#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:33:26 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179535 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/04/4500415.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_4500415
loop_
_publ_author_name
'Collas, Alain'
'Bagrowska, Izabela'
'Aleksandrzak, Krzysztof'
'Zeller, Matthias'
'Blockhuys, Frank'
_publ_section_title
;
 Competition between Methoxy-Based and Pyrazine-Based Synthons in
 Methoxy-Substituted Distyrylpyrazines
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1299
_journal_paper_doi               10.1021/cg101523f
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C24 H24 N2 O4'
_chemical_formula_sum            'C24 H24 N2 O4'
_chemical_formula_weight         404.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 90.938(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.118(3)
_cell_length_b                   9.424(2)
_cell_length_c                   7.8733(18)
_cell_measurement_reflns_used    845
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.0944
_cell_measurement_theta_min      2.5978
_cell_volume                     1047.4(4)
_computing_cell_refinement       'Apex2 v2008.2-4'
_computing_data_collection       'Apex2 v2008.2-4 (Bruker, 2008)'
_computing_data_reduction        'Apex2 v2008.2-4'
_computing_molecular_graphics
'ORTEP (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'WINGX (Farrugia, 1999) and PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5406
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2008.2-4 (Bruker, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0612
_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)+(0.0660P)²+0.0637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1740
_reflns_number_gt                1352
_reflns_number_total             2566
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg101523f_si_003.cif
_cod_data_source_block           pol234mdsp_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4500415
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.68513(15) 1.0330(2) 0.4425(3) 0.0496(5) Uani 1 1 d .
C2 C 0.76826(17) 0.9507(2) 0.4461(3) 0.0571(6) Uani 1 1 d .
H2 H 0.7815 0.8934 0.5397 0.069 Uiso 1 1 calc R
C3 C 0.82994(17) 0.9535(3) 0.3138(3) 0.0571(6) Uani 1 1 d .
C4 C 0.81011(16) 1.0379(2) 0.1703(3) 0.0520(6) Uani 1 1 d .
C5 C 0.72873(16) 1.1168(2) 0.1648(3) 0.0538(6) Uani 1 1 d .
H5 H 0.7145 1.1715 0.0695 0.065 Uiso 1 1 calc R
C6 C 0.66751(16) 1.1157(2) 0.3002(3) 0.0534(6) Uani 1 1 d .
H6 H 0.6133 1.1718 0.2955 0.064 Uiso 1 1 calc R
C7 C 0.62051(16) 1.0397(3) 0.5843(3) 0.0535(6) Uani 1 1 d .
H7 H 0.5732 1.1082 0.5762 0.064 Uiso 1 1 calc R
C8 C 0.62032(16) 0.9605(2) 0.7240(3) 0.0548(6) Uani 1 1 d .
H8 H 0.6634 0.8860 0.7315 0.066 Uiso 1 1 calc R
C9 C 0.55693(15) 0.9827(2) 0.8663(3) 0.0519(6) Uani 1 1 d .
C10 C 0.44999(16) 1.1167(3) 1.0048(3) 0.0587(6) Uani 1 1 d .
H10 H 0.4133 1.1983 1.0120 0.070 Uiso 1 1 calc R
C31 C 0.9371(3) 0.7946(5) 0.4481(4) 0.1376(18) Uani 1 1 d .
H31A H 0.9442 0.8529 0.5475 0.206 Uiso 1 1 calc R
H31B H 0.9955 0.7460 0.4273 0.206 Uiso 1 1 calc R
H31C H 0.8877 0.7264 0.4655 0.206 Uiso 1 1 calc R
C41 C 0.8590(2) 1.1119(3) -0.1040(3) 0.0799(9) Uani 1 1 d .
H41A H 0.8016 1.0777 -0.1567 0.120 Uiso 1 1 calc R
H41B H 0.9107 1.0991 -0.1802 0.120 Uiso 1 1 calc R
H41C H 0.8523 1.2109 -0.0780 0.120 Uiso 1 1 calc R
N1 N 0.50565(13) 1.1027(2) 0.8718(2) 0.0580(5) Uani 1 1 d .
O3 O 0.91343(14) 0.8804(2) 0.3074(2) 0.0887(7) Uani 1 1 d .
O4 O 0.87733(12) 1.03482(19) 0.04845(19) 0.0695(5) Uani 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 117.8(2) . .
C6 C1 C7 119.4(2) . .
C2 C1 C7 122.8(2) . .
C3 C2 C1 121.0(2) . .
C3 C2 H2 119.5 . .
C1 C2 H2 119.5 . .
O3 C3 C2 125.3(2) . .
O3 C3 C4 114.6(2) . .
C2 C3 C4 120.1(2) . .
O4 C4 C5 125.7(2) . .
O4 C4 C3 115.0(2) . .
C5 C4 C3 119.2(2) . .
C4 C5 C6 120.4(2) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C5 C6 C1 121.4(2) . .
C5 C6 H6 119.3 . .
C1 C6 H6 119.3 . .
C8 C7 C1 128.4(2) . .
C8 C7 H7 115.8 . .
C1 C7 H7 115.8 . .
C7 C8 C9 124.3(2) . .
C7 C8 H8 117.8 . .
C9 C8 H8 117.8 . .
N1 C9 C10 120.0(2) . 3_677
N1 C9 C8 118.8(2) . .
C10 C9 C8 121.1(2) 3_677 .
N1 C10 C9 124.1(2) . 3_677
N1 C10 H10 117.9 . .
C9 C10 H10 117.9 3_677 .
O3 C31 H31A 109.5 . .
O3 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
O3 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
O4 C41 H41A 109.5 . .
O4 C41 H41B 109.5 . .
H41A C41 H41B 109.5 . .
O4 C41 H41C 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
C10 N1 C9 115.80(19) . .
C3 O3 C31 117.0(2) . .
C4 O4 C41 117.69(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.384(3) .
C1 C2 1.407(3) .
C1 C7 1.455(3) .
C2 C3 1.369(3) .
C2 H2 0.9300 .
C3 O3 1.367(3) .
C3 C4 1.406(3) .
C4 O4 1.361(2) .
C4 C5 1.369(3) .
C5 C6 1.383(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.329(3) .
C7 H7 0.9300 .
C8 C9 1.461(3) .
C8 H8 0.9300 .
C9 N1 1.344(3) .
C9 C10 1.385(3) 3_677
C10 N1 1.326(3) .
C10 C9 1.385(3) 3_677
C10 H10 0.9300 .
C31 O3 1.407(3) .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
C41 O4 1.423(3) .
C41 H41A 0.9600 .
C41 H41B 0.9600 .
C41 H41C 0.9600 .
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_4
C6 C1 C2 C3 0.6(3) . .
C7 C1 C2 C3 -176.3(2) . .
C1 C2 C3 O3 178.2(2) . .
C1 C2 C3 C4 -1.0(4) . .
O3 C3 C4 O4 -0.6(3) . .
C2 C3 C4 O4 178.6(2) . .
O3 C3 C4 C5 -179.2(2) . .
C2 C3 C4 C5 0.1(4) . .
O4 C4 C5 C6 -177.2(2) . .
C3 C4 C5 C6 1.2(3) . .
C4 C5 C6 C1 -1.6(3) . .
C2 C1 C6 C5 0.7(3) . .
C7 C1 C6 C5 177.6(2) . .
C6 C1 C7 C8 173.5(2) . .
C2 C1 C7 C8 -9.7(4) . .
C1 C7 C8 C9 174.8(2) . .
C7 C8 C9 N1 -11.2(3) . .
C7 C8 C9 C10 169.6(2) . 3_677
C9 C10 N1 C9 0.4(4) 3_677 .
C10 C9 N1 C10 -0.4(3) 3_677 .
C8 C9 N1 C10 -179.59(19) . .
C2 C3 O3 C31 0.5(4) . .
C4 C3 O3 C31 179.8(3) . .
C5 C4 O4 C41 -4.9(3) . .
C3 C4 O4 C41 176.7(2) . .
