#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:57:40 +0200 (mar 06 de oct de 2020) $
#$Revision: 257714 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/97/7059708.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_7059708
loop_
_publ_author_name
'Ergun, Selin'
'Casselman, Matthew D.'
'Kaur, Aman Preet'
'Attanayake, N. Harsha'
'Parkin, Sean R.'
'Odom, Susan A.'
_publ_section_title
;
 Improved synthesis of N-ethyl-3,7-bis(trifluoromethyl)phenothiazine
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11349
_journal_page_last               11355
_journal_paper_doi               10.1039/D0NJ00184H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C16 H11 F6 N S, Cl6 Sb'
_chemical_formula_sum            'C16 H11 Cl6 F6 N S Sb'
_chemical_formula_weight         697.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2014/7 and CIFFIX'
_audit_update_record
;
2016-05-26 deposited with the CCDC.	2020-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.8648(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7969(2)
_cell_length_b                   26.2133(6)
_cell_length_c                   10.1713(2)
_cell_measurement_reflns_used    5518
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2350.42(9)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         1.554
_diffrn_source                   'fine-focus sealed-tube'
_exptl_absorpt_coefficient_mu    1.998
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_description       block
_exptl_crystal_F_000             1348
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0404P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4278
_reflns_number_total             5397
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj00184h2.cif
_cod_data_source_block           k15121
_cod_depositor_comments
;Adding full bibliography for 7059707--7059708.cif.

 Adding full bibliography for 7059707--7059708.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7059708
_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   0.635
_shelx_estimated_absorpt_t_max   0.754
_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.8165(2) 0.60467(8) 0.5767(2) 0.0223(4) Uani 1 1 d . . . . .
S1 S 1.01907(7) 0.69909(2) 0.59997(7) 0.02664(14) Uani 1 1 d . . . . .
C1 C 0.7513(3) 0.64429(10) 0.4782(3) 0.0236(5) Uani 1 1 d . . . . .
C2 C 0.5989(3) 0.64122(10) 0.3715(3) 0.0285(6) Uani 1 1 d . . . . .
H2 H 0.5408 0.6117 0.3672 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5342(3) 0.67989(11) 0.2748(3) 0.0314(6) Uani 1 1 d . . . . .
H3 H 0.4322 0.6767 0.2030 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6147(3) 0.7238(1) 0.2795(3) 0.0297(6) Uani 1 1 d . . . . .
C5 C 0.7626(3) 0.72889(10) 0.3819(3) 0.0282(6) Uani 1 1 d . . . . .
H5 H 0.8176 0.7592 0.3858 0.034 Uiso 1 1 calc R U . . .
C6 C 0.8319(3) 0.68913(10) 0.4806(3) 0.0247(5) Uani 1 1 d . . . . .
C7 C 1.0736(3) 0.63956(10) 0.6740(2) 0.0231(5) Uani 1 1 d . . . . .
C8 C 1.2305(3) 0.63297(10) 0.7556(3) 0.0264(6) Uani 1 1 d . . . . .
H8 H 1.2977 0.6602 0.7638 0.032 Uiso 1 1 calc R U . . .
C9 C 1.2875(3) 0.58726(10) 0.8237(3) 0.0262(6) Uani 1 1 d . . . . .
C10 C 1.1877(3) 0.54783(10) 0.8142(3) 0.0262(6) Uani 1 1 d . . . . .
H10 H 1.2271 0.5165 0.8627 0.031 Uiso 1 1 calc R U . . .
C11 C 1.0339(3) 0.55366(9) 0.7360(3) 0.0239(5) Uani 1 1 d . . . . .
H11 H 0.9683 0.5264 0.7319 0.029 Uiso 1 1 calc R U . . .
C12 C 0.9715(3) 0.59975(10) 0.6613(2) 0.0211(5) Uani 1 1 d . . . . .
C13 C 0.7149(3) 0.56289(10) 0.5804(3) 0.0272(6) Uani 1 1 d . . . . .
H13A H 0.6147 0.5774 0.5615 0.033 Uiso 1 1 calc R U . . .
H13B H 0.7585 0.5474 0.6791 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6938(3) 0.5216(1) 0.4675(3) 0.0316(6) Uani 1 1 d . . . . .
H14A H 0.6481 0.5366 0.3694 0.047 Uiso 1 1 calc R U . . .
H14B H 0.6271 0.4948 0.4739 0.047 Uiso 1 1 calc R U . . .
H14C H 0.7926 0.5068 0.4866 0.047 Uiso 1 1 calc R U . . .
C15 C 0.5376(3) 0.76564(13) 0.1658(3) 0.0374(7) Uani 1 1 d . . . . .
F1 F 0.5073(2) 0.74888(8) 0.03405(18) 0.0556(5) Uani 1 1 d . . . . .
F2 F 0.4073(2) 0.77871(7) 0.16698(18) 0.0512(5) Uani 1 1 d . . . . .
F3 F 0.6235(2) 0.80670(8) 0.1910(2) 0.0595(5) Uani 1 1 d . . . . .
C16 C 1.4639(3) 0.57964(10) 0.9086(3) 0.0311(6) Uani 1 1 d . . . . .
F4 F 1.5317(2) 0.61996(9) 0.9032(3) 0.1061(11) Uani 1 1 d . . . . .
F5 F 1.4984(2) 0.56855(11) 1.0422(2) 0.0836(8) Uani 1 1 d . . . . .
F6 F 1.5029(2) 0.54186(10) 0.8525(2) 0.0784(8) Uani 1 1 d . . . . .
Sb1 Sb 0.04466(2) 0.87990(2) -0.32408(2) 0.02202(6) Uani 1 1 d . . . . .
Cl1 Cl -0.01281(7) 0.92379(3) -0.14978(7) 0.02921(14) Uani 1 1 d . . . . .
Cl2 Cl 0.09990(7) 0.83422(3) -0.49664(7) 0.03085(15) Uani 1 1 d . . . . .
Cl3 Cl 0.24797(7) 0.93728(3) -0.28200(7) 0.03193(15) Uani 1 1 d . . . . .
Cl4 Cl -0.15815(8) 0.82379(3) -0.36779(7) 0.03295(15) Uani 1 1 d . . . . .
Cl5 Cl -0.11813(7) 0.93550(2) -0.50749(6) 0.02882(14) Uani 1 1 d . . . . .
Cl6 Cl 0.21128(8) 0.82642(3) -0.13738(8) 0.03862(17) 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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
C12 N1 C1 123.5(2) . . ?
C12 N1 C13 118.6(2) . . ?
C1 N1 C13 117.7(2) . . ?
C7 S1 C6 101.77(13) . . ?
N1 C1 C6 122.2(2) . . ?
N1 C1 C2 120.7(2) . . ?
C6 C1 C2 117.1(2) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 C15 120.8(3) . . ?
C3 C4 C15 118.9(2) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 S1 115.3(2) . . ?
C1 C6 S1 123.69(19) . . ?
C8 C7 C12 120.9(2) . . ?
C8 C7 S1 115.0(2) . . ?
C12 C7 S1 124.1(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 C16 119.7(2) . . ?
C10 C9 C16 120.8(2) . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N1 C12 C7 121.9(2) . . ?
N1 C12 C11 120.8(2) . . ?
C7 C12 C11 117.3(2) . . ?
N1 C13 C14 112.0(2) . . ?
N1 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F1 C15 F3 108.2(2) . . ?
F1 C15 F2 107.7(2) . . ?
F3 C15 F2 108.8(2) . . ?
F1 C15 C4 110.4(2) . . ?
F3 C15 C4 112.0(2) . . ?
F2 C15 C4 109.7(2) . . ?
F4 C16 F5 109.6(3) . . ?
F4 C16 F6 111.3(3) . . ?
F5 C16 F6 107.7(3) . . ?
F4 C16 C9 110.1(2) . . ?
F5 C16 C9 109.2(2) . . ?
F6 C16 C9 108.9(2) . . ?
Cl6 Sb1 Cl4 90.65(3) . . ?
Cl6 Sb1 Cl5 178.37(3) . . ?
Cl4 Sb1 Cl5 90.74(2) . . ?
Cl6 Sb1 Cl2 89.68(2) . . ?
Cl4 Sb1 Cl2 89.49(2) . . ?
Cl5 Sb1 Cl2 91.18(2) . . ?
Cl6 Sb1 Cl1 89.60(2) . . ?
Cl4 Sb1 Cl1 89.33(2) . . ?
Cl5 Sb1 Cl1 89.56(2) . . ?
Cl2 Sb1 Cl1 178.61(2) . . ?
Cl6 Sb1 Cl3 90.00(3) . . ?
Cl4 Sb1 Cl3 179.35(3) . . ?
Cl5 Sb1 Cl3 88.61(2) . . ?
Cl2 Sb1 Cl3 90.51(2) . . ?
Cl1 Sb1 Cl3 90.68(2) . . ?
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
N1 C12 1.386(3) . ?
N1 C1 1.390(3) . ?
N1 C13 1.492(3) . ?
S1 C7 1.714(3) . ?
S1 C6 1.721(3) . ?
C1 C6 1.410(4) . ?
C1 C2 1.415(3) . ?
C2 C3 1.361(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(4) . ?
C4 C15 1.532(4) . ?
C5 C6 1.400(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.403(3) . ?
C7 C12 1.412(4) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(3) . ?
C9 C16 1.572(4) . ?
C10 C11 1.371(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(3) . ?
C11 H11 0.9500 . ?
C13 C14 1.525(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 F1 1.315(3) . ?
C15 F3 1.320(4) . ?
C15 F2 1.327(3) . ?
C16 F4 1.262(3) . ?
C16 F5 1.282(3) . ?
C16 F6 1.282(3) . ?
Sb1 Cl6 2.3520(7) . ?
Sb1 Cl4 2.3532(7) . ?
Sb1 Cl5 2.3563(6) . ?
Sb1 Cl2 2.3740(6) . ?
Sb1 Cl1 2.3780(6) . ?
Sb1 Cl3 2.3810(6) . ?
