#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/76/2207636.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2207636
loop_
_publ_author_name
'Xin Huang'
'Fuqun Zhao'
'Ru-Ji Wang'
'Fushi Zhang'
'Chen-Ho, Tung'
_publ_section_title
;
 3-(4-tert-Butylphenoxy)phthalonitrile
;
_journal_coeditor_code           SJ6137
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4384
_journal_page_last               o4386
_journal_paper_doi               10.1107/S1600536805035725
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H16 N2 O'
_chemical_formula_moiety         'C18 H16 N2 O'
_chemical_formula_sum            'C18 H16 N2 O'
_chemical_formula_weight         276.33
_chemical_melting_point          .393E-305
_chemical_name_systematic
;
3-(4-tert-Butylphenoxy)phthalonitrile
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.280(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7541(10)
_cell_length_b                   6.8132(5)
_cell_length_c                   13.5203(19)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.44
_cell_measurement_theta_min      5.14
_cell_volume                     793.45(16)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ω
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2265
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1621
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.001P)²+0.3P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                757
_reflns_number_total             1621
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj6137.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_sg_symbol_H-M      'P 21/m'
_cod_database_code               2207636
_cod_database_fobs_code          2207636
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.49659(16) 0.7500 0.74122(10) 0.0903(6) Uani d S 1 . . O
N1 0.8091(2) 0.7500 0.93367(17) 0.1123(9) Uani d S 1 . . N
N2 0.6044(3) 0.7500 1.17810(15) 0.1087(8) Uani d S 1 . . N
C1 0.6772(3) 0.7500 0.92400(16) 0.0761(7) Uani d S 1 . . C
C2 0.5358(3) 0.7500 1.09817(17) 0.0822(8) Uani d S 1 . . C
C3 0.5126(2) 0.7500 0.91419(15) 0.0642(6) Uani d S 1 . . C
C4 0.4433(2) 0.7500 0.99955(15) 0.0688(7) Uani d S 1 . . C
C5 0.2838(3) 0.7500 0.98960(17) 0.0808(8) Uani d S 1 . . C
H5A 0.2374 0.7500 1.0463 0.097 Uiso calc SR 1 . . H
C6 0.1934(3) 0.7500 0.89478(16) 0.0849(8) Uani d S 1 . . C
H6A 0.0858 0.7500 0.8881 0.102 Uiso calc SR 1 . . H
C7 0.2599(2) 0.7500 0.81046(16) 0.0785(8) Uani d S 1 . . C
H7A 0.1977 0.7500 0.7470 0.094 Uiso calc SR 1 . . H
C8 0.4200(2) 0.7500 0.81993(16) 0.0685(7) Uani d S 1 . . C
C9 0.4086(2) 0.7500 0.64393(15) 0.0764(8) Uani d S 1 . . C
C10 0.3686(2) 0.5798(3) 0.59695(12) 0.1054(7) Uani d . 1 . . C
H10A 0.3972 0.4614 0.6293 0.127 Uiso calc R 1 . . H
C11 0.2842(2) 0.5811(3) 0.49950(12) 0.1054(7) Uani d . 1 . . C
H11A 0.2577 0.4617 0.4677 0.127 Uiso calc R 1 . . H
C12 0.2387(2) 0.7500 0.44853(16) 0.0769(8) Uani d S 1 . . C
C13 0.1386(3) 0.7500 0.34446(17) 0.0905(9) Uani d SD 1 . . C
C14 0.1654(5) 0.5741(6) 0.2820(2) 0.190(2) Uani d PD 0.670(3) A 1 C
H14A 0.1101 0.5911 0.2146 0.285 Uiso calc PR 0.670(3) A 1 H
H14B 0.1289 0.4580 0.3106 0.285 Uiso calc PR 0.670(3) A 1 H
H14C 0.2744 0.5613 0.2812 0.285 Uiso calc PR 0.670(3) A 1 H
C15 -0.0267(4) 0.7500 0.3544(4) 0.211(4) Uani d SPD 0.670(3) A 1 C
H15A -0.0454 0.8612 0.3942 0.316 Uiso d PR 0.670(3) A 1 H
H15B -0.0931 0.7500 0.2897 0.316 Uiso d SPR 0.670(3) A 1 H
C14' 0.0334(9) 0.5794(14) 0.3348(6) 0.267(5) Uani d PD 0.330(3) A 2 C
H14D -0.0472 0.5964 0.2773 0.401 Uiso calc PR 0.330(3) A 2 H
H14E -0.0120 0.5683 0.3942 0.401 Uiso calc PR 0.330(3) A 2 H
H14F 0.0910 0.4623 0.3268 0.401 Uiso calc PR 0.330(3) A 2 H
C15' 0.2441(9) 0.7500 0.2731(5) 0.156(6) Uani d SPD 0.330(3) A 2 C
H15C 0.1831 0.7500 0.2067 0.233 Uiso d SPR 0.330(3) A 2 H
H15D 0.3084 0.8651 0.2821 0.233 Uiso d PR 0.330(3) A 2 H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C8 O1 C9 . . 118.10(16)
N1 C1 C3 . . 178.8(3)
N2 C2 C4 . . 177.4(3)
C8 C3 C4 . . 119.46(19)
C8 C3 C1 . . 120.2(2)
C4 C3 C1 . . 120.33(18)
C5 C4 C3 . . 120.08(19)
C5 C4 C2 . . 119.1(2)
C3 C4 C2 . . 120.9(2)
C4 C5 C6 . . 119.5(2)
C4 C5 H5A . . 120.2
C6 C5 H5A . . 120.2
C7 C6 C5 . . 121.0(2)
C7 C6 H6A . . 119.5
C5 C6 H6A . . 119.5
C6 C7 C8 . . 119.8(2)
C6 C7 H7A . . 120.1
C8 C7 H7A . . 120.1
O1 C8 C3 . . 115.64(18)
O1 C8 C7 . . 124.19(18)
C3 C8 C7 . . 120.2(2)
C10 C9 C10 . 4_575 120.1(2)
C10 C9 O1 . . 119.94(10)
C10 C9 O1 4_575 . 119.94(10)
C9 C10 C11 . . 119.59(18)
C9 C10 H10A . . 120.2
C11 C10 H10A . . 120.2
C12 C11 C10 . . 122.82(18)
C12 C11 H11A . . 118.6
C10 C11 H11A . . 118.6
C11 C12 C11 4_575 . 115.1(2)
C11 C12 C13 4_575 . 122.44(10)
C11 C12 C13 . . 122.44(10)
C15' C13 C14' . . 113.8(4)
C15' C13 C14' . 4_575 113.8(4)
C14' C13 C14' . 4_575 104.1(7)
C15' C13 C15 . . 144.2(4)
C14' C13 C15 . . 53.2(4)
C14' C13 C15 4_575 . 53.2(4)
C15' C13 C14 . . 56.4(2)
C14' C13 C14 . . 58.8(4)
C14' C13 C14 4_575 . 137.3(3)
C15 C13 C14 . . 107.7(2)
C15' C13 C14 . 4_575 56.4(2)
C14' C13 C14 . 4_575 137.3(3)
C14' C13 C14 4_575 4_575 58.8(4)
C15 C13 C14 . 4_575 107.7(2)
C14 C13 C14 . 4_575 105.2(3)
C15' C13 C12 . . 106.6(3)
C14' C13 C12 . . 109.3(3)
C14' C13 C12 4_575 . 109.3(3)
C15 C13 C12 . . 109.2(3)
C14 C13 C12 . . 113.37(17)
C14 C13 C12 4_575 . 113.37(17)
C13 C14 H14A . . 109.5
C13 C14 H14B . . 109.5
C13 C14 H14C . . 109.5
C13 C15 H15A . . 108.6
C13 C15 H15B . . 111.2
H15A C15 H15B . . 112.0
C13 C14' H14D . . 109.5
C13 C14' H14E . . 109.5
H14D C14' H14E . . 109.5
C13 C14' H14F . . 109.5
H14D C14' H14F . . 109.5
H14E C14' H14F . . 109.5
C13 C15' H15C . . 108.0
C13 C15' H15D . . 110.2
H15C C15' H15D . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C8 . 1.355(2)
O1 C9 . 1.401(2)
N1 C1 . 1.139(3)
N2 C2 . 1.139(3)
C1 C3 . 1.423(3)
C2 C4 . 1.431(3)
C3 C8 . 1.383(3)
C3 C4 . 1.397(3)
C4 C5 . 1.379(3)
C5 C6 . 1.381(3)
C5 H5A . 0.9300
C6 C7 . 1.370(3)
C6 H6A . 0.9300
C7 C8 . 1.384(3)
C7 H7A . 0.9300
C9 C10 . 1.338(2)
C9 C10 4_575 1.338(2)
C10 C11 . 1.391(2)
C10 H10A . 0.9300
C11 C12 . 1.364(2)
C11 H11A . 0.9300
C12 C11 4_575 1.364(2)
C12 C13 . 1.519(3)
C13 C15' . 1.449(8)
C13 C14' . 1.474(8)
C13 C14' 4_575 1.474(8)
C13 C15 . 1.477(5)
C13 C14 . 1.508(4)
C13 C14 4_575 1.508(4)
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C15 H15A . 0.9601
C15 H15B . 0.9599
C14' H14D . 0.9600
C14' H14E . 0.9600
C14' H14F . 0.9600
C15' H15C . 0.9599
C15' H15D . 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 711739
