#------------------------------------------------------------------------------
#$Date: 2020-03-05 01:08:15 +0100 (jue 05 de mar de 2020) $
#$Revision: 248943 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/33/7703325.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7703325
loop_
_publ_author_name
'Beagan, Daniel M.'
'Carta, Veronica'
'Caulton, Kenneth G.'
_publ_section_title
;
 A reagent for heteroatom borylation, including iron mediated reductive
 deoxygenation of nitrate yielding a dinitrosyl complex.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1681
_journal_page_last               1687
_journal_paper_doi               10.1039/d0dt00077a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         '0.5(C22 H32 B2 N2 O4)'
_chemical_formula_sum            'C11 H16 B N O2'
_chemical_formula_weight         205.06
_chemical_name_systematic        (Bpin)2bpy
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-03 deposited with the CCDC.	2020-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.808(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5143(6)
_cell_length_b                   10.6792(9)
_cell_length_c                   16.5422(14)
_cell_measurement_reflns_used    7792
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      3.14
_cell_volume                     1137.23(17)
_computing_cell_refinement       'Apex3, (Bruker,2016)'
_computing_data_collection       'Apex3, (Bruker,2007)'
_computing_data_reduction        'Apex3, (Bruker,2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER APEX DUO'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            22487
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.278
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex3, (Bruker,2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_preparation       synthesized
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         4619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1765
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2692
_reflns_number_total             4619
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00077a2.cif
_cod_data_source_block           19051_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7703323--7703325.cif.
;
_cod_database_code               7703325
_shelx_shelxl_version_number     2017/1
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.559(2)
 0.441(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_olex2_date_sample_data_collection 2019-05-03
_olex2_date_sample_submission    2019-05-03
_olex2_submission_original_sample_id dmb_19
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
N1 N 0.2163(3) 0.76591(15) 0.91191(10) 0.0422(5) Uani 1 1 d .
O2 O -0.0951(2) 0.86420(13) 0.83625(9) 0.0502(5) Uani 1 1 d .
O3 O 0.1952(2) 0.98583(14) 0.87039(9) 0.0547(5) Uani 1 1 d .
C4 C 0.4446(3) 0.55160(17) 0.98423(11) 0.0376(5) Uani 1 1 d .
C5 C 0.5311(4) 0.67527(19) 0.98118(13) 0.0489(6) Uani 1 1 d .
H5 H 0.669423 0.687241 1.003764 0.059 Uiso 1 1 calc R
C6 C 0.2254(3) 0.54795(19) 0.94933(12) 0.0438(6) Uani 1 1 d .
H6 H 0.153799 0.472712 0.949972 0.053 Uiso 1 1 calc R
C7 C 0.1239(3) 0.64840(19) 0.91655(12) 0.0440(6) Uani 1 1 d .
H7 H -0.016286 0.639995 0.895584 0.053 Uiso 1 1 calc R
C8 C 0.4242(4) 0.7733(2) 0.94786(13) 0.0517(6) Uani 1 1 d .
H8 H 0.490987 0.850337 0.948544 0.062 Uiso 1 1 calc R
B9 B 0.1059(4) 0.8709(2) 0.87321(15) 0.0425(6) Uani 1 1 d .
C10 C -0.1342(4) 0.9818(2) 0.79015(13) 0.0468(6) Uani 1 1 d .
C11 C 0.0277(3) 1.0715(2) 0.83792(13) 0.0493(6) Uani 1 1 d .
C12 C -0.3573(4) 1.0200(2) 0.78883(16) 0.0693(8) Uani 1 1 d .
H12A H -0.446716 0.961448 0.756468 0.104 Uiso 1 1 calc GR
H12B H -0.378618 1.102181 0.765508 0.104 Uiso 1 1 calc GR
H12C H -0.388715 1.020770 0.843660 0.104 Uiso 1 1 calc GR
C13 C -0.0502(4) 1.1298(2) 0.91189(15) 0.0759(8) Uani 1 1 d .
H13A H -0.115608 1.066494 0.940356 0.114 Uiso 1 1 calc GR
H13B H -0.148755 1.194562 0.893871 0.114 Uiso 1 1 calc GR
H13C H 0.064957 1.164860 0.947947 0.114 Uiso 1 1 calc GR
C14 C 0.1135(4) 1.1704(2) 0.78774(17) 0.0772(9) Uani 1 1 d .
H14A H 0.213227 1.220251 0.822507 0.116 Uiso 1 1 calc GR
H14B H 0.002436 1.223013 0.762375 0.116 Uiso 1 1 calc GR
H14C H 0.179573 1.131213 0.746279 0.116 Uiso 1 1 calc GR
C15 C -0.0900(4) 0.9546(2) 0.70403(15) 0.0809(9) Uani 1 1 d .
H15A H 0.052256 0.929444 0.706468 0.121 Uiso 1 1 calc GR
H15B H -0.115083 1.028647 0.671103 0.121 Uiso 1 1 calc GR
H15C H -0.179499 0.888530 0.680272 0.121 Uiso 1 1 calc GR
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'
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
C7 N1 B9 122.5(2) .
C8 N1 C7 115.17(17) .
C8 N1 B9 122.37(19) .
B9 O2 C10 105.44(17) .
B9 O3 C11 106.15(17) .
C4 C4 C5 124.3(2) 3_667
C4 C4 C6 123.7(2) 3_667
C5 C4 C6 112.07(17) .
C8 C5 C4 123.6(2) .
C7 C6 C4 122.40(19) .
C6 C7 N1 123.6(2) .
C5 C8 N1 123.0(2) .
O2 B9 N1 122.9(2) .
O2 B9 O3 114.79(19) .
O3 B9 N1 122.3(2) .
O2 C10 C11 102.32(16) .
O2 C10 C12 109.19(18) .
O2 C10 C15 106.22(16) .
C12 C10 C11 114.82(19) .
C12 C10 C15 111.0(2) .
C15 C10 C11 112.57(18) .
O3 C11 C10 102.22(17) .
O3 C11 C13 106.34(18) .
O3 C11 C14 108.85(17) .
C13 C11 C10 112.16(18) .
C14 C11 C10 115.76(19) .
C14 C11 C13 110.7(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.399(2) .
N1 C8 1.395(3) .
N1 B9 1.430(3) .
O2 B9 1.360(3) .
O2 C10 1.471(2) .
O3 B9 1.362(3) .
O3 C11 1.462(2) .
C4 C4 1.375(4) 3_667
C4 C5 1.440(3) .
C4 C6 1.457(3) .
C5 C8 1.329(3) .
C6 C7 1.331(3) .
C10 C11 1.549(3) .
C10 C12 1.507(3) .
C10 C15 1.524(3) .
C11 C13 1.527(3) .
C11 C14 1.503(3) .
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
O2 C10 C11 O3 29.60(19) .
O2 C10 C11 C13 -83.9(2) .
O2 C10 C11 C14 147.73(19) .
C4 C4 C5 C8 177.5(2) 3_667
C4 C4 C6 C7 -177.5(2) 3_667
C4 C5 C8 N1 -0.3(4) .
C4 C6 C7 N1 0.4(3) .
C5 C4 C6 C7 2.0(3) .
C6 C4 C5 C8 -2.1(3) .
C7 N1 C8 C5 2.8(3) .
C7 N1 B9 O2 -1.7(3) .
C7 N1 B9 O3 178.54(18) .
C8 N1 C7 C6 -2.8(3) .
C8 N1 B9 O2 178.37(19) .
C8 N1 B9 O3 -1.4(3) .
B9 N1 C7 C6 177.2(2) .
B9 N1 C8 C5 -177.3(2) .
B9 O2 C10 C11 -25.1(2) .
B9 O2 C10 C12 -147.21(19) .
B9 O2 C10 C15 93.1(2) .
B9 O3 C11 C10 -23.7(2) .
B9 O3 C11 C13 94.1(2) .
B9 O3 C11 C14 -146.6(2) .
C10 O2 B9 N1 -168.3(2) .
C10 O2 B9 O3 11.4(2) .
C11 O3 B9 N1 -171.5(2) .
C11 O3 B9 O2 8.8(2) .
C12 C10 C11 O3 147.75(18) .
C12 C10 C11 C13 34.2(3) .
C12 C10 C11 C14 -94.1(2) .
C15 C10 C11 O3 -84.00(19) .
C15 C10 C11 C13 162.47(18) .
C15 C10 C11 C14 34.1(3) .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.559(2)
2 0.441(2)
