#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/64/1516447.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_1516447
loop_
_publ_author_name
'Wackerly, Jay Wm.'
'Meyer, Joseph M.'
'Crannell, W. Christian'
'King, Sarah B.'
'Katz, Jeffrey L.'
_publ_section_title
;
 Selective Synthesis of Poly(m-phenylene oxides) over Oxacalixarenes
;
_journal_issue                   21
_journal_name_full               Macromolecules
_journal_page_first              8181
_journal_paper_doi               10.1021/ma901518w
_journal_volume                  42
_journal_year                    2009
_chemical_formula_moiety         'C15 H10 Cl2 N4 O2'
_chemical_formula_sum            'C15 H10 Cl2 N4 O2'
_chemical_formula_weight         349.17
_chemical_name_common            'compound 17'
_chemical_name_systematic
; 
 3,5-bis(2-chloro-6-pyrazoxy)toluene 
;
_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
_audit_creation_method           SHELXTL
_cell_angle_alpha                101.3410(10)
_cell_angle_beta                 101.8000(10)
_cell_angle_gamma                92.3920(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9301(6)
_cell_length_b                   7.9168(6)
_cell_length_c                   14.3648(12)
_cell_measurement_reflns_used    7150
_cell_measurement_temperature    191(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      1.48
_cell_volume                     753.63(11)
_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      191(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_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  0.0900
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7150
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0463
_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)+(0.0623P)²+0.1908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                3167
_reflns_number_total             3583
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ma901518w_si_002.cif
_cod_data_source_block           katz91bm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z 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      P-1
_cod_database_code               1516447
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
C1 C 0.8241(2) 0.2998(2) 0.79355(10) 0.0300(3) Uani 1 1 d .
C2 C 0.6045(3) 0.1791(2) 0.85979(12) 0.0364(4) Uani 1 1 d .
C3 C 0.7348(3) 0.2092(3) 0.94890(12) 0.0479(5) Uani 1 1 d .
H3 H 0.6969 0.1734 1.0024 0.057 Uiso 1 1 calc R
C4 C 0.9606(3) 0.3340(2) 0.88289(11) 0.0384(4) Uani 1 1 d .
H4 H 1.0875 0.3901 0.8882 0.046 Uiso 1 1 calc R
C5 C 0.8133(2) 0.2728(2) 0.62311(10) 0.0281(3) Uani 1 1 d .
C6 C 0.7935(2) 0.0946(2) 0.59643(10) 0.0287(3) Uani 1 1 d .
H6 H 0.8130 0.0263 0.6445 0.034 Uiso 1 1 calc R
C7 C 0.7441(2) 0.01603(19) 0.49768(10) 0.0268(3) Uani 1 1 d .
C8 C 0.7177(2) 0.11922(19) 0.42890(10) 0.0282(3) Uani 1 1 d .
H8 H 0.6852 0.0677 0.3615 0.034 Uiso 1 1 calc R
C9 C 0.7389(2) 0.29703(19) 0.45917(10) 0.0273(3) Uani 1 1 d .
C10 C 0.7865(2) 0.37801(19) 0.55646(10) 0.0273(3) Uani 1 1 d .
H10 H 0.8000 0.5004 0.5764 0.033 Uiso 1 1 calc R
C11 C 0.7263(2) -0.1778(2) 0.46664(12) 0.0329(3) Uani 1 1 d .
H11A H 0.6567 -0.2119 0.3983 0.049 Uiso 1 1 calc R
H11B H 0.6519 -0.2283 0.5071 0.049 Uiso 1 1 calc R
H11C H 0.8587 -0.2194 0.4743 0.049 Uiso 1 1 calc R
C12 C 0.5958(2) 0.37068(19) 0.30771(10) 0.0282(3) Uani 1 1 d .
C13 C 0.3012(2) 0.2689(2) 0.21420(12) 0.0335(3) Uani 1 1 d .
C14 C 0.3514(3) 0.3199(2) 0.13511(11) 0.0404(4) Uani 1 1 d .
H14 H 0.2595 0.2965 0.0743 0.048 Uiso 1 1 calc R
C15 C 0.6518(3) 0.4281(2) 0.23021(12) 0.0360(4) Uani 1 1 d .
H15 H 0.7790 0.4863 0.2394 0.043 Uiso 1 1 calc R
N1 N 0.6465(2) 0.22225(18) 0.78113(9) 0.0326(3) Uani 1 1 d .
N2 N 0.9140(3) 0.2886(3) 0.96001(10) 0.0501(4) Uani 1 1 d .
N3 N 0.4214(2) 0.29198(17) 0.30113(9) 0.0309(3) Uani 1 1 d .
N4 N 0.5281(2) 0.4016(2) 0.14369(10) 0.0418(3) Uani 1 1 d .
O1 O 0.88192(19) 0.35909(16) 0.72031(7) 0.0390(3) Uani 1 1 d .
O2 O 0.73212(19) 0.40632(15) 0.39325(8) 0.0373(3) Uani 1 1 d .
Cl1 Cl 0.06651(6) 0.16983(7) 0.20251(4) 0.05316(17) Uani 1 1 d .
Cl2 Cl 0.37032(7) 0.08050(8) 0.84851(4) 0.05571(18) 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'
Cl Cl 0.1484 0.1585 '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
N1 C1 O1 121.07(13)
N1 C1 C4 122.87(14)
O1 C1 C4 115.99(14)
N1 C2 C3 123.89(16)
N1 C2 Cl2 117.22(13)
C3 C2 Cl2 118.89(13)
N2 C3 C2 120.02(15)
N2 C4 C1 120.43(16)
C10 C5 C6 122.90(13)
C10 C5 O1 115.14(13)
C6 C5 O1 121.67(13)
C5 C6 C7 119.07(13)
C8 C7 C6 119.20(13)
C8 C7 C11 120.66(13)
C6 C7 C11 120.12(13)
C9 C8 C7 119.61(13)
C8 C9 C10 122.33(13)
C8 C9 O2 121.80(12)
C10 C9 O2 115.61(12)
C5 C10 C9 116.89(13)
N3 C12 O2 120.89(13)
N3 C12 C15 123.31(14)
O2 C12 C15 115.76(14)
N3 C13 C14 124.07(15)
N3 C13 Cl1 116.42(12)
C14 C13 Cl1 119.50(12)
N4 C14 C13 120.31(14)
N4 C15 C12 120.49(15)
C1 N1 C2 115.12(13)
C4 N2 C3 117.66(15)
C12 N3 C13 114.65(13)
C15 N4 C14 117.14(14)
C1 O1 C5 120.95(12)
C12 O2 C9 120.31(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.315(2)
C1 O1 1.3556(17)
C1 C4 1.400(2)
C2 N1 1.325(2)
C2 C3 1.379(3)
C2 Cl2 1.7339(17)
C3 N2 1.333(3)
C4 N2 1.324(2)
C5 C10 1.378(2)
C5 C6 1.380(2)
C5 O1 1.4031(17)
C6 C7 1.398(2)
C7 C8 1.390(2)
C7 C11 1.504(2)
C8 C9 1.381(2)
C9 C10 1.3837(19)
C9 O2 1.3982(17)
C12 N3 1.314(2)
C12 O2 1.3595(17)
C12 C15 1.399(2)
C13 N3 1.3264(19)
C13 C14 1.380(2)
C13 Cl1 1.7373(17)
C14 N4 1.332(2)
C15 N4 1.331(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139043556
