#------------------------------------------------------------------------------
#$Date: 2023-05-05 04:43:39 +0300 (Fri, 05 May 2023) $
#$Revision: 283241 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/21/7712179.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_7712179
loop_
_publ_author_name
'Dionisi, Erica M.'
'Binder, Justin F.'
'LaFortune, James H. W.'
'Macdonald, Charles L. B.'
_publ_section_title
;
 A remarkably stable acyclic phosphamethine cyanine dye.
;
_journal_issue                   8
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2448
_journal_page_last               2454
_journal_paper_doi               10.1039/d2dt04085a
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         'C7 H7 N4, C F3 O3 S'
_chemical_formula_sum            'C8 H7 F3 N4 O3 S'
_chemical_formula_weight         296.24
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2022-12-13 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.304(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8689(10)
_cell_length_b                   8.0859(10)
_cell_length_c                   16.865(2)
_cell_measurement_reflns_used    3506
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      24.968
_cell_measurement_theta_min      2.938
_cell_volume                     1171.9(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1434
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28762
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.076
_diffrn_reflns_theta_max         25.076
_diffrn_reflns_theta_min         2.938
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
 wR2(int) was 0.0848 before and 0.0749 after correction. 
The Ratio of minimum to maximum transmission is 0.8501. 
The λ/2 correction factor is Not present.'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0443
_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)+(0.0417P)²+0.7455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1503
_reflns_number_total             2086
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt04085a2.cif
_cod_data_source_block           ed6
_cod_depositor_comments
'Adding full bibliography for 7712178--7712180.cif.'
_cod_original_cell_volume        1171.9(3)
_cod_database_code               7712179
_shelx_shelxl_version_number     2017/1
_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_max   0.993
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C51(H51A,H51B,H51C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.46350(8) 0.23889(9) 0.61555(4) 0.0216(2) Uani 1 1 d . . . . .
F2 F 0.19662(19) 0.3771(2) 0.54484(11) 0.0383(5) Uani 1 1 d . . . . .
F3 F 0.2543(2) 0.1666(2) 0.48090(12) 0.0400(5) Uani 1 1 d . . . . .
F1 F 0.3685(2) 0.3969(2) 0.47572(12) 0.0435(5) Uani 1 1 d . . . . .
O2 O 0.5700(2) 0.1446(3) 0.58092(13) 0.0274(5) Uani 1 1 d . . . . .
O1 O 0.5219(2) 0.3936(3) 0.65147(13) 0.0331(6) Uani 1 1 d . . . . .
O3 O 0.3779(3) 0.1418(3) 0.66040(14) 0.0386(6) Uani 1 1 d . . . . .
N2 N 0.2689(2) 0.7572(3) 0.59047(13) 0.0168(5) Uani 1 1 d . . . . .
N5 N 0.4903(2) 0.7563(3) 0.68074(14) 0.0181(5) Uani 1 1 d . . . . .
C4 C 0.3867(3) 0.6731(3) 0.71432(17) 0.0179(6) Uani 1 1 d . . . . .
N41 N 0.4719(3) 0.5206(4) 0.85168(16) 0.0371(7) Uani 1 1 d . . . . .
N31 N -0.0132(3) 0.5325(4) 0.65550(16) 0.0384(7) Uani 1 1 d . . . . .
C3 C 0.2469(3) 0.6746(3) 0.65795(16) 0.0170(6) Uani 1 1 d . . . . .
C1 C 0.4161(3) 0.8066(3) 0.60652(17) 0.0183(6) Uani 1 1 d . . . . .
H1 H 0.461271 0.868459 0.570395 0.022 Uiso 1 1 calc R . . . .
C31 C 0.1020(3) 0.5975(4) 0.65862(17) 0.0233(7) Uani 1 1 d . . . . .
C6 C 0.3142(3) 0.2986(4) 0.52488(19) 0.0239(7) Uani 1 1 d . . . . .
C41 C 0.4318(3) 0.5908(4) 0.79105(19) 0.0242(7) Uani 1 1 d . . . . .
C21 C 0.1512(3) 0.7868(4) 0.51348(17) 0.0232(7) Uani 1 1 d . . . . .
H21A H 0.106265 0.681021 0.490851 0.035 Uiso 1 1 calc GR . . . .
H21B H 0.200065 0.841103 0.474248 0.035 Uiso 1 1 calc GR . . . .
H21C H 0.068829 0.857912 0.524035 0.035 Uiso 1 1 calc GR . . . .
C51 C 0.6570(3) 0.7800(4) 0.71837(18) 0.0267(7) Uani 1 1 d . . . . .
H51A H 0.671460 0.813209 0.775643 0.040 Uiso 1 1 calc GR . . . .
H51B H 0.698078 0.866390 0.688711 0.040 Uiso 1 1 calc GR . . . .
H51C H 0.712700 0.676218 0.715818 0.040 Uiso 1 1 calc GR . . . .
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'
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
O2 S1 C6 102.28(13) . . ?
O1 S1 O2 115.37(13) . . ?
O1 S1 O3 116.09(14) . . ?
O1 S1 C6 103.63(13) . . ?
O3 S1 O2 114.15(13) . . ?
O3 S1 C6 102.61(14) . . ?
C3 N2 C21 126.6(2) . . ?
C1 N2 C3 108.1(2) . . ?
C1 N2 C21 125.3(2) . . ?
C4 N5 C51 126.3(2) . . ?
C1 N5 C4 108.3(2) . . ?
C1 N5 C51 125.4(2) . . ?
N5 C4 C41 122.7(2) . . ?
C3 C4 N5 107.1(2) . . ?
C3 C4 C41 129.9(3) . . ?
N2 C3 C31 122.0(2) . . ?
C4 C3 N2 106.9(2) . . ?
C4 C3 C31 130.9(3) . . ?
N2 C1 H1 125.3 . . ?
N5 C1 N2 109.5(2) . . ?
N5 C1 H1 125.3 . . ?
N31 C31 C3 176.5(3) . . ?
F2 C6 S1 111.4(2) . . ?
F2 C6 F3 107.0(2) . . ?
F3 C6 S1 111.2(2) . . ?
F1 C6 S1 112.56(19) . . ?
F1 C6 F2 107.5(2) . . ?
F1 C6 F3 106.8(2) . . ?
N41 C41 C4 177.3(3) . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C51 H51A 109.5 . . ?
N5 C51 H51B 109.5 . . ?
N5 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
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 O2 1.445(2) . ?
S1 O1 1.430(2) . ?
S1 O3 1.432(2) . ?
S1 C6 1.823(3) . ?
F2 C6 1.333(3) . ?
F3 C6 1.333(3) . ?
F1 C6 1.322(3) . ?
N2 C3 1.374(3) . ?
N2 C1 1.328(3) . ?
N2 C21 1.471(3) . ?
N5 C4 1.369(3) . ?
N5 C1 1.326(4) . ?
N5 C51 1.471(3) . ?
C4 C3 1.363(4) . ?
C4 C41 1.422(4) . ?
N41 C41 1.147(4) . ?
N31 C31 1.139(4) . ?
C3 C31 1.431(4) . ?
C1 H1 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
