Design of Near-Infrared-Absorbing Unsymmetrical Polymethine Dyes with Large Quadratic Hyperpolarizabilities
Pascal, Simon; Getmanenko, Yulia A.; Zhang, Yadong; Davydenko, Iryna; Ngo, Minh Hoang; Pilet, Guillaume; Redon, Sébastien; Bretonnière, Yann; Maury, Olivier; Ledoux-Rak, Isabelle; Barlow, Stephen; Marder, Seth R.; Andraud, Chantal; Chemistry of Materials 30 (2018) 3410–; doi:10.1021/acs.chemmater.8b00960

data_4003098
_publ_section_title
;
 Design of Near-Infrared-Absorbing Unsymmetrical Polymethine Dyes with
 Large Quadratic Hyperpolarizabilities
;
_journal_issue                   10
_journal_name_full               'Chemistry of Materials'
_journal_page_first              3410
_journal_paper_doi               10.1021/acs.chemmater.8b00960
_journal_volume                  30
_journal_year                    2018
_chemical_formula_moiety         'C56 H61 Cl1 N3 O2'
_chemical_formula_sum            'C56 H61 Cl N3 O2'
_chemical_formula_weight         843.57
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                78.844(4)
_cell_angle_beta                 82.313(5)
_cell_angle_gamma                64.432(6)
_cell_formula_units_Z            2
_cell_length_a                   12.8656(9)
_cell_length_b                   13.6192(7)
_cell_length_c                   15.3699(9)
_cell_measurement_reflns_used    6230
_cell_measurement_temperature    293
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3
_cell_volume                     2379.6(3)
_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      293
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19696
_diffrn_reflns_theta_full        25.169
_diffrn_reflns_theta_max         29.267
_diffrn_reflns_theta_min         2.890
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             902
_exptl_crystal_size_max          0.745
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.146
_refine_diff_density_max         1.00
_refine_diff_density_min         -0.48
_refine_ls_extinction_coef       80(30)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9399
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         5703
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.1144
_refine_ls_shift/su_max          0.0002019
_refine_ls_shift/su_mean         0.0000117
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 5.73 2.21 3.92 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1330
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.0997
_reflns_limit_h_max              16
_reflns_limit_h_min              -15
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                6950
_reflns_number_total             10938
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.1014
_oxford_refine_ls_scale          1.561(5)
_oxford_reflns_number_all        10929
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            cm8b00960_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        2379.6(2)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C56 H61 Cl1 N3 O2'
_cod_database_code               4003098
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  11,X'S) H   ( 112,X'S) H   ( 111,X'S) H   ( 113,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) H   ( 123,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 233,X'S) H   ( 232,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 243,X'S) H   ( 242,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 392,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) H   ( 412,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) H   ( 442,X'S) 
RIDE C   (  45,X'S) H   ( 452,X'S) H   ( 451,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) H   ( 472,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) H   ( 492,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) H   ( 512,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 542,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) H   ( 552,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) H   ( 622,X'S) H   ( 623,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.010000 = C(22) TO C(23) 
U(IJ)'S  0.0, 0.010000 = C(22) TO C(25) 
U(IJ)'S  0.0, 0.010000 = C(22) TO C(24) 
PLANAR 0.010000  C(2) C(3) C(20) C(21) C(26) C(27) 
END                                                                             
;