#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/96/4509630.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509630
loop_
_publ_author_name
'Basu, Tannistha'
'Sparkes, Hazel A.'
'Mondal, Raju'
_publ_section_title
;
 Construction of Extended Molecular Networks with Heterosynthons in
 Cocrystals of Pyrazole and Acids
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5164
_journal_paper_doi               10.1021/cg900559q
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C20 H22 N4 O6'
_chemical_formula_weight         414.42
_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                 101.528(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.9936(11)
_cell_length_b                   15.8382(11)
_cell_length_c                   7.7126(5)
_cell_measurement_reflns_used    3966
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      2.55
_cell_volume                     1914.3(2)
_computing_cell_refinement       'Bruker APEX-2'
_computing_data_collection       'Bruker APEX-2'
_computing_data_reduction        'Bruker SHELXTL'
_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      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-2 CCD area detector'
_diffrn_measurement_method       '/w 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  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            24214
_diffrn_reflns_theta_full        26.53
_diffrn_reflns_theta_max         26.53
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.848970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS v.2.03 (Bruker, 2001), R(int)=0.0537 before correction'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rhombohedral
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0387
_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)+(0.0454P)²+0.4992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                2993
_reflns_number_total             3955
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg900559qsup2.cif
_cod_data_source_block           09tba008
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4509630
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
O5 O 0.31436(7) 0.07528(7) 0.17264(16) 0.0339(3) Uani 1 1 d
O1 O 0.47039(7) -0.32654(7) 0.51452(15) 0.0291(3) Uani 1 1 d
O4 O 0.11201(7) -0.16847(7) 0.13864(16) 0.0320(3) Uani 1 1 d
O2 O 0.53079(7) -0.20869(7) 0.64022(15) 0.0288(3) Uani 1 1 d
O6 O 0.45278(8) 0.04862(8) 0.27616(17) 0.0369(3) Uani 1 1 d
O3 O 0.16945(8) -0.29772(7) 0.16126(18) 0.0373(3) Uani 1 1 d
C14 C 0.26068(10) -0.18181(10) 0.2499(2) 0.0230(3) Uani 1 1 d
C12 C 0.40470(10) -0.19574(10) 0.4176(2) 0.0223(3) Uani 1 1 d
C16 C 0.35651(10) -0.06325(10) 0.2767(2) 0.0237(3) Uani 1 1 d
C15 C 0.27640(10) -0.09763(10) 0.2158(2) 0.0233(3) Uani 1 1 d
C19 C 0.17360(10) -0.21544(10) 0.1790(2) 0.0260(4) Uani 1 1 d
C17 C 0.42024(10) -0.11176(10) 0.3791(2) 0.0237(3) Uani 1 1 d
C18 C 0.47293(10) -0.24838(10) 0.5309(2) 0.0236(3) Uani 1 1 d
C20 C 0.37109(10) 0.02724(10) 0.2355(2) 0.0264(4) Uani 1 1 d
C13 C 0.32537(10) -0.23106(10) 0.3488(2) 0.0227(3) Uani 1 1 d
N4 N 0.36350(9) 0.31963(9) 0.19670(18) 0.0295(3) Uani 1 1 d
N2 N -0.02114(9) 0.35573(9) -0.0178(2) 0.0323(3) Uani 1 1 d
N1 N -0.00131(9) 0.39112(9) 0.1455(2) 0.0300(3) Uani 1 1 d
C2 C 0.10571(10) 0.42137(10) 0.0176(2) 0.0239(3) Uani 1 1 d
N3 N 0.38774(9) 0.39402(9) 0.27524(19) 0.0306(3) Uani 1 1 d
C4 C 0.33029(10) 0.45394(11) 0.2125(2) 0.0274(4) Uani 1 1 d
C5 C 0.26660(10) 0.41556(10) 0.0887(2) 0.0236(3) Uani 1 1 d
C6 C 0.28954(10) 0.33070(10) 0.0825(2) 0.0257(4) Uani 1 1 d
C3 C 0.04402(10) 0.37391(10) -0.0961(2) 0.0285(4) Uani 1 1 d
C11 C 0.24510(13) 0.26050(12) -0.0251(3) 0.0342(4) Uani 1 1 d
C10 C 0.33995(13) 0.54284(12) 0.2749(3) 0.0357(4) Uani 1 1 d
C7 C 0.18813(10) 0.45671(11) -0.0178(2) 0.0259(4) Uani 1 1 d
C1 C 0.07454(10) 0.43073(10) 0.1716(2) 0.0265(4) Uani 1 1 d
C9 C 0.04402(15) 0.34258(15) -0.2789(3) 0.0421(5) Uani 1 1 d
C8 C 0.11158(13) 0.47523(13) 0.3397(3) 0.0351(4) Uani 1 1 d
H17 H 0.4742(11) -0.0866(11) 0.423(2) 0.023(4) Uiso 1 1 d
H15 H 0.2334(11) -0.0638(11) 0.148(2) 0.025(4) Uiso 1 1 d
H13 H 0.3156(10) -0.2905(11) 0.375(2) 0.027(4) Uiso 1 1 d
H7B H 0.1917(11) 0.5172(12) 0.006(2) 0.030(5) Uiso 1 1 d
H7A H 0.1907(11) 0.4496(11) -0.142(3) 0.032(5) Uiso 1 1 d
H111 H -0.0360(13) 0.3819(13) 0.224(3) 0.046(6) Uiso 1 1 d
H333 H 0.4398(14) 0.3928(14) 0.360(3) 0.058(6) Uiso 1 1 d
H11C H 0.1876(14) 0.2518(13) -0.001(3) 0.050(6) Uiso 1 1 d
H8C H 0.1603(13) 0.4450(13) 0.405(3) 0.046(6) Uiso 1 1 d
H8B H 0.1307(14) 0.5342(16) 0.313(3) 0.060(7) Uiso 1 1 d
H11B H 0.2768(13) 0.2107(14) 0.002(3) 0.047(6) Uiso 1 1 d
H8A H 0.0696(14) 0.4804(13) 0.417(3) 0.054(6) Uiso 1 1 d
H11A H 0.2379(14) 0.2756(14) -0.152(3) 0.056(6) Uiso 1 1 d
H444 H 0.3989(14) 0.2678(15) 0.238(3) 0.063(7) Uiso 1 1 d
H10C H 0.3933(18) 0.5497(17) 0.353(4) 0.082(8) Uiso 1 1 d
H10B H 0.2932(18) 0.5570(17) 0.338(4) 0.090(9) Uiso 1 1 d
H10A H 0.3327(17) 0.5801(19) 0.180(4) 0.092(9) Uiso 1 1 d
H9C H 0.0624(17) 0.2832(19) -0.279(4) 0.087(9) Uiso 1 1 d
H9B H 0.0880(16) 0.3705(16) -0.328(3) 0.071(8) Uiso 1 1 d
H9A H -0.0121(18) 0.3456(16) -0.356(4) 0.080(8) Uiso 1 1 d
H3 H 0.1025(19) -0.3177(18) 0.095(4) 0.098(9) Uiso 1 1 d
H6 H 0.4607(17) 0.112(2) 0.288(4) 0.094(9) Uiso 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
C20 O6 H6 111.9(15)
C19 O3 H3 110.4(15)
C15 C14 C13 119.80(14)
C15 C14 C19 117.66(14)
C13 C14 C19 122.54(14)
C13 C12 C17 119.32(14)
C13 C12 C18 119.90(14)
C17 C12 C18 120.77(14)
C15 C16 C17 119.94(15)
C15 C16 C20 118.52(14)
C17 C16 C20 121.50(14)
C16 C15 C14 120.16(15)
C16 C15 H15 119.2(10)
C14 C15 H15 120.6(10)
O4 C19 O3 123.82(15)
O4 C19 C14 121.46(15)
O3 C19 C14 114.71(14)
C16 C17 C12 120.40(15)
C16 C17 H17 118.8(10)
C12 C17 H17 120.8(10)
O1 C18 O2 123.94(14)
O1 C18 C12 119.12(14)
O2 C18 C12 116.95(13)
O5 C20 O6 124.01(15)
O5 C20 C16 123.49(15)
O6 C20 C16 112.50(14)
C12 C13 C14 120.27(15)
C12 C13 H13 118.6(10)
C14 C13 H13 121.1(10)
C6 N4 N3 108.59(14)
C6 N4 H444 132.7(13)
N3 N4 H444 118.5(13)
C3 N2 N1 105.76(13)
C1 N1 N2 111.62(15)
C1 N1 H111 128.8(13)
N2 N1 H111 119.3(13)
C1 C2 C3 105.37(14)
C1 C2 C7 126.41(15)
C3 C2 C7 128.22(15)
C4 N3 N4 110.00(14)
C4 N3 H333 134.9(14)
N4 N3 H333 115.1(14)
N3 C4 C5 107.06(15)
N3 C4 C10 122.27(16)
C5 C4 C10 130.67(16)
C4 C5 C6 106.45(14)
C4 C5 C7 127.08(15)
C6 C5 C7 126.47(15)
N4 C6 C5 107.90(15)
N4 C6 C11 122.19(15)
C5 C6 C11 129.91(15)
N2 C3 C2 110.40(15)
N2 C3 C9 120.11(16)
C2 C3 C9 129.48(17)
C6 C11 H11C 111.3(12)
C6 C11 H11B 109.2(13)
H11C C11 H11B 109.0(18)
C6 C11 H11A 108.7(13)
H11C C11 H11A 106.8(17)
H11B C11 H11A 111.8(18)
C4 C10 H10C 109.7(16)
C4 C10 H10B 109.4(16)
H10C C10 H10B 109(2)
C4 C10 H10A 110.9(18)
H10C C10 H10A 113(2)
H10B C10 H10A 105(2)
C5 C7 C2 113.88(13)
C5 C7 H7B 108.2(10)
C2 C7 H7B 110.5(10)
C5 C7 H7A 107.0(10)
C2 C7 H7A 110.2(10)
H7B C7 H7A 106.7(15)
N1 C1 C2 106.85(15)
N1 C1 C8 122.76(16)
C2 C1 C8 130.39(16)
C3 C9 H9C 111.8(16)
C3 C9 H9B 110.7(15)
H9C C9 H9B 101(2)
C3 C9 H9A 112.8(15)
H9C C9 H9A 107(2)
H9B C9 H9A 113(2)
C1 C8 H8C 111.0(12)
C1 C8 H8B 109.8(13)
H8C C8 H8B 108.6(17)
C1 C8 H8A 111.5(13)
H8C C8 H8A 107.5(17)
H8B C8 H8A 108.4(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O5 C20 1.2090(19)
O1 C18 1.2442(19)
O4 C19 1.2240(19)
O2 C18 1.2847(18)
O6 C20 1.325(2)
O6 H6 1.02(3)
O3 C19 1.311(2)
O3 H3 1.14(3)
C14 C15 1.392(2)
C14 C13 1.395(2)
C14 C19 1.489(2)
C12 C13 1.391(2)
C12 C17 1.396(2)
C12 C18 1.506(2)
C16 C15 1.385(2)
C16 C17 1.390(2)
C16 C20 1.496(2)
C15 H15 0.942(17)
C17 H17 0.950(17)
C13 H13 0.981(18)
N4 C6 1.338(2)
N4 N3 1.346(2)
N4 H444 1.01(2)
N2 C3 1.336(2)
N2 N1 1.357(2)
N1 C1 1.345(2)
N1 H111 0.91(2)
C2 C1 1.385(2)
C2 C3 1.400(2)
C2 C7 1.506(2)
N3 C4 1.342(2)
N3 H333 0.95(2)
C4 C5 1.389(2)
C4 C10 1.486(3)
C5 C6 1.397(2)
C5 C7 1.504(2)
C6 C11 1.481(2)
C3 C9 1.495(3)
C11 H11C 0.98(2)
C11 H11B 0.94(2)
C11 H11A 0.99(2)
C10 H10C 0.95(3)
C10 H10B 1.00(3)
C10 H10A 0.93(3)
C7 H7B 0.976(19)
C7 H7A 0.977(18)
C1 C8 1.490(2)
C9 H9C 0.99(3)
C9 H9B 0.97(3)
C9 H9A 0.98(3)
C8 H8C 0.97(2)
C8 H8B 1.02(2)
C8 H8A 0.99(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146974
