#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:09:12 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178837 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/91/4109165.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_4109165
loop_
_publ_author_name
'Hu Kang'
'Antonio Facchetti'
'Hua Jiang'
'Elena Cariati'
'Stefania Righetto'
'Renato Ugo'
'Cristiano Zuccaccia'
'Alceo Macchioni'
'Charlotte L. Stern'
'Zhifu Liu'
'Seng-Tiong Ho'
'Eric C. Brown'
'Mark A. Ratner'
'Tobin J. Marks'
_publ_section_title
;
 Ultralarge Hyperpolarizability Twisted π-Electron System Electro-Optic
 Chromophores: Synthesis, Solid-State and Solution-Phase Structural
 Characteristics, Electronic Structures, Linear and Nonlinear Optical
 Properties, and Computational Studies
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3267
_journal_page_last               3286
_journal_paper_doi               10.1021/ja0674690
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.32
_chemical_melting_point          468
_chemical_name_systematic
4-(4-methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridin-1-ol
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 119.049(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.018(6)
_cell_length_b                   8.137(3)
_cell_length_c                   18.221(4)
_cell_measurement_temperature    153(2)
_cell_volume                     2724.2(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12351
_diffrn_reflns_theta_full        28.96
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         2.22
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_correction_T_min  0.9383
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       cut
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.274
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0874P)²+1.3782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1552
_reflns_number_gt                2583
_reflns_number_total             3314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0674690si20061024_101346.cif
_cod_data_source_block           Compd_3
_cod_original_cell_volume        2724.1(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4109165
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.13355(7) 0.25554(14) 0.03989(7) 0.0408(3) Uani 1 1 d .
O2 O 0.10706(6) 1.15051(13) 0.38041(6) 0.0320(3) Uani 1 1 d .
N1 N 0.12758(7) 0.37767(15) 0.08277(7) 0.0281(3) Uani 1 1 d .
C1 C 0.06653(8) 0.39637(17) 0.08909(9) 0.0281(3) Uani 1 1 d .
H1 H 0.0271 0.3226 0.0598 0.034 Uiso 1 1 calc R
C2 C 0.05977(7) 0.52040(17) 0.13721(8) 0.0250(3) Uani 1 1 d .
C3 C 0.11784(7) 0.62962(16) 0.18069(8) 0.0218(3) Uani 1 1 d .
C4 C 0.17989(8) 0.61223(17) 0.17078(9) 0.0254(3) Uani 1 1 d .
C5 C 0.18305(8) 0.48619(18) 0.12169(9) 0.0275(3) Uani 1 1 d .
H5 H 0.2250 0.4754 0.1151 0.033 Uiso 1 1 calc R
C6 C -0.01047(8) 0.5329(2) 0.13985(10) 0.0333(4) Uani 1 1 d .
H6A H -0.0471 0.5882 0.0890 0.050 Uiso 1 1 calc R
H6B H -0.0025 0.5962 0.1894 0.050 Uiso 1 1 calc R
H6C H -0.0276 0.4224 0.1429 0.050 Uiso 1 1 calc R
C7 C 0.24402(9) 0.7257(2) 0.21353(11) 0.0371(4) Uani 1 1 d .
H7A H 0.2772 0.7078 0.1908 0.056 Uiso 1 1 calc R
H7B H 0.2696 0.7035 0.2740 0.056 Uiso 1 1 calc R
H7C H 0.2271 0.8399 0.2036 0.056 Uiso 1 1 calc R
C8 C 0.11428(7) 0.76362(16) 0.23516(8) 0.0215(3) Uani 1 1 d .
C9 C 0.14494(7) 0.74088(16) 0.32187(8) 0.0216(3) Uani 1 1 d .
C10 C 0.14296(7) 0.86870(17) 0.37223(8) 0.0234(3) Uani 1 1 d .
H10 H 0.1634 0.8532 0.4311 0.028 Uiso 1 1 calc R
C11 C 0.11126(7) 1.01746(17) 0.33629(8) 0.0236(3) Uani 1 1 d .
C12 C 0.07969(8) 1.03940(17) 0.24990(9) 0.0251(3) Uani 1 1 d .
H12 H 0.0574 1.1414 0.2257 0.030 Uiso 1 1 calc R
C13 C 0.08040(7) 0.91392(17) 0.19879(8) 0.0238(3) Uani 1 1 d .
C14 C 0.18116(8) 0.58110(18) 0.36368(9) 0.0298(3) Uani 1 1 d .
H14A H 0.2304 0.5774 0.3707 0.045 Uiso 1 1 calc R
H14B H 0.1527 0.4886 0.3286 0.045 Uiso 1 1 calc R
H14C H 0.1838 0.5737 0.4188 0.045 Uiso 1 1 calc R
C15 C 0.04532(9) 0.9413(2) 0.10554(9) 0.0342(4) Uani 1 1 d .
H15A H 0.0189 1.0460 0.0912 0.051 Uiso 1 1 calc R
H15B H 0.0112 0.8515 0.0762 0.051 Uiso 1 1 calc R
H15C H 0.0829 0.9441 0.0885 0.051 Uiso 1 1 calc R
C16 C 0.14722(9) 1.1400(2) 0.47002(9) 0.0364(4) Uani 1 1 d .
H16A H 0.1290 1.0475 0.4890 0.055 Uiso 1 1 calc R
H16B H 0.1413 1.2422 0.4945 0.055 Uiso 1 1 calc R
H16C H 0.1989 1.1229 0.4880 0.055 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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
C11 O2 C16 116.72(11)
O1 N1 C1 120.47(13)
O1 N1 C5 120.00(12)
C1 N1 C5 119.53(12)
N1 C1 C2 121.88(13)
N1 C1 H1 119.1
C2 C1 H1 119.1
C1 C2 C3 119.29(13)
C1 C2 C6 118.19(13)
C3 C2 C6 122.52(13)
C2 C3 C4 118.04(12)
C2 C3 C8 121.65(12)
C4 C3 C8 120.30(12)
C5 C4 C3 119.71(13)
C5 C4 C7 118.58(13)
C3 C4 C7 121.70(13)
N1 C5 C4 121.46(13)
N1 C5 H5 119.3
C4 C5 H5 119.3
C2 C6 H6A 109.5
C2 C6 H6B 109.5
H6A C6 H6B 109.5
C2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 119.78(12)
C9 C8 C3 120.48(12)
C13 C8 C3 119.73(12)
C8 C9 C10 119.84(12)
C8 C9 C14 121.72(12)
C10 C9 C14 118.44(12)
C11 C10 C9 120.01(12)
C11 C10 H10 120.0
C9 C10 H10 120.0
O2 C11 C10 124.36(12)
O2 C11 C12 115.42(12)
C10 C11 C12 120.22(12)
C13 C12 C11 120.70(12)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C8 119.42(12)
C12 C13 C15 119.35(12)
C8 C13 C15 121.23(12)
C9 C14 H14A 109.5
C9 C14 H14B 109.5
H14A C14 H14B 109.5
C9 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O2 C16 H16A 109.5
O2 C16 H16B 109.5
H16A C16 H16B 109.5
O2 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.3072(15)
O2 C11 1.3767(16)
O2 C16 1.4308(18)
N1 C1 1.3515(19)
N1 C5 1.3561(19)
C1 C2 1.389(2)
C1 H1 0.9500
C2 C3 1.4029(19)
C2 C6 1.504(2)
C3 C4 1.4079(19)
C3 C8 1.5006(18)
C4 C5 1.3834(19)
C4 C7 1.502(2)
C5 H5 0.9500
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.3990(18)
C8 C13 1.4084(19)
C9 C10 1.4009(18)
C9 C14 1.5122(19)
C10 C11 1.3836(19)
C10 H10 0.9500
C11 C12 1.3912(19)
C12 C13 1.3869(19)
C12 H12 0.9500
C13 C15 1.5044(19)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
