#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:51:31 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179600 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/64/4506458.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_4506458
loop_
_publ_author_name
'Thakuria, Ranjit'
'Cherukuvada, Suryanarayan'
'Nangia, Ashwini'
_publ_section_title
;
 Crystal Structures of Pyrogallol, Its Hydrate, and Stable
 MultipleZ′ Cocrystals with N-Heterocycles Containing Metastable
 Conformers of Pyrogallol
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3944
_journal_paper_doi               10.1021/cg3003367
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C6 H6 O3, 0.5(C6 H6 N2 O)'
_chemical_formula_sum            'C18 H18 N2 O7'
_chemical_formula_weight         374.34
_chemical_name_systematic
; 
 2:1  complex of pyrogallol and nicotinamide  
;
_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                 108.082(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2860(13)
_cell_length_b                   19.551(2)
_cell_length_c                   7.8342(9)
_cell_measurement_reflns_used    5562
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.93
_cell_volume                     1643.3(3)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16948
_diffrn_reflns_theta_full        26.12
_diffrn_reflns_theta_max         26.12
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0445
_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)+(0.0535P)²+0.3890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2579
_reflns_number_total             3256
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3003367_si_007.cif
_cod_data_source_block           Pyrogallol_Nicotinamide
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4506458
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 0.73575(17) 0.03754(8) 0.3692(2) 0.0160(4) Uani 1 1 d .
C2 C 0.80628(16) 0.09671(9) 0.3840(2) 0.0158(4) Uani 1 1 d .
C3 C 0.76530(16) 0.15789(9) 0.4361(2) 0.0161(4) Uani 1 1 d .
C4 C 0.65139(16) 0.16046(9) 0.4690(2) 0.0187(4) Uani 1 1 d .
H4A H 0.6222 0.2024 0.5027 0.022 Uiso 1 1 calc R
C5 C 0.58067(17) 0.10164(9) 0.4524(2) 0.0190(4) Uani 1 1 d .
H5A H 0.5026 0.1034 0.4747 0.023 Uiso 1 1 calc R
C6 C 0.62232(16) 0.03983(9) 0.4034(2) 0.0181(4) Uani 1 1 d .
H6A H 0.5735 -0.0004 0.3936 0.022 Uiso 1 1 calc R
C7 C 0.27046(16) 0.19468(9) 0.4741(2) 0.0171(4) Uani 1 1 d .
C8 C 0.16503(15) 0.22423(9) 0.3538(2) 0.0155(4) Uani 1 1 d .
C9 C 0.15499(16) 0.29522(9) 0.3438(2) 0.0164(4) Uani 1 1 d .
C10 C 0.24814(17) 0.33608(9) 0.4524(2) 0.0183(4) Uani 1 1 d .
H10 H 0.2410 0.3845 0.4447 0.022 Uiso 1 1 calc R
C11 C 0.35196(17) 0.30597(9) 0.5727(2) 0.0195(4) Uani 1 1 d .
H11 H 0.4155 0.3339 0.6487 0.023 Uiso 1 1 calc R
C12 C 0.36379(16) 0.23558(9) 0.5830(2) 0.0190(4) Uani 1 1 d .
H12 H 0.4358 0.2153 0.6645 0.023 Uiso 1 1 calc R
C13 C 0.20806(16) 0.55185(9) 0.6350(2) 0.0144(4) Uani 1 1 d .
C14 C 0.17851(16) 0.62028(9) 0.5999(2) 0.0166(4) Uani 1 1 d .
H14 H 0.1017 0.6365 0.6103 0.020 Uiso 1 1 calc R
C15 C 0.36089(17) 0.64141(9) 0.5381(2) 0.0190(4) Uani 1 1 d .
H15 H 0.4142 0.6725 0.5040 0.023 Uiso 1 1 calc R
C16 C 0.39831(17) 0.57412(9) 0.5709(2) 0.0195(4) Uani 1 1 d .
H16 H 0.4760 0.5594 0.5606 0.023 Uiso 1 1 calc R
C17 C 0.32033(16) 0.52869(9) 0.6192(2) 0.0176(4) Uani 1 1 d .
H17 H 0.3435 0.4820 0.6413 0.021 Uiso 1 1 calc R
C18 C 0.12548(16) 0.50248(9) 0.6903(2) 0.0163(4) Uani 1 1 d .
H1 H 0.752(2) -0.0568(13) 0.350(3) 0.051(8) Uiso 1 1 d .
H2 H 0.946(2) 0.1322(12) 0.345(3) 0.038(7) Uiso 1 1 d .
H3 H 0.796(2) 0.2563(13) 0.452(4) 0.055(8) Uiso 1 1 d .
H4 H 0.240(3) 0.1013(13) 0.395(4) 0.063(9) Uiso 1 1 d .
H5 H 0.088(2) 0.1478(14) 0.216(3) 0.057(8) Uiso 1 1 d .
H6 H 0.001(2) 0.2959(14) 0.166(4) 0.057(8) Uiso 1 1 d .
H1A H -0.019(2) 0.4925(12) 0.765(3) 0.044(7) Uiso 1 1 d .
H1B H 0.0097(19) 0.5721(11) 0.731(3) 0.028(6) Uiso 1 1 d .
N1 N 0.02727(14) 0.52584(8) 0.7305(2) 0.0177(4) Uani 1 1 d .
N2 N 0.25279(14) 0.66475(7) 0.5522(2) 0.0186(4) Uani 1 1 d .
O1 O 0.78326(12) -0.02026(6) 0.31527(18) 0.0219(3) Uani 1 1 d .
O2 O 0.91720(12) 0.09272(7) 0.34820(18) 0.0206(3) Uani 1 1 d .
O3 O 0.84393(11) 0.21245(6) 0.45360(17) 0.0207(3) Uani 1 1 d .
O4 O 0.28466(12) 0.12479(6) 0.49173(18) 0.0205(3) Uani 1 1 d .
O5 O 0.06588(11) 0.18723(7) 0.24473(17) 0.0185(3) Uani 1 1 d .
O6 O 0.05207(12) 0.32650(6) 0.23026(18) 0.0207(3) Uani 1 1 d .
O7 O 0.15193(12) 0.44025(6) 0.69548(17) 0.0203(3) 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
O1 C1 C6 123.92(16)
O1 C1 C2 116.31(16)
C6 C1 C2 119.75(16)
O2 C2 C1 118.22(16)
O2 C2 C3 121.26(16)
C1 C2 C3 120.52(16)
O3 C3 C4 124.24(16)
O3 C3 C2 115.90(16)
C4 C3 C2 119.86(16)
C5 C4 C3 119.55(17)
C4 C5 C6 120.87(17)
C1 C6 C5 119.45(16)
O4 C7 C12 117.92(16)
O4 C7 C8 121.83(16)
C12 C7 C8 120.24(16)
O5 C8 C9 116.78(15)
O5 C8 C7 123.94(16)
C9 C8 C7 119.25(16)
O6 C9 C10 118.14(16)
O6 C9 C8 121.30(16)
C10 C9 C8 120.53(16)
C9 C10 C11 119.59(17)
C12 C11 C10 120.53(17)
C11 C12 C7 119.84(17)
C14 C13 C17 117.90(16)
C14 C13 C18 123.17(16)
C17 C13 C18 118.93(16)
N2 C14 C13 123.31(16)
N2 C15 C16 122.89(17)
C15 C16 C17 118.61(17)
C16 C17 C13 119.42(16)
O7 C18 N1 122.48(17)
O7 C18 C13 118.24(16)
N1 C18 C13 119.27(16)
C15 N2 C14 117.86(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.372(2)
C1 C6 1.388(3)
C1 C2 1.388(2)
C2 O2 1.367(2)
C2 C3 1.389(2)
C3 O3 1.367(2)
C3 C4 1.388(3)
C4 C5 1.383(2)
C5 C6 1.393(3)
C7 O4 1.378(2)
C7 C12 1.385(2)
C7 C8 1.393(2)
C8 O5 1.383(2)
C8 C9 1.393(2)
C9 O6 1.369(2)
C9 C10 1.383(2)
C10 C11 1.386(3)
C11 C12 1.383(3)
C13 C14 1.386(2)
C13 C17 1.387(2)
C13 C18 1.496(2)
C14 N2 1.339(2)
C15 N2 1.339(2)
C15 C16 1.381(3)
C16 C17 1.383(3)
C18 O7 1.250(2)
C18 N1 1.324(2)
