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#$Date: 2022-03-23 12:17:56 +0200 (Wed, 23 Mar 2022) $
#$Revision: 273930 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104847.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_8104847
loop_
_publ_author_name
'Li, Jin'
'Zuo, Zhenyu'
'Chen, Yan'
'Liu, Yali'
'Yin, Dachuan'
_publ_section_title
;
 The crystal structure of
 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine,
 C22H15N3O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              413
_journal_page_last               415
_journal_paper_doi               10.1515/ncrs-2020-0583
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C22 H15 N3 O2'
_chemical_formula_sum            'C22 H15 N3 O2'
_chemical_formula_weight         353.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                110.002(2)
_cell_angle_beta                 98.837(2)
_cell_angle_gamma                94.263(2)
_cell_formula_units_Z            2
_cell_length_a                   5.7613(4)
_cell_length_b                   12.3545(7)
_cell_length_c                   13.3427(8)
_cell_measurement_reflns_used    6030
_cell_measurement_temperature    153
_cell_measurement_theta_max      68.179
_cell_measurement_theta_min      3.591
_cell_volume                     873.56(10)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      153.0
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7418
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.370
_diffrn_reflns_theta_min         3.844
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1049 before and 0.0548 after correction. The Ratio of minimum to maximum transmission is 0.7673. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0749P)²+0.1647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2651
_reflns_number_total             3066
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0583_suppl.cif
_cod_data_source_block           s
_cod_original_cell_volume        873.55(9)
_cod_database_code               8104847
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.815
_shelx_estimated_absorpt_t_min   0.717
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22)
2.c :
 C20(H20)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6791(3) 0.80235(13) 0.49698(11) 0.0340(3) Uani 1 1 d . . . . .
C2 C 0.5614(3) 0.68237(12) 0.57501(11) 0.0322(3) Uani 1 1 d . . . . .
C3 C 0.9145(2) 0.79381(12) 0.64194(10) 0.0325(3) Uani 1 1 d . . . . .
C4 C 0.2665(3) 0.70929(13) 0.15173(11) 0.0378(4) Uani 1 1 d . . . . .
C5 C 1.1372(3) 0.83424(12) 0.72438(11) 0.0340(3) Uani 1 1 d . . . . .
C6 C 0.2154(3) 0.47962(13) 0.64986(11) 0.0372(3) Uani 1 1 d . . . . .
C7 C 0.4465(3) 0.81493(13) 0.33863(11) 0.0369(4) Uani 1 1 d . . . . .
C8 C 1.5257(3) 0.94723(14) 0.79300(12) 0.0418(4) Uani 1 1 d . . . . .
H8 H 1.6484 0.9989 0.7866 0.050 Uiso 1 1 calc R . . . .
C9 C 0.0689(3) 0.76997(14) 0.16714(12) 0.0399(4) Uani 1 1 d . . . . .
C10 C 0.2478(3) 0.87277(14) 0.35597(12) 0.0413(4) Uani 1 1 d . . . . .
H10 H 0.2422 0.9269 0.4258 0.050 Uiso 1 1 calc R . . . .
C11 C 1.1665(3) 0.79735(14) 0.81235(12) 0.0406(4) Uani 1 1 d . . . . .
H11 H 1.0441 0.7461 0.8194 0.049 Uiso 1 1 calc R . . . .
C12 C 1.3179(3) 0.90983(13) 0.71503(11) 0.0371(3) Uani 1 1 d . . . . .
H12 H 1.2991 0.9358 0.6553 0.045 Uiso 1 1 calc R . . . .
C13 C 0.4305(3) 0.55656(13) 0.66080(11) 0.0366(3) Uani 1 1 d . . . . .
H13A H 0.4642 0.6201 0.7328 0.044 Uiso 1 1 calc R . . . .
H13B H 0.5677 0.5126 0.6537 0.044 Uiso 1 1 calc R . . . .
C14 C 1.5539(3) 0.90919(15) 0.87986(12) 0.0445(4) Uani 1 1 d . . . . .
H14 H 1.6968 0.9340 0.9325 0.053 Uiso 1 1 calc R . . . .
C15 C 0.4586(3) 0.73378(13) 0.24121(12) 0.0382(3) Uani 1 1 d . . . . .
H15 H 0.5932 0.6939 0.2327 0.046 Uiso 1 1 calc R . . . .
C16 C 1.3748(3) 0.83532(15) 0.89021(12) 0.0462(4) Uani 1 1 d . . . . .
H16 H 1.3937 0.8104 0.9505 0.055 Uiso 1 1 calc R . . . .
C17 C 0.2738(3) 0.62900(15) 0.04751(13) 0.0464(4) Uani 1 1 d . . . . .
H17 H 0.4063 0.5880 0.0365 0.056 Uiso 1 1 calc R . . . .
C18 C -0.1180(3) 0.74880(17) 0.07634(14) 0.0499(4) Uani 1 1 d . . . . .
H18 H -0.2515 0.7894 0.0853 0.060 Uiso 1 1 calc R . . . .
C19 C 0.0620(3) 0.85032(15) 0.27122(13) 0.0426(4) Uani 1 1 d . . . . .
H19 H -0.0732 0.8892 0.2825 0.051 Uiso 1 1 calc R . . . .
C20 C 0.0421(3) 0.41615(14) 0.63930(13) 0.0438(4) Uani 1 1 d . . . . .
H20 H -0.0972 0.3651 0.6308 0.053 Uiso 1 1 calc R . . . .
C21 C 0.0894(4) 0.61021(17) -0.03798(13) 0.0551(5) Uani 1 1 d . . . . .
H21 H 0.0944 0.5558 -0.1077 0.066 Uiso 1 1 calc R . . . .
C22 C -0.1065(3) 0.67124(19) -0.02254(14) 0.0573(5) Uani 1 1 d . . . . .
H22 H -0.2324 0.6579 -0.0822 0.069 Uiso 1 1 calc R . . . .
N1 N 0.8839(2) 0.84255(11) 0.56690(9) 0.0352(3) Uani 1 1 d . . . . .
N2 N 0.7583(2) 0.71178(10) 0.64955(9) 0.0336(3) Uani 1 1 d . . . . .
N3 N 0.5076(2) 0.72386(10) 0.49517(9) 0.0334(3) Uani 1 1 d . . . . .
O1 O 0.65067(19) 0.85193(10) 0.42123(8) 0.0420(3) Uani 1 1 d . . . . .
O2 O 0.38915(18) 0.60368(9) 0.57509(7) 0.0365(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 O1 112.92(12) . .
N3 C1 N1 128.24(13) . .
N3 C1 O1 118.83(12) . .
N2 C2 N3 127.12(12) . .
N2 C2 O2 120.07(12) . .
O2 C2 N3 112.80(12) . .
N1 C3 C5 117.33(12) . .
N1 C3 N2 125.12(13) . .
N2 C3 C5 117.55(12) . .
C9 C4 C15 118.99(14) . .
C9 C4 C17 119.46(14) . .
C17 C4 C15 121.50(16) . .
C11 C5 C3 119.93(13) . .
C11 C5 C12 119.39(13) . .
C12 C5 C3 120.67(13) . .
C20 C6 C13 178.84(17) . .
C10 C7 O1 118.50(14) . .
C15 C7 C10 122.39(14) . .
C15 C7 O1 118.69(15) . .
C12 C8 H8 120.0 . .
C14 C8 H8 120.0 . .
C14 C8 C12 120.03(14) . .
C4 C9 C18 118.77(16) . .
C4 C9 C19 119.42(14) . .
C19 C9 C18 121.80(16) . .
C7 C10 H10 120.4 . .
C19 C10 C7 119.23(15) . .
C19 C10 H10 120.4 . .
C5 C11 H11 119.9 . .
C5 C11 C16 120.20(14) . .
C16 C11 H11 119.9 . .
C5 C12 H12 120.0 . .
C8 C12 C5 120.09(13) . .
C8 C12 H12 120.0 . .
C6 C13 H13A 110.3 . .
C6 C13 H13B 110.3 . .
H13A C13 H13B 108.6 . .
O2 C13 C6 107.06(11) . .
O2 C13 H13A 110.3 . .
O2 C13 H13B 110.3 . .
C8 C14 H14 119.9 . .
C16 C14 C8 120.18(14) . .
C16 C14 H14 119.9 . .
C4 C15 H15 120.4 . .
C7 C15 C4 119.14(15) . .
C7 C15 H15 120.4 . .
C11 C16 H16 120.0 . .
C14 C16 C11 120.09(14) . .
C14 C16 H16 120.0 . .
C4 C17 H17 119.9 . .
C21 C17 C4 120.13(18) . .
C21 C17 H17 119.9 . .
C9 C18 H18 119.8 . .
C22 C18 C9 120.50(18) . .
C22 C18 H18 119.8 . .
C9 C19 H19 119.6 . .
C10 C19 C9 120.75(16) . .
C10 C19 H19 119.6 . .
C6 C20 H20 180.0 . .
C17 C21 H21 119.9 . .
C17 C21 C22 120.29(17) . .
C22 C21 H21 119.9 . .
C18 C22 C21 120.85(16) . .
C18 C22 H22 119.6 . .
C21 C22 H22 119.6 . .
C1 N1 C3 113.48(12) . .
C2 N2 C3 114.06(12) . .
C1 N3 C2 111.95(12) . .
C1 O1 C7 119.62(10) . .
C2 O2 C13 116.38(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.3293(19) .
C1 N3 1.3234(18) .
C1 O1 1.3458(17) .
C2 N2 1.3239(19) .
C2 N3 1.3377(19) .
C2 O2 1.3370(17) .
C3 C5 1.4836(19) .
C3 N1 1.3304(19) .
C3 N2 1.3454(18) .
C4 C9 1.412(2) .
C4 C15 1.428(2) .
C4 C17 1.414(2) .
C5 C11 1.389(2) .
C5 C12 1.396(2) .
C6 C13 1.461(2) .
C6 C20 1.182(2) .
C7 C10 1.402(2) .
C7 C15 1.359(2) .
C7 O1 1.4088(17) .
C8 H8 0.9500 .
C8 C12 1.391(2) .
C8 C14 1.384(2) .
C9 C18 1.427(2) .
C9 C19 1.413(2) .
C10 H10 0.9500 .
C10 C19 1.368(2) .
C11 H11 0.9500 .
C11 C16 1.392(2) .
C12 H12 0.9500 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 O2 1.4477(17) .
C14 H14 0.9500 .
C14 C16 1.381(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 H17 0.9500 .
C17 C21 1.376(3) .
C18 H18 0.9500 .
C18 C22 1.355(3) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 H21 0.9500 .
C21 C22 1.406(3) .
C22 H22 0.9500 .
