#------------------------------------------------------------------------------
#$Date: 2019-11-24 13:33:00 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238019 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/46/1554641.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_1554641
loop_
_publ_author_name
'Yang, Jie'
'Gao, Heqi'
'Wang, Yunsheng'
'Yu, Yun'
'Gong, Yanbin'
'Fang, Manman'
'Ding, Dan'
'Hu, Wenping'
'Tang, Ben Zhong'
'Li, Zhen'
_publ_section_title
;
 The odd--even effect of alkyl chain in organic room temperature
 phosphorescence luminogens and the corresponding in vivo imaging
;
_journal_issue                   7
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              1391
_journal_paper_doi               10.1039/C9QM00108E
_journal_volume                  3
_journal_year                    2019
_chemical_formula_sum            'C17 H19 N O2 S'
_chemical_formula_weight         301.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc212fbx
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-15 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.331(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.377(3)
_cell_length_b                   9.712(3)
_cell_length_c                   13.362(4)
_cell_measurement_reflns_used    6202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.14
_cell_measurement_theta_min      2.25
_cell_volume                     1470.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13816
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.225
_diffrn_reflns_theta_min         2.250
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0358
_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)+(0.0563P)²+0.6198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3437
_reflns_number_total             3948
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9qm00108e2.cif
_cod_data_source_block           mo_170329h_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1554641
_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. 
;
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.58362(11) 0.17836(13) 0.50057(9) 0.0147(2) Uani 1 1 d . .
C2 C 0.64774(11) 0.10922(15) 0.43020(10) 0.0187(3) Uani 1 1 d . .
H2 H 0.6386 0.1364 0.3616 0.022 Uiso 1 1 calc R U
C3 C 0.72385(11) 0.00213(15) 0.45983(10) 0.0204(3) Uani 1 1 d . .
H3 H 0.7654 -0.0432 0.4108 0.024 Uiso 1 1 calc R U
C4 C 0.74091(11) -0.04061(14) 0.55953(11) 0.0196(3) Uani 1 1 d . .
H4 H 0.7931 -0.1143 0.5788 0.024 Uiso 1 1 calc R U
C5 C 0.68017(11) 0.02650(13) 0.62979(10) 0.0165(2) Uani 1 1 d . .
H5 H 0.6911 -0.0006 0.6983 0.020 Uiso 1 1 calc R U
C6 C 0.60266(11) 0.13412(13) 0.60085(9) 0.0142(2) Uani 1 1 d . .
C7 C 0.41805(11) 0.29665(13) 0.63150(9) 0.0146(2) Uani 1 1 d . .
C8 C 0.32783(11) 0.33829(14) 0.68940(10) 0.0184(3) Uani 1 1 d . .
H8 H 0.3312 0.3144 0.7585 0.022 Uiso 1 1 calc R U
C9 C 0.23369(12) 0.41438(15) 0.64569(11) 0.0214(3) Uani 1 1 d . .
H9 H 0.1721 0.4437 0.6842 0.026 Uiso 1 1 calc R U
C10 C 0.23138(12) 0.44700(15) 0.54387(11) 0.0217(3) Uani 1 1 d . .
H10 H 0.1675 0.4998 0.5134 0.026 Uiso 1 1 calc R U
C11 C 0.31908(12) 0.40487(14) 0.48617(10) 0.0194(3) Uani 1 1 d . .
H11 H 0.3139 0.4281 0.4168 0.023 Uiso 1 1 calc R U
C12 C 0.41639(11) 0.32774(13) 0.52861(9) 0.0150(2) Uani 1 1 d . .
C13 C 0.51203(12) 0.34585(14) 0.36998(9) 0.0179(3) Uani 1 1 d . .
H13A H 0.5962 0.3511 0.3571 0.022 Uiso 1 1 calc R U
H13B H 0.4815 0.4413 0.3710 0.022 Uiso 1 1 calc R U
C14 C 0.44496(11) 0.26927(14) 0.28282(9) 0.0168(2) Uani 1 1 d . .
H14A H 0.4615 0.1694 0.2892 0.020 Uiso 1 1 calc R U
H14B H 0.3591 0.2831 0.2852 0.020 Uiso 1 1 calc R U
C15 C 0.48148(11) 0.32118(14) 0.18253(9) 0.0159(2) Uani 1 1 d . .
H15A H 0.5686 0.3182 0.1838 0.019 Uiso 1 1 calc R U
H15B H 0.4563 0.4182 0.1730 0.019 Uiso 1 1 calc R U
C16 C 0.42739(11) 0.23543(14) 0.09430(9) 0.0168(2) Uani 1 1 d . .
H16A H 0.4467 0.1372 0.1070 0.020 Uiso 1 1 calc R U
H16B H 0.3404 0.2450 0.0896 0.020 Uiso 1 1 calc R U
C17 C 0.47138(13) 0.27809(16) -0.00553(10) 0.0223(3) Uani 1 1 d . .
H17A H 0.4567 0.3766 -0.0167 0.033 Uiso 1 1 calc R U
H17B H 0.4294 0.2253 -0.0602 0.033 Uiso 1 1 calc R U
H17C H 0.5563 0.2598 -0.0038 0.033 Uiso 1 1 calc R U
N1 N 0.50468(9) 0.28445(11) 0.47026(8) 0.0152(2) Uani 1 1 d . .
O1 O 0.62200(9) 0.33490(12) 0.72875(8) 0.0290(3) Uani 1 1 d . .
O2 O 0.50963(11) 0.13003(12) 0.77150(8) 0.0304(3) Uani 1 1 d . .
S1 S 0.54284(3) 0.22447(3) 0.69564(2) 0.01702(10) 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 0.0033 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
N1 C1 C6 122.58(11)
N1 C1 C2 120.92(11)
C6 C1 C2 116.50(12)
C3 C2 C1 120.91(12)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 121.65(12)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 118.44(12)
C5 C4 H4 120.8
C3 C4 H4 120.8
C4 C5 C6 120.51(12)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 121.98(11)
C5 C6 S1 117.20(9)
C1 C6 S1 120.43(10)
C8 C7 C12 122.27(12)
C8 C7 S1 116.83(10)
C12 C7 S1 120.36(10)
C9 C8 C7 119.91(12)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C10 118.44(12)
C8 C9 H9 120.8
C10 C9 H9 120.8
C11 C10 C9 121.95(13)
C11 C10 H10 119.0
C9 C10 H10 119.0
C10 C11 C12 120.95(12)
C10 C11 H11 119.5
C12 C11 H11 119.5
N1 C12 C7 122.53(11)
N1 C12 C11 121.00(12)
C7 C12 C11 116.47(11)
N1 C13 C14 115.44(11)
N1 C13 H13A 108.4
C14 C13 H13A 108.4
N1 C13 H13B 108.4
C14 C13 H13B 108.4
H13A C13 H13B 107.5
C15 C14 C13 110.60(10)
C15 C14 H14A 109.5
C13 C14 H14A 109.5
C15 C14 H14B 109.5
C13 C14 H14B 109.5
H14A C14 H14B 108.1
C14 C15 C16 112.04(11)
C14 C15 H15A 109.2
C16 C15 H15A 109.2
C14 C15 H15B 109.2
C16 C15 H15B 109.2
H15A C15 H15B 107.9
C17 C16 C15 112.71(11)
C17 C16 H16A 109.0
C15 C16 H16A 109.0
C17 C16 H16B 109.0
C15 C16 H16B 109.0
H16A C16 H16B 107.8
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C12 N1 C1 122.43(10)
C12 N1 C13 119.41(11)
C1 N1 C13 118.06(10)
O2 S1 O1 116.98(8)
O2 S1 C6 109.76(7)
O1 S1 C6 108.92(6)
O2 S1 C7 110.36(7)
O1 S1 C7 108.04(7)
C6 S1 C7 101.68(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.4017(17)
C1 C6 1.4047(17)
C1 C2 1.4124(17)
C2 C3 1.387(2)
C2 H2 0.9500
C3 C4 1.392(2)
C3 H3 0.9500
C4 C5 1.3799(18)
C4 H4 0.9500
C5 C6 1.3986(18)
C5 H5 0.9500
C6 S1 1.7313(13)
C7 C8 1.4012(18)
C7 C12 1.4060(17)
C7 S1 1.7365(13)
C8 C9 1.3848(19)
C8 H8 0.9500
C9 C10 1.395(2)
C9 H9 0.9500
C10 C11 1.3785(19)
C10 H10 0.9500
C11 C12 1.4112(18)
C11 H11 0.9500
C12 N1 1.3925(16)
C13 N1 1.4760(16)
C13 C14 1.5254(18)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.5251(17)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.5257(18)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C17 1.5249(18)
C16 H16A 0.9900
C16 H16B 0.9900
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
O1 S1 1.4433(11)
O2 S1 1.4431(11)
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
N1 C1 C2 C3 -178.52(12)
C6 C1 C2 C3 0.90(18)
C1 C2 C3 C4 -0.6(2)
C2 C3 C4 C5 -0.2(2)
C3 C4 C5 C6 0.52(19)
C4 C5 C6 C1 -0.16(19)
C4 C5 C6 S1 -173.11(10)
N1 C1 C6 C5 178.86(11)
C2 C1 C6 C5 -0.55(18)
N1 C1 C6 S1 -8.41(17)
C2 C1 C6 S1 172.19(9)
C12 C7 C8 C9 -0.9(2)
S1 C7 C8 C9 170.66(11)
C7 C8 C9 C10 0.3(2)
C8 C9 C10 C11 0.5(2)
C9 C10 C11 C12 -0.8(2)
C8 C7 C12 N1 -178.78(12)
S1 C7 C12 N1 9.96(18)
C8 C7 C12 C11 0.61(19)
S1 C7 C12 C11 -170.66(10)
C10 C11 C12 N1 179.63(12)
C10 C11 C12 C7 0.23(19)
N1 C13 C14 C15 -166.83(11)
C13 C14 C15 C16 173.14(11)
C14 C15 C16 C17 -175.04(11)
C7 C12 N1 C1 17.44(18)
C11 C12 N1 C1 -161.91(12)
C7 C12 N1 C13 -166.31(11)
C11 C12 N1 C13 14.33(18)
C6 C1 N1 C12 -18.34(18)
C2 C1 N1 C12 161.05(12)
C6 C1 N1 C13 165.37(11)
C2 C1 N1 C13 -15.25(17)
C14 C13 N1 C12 -92.04(15)
C14 C13 N1 C1 84.37(14)
C5 C6 S1 O2 -41.78(12)
C1 C6 S1 O2 145.15(11)
C5 C6 S1 O1 87.47(11)
C1 C6 S1 O1 -85.60(11)
C5 C6 S1 C7 -158.63(10)
C1 C6 S1 C7 28.30(11)
C8 C7 S1 O2 42.75(12)
C12 C7 S1 O2 -145.52(11)
C8 C7 S1 O1 -86.27(11)
C12 C7 S1 O1 85.45(12)
C8 C7 S1 C6 159.17(10)
C12 C7 S1 C6 -29.10(12)
