# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronicacid_110Phenanthroline
_database_code_depnum_ccdc_archive 'CCDC 2260224'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 B N3 O3'
_chemical_formula_weight         355.15

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8278(3)
_cell_length_b                   17.1899(6)
_cell_length_c                   26.2562(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1727.64(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5189
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.94

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5434
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39424
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_av_R_equivalents  0.1738
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.952
_diffrn_reflns_theta_max         26.649
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3595
_reflns_number_gt                2604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0648P)²+0.9970P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 860 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3595
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.1939(8) 0.33937(16) 0.33620(10) 0.0273(7) Uani 1 1 d . . . . .
H1A H 0.158201 0.306057 0.314459 0.07(2) Uiso 1 1 calc R . . . .
O2 O 0.4237(8) 0.22972(16) 0.38166(10) 0.0266(7) Uani 1 1 d . . . . .
H2A H 0.410080 0.209778 0.353361 0.09(2) Uiso 1 1 calc R . . . .
O3 O 1.020(8) 0.6810(4) 0.5266(3) 0.375(12) Uani 1 1 d . . . . .
N1 N 0.0756(9) 0.25146(17) 0.24831(11) 0.0211(7) Uani 1 1 d . . . . .
N2 N 0.4139(9) 0.13115(18) 0.29949(11) 0.0206(7) Uani 1 1 d . . . . .
N3 N 0.6397(12) 0.5369(2) 0.59118(14) 0.0435(11) Uani 1 1 d . . . . .
C1 C -0.0837(11) 0.3079(2) 0.22291(14) 0.0223(9) Uani 1 1 d . . . . .
H1 H -0.136009 0.353446 0.240392 0.027 Uiso 1 1 calc R U . . .
C2 C -0.1784(11) 0.3033(2) 0.17146(14) 0.0245(9) Uani 1 1 d . . . . .
H2 H -0.286635 0.344906 0.155173 0.029 Uiso 1 1 calc R U . . .
C3 C -0.1072(12) 0.2363(2) 0.14612(14) 0.0259(9) Uani 1 1 d . . . . .
H3 H -0.168656 0.231346 0.112002 0.031 Uiso 1 1 calc R U . . .
C4 C 0.0585(11) 0.1746(2) 0.17120(14) 0.0216(9) Uani 1 1 d . . . . .
C5 C 0.1511(10) 0.1844(2) 0.22319(13) 0.0199(8) Uani 1 1 d . . . . .
C6 C 0.1401(11) 0.1027(2) 0.14612(14) 0.0249(9) Uani 1 1 d . . . . .
H6 H 0.081145 0.096570 0.111994 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2999(11) 0.0440(2) 0.17076(14) 0.0246(9) Uani 1 1 d . . . . .
H7 H 0.346129 -0.002240 0.153688 0.030 Uiso 1 1 calc R U . . .
C8 C 0.5707(11) -0.0079(2) 0.24909(16) 0.0249(9) Uani 1 1 d . . . . .
H8 H 0.625497 -0.054059 0.232443 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6568(11) 0.0021(2) 0.29939(15) 0.0252(9) Uani 1 1 d . . . . .
H9 H 0.767658 -0.037300 0.317525 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5746(11) 0.0723(2) 0.32259(15) 0.0225(9) Uani 1 1 d . . . . .
H10 H 0.636147 0.078673 0.356606 0.027 Uiso 1 1 calc R U . . .
C11 C 0.3231(10) 0.1216(2) 0.24951(14) 0.0187(8) Uani 1 1 d . . . . .
C12 C 0.3992(10) 0.0523(2) 0.22302(14) 0.0211(8) Uani 1 1 d . . . . .
C13 C 0.3886(11) 0.3581(2) 0.42707(13) 0.0199(8) Uani 1 1 d . . . . .
C14 C 0.2831(11) 0.4354(2) 0.42880(14) 0.0221(9) Uani 1 1 d . . . . .
H14 H 0.169271 0.456483 0.400737 0.026 Uiso 1 1 calc R U . . .
C15 C 0.3418(11) 0.4818(2) 0.47082(14) 0.0232(9) Uani 1 1 d . . . . .
H15 H 0.274468 0.533760 0.470770 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5053(10) 0.4490(2) 0.51375(14) 0.0226(9) Uani 1 1 d . . . . .
C17 C 0.6066(11) 0.3721(2) 0.51388(13) 0.0224(9) Uani 1 1 d . . . . .
H17 H 0.711387 0.350410 0.542511 0.027 Uiso 1 1 calc R U . . .
C18 C 0.5497(11) 0.3274(2) 0.47057(13) 0.0220(9) Uani 1 1 d . . . . .
H18 H 0.620487 0.275649 0.470448 0.026 Uiso 1 1 calc R U . . .
C19 C 0.5757(12) 0.4974(2) 0.55723(15) 0.0281(10) Uani 1 1 d . . . . .
C20 C 1.046(13) 0.7595(14) 0.5024(7) 0.246(11) Uani 1 1 d . . . . .
H20A H 0.815828 0.780033 0.496955 0.370 Uiso 1 1 calc R U . . .
H20B H 1.164560 0.755054 0.470259 0.370 Uiso 1 1 calc R U . . .
H20C H 1.174663 0.793827 0.524281 0.370 Uiso 1 1 calc R U . . .
B1 B 0.3313(12) 0.3053(3) 0.37868(16) 0.0210(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.365(5) . ?
O1 H1A 0.8200 . ?
O2 B1 1.349(5) . ?
O2 H2A 0.8200 . ?
O3 C20 1.50(2) . ?
N1 C1 1.325(5) . ?
N1 C5 1.360(5) . ?
N2 C10 1.330(5) . ?
N2 C11 1.367(5) . ?
N3 C19 1.147(5) . ?
C1 C2 1.401(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.421(5) . ?
C4 C6 1.434(5) . ?
C5 C11 1.440(5) . ?
C6 C7 1.346(5) . ?
C6 H6 0.9300 . ?
C7 C12 1.431(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(6) . ?
C8 C12 1.403(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.410(5) . ?
C13 C14 1.388(5) . ?
C13 C18 1.401(5) . ?
C13 B1 1.577(6) . ?
C14 C15 1.380(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.407(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(5) . ?
C16 C19 1.439(5) . ?
C17 C18 1.389(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 C20 1.946(9) 4_466 ?
C20 C20 1.946(9) 4_566 ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
_geom_angle_publ_flag
B1 O1 H1A 109.5 . . ?
B1 O2 H2A 109.5 . . ?
C1 N1 C5 118.3(3) . . ?
C10 N2 C11 117.7(3) . . ?
N1 C1 C2 124.3(4) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C3 C2 C1 117.9(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.4(4) . . ?
C3 C4 C6 122.3(3) . . ?
C5 C4 C6 119.3(4) . . ?
N1 C5 C4 120.9(3) . . ?
N1 C5 C11 120.0(3) . . ?
C4 C5 C11 119.1(3) . . ?
C7 C6 C4 121.6(4) . . ?
C7 C6 H6 119.2 . . ?
C4 C6 H6 119.2 . . ?
C6 C7 C12 120.5(4) . . ?
C6 C7 H7 119.7 . . ?
C12 C7 H7 119.7 . . ?
C9 C8 C12 119.3(4) . . ?
C9 C8 H8 120.3 . . ?
C12 C8 H8 120.3 . . ?
C8 C9 C10 118.5(4) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N2 C10 C9 124.5(4) . . ?
N2 C10 H10 117.8 . . ?
C9 C10 H10 117.8 . . ?
N2 C11 C12 121.5(3) . . ?
N2 C11 C5 119.1(3) . . ?
C12 C11 C5 119.4(3) . . ?
C8 C12 C11 118.6(3) . . ?
C8 C12 C7 121.3(4) . . ?
C11 C12 C7 120.1(4) . . ?
C14 C13 C18 117.5(3) . . ?
C14 C13 B1 122.5(3) . . ?
C18 C13 B1 120.0(3) . . ?
C15 C14 C13 122.1(4) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 118.7(4) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 C19 120.1(4) . . ?
C15 C16 C19 119.1(4) . . ?
C16 C17 C18 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 121.8(4) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
N3 C19 C16 178.1(5) . . ?
O3 C20 C20 79(2) . 4_466 ?
O3 C20 C20 87(3) . 4_566 ?
C20 C20 C20 159(3) 4_466 4_566 ?
O3 C20 H20A 109.5 . . ?
C20 C20 H20A 31.7 4_466 . ?
C20 C20 H20A 162.9 4_566 . ?
O3 C20 H20B 109.5 . . ?
C20 C20 H20B 113.3 4_466 . ?
C20 C20 H20B 57.7 4_566 . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
C20 C20 H20C 130.2 4_466 . ?
C20 C20 H20C 68.7 4_566 . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 B1 O1 124.2(4) . . ?
O2 B1 C13 118.1(3) . . ?
O1 B1 C13 117.7(4) . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.083

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronicacid_17Phenanthroline
_database_code_depnum_ccdc_archive 'CCDC 2260225'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 B N3 O2'
_chemical_formula_weight         327.14

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1497(3)
_cell_length_b                   8.7492(4)
_cell_length_c                   13.6709(6)
_cell_angle_alpha                97.158(4)
_cell_angle_beta                 96.960(3)
_cell_angle_gamma                95.413(4)
_cell_volume                     837.04(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2294
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      23.22

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5724
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14761
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.361
_diffrn_reflns_theta_max         26.582
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3431
_reflns_number_gt                1761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+0.1412P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3431
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8320(2) 0.4691(2) 0.89776(12) 0.0690(6) Uani 1 1 d . . . . .
H1 H 0.770409 0.467982 0.842981 0.103 Uiso 1 1 calc R U . . .
O2 O 0.8188(3) 0.3553(2) 1.04152(13) 0.0789(6) Uani 1 1 d . . . . .
H2A H 0.917497 0.413848 1.056630 0.118 Uiso 1 1 calc R U . . .
N1 N 0.7506(3) 0.5225(3) 0.70617(15) 0.0647(6) Uani 1 1 d . . . . .
N2 N 0.7433(3) 0.4312(3) 0.35209(16) 0.0704(7) Uani 1 1 d . . . . .
N3 N -0.1975(4) 0.0396(3) 0.8193(2) 0.0871(8) Uani 1 1 d . . . . .
C1 C 0.5216(4) 0.3069(3) 0.92121(18) 0.0559(6) Uani 1 1 d . . . . .
C2 C 0.4115(4) 0.3334(3) 0.83625(19) 0.0625(7) Uani 1 1 d . . . . .
H2 H 0.464131 0.398046 0.795295 0.075 Uiso 1 1 calc R U . . .
C3 C 0.2255(4) 0.2676(3) 0.80954(19) 0.0649(7) Uani 1 1 d . . . . .
H3 H 0.155239 0.288483 0.751859 0.078 Uiso 1 1 calc R U . . .
C4 C 0.1452(4) 0.1709(3) 0.86892(19) 0.0584(7) Uani 1 1 d . . . . .
C5 C 0.2512(4) 0.1424(3) 0.9539(2) 0.0755(8) Uani 1 1 d . . . . .
H5 H 0.198361 0.076894 0.994307 0.091 Uiso 1 1 calc R U . . .
C6 C 0.4345(4) 0.2098(3) 0.9796(2) 0.0735(8) Uani 1 1 d . . . . .
H6 H 0.502981 0.189940 1.038086 0.088 Uiso 1 1 calc R U . . .
C7 C -0.0465(4) 0.0986(3) 0.8414(2) 0.0659(7) Uani 1 1 d . . . . .
C8 C 0.7263(5) 0.3296(5) 0.2713(2) 0.0864(10) Uani 1 1 d . . . . .
H8 H 0.735803 0.367297 0.211244 0.104 Uiso 1 1 calc R U . . .
C9 C 0.6957(5) 0.1731(4) 0.2692(3) 0.0895(10) Uani 1 1 d . . . . .
H9 H 0.681829 0.107865 0.209076 0.107 Uiso 1 1 calc R U . . .
C10 C 0.6856(4) 0.1134(4) 0.3552(3) 0.0824(9) Uani 1 1 d . . . . .
H10 H 0.665848 0.006801 0.355169 0.099 Uiso 1 1 calc R U . . .
C11 C 0.7056(4) 0.2154(3) 0.4444(2) 0.0616(7) Uani 1 1 d . . . . .
C12 C 0.7320(3) 0.3740(3) 0.43822(18) 0.0534(6) Uani 1 1 d . . . . .
C13 C 0.7484(3) 0.4827(3) 0.52807(18) 0.0506(6) Uani 1 1 d . . . . .
C14 C 0.7760(4) 0.6421(3) 0.5296(2) 0.0655(7) Uani 1 1 d . . . . .
H14 H 0.784493 0.683742 0.470745 0.079 Uiso 1 1 calc R U . . .
C15 C 0.7905(4) 0.7371(3) 0.6173(2) 0.0718(8) Uani 1 1 d . . . . .
H15 H 0.809840 0.844124 0.619298 0.086 Uiso 1 1 calc R U . . .
C16 C 0.7761(4) 0.6725(4) 0.7027(2) 0.0724(8) Uani 1 1 d . . . . .
H16 H 0.785015 0.738990 0.762149 0.087 Uiso 1 1 calc R U . . .
C17 C 0.7374(3) 0.4259(3) 0.61879(18) 0.0548(6) Uani 1 1 d . . . . .
C18 C 0.7111(4) 0.2652(3) 0.6214(2) 0.0718(8) Uani 1 1 d . . . . .
H18 H 0.703827 0.228034 0.681786 0.086 Uiso 1 1 calc R U . . .
C19 C 0.6963(4) 0.1656(3) 0.5377(2) 0.0773(8) Uani 1 1 d . . . . .
H19 H 0.679359 0.059818 0.541347 0.093 Uiso 1 1 calc R U . . .
B1 B 0.7317(4) 0.3812(4) 0.9531(2) 0.0585(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.360(3) . ?
O1 H1 0.8200 . ?
O2 B1 1.346(3) . ?
O2 H2A 0.8200 . ?
N1 C16 1.315(3) . ?
N1 C17 1.362(3) . ?
N2 C8 1.314(4) . ?
N2 C12 1.344(3) . ?
N3 C7 1.140(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.392(4) . ?
C1 B1 1.567(4) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C4 C7 1.440(4) . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.362(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.351(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.402(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(4) . ?
C11 C19 1.406(4) . ?
C12 C13 1.442(3) . ?
C13 C14 1.387(4) . ?
C13 C17 1.400(3) . ?
C14 C15 1.358(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.406(4) . ?
C18 C19 1.336(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
_geom_angle_publ_flag
B1 O1 H1 109.5 . . ?
B1 O2 H2A 109.5 . . ?
C16 N1 C17 117.5(2) . . ?
C8 N2 C12 116.6(3) . . ?
C2 C1 C6 116.0(2) . . ?
C2 C1 B1 123.4(2) . . ?
C6 C1 B1 120.6(2) . . ?
C1 C2 C3 122.6(2) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 C7 120.4(2) . . ?
C3 C4 C7 120.4(2) . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 122.3(3) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
N3 C7 C4 179.1(3) . . ?
N2 C8 C9 124.7(3) . . ?
N2 C8 H8 117.6 . . ?
C9 C8 H8 117.6 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 118.6(3) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 117.4(3) . . ?
C12 C11 C19 119.4(3) . . ?
C10 C11 C19 123.3(3) . . ?
N2 C12 C11 123.1(2) . . ?
N2 C12 C13 117.9(2) . . ?
C11 C12 C13 119.0(2) . . ?
C14 C13 C17 117.8(2) . . ?
C14 C13 C12 123.2(2) . . ?
C17 C13 C12 118.9(2) . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 118.8(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N1 C16 C15 124.2(3) . . ?
N1 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
N1 C17 C13 121.8(2) . . ?
N1 C17 C18 118.1(2) . . ?
C13 C17 C18 120.0(2) . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C11 122.1(3) . . ?
C18 C19 H19 118.9 . . ?
C11 C19 H19 118.9 . . ?
O2 B1 O1 117.9(2) . . ?
O2 B1 C1 117.4(2) . . ?
O1 B1 C1 124.7(2) . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.035

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronicacid_Acridine
_database_code_depnum_ccdc_archive 'CCDC 2260227'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 B N2 O2'
_chemical_formula_weight         326.15

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0840(8)
_cell_length_b                   7.3311(5)
_cell_length_c                   21.0913(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.007(6)
_cell_angle_gamma                90
_cell_volume                     1692.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2174
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      23.72

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11943
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3443
_reflns_number_gt                1910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+0.2328P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0109(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3443
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1528
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.41552(13) 0.8467(2) 0.53079(8) 0.0625(5) Uani 1 1 d . . . . .
H1 H 0.359489 0.795704 0.544938 0.094 Uiso 1 1 calc R U . . .
O2 O 0.62896(13) 0.8563(2) 0.54921(9) 0.0668(5) Uani 1 1 d . . . . .
H2A H 0.612681 0.951306 0.529144 0.100 Uiso 1 1 calc R U . . .
N1 N 0.18901(15) 0.7771(2) 0.55596(9) 0.0468(5) Uani 1 1 d . . . . .
N2 N 0.5771(2) -0.0485(3) 0.72519(13) 0.0912(8) Uani 1 1 d . . . . .
C1 C 0.15859(19) 0.8364(3) 0.61193(11) 0.0483(6) Uani 1 1 d . . . . .
C2 C 0.2532(2) 0.8792(3) 0.66320(13) 0.0655(7) Uani 1 1 d . . . . .
H2 H 0.334243 0.858996 0.658610 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2265(3) 0.9495(4) 0.71891(15) 0.0848(9) Uani 1 1 d . . . . .
H3 H 0.289634 0.979987 0.751614 0.102 Uiso 1 1 calc R U . . .
C4 C 0.1051(4) 0.9767(4) 0.72794(15) 0.0908(10) Uani 1 1 d . . . . .
H4 H 0.088684 1.024851 0.766479 0.109 Uiso 1 1 calc R U . . .
C5 C 0.0119(3) 0.9336(4) 0.68115(14) 0.0738(8) Uani 1 1 d . . . . .
H5 H -0.068172 0.950265 0.688123 0.089 Uiso 1 1 calc R U . . .
C6 C 0.0347(2) 0.8626(3) 0.62106(12) 0.0517(6) Uani 1 1 d . . . . .
C7 C -0.05636(19) 0.8244(3) 0.57019(13) 0.0545(6) Uani 1 1 d . . . . .
H7 H -0.137773 0.839399 0.574968 0.065 Uiso 1 1 calc R U . . .
C8 C -0.02760(18) 0.7641(3) 0.51223(12) 0.0470(6) Uani 1 1 d . . . . .
C9 C -0.1173(2) 0.7262(3) 0.45823(14) 0.0646(7) Uani 1 1 d . . . . .
H9 H -0.199608 0.740005 0.461232 0.077 Uiso 1 1 calc R U . . .
C10 C -0.0842(3) 0.6703(3) 0.40258(15) 0.0747(8) Uani 1 1 d . . . . .
H10 H -0.143886 0.645083 0.367555 0.090 Uiso 1 1 calc R U . . .
C11 C 0.0400(3) 0.6498(3) 0.39695(13) 0.0726(8) Uani 1 1 d . . . . .
H11 H 0.061111 0.611850 0.358066 0.087 Uiso 1 1 calc R U . . .
C12 C 0.1294(2) 0.6844(3) 0.44716(12) 0.0592(6) Uani 1 1 d . . . . .
H12 H 0.210935 0.669748 0.442587 0.071 Uiso 1 1 calc R U . . .
C13 C 0.09839(19) 0.7430(3) 0.50669(11) 0.0451(5) Uani 1 1 d . . . . .
C14 C 0.53488(18) 0.5860(3) 0.59523(11) 0.0475(6) Uani 1 1 d . . . . .
C15 C 0.44278(19) 0.4554(3) 0.58639(11) 0.0564(6) Uani 1 1 d . . . . .
H15 H 0.371528 0.479984 0.558085 0.068 Uiso 1 1 calc R U . . .
C16 C 0.4538(2) 0.2905(3) 0.61828(12) 0.0617(7) Uani 1 1 d . . . . .
H16 H 0.391349 0.204733 0.610964 0.074 Uiso 1 1 calc R U . . .
C17 C 0.55852(19) 0.2540(3) 0.66120(11) 0.0504(6) Uani 1 1 d . . . . .
C18 C 0.6518(2) 0.3809(3) 0.67162(12) 0.0589(6) Uani 1 1 d . . . . .
H18 H 0.722247 0.356875 0.700605 0.071 Uiso 1 1 calc R U . . .
C19 C 0.63906(19) 0.5435(3) 0.63850(12) 0.0578(7) Uani 1 1 d . . . . .
H19 H 0.702418 0.627858 0.645319 0.069 Uiso 1 1 calc R U . . .
C20 C 0.5693(2) 0.0846(4) 0.69664(13) 0.0639(7) Uani 1 1 d . . . . .
B1 B 0.5237(2) 0.7703(4) 0.55709(14) 0.0510(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.360(3) . ?
O1 H1 0.8200 . ?
O2 B1 1.360(3) . ?
O2 H2A 0.8200 . ?
N1 C1 1.349(3) . ?
N1 C13 1.351(3) . ?
N2 C20 1.143(3) . ?
C1 C2 1.419(3) . ?
C1 C6 1.429(3) . ?
C2 C3 1.358(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.350(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.429(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(3) . ?
C8 C13 1.428(3) . ?
C9 C10 1.347(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.408(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.419(3) . ?
C12 H12 0.9300 . ?
C14 C19 1.390(3) . ?
C14 C15 1.391(3) . ?
C14 B1 1.568(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(3) . ?
C17 C20 1.445(3) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
_geom_angle_publ_flag
B1 O1 H1 109.5 . . ?
B1 O2 H2A 109.5 . . ?
C1 N1 C13 118.37(18) . . ?
N1 C1 C2 118.8(2) . . ?
N1 C1 C6 122.6(2) . . ?
C2 C1 C6 118.6(2) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 123.6(2) . . ?
C7 C6 C1 117.9(2) . . ?
C5 C6 C1 118.4(2) . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 122.9(2) . . ?
C7 C8 C13 118.1(2) . . ?
C9 C8 C13 119.0(2) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N1 C13 C12 118.9(2) . . ?
N1 C13 C8 122.4(2) . . ?
C12 C13 C8 118.7(2) . . ?
C19 C14 C15 116.8(2) . . ?
C19 C14 B1 121.39(19) . . ?
C15 C14 B1 121.8(2) . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 C20 119.9(2) . . ?
C18 C17 C20 119.8(2) . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C14 122.4(2) . . ?
C18 C19 H19 118.8 . . ?
C14 C19 H19 118.8 . . ?
N2 C20 C17 179.2(3) . . ?
O2 B1 O1 118.5(2) . . ?
O2 B1 C14 117.5(2) . . ?
O1 B1 C14 123.9(2) . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.038

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronicacid_47Phenanthroline
_database_code_depnum_ccdc_archive 'CCDC 2260226'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 B N3 O2'
_chemical_formula_weight         327.14

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.8728(7)
_cell_length_b                   3.8786(2)
_cell_length_c                   15.4857(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.182(5)
_cell_angle_gamma                90
_cell_volume                     808.40(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2754
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.63

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4937
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8701
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         26.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3256
_reflns_number_gt                2475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0776P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 810 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3256
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1394
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.21794(18) 0.4539(9) 0.15805(18) 0.0548(8) Uani 1 1 d . . . . .
H1 H 0.275697 0.388636 0.177586 0.082 Uiso 1 1 calc R U . . .
O2 O 0.26888(19) 0.4887(10) 0.32328(18) 0.0599(9) Uani 1 1 d . . . . .
H2A H 0.244890 0.529355 0.361073 0.090 Uiso 1 1 calc R U . . .
N1 N 0.3941(2) 0.1142(9) 0.1883(2) 0.0484(9) Uani 1 1 d . . . . .
N2 N 0.7572(2) 0.0050(9) 0.5027(2) 0.0505(8) Uani 1 1 d . . . . .
N3 N -0.2649(3) 1.2561(11) 0.1302(3) 0.0603(10) Uani 1 1 d . . . . .
C1 C 0.0949(3) 0.7123(9) 0.2098(3) 0.0385(8) Uani 1 1 d . . . . .
C2 C 0.0210(3) 0.7192(10) 0.1160(3) 0.0421(9) Uani 1 1 d . . . . .
H2 H 0.035257 0.630980 0.067410 0.050 Uiso 1 1 calc R U . . .
C3 C -0.0728(3) 0.8531(10) 0.0932(3) 0.0433(9) Uani 1 1 d . . . . .
H3 H -0.120764 0.853433 0.030349 0.052 Uiso 1 1 calc R U . . .
C4 C -0.0941(3) 0.9864(10) 0.1654(2) 0.0391(8) Uani 1 1 d . . . . .
C5 C -0.0225(3) 0.9854(11) 0.2592(3) 0.0429(9) Uani 1 1 d . . . . .
H5 H -0.037021 1.073977 0.307581 0.051 Uiso 1 1 calc R U . . .
C6 C 0.0706(3) 0.8520(10) 0.2800(3) 0.0439(9) Uani 1 1 d . . . . .
H6 H 0.118467 0.855560 0.342856 0.053 Uiso 1 1 calc R U . . .
C7 C -0.1902(3) 1.1329(10) 0.1445(3) 0.0436(9) Uani 1 1 d . . . . .
C8 C 0.5485(3) -0.1888(10) 0.1589(3) 0.0424(9) Uani 1 1 d . . . . .
H8 H 0.599646 -0.289683 0.148369 0.051 Uiso 1 1 calc R U . . .
C9 C 0.4570(3) -0.1519(12) 0.0855(3) 0.0511(10) Uani 1 1 d . . . . .
H9 H 0.444567 -0.228724 0.024529 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3826(3) 0.0031(12) 0.1036(3) 0.0524(11) Uani 1 1 d . . . . .
H10 H 0.320628 0.030596 0.052689 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4855(3) 0.0739(9) 0.2623(3) 0.0397(9) Uani 1 1 d . . . . .
C12 C 0.4978(3) 0.1903(10) 0.3548(3) 0.0467(10) Uani 1 1 d . . . . .
H12 H 0.444003 0.285059 0.362035 0.056 Uiso 1 1 calc R U . . .
C13 C 0.5865(3) 0.1642(11) 0.4313(3) 0.0471(10) Uani 1 1 d . . . . .
H13 H 0.592867 0.241832 0.490513 0.057 Uiso 1 1 calc R U . . .
C14 C 0.6702(3) 0.0195(10) 0.4227(3) 0.0427(9) Uani 1 1 d . . . . .
C15 C 0.8344(3) -0.1283(12) 0.4944(3) 0.0555(11) Uani 1 1 d . . . . .
H15 H 0.894146 -0.138194 0.548878 0.067 Uiso 1 1 calc R U . . .
C16 C 0.8328(3) -0.2552(12) 0.4102(3) 0.0544(11) Uani 1 1 d . . . . .
H16 H 0.889930 -0.346103 0.408638 0.065 Uiso 1 1 calc R U . . .
C17 C 0.7457(3) -0.2443(11) 0.3293(3) 0.0471(10) Uani 1 1 d . . . . .
H17 H 0.742608 -0.330989 0.272150 0.057 Uiso 1 1 calc R U . . .
C18 C 0.6611(3) -0.1014(9) 0.3334(3) 0.0388(8) Uani 1 1 d . . . . .
C19 C 0.5658(3) -0.0745(9) 0.2509(2) 0.0376(8) Uani 1 1 d . . . . .
B1 B 0.1992(3) 0.5473(12) 0.2325(3) 0.0431(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.345(5) . ?
O1 H1 0.8200 . ?
O2 B1 1.365(5) . ?
O2 H2A 0.8200 . ?
N1 C10 1.322(5) . ?
N1 C11 1.364(4) . ?
N2 C15 1.313(6) . ?
N2 C14 1.360(4) . ?
N3 C7 1.141(5) . ?
C1 C6 1.393(5) . ?
C1 C2 1.400(5) . ?
C1 B1 1.574(5) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(5) . ?
C4 C7 1.440(5) . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.359(5) . ?
C8 C19 1.406(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C19 1.405(5) . ?
C11 C12 1.436(5) . ?
C12 C13 1.350(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.424(5) . ?
C13 H13 0.9300 . ?
C14 C18 1.411(5) . ?
C15 C16 1.386(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.453(5) . ?

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
_geom_angle_publ_flag
B1 O1 H1 109.5 . . ?
B1 O2 H2A 109.5 . . ?
C10 N1 C11 117.2(3) . . ?
C15 N2 C14 117.4(3) . . ?
C6 C1 C2 116.9(3) . . ?
C6 C1 B1 122.9(3) . . ?
C2 C1 B1 120.2(3) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 C7 120.7(3) . . ?
C5 C4 C7 118.9(3) . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 122.0(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
N3 C7 C4 177.9(4) . . ?
C9 C8 C19 120.1(4) . . ?
C9 C8 H8 120.0 . . ?
C19 C8 H8 120.0 . . ?
C8 C9 C10 118.4(4) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N1 C10 C9 124.4(4) . . ?
N1 C10 H10 117.8 . . ?
C9 C10 H10 117.8 . . ?
N1 C11 C19 122.6(3) . . ?
N1 C11 C12 117.4(3) . . ?
C19 C11 C12 120.0(3) . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
N2 C14 C18 122.4(3) . . ?
N2 C14 C13 117.5(3) . . ?
C18 C14 C13 120.0(3) . . ?
N2 C15 C16 124.5(4) . . ?
N2 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
C17 C16 C15 118.8(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 119.4(4) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C14 117.5(3) . . ?
C17 C18 C19 123.2(3) . . ?
C14 C18 C19 119.2(3) . . ?
C11 C19 C8 117.3(3) . . ?
C11 C19 C18 118.8(3) . . ?
C8 C19 C18 123.9(3) . . ?
O1 B1 O2 119.6(4) . . ?
O1 B1 C1 117.6(3) . . ?
O2 B1 C1 122.8(3) . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.048

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronicacid_44Azopyridine
_database_code_depnum_ccdc_archive 'CCDC 2260231'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 B2 N6 O4'
_chemical_formula_weight         478.08

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.2777(5)
_cell_length_b                   7.1087(4)
_cell_length_c                   19.6723(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.218(2)
_cell_angle_gamma                90
_cell_volume                     1152.79(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2537
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.36

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6272
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6771
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.048
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2350
_reflns_number_gt                1934
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.4762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2350
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.32329(13) 0.35678(18) 0.63572(6) 0.0278(3) Uani 1 1 d . . . . .
H1 H 0.326150 0.318988 0.675191 0.068(8) Uiso 1 1 calc R . . . .
O2 O 0.09574(12) 0.14250(17) 0.61985(5) 0.0234(3) Uani 1 1 d . . . . .
H2A H 0.122783 0.116842 0.659908 0.053(7) Uiso 1 1 calc R . . . .
N1 N 0.38571(16) 0.3643(2) 0.77612(7) 0.0255(3) Uani 1 1 d . . . . .
N2 N 0.12450(15) 0.5292(2) 0.25470(6) 0.0249(3) Uani 1 1 d . . . . .
C1 C 0.17680(15) 0.3288(2) 0.51974(7) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.05002(16) 0.2602(2) 0.47476(7) 0.0165(3) Uani 1 1 d . . . . .
H2 H -0.024817 0.177411 0.490797 0.020 Uiso 1 1 calc R U . . .
C3 C 0.03386(16) 0.3132(2) 0.40673(7) 0.0175(3) Uani 1 1 d . . . . .
H3 H -0.051736 0.267510 0.377457 0.021 Uiso 1 1 calc R U . . .
C4 C 0.14725(16) 0.4359(2) 0.38246(7) 0.0159(3) Uani 1 1 d . . . . .
C5 C 0.27620(16) 0.5051(2) 0.42594(7) 0.0168(3) Uani 1 1 d . . . . .
H5 H 0.352768 0.584903 0.409534 0.020 Uiso 1 1 calc R U . . .
C6 C 0.28790(16) 0.4528(2) 0.49380(7) 0.0164(3) Uani 1 1 d . . . . .
H6 H 0.372005 0.501271 0.523214 0.020 Uiso 1 1 calc R U . . .
C7 C 0.13392(16) 0.4886(2) 0.31138(8) 0.0185(3) Uani 1 1 d . . . . .
C8 C 0.28204(18) 0.4667(3) 0.80862(9) 0.0277(4) Uani 1 1 d . . . . .
H8 H 0.187638 0.508266 0.783920 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3062(2) 0.5144(2) 0.87616(9) 0.0308(4) Uani 1 1 d . . . . .
H9 H 0.230051 0.585752 0.896758 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4456(2) 0.4543(3) 0.91264(8) 0.0321(4) Uani 1 1 d . . . . .
C11 C 0.55551(18) 0.3483(3) 0.88049(9) 0.0323(5) Uani 1 1 d . . . . .
H11 H 0.651068 0.306126 0.904135 0.039 Uiso 1 1 calc R U . . .
C12 C 0.52006(19) 0.3066(2) 0.81249(9) 0.0283(4) Uani 1 1 d . . . . .
H12 H 0.593735 0.234337 0.790813 0.034 Uiso 1 1 calc R U . . .
B1 B 0.19985(18) 0.2720(3) 0.59767(8) 0.0172(4) Uani 1 1 d . . . . .
N3 N 0.4411(4) 0.5314(5) 0.9821(5) 0.0187(14) Uani 0.65(2) 1 d . . P A 1
N3A N 0.4609(7) 0.5561(9) 1.0180(8) 0.018(3) Uani 0.35(2) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.3523(19) . ?
O1 H1 0.8200 . ?
O2 B1 1.360(2) . ?
O2 H2A 0.8200 . ?
N1 C12 1.331(2) . ?
N1 C8 1.332(2) . ?
N2 C7 1.1475(19) . ?
C1 C2 1.3977(19) . ?
C1 C6 1.403(2) . ?
C1 B1 1.580(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(2) . ?
C4 C7 1.442(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.368(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C10 N3 1.475(9) . ?
C10 N3A 1.508(15) 3_667 ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N3 N3 1.233(12) 3_667 ?
N3A N3A 1.28(2) 3_667 ?

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
_geom_angle_publ_flag
B1 O1 H1 109.5 . . ?
B1 O2 H2A 109.5 . . ?
C12 N1 C8 116.97(14) . . ?
C2 C1 C6 117.93(13) . . ?
C2 C1 B1 122.84(13) . . ?
C6 C1 B1 119.23(12) . . ?
C3 C2 C1 121.17(13) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.43(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.72(13) . . ?
C5 C4 C7 119.32(13) . . ?
C3 C4 C7 119.94(13) . . ?
C6 C5 C4 118.71(13) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 122.02(13) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
N2 C7 C4 179.31(16) . . ?
N1 C8 C9 123.91(15) . . ?
N1 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C8 C9 C10 118.22(15) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C9 C10 C11 119.31(15) . . ?
C9 C10 N3 106.2(2) . . ?
C11 C10 N3 134.5(2) . . ?
C9 C10 N3A 145.8(4) . 3_667 ?
C11 C10 N3A 94.7(4) . 3_667 ?
N3 C10 N3A 40.0(2) . 3_667 ?
C12 C11 C10 118.21(15) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
N1 C12 C11 123.38(15) . . ?
N1 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
O1 B1 O2 126.39(14) . . ?
O1 B1 C1 116.20(13) . . ?
O2 B1 C1 117.41(13) . . ?
N3 N3 C10 108.1(7) 3_667 . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.049

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronic_monoester_12bis(4pyridyl)ethene
_database_code_depnum_ccdc_archive 'CCDC 2260232'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 B2 N4 O4'
_chemical_formula_weight         504.15

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.9427(2)
_cell_length_b                   22.6930(9)
_cell_length_c                   14.9291(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.421(7)
_cell_angle_gamma                90
_cell_volume                     1333.35(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1612
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      22.65

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6183
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9015
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.256
_diffrn_reflns_theta_max         26.452
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2719
_reflns_number_gt                1511
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0648P)²+0.2349P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2719
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.7108(4) 0.19086(7) 0.60962(11) 0.0685(5) Uani 1 1 d . . . . .
N1 N 0.4156(5) 0.36737(9) 0.79058(12) 0.0615(6) Uani 1 1 d . . . . .
C1 C 0.8906(7) 0.27982(11) 0.47993(16) 0.0673(7) Uani 1 1 d . . . . .
H1 H 0.855140 0.241047 0.461475 0.081 Uiso 1 1 calc R U . . .
B1 B 0.6976(7) 0.24833(12) 0.63507(18) 0.0569(7) Uani 1 1 d . . . . .
O2 O 0.5758(5) 0.26128(8) 0.71528(10) 0.0726(6) Uani 1 1 d . . . . .
H2A H 0.544(7) 0.3028(14) 0.7198(8) 0.109 Uiso 1 1 calc R U . . .
N2 N 1.2791(8) 0.45330(14) 0.3348(2) 0.1272(12) Uani 1 1 d . . . . .
C2 C 1.0058(7) 0.32005(13) 0.41963(17) 0.0751(8) Uani 1 1 d . . . . .
H2 H 1.047898 0.308319 0.361641 0.090 Uiso 1 1 calc R U . . .
C3 C 1.0581(6) 0.37743(12) 0.44550(18) 0.0670(7) Uani 1 1 d . . . . .
C4 C 0.9956(7) 0.39448(12) 0.53166(18) 0.0741(8) Uani 1 1 d . . . . .
H4 H 1.030493 0.433337 0.549742 0.089 Uiso 1 1 calc R U . . .
C5 C 0.8809(7) 0.35328(11) 0.59073(17) 0.0669(7) Uani 1 1 d . . . . .
H5 H 0.839126 0.365211 0.648648 0.080 Uiso 1 1 calc R U . . .
C8 C 0.3887(7) 0.42435(11) 0.77576(16) 0.0683(7) Uani 1 1 d . . . . .
H8 H 0.457717 0.439092 0.721640 0.082 Uiso 1 1 calc R U . . .
C7 C 1.1816(8) 0.41989(14) 0.3834(2) 0.0868(9) Uani 1 1 d . . . . .
C6 C 0.8257(5) 0.29518(10) 0.56735(14) 0.0529(6) Uani 1 1 d . . . . .
C9 C 0.2636(7) 0.46327(12) 0.8363(2) 0.0820(9) Uani 1 1 d . . . . .
H9 H 0.249767 0.503190 0.822504 0.098 Uiso 1 1 calc R U . . .
C10 C 0.1584(7) 0.44329(16) 0.9177(2) 0.0807(9) Uani 1 1 d . . . . .
C11 C 0.1854(7) 0.38403(15) 0.93173(17) 0.0806(9) Uani 1 1 d . . . . .
H11 H 0.116187 0.367907 0.984920 0.097 Uiso 1 1 calc R U . . .
C12 C 0.3126(7) 0.34834(11) 0.86881(16) 0.0706(7) Uani 1 1 d . . . . .
H12 H 0.328554 0.308231 0.881124 0.085 Uiso 1 1 calc R U . . .
C13 C 0.0378(19) 0.5018(5) 0.9576(9) 0.054(4) Uani 0.385(19) 1 d . . P A 1
H13 H 0.019874 0.536659 0.924825 0.065 Uiso 0.385(19) 1 calc R U P A 1
C15 C 0.0188(12) 0.4721(4) 0.9982(6) 0.059(2) Uani 0.615(19) 1 d . . P A 2
H15 H -0.041041 0.448889 1.046179 0.071 Uiso 0.615(19) 1 calc R U P A 2
C14 C 0.5884(8) 0.14581(11) 0.66638(19) 0.0806(9) Uani 1 1 d . . . . .
H14A H 0.520005 0.112175 0.630710 0.121 Uiso 1 1 calc R U . . .
H14B H 0.397413 0.160433 0.696611 0.121 Uiso 1 1 calc R U . . .
H14C H 0.765665 0.134566 0.709908 0.121 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.360(3) . ?
O1 C14 1.430(3) . ?
N1 C8 1.315(3) . ?
N1 C12 1.331(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.389(3) . ?
B1 O2 1.349(3) . ?
B1 C6 1.571(4) . ?
N2 C7 1.133(3) . ?
C2 C3 1.370(4) . ?
C3 C4 1.379(4) . ?
C3 C7 1.442(4) . ?
C4 C5 1.380(3) . ?
C5 C6 1.378(3) . ?
C8 C9 1.376(3) . ?
C9 C10 1.383(4) . ?
C10 C11 1.364(4) . ?
C10 C15 1.501(9) . ?
C10 C13 1.543(13) . ?
C11 C12 1.359(3) . ?
C13 C13 1.32(3) 3_567 ?
C15 C15 1.279(19) 3_567 ?

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
_geom_angle_publ_flag
B1 O1 C14 120.00(19) . . ?
C8 N1 C12 116.1(2) . . ?
C2 C1 C6 122.3(2) . . ?
O2 B1 O1 118.6(2) . . ?
O2 B1 C6 124.7(2) . . ?
O1 B1 C6 116.7(2) . . ?
C3 C2 C1 119.7(2) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 C7 120.3(3) . . ?
C4 C3 C7 119.9(3) . . ?
C3 C4 C5 119.3(2) . . ?
C6 C5 C4 122.6(2) . . ?
N1 C8 C9 123.3(2) . . ?
N2 C7 C3 179.8(4) . . ?
C5 C6 C1 116.3(2) . . ?
C5 C6 B1 122.4(2) . . ?
C1 C6 B1 121.3(2) . . ?
C8 C9 C10 120.3(3) . . ?
C11 C10 C9 115.7(2) . . ?
C11 C10 C15 109.5(5) . . ?
C9 C10 C15 134.8(5) . . ?
C11 C10 C13 144.3(6) . . ?
C9 C10 C13 99.9(6) . . ?
C12 C11 C10 120.7(3) . . ?
N1 C12 C11 123.9(3) . . ?
C13 C13 C10 114.1(13) 3_567 . ?
C15 C15 C10 120.9(10) 3_567 . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronicacid_12bis(4pyridyl)ethene
_database_code_depnum_ccdc_archive 'CCDC 2260235'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 B2 N4 O4'
_chemical_formula_weight         476.09

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4431(5)
_cell_length_b                   7.3205(4)
_cell_length_c                   19.6867(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.592(4)
_cell_angle_gamma                90
_cell_volume                     1214.40(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2598
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      24.32

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6527
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14399
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.073
_diffrn_reflns_theta_max         26.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2462
_reflns_number_gt                1609
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+0.4049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2462
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.6924(2) 0.6264(2) 0.36891(6) 0.0783(5) Uani 1 1 d . . . . .
H1 H 0.694059 0.659520 0.329175 0.117 Uiso 1 1 calc R U . . .
O2 O 0.8935(2) 0.8554(2) 0.38567(8) 0.0738(5) Uani 1 1 d . . . . .
H4 H 0.877(3) 0.883(3) 0.3458(13) 0.093(9) Uiso 1 1 d . . . . .
N1 N 0.6332(2) 0.6273(3) 0.23045(8) 0.0662(5) Uani 1 1 d . . . . .
N2 N 0.8743(2) 0.4764(3) 0.74834(8) 0.0780(6) Uani 1 1 d . . . . .
C1 C 0.8228(2) 0.6650(2) 0.48448(8) 0.0438(4) Uani 1 1 d . . . . .
C2 C 0.7176(2) 0.5431(3) 0.51153(9) 0.0503(5) Uani 1 1 d . . . . .
H2 H 0.636930 0.493158 0.483014 0.060 Uiso 1 1 calc R U . . .
C3 C 0.7287(2) 0.4936(3) 0.57913(9) 0.0518(5) Uani 1 1 d . . . . .
H3 H 0.654929 0.414291 0.596225 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8513(2) 0.5636(2) 0.62125(8) 0.0475(5) Uani 1 1 d . . . . .
C5 C 0.9588(2) 0.6845(3) 0.59574(9) 0.0535(5) Uani 1 1 d . . . . .
H5 H 1.041431 0.731294 0.624027 0.064 Uiso 1 1 calc R U . . .
C6 C 0.9429(2) 0.7351(3) 0.52833(9) 0.0498(5) Uani 1 1 d . . . . .
H6 H 1.014350 0.818243 0.511757 0.060 Uiso 1 1 calc R U . . .
C7 C 0.8647(2) 0.5142(3) 0.69216(10) 0.0571(5) Uani 1 1 d . . . . .
C8 C 0.7229(3) 0.5284(3) 0.19189(12) 0.0686(6) Uani 1 1 d . . . . .
H8 H 0.817531 0.481706 0.211475 0.082 Uiso 1 1 calc R U . . .
C9 C 0.6846(3) 0.4909(3) 0.12471(11) 0.0685(6) Uani 1 1 d . . . . .
H9 H 0.752361 0.421101 0.099774 0.082 Uiso 1 1 calc R U . . .
C10 C 0.5453(3) 0.5569(3) 0.09449(10) 0.0652(6) Uani 1 1 d . . . . .
C11 C 0.4535(3) 0.6586(3) 0.13432(12) 0.0756(7) Uani 1 1 d . . . . .
H11 H 0.357855 0.706482 0.116282 0.091 Uiso 1 1 calc R U . . .
C12 C 0.5012(3) 0.6903(3) 0.20055(12) 0.0738(6) Uani 1 1 d . . . . .
H12 H 0.435945 0.761317 0.226287 0.089 Uiso 1 1 calc R U . . .
B1 B 0.8020(3) 0.7192(3) 0.40718(10) 0.0502(5) Uani 1 1 d . . . . .
C13 C 0.5592(16) 0.4831(11) 0.0226(5) 0.049(3) Uani 0.371(15) 1 d . . P A 1
H13 H 0.647587 0.416840 0.011188 0.059 Uiso 0.371(15) 1 calc R U P A 1
C14 C 0.4646(9) 0.5422(7) 0.0240(3) 0.0558(18) Uani 0.629(15) 1 d . . P A 2
H14 H 0.364757 0.593329 0.014764 0.067 Uiso 0.629(15) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.341(2) . ?
O2 B1 1.346(3) . ?
N1 C12 1.312(3) . ?
N1 C8 1.321(3) . ?
N2 C7 1.138(2) . ?
C1 C6 1.388(2) . ?
C1 C2 1.389(2) . ?
C1 B1 1.572(3) . ?
C2 C3 1.377(2) . ?
C3 C4 1.384(2) . ?
C4 C5 1.384(3) . ?
C4 C7 1.440(2) . ?
C5 C6 1.376(2) . ?
C8 C9 1.370(3) . ?
C9 C10 1.372(3) . ?
C10 C11 1.359(3) . ?
C10 C14 1.512(6) . ?
C10 C13 1.525(10) . ?
C11 C12 1.360(3) . ?
C13 C13 1.32(3) 3_665 ?
C14 C14 1.303(16) 3_665 ?

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
_geom_angle_publ_flag
C12 N1 C8 115.88(18) . . ?
C6 C1 C2 117.32(16) . . ?
C6 C1 B1 122.80(17) . . ?
C2 C1 B1 119.87(16) . . ?
C3 C2 C1 122.23(17) . . ?
C2 C3 C4 119.01(18) . . ?
C3 C4 C5 120.16(16) . . ?
C3 C4 C7 119.87(18) . . ?
C5 C4 C7 119.94(17) . . ?
C6 C5 C4 119.68(17) . . ?
C5 C6 C1 121.56(18) . . ?
N2 C7 C4 179.3(2) . . ?
N1 C8 C9 123.7(2) . . ?
C8 C9 C10 119.5(2) . . ?
C11 C10 C9 116.57(19) . . ?
C11 C10 C14 109.2(4) . . ?
C9 C10 C14 134.2(4) . . ?
C11 C10 C13 144.0(6) . . ?
C9 C10 C13 99.4(6) . . ?
C10 C11 C12 120.1(2) . . ?
N1 C12 C11 124.2(2) . . ?
O1 B1 O2 126.02(18) . . ?
O1 B1 C1 116.58(18) . . ?
O2 B1 C1 117.40(17) . . ?
C13 C13 C10 117.5(14) 3_665 . ?
C14 C14 C10 119.9(9) 3_665 . ?

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.033

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronic_monoester_44Azopyridine
_database_code_depnum_ccdc_archive 'CCDC 2260234'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 B2 N6 O4'
_chemical_formula_weight         506.13

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.8043(3)
_cell_length_b                   22.3944(13)
_cell_length_c                   14.7329(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.107(6)
_cell_angle_gamma                90
_cell_volume                     1251.95(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2465
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.54

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6074
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9656
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.316
_diffrn_reflns_theta_max         26.382
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2540
_reflns_number_gt                1854
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0734P)²+0.9805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2540
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.6680(4) 0.19066(7) 0.60588(11) 0.0242(4) Uani 1 1 d . . . . .
O2 O 0.5227(4) 0.26105(7) 0.71537(11) 0.0252(4) Uani 1 1 d . . . . .
H2A H 0.498(7) 0.3023(13) 0.7217(8) 0.038 Uiso 1 1 calc R U . . .
N1 N 0.3609(5) 0.36813(8) 0.79347(13) 0.0220(4) Uani 1 1 d . . . . .
N2 N -0.0122(5) 0.47256(8) 1.00407(14) 0.0262(5) Uani 1 1 d . . . . .
N3 N 1.2563(6) 0.46016(11) 0.33363(17) 0.0408(6) Uani 1 1 d . . . . .
C1 C 0.2489(6) 0.34475(10) 0.86989(16) 0.0234(5) Uani 1 1 d . . . . .
H1 H 0.255686 0.303476 0.876810 0.028 Uiso 1 1 calc R U . . .
C2 C 0.1235(6) 0.37864(10) 0.93917(16) 0.0234(5) Uani 1 1 d . . . . .
H2 H 0.045791 0.360610 0.990956 0.028 Uiso 1 1 calc R U . . .
C3 C 0.1168(6) 0.43996(10) 0.92932(16) 0.0217(5) Uani 1 1 d . . . . .
C4 C 0.2256(6) 0.46533(10) 0.85003(16) 0.0253(5) Uani 1 1 d . . . . .
H4 H 0.218024 0.506441 0.841198 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3460(6) 0.42757(10) 0.78440(16) 0.0242(5) Uani 1 1 d . . . . .
H5 H 0.420303 0.444415 0.731342 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7759(6) 0.29762(10) 0.56572(15) 0.0200(5) Uani 1 1 d . . . . .
C7 C 0.8368(6) 0.28214(10) 0.47633(16) 0.0246(5) Uani 1 1 d . . . . .
H7 H 0.795300 0.243064 0.457038 0.030 Uiso 1 1 calc R U . . .
C8 C 0.9573(7) 0.32339(11) 0.41550(16) 0.0266(6) Uani 1 1 d . . . . .
H8 H 0.996310 0.312075 0.356324 0.032 Uiso 1 1 calc R U . . .
C9 C 1.0190(6) 0.38177(10) 0.44412(16) 0.0239(5) Uani 1 1 d . . . . .
C10 C 0.9600(6) 0.39887(10) 0.53286(17) 0.0255(5) Uani 1 1 d . . . . .
H10 H 1.001893 0.437967 0.551994 0.031 Uiso 1 1 calc R U . . .
C11 C 0.8380(6) 0.35684(10) 0.59207(16) 0.0228(5) Uani 1 1 d . . . . .
H11 H 0.796334 0.368371 0.650988 0.027 Uiso 1 1 calc R U . . .
C12 C 1.1506(7) 0.42556(11) 0.38236(17) 0.0295(6) Uani 1 1 d . . . . .
C13 C 0.5509(7) 0.14328(10) 0.66224(17) 0.0281(6) Uani 1 1 d . . . . .
H13A H 0.502855 0.108309 0.625766 0.042 Uiso 1 1 calc R U . . .
H13B H 0.340360 0.155444 0.689376 0.042 Uiso 1 1 calc R U . . .
H13C H 0.731438 0.134454 0.709220 0.042 Uiso 1 1 calc R U . . .
B1 B 0.6471(7) 0.24883(11) 0.63382(18) 0.0203(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.370(3) . ?
O1 C13 1.438(3) . ?
O2 B1 1.350(3) . ?
O2 H2A 0.93(3) . ?
N1 C5 1.339(3) . ?
N1 C1 1.339(3) . ?
N2 N2 1.239(4) 3_567 ?
N2 C3 1.437(3) . ?
N3 C12 1.148(3) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(3) . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.397(3) . ?
C6 C11 1.397(3) . ?
C6 B1 1.585(3) . ?
C7 C8 1.388(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(3) . ?
C9 C12 1.451(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
_geom_angle_publ_flag
B1 O1 C13 120.08(18) . . ?
B1 O2 H2A 109.5 . . ?
C5 N1 C1 117.33(19) . . ?
N2 N2 C3 113.4(2) 3_567 . ?
N1 C1 C2 123.6(2) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 N2 115.4(2) . . ?
C4 C3 N2 125.2(2) . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 123.4(2) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C7 C6 C11 117.5(2) . . ?
C7 C6 B1 120.4(2) . . ?
C11 C6 B1 122.2(2) . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 C12 120.3(2) . . ?
C10 C9 C12 119.2(2) . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C6 121.8(2) . . ?
C10 C11 H11 119.1 . . ?
C6 C11 H11 119.1 . . ?
N3 C12 C9 179.7(3) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 B1 O1 119.4(2) . . ?
O2 B1 C6 124.6(2) . . ?
O1 B1 C6 115.98(19) . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.062

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronicacid_12bis(4pyridyl)ethene_dihydrate
_database_code_depnum_ccdc_archive 'CCDC 2260233'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 B2 N4 O6.78'
_chemical_formula_weight         524.65

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8665(2)
_cell_length_b                   11.5022(5)
_cell_length_c                   15.8177(8)
_cell_angle_alpha                77.285(2)
_cell_angle_beta                 86.962(4)
_cell_angle_gamma                87.577(5)
_cell_volume                     684.91(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2430
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      23.41

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             274
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5865
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14656
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.999
_diffrn_reflns_theta_max         26.629
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2779
_reflns_number_gt                1510
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1180P)²+0.0805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2779
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1404
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2325
_refine_ls_wR_factor_gt          0.1975
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2321(7) 0.3832(2) 0.46954(13) 0.0763(8) Uani 1 1 d . . . . .
H1 H 0.327583 0.319216 0.466189 0.114 Uiso 1 1 calc R U . . .
B1 B 0.2447(9) 0.4584(3) 0.3902(2) 0.0540(9) Uani 1 1 d . . . . .
C1 C 0.4155(7) 0.4229(2) 0.30624(17) 0.0467(7) Uani 1 1 d . . . . .
N1 N 0.4715(7) 0.1185(2) 0.69687(17) 0.0698(8) Uani 1 1 d . . . . .
C2 C 0.5783(8) 0.3130(3) 0.30597(18) 0.0534(8) Uani 1 1 d . . . . .
H2 H 0.593566 0.257316 0.358179 0.064 Uiso 1 1 calc R U . . .
O2 O 0.0993(6) 0.5681(2) 0.38148(14) 0.0732(7) Uani 1 1 d . . . . .
H4 H 0.050308 0.581408 0.429602 0.130(18) Uiso 1 1 calc R . . . .
O4 O 1.000000 0.000000 0.500000 0.499(14) Uani 1 2 d S . P . .
N2 N 0.9629(8) 0.3125(3) 0.0131(2) 0.0822(9) Uani 1 1 d . . . . .
C4 C 0.6988(7) 0.3671(3) 0.15301(18) 0.0483(7) Uani 1 1 d . . . . .
C3 C 0.7178(7) 0.2834(3) 0.23137(18) 0.0540(8) Uani 1 1 d . . . . .
H3 H 0.823262 0.208802 0.233154 0.065 Uiso 1 1 calc R U . . .
O3 O 0.4708(16) 0.1533(3) 0.52229(19) 0.190(2) Uani 1 1 d . . . . .
C5 C 0.5428(7) 0.4769(3) 0.15100(18) 0.0546(8) Uani 1 1 d . . . . .
H5 H 0.531221 0.532806 0.098787 0.066 Uiso 1 1 calc R U . . .
C6 C 0.4019(7) 0.5047(3) 0.22722(18) 0.0520(8) Uani 1 1 d . . . . .
H6 H 0.296618 0.579396 0.225280 0.062 Uiso 1 1 calc R U . . .
C9 C 0.3294(8) 0.1756(3) 0.8303(2) 0.0619(9) Uani 1 1 d . . . . .
H9 H 0.234047 0.233318 0.858348 0.074 Uiso 1 1 calc R U . . .
C8 C 0.3400(9) 0.1964(3) 0.7415(2) 0.0721(10) Uani 1 1 d . . . . .
H8 H 0.250219 0.268842 0.710885 0.086 Uiso 1 1 calc R U . . .
C7 C 0.8461(8) 0.3366(3) 0.0751(2) 0.0584(8) Uani 1 1 d . . . . .
C10 C 0.4590(7) 0.0698(3) 0.87817(19) 0.0535(8) Uani 1 1 d . . . . .
C11 C 0.5982(8) -0.0121(3) 0.8313(2) 0.0631(9) Uani 1 1 d . . . . .
H11 H 0.689173 -0.085276 0.860195 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6002(9) 0.0158(3) 0.7428(2) 0.0683(9) Uani 1 1 d . . . . .
H12 H 0.696352 -0.039807 0.712933 0.082 Uiso 1 1 calc R U . . .
C13 C 0.4452(8) 0.0489(3) 0.9732(2) 0.0581(8) Uani 1 1 d . . . . .
H13 H 0.350566 0.110058 0.997800 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.359(4) . ?
O1 H1 0.8200 . ?
B1 O2 1.341(4) . ?
B1 C1 1.577(4) . ?
C1 C2 1.389(4) . ?
C1 C6 1.391(4) . ?
N1 C8 1.326(4) . ?
N1 C12 1.336(4) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
O2 H4 0.8200 . ?
N2 C7 1.142(4) . ?
C4 C5 1.372(4) . ?
C4 C3 1.395(4) . ?
C4 C7 1.437(4) . ?
C3 H3 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C9 C8 1.372(5) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.396(4) . ?
C10 C13 1.467(4) . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C13 1.320(6) 2_657 ?
C13 H13 0.9300 . ?

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
_geom_angle_publ_flag
B1 O1 H1 109.5 . . ?
O2 B1 O1 118.9(3) . . ?
O2 B1 C1 117.6(3) . . ?
O1 B1 C1 123.5(3) . . ?
C2 C1 C6 117.2(3) . . ?
C2 C1 B1 123.7(3) . . ?
C6 C1 B1 119.1(3) . . ?
C8 N1 C12 116.7(3) . . ?
C3 C2 C1 122.5(3) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
B1 O2 H4 109.5 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 C7 120.8(3) . . ?
C3 C4 C7 119.1(3) . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 121.3(3) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
N1 C8 C9 123.4(3) . . ?
N1 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
N2 C7 C4 179.9(4) . . ?
C9 C10 C11 116.3(3) . . ?
C9 C10 C13 119.6(3) . . ?
C11 C10 C13 124.1(3) . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N1 C12 C11 123.5(3) . . ?
N1 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C13 C13 C10 125.9(4) 2_657 . ?
C13 C13 H13 117.0 2_657 . ?
C10 C13 H13 117.0 . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronicacid_Azopyridine_hydrate
_database_code_depnum_ccdc_archive 'CCDC 2260236'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-07-04 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 B N5 O3'
_chemical_formula_weight         349.16

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8653(3)
_cell_length_b                   9.0872(4)
_cell_length_c                   12.2227(5)
_cell_angle_alpha                105.5490(10)
_cell_angle_beta                 108.761(3)
_cell_angle_gamma                90.865(6)
_cell_volume                     892.67(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4572
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      23.39

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6276
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25898
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         26.544
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3672
_reflns_number_gt                1990
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0791P)²+0.1490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.057(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3672
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1422
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8333(2) 0.1499(2) 0.54252(15) 0.0852(5) Uani 1 1 d . . . . .
H1 H 0.854117 0.165931 0.485753 0.128 Uiso 1 1 calc R U . . .
O2 O 0.6164(2) 0.2901(2) 0.47570(17) 0.1006(6) Uani 1 1 d . . . . .
H2 H 0.668293 0.303509 0.433787 0.151 Uiso 1 1 calc R U . . .
O3 O 0.0287(3) 0.1009(4) 0.4072(3) 0.1441(10) Uani 1 1 d G . . . .
H3A H 0.040107 0.141542 0.376624 0.216 Uiso 1 1 d G U . . .
H4A H 0.055151 0.007950 0.395019 0.49(6) Uiso 1 1 d G . . . .
N1 N 0.3181(3) 0.0560(3) 0.9289(2) 0.0976(7) Uani 1 1 d . . . . .
N2 N 0.2759(4) 0.6164(3) -0.3110(3) 0.1003(8) Uani 1 1 d . . . . .
N3 N 0.1161(3) 0.2439(3) 0.2593(3) 0.0944(7) Uani 1 1 d . . . . .
C1 C 0.6094(3) 0.1630(2) 0.63062(18) 0.0615(6) Uani 1 1 d . . . . .
C2 C 0.4518(3) 0.1893(3) 0.6156(2) 0.0748(6) Uani 1 1 d . . . . .
H2A H 0.395868 0.229592 0.553688 0.090 Uiso 1 1 calc R U . . .
C3 C 0.3756(3) 0.1575(3) 0.6896(2) 0.0767(7) Uani 1 1 d . . . . .
H3 H 0.268667 0.173788 0.676271 0.092 Uiso 1 1 calc R U . . .
C4 C 0.4576(3) 0.1014(2) 0.78339(19) 0.0647(6) Uani 1 1 d . . . . .
C5 C 0.6139(3) 0.0732(3) 0.8009(2) 0.0763(7) Uani 1 1 d . . . . .
H5 H 0.669584 0.034384 0.863766 0.092 Uiso 1 1 calc R U . . .
C6 C 0.6877(3) 0.1032(3) 0.72422(19) 0.0728(6) Uani 1 1 d . . . . .
H6 H 0.793217 0.082652 0.735739 0.087 Uiso 1 1 calc R U . . .
C7 C 0.3786(3) 0.0748(3) 0.8640(2) 0.0761(7) Uani 1 1 d . . . . .
C8 C 0.1596(4) 0.5070(4) -0.3413(3) 0.1066(10) Uani 1 1 d . . . . .
H8 H 0.097281 0.469209 -0.422339 0.128 Uiso 1 1 calc R U . . .
C9 C 0.1242(3) 0.4448(3) -0.2609(3) 0.0934(8) Uani 1 1 d . . . . .
H9 H 0.039528 0.367986 -0.286281 0.112 Uiso 1 1 calc R U . . .
C10 C 0.2164(3) 0.4987(3) -0.1432(2) 0.0749(7) Uani 1 1 d . . . . .
C11 C 0.3385(3) 0.6105(3) -0.1098(2) 0.0852(7) Uani 1 1 d . . . . .
H11 H 0.404206 0.648233 -0.029547 0.102 Uiso 1 1 calc R U . . .
C12 C 0.3629(4) 0.6664(3) -0.1959(3) 0.0952(9) Uani 1 1 d . . . . .
H12 H 0.445839 0.744426 -0.172153 0.114 Uiso 1 1 calc R U . . .
C13 C 0.0276(4) 0.1942(3) 0.1431(4) 0.0976(9) Uani 1 1 d . . . . .
H13 H -0.055042 0.115835 0.119140 0.117 Uiso 1 1 calc R U . . .
C14 C 0.0516(4) 0.2523(3) 0.0564(3) 0.0929(8) Uani 1 1 d . . . . .
H14 H -0.012806 0.213821 -0.024141 0.112 Uiso 1 1 calc R U . . .
C15 C 0.1710(4) 0.3666(3) 0.0912(3) 0.0819(8) Uani 1 1 d . . . . .
C16 C 0.2617(3) 0.4185(3) 0.2091(3) 0.0905(8) Uani 1 1 d . . . . .
H16 H 0.344377 0.497465 0.235234 0.109 Uiso 1 1 calc R U . . .
C17 C 0.2309(4) 0.3536(4) 0.2897(3) 0.0959(8) Uani 1 1 d . . . . .
H17 H 0.295345 0.389780 0.370339 0.115 Uiso 1 1 calc R U . . .
B1 B 0.6912(3) 0.2012(3) 0.5438(2) 0.0685(7) Uani 1 1 d . . . . .
N5 N 0.1288(16) 0.3842(16) -0.0307(15) 0.064(4) Uani 0.28(2) 1 d . . P A 1
N6 N 0.2510(17) 0.4820(16) -0.0223(17) 0.064(4) Uani 0.27(3) 1 d . . P A 1
N5A N 0.1533(7) 0.4140(7) -0.0761(9) 0.080(2) Uani 0.72(2) 1 d . . P A 2
N6A N 0.2367(7) 0.4544(6) 0.0255(10) 0.080(2) Uani 0.73(3) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.354(3) . ?
O1 H1 0.8200 . ?
O2 B1 1.344(3) . ?
O2 H2 0.8200 . ?
O3 H3A 0.6191 . ?
O3 H4A 0.8673 . ?
N1 C7 1.135(3) . ?
N2 C8 1.310(4) . ?
N2 C12 1.315(4) . ?
N3 C17 1.302(4) . ?
N3 C13 1.328(4) . ?
C1 C2 1.382(3) . ?
C1 C6 1.386(3) . ?
C1 B1 1.568(3) . ?
C2 C3 1.373(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 C7 1.445(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.369(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.352(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.353(4) . ?
C10 N6 1.46(2) . ?
C10 N5A 1.483(14) . ?
C11 C12 1.357(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.349(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.351(4) . ?
C15 N5 1.47(2) . ?
C15 N6A 1.500(13) . ?
C16 C17 1.367(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N5 N6 1.35(3) . ?
N5A N6A 1.175(13) . ?

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
_geom_angle_publ_flag
B1 O1 H1 109.5 . . ?
B1 O2 H2 109.5 . . ?
H3A O3 H4A 120.1 . . ?
C8 N2 C12 116.5(2) . . ?
C17 N3 C13 116.6(2) . . ?
C2 C1 C6 116.98(19) . . ?
C2 C1 B1 119.9(2) . . ?
C6 C1 B1 123.1(2) . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2A 119.1 . . ?
C1 C2 H2A 119.1 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.04(19) . . ?
C5 C4 C7 120.5(2) . . ?
C3 C4 C7 119.5(2) . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 122.1(2) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
N1 C7 C4 178.8(3) . . ?
N2 C8 C9 124.0(3) . . ?
N2 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 N6 145.9(7) . . ?
C11 C10 N6 94.7(7) . . ?
C9 C10 N5A 107.1(3) . . ?
C11 C10 N5A 133.5(4) . . ?
C10 C11 C12 118.5(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
N2 C12 C11 123.7(3) . . ?
N2 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
N3 C13 C14 123.6(3) . . ?
N3 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C15 C14 C13 118.2(3) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 118.8(2) . . ?
C14 C15 N5 92.8(7) . . ?
C16 C15 N5 148.2(7) . . ?
C14 C15 N6A 134.1(4) . . ?
C16 C15 N6A 107.1(4) . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
N3 C17 C16 123.4(3) . . ?
N3 C17 H17 118.3 . . ?
C16 C17 H17 118.3 . . ?
O2 B1 O1 122.8(2) . . ?
O2 B1 C1 116.9(2) . . ?
O1 B1 C1 120.3(2) . . ?
N6 N5 C15 103.6(13) . . ?
N5 N6 C10 105.4(13) . . ?
N6A N5A C10 108.0(9) . . ?
N5A N6A C15 106.9(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(4) . . . . ?
B1 C1 C2 C3 180.0(2) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C2 C3 C4 C5 -1.8(4) . . . . ?
C2 C3 C4 C7 177.2(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C7 C4 C5 C6 -178.4(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
B1 C1 C6 C5 178.7(2) . . . . ?
C12 N2 C8 C9 0.6(5) . . . . ?
N2 C8 C9 C10 -0.8(5) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C8 C9 C10 N6 -174.8(7) . . . . ?
C8 C9 C10 N5A 179.8(3) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
N6 C10 C11 C12 178.0(4) . . . . ?
N5A C10 C11 C12 -178.8(3) . . . . ?
C8 N2 C12 C11 0.3(4) . . . . ?
C10 C11 C12 N2 -1.1(4) . . . . ?
C17 N3 C13 C14 -0.1(4) . . . . ?
N3 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C13 C14 C15 N5 -176.0(4) . . . . ?
C13 C14 C15 N6A 177.7(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
N5 C15 C16 C17 173.1(7) . . . . ?
N6A C15 C16 C17 -177.8(2) . . . . ?
C13 N3 C17 C16 0.6(4) . . . . ?
C15 C16 C17 N3 -0.8(4) . . . . ?
C2 C1 B1 O2 14.7(3) . . . . ?
C6 C1 B1 O2 -165.1(2) . . . . ?
C2 C1 B1 O1 -167.5(2) . . . . ?
C6 C1 B1 O1 12.7(4) . . . . ?
C14 C15 N5 N6 -171.3(6) . . . . ?
C16 C15 N5 N6 15.0(11) . . . . ?
C15 N5 N6 C10 178.2(5) . . . . ?
C9 C10 N6 N5 -11.3(12) . . . . ?
C11 C10 N6 N5 173.2(6) . . . . ?
C9 C10 N5A N6A 176.8(3) . . . . ?
C11 C10 N5A N6A -3.5(5) . . . . ?
C10 N5A N6A C15 -179.7(2) . . . . ?
C14 C15 N6A N5A 5.3(5) . . . . ?
C16 C15 N6A N5A -177.0(3) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.033

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4Cyanophenylboronicacid_12bis(4pyridyl)ethane
_database_code_depnum_ccdc_archive 'CCDC 2260237'
loop_
_audit_author_name
_audit_author_address
'Samina Easmin'
;IIT Bhubaneswar
India
;
_audit_update_record             
;
2023-05-02 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 B N3 O3'
_chemical_formula_weight         349.19

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5470(4)
_cell_length_b                   11.5173(7)
_cell_length_c                   11.9183(8)
_cell_angle_alpha                99.982(5)
_cell_angle_beta                 102.829(4)
_cell_angle_gamma                105.296(7)
_cell_volume                     944.22(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5679
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.23

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6250
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26286
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.808
_diffrn_reflns_theta_max         26.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3941
_reflns_number_gt                2355
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0731P)²+0.3460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3941
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1955
_refine_ls_wR_factor_gt          0.1651
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.5817(3) 0.1962(2) 0.29630(17) 0.0902(6) Uani 1 1 d . . . . .
H1 H 0.600338 0.198347 0.231364 0.135 Uiso 1 1 calc R U . . .
O2 O 0.7002(3) 0.1345(2) 0.46559(16) 0.0843(6) Uani 1 1 d . . . . .
H2A H 0.630313 0.171322 0.488368 0.126 Uiso 1 1 calc R U . . .
O3 O 0.5527(4) 0.2310(3) 0.0764(2) 0.1096(9) Uani 1 1 d . . . . .
N1 N 0.4684(3) 0.2482(2) 0.5603(2) 0.0725(6) Uani 1 1 d . . . . .
N2 N -0.3073(4) 0.6285(2) 0.8963(2) 0.0883(7) Uani 1 1 d . . . . .
N3 N 1.2748(4) -0.1443(2) 0.1073(2) 0.0916(8) Uani 1 1 d . . . . .
C1 C 0.8270(3) 0.0758(2) 0.2952(2) 0.0580(6) Uani 1 1 d . . . . .
C2 C 0.9914(4) 0.0643(2) 0.3664(2) 0.0663(6) Uani 1 1 d . . . . .
H2 H 1.022790 0.094783 0.448255 0.080 Uiso 1 1 calc R U . . .
C3 C 1.1094(4) 0.0092(2) 0.3196(2) 0.0681(7) Uani 1 1 d . . . . .
H3 H 1.219992 0.004260 0.368951 0.082 Uiso 1 1 calc R U . . .
C4 C 1.0610(3) -0.0384(2) 0.1987(2) 0.0595(6) Uani 1 1 d . . . . .
C5 C 0.8958(3) -0.0304(2) 0.1248(2) 0.0620(6) Uani 1 1 d . . . . .
H5 H 0.862434 -0.063604 0.043290 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7819(3) 0.0275(2) 0.1738(2) 0.0620(6) Uani 1 1 d . . . . .
H6 H 0.672880 0.034108 0.124191 0.074 Uiso 1 1 calc R U . . .
C7 C 1.1814(4) -0.0973(2) 0.1481(2) 0.0692(7) Uani 1 1 d . . . . .
C8 C 0.4106(4) 0.2202(3) 0.6510(3) 0.0814(8) Uani 1 1 d . . . . .
H8 H 0.452243 0.161655 0.684768 0.098 Uiso 1 1 calc R U . . .
C9 C 0.2923(5) 0.2725(3) 0.6987(3) 0.1027(11) Uani 1 1 d . . . . .
H9 H 0.254116 0.248280 0.762351 0.123 Uiso 1 1 calc R U . . .
C10 C 0.2304(7) 0.3599(4) 0.6532(4) 0.1296(15) Uani 1 1 d . . . . .
C11 C 0.2904(7) 0.3879(4) 0.5591(4) 0.1358(16) Uani 1 1 d . . . . .
H11 H 0.252342 0.446907 0.524169 0.163 Uiso 1 1 calc R U . . .
C12 C 0.4056(5) 0.3306(3) 0.5153(3) 0.1002(11) Uani 1 1 d . . . . .
H12 H 0.441852 0.351076 0.449815 0.120 Uiso 1 1 calc R U . . .
C15 C -0.2968(5) 0.5196(3) 0.9074(3) 0.0984(10) Uani 1 1 d . . . . .
H15 H -0.369056 0.479349 0.951373 0.118 Uiso 1 1 calc R U . . .
C16 C -0.1868(6) 0.4613(3) 0.8587(4) 0.1143(13) Uani 1 1 d . . . . .
H16 H -0.184411 0.383994 0.870757 0.137 Uiso 1 1 calc R U . . .
C17 C -0.0819(6) 0.5147(4) 0.7934(4) 0.1229(14) Uani 1 1 d . . . . .
C18 C -0.0907(6) 0.6278(4) 0.7808(4) 0.1228(14) Uani 1 1 d . . . . .
H18 H -0.019303 0.669832 0.737453 0.147 Uiso 1 1 calc R U . . .
C19 C -0.2058(6) 0.6796(3) 0.8326(4) 0.1070(11) Uani 1 1 d . . . . .
H19 H -0.211600 0.756582 0.821434 0.128 Uiso 1 1 calc R U . . .
B1 B 0.6942(4) 0.1387(3) 0.3530(3) 0.0639(7) Uani 1 1 d . . . . .
H4 H 0.488(6) 0.277(4) 0.069(4) 0.137(15) Uiso 1 1 d . . . . .
H7 H 0.579(6) 0.216(4) 0.013(4) 0.133(15) Uiso 1 1 d . . . . .
C13A C 0.037(2) 0.3896(14) 0.6677(11) 0.123(5) Uani 0.44(2) 1 d . . P A 1
H13A H -0.014134 0.425753 0.605136 0.148 Uiso 0.44(2) 1 calc R U P A 1
H13B H -0.061048 0.315277 0.667382 0.148 Uiso 0.44(2) 1 calc R U P A 1
C14A C 0.104(2) 0.4772(11) 0.7815(11) 0.113(5) Uani 0.413(19) 1 d . . P A 1
H14A H 0.207311 0.548937 0.783253 0.136 Uiso 0.413(19) 1 calc R U P A 1
H14B H 0.146916 0.439333 0.844502 0.136 Uiso 0.413(19) 1 calc R U P A 1
C13B C 0.160(2) 0.4471(13) 0.7342(17) 0.195(7) Uani 0.56(2) 1 d . . P A 2
H13C H 0.194312 0.435855 0.814082 0.234 Uiso 0.56(2) 1 calc R U P A 2
H13D H 0.227407 0.532385 0.737090 0.234 Uiso 0.56(2) 1 calc R U P A 2
C14B C -0.0102(19) 0.4311(12) 0.7034(16) 0.172(5) Uani 0.587(19) 1 d . . P A 2
H14C H -0.077981 0.344346 0.694589 0.206 Uiso 0.587(19) 1 calc R U P A 2
H14D H -0.043151 0.448933 0.626203 0.206 Uiso 0.587(19) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.346(3) . ?
O2 B1 1.343(3) . ?
N1 C12 1.308(4) . ?
N1 C8 1.311(3) . ?
N2 C19 1.298(4) . ?
N2 C15 1.304(4) . ?
N3 C7 1.136(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.391(3) . ?
C1 B1 1.587(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.393(3) . ?
C4 C7 1.441(3) . ?
C5 C6 1.383(3) . ?
C8 C9 1.369(4) . ?
C9 C10 1.360(5) . ?
C10 C11 1.357(5) . ?
C10 C13B 1.548(12) . ?
C10 C13A 1.625(13) . ?
C11 C12 1.360(4) . ?
C15 C16 1.361(4) . ?
C16 C17 1.339(5) . ?
C17 C18 1.353(5) . ?
C17 C14B 1.596(13) . ?
C17 C14A 1.598(12) . ?
C18 C19 1.370(4) . ?
C13A C14A 1.44(2) . ?
C13B C14B 1.21(2) . ?

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
_geom_angle_publ_flag
C12 N1 C8 116.2(2) . . ?
C19 N2 C15 115.3(2) . . ?
C6 C1 C2 117.6(2) . . ?
C6 C1 B1 121.9(2) . . ?
C2 C1 B1 120.4(2) . . ?
C3 C2 C1 122.1(2) . . ?
C4 C3 C2 119.1(2) . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 C7 119.9(2) . . ?
C5 C4 C7 119.6(2) . . ?
C6 C5 C4 119.3(2) . . ?
C5 C6 C1 121.4(2) . . ?
N3 C7 C4 179.3(3) . . ?
N1 C8 C9 123.5(3) . . ?
C10 C9 C8 120.2(3) . . ?
C11 C10 C9 115.9(3) . . ?
C11 C10 C13B 123.6(6) . . ?
C9 C10 C13B 117.2(7) . . ?
C11 C10 C13A 116.6(6) . . ?
C9 C10 C13A 123.1(6) . . ?
C10 C11 C12 120.6(3) . . ?
N1 C12 C11 123.7(3) . . ?
N2 C15 C16 124.1(3) . . ?
C17 C16 C15 120.2(3) . . ?
C16 C17 C18 116.6(3) . . ?
C16 C17 C14B 119.4(5) . . ?
C18 C17 C14B 121.0(6) . . ?
C16 C17 C14A 119.1(5) . . ?
C18 C17 C14A 119.3(6) . . ?
C17 C18 C19 119.3(3) . . ?
N2 C19 C18 124.4(3) . . ?
O2 B1 O1 119.7(2) . . ?
O2 B1 C1 116.5(2) . . ?
O1 B1 C1 123.8(2) . . ?
C14A C13A C10 102.2(11) . . ?
C13A C14A C17 103.0(11) . . ?
C14B C13B C10 114.7(17) . . ?
C13B C14B C17 113.9(16) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.036

