#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:05:29 +0100 (Sat 23 de Nov de 2019) $
#$Revision: 234570 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/51/7125171.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_7125171
loop_
_publ_author_name
'Tang, Baolei'
'Zhang, Houyu'
'Ye, Kaiqi'
'Zhang, Hongyu'
'Wang, Yue'
_publ_section_title
;
 Highly efficient blue solid emitters and tautomerization-induced ON/OFF
 fluorescence switching based on structurally simple
 3(5)-phenol-1H-pyrazoles.
;
_journal_issue                   89
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13128
_journal_page_last               13131
_journal_paper_doi               10.1039/c6cc07300j
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C10 H10 N2 O'
_chemical_formula_sum            'C10 H10 N2 O'
_chemical_formula_weight         174.20
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_update_record
;
2016-05-14 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7690(16)
_cell_length_b                   11.243(2)
_cell_length_c                   10.244(2)
_cell_measurement_reflns_used    7980
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.475
_cell_measurement_theta_min      3.215
_cell_volume                     880.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω 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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8279
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0510
_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)+(0.0684P)²+0.3009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                1508
_reflns_number_total             1999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc07300j2.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7125171
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
_atom_site_refinement_flags
C9 C 0.1651(3) -0.02111(19) 0.8818(2) 0.0475(5) Uani 1 1 d .
N1 N 0.4093(2) 0.19814(13) 1.11729(15) 0.0430(4) Uani 1 1 d .
C4 C 0.2655(2) 0.02156(15) 0.99935(17) 0.0345(4) Uani 1 1 d .
C3 C 0.3153(2) 0.14737(15) 1.00879(16) 0.0341(4) Uani 1 1 d .
C6 C 0.2604(3) -0.17765(16) 1.0880(2) 0.0436(5) Uani 1 1 d .
C5 C 0.3127(2) -0.05897(15) 1.10321(17) 0.0365(4) Uani 1 1 d .
N2 N 0.4387(2) 0.31550(13) 1.10274(16) 0.0479(4) Uani 1 1 d .
C7 C 0.1625(3) -0.21888(17) 0.9703(2) 0.0482(5) Uani 1 1 d .
C1 C 0.3604(3) 0.33920(17) 0.9800(2) 0.0462(5) Uani 1 1 d .
C8 C 0.1155(3) -0.1391(2) 0.8675(2) 0.0544(6) Uani 1 1 d .
C2 C 0.2826(3) 0.23858(17) 0.9165(2) 0.0456(5) Uani 1 1 d .
C10 C 0.1101(4) -0.3482(2) 0.9552(4) 0.0688(8) Uani 1 1 d .
O1 O 0.41073(19) -0.01897(11) 1.21867(12) 0.0496(4) Uani 1 1 d .
H9 H 0.4298 -0.0740 1.2717 0.074 Uiso 1 1 calc R
H10 H 0.451(3) 0.163(2) 1.187(2) 0.050(6) Uiso 1 1 d .
H3 H 0.130(3) 0.034(2) 0.812(2) 0.063(7) Uiso 1 1 d .
H8 H 0.295(3) -0.2308(19) 1.166(2) 0.051(6) Uiso 1 1 d .
H2 H 0.220(3) 0.234(2) 0.822(3) 0.064(7) Uiso 1 1 d .
H1 H 0.365(3) 0.4222(19) 0.948(2) 0.050(5) Uiso 1 1 d .
H4 H 0.047(3) -0.164(2) 0.781(2) 0.068(7) Uiso 1 1 d .
H6 H 0.148(4) -0.387(3) 0.875(4) 0.124(12) Uiso 1 1 d .
H5 H -0.015(4) -0.357(3) 0.942(3) 0.101(10) Uiso 1 1 d .
H7 H 0.158(5) -0.392(3) 1.031(3) 0.106(12) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C9 0.0467(11) 0.0487(11) 0.0434(11) -0.0044(9) -0.0019(9) 0.0022(9)
N1 0.0677(11) 0.0276(7) 0.0303(8) 0.0019(6) -0.0005(7) -0.0015(7)
C4 0.0356(8) 0.0326(8) 0.0353(9) -0.0055(7) 0.0059(7) 0.0026(6)
C3 0.0367(9) 0.0343(9) 0.0312(8) 0.0001(6) 0.0055(7) 0.0044(7)
C6 0.0490(11) 0.0331(9) 0.0504(11) -0.0032(8) 0.0133(9) -0.0002(8)
C5 0.0417(9) 0.0328(9) 0.0352(9) -0.0044(7) 0.0073(7) 0.0018(7)
N2 0.0723(11) 0.0279(8) 0.0425(9) -0.0006(6) 0.0078(8) -0.0034(7)
C7 0.0429(10) 0.0396(10) 0.0640(13) -0.0167(9) 0.0150(10) -0.0065(8)
C1 0.0591(12) 0.0328(9) 0.0457(10) 0.0084(8) 0.0067(9) 0.0057(8)
C8 0.0478(12) 0.0564(12) 0.0552(13) -0.0202(10) -0.0011(10) -0.0072(9)
C2 0.0514(11) 0.0435(10) 0.0386(10) 0.0070(8) -0.0009(8) 0.0061(8)
C10 0.0686(16) 0.0460(13) 0.094(2) -0.0265(14) 0.0199(16) -0.0177(11)
O1 0.0806(10) 0.0292(6) 0.0339(7) 0.0023(5) -0.0040(7) -0.0017(6)
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
C8 C9 C4 121.5(2)
C3 N1 N2 113.64(15)
C5 C4 C9 117.74(17)
C5 C4 C3 123.02(16)
C9 C4 C3 119.24(17)
N1 C3 C2 104.91(16)
N1 C3 C4 124.27(15)
C2 C3 C4 130.83(17)
C7 C6 C5 121.38(19)
O1 C5 C6 121.24(17)
O1 C5 C4 118.57(15)
C6 C5 C4 120.19(17)
C1 N2 N1 104.05(15)
C8 C7 C6 118.44(18)
C8 C7 C10 121.1(2)
C6 C7 C10 120.5(2)
N2 C1 C2 111.72(17)
C9 C8 C7 120.72(19)
C3 C2 C1 105.68(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 C8 1.382(3)
C9 C4 1.399(3)
N1 C3 1.345(2)
N1 N2 1.352(2)
C4 C5 1.396(2)
C4 C3 1.465(2)
C3 C2 1.388(2)
C6 C7 1.387(3)
C6 C5 1.395(3)
C5 O1 1.365(2)
N2 C1 1.324(3)
C7 C8 1.382(3)
C7 C10 1.511(3)
C1 C2 1.389(3)
