#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/41/2234118.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234118
loop_
_publ_author_name
'Wrobel, Norma'
'Schollmeyer, Dieter'
'Detert, Heiner'
_publ_section_title
;
 1,4-Dihexyloxy-2,5-bis(2-nitrophenyl)benzene
;
_journal_coeditor_code           BT5839
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1022
_journal_paper_doi               10.1107/S1600536812009944
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C30 H36 N2 O6'
_chemical_formula_moiety         'C30 H36 N2 O6'
_chemical_formula_sum            'C30 H36 N2 O6'
_chemical_formula_weight         520.61
_chemical_name_systematic
;
1,4-Dihexyloxy-2,5-bis(2-nitrophenyl)benzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.368(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9314(4)
_cell_length_b                   19.2029(17)
_cell_length_c                   9.1247(5)
_cell_measurement_reflns_used    7928
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.09
_cell_measurement_theta_min      3.23
_cell_volume                     1381.17(16)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2011)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2011)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8154
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0437
_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)+(0.0562P)²+0.4038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1119
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                2610
_reflns_number_total             3331
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5839.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2234118
_cod_database_fobs_code          2234118
loop_
_symmetry_equiv_pos_as_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.46215(15) 0.52525(7) 0.35512(14) 0.0240(3) Uani d . 1 1
C C2 0.35820(15) 0.54228(7) 0.46442(14) 0.0252(3) Uani d . 1 1
C C3 0.60362(16) 0.48321(8) 0.39358(14) 0.0264(3) Uani d . 1 1
H H3 0.6756 0.4717 0.3206 0.032 Uiso calc R 1 1
C C4 0.43305(15) 0.55452(7) 0.20336(14) 0.0232(3) Uani d . 1 1
C C5 0.57076(16) 0.58310(8) 0.14150(15) 0.0299(3) Uani d . 1 1
H H5 0.6801 0.5811 0.1956 0.036 Uiso calc R 1 1
C C6 0.55321(18) 0.61424(8) 0.00394(16) 0.0338(3) Uani d . 1 1
H H6 0.6502 0.6318 -0.0362 0.041 Uiso calc R 1 1
C C7 0.39481(18) 0.61991(8) -0.07522(16) 0.0309(3) Uani d . 1 1
H H7 0.3820 0.6432 -0.1676 0.037 Uiso calc R 1 1
C C8 0.25493(17) 0.59149(7) -0.01925(15) 0.0273(3) Uani d . 1 1
H H8 0.1456 0.5945 -0.0732 0.033 Uiso calc R 1 1
C C9 0.27660(15) 0.55862(7) 0.11640(14) 0.0225(3) Uani d . 1 1
N N10 0.12608(13) 0.52343(6) 0.16019(12) 0.0271(3) Uani d . 1 1
O O11 -0.01207(12) 0.55180(6) 0.13048(12) 0.0381(3) Uani d . 1 1
O O12 0.14470(14) 0.46637(6) 0.21901(12) 0.0380(3) Uani d . 1 1
O O13 0.22425(12) 0.58564(6) 0.42244(10) 0.0314(2) Uani d . 1 1
C C14 0.11269(18) 0.60345(9) 0.52871(16) 0.0330(3) Uani d . 1 1
H H14A 0.1748 0.6300 0.6106 0.040 Uiso calc R 1 1
H H14B 0.0665 0.5607 0.5699 0.040 Uiso calc R 1 1
C C15 -0.02962(17) 0.64694(9) 0.45359(16) 0.0330(3) Uani d . 1 1
H H15A 0.0189 0.6874 0.4055 0.040 Uiso calc R 1 1
H H15B -0.0946 0.6188 0.3758 0.040 Uiso calc R 1 1
C C16 -0.1481(2) 0.67270(12) 0.5597(2) 0.0560(6) Uani d . 1 1
H H16A -0.1793 0.6328 0.6201 0.067 Uiso calc R 1 1
H H16B -0.0862 0.7067 0.6274 0.067 Uiso calc R 1 1
C C17 -0.30865(18) 0.70652(8) 0.49024(18) 0.0344(3) Uani d . 1 1
H H17A -0.2781 0.7465 0.4299 0.041 Uiso calc R 1 1
H H17B -0.3715 0.6726 0.4231 0.041 Uiso calc R 1 1
C C18 -0.4239(3) 0.73189(14) 0.5993(3) 0.0670(7) Uani d . 1 1
H H18A -0.4492 0.6924 0.6631 0.080 Uiso calc R 1 1
H H18B -0.3626 0.7675 0.6632 0.080 Uiso calc R 1 1
C C19 -0.5889(2) 0.76264(11) 0.5319(3) 0.0602(6) Uani d . 1 1
H H19A -0.5662 0.8048 0.4767 0.090 Uiso calc R 1 1
H H19B -0.6592 0.7745 0.6101 0.090 Uiso calc R 1 1
H H19C -0.6488 0.7287 0.4650 0.090 Uiso calc R 1 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C3 C1 C2 . . 118.44(12)
C3 C1 C4 . . 119.33(11)
C2 C1 C4 . . 122.08(11)
O13 C2 C3 . 3_666 123.90(11)
O13 C2 C1 . . 116.22(11)
C3 C2 C1 3_666 . 119.85(12)
C2 C3 C1 3_666 . 121.70(11)
C2 C3 H3 3_666 . 119.2
C1 C3 H3 . . 119.2
C5 C4 C9 . . 115.65(12)
C5 C4 C1 . . 118.49(11)
C9 C4 C1 . . 125.82(11)
C6 C5 C4 . . 122.16(12)
C6 C5 H5 . . 118.9
C4 C5 H5 . . 118.9
C7 C6 C5 . . 120.15(12)
C7 C6 H6 . . 119.9
C5 C6 H6 . . 119.9
C6 C7 C8 . . 119.71(13)
C6 C7 H7 . . 120.1
C8 C7 H7 . . 120.1
C9 C8 C7 . . 119.02(12)
C9 C8 H8 . . 120.5
C7 C8 H8 . . 120.5
C8 C9 C4 . . 123.21(12)
C8 C9 N10 . . 115.49(11)
C4 C9 N10 . . 121.17(11)
O12 N10 O11 . . 123.84(12)
O12 N10 C9 . . 118.09(11)
O11 N10 C9 . . 118.01(12)
C2 O13 C14 . . 118.44(10)
O13 C14 C15 . . 108.30(11)
O13 C14 H14A . . 110.0
C15 C14 H14A . . 110.0
O13 C14 H14B . . 110.0
C15 C14 H14B . . 110.0
H14A C14 H14B . . 108.4
C16 C15 C14 . . 112.27(12)
C16 C15 H15A . . 109.2
C14 C15 H15A . . 109.2
C16 C15 H15B . . 109.2
C14 C15 H15B . . 109.2
H15A C15 H15B . . 107.9
C17 C16 C15 . . 115.45(14)
C17 C16 H16A . . 108.4
C15 C16 H16A . . 108.4
C17 C16 H16B . . 108.4
C15 C16 H16B . . 108.4
H16A C16 H16B . . 107.5
C18 C17 C16 . . 114.11(15)
C18 C17 H17A . . 108.7
C16 C17 H17A . . 108.7
C18 C17 H17B . . 108.7
C16 C17 H17B . . 108.7
H17A C17 H17B . . 107.6
C19 C18 C17 . . 114.93(19)
C19 C18 H18A . . 108.5
C17 C18 H18A . . 108.5
C19 C18 H18B . . 108.5
C17 C18 H18B . . 108.5
H18A C18 H18B . . 107.5
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_site_symmetry_2
_geom_bond_distance
C1 C3 . 1.3952(18)
C1 C2 . 1.4014(17)
C1 C4 . 1.4886(18)
C2 O13 . 1.3705(15)
C2 C3 3_666 1.3867(19)
C3 C2 3_666 1.3867(19)
C3 H3 . 0.9500
C4 C5 . 1.3963(18)
C4 C9 . 1.3990(17)
C5 C6 . 1.383(2)
C5 H5 . 0.9500
C6 C7 . 1.382(2)
C6 H6 . 0.9500
C7 C8 . 1.3838(19)
C7 H7 . 0.9500
C8 C9 . 1.3831(18)
C8 H8 . 0.9500
C9 N10 . 1.4655(16)
N10 O12 . 1.2218(16)
N10 O11 . 1.2268(15)
O13 C14 . 1.4250(15)
C14 C15 . 1.5065(19)
C14 H14A . 0.9900
C14 H14B . 0.9900
C15 C16 . 1.506(2)
C15 H15A . 0.9900
C15 H15B . 0.9900
C16 C17 . 1.505(2)
C16 H16A . 0.9900
C16 H16B . 0.9900
C17 C18 . 1.505(2)
C17 H17A . 0.9900
C17 H17B . 0.9900
C18 C19 . 1.503(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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3 C1 C2 O13 . . 177.82(12)
C4 C1 C2 O13 . . 2.17(19)
C3 C1 C2 C3 . 3_666 -0.7(2)
C4 C1 C2 C3 . 3_666 -176.30(13)
C2 C1 C3 C2 . 3_666 0.7(2)
C4 C1 C3 C2 . 3_666 176.44(13)
C3 C1 C4 C5 . . -44.37(18)
C2 C1 C4 C5 . . 131.25(14)
C3 C1 C4 C9 . . 138.15(14)
C2 C1 C4 C9 . . -46.2(2)
C9 C4 C5 C6 . . 0.8(2)
C1 C4 C5 C6 . . -176.95(13)
C4 C5 C6 C7 . . 2.1(2)
C5 C6 C7 C8 . . -2.9(2)
C6 C7 C8 C9 . . 0.8(2)
C7 C8 C9 C4 . . 2.2(2)
C7 C8 C9 N10 . . -173.60(12)
C5 C4 C9 C8 . . -3.0(2)
C1 C4 C9 C8 . . 174.57(13)
C5 C4 C9 N10 . . 172.61(12)
C1 C4 C9 N10 . . -9.8(2)
C8 C9 N10 O12 . . 138.53(13)
C4 C9 N10 O12 . . -37.39(18)
C8 C9 N10 O11 . . -38.71(17)
C4 C9 N10 O11 . . 145.37(13)
C3 C2 O13 C14 3_666 . -2.8(2)
C1 C2 O13 C14 . . 178.78(13)
C2 O13 C14 C15 . . -176.02(12)
O13 C14 C15 C16 . . -175.95(16)
C14 C15 C16 C17 . . -170.43(16)
C15 C16 C17 C18 . . -179.81(19)
C16 C17 C18 C19 . . -177.1(2)
