#------------------------------------------------------------------------------
#$Date: 2022-05-04 10:17:56 +0200 (Wed 04 de May de 2022) $
#$Revision: 274875 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/51/8105132.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_8105132
loop_
_publ_author_name
'Li, Jin'
'Chen, Yan'
'Wu, Ziqing'
'Liu, Yali'
'Yin, Dachuan'
'Zuo, Zhenyu'
_publ_section_title
;
 The crystal structure of
 2-phenyl-4,6-bis(prop-2-yn-1-yloxy)-1,3,5-triazine, C15H11N3O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              433
_journal_page_last               435
_journal_paper_doi               10.1515/ncrs-2019-0733
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C15 H11 N3 O2'
_chemical_formula_sum            'C15 H11 N3 O2'
_chemical_formula_weight         265.27
_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
_cell_angle_alpha                104.578(5)
_cell_angle_beta                 111.882(6)
_cell_angle_gamma                106.589(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4680(5)
_cell_length_b                   9.7578(5)
_cell_length_c                   10.2101(6)
_cell_measurement_reflns_used    1554
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      75.6310
_cell_measurement_theta_min      5.1030
_cell_volume                     686.77(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      250.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -49.00  -8.00   1.00    2.00    --  -40.08 125.00  30.00   41
  2  ω   -105.00 -16.00   1.00    2.00    --  -40.08 -38.00 120.00   89
  3  ω    -49.00  -7.00   1.00    2.00    --  -40.08 125.00 -30.00   42
  4  ω    -65.00  30.00   1.00    2.00    --  -40.08  38.00 -60.00   95
  5  ω    -76.00 -51.00   1.00    2.00    --  -40.08 125.00 -30.00   25
  6  ω     86.00 111.00   1.00    2.00    --   40.08  57.00   0.00   25
  7  ω     12.00  68.00   1.00    2.00    --   40.08  57.00   0.00   56
  8  ω     52.00  96.00   1.00    2.00    --   40.08-125.00-150.00   44
  9  ω    124.00 178.00   1.00    3.00    --  112.00  45.00-150.00   54
 10  ω    139.00 178.00   1.00    3.00    --  112.00  45.00 120.00   39
 11  ω     53.00 138.00   1.00    3.00    --  112.00 -30.00 150.00   85
 12  ω     54.00  89.00   1.00    3.00    --  112.00 -77.00-120.00   35
 13  ω     74.00 100.00   1.00    3.00    --  112.00 178.00 -90.00   26
 14  ω     77.00 104.00   1.00    3.00    --  112.00-111.00 150.00   27
 15  ω    121.00 147.00   1.00    3.00    --  112.00  45.00 150.00   26
 16  ω     87.00 122.00   1.00    3.00    --  112.00  45.00 120.00   35
 17  ω     84.00 112.00   1.00    3.00    --  112.00  61.00-180.00   28
 18  ω    116.00 144.00   1.00    3.00    --  112.00 111.00-150.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1663908000
_diffrn_orient_matrix_UB_12      0.0332241000
_diffrn_orient_matrix_UB_13      -0.0341798000
_diffrn_orient_matrix_UB_21      -0.1373356000
_diffrn_orient_matrix_UB_22      -0.0969669000
_diffrn_orient_matrix_UB_23      -0.1733283000
_diffrn_orient_matrix_UB_31      -0.0161866000
_diffrn_orient_matrix_UB_32      0.1479657000
_diffrn_orient_matrix_UB_33      -0.0189300000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6581
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.487
_diffrn_reflns_theta_min         5.100
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0394
_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)+(0.0648P)²+0.0555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2328
_reflns_number_total             2857
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0733_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        686.77(8)
_cod_database_code               8105132
_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   0.918
_shelx_estimated_absorpt_t_min   0.881
_reflns_odcompleteness_completeness 69.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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:
 C10(H10A,H10B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.c :
 C12(H12), C15(H15)
;
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
O1 O 0.26180(14) 0.89380(11) 0.61705(11) 0.0687(3) Uani 1 1 d . . . . .
O2 O 0.62462(13) 0.72655(10) 0.92966(10) 0.0631(3) Uani 1 1 d . . . . .
N1 N 0.22943(15) 0.64959(12) 0.51991(12) 0.0562(3) Uani 1 1 d . . . . .
N2 N 0.45351(15) 0.81844(12) 0.78189(12) 0.0563(3) Uani 1 1 d . . . . .
N3 N 0.41981(14) 0.55814(11) 0.67794(11) 0.0531(3) Uani 1 1 d . . . . .
C1 C 0.0410(2) 0.34891(18) 0.27641(15) 0.0683(4) Uani 1 1 d . . . . .
H1 H -0.0012 0.4256 0.2608 0.082 Uiso 1 1 calc R . . . .
C2 C -0.0468(2) 0.1998(2) 0.15944(17) 0.0851(5) Uani 1 1 d . . . . .
H2 H -0.1485 0.1759 0.0646 0.102 Uiso 1 1 calc R . . . .
C3 C 0.0144(3) 0.0876(2) 0.1819(2) 0.0892(6) Uani 1 1 d . . . . .
H3 H -0.0463 -0.0130 0.1027 0.107 Uiso 1 1 calc R . . . .
C4 C 0.1634(3) 0.12125(19) 0.3189(2) 0.0849(5) Uani 1 1 d . . . . .
H4 H 0.2052 0.0440 0.3332 0.102 Uiso 1 1 calc R . . . .
C5 C 0.2528(2) 0.26881(16) 0.43661(18) 0.0690(4) Uani 1 1 d . . . . .
H5 H 0.3553 0.2916 0.5305 0.083 Uiso 1 1 calc R . . . .
C6 C 0.19101(17) 0.38337(14) 0.41604(14) 0.0551(3) Uani 1 1 d . . . . .
C7 C 0.28490(16) 0.53931(13) 0.54374(13) 0.0498(3) Uani 1 1 d . . . . .
C8 C 0.49416(17) 0.69758(14) 0.78949(13) 0.0516(3) Uani 1 1 d . . . . .
C9 C 0.32045(18) 0.78521(15) 0.64352(15) 0.0547(3) Uani 1 1 d . . . . .
C10 C 0.3547(2) 1.04671(16) 0.74137(19) 0.0701(4) Uani 1 1 d . . . . .
H10A H 0.3853 1.0356 0.8395 0.084 Uiso 1 1 calc R . . . .
H10B H 0.2698 1.0985 0.7269 0.084 Uiso 1 1 calc R . . . .
C11 C 0.5252(2) 1.14199(18) 0.7470(2) 0.0739(4) Uani 1 1 d . . . . .
C12 C 0.6599(3) 1.2194(2) 0.7483(3) 0.1089(7) Uani 1 1 d . . . . .
H12 H 0.7683 1.2817 0.7494 0.131 Uiso 1 1 calc R . . . .
C13 C 0.6787(2) 0.60103(16) 0.94380(15) 0.0637(4) Uani 1 1 d . . . . .
H13A H 0.7487 0.5858 0.8879 0.076 Uiso 1 1 calc R . . . .
H13B H 0.5672 0.5033 0.9011 0.076 Uiso 1 1 calc R . . . .
C14 C 0.79587(19) 0.64587(17) 1.10754(16) 0.0640(4) Uani 1 1 d . . . . .
C15 C 0.8877(2) 0.6802(2) 1.23930(18) 0.0789(5) Uani 1 1 d . . . . .
H15 H 0.9614 0.7077 1.3451 0.095 Uiso 1 1 calc R . . . .
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
C9 O1 C10 117.70(11) . .
C8 O2 C13 115.84(10) . .
C7 N1 C9 114.04(10) . .
C9 N2 C8 112.10(10) . .
C8 N3 C7 114.14(10) . .
C2 C1 H1 120.2 . .
C6 C1 H1 120.2 . .
C6 C1 C2 119.54(16) . .
C1 C2 H2 119.8 . .
C3 C2 C1 120.37(16) . .
C3 C2 H2 119.8 . .
C2 C3 H3 119.8 . .
C4 C3 C2 120.38(14) . .
C4 C3 H3 119.8 . .
C3 C4 H4 119.9 . .
C3 C4 C5 120.17(17) . .
C5 C4 H4 119.9 . .
C4 C5 H5 120.0 . .
C4 C5 C6 120.09(16) . .
C6 C5 H5 120.0 . .
C1 C6 C5 119.45(13) . .
C1 C6 C7 121.00(13) . .
C5 C6 C7 119.55(12) . .
N1 C7 N3 124.59(11) . .
N1 C7 C6 118.76(11) . .
N3 C7 C6 116.64(11) . .
N2 C8 O2 113.35(10) . .
N3 C8 O2 118.96(11) . .
N3 C8 N2 127.68(11) . .
O1 C9 N1 112.96(11) . .
N2 C9 O1 119.61(11) . .
N2 C9 N1 127.43(11) . .
O1 C10 H10A 109.4 . .
O1 C10 H10B 109.4 . .
O1 C10 C11 111.11(13) . .
H10A C10 H10B 108.0 . .
C11 C10 H10A 109.4 . .
C11 C10 H10B 109.4 . .
C12 C11 C10 178.3(2) . .
C11 C12 H12 180.0 . .
O2 C13 H13A 110.3 . .
O2 C13 H13B 110.3 . .
O2 C13 C14 106.86(11) . .
H13A C13 H13B 108.6 . .
C14 C13 H13A 110.3 . .
C14 C13 H13B 110.3 . .
C15 C14 C13 178.86(17) . .
C14 C15 H15 180.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.3368(15) .
O1 C10 1.4451(17) .
O2 C8 1.3372(14) .
O2 C13 1.4458(15) .
N1 C7 1.3315(15) .
N1 C9 1.3379(17) .
N2 C8 1.3317(16) .
N2 C9 1.3210(16) .
N3 C7 1.3428(15) .
N3 C8 1.3196(16) .
C1 H1 0.9400 .
C1 C2 1.394(2) .
C1 C6 1.3872(19) .
C2 H2 0.9400 .
C2 C3 1.371(3) .
C3 H3 0.9400 .
C3 C4 1.369(3) .
C4 H4 0.9400 .
C4 C5 1.385(2) .
C5 H5 0.9400 .
C5 C6 1.3919(19) .
C6 C7 1.4783(16) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 C11 1.448(2) .
C11 C12 1.167(3) .
C12 H12 0.9400 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 C14 1.4555(18) .
C14 C15 1.171(2) .
C15 H15 0.9400 .
