#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:40:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178437 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/58/4025812.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_4025812
loop_
_publ_author_name
'Paul M. Alvey'
'Joseph J. Reczek'
'Vincent Lynch'
'Brent L. Iverson'
_publ_section_title
;
 A Systematic Study of Thermochromic Aromatic Donor-Acceptor Materials
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7682
_journal_page_last               7690
_journal_paper_doi               10.1021/jo101498b
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C38 H54 N2 O4'
_chemical_formula_sum            'C38 H54 N2 O4'
_chemical_formula_weight         602.84
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.316(9)
_cell_angle_beta                 94.533(8)
_cell_angle_gamma                104.5980(14)
_cell_formula_units_Z            1
_cell_length_a                   4.6101(11)
_cell_length_b                   6.5900(15)
_cell_length_c                   27.733(7)
_cell_measurement_reflns_used    9443
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.0
_cell_volume                     810.1(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9427
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       laths
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0744P)²+0.6478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1626
_reflns_number_gt                2232
_reflns_number_total             2743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101498b_si_009.cif
_cod_data_source_block           n3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025812
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5704(3) 0.6039(2) 0.65097(5) 0.0250(4) Uani 1 1 d . . .
O2 O 0.9641(3) 0.1237(2) 0.57430(5) 0.0256(4) Uani 1 1 d . . .
N1 N 0.7704(4) 0.3657(3) 0.61283(6) 0.0188(4) Uani 1 1 d . . .
C1 C 0.6112(5) 0.5207(3) 0.61298(7) 0.0194(5) Uani 1 1 d . . .
C2 C 0.5009(4) 0.5766(3) 0.56552(7) 0.0170(5) Uani 1 1 d . . .
C3 C 0.5529(4) 0.4722(3) 0.52257(7) 0.0161(4) Uani 1 1 d . . .
C4 C 0.7088(4) 0.3143(3) 0.52414(7) 0.0171(5) Uani 1 1 d . . .
C5 C 0.8246(5) 0.2575(3) 0.57134(7) 0.0188(5) Uani 1 1 d . . .
C6 C 0.3474(5) 0.7303(3) 0.56312(8) 0.0195(5) Uani 1 1 d . . .
C7 C 0.7575(5) 0.2154(3) 0.48189(8) 0.0195(5) Uani 1 1 d . . .
C8 C 0.8846(5) 0.3113(3) 0.66017(7) 0.0211(5) Uani 1 1 d . . .
H8A H 0.9652 0.4420 0.6817 0.025 Uiso 1 1 calc R . .
H8B H 1.0529 0.2463 0.6555 0.025 Uiso 1 1 calc R . .
C9 C 0.6457(5) 0.1609(3) 0.68500(7) 0.0219(5) Uani 1 1 d . . .
H9A H 0.5219 0.2412 0.7015 0.026 Uiso 1 1 calc R . .
H9B H 0.5114 0.0582 0.6602 0.026 Uiso 1 1 calc R . .
C10 C 0.7869(5) 0.0437(3) 0.72193(7) 0.0210(5) Uani 1 1 d . . .
H10A H 0.9223 0.1471 0.7464 0.025 Uiso 1 1 calc R . .
H10B H 0.9109 -0.0358 0.7052 0.025 Uiso 1 1 calc R . .
C11 C 0.5559(5) -0.1080(3) 0.74769(7) 0.0210(5) Uani 1 1 d . . .
H11A H 0.4588 -0.0264 0.7694 0.025 Uiso 1 1 calc R . .
H11B H 0.3977 -0.1938 0.7233 0.025 Uiso 1 1 calc R . .
C12 C 0.6924(5) -0.2535(3) 0.77729(7) 0.0213(5) Uani 1 1 d . . .
H12A H 0.8475 -0.1673 0.8021 0.026 Uiso 1 1 calc R . .
H12B H 0.7943 -0.3319 0.7556 0.026 Uiso 1 1 calc R . .
C13 C 0.4649(5) -0.4104(3) 0.80249(7) 0.0221(5) Uani 1 1 d . . .
H13A H 0.3075 -0.4952 0.7778 0.026 Uiso 1 1 calc R . .
H13B H 0.3662 -0.3324 0.8248 0.026 Uiso 1 1 calc R . .
C14 C 0.6053(5) -0.5578(3) 0.83112(8) 0.0222(5) Uani 1 1 d . . .
H14A H 0.6977 -0.6392 0.8085 0.027 Uiso 1 1 calc R . .
H14B H 0.7682 -0.4725 0.8549 0.027 Uiso 1 1 calc R . .
C15 C 0.3825(5) -0.7105(3) 0.85804(7) 0.0227(5) Uani 1 1 d . . .
H15A H 0.2185 -0.7951 0.8344 0.027 Uiso 1 1 calc R . .
H15B H 0.2917 -0.6293 0.8809 0.027 Uiso 1 1 calc R . .
C16 C 0.5249(5) -0.8583(3) 0.88611(7) 0.0223(5) Uani 1 1 d . . .
H16A H 0.6137 -0.9407 0.8632 0.027 Uiso 1 1 calc R . .
H16B H 0.6904 -0.7737 0.9095 0.027 Uiso 1 1 calc R . .
C17 C 0.3029(5) -1.0095(3) 0.91348(8) 0.0238(5) Uani 1 1 d . . .
H17A H 0.2227 -0.9273 0.9377 0.029 Uiso 1 1 calc R . .
H17B H 0.1317 -1.0884 0.8903 0.029 Uiso 1 1 calc R . .
C18 C 0.4409(5) -1.1651(3) 0.93925(8) 0.0257(5) Uani 1 1 d . . .
H18A H 0.6086 -1.0865 0.9631 0.031 Uiso 1 1 calc R . .
H18B H 0.5258 -1.2449 0.9152 0.031 Uiso 1 1 calc R . .
C19 C 0.2148(6) -1.3190(4) 0.96540(8) 0.0311(6) Uani 1 1 d . . .
H19A H 0.1351 -1.2412 0.9901 0.047 Uiso 1 1 calc R . .
H19B H 0.3145 -1.4165 0.9810 0.047 Uiso 1 1 calc R . .
H19C H 0.0492 -1.3984 0.9420 0.047 Uiso 1 1 calc R . .
H6 H 0.315(5) 0.801(3) 0.5935(8) 0.017(5) Uiso 1 1 d . . .
H7 H 0.872(5) 0.111(4) 0.4824(7) 0.020(6) Uiso 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'
O O 0.0106 0.0060 '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'
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
C5 N1 C1 124.81(17) . . ?
C5 N1 C8 117.73(17) . . ?
C1 N1 C8 117.45(16) . . ?
O1 C1 N1 120.17(18) . . ?
O1 C1 C2 122.58(19) . . ?
N1 C1 C2 117.25(17) . . ?
C6 C2 C3 120.01(19) . . ?
C6 C2 C1 120.15(18) . . ?
C3 C2 C1 119.84(18) . . ?
C4 C3 C2 121.00(19) . . ?
C4 C3 C3 119.8(2) . 2_666 ?
C2 C3 C3 119.2(2) . 2_666 ?
C7 C4 C3 119.99(19) . . ?
C7 C4 C5 119.95(18) . . ?
C3 C4 C5 120.06(18) . . ?
O2 C5 N1 120.80(19) . . ?
O2 C5 C4 122.17(19) . . ?
N1 C5 C4 117.02(17) . . ?
C2 C6 C7 120.47(19) . 2_666 ?
C2 C6 H6 118.5(13) . . ?
C7 C6 H6 121.0(13) 2_666 . ?
C4 C7 C6 120.5(2) . 2_666 ?
C4 C7 H7 120.8(13) . . ?
C6 C7 H7 118.6(12) 2_666 . ?
N1 C8 C9 113.28(17) . . ?
N1 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 111.44(17) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 113.16(17) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 112.88(17) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 113.96(17) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 113.14(17) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 113.75(18) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 113.25(18) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 113.27(18) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 113.30(18) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 112.81(19) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C1 1.209(2) . ?
O2 C5 1.218(2) . ?
N1 C5 1.391(3) . ?
N1 C1 1.399(3) . ?
N1 C8 1.473(2) . ?
C1 C2 1.474(3) . ?
C2 C6 1.376(3) . ?
C2 C3 1.408(3) . ?
C3 C4 1.407(3) . ?
C3 C3 1.409(4) 2_666 ?
C4 C7 1.370(3) . ?
C4 C5 1.478(3) . ?
C6 C7 1.402(3) 2_666 ?
C6 H6 0.98(2) . ?
C7 C6 1.402(3) 2_666 ?
C7 H7 0.97(2) . ?
C8 C9 1.523(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.520(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.520(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.517(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.520(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.522(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.520(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.522(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.520(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.520(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.521(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 O1 178.66(18) . . . . ?
C8 N1 C1 O1 -0.4(3) . . . . ?
C5 N1 C1 C2 -1.8(3) . . . . ?
C8 N1 C1 C2 179.19(17) . . . . ?
O1 C1 C2 C6 0.7(3) . . . . ?
N1 C1 C2 C6 -178.87(18) . . . . ?
O1 C1 C2 C3 -179.30(19) . . . . ?
N1 C1 C2 C3 1.2(3) . . . . ?
C6 C2 C3 C4 -179.89(18) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C6 C2 C3 C3 0.3(3) . . . 2_666 ?
C1 C2 C3 C3 -179.8(2) . . . 2_666 ?
C2 C3 C4 C7 -179.80(18) . . . . ?
C3 C3 C4 C7 0.1(3) 2_666 . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C3 C4 C5 179.1(2) 2_666 . . . ?
C1 N1 C5 O2 -179.62(19) . . . . ?
C8 N1 C5 O2 -0.6(3) . . . . ?
C1 N1 C5 C4 1.1(3) . . . . ?
C8 N1 C5 C4 -179.90(17) . . . . ?
C7 C4 C5 O2 0.0(3) . . . . ?
C3 C4 C5 O2 -179.02(19) . . . . ?
C7 C4 C5 N1 179.26(18) . . . . ?
C3 C4 C5 N1 0.3(3) . . . . ?
C3 C2 C6 C7 -0.2(3) . . . 2_666 ?
C1 C2 C6 C7 179.86(18) . . . 2_666 ?
C3 C4 C7 C6 -0.1(3) . . . 2_666 ?
C5 C4 C7 C6 -179.14(18) . . . 2_666 ?
C5 N1 C8 C9 -98.6(2) . . . . ?
C1 N1 C8 C9 80.5(2) . . . . ?
N1 C8 C9 C10 157.81(17) . . . . ?
C8 C9 C10 C11 179.84(17) . . . . ?
C9 C10 C11 C12 169.18(17) . . . . ?
C10 C11 C12 C13 -178.63(17) . . . . ?
C11 C12 C13 C14 178.82(17) . . . . ?
C12 C13 C14 C15 177.91(17) . . . . ?
C13 C14 C15 C16 179.43(18) . . . . ?
C14 C15 C16 C17 179.37(17) . . . . ?
C15 C16 C17 C18 176.83(18) . . . . ?
C16 C17 C18 C19 -178.50(18) . . . . ?
