data_3b
_audit_creation_date               2019-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'Br, C22 H46 B N2 O'
_chemical_formula_sum              'C22 H46 B Br N2 O'
_chemical_formula_weight           445.33
_chemical_melting_point            ?
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'
 'Br' 'Br' -0.2901 2.4595
 '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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
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                     14.4443(16)
_cell_length_b                     19.364(2)
_cell_length_c                     9.2121(9)
_cell_angle_alpha                  90
_cell_angle_beta                   108.59
_cell_angle_gamma                  90
_cell_volume                       2442.2(4)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9947
_cell_measurement_temperature      170(2)
_cell_measurement_theta_max        27.19
_cell_measurement_theta_min        2.56
_shelx_estimated_absorpt_T_max     0.741
_shelx_estimated_absorpt_T_min     0.396
_exptl_absorpt_coefficient_mu      1.697
_exptl_absorpt_correction_T_max    0.7455
_exptl_absorpt_correction_T_min    0.5879
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1027 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.7886.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'colourless'
_exptl_crystal_density_diffrn      1.211
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         'needle'
_exptl_crystal_F_000               960
_exptl_crystal_size_max            0.67
_exptl_crystal_size_mid            0.225
_exptl_crystal_size_min            0.188
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0584
_diffrn_reflns_av_unetI/netI       0.0365
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.994
_diffrn_reflns_limit_h_max         18
_diffrn_reflns_limit_h_min         -18
_diffrn_reflns_limit_k_max         24
_diffrn_reflns_limit_k_min         -23
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              38493
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.994
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.240
_diffrn_reflns_theta_min           2.559
_diffrn_ambient_temperature        169.99
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.994
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  4439
_reflns_number_total               5443
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.384
_refine_diff_density_min           -0.528
_refine_diff_density_rms           0.056
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       249
_refine_ls_number_reflns           5443
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0425
_refine_ls_R_factor_gt             0.0311
_refine_ls_restrained_S_all        1.035
_refine_ls_shift/su_max            0.003
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0297P)²+0.9078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0720
_refine_ls_wR_factor_ref           0.0767
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4B,H4A), C2(H2A,H2B), C12(H12A,H12B), C19(H19A,H19B), C6(H6A,
 H6B), C16(H16A,H16B), C21(H21B,H21A), C14(H14A,H14B), C13(H13A,H13B), C17(H17A,
 H17B), C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C10(H10A,H10B,H10C), C22(H22A,H22B,
 H22C), C11(H11B,H11C,H11A)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 Br1 Br 0.90127(2) 0.62221(2) 1.24549(2) 0.04132(7) Uani 1 1 d . . . . .
 O002 O 0.52615(8) 0.59673(6) 0.28498(12) 0.0243(2) Uani 1 1 d . . . . .
 N1 N 0.96769(9) 0.61955(6) 0.77057(14) 0.0211(3) Uani 1 1 d . . . . .
 N2 N 0.60601(11) 0.58213(7) 0.11335(16) 0.0288(3) Uani 1 1 d . . . . .
 C5 C 0.37774(11) 0.68410(8) 0.24426(16) 0.0207(3) Uani 1 1 d . . . . .
 H5 H 0.4068 0.7179 0.1890 0.025 Uiso 1 1 calc R . . . .
 C3 C 0.28041(12) 0.68136(8) 0.43935(18) 0.0261(3) Uani 1 1 d . . . . .
 H3A H 0.2606 0.7130 0.5086 0.031 Uiso 1 1 calc R . . . .
 H3B H 0.2213 0.6563 0.3773 0.031 Uiso 1 1 calc R . . . .
 C9 C 0.55087(12) 0.61814(8) 0.17424(18) 0.0252(3) Uani 1 1 d . . . . .
 H9 H 0.5287 0.6623 0.1327 0.030 Uiso 1 1 calc R . . . .
 C4 C 0.31950(12) 0.72479(8) 0.33116(17) 0.0230(3) Uani 1 1 d . . . . .
 H4B H 0.3621 0.7616 0.3920 0.028 Uiso 1 1 calc R . . . .
 H4A H 0.2635 0.7476 0.2550 0.028 Uiso 1 1 calc R . . . .
 C2 C 0.35385(12) 0.62880(8) 0.53689(18) 0.0273(3) Uani 1 1 d . . . . .
 H2A H 0.3177 0.5947 0.5781 0.033 Uiso 1 1 calc R . . . .
 H2B H 0.3995 0.6534 0.6251 0.033 Uiso 1 1 calc R . . . .
 C1 C 0.41452(11) 0.58930(8) 0.45210(17) 0.0226(3) Uani 1 1 d . . . . .
 H1 H 0.4671 0.5630 0.5297 0.027 Uiso 1 1 calc R . . . .
 C12 C 0.54810(11) 0.69502(8) 0.48037(18) 0.0241(3) Uani 1 1 d . . . . .
 H12A H 0.5650 0.7304 0.4156 0.029 Uiso 1 1 calc R . . . .
 H12B H 0.5193 0.7193 0.5503 0.029 Uiso 1 1 calc R . . . .
 C19 C 1.03682(12) 0.63271(9) 0.67784(19) 0.0272(3) Uani 1 1 d . . . . .
 H19A H 1.0010 0.6236 0.5686 0.033 Uiso 1 1 calc R . . . .
 H19B H 1.0550 0.6822 0.6872 0.033 Uiso 1 1 calc R . . . .
 C6 C 0.31373(12) 0.63308(8) 0.12615(18) 0.0258(3) Uani 1 1 d . . . . .
 H6A H 0.2565 0.6584 0.0590 0.031 Uiso 1 1 calc R . . . .
 H6B H 0.3518 0.6161 0.0611 0.031 Uiso 1 1 calc R . . . .
 C16 C 0.87967(11) 0.66641(8) 0.70331(17) 0.0248(3) Uani 1 1 d . . . . .
 H16A H 0.9035 0.7140 0.6987 0.030 Uiso 1 1 calc R . . . .
 H16B H 0.8456 0.6514 0.5969 0.030 Uiso 1 1 calc R . . . .
 C21 C 1.01660(12) 0.63507(9) 0.93841(18) 0.0290(4) Uani 1 1 d . . . . .
 H21B H 0.9701 0.6243 0.9943 0.035 Uiso 1 1 calc R . . . .
 H21A H 1.0734 0.6039 0.9779 0.035 Uiso 1 1 calc R . . . .
 C14 C 0.71236(12) 0.70588(9) 0.69584(19) 0.0297(4) Uani 1 1 d . . . . .
 H14A H 0.6787 0.7239 0.7663 0.036 Uiso 1 1 calc R . . . .
 H14B H 0.7305 0.7458 0.6435 0.036 Uiso 1 1 calc R . . . .
 C13 C 0.64224(12) 0.65986(9) 0.57681(19) 0.0295(4) Uani 1 1 d . . . . .
 H13A H 0.6249 0.6199 0.6299 0.035 Uiso 1 1 calc R . . . .
 H13B H 0.6765 0.6418 0.5073 0.035 Uiso 1 1 calc R . . . .
 C17 C 0.93811(13) 0.54396(8) 0.76189(18) 0.0280(3) Uani 1 1 d . . . . .
 H17A H 0.9974 0.5158 0.8086 0.034 Uiso 1 1 calc R . . . .
 H17B H 0.8943 0.5372 0.8242 0.034 Uiso 1 1 calc R . . . .
 C7 C 0.27674(12) 0.57043(8) 0.19380(19) 0.0286(4) Uani 1 1 d . . . . .
 H7A H 0.2200 0.5849 0.2246 0.034 Uiso 1 1 calc R . . . .
 H7B H 0.2538 0.5349 0.1130 0.034 Uiso 1 1 calc R . . . .
 C8 C 0.35327(12) 0.53780(8) 0.33256(19) 0.0280(3) Uani 1 1 d . . . . .
 H8A H 0.3981 0.5095 0.2953 0.034 Uiso 1 1 calc R . . . .
 H8B H 0.3194 0.5063 0.3838 0.034 Uiso 1 1 calc R . . . .
 C15 C 0.80593(12) 0.66803(10) 0.78993(19) 0.0320(4) Uani 1 1 d . . . . .
 H15A H 0.8348 0.6918 0.8892 0.038 Uiso 1 1 calc R . . . .
 H15B H 0.7896 0.6202 0.8111 0.038 Uiso 1 1 calc R . . . .
 C20 C 1.12953(13) 0.59022(10) 0.7235(2) 0.0334(4) Uani 1 1 d . . . . .
 H20A H 1.1677 0.6012 0.6557 0.050 Uiso 1 1 calc GR . . . .
 H20B H 1.1128 0.5410 0.7149 0.050 Uiso 1 1 calc GR . . . .
 H20C H 1.1681 0.6009 0.8296 0.050 Uiso 1 1 calc GR . . . .
 C18 C 0.88742(14) 0.51712(10) 0.6026(2) 0.0383(4) Uani 1 1 d . . . . .
 H18A H 0.9273 0.5273 0.5369 0.057 Uiso 1 1 calc GR . . . .
 H18B H 0.8236 0.5396 0.5608 0.057 Uiso 1 1 calc GR . . . .
 H18C H 0.8784 0.4671 0.6067 0.057 Uiso 1 1 calc GR . . . .
 C10 C 0.63411(17) 0.60749(10) -0.0160(2) 0.0439(5) Uani 1 1 d . . . . .
 H10A H 0.6021 0.6519 -0.0504 0.066 Uiso 1 1 calc GR . . . .
 H10B H 0.6140 0.5741 -0.1002 0.066 Uiso 1 1 calc GR . . . .
 H10C H 0.7051 0.6135 0.0157 0.066 Uiso 1 1 calc GR . . . .
 C22 C 1.05116(15) 0.70852(10) 0.9740(2) 0.0454(5) Uani 1 1 d . . . . .
 H22A H 1.0997 0.7192 0.9235 0.068 Uiso 1 1 calc GR . . . .
 H22B H 1.0807 0.7140 1.0850 0.068 Uiso 1 1 calc GR . . . .
 H22C H 0.9955 0.7400 0.9368 0.068 Uiso 1 1 calc GR . . . .
 C11 C 0.64777(18) 0.51643(11) 0.1787(3) 0.0530(6) Uani 1 1 d . . . . .
 H11B H 0.7192 0.5199 0.2145 0.079 Uiso 1 1 calc GR . . . .
 H11C H 0.6274 0.4803 0.1006 0.079 Uiso 1 1 calc GR . . . .
 H11A H 0.6249 0.5049 0.2652 0.079 Uiso 1 1 calc GR . . . .
 B1 B 0.46574(13) 0.64472(9) 0.37066(19) 0.0207(3) 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
 O002 C9 1.2539(19) . ?
 O002 B1 1.6393(19) . ?
 N1 C19 1.528(2) . ?
 N1 C16 1.5237(19) . ?
 N1 C21 1.5111(19) . ?
 N1 C17 1.520(2) . ?
 N2 C9 1.312(2) . ?
 N2 C10 1.461(2) . ?
 N2 C11 1.454(2) . ?
 C5 C4 1.549(2) . ?
 C5 C6 1.541(2) . ?
 C5 B1 1.615(2) . ?
 C3 C4 1.542(2) . ?
 C3 C2 1.536(2) . ?
 C2 C1 1.549(2) . ?
 C1 C8 1.539(2) . ?
 C1 B1 1.617(2) . ?
 C12 C13 1.527(2) . ?
 C12 B1 1.618(2) . ?
 C19 C20 1.513(2) . ?
 C6 C7 1.536(2) . ?
 C16 C15 1.521(2) . ?
 C21 C22 1.509(2) . ?
 C14 C13 1.521(2) . ?
 C14 C15 1.539(2) . ?
 C17 C18 1.508(2) . ?
 C7 C8 1.534(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
 C9 O002 B1 122.53(12) . . ?
 C16 N1 C19 106.42(11) . . ?
 C21 N1 C19 111.30(12) . . ?
 C21 N1 C16 110.78(12) . . ?
 C21 N1 C17 106.10(12) . . ?
 C17 N1 C19 110.74(12) . . ?
 C17 N1 C16 111.60(12) . . ?
 C9 N2 C10 122.32(14) . . ?
 C9 N2 C11 121.09(15) . . ?
 C11 N2 C10 116.47(15) . . ?
 C4 C5 B1 107.45(12) . . ?
 C6 C5 C4 112.88(13) . . ?
 C6 C5 B1 111.31(12) . . ?
 C2 C3 C4 114.36(13) . . ?
 O002 C9 N2 122.78(15) . . ?
 C3 C4 C5 115.32(12) . . ?
 C3 C2 C1 115.36(13) . . ?
 C2 C1 B1 108.80(12) . . ?
 C8 C1 C2 113.09(13) . . ?
 C8 C1 B1 109.98(12) . . ?
 C13 C12 B1 115.84(13) . . ?
 C20 C19 N1 115.59(13) . . ?
 C7 C6 C5 115.35(13) . . ?
 C15 C16 N1 115.60(13) . . ?
 C22 C21 N1 115.12(14) . . ?
 C13 C14 C15 112.97(14) . . ?
 C14 C13 C12 115.02(13) . . ?
 C18 C17 N1 115.11(13) . . ?
 C8 C7 C6 114.33(13) . . ?
 C7 C8 C1 115.23(13) . . ?
 C16 C15 C14 110.52(14) . . ?
 C5 B1 O002 109.75(11) . . ?
 C5 B1 C1 106.05(13) . . ?
 C5 B1 C12 114.76(13) . . ?
 C1 B1 O002 103.86(11) . . ?
 C1 B1 C12 117.62(13) . . ?
 C12 B1 O002 104.11(12) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
