#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/47/7214770.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_7214770
loop_
_publ_author_name
'Veidis, Mikelis V.'
'Orola, Liana'
'Mutikainen, Ilpo'
'Sarcevica, Inese'
_publ_section_title
;
 The conformation of pyrogallol as a result of cocrystallization with
 N-heterocyclic bases
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              7253
_journal_paper_doi               10.1039/c2ce25821h
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C18 H14 N2 O3'
_chemical_formula_sum            'C18 H14 N2 O3'
_chemical_formula_weight         306.32
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6419(3)
_cell_length_b                   12.6654(4)
_cell_length_c                   22.1187(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    173
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2981.25(15)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6319
_diffrn_reflns_theta_full        27.475
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         1.841
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       210(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.0001594
_refine_ls_shift/su_mean         0.0000169
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Quasi-Unit weights
W = 1.0 or 1./2F
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2451
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1134
_reflns_limit_h_max              13
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2019
_reflns_number_total             3414
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.20
_oxford_diffrn_Wilson_scale      19.61
_oxford_refine_ls_r_factor_ref   0.0473
_oxford_refine_ls_scale          0.2407(4)
_oxford_reflns_number_all        3413
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            c2ce25821h.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               7214770
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
CONT EXTPARAM
RIDE O ( 1,X'S) H ( 11,X'S)
RIDE C ( 3,X'S) H ( 31,X'S)
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 51,X'S)
RIDE O ( 8,X'S) H ( 81,X'S)
RIDE O ( 9,X'S) H ( 91,X'S)
RIDE C ( 14,X'S) H ( 141,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 19,X'S) H ( 191,X'S)
RIDE C ( 21,X'S) H ( 211,X'S)
RIDE C ( 22,X'S) H ( 221,X'S)
RIDE C ( 23,X'S) H ( 231,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 0.7856(2) 0.6581(2) 0.35431(12) 0.0323 1.0000 Uani .
C2 C 0.8584(3) 0.5870(3) 0.32284(16) 0.0251 1.0000 Uani .
C3 C 0.9570(4) 0.6257(3) 0.28818(17) 0.0291 1.0000 Uani .
C4 C 1.0319(4) 0.5568(3) 0.25614(18) 0.0310 1.0000 Uani .
C5 C 1.0103(4) 0.4492(3) 0.25763(18) 0.0307 1.0000 Uani .
C6 C 0.9111(4) 0.4111(3) 0.29137(16) 0.0265 1.0000 Uani .
C7 C 0.8356(3) 0.4792(3) 0.32489(16) 0.0241 1.0000 Uani .
O8 O 0.7362(2) 0.4357(2) 0.35620(11) 0.0297 1.0000 Uani .
O9 O 0.8862(3) 0.3053(2) 0.29136(13) 0.0392 1.0000 Uani .
N10 N 0.7688(3) 0.4940(3) 0.47468(14) 0.0272 1.0000 Uani .
C11 C 0.6940(3) 0.5485(3) 0.51362(16) 0.0254 1.0000 Uani .
C12 C 0.5928(4) 0.6112(3) 0.48957(18) 0.0270 1.0000 Uani .
N13 N 0.5815(3) 0.6208(3) 0.42848(15) 0.0293 1.0000 Uani .
C14 C 0.4841(4) 0.6747(3) 0.4070(2) 0.0368 1.0000 Uani .
C15 C 0.3936(4) 0.7227(3) 0.4434(2) 0.0397 1.0000 Uani .
C16 C 0.4067(4) 0.7170(3) 0.5043(2) 0.0406 1.0000 Uani .
C17 C 0.5081(4) 0.6600(3) 0.52992(19) 0.0320 1.0000 Uani .
C18 C 0.5291(5) 0.6516(4) 0.5937(2) 0.0415 1.0000 Uani .
C19 C 0.6269(4) 0.5971(4) 0.61598(19) 0.0408 1.0000 Uani .
C20 C 0.7116(4) 0.5432(3) 0.57688(17) 0.0318 1.0000 Uani .
C21 C 0.8127(4) 0.4832(3) 0.5985(2) 0.0404 1.0000 Uani .
C22 C 0.8879(4) 0.4308(3) 0.5592(2) 0.0402 1.0000 Uani .
C23 C 0.8618(4) 0.4371(3) 0.49742(19) 0.0331 1.0000 Uani .
H31 H 0.9735 0.6980 0.2864 0.0337 1.0000 Uiso R
H41 H 1.0990 0.5831 0.2343 0.0369 1.0000 Uiso R
H51 H 1.0619 0.4027 0.2369 0.0359 1.0000 Uiso R
H141 H 0.4735 0.6790 0.3647 0.0430 1.0000 Uiso R
H151 H 0.3235 0.7583 0.4252 0.0470 1.0000 Uiso R
H161 H 0.3486 0.7509 0.5283 0.0482 1.0000 Uiso R
H181 H 0.4772 0.6863 0.6203 0.0489 1.0000 Uiso R
H191 H 0.6421 0.5939 0.6576 0.0481 1.0000 Uiso R
H211 H 0.8267 0.4797 0.6400 0.0469 1.0000 Uiso R
H221 H 0.9532 0.3903 0.5736 0.0478 1.0000 Uiso R
H231 H 0.9137 0.3994 0.4714 0.0383 1.0000 Uiso R
H91 H 0.8217 0.2869 0.3083 0.0568 1.0000 Uiso R
H11 H 0.7219 0.6295 0.3691 0.0474 1.0000 Uiso R
H81 H 0.7340 0.4598 0.3920 0.0446 1.0000 Uiso R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 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_publ_flag
C2 O1 H11 111.8 no
O1 C2 C3 118.3(3) yes
O1 C2 C7 121.9(3) yes
C3 C2 C7 119.8(4) yes
C2 C3 C4 119.8(4) yes
C2 C3 H31 120.8 no
C4 C3 H31 119.4 no
C3 C4 C5 121.1(4) yes
C3 C4 H41 119.1 no
C5 C4 H41 119.8 no
C4 C5 C6 119.0(4) yes
C4 C5 H51 121.1 no
C6 C5 H51 120.0 no
C5 C6 C7 120.8(4) yes
C5 C6 O9 119.4(3) yes
C7 C6 O9 119.7(3) yes
C6 C7 C2 119.4(3) yes
C6 C7 O8 117.5(3) yes
C2 C7 O8 122.9(3) yes
C7 O8 H81 110.3 no
C6 O9 H91 116.3 no
C11 N10 C23 118.2(3) yes
N10 C11 C12 118.9(3) yes
N10 C11 C20 121.7(4) yes
C12 C11 C20 119.4(3) yes
C11 C12 N13 118.8(3) yes
C11 C12 C17 119.1(4) yes
N13 C12 C17 122.1(4) yes
C12 N13 C14 118.0(3) yes
N13 C14 C15 123.8(4) yes
N13 C14 H141 118.6 no
C15 C14 H141 117.6 no
C14 C15 C16 118.6(4) yes
C14 C15 H151 120.0 no
C16 C15 H151 121.3 no
C15 C16 C17 120.1(4) yes
C15 C16 H161 118.5 no
C17 C16 H161 121.4 no
C16 C17 C12 117.2(4) yes
C16 C17 C18 123.4(4) yes
C12 C17 C18 119.4(4) yes
C17 C18 C19 121.4(4) yes
C17 C18 H181 120.1 no
C19 C18 H181 118.4 no
C18 C19 C20 120.9(4) yes
C18 C19 H191 121.2 no
C20 C19 H191 117.9 no
C19 C20 C11 119.6(4) yes
C19 C20 C21 122.6(4) yes
C11 C20 C21 117.7(4) yes
C20 C21 C22 120.0(4) yes
C20 C21 H211 119.0 no
C22 C21 H211 121.0 no
C21 C22 C23 118.8(4) yes
C21 C22 H221 119.8 no
C23 C22 H221 121.3 no
C22 C23 N10 123.5(4) yes
C22 C23 H231 117.2 no
N10 C23 H231 119.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.377(4) yes
O1 H11 0.836 no
C2 C3 1.388(5) yes
C2 C7 1.388(5) yes
C3 C4 1.378(5) yes
C3 H31 0.933 no
C4 C5 1.382(5) yes
C4 H41 0.924 no
C5 C6 1.380(5) yes
C5 H51 0.926 no
C6 C7 1.393(5) yes
C6 O9 1.366(5) yes
C7 O8 1.380(4) yes
O8 H81 0.849 no
O9 H91 0.815 no
N10 C11 1.361(5) yes
N10 C23 1.324(5) yes
C11 C12 1.439(5) yes
C11 C20 1.413(5) yes
C12 N13 1.362(5) yes
C12 C17 1.412(5) yes
N13 C14 1.329(5) yes
C14 C15 1.395(6) yes
C14 H141 0.942 no
C15 C16 1.358(6) yes
C15 H151 0.959 no
C16 C17 1.416(6) yes
C16 H161 0.920 no
C17 C18 1.432(6) yes
C18 C19 1.343(6) yes
C18 H181 0.920 no
C19 C20 1.423(6) yes
C19 H191 0.936 no
C20 C21 1.401(6) yes
C21 C22 1.356(6) yes
C21 H211 0.932 no
C22 C23 1.397(6) yes
C22 H221 0.920 no
C23 H231 0.929 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O9 H91 O1 3_645 147.84(10) 0.815 2.236 2.959(6) yes
O1 H11 N13 . 153.02(12) 0.836 1.991 2.763(6) yes
O8 H81 N10 . 165.15(12) 0.849 1.916 2.745(6) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198239
#BEGIN Loops that were not found in dictionaries:
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
8 0 22 x
#END Loops that were not found in dictionaries
