#------------------------------------------------------------------------------
#$Date: 2020-04-04 01:22:25 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250005 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/35/4003521.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_4003521
loop_
_publ_author_name
'Kaur, Aman Preet'
'Harris, Oliver C.'
'Attanayake, N. Harsha'
'Liang, Zhiming'
'Parkin, Sean R.'
'Tang, Maureen H.'
'Odom, Susan A.'
_publ_section_title
;
 Quantifying Environmental Effects on the Solution and Solid-State
 Stability of a Phenothiazine Radical Cation
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.9b05345
_journal_year                    2020
_chemical_formula_moiety         'C17 H19 N O2 S, B F4'
_chemical_formula_sum            'C17 H19 B F4 N O2 S'
_chemical_formula_weight         388.20
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.294(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2318(3)
_cell_length_b                   6.8098(2)
_cell_length_c                   24.3279(9)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.11
_cell_volume                     1692.28(9)
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            37261
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.450
_diffrn_reflns_theta_min         3.107
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       'cut lath'
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0297P)²+1.0881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3150
_reflns_number_total             3858
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm9b05345_si_001.cif
_cod_data_source_block           m19080
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4003521
_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. 
;
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.995
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.63161(4) 0.28675(6) 0.54440(2) 0.01312(10) Uani 1 1 d . . . . .
O1 O 0.44840(11) 0.45006(17) 0.32214(5) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.56594(11) 0.81337(17) 0.29638(5) 0.0184(3) Uani 1 1 d . . . . .
N1 N 0.49374(12) 0.22131(19) 0.42792(5) 0.0117(3) Uani 1 1 d . . . . .
C1 C 0.62615(15) 0.2719(2) 0.43066(6) 0.0120(3) Uani 1 1 d . . . . .
C2 C 0.69366(16) 0.2987(2) 0.38201(7) 0.0142(3) Uani 1 1 d . . . . .
H2 H 0.647102 0.289650 0.347175 0.017 Uiso 1 1 calc R U . . .
C3 C 0.82533(16) 0.3376(2) 0.38454(7) 0.0163(3) Uani 1 1 d . . . . .
H3 H 0.868548 0.355178 0.351359 0.020 Uiso 1 1 calc R U . . .
C4 C 0.89714(16) 0.3518(2) 0.43495(7) 0.0159(3) Uani 1 1 d . . . . .
H4 H 0.988959 0.373496 0.435965 0.019 Uiso 1 1 calc R U . . .
C5 C 0.83432(16) 0.3341(2) 0.48296(7) 0.0156(3) Uani 1 1 d . . . . .
H5 H 0.882316 0.346562 0.517382 0.019 Uiso 1 1 calc R U . . .
C6 C 0.69907(15) 0.2977(2) 0.48131(6) 0.0123(3) Uani 1 1 d . . . . .
C7 C 0.46797(15) 0.2497(2) 0.52733(6) 0.0120(3) Uani 1 1 d . . . . .
C8 C 0.38789(16) 0.2416(2) 0.57222(7) 0.0143(3) Uani 1 1 d . . . . .
H8 H 0.424099 0.267851 0.608302 0.017 Uiso 1 1 calc R U . . .
C9 C 0.25759(16) 0.1960(2) 0.56425(7) 0.0155(3) Uani 1 1 d . . . . .
H9 H 0.203984 0.186432 0.594753 0.019 Uiso 1 1 calc R U . . .
C10 C 0.20456(16) 0.1637(2) 0.51084(7) 0.0153(3) Uani 1 1 d . . . . .
H10 H 0.114282 0.132303 0.505378 0.018 Uiso 1 1 calc R U . . .
C11 C 0.28001(15) 0.1764(2) 0.46595(7) 0.0137(3) Uani 1 1 d . . . . .
H11 H 0.240724 0.157484 0.430003 0.016 Uiso 1 1 calc R U . . .
C12 C 0.41573(15) 0.2172(2) 0.47282(6) 0.0118(3) Uani 1 1 d . . . . .
C13 C 0.43288(16) 0.1545(2) 0.37416(6) 0.0134(3) Uani 1 1 d . . . . .
H13A H 0.372302 0.044870 0.380939 0.016 Uiso 1 1 calc R U . . .
H13B H 0.502570 0.102662 0.351566 0.016 Uiso 1 1 calc R U . . .
C14 C 0.35806(16) 0.3120(2) 0.34146(7) 0.0152(3) Uani 1 1 d . . . . .
H14A H 0.307295 0.251924 0.309923 0.018 Uiso 1 1 calc R U . . .
H14B H 0.296076 0.378639 0.365079 0.018 Uiso 1 1 calc R U . . .
C15 C 0.38480(16) 0.5935(3) 0.28668(7) 0.0188(4) Uani 1 1 d . . . . .
H15A H 0.334043 0.685595 0.308632 0.023 Uiso 1 1 calc R U . . .
H15B H 0.323613 0.527822 0.259553 0.023 Uiso 1 1 calc R U . . .
C16 C 0.48685(16) 0.7035(2) 0.25746(7) 0.0173(3) Uani 1 1 d . . . . .
H16A H 0.542084 0.609976 0.237979 0.021 Uiso 1 1 calc R U . . .
H16B H 0.444244 0.793113 0.229860 0.021 Uiso 1 1 calc R U . . .
C17 C 0.66635(17) 0.9179(3) 0.27101(7) 0.0211(4) Uani 1 1 d . . . . .
H17A H 0.718467 0.826247 0.250243 0.032 Uiso 1 1 calc R U . . .
H17B H 0.722924 0.982892 0.299352 0.032 Uiso 1 1 calc R U . . .
H17C H 0.626941 1.016827 0.245917 0.032 Uiso 1 1 calc R U . . .
F1 F -0.03802(10) 0.08810(16) 0.58561(4) 0.0271(3) Uani 1 1 d . . . . .
F2 F 0.04171(10) 0.18838(17) 0.67022(4) 0.0286(3) Uani 1 1 d . . . . .
F3 F -0.16676(10) 0.07026(16) 0.65815(4) 0.0253(2) Uani 1 1 d . . . . .
F4 F -0.11437(10) 0.36807(15) 0.62278(5) 0.0271(3) Uani 1 1 d . . . . .
B1 B -0.06843(18) 0.1788(3) 0.63466(8) 0.0174(4) 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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C7 103.05(8) . . ?
C14 O1 C15 111.66(12) . . ?
C17 O2 C16 111.87(12) . . ?
C12 N1 C1 124.55(13) . . ?
C12 N1 C13 117.05(12) . . ?
C1 N1 C13 118.28(12) . . ?
N1 C1 C6 122.30(14) . . ?
N1 C1 C2 120.70(14) . . ?
C6 C1 C2 117.00(14) . . ?
C3 C2 C1 120.84(15) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.26(15) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.58(15) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.06(15) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 121.10(14) . . ?
C5 C6 S1 115.31(12) . . ?
C1 C6 S1 123.59(12) . . ?
C8 C7 C12 121.05(14) . . ?
C8 C7 S1 114.93(12) . . ?
C12 C7 S1 123.91(12) . . ?
C9 C8 C7 120.33(15) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.32(15) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 121.53(15) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.63(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N1 C12 C11 120.97(14) . . ?
N1 C12 C7 121.95(14) . . ?
C11 C12 C7 117.08(14) . . ?
N1 C13 C14 114.71(13) . . ?
N1 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
N1 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
O1 C14 C13 108.90(13) . . ?
O1 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
O1 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O1 C15 C16 108.75(13) . . ?
O1 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
O1 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
O2 C16 C15 109.43(13) . . ?
O2 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
O2 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F2 B1 F1 110.02(14) . . ?
F2 B1 F4 109.80(15) . . ?
F1 B1 F4 108.72(14) . . ?
F2 B1 F3 110.44(14) . . ?
F1 B1 F3 108.47(15) . . ?
F4 B1 F3 109.35(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7202(16) . ?
S1 C7 1.7204(16) . ?
O1 C14 1.4172(19) . ?
O1 C15 1.4343(19) . ?
O2 C17 1.420(2) . ?
O2 C16 1.4224(19) . ?
N1 C12 1.3898(19) . ?
N1 C1 1.396(2) . ?
N1 C13 1.4873(19) . ?
C1 C6 1.414(2) . ?
C1 C2 1.416(2) . ?
C2 C3 1.371(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.404(2) . ?
C7 C12 1.418(2) . ?
C8 C9 1.372(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.417(2) . ?
C11 H11 0.9500 . ?
C13 C14 1.517(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.497(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
F1 B1 1.395(2) . ?
F2 B1 1.382(2) . ?
F3 B1 1.397(2) . ?
F4 B1 1.396(2) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C6 9.2(2) . . . . ?
C13 N1 C1 C6 -166.65(14) . . . . ?
C12 N1 C1 C2 -171.15(14) . . . . ?
C13 N1 C1 C2 13.0(2) . . . . ?
N1 C1 C2 C3 -176.32(14) . . . . ?
C6 C1 C2 C3 3.4(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 -2.5(2) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C4 C5 C6 C1 2.2(2) . . . . ?
C4 C5 C6 S1 -177.98(12) . . . . ?
N1 C1 C6 C5 175.18(14) . . . . ?
C2 C1 C6 C5 -4.5(2) . . . . ?
N1 C1 C6 S1 -4.6(2) . . . . ?
C2 C1 C6 S1 175.69(12) . . . . ?
C7 S1 C6 C5 178.00(12) . . . . ?
C7 S1 C6 C1 -2.16(15) . . . . ?
C6 S1 C7 C8 -177.95(12) . . . . ?
C6 S1 C7 C12 5.77(15) . . . . ?
C12 C7 C8 C9 2.0(2) . . . . ?
S1 C7 C8 C9 -174.40(12) . . . . ?
C7 C8 C9 C10 -2.0(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 C12 1.9(2) . . . . ?
C1 N1 C12 C11 175.93(14) . . . . ?
C13 N1 C12 C11 -8.2(2) . . . . ?
C1 N1 C12 C7 -5.3(2) . . . . ?
C13 N1 C12 C7 170.58(13) . . . . ?
C10 C11 C12 N1 177.01(14) . . . . ?
C10 C11 C12 C7 -1.8(2) . . . . ?
C8 C7 C12 N1 -178.89(14) . . . . ?
S1 C7 C12 N1 -2.8(2) . . . . ?
C8 C7 C12 C11 -0.1(2) . . . . ?
S1 C7 C12 C11 175.97(11) . . . . ?
C12 N1 C13 C14 85.82(17) . . . . ?
C1 N1 C13 C14 -98.02(16) . . . . ?
C15 O1 C14 C13 174.76(13) . . . . ?
N1 C13 C14 O1 69.93(17) . . . . ?
C14 O1 C15 C16 -166.69(13) . . . . ?
C17 O2 C16 C15 178.85(13) . . . . ?
O1 C15 C16 O2 -65.52(17) . . . . ?
