -30.00  65.00   1.00    3.48    --   37.78 -77.00 -60.00   95
  3  ω     -4.00  77.00   1.00    3.48    --   37.78 -99.00-120.00   81
  4  ω     -4.00  77.00   1.00    3.48    --   37.78 -99.00-180.00   81
  5  ω    -31.00  57.00   1.00    3.48    --   37.78 -37.00-180.00   88
  6  ω     19.00 107.00   1.00    3.48    --   37.78  37.00   0.00   88
  7  ω     21.00 105.00   1.00    3.48    --   37.78  57.00 120.00   84
  8  ω     39.00 123.00   1.00   13.90    --  108.00-127.00 -64.00   84
  9  ω     87.00 178.00   1.00   13.90    --  108.00  30.00 -60.00   91
 10  ω    100.00 178.00   1.00   13.90    --  108.00 111.00  90.00   78
 11  ω     40.00 135.00   1.00   13.90    --  108.00 -77.00 120.00   95
 12  ω     38.00 116.00   1.00   13.90    --  108.00-111.00  90.00   78
 13  ω    100.00 178.00   1.00   13.90    --  108.00 111.00  60.00   78
 14  ω     38.00 129.00   1.00   13.90    --  108.00 -30.00  30.00   91
 15  ω     40.00 125.00   1.00   13.90    --  108.00 -45.00 120.00   85
 16  ω     40.00 125.00   1.00   13.90    --  108.00 -45.00 -90.00   85
 17  ω     41.00 126.00   1.00   13.90    --  108.00 -61.00   0.00   85
 18  ω     39.00 109.00   1.00   13.90    --  108.00 -94.00 -30.00   70
 19  ω     39.00 177.00   1.00   13.90    --  108.00   0.00  60.00  138
 20  ω     21.00 105.00   1.00    3.48    --   37.78  57.00-180.00   84
 21  ω     21.00 105.00   1.00    3.48    --   37.78  57.00-120.00   84
 22  ω     11.00 105.00   1.00    3.48    --   37.78  77.00 -90.00   94
 23  ω    -31.00  57.00   1.00    3.48    --   37.78 -37.00 -60.00   88
 24  ω     11.00 105.00   1.00    3.48    --   37.78  77.00 -30.00   94
 25  ω    -29.00  55.00   1.00    3.48    --   37.78 -57.00  30.00   84
 26  ω     70.00 178.00   1.00   13.90    --  108.00  15.00-150.00  108
 27  ω     87.00 178.00   1.00   13.90    --  108.00  30.00 150.00   91
 28  ω     91.00 176.00   1.00   13.90    --  108.00  45.00-150.00   85
 29  ω     81.00 176.00   1.00   13.90    --  108.00  77.00  30.00   95
 30  ω     87.00 178.00   1.00   13.90    --  108.00  30.00   0.00   91
 31  ω     91.00 176.00   1.00   13.90    --  108.00  45.00-120.00   85
 32  ω     87.00 178.00   1.00   13.90    --  108.00  30.00 -30.00   91
 33  ω     87.00 178.00   1.00   13.90    --  108.00  30.00  30.00   91
 34  ω     81.00 176.00   1.00   13.90    --  108.00  77.00  60.00   95
 35  ω     81.00 176.00   1.00   13.90    --  108.00  77.00-120.00   95
 36  ω     81.00 176.00   1.00   13.90    --  108.00  77.00 150.00   95
 37  ω     87.00 178.00   1.00   13.90    --  108.00  30.00 120.00   91
 38  ω     11.00 105.00   1.00    3.48    --   37.78  77.00-180.00   94
 39  ω     11.00 105.00   1.00    3.48    --   37.78  77.00 120.00   94
 40  ω     11.00 105.00   1.00    3.48    --   37.78  77.00-120.00   94
 41  ω     21.00 105.00   1.00    3.48    --   37.78  57.00 -30.00   84
 42  ω     11.00 105.00   1.00    3.48    --   37.78  77.00   0.00   94
 43  ω    -29.00  55.00   1.00    3.48    --   37.78 -57.00  90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0151416000
_diffrn_orient_matrix_UB_12      0.1092043000
_diffrn_orient_matrix_UB_13      0.1069849000
_diffrn_orient_matrix_UB_21      -0.0356726000
_diffrn_orient_matrix_UB_22      0.0931872000
_diffrn_orient_matrix_UB_23      -0.0507735000
_diffrn_orient_matrix_UB_31      -0.2410212000
_diffrn_orient_matrix_UB_32      -0.0438034000
_diffrn_orient_matrix_UB_33      -0.0078424000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17579
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.910
_diffrn_reflns_theta_min         4.259
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             370
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0469
_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)+(0.0791P)²+0.1681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3116
_reflns_number_total             3689
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc00394h2.cif
_cod_data_source_block           exp_15203
_cod_depositor_comments          'Adding full bibliography for 7125879.cif.'
_cod_database_code               7125879
_shelx_shelxl_version_number     2018/3
_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.
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.669
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
O1 O 0.3730(2) 0.37556(12) 0.80298(11) 0.0697(4) Uani 1 1 d .
C2 C 0.8744(2) 0.07995(12) 0.55750(10) 0.0376(3) Uani 1 1 d .
C3 C 0.8998(2) -0.03109(13) 0.57073(10) 0.0391(3) Uani 1 1 d .
H3 H 0.832280 -0.052986 0.618231 0.047 Uiso 1 1 calc R
C4 C 0.7453(2) 0.16131(13) 0.62068(10) 0.0391(3) Uani 1 1 d .
C5 C 0.8101(2) 0.29653(14) 0.66507(11) 0.0462(3) Uani 1 1 d .
H5 H 0.937433 0.337165 0.654489 0.055 Uiso 1 1 calc R
C6 C 0.9356(2) 0.21588(13) 0.45680(10) 0.0411(3) Uani 1 1 d .
H6 H 0.801017 0.231143 0.459790 0.049 Uiso 1 1 calc R
N7 N 0.1083(2) 0.87252(13) 1.06145(10) 0.0554(4) Uani 1 1 d .
C8 C 0.9770(2) 0.11086(12) 0.48460(10) 0.0381(3) Uani 1 1 d .
C9 C 0.4344(2) 0.17806(15) 0.69858(12) 0.0504(4) Uani 1 1 d .
H9 H 0.307050 0.137598 0.709257 0.060 Uiso 1 1 calc R
C10 C 0.5553(2) 0.10377(13) 0.63896(11) 0.0443(3) Uani 1 1 d .
H10 H 0.508896 0.013430 0.610410 0.053 Uiso 1 1 calc R
C11 C 0.5016(3) 0.31267(15) 0.74268(12) 0.0493(4) Uani 1 1 d .
O12 O 0.1198(3) 1.12093(13) 1.21756(10) 0.0775(4) Uani 1 1 d .
C13 C 0.9975(3) 0.37589(15) 0.38560(13) 0.0528(4) Uani 1 1 d .
C14 C 0.6890(3) 0.37221(14) 0.72484(12) 0.0517(4) Uani 1 1 d .
H14 H 0.733697 0.462609 0.752773 0.062 Uiso 1 1 calc R
C15 C 1.0720(2) 0.29214(13) 0.42752(11) 0.0446(3) Uani 1 1 d .
N16 N 0.9329(3) 0.43774(16) 0.35033(15) 0.0785(5) Uani 1 1 d .
C17 C 1.2942(3) 0.29715(16) 0.43435(14) 0.0574(4) Uani 1 1 d .
C18 C 0.1293(3) 0.73878(18) 1.02942(14) 0.0630(5) Uani 1 1 d .
H18A H -0.010293 0.680245 0.999973 0.076 Uiso 1 1 calc R
H18B H 0.183273 0.726884 1.089924 0.076 Uiso 1 1 calc R
C19 C 0.2597(3) 0.55558(18) 0.91092(15) 0.0679(5) Uani 1 1 d .
H19A H 0.284172 0.532108 0.968711 0.081 Uiso 1 1 calc R
H19B H 0.117664 0.508463 0.872855 0.081 Uiso 1 1 calc R
C20 C 0.4171(3) 0.51411(17) 0.84177(14) 0.0626(5) Uani 1 1 d .
H20A H 0.401182 0.541353 0.785586 0.075 Uiso 1 1 calc R
H20B H 0.560749 0.552737 0.880325 0.075 Uiso 1 1 calc R
C21 C 0.2738(3) 0.70063(18) 0.95154(15) 0.0667(5) Uani 1 1 d .
H21A H 0.233246 0.723212 0.894761 0.080 Uiso 1 1 calc R
H21B H 0.418824 0.748565 0.983798 0.080 Uiso 1 1 calc R
C22 C -0.0502(3) 0.89354(19) 1.12780(14) 0.0648(5) Uani 1 1 d .
H22A H -0.007486 0.876757 1.187411 0.078 Uiso 1 1 calc R
H22B H -0.185114 0.833189 1.090427 0.078 Uiso 1 1 calc R
C23 C -0.0747(3) 1.0309(2) 1.16264(15) 0.0726(5) Uani 1 1 d .
H23A H -0.123054 1.046493 1.103172 0.087 Uiso 1 1 calc R
H23B H -0.180537 1.042938 1.206397 0.087 Uiso 1 1 calc R
C24 C 0.3063(3) 0.96746(18) 1.11733(14) 0.0647(5) Uani 1 1 d .
H24A H 0.410895 0.957898 1.072863 0.078 Uiso 1 1 calc R
H24B H 0.358902 0.951731 1.176123 0.078 Uiso 1 1 calc R
N25 N 1.4697(3) 0.3029(2) 0.44062(19) 0.0907(6) Uani 1 1 d .
C26 C 0.2755(4) 1.1042(2) 1.15386(16) 0.0788(6) Uani 1 1 d .
H26A H 0.408778 1.165862 1.192151 0.095 Uiso 1 1 calc R
H26B H 0.232023 1.121822 1.094787 0.095 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 0.0181 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'
O O 0.0492 0.0322 '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
C11 O1 C20 118.69(13) . .
C3 C2 C4 119.39(11) . .
C3 C2 C8 117.82(11) . .
C8 C2 C4 122.79(11) . .
C2 C3 C8 122.50(12) . 2_756
C5 C4 C2 121.74(13) . .
C5 C4 C10 117.76(12) . .
C10 C4 C2 120.49(12) . .
C14 C5 C4 121.43(14) . .
C15 C6 C8 126.58(13) . .
C18 N7 C22 109.34(14) . .
C24 N7 C18 112.42(14) . .
C24 N7 C22 108.55(13) . .
C2 C8 C6 120.82(11) . .
C3 C8 C2 119.68(11) 2_756 .
C3 C8 C6 119.07(11) 2_756 .
C10 C9 C11 120.32(14) . .
C9 C10 C4 121.24(13) . .
O1 C11 C9 115.06(14) . .
O1 C11 C14 125.41(14) . .
C14 C11 C9 119.52(13) . .
C23 O12 C26 109.85(15) . .
N16 C13 C15 177.4(2) . .
C11 C14 C5 119.72(14) . .
C6 C15 C13 119.88(13) . .
C6 C15 C17 124.32(12) . .
C17 C15 C13 115.80(13) . .
N25 C17 C15 179.0(2) . .
N7 C18 C21 114.42(15) . .
C20 C19 C21 112.97(17) . .
O1 C20 C19 106.47(15) . .
C19 C21 C18 110.54(16) . .
N7 C22 C23 110.67(16) . .
O12 C23 C22 110.69(16) . .
N7 C24 C26 110.79(16) . .
O12 C26 C24 111.04(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.3627(17) .
O1 C20 1.426(2) .
C2 C3 1.3919(17) .
C2 C4 1.4796(17) .
C2 C8 1.4099(18) .
C3 C8 1.3966(17) 2_756
C4 C5 1.3898(19) .
C4 C10 1.390(2) .
C5 C14 1.3878(19) .
C6 C8 1.4643(17) .
C6 C15 1.339(2) .
N7 C18 1.459(2) .
N7 C22 1.461(2) .
N7 C24 1.451(2) .
C9 C10 1.3777(19) .
C9 C11 1.385(2) .
C11 C14 1.382(2) .
O12 C23 1.413(3) .
O12 C26 1.420(2) .
C13 C15 1.4400(19) .
C13 N16 1.131(2) .
C15 C17 1.435(2) .
C17 N25 1.129(2) .
C18 C21 1.518(2) .
C19 C20 1.509(2) .
C19 C21 1.516(2) .
C22 C23 1.502(3) .
C24 C26 1.509(3) .
