#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/39/7103928.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_7103928
loop_
_publ_author_name
'Andrew Bond'
_publ_section_title
;
In situ co-crystallisation as a tool for
low-temperature crystal engineering
;
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/b208904a
_journal_year                    2003
_chemical_formula_moiety         'C4 H4 N2, 2(C9 H18 O2)'
_chemical_formula_sum            'C22 H40 N2 O4'
_chemical_formula_weight         396.56
_chemical_name_common            'pyrazine / nonanoic acid'
_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
_cell_angle_alpha                89.776(1)
_cell_angle_beta                 82.992(1)
_cell_angle_gamma                76.091(1)
_cell_formula_units_Z            1
_cell_length_a                   5.4731(2)
_cell_length_b                   6.8775(2)
_cell_length_c                   16.3824(6)
_cell_measurement_reflns_used    5100
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     593.89(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor, 1997)
;
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6194
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         3.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             218
_exptl_crystal_size_length       0.35
_exptl_crystal_size_rad          0.10
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0533
_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)+(0.0638P)²+0.1622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                2221
_reflns_number_total             2652
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b208904a.txt
_cod_data_source_block           ab0212
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7103928
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 -0.4479(2) 0.68345(15) 0.13075(7) 0.0466(3) Uani 1 1 d . . .
H1 H -0.578(5) 0.748(3) 0.1001(14) 0.079(7) Uiso 1 1 d . . .
O2 O -0.6328(2) 0.43227(15) 0.11629(7) 0.0468(3) Uani 1 1 d . . .
C1 C -0.4719(2) 0.49741(18) 0.14293(8) 0.0303(3) Uani 1 1 d . . .
C2 C -0.2778(2) 0.38372(18) 0.19442(8) 0.0319(3) Uani 1 1 d . . .
H2A H -0.3008 0.4555 0.2481 0.038 Uiso 1 1 calc R . .
H2B H -0.1068 0.3847 0.1668 0.038 Uiso 1 1 calc R . .
C3 C -0.2878(2) 0.16738(18) 0.21008(8) 0.0318(3) Uani 1 1 d . . .
H3A H -0.2634 0.0931 0.1569 0.038 Uiso 1 1 calc R . .
H3B H -0.4567 0.1640 0.2388 0.038 Uiso 1 1 calc R . .
C4 C -0.0827(3) 0.06629(19) 0.26222(9) 0.0349(3) Uani 1 1 d . . .
H4A H -0.1081 0.1428 0.3149 0.042 Uiso 1 1 calc R . .
H4B H 0.0848 0.0725 0.2332 0.042 Uiso 1 1 calc R . .
C5 C -0.0788(3) -0.15198(19) 0.28085(9) 0.0345(3) Uani 1 1 d . . .
H5A H -0.2484 -0.1600 0.3074 0.041 Uiso 1 1 calc R . .
H5B H -0.0427 -0.2311 0.2285 0.041 Uiso 1 1 calc R . .
C6 C 0.1191(3) -0.24309(19) 0.33689(9) 0.0351(3) Uani 1 1 d . . .
H6A H 0.0835 -0.1620 0.3887 0.042 Uiso 1 1 calc R . .
H6B H 0.2882 -0.2349 0.3099 0.042 Uiso 1 1 calc R . .
C7 C 0.1280(3) -0.46059(19) 0.35781(8) 0.0345(3) Uani 1 1 d . . .
H7A H -0.0431 -0.4706 0.3821 0.041 Uiso 1 1 calc R . .
H7B H 0.1739 -0.5436 0.3065 0.041 Uiso 1 1 calc R . .
C8 C 0.3170(3) -0.5441(2) 0.41762(10) 0.0423(4) Uani 1 1 d . . .
H8A H 0.4879 -0.5340 0.3931 0.051 Uiso 1 1 calc R . .
H8B H 0.2714 -0.4601 0.4687 0.051 Uiso 1 1 calc R . .
C9 C 0.3282(4) -0.7608(2) 0.43965(11) 0.0535(4) Uani 1 1 d . . .
H9A H 0.1595 -0.7727 0.4635 0.080 Uiso 1 1 calc R . .
H9B H 0.4486 -0.8027 0.4797 0.080 Uiso 1 1 calc R . .
H9C H 0.3837 -0.8465 0.3899 0.080 Uiso 1 1 calc R . .
N1A N -0.8074(2) 0.89882(16) 0.04332(7) 0.0331(3) Uani 1 1 d . . .
C1A C -0.9706(3) 0.80678(19) 0.01611(8) 0.0334(3) Uani 1 1 d . . .
H1AA H -0.9547 0.6687 0.0267 0.040 Uiso 1 1 calc R . .
C2A C -0.8366(2) 1.09317(19) 0.02735(8) 0.0337(3) Uani 1 1 d . . .
H2AA H -0.7237 1.1638 0.0460 0.040 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 107.6(14) . . ?
O2 C1 O1 123.09(12) . . ?
O2 C1 C2 125.36(11) . . ?
O1 C1 C2 111.54(11) . . ?
C1 C2 C3 115.15(10) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C4 110.77(10) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C5 114.29(11) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 112.41(11) . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 114.23(11) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 113.07(12) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 113.95(13) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1A N1A C2A 117.26(11) . . ?
N1A C1A C2A 121.83(12) . 2_375 ?
N1A C1A H1AA 119.1 . . ?
C2A C1A H1AA 119.1 2_375 . ?
N1A C2A C1A 120.91(12) . 2_375 ?
N1A C2A H2AA 119.5 . . ?
C1A C2A H2AA 119.5 2_375 . ?
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 1.3291(15) . ?
O1 H1 0.95(3) . ?
O2 C1 1.2045(16) . ?
C1 C2 1.5054(17) . ?
C2 C3 1.5216(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5256(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5263(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5233(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5240(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5223(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N1A C1A 1.3298(18) . ?
N1A C2A 1.3362(16) . ?
C1A C2A 1.3873(19) 2_375 ?
C1A H1AA 0.9500 . ?
C2A C1A 1.3873(19) 2_375 ?
C2A H2AA 0.9500 . ?
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
O2 C1 C2 C3 2.1(2) . . . . ?
O1 C1 C2 C3 -178.83(11) . . . . ?
C1 C2 C3 C4 179.65(11) . . . . ?
C2 C3 C4 C5 -179.91(11) . . . . ?
C3 C4 C5 C6 -176.83(11) . . . . ?
C4 C5 C6 C7 179.45(11) . . . . ?
C5 C6 C7 C8 -176.81(12) . . . . ?
C6 C7 C8 C9 179.74(12) . . . . ?
C2A N1A C1A C2A 0.2(2) . . . 2_375 ?
C1A N1A C2A C1A -0.2(2) . . . 2_375 ?
