#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:17:22 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222578 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/40/4034019.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_4034019
loop_
_publ_author_name
'Rémond, Maxime'
'Zheng, Zheng'
'Jeanneau, Erwann'
'Andraud, Chantal'
'Bretonnière, Yann'
'Redon, Sébastien'
_publ_section_title
;
 4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for
 NIR-Emitting Push-Pull Dipolar Fluorophores.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9965
_journal_page_last               9974
_journal_paper_doi               10.1021/acs.joc.9b01120
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C17 H13 N3 O S'
_chemical_formula_sum            'C17 H13 N3 O S'
_chemical_formula_weight         307.37
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 102.100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4060(10)
_cell_length_b                   6.8190(7)
_cell_length_c                   10.5170(10)
_cell_measurement_reflns_used    2299
_cell_measurement_temperature    150
_cell_measurement_theta_max      66.8630
_cell_measurement_theta_min      4.2980
_cell_volume                     729.69(13)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4240
_diffrn_reflns_theta_full        66.988
_diffrn_reflns_theta_max         66.992
_diffrn_reflns_theta_min         4.299
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.009
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       25.6(15)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0511
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1413
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.0002690
_refine_ls_shift/su_mean         0.0000146
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.260E+04 0.443E+04 0.280E+04 0.121E+04 295. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1290
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1290
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1289
_reflns_number_total             1413
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.45
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0464
_oxford_refine_ls_scale          7.3(4)
_oxford_reflns_number_all        1413
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            jo9b01120_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 1 21/m 1 '
_cod_database_code               4034019
_iucr_refine_instruction_details_constraints
;
#
# Punched on 10/04/13 at 18:49:09
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE N   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 10/04/13 at 18:49:09
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z
x,-y+1/2,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.59904(5) 0.2500 0.31970(5) 0.0347 1.0000 Uani S T
C2 C 0.4323(2) 0.2500 0.3113(2) 0.0325 1.0000 Uani S T
N3 N 0.39958(19) 0.2500 0.43235(18) 0.0313 1.0000 Uani S T
C4 C 0.5120(2) 0.2500 0.5344(2) 0.0322 1.0000 Uani S T
C5 C 0.6288(2) 0.2500 0.4892(2) 0.0330 1.0000 Uani S T
C6 C 0.7506(2) 0.250000(7) 0.5723(2) 0.0390 1.0000 Uani S T
C7 C 0.7553(3) 0.250000(7) 0.7046(2) 0.0405 1.0000 Uani S T
C8 C 0.6396(3) 0.250000(7) 0.7509(2) 0.0396 1.0000 Uani S T
C9 C 0.5176(2) 0.250000(7) 0.6690(2) 0.0361 1.0000 Uani S T
H91 H 0.4410 0.2500 0.7008 0.0434 1.0000 Uiso RS .
H81 H 0.6439 0.2500 0.8401 0.0470 1.0000 Uiso RS .
H71 H 0.8359 0.2500 0.7628 0.0486 1.0000 Uiso RS .
H61 H 0.8294 0.2500 0.5417 0.0463 1.0000 Uiso RS .
C10 C 0.2668(2) 0.2500 0.4483(2) 0.0347 1.0000 Uani S T
N11 N 0.2458(2) 0.250000(7) 0.5636(2) 0.0474 1.0000 Uani S T
H111 H 0.1615 0.2500 0.5689 0.0564 1.0000 Uiso RS .
C12 C 0.1684(2) 0.2500 0.3272(2) 0.0357 1.0000 Uani S T
C13 C 0.2065(2) 0.2500 0.2102(2) 0.0355 1.0000 Uani S T
C14 C 0.3375(2) 0.2500 0.1997(2) 0.0334 1.0000 Uani S T
C15 C 0.3422(3) 0.2500 0.0629(3) 0.0442 1.0000 Uani S T
C16 C 0.1992(3) 0.2500 -0.0099(2) 0.0428 1.0000 Uani S T
O17 O 0.12233(16) 0.2500 0.09423(16) 0.0426 1.0000 Uani S T
C18 C 0.1610(2) 0.0659(3) -0.08819(19) 0.0570 1.0000 Uani . .
H183 H 0.1846 -0.0485 -0.0352 0.0828 1.0000 Uiso R .
H182 H 0.0675 0.0642 -0.1242 0.0846 1.0000 Uiso R .
H181 H 0.2084 0.0625 -0.1577 0.0838 1.0000 Uiso R .
C19 C 0.4429(3) 0.250000(6) 0.0063(3) 0.0837 1.0000 Uani S T
H191 H 0.4293 0.2500 -0.0822 0.0995 1.0000 Uiso RS .
H192 H 0.5318 0.2500 0.0530 0.0994 1.0000 Uiso RS .
C20 C 0.0340(3) 0.2500 0.3361(2) 0.0441 1.0000 Uani S T
N21 N -0.0732(2) 0.2500 0.3460(2) 0.0603 1.0000 Uani S T
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 C5 . 90.79(11) yes
S1 . C2 N3 . 113.12(17) yes
S1 . C2 C14 . 125.76(19) yes
N3 . C2 C14 . 121.1(2) yes
C2 . N3 C4 . 111.97(18) yes
C2 . N3 C10 . 122.60(19) yes
C4 . N3 C10 . 125.43(18) yes
N3 . C4 C5 . 112.56(19) yes
N3 . C4 C9 . 128.2(2) yes
C5 . C4 C9 . 119.2(2) yes
S1 . C5 C4 . 111.57(17) yes
S1 . C5 C6 . 126.13(19) yes
C4 . C5 C6 . 122.3(2) yes
C5 . C6 C7 . 118.1(2) yes
C5 . C6 H61 . 122.2 no
C7 . C6 H61 . 119.7 no
C6 . C7 C8 . 120.2(2) yes
C6 . C7 H71 . 119.9 no
C8 . C7 H71 . 119.9 no
C7 . C8 C9 . 122.2(2) yes
C7 . C8 H81 . 119.5 no
C9 . C8 H81 . 118.3 no
C4 . C9 C8 . 118.0(2) yes
C4 . C9 H91 . 120.5 no
C8 . C9 H91 . 121.6 no
N3 . C10 N11 . 118.3(2) yes
N3 . C10 C12 . 114.7(2) yes
N11 . C10 C12 . 127.0(2) yes
C10 . N11 H111 . 115.2 no
C10 . C12 C13 . 120.2(2) yes
C10 . C12 C20 . 117.5(2) yes
C13 . C12 C20 . 122.3(2) yes
C12 . C13 C14 . 123.0(2) yes
C12 . C13 O17 . 124.0(2) yes
C14 . C13 O17 . 113.0(2) yes
C13 . C14 C2 . 118.4(2) yes
C13 . C14 C15 . 108.5(2) yes
C2 . C14 C15 . 133.1(2) yes
C14 . C15 C16 . 105.4(2) yes
C14 . C15 C19 . 130.4(3) yes
C16 . C15 C19 . 124.1(3) yes
C15 . C16 C18 4_555 113.08(14) yes
C15 . C16 O17 . 104.44(19) yes
C18 4_555 C16 O17 . 106.35(14) yes
C15 . C16 C18 . 113.08(14) yes
C18 4_555 C16 C18 . 112.7(2) yes
O17 . C16 C18 . 106.35(14) yes
C16 . O17 C13 . 108.64(19) yes
C16 . C18 H183 . 110.7 no
C16 . C18 H182 . 110.6 no
H183 . C18 H182 . 109.3 no
C16 . C18 H181 . 108.4 no
H183 . C18 H181 . 108.2 no
H182 . C18 H181 . 109.6 no
C15 . C19 H191 . 119.8 no
C15 . C19 H192 . 123.2 no
H191 . C19 H192 . 117.0 no
C12 . C20 N21 . 178.6(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 . 1.718(2) yes
S1 C5 . 1.744(2) yes
C2 N3 . 1.386(3) yes
C2 C14 . 1.366(3) yes
N3 C4 . 1.412(3) yes
N3 C10 . 1.427(3) yes
C4 C5 . 1.394(3) yes
C4 C9 . 1.404(3) yes
C5 C6 . 1.381(3) yes
C6 C7 . 1.382(3) yes
C6 H61 . 0.941 no
C7 C8 . 1.390(4) yes
C7 H71 . 0.929 no
C8 C9 . 1.377(3) yes
C8 H81 . 0.929 no
C9 H91 . 0.927 no
C10 N11 . 1.277(3) yes
C10 C12 . 1.457(3) yes
N11 H111 . 0.891 no
C12 C13 . 1.369(3) yes
C12 C20 . 1.422(4) yes
C13 C14 . 1.390(3) yes
C13 O17 . 1.345(3) yes
C14 C15 . 1.450(3) yes
C15 C16 . 1.525(4) yes
C15 C19 . 1.309(4) yes
C16 C18 4_555 1.508(2) yes
C16 O17 . 1.486(3) yes
C16 C18 . 1.508(2) yes
C18 H183 . 0.960 no
C18 H182 . 0.967 no
C18 H181 . 0.964 no
C19 H191 . 0.911 no
C19 H192 . 0.952 no
C20 N21 . 1.142(4) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 H91 N11 . 120.00 0.927 2.231 2.813(2) yes
C6 H61 N21 1_655 145.23(8) 0.941 2.478 3.295(2) yes
