#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:29:16 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238570 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/77/7237735.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_7237735
loop_
_publ_author_name
'Yu, Yizhe'
'Yu, Changjiang'
'Wu, Qinghua'
'Wang, Hua'
'Jiao, Lijuan'
'Wong, Wai-Yeung'
'Hao, Erhong'
_publ_section_title
;
 Pure E/Z isomers of N-methylpyrrole-benzohydrazide-based BF2 complexes:
 remarkable aggregation-, crystallization-induced emission switching
 properties and application in sensing intracellular pH microenvironment
;
_journal_issue                   15
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4533
_journal_paper_doi               10.1039/C9TC00473D
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C14 H13 B F2 N3 O2'
_chemical_formula_sum            'C14 H13 B F2 N3 O2'
_chemical_formula_weight         304.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-01-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-02 deposited with the CCDC.	2019-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.598(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3108(5)
_cell_length_b                   6.7983(5)
_cell_length_c                   14.1226(11)
_cell_measurement_reflns_used    6520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      3.10
_cell_volume                     701.63(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16521
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.103
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6396
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'metallic whiteish white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       cube
_exptl_crystal_F_000             314
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0516P)²+0.2030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1128
_reflns_number_total             1347
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc00473d2.cif
_cod_data_source_block           1
_cod_database_code               7237735
_shelx_shelxl_version_number     2014/7
_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   0.993
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, H00L of C00K
 At 1.2 times of:
  H00D of C00D, H00E of C00E, H00F of C00F, H00G of C00G, H00H of C00H, H00A
  of C00A, H00C of C00C, H00I of C00I
2. Others
 Fixed Sof: H00B(0.5) H00J(0.5) H00K(0.5) H00L(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I)
3.b Idealised Me refined as rotating group:
 C00J(H00B,H00J,H00K)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
F001 F 0.00206(13) 0.58473(19) 0.30552(8) 0.0604(4) Uani 1 1 d . . . . .
O002 O 0.1799(2) 0.7500 0.19312(11) 0.0445(5) Uani 1 2 d S T P . .
O003 O 0.7560(2) 0.7500 -0.13242(11) 0.0502(5) Uani 1 2 d S T P . .
N004 N 0.2897(2) 0.7500 0.34732(12) 0.0351(5) Uani 1 2 d S T P . .
N005 N 0.4856(3) 0.7500 0.58896(13) 0.0369(5) Uani 1 2 d S T P . .
N006 N 0.4368(2) 0.7500 0.28644(12) 0.0367(5) Uani 1 2 d S T P . .
C007 C 0.3615(3) 0.7500 0.20168(15) 0.0339(5) Uani 1 2 d S T P . .
C008 C 0.4834(3) 0.7500 0.49064(15) 0.0322(5) Uani 1 2 d S T P . .
C009 C 0.4690(3) 0.7500 0.11662(15) 0.0343(5) Uani 1 2 d S T P . .
C00A C 0.3154(3) 0.7500 0.43846(15) 0.0348(5) Uani 1 2 d S T P . .
H00A H 0.2102 0.7500 0.4740 0.042 Uiso 1 2 calc RS T P . .
C00B C 0.6708(3) 0.7500 -0.04800(15) 0.0368(5) Uani 1 2 d S T P . .
C00C C 0.7605(3) 0.7500 0.04066(16) 0.0386(6) Uani 1 2 d S T P . .
H00C H 0.8877 0.7500 0.0451 0.046 Uiso 1 2 calc RS T P . .
C00D C 0.6593(3) 0.7500 0.12139(15) 0.0380(6) Uani 1 2 d S T P . .
H00D H 0.7193 0.7500 0.1803 0.046 Uiso 1 2 calc RS T P . .
C00E C 0.4813(3) 0.7500 -0.05344(16) 0.0407(6) Uani 1 2 d S T P . .
H00E H 0.4213 0.7500 -0.1124 0.049 Uiso 1 2 calc RS T P . .
C00F C 0.6642(3) 0.7500 0.46312(17) 0.0399(6) Uani 1 2 d S T P . .
H00F H 0.7044 0.7500 0.4012 0.048 Uiso 1 2 calc RS T P . .
C00G C 0.3818(3) 0.7500 0.02717(16) 0.0386(6) Uani 1 2 d S T P . .
H00G H 0.2547 0.7500 0.0225 0.046 Uiso 1 2 calc RS T P . .
C00H C 0.6587(4) 0.7500 0.62079(18) 0.0482(7) Uani 1 2 d S T P . .
H00H H 0.6965 0.7500 0.6842 0.058 Uiso 1 2 calc RS T P . .
C00I C 0.7734(3) 0.7500 0.54461(19) 0.0529(7) Uani 1 2 d S T P . .
H00I H 0.9007 0.7500 0.5476 0.063 Uiso 1 2 calc RS T P . .
C00J C 0.3282(4) 0.7500 0.65000(18) 0.0555(7) Uani 1 2 d S T P . .
H00B H 0.3648 0.7968 0.7118 0.083 Uiso 0.5 1 calc GR . . A -1
H00J H 0.2812 0.6187 0.6549 0.083 Uiso 0.5 1 calc GR . . A -1
H00K H 0.2349 0.8345 0.6235 0.083 Uiso 0.5 1 calc GR . . A -1
C00K C 0.9518(4) 0.7500 -0.1308(2) 0.0558(8) Uani 1 2 d S T P . .
H00L H 1.002(6) 0.870(7) -0.098(3) 0.084 Uiso 0.5 1 d R . . B -1
B00L B 0.1030(4) 0.7500 0.2883(2) 0.0424(7) Uani 1 2 d S T P . .
H00M H 0.983(4) 0.7500 -0.191(2) 0.049(8) Uiso 1 2 d S T P . .
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
C007 O002 B00L 108.86(17) .
C00B O003 C00K 118.0(2) .
N006 N004 B00L 110.12(17) .
C00A N004 N006 121.28(18) .
C00A N004 B00L 128.60(19) .
C008 N005 C00J 127.2(2) .
C00H N005 C008 108.8(2) .
C00H N005 C00J 124.0(2) .
C007 N006 N004 104.64(17) .
O002 C007 C009 119.10(19) .
N006 C007 O002 118.6(2) .
N006 C007 C009 122.3(2) .
N005 C008 C00A 120.5(2) .
C00F C008 N005 107.17(19) .
C00F C008 C00A 132.4(2) .
C00D C009 C007 121.54(19) .
C00D C009 C00G 118.3(2) .
C00G C009 C007 120.2(2) .
N004 C00A C008 128.1(2) .
N004 C00A H00A 115.9 .
C008 C00A H00A 115.9 .
O003 C00B C00C 124.8(2) .
O003 C00B C00E 115.7(2) .
C00E C00B C00C 119.6(2) .
C00B C00C H00C 120.3 .
C00D C00C C00B 119.5(2) .
C00D C00C H00C 120.3 .
C009 C00D H00D 119.3 .
C00C C00D C009 121.3(2) .
C00C C00D H00D 119.3 .
C00B C00E H00E 119.7 .
C00G C00E C00B 120.5(2) .
C00G C00E H00E 119.7 .
C008 C00F H00F 126.3 .
C00I C00F C008 107.4(2) .
C00I C00F H00F 126.3 .
C009 C00G H00G 119.6 .
C00E C00G C009 120.8(2) .
C00E C00G H00G 119.6 .
N005 C00H H00H 125.4 .
N005 C00H C00I 109.2(2) .
C00I C00H H00H 125.4 .
C00F C00I C00H 107.4(2) .
C00F C00I H00I 126.3 .
C00H C00I H00I 126.3 .
N005 C00J H00B 109.5 .
N005 C00J H00J 109.5 .
N005 C00J H00K 109.5 .
H00B C00J H00J 109.5 .
H00B C00J H00K 109.5 .
H00J C00J H00K 109.5 .
O003 C00K H00L 111(3) .
O003 C00K H00M 105.7(17) .
H00L C00K H00M 110(3) .
F001 B00L F001 110.2(2) 4_575
F001 B00L O002 112.59(14) .
F001 B00L O002 112.59(14) 4_575
F001 B00L N004 111.58(13) 4_575
F001 B00L N004 111.58(13) .
O002 B00L N004 97.79(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F001 B00L 1.3698(19) .
O002 C007 1.329(3) .
O002 B00L 1.471(3) .
O003 C00B 1.361(3) .
O003 C00K 1.431(3) .
N004 N006 1.396(2) .
N004 C00A 1.296(3) .
N004 B00L 1.580(3) .
N005 C008 1.388(3) .
N005 C00H 1.331(3) .
N005 C00J 1.457(3) .
N006 C007 1.304(3) .
C007 C009 1.454(3) .
C008 C00A 1.415(3) .
C008 C00F 1.388(3) .
C009 C00D 1.391(3) .
C009 C00G 1.399(3) .
C00A H00A 0.9300 .
C00B C00C 1.397(3) .
C00B C00E 1.385(3) .
C00C H00C 0.9300 .
C00C C00D 1.376(3) .
C00D H00D 0.9300 .
C00E H00E 0.9300 .
C00E C00G 1.368(3) .
C00F H00F 0.9300 .
C00F C00I 1.383(4) .
C00G H00G 0.9300 .
C00H H00H 0.9300 .
C00H C00I 1.383(4) .
C00I H00I 0.9300 .
C00J H00B 0.9600 .
C00J H00J 0.9600 .
C00J H00K 0.9600 .
C00K H00L 1.00(5) .
C00K H00M 0.88(3) .
B00L F001 1.3698(19) 4_575
