#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:20:24 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179573 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/38/4503836.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_4503836
loop_
_publ_author_name
'Sarma, Bipul'
'Reddy, L. Sreenivas'
'Nangia, Ashwini'
_publ_section_title
;
 The Role of π-Stacking in the Composition of Phloroglucinol and
 Phenazine Cocrystals
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4546
_journal_paper_doi               10.1021/cg800585d
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         '(C12 H8 N2), 0.5(C6 H6 O3)'
_chemical_formula_sum            'C15 H11 N2 O1.5'
_chemical_formula_weight         243.2644
_chemical_name_common
; 
0.5:1 complex of pluoroglucinol and phenazine 
;
_chemical_name_systematic
; 
0.5:1 complex of pluoroglucinol and phenazine 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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                 102.423(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.159(3)
_cell_length_b                   11.943(3)
_cell_length_c                   14.249(3)
_cell_measurement_reflns_used    609
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.53
_cell_measurement_theta_min      2.25
_cell_volume                     2353.1(9)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5308
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0636
_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)+(0.0632P)²+0.3420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                1287
_reflns_number_total             2326
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800585d_si_006.cif
_cod_data_source_block           an289_m_PHG:Phen=1:2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2353.2(10)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               4503836
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 0.0000 1.1550(2) 0.2500 0.0757(11) Uani 1 2 d S
H1 H -0.0049 1.1785 0.1936 0.114 Uiso 0.50 1 calc PR
O2 O 0.01640(12) 0.81397(17) 0.42181(13) 0.0383(5) Uani 1 1 d .
H2 H 0.015(3) 0.725(4) 0.414(3) 0.112(14) Uiso 1 1 d .
C1 C 0.0000 1.0406(3) 0.2500 0.0363(10) Uani 1 2 d S
C2 C 0.00752(18) 0.9842(2) 0.3364(2) 0.0332(7) Uani 1 1 d .
H2A H 0.0123 1.0244 0.3948 0.040 Uiso 1 1 calc R
C3 C 0.00798(16) 0.8683(2) 0.33584(19) 0.0267(6) Uani 1 1 d .
C4 C 0.0000 0.8090(3) 0.2500 0.0301(9) Uani 1 2 d S
H4 H 0.0000 0.7295 0.2500 0.036 Uiso 1 2 calc SR
N1 N 0.02796(16) 0.5856(2) 0.39275(16) 0.0404(6) Uani 1 1 d .
N2 N 0.03596(18) 0.3477(2) 0.38103(18) 0.0563(8) Uani 1 1 d .
C5 C 0.11373(19) 0.5315(2) 0.40804(19) 0.0379(7) Uani 1 1 d .
C6 C 0.20096(19) 0.5944(3) 0.42987(19) 0.0444(8) Uani 1 1 d .
H6 H 0.1981 0.6737 0.4336 0.053 Uiso 1 1 calc R
C7 C 0.2885(2) 0.5426(3) 0.4455(2) 0.0475(8) Uani 1 1 d .
H7 H 0.3461 0.5858 0.4604 0.057 Uiso 1 1 calc R
C8 C 0.2942(2) 0.4239(3) 0.4395(2) 0.0494(9) Uani 1 1 d .
H8 H 0.3557 0.3886 0.4503 0.059 Uiso 1 1 calc R
C9 C 0.2129(2) 0.3610(3) 0.4185(2) 0.0471(8) Uani 1 1 d .
H9 H 0.2177 0.2819 0.4143 0.056 Uiso 1 1 calc R
C10 C 0.1201(2) 0.4124(2) 0.40260(19) 0.0378(7) Uani 1 1 d .
C11 C -0.05179(19) 0.4042(3) 0.36438(19) 0.0391(7) Uani 1 1 d .
C12 C -0.1411(2) 0.3451(3) 0.3402(2) 0.0519(9) Uani 1 1 d .
H12 H -0.1408 0.2656 0.3376 0.062 Uiso 1 1 calc R
C13 C -0.2263(2) 0.4004(3) 0.3208(2) 0.0600(10) Uani 1 1 d .
H13 H -0.2851 0.3595 0.3045 0.072 Uiso 1 1 calc R
C14 C -0.2287(2) 0.5183(3) 0.3246(2) 0.0585(10) Uani 1 1 d .
H14 H -0.2891 0.5560 0.3103 0.070 Uiso 1 1 calc R
C15 C -0.1452(2) 0.5790(3) 0.3487(2) 0.0513(9) Uani 1 1 d .
H15 H -0.1478 0.6584 0.3516 0.062 Uiso 1 1 calc R
C16 C -0.05398(19) 0.5230(3) 0.36953(19) 0.0406(8) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C1 O1 H1 109.5 . .
C3 O2 H2 113(2) . .
O1 C1 C2 119.02(18) . .
O1 C1 C2 119.02(18) . 2
C2 C1 C2 122.0(4) . 2
C3 C2 C1 118.6(3) . .
C3 C2 H2A 120.7 . .
C1 C2 H2A 120.7 . .
O2 C3 C2 117.9(2) . .
O2 C3 C4 121.2(2) . .
C2 C3 C4 120.8(3) . .
C3 C4 C3 119.1(3) . 2
C3 C4 H4 120.5 . .
C3 C4 H4 120.5 2 .
C5 N1 C16 117.8(2) . .
C11 N2 C10 117.3(3) . .
N1 C5 C6 119.4(3) . .
N1 C5 C10 122.2(3) . .
C6 C5 C10 118.5(3) . .
C7 C6 C5 120.9(3) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C6 C7 C8 120.3(3) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C9 C8 C7 120.6(3) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C8 C9 C10 120.5(3) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
N2 C10 C9 120.7(3) . .
N2 C10 C5 120.1(2) . .
C9 C10 C5 119.2(3) . .
N2 C11 C16 120.3(3) . .
N2 C11 C12 121.1(3) . .
C16 C11 C12 118.6(3) . .
C13 C12 C11 120.9(3) . .
C13 C12 H12 119.5 . .
C11 C12 H12 119.5 . .
C12 C13 C14 120.6(3) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
C15 C14 C13 120.9(3) . .
C15 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C14 C15 C16 119.9(3) . .
C14 C15 H15 120.0 . .
C16 C15 H15 120.0 . .
N1 C16 C11 122.3(3) . .
N1 C16 C15 118.6(3) . .
C11 C16 C15 119.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.367(4) .
O1 H1 0.8400 .
O2 C3 1.369(3) .
O2 H2 1.06(4) .
C1 C2 1.387(3) .
C1 C2 1.387(3) 2
C2 C3 1.385(3) .
C2 H2A 0.9500 .
C3 C4 1.397(3) .
C4 C3 1.397(3) 2
C4 H4 0.9500 .
N1 C5 1.351(3) .
N1 C16 1.360(3) .
N2 C11 1.389(3) .
N2 C10 1.397(3) .
C5 C6 1.422(4) .
C5 C10 1.428(4) .
C6 C7 1.360(4) .
C6 H6 0.9500 .
C7 C8 1.423(4) .
C7 H7 0.9500 .
C8 C9 1.355(4) .
C8 H8 0.9500 .
C9 C10 1.423(4) .
C9 H9 0.9500 .
C11 C16 1.422(4) .
C11 C12 1.424(4) .
C12 C13 1.351(4) .
C12 H12 0.9500 .
C13 C14 1.410(5) .
C13 H13 0.9500 .
C14 C15 1.365(4) .
C14 H14 0.9500 .
C15 C16 1.428(4) .
C15 H15 0.9500 .
