data_mjr18062_0m
_audit_creation_date               2018-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
_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           'C16 H27 B O4'
_chemical_formula_sum              'C16 H27 B O4'
_chemical_formula_weight           294.18
_chemical_absolute_configuration   rmad
_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' 0.0148 0.0070 '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' 0.0073 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0412 0.0250 '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             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     6.2022(2)
_cell_length_b                     12.0562(5)
_cell_length_c                     11.3655(4)
_cell_angle_alpha                  90
_cell_angle_beta                   92.957(2)
_cell_angle_gamma                  90
_cell_volume                       848.72(5)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      5924
_cell_measurement_temperature      296(2)
_cell_measurement_theta_max        54.59
_cell_measurement_theta_min        9.344
_shelx_estimated_absorpt_T_max     0.980
_shelx_estimated_absorpt_T_min     0.941
_exptl_absorpt_coefficient_mu      0.411
_exptl_absorpt_correction_T_max    0.7508
_exptl_absorpt_correction_T_min    0.4972
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1598 before and 0.0622 after correction. The Ratio of minimum to maximum transmission is 0.6622. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'colourless'
_exptl_crystal_density_diffrn      1.151
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         'block'
_exptl_crystal_F_000               320
_exptl_crystal_size_max            0.15
_exptl_crystal_size_mid            0.1
_exptl_crystal_size_min            0.05
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0408
_diffrn_reflns_av_unetI/netI       0.0419
_diffrn_reflns_Laue_measured_fraction_full  0.972
_diffrn_reflns_Laue_measured_fraction_max  0.973
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         14
_diffrn_reflns_limit_k_min         -14
_diffrn_reflns_limit_l_max         13
_diffrn_reflns_limit_l_min         -13
_diffrn_reflns_number              9311
_diffrn_reflns_point_group_measured_fraction_full  0.967
_diffrn_reflns_point_group_measured_fraction_max  0.966
_diffrn_reflns_theta_full          53.594
_diffrn_reflns_theta_max           54.965
_diffrn_reflns_theta_min           9.341
_diffrn_ambient_temperature        296
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.972
_diffrn_measured_fraction_theta_max  0.973
_diffrn_measurement_device_type    'Bruker D8 Venture'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             GaK\a
_diffrn_radiation_wavelength       1.34139
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.889
_reflns_Friedel_fraction_full      0.961
_reflns_Friedel_fraction_max       0.958
_reflns_number_gt                  2725
_reflns_number_total               3123
_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 v8.37A (Bruker, 2015)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.596
_refine_diff_density_min           -0.249
_refine_diff_density_rms           0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1084 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.05(14)
_refine_ls_extinction_coef         0.09(2)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       197
_refine_ls_number_reflns           3123
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0893
_refine_ls_R_factor_gt             0.0811
_refine_ls_restrained_S_all        1.029
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.1100P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.2034
_refine_ls_wR_factor_ref           0.2113
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
 O1 O 0.3085(7) 0.4229(3) 0.5240(3) 0.0675(12) Uani 1 1 d . . . . .
 O2 O -0.0363(8) 0.7839(4) 0.6153(4) 0.0844(15) Uani 1 1 d . . . . .
 H2 H -0.126412 0.815103 0.571644 0.127 Uiso 1 1 calc GR . . . .
 O3 O 0.6838(11) 0.3655(5) 0.8608(6) 0.112(2) Uani 1 1 d . . . . .
 O4 O 0.9060(9) 0.4971(4) 0.9319(5) 0.0938(18) Uani 1 1 d . . . . .
 C1 C 0.3382(8) 0.5291(4) 0.4678(4) 0.0483(11) Uani 1 1 d . . . . .
 C2 C 0.4426(7) 0.6040(4) 0.5640(4) 0.0438(11) Uani 1 1 d . . . . .
 H2A H 0.545568 0.654198 0.528801 0.053 Uiso 1 1 calc R . . . .
 C3 C 0.5664(8) 0.5191(4) 0.6429(4) 0.0450(11) Uani 1 1 d . . . . .
 H3 H 0.695855 0.496832 0.602969 0.054 Uiso 1 1 calc R . . . .
 C4 C 0.4122(9) 0.4227(4) 0.6386(4) 0.0547(12) Uani 1 1 d . . . . .
 H4A H 0.489667 0.353681 0.652695 0.066 Uiso 1 1 calc R . . . .
 H4B H 0.306720 0.430961 0.698144 0.066 Uiso 1 1 calc R . . . .
 C5 C 0.1181(8) 0.5696(5) 0.4212(4) 0.0562(13) Uani 1 1 d . . . . .
 H5 H 0.040915 0.525189 0.367010 0.067 Uiso 1 1 calc R . . . .
 C6 C 0.0316(8) 0.6618(5) 0.4522(5) 0.0600(14) Uani 1 1 d . . . . .
 H6 H -0.098563 0.683006 0.414506 0.072 Uiso 1 1 calc R . . . .
 C7 C 0.1303(9) 0.7364(4) 0.5458(5) 0.0549(13) Uani 1 1 d . . . . .
 H7 H 0.211093 0.795935 0.509135 0.066 Uiso 1 1 calc R . . . .
 C8 C 0.2790(9) 0.6715(4) 0.6286(4) 0.0507(12) Uani 1 1 d . . . . .
 H8A H 0.193952 0.621921 0.674883 0.061 Uiso 1 1 calc R . . . .
 H8B H 0.354899 0.722284 0.682337 0.061 Uiso 1 1 calc R . . . .
 C9 C 0.6377(9) 0.5591(4) 0.7676(4) 0.0539(12) Uani 1 1 d . . . . .
 H9A H 0.511697 0.587419 0.804802 0.065 Uiso 1 1 calc R . . . .
 H9B H 0.736927 0.620555 0.760093 0.065 Uiso 1 1 calc R . . . .
 C10 C 0.9275(10) 0.4010(6) 1.0132(5) 0.0718(16) Uani 1 1 d . . . . .
 C11 C 0.7933(17) 0.4307(9) 1.1185(6) 0.108(3) Uani 1 1 d . . . . .
 H11A H 0.873757 0.480668 1.169746 0.162 Uiso 1 1 calc GR . . . .
 H11B H 0.761087 0.364352 1.160967 0.162 Uiso 1 1 calc GR . . . .
 H11C H 0.661092 0.465488 1.090726 0.162 Uiso 1 1 calc GR . . . .
 C12 C 1.1605(13) 0.3997(9) 1.0536(9) 0.114(3) Uani 1 1 d . . . . .
 H12A H 1.247485 0.389568 0.986971 0.170 Uiso 1 1 calc GR . . . .
 H12B H 1.186259 0.339938 1.108293 0.170 Uiso 1 1 calc GR . . . .
 H12C H 1.197383 0.468830 1.091440 0.170 Uiso 1 1 calc GR . . . .
 C13 C 0.8390(12) 0.3081(5) 0.9387(6) 0.080(2) Uani 1 1 d . . . . .
 C14 C 0.7114(15) 0.2224(7) 1.0076(9) 0.098(2) Uani 1 1 d . . . . .
 H14A H 0.582996 0.256432 1.034678 0.147 Uiso 1 1 calc GR . . . .
 H14B H 0.799102 0.196447 1.074018 0.147 Uiso 1 1 calc GR . . . .
 H14C H 0.672385 0.161041 0.957111 0.147 Uiso 1 1 calc GR . . . .
 C15 C 1.023(2) 0.2524(8) 0.8681(8) 0.130(4) Uani 1 1 d . . . . .
 H15A H 0.964797 0.190583 0.823847 0.195 Uiso 1 1 calc GR . . . .
 H15B H 1.136376 0.227073 0.922398 0.195 Uiso 1 1 calc GR . . . .
 H15C H 1.080393 0.305723 0.815305 0.195 Uiso 1 1 calc GR . . . .
 C16 C 0.4831(11) 0.5100(6) 0.3657(5) 0.0724(17) Uani 1 1 d . . . . .
 H16A H 0.623332 0.486654 0.395713 0.109 Uiso 1 1 calc GR . . . .
 H16B H 0.496051 0.577628 0.322123 0.109 Uiso 1 1 calc GR . . . .
 H16C H 0.421173 0.453514 0.314844 0.109 Uiso 1 1 calc GR . . . .
 B1 B 0.7482(9) 0.4713(5) 0.8514(5) 0.0484(12) 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 C1 1.446(6) . ?
 O1 C4 1.423(6) . ?
 O2 H2 0.8200 . ?
 O2 C7 1.451(7) . ?
 O3 C13 1.450(8) . ?
 O3 B1 1.342(8) . ?
 O4 C10 1.483(8) . ?
 O4 B1 1.342(7) . ?
 C1 C2 1.535(6) . ?
 C1 C5 1.519(7) . ?
 C1 C16 1.521(8) . ?
 C2 H2A 0.9800 . ?
 C2 C3 1.540(6) . ?
 C2 C8 1.519(7) . ?
 C3 H3 0.9800 . ?
 C3 C4 1.504(7) . ?
 C3 C9 1.540(6) . ?
 C4 H4A 0.9700 . ?
 C4 H4B 0.9700 . ?
 C5 H5 0.9300 . ?
 C5 C6 1.291(9) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.500(8) . ?
 C7 H7 0.9800 . ?
 C7 C8 1.503(6) . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C9 B1 1.559(7) . ?
 C10 C11 1.535(10) . ?
 C10 C12 1.494(10) . ?
 C10 C13 1.491(10) . ?
 C11 H11A 0.9600 . ?
 C11 H11B 0.9600 . ?
 C11 H11C 0.9600 . ?
 C12 H12A 0.9600 . ?
 C12 H12B 0.9600 . ?
 C12 H12C 0.9600 . ?
 C13 C14 1.540(10) . ?
 C13 C15 1.579(13) . ?
 C14 H14A 0.9600 . ?
 C14 H14B 0.9600 . ?
 C14 H14C 0.9600 . ?
 C15 H15A 0.9600 . ?
 C15 H15B 0.9600 . ?
 C15 H15C 0.9600 . ?
 C16 H16A 0.9600 . ?
 C16 H16B 0.9600 . ?
 C16 H16C 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
 C4 O1 C1 110.1(4) . . ?
 C7 O2 H2 109.5 . . ?
 B1 O3 C13 108.1(5) . . ?
 B1 O4 C10 106.4(5) . . ?
 O1 C1 C2 105.4(3) . . ?
 O1 C1 C5 107.8(4) . . ?
 O1 C1 C16 107.2(5) . . ?
 C5 C1 C2 113.4(4) . . ?
 C5 C1 C16 109.8(4) . . ?
 C16 C1 C2 112.9(4) . . ?
 C1 C2 H2A 109.4 . . ?
 C1 C2 C3 101.7(4) . . ?
 C3 C2 H2A 109.4 . . ?
 C8 C2 C1 113.0(4) . . ?
 C8 C2 H2A 109.4 . . ?
 C8 C2 C3 113.6(4) . . ?
 C2 C3 H3 108.0 . . ?
 C2 C3 C9 116.0(4) . . ?
 C4 C3 C2 101.4(4) . . ?
 C4 C3 H3 108.0 . . ?
 C4 C3 C9 115.0(4) . . ?
 C9 C3 H3 108.0 . . ?
 O1 C4 C3 106.5(4) . . ?
 O1 C4 H4A 110.4 . . ?
 O1 C4 H4B 110.4 . . ?
 C3 C4 H4A 110.4 . . ?
 C3 C4 H4B 110.4 . . ?
 H4A C4 H4B 108.6 . . ?
 C1 C5 H5 118.0 . . ?
 C6 C5 C1 124.1(5) . . ?
 C6 C5 H5 118.0 . . ?
 C5 C6 H6 118.3 . . ?
 C5 C6 C7 123.3(5) . . ?
 C7 C6 H6 118.3 . . ?
 O2 C7 C6 110.3(5) . . ?
 O2 C7 H7 109.7 . . ?
 O2 C7 C8 107.2(4) . . ?
 C6 C7 H7 109.7 . . ?
 C6 C7 C8 110.3(4) . . ?
 C8 C7 H7 109.7 . . ?
 C2 C8 H8A 109.1 . . ?
 C2 C8 H8B 109.1 . . ?
 C7 C8 C2 112.3(4) . . ?
 C7 C8 H8A 109.1 . . ?
 C7 C8 H8B 109.1 . . ?
 H8A C8 H8B 107.9 . . ?
 C3 C9 H9A 108.2 . . ?
 C3 C9 H9B 108.2 . . ?
 C3 C9 B1 116.5(4) . . ?
 H9A C9 H9B 107.3 . . ?
 B1 C9 H9A 108.2 . . ?
 B1 C9 H9B 108.2 . . ?
 O4 C10 C11 105.6(6) . . ?
 O4 C10 C12 104.7(6) . . ?
 O4 C10 C13 102.4(4) . . ?
 C12 C10 C11 108.5(7) . . ?
 C13 C10 C11 114.8(7) . . ?
 C13 C10 C12 119.2(7) . . ?
 C10 C11 H11A 109.5 . . ?
 C10 C11 H11B 109.5 . . ?
 C10 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?
 C10 C12 H12A 109.5 . . ?
 C10 C12 H12B 109.5 . . ?
 C10 C12 H12C 109.5 . . ?
 H12A C12 H12B 109.5 . . ?
 H12A C12 H12C 109.5 . . ?
 H12B C12 H12C 109.5 . . ?
 O3 C13 C10 101.6(5) . . ?
 O3 C13 C14 106.8(6) . . ?
 O3 C13 C15 111.6(7) . . ?
 C10 C13 C14 113.5(7) . . ?
 C10 C13 C15 110.7(7) . . ?
 C14 C13 C15 112.2(7) . . ?
 C13 C14 H14A 109.5 . . ?
 C13 C14 H14B 109.5 . . ?
 C13 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?
 C13 C15 H15A 109.5 . . ?
 C13 C15 H15B 109.5 . . ?
 C13 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?
 C1 C16 H16A 109.5 . . ?
 C1 C16 H16B 109.5 . . ?
 C1 C16 H16C 109.5 . . ?
 H16A C16 H16B 109.5 . . ?
 H16A C16 H16C 109.5 . . ?
 H16B C16 H16C 109.5 . . ?
 O3 B1 C9 124.8(5) . . ?
 O4 B1 O3 112.1(5) . . ?
 O4 B1 C9 122.8(5) . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
 O2 H2 O1 0.82 2.01 2.810(5) 166.8 2_556

_olex2_submission_special_instructions  'No special instructions were received'
