# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_mf_mjp_gly
_database_code_depnum_ccdc_archive 'CCDC 1997970'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Department of Chemistry, University of Wroclaw
Poland
;
_audit_update_record             
;
2020-04-20 deposited with the CCDC.	2020-06-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_mf_mjp_gly          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.813 Why?
RESPONSE: The overall quality of the data was low and caused by the crystal quality. 
;
# Added during the CSD deposition process: Monday 20 April 2020 11:05 AM
# end Validation Reply Form

_audit_creation_date             2020-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 B F2 N3 O2'
_chemical_formula_sum            'C12 H12 B F2 N3 O2'
_chemical_formula_weight         279.06
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.1383(6)
_cell_length_b                   20.8629(14)
_cell_length_c                   8.3699(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1246.49(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1654
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9730
_cell_measurement_theta_min      3.0020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2433
_exptl_crystal_size_mid          0.1222
_exptl_crystal_size_min          0.0791
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1317
_diffrn_reflns_av_unetI/netI     0.1469
_diffrn_reflns_Laue_measured_fraction_full 0.813
_diffrn_reflns_Laue_measured_fraction_max 0.812
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8372
_diffrn_reflns_point_group_measured_fraction_full 0.771
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_theta_full        29.984
_diffrn_reflns_theta_max         29.984
_diffrn_reflns_theta_min         3.016
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.813
_diffrn_measured_fraction_theta_max 0.812
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   60.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000    0.0000 153

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   60.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000   90.0000 153

#__ type_ start__ end____ width___ exp.time_
  3 omega  -54.00   60.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000  180.0000 153

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00   60.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000  270.0000 153

#__ type_ start__ end____ width___ exp.time_
  5 omega  -54.00  -30.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000  -79.0000   45.0000 31
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0289179000
_diffrn_orient_matrix_UB_12      -0.0053928000
_diffrn_orient_matrix_UB_13      -0.0799658000
_diffrn_orient_matrix_UB_21      0.0364002000
_diffrn_orient_matrix_UB_22      0.0303544000
_diffrn_orient_matrix_UB_23      -0.0223083000
_diffrn_orient_matrix_UB_31      0.0877834000
_diffrn_orient_matrix_UB_32      -0.0143418000
_diffrn_orient_matrix_UB_33      -0.0170928000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.724
_reflns_Friedel_fraction_max     0.724
_reflns_number_gt                1719
_reflns_number_total             2790
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.271
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.7(10)
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0754
_refine_ls_restrained_S_all      1.003
_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)+(0.0467P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1707
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I)
2.c Idealised Me refined as rotating group:
 C00J(H00E,H00J,H00K)
;
_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
F001 F 0.2950(5) 0.07341(16) 0.6755(5) 0.0354(10) Uani 1 1 d . . . . .
F002 F 0.6001(5) 0.08674(16) 0.7356(5) 0.0344(10) Uani 1 1 d . . . . .
O003 O 0.5419(6) 0.4511(2) 0.2773(6) 0.0289(11) Uani 1 1 d . . . . .
O004 O 0.5755(6) 0.3627(2) 0.1267(5) 0.0307(11) Uani 1 1 d . . . . .
N005 N 0.4091(6) 0.1811(2) 0.7049(6) 0.0229(12) Uani 1 1 d . . . . .
N006 N 0.5242(6) 0.2850(2) 0.3693(6) 0.0223(12) Uani 1 1 d . . . . .
H006 H 0.559351 0.276666 0.273241 0.027 Uiso 1 1 calc R . . . .
N007 N 0.4970(7) 0.1164(2) 0.4716(7) 0.0226(12) Uani 1 1 d . . . . .
C008 C 0.4944(8) 0.2339(3) 0.4593(7) 0.0170(13) Uani 1 1 d . . . . .
C009 C 0.5186(8) 0.1730(3) 0.3862(8) 0.0185(13) Uani 1 1 d . . . . .
C00A C 0.5076(8) 0.3527(3) 0.4058(7) 0.0204(14) Uani 1 1 d . . . . .
H00A H 0.597798 0.364888 0.486955 0.024 Uiso 1 1 calc R . . . .
H00B H 0.382817 0.362346 0.444875 0.024 Uiso 1 1 calc R . . . .
C00B C 0.4412(8) 0.2381(3) 0.6230(7) 0.0211(14) Uani 1 1 d . . . . .
C00C C 0.5621(8) 0.1573(3) 0.2289(8) 0.0233(14) Uani 1 1 d . . . . .
H00C H 0.583236 0.186038 0.145797 0.028 Uiso 1 1 calc R . . . .
C00D C 0.5270(8) 0.0665(3) 0.3700(9) 0.0282(16) Uani 1 1 d . . . . .
H00D H 0.520824 0.023380 0.397636 0.034 Uiso 1 1 calc R . . . .
C00E C 0.5450(8) 0.3882(3) 0.2536(8) 0.0220(14) Uani 1 1 d . . . . .
C00F C 0.5683(8) 0.0898(3) 0.2190(9) 0.0289(15) Uani 1 1 d . . . . .
H00F H 0.594942 0.065589 0.128444 0.035 Uiso 1 1 calc R . . . .
C00G C 0.3493(9) 0.2633(3) 0.8715(8) 0.0284(15) Uani 1 1 d . . . . .
H00G H 0.315410 0.285907 0.962874 0.034 Uiso 1 1 calc R . . . .
C00H C 0.4046(8) 0.2898(3) 0.7266(7) 0.0254(14) Uani 1 1 d . . . . .
H00H H 0.415308 0.333218 0.702777 0.030 Uiso 1 1 calc R . . . .
C00I C 0.3538(9) 0.1970(3) 0.8554(8) 0.0288(16) Uani 1 1 d . . . . .
H00I H 0.323569 0.167865 0.935411 0.035 Uiso 1 1 calc R . . . .
C00J C 0.5706(9) 0.4898(3) 0.1336(9) 0.0363(18) Uani 1 1 d . . . . .
H00E H 0.471635 0.481464 0.058802 0.054 Uiso 1 1 calc GR . . . .
H00J H 0.688778 0.478920 0.086096 0.054 Uiso 1 1 calc GR . . . .
H00K H 0.570203 0.534411 0.161742 0.054 Uiso 1 1 calc GR . . . .
B00K B 0.4504(10) 0.1119(3) 0.6491(9) 0.0241(17) 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
F001 B00K 1.387(7) . ?
F002 B00K 1.393(7) . ?
O003 C00E 1.327(7) . ?
O003 C00J 1.463(8) . ?
O004 C00E 1.208(8) . ?
N005 C00B 1.391(7) . ?
N005 C00I 1.361(8) . ?
N005 B00K 1.546(9) . ?
N006 H006 0.8600 . ?
N006 C008 1.322(7) . ?
N006 C00A 1.450(8) . ?
N007 C009 1.388(7) . ?
N007 C00D 1.362(8) . ?
N007 B00K 1.525(9) . ?
C008 C009 1.422(8) . ?
C008 C00B 1.424(8) . ?
C009 C00C 1.391(9) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00E 1.497(8) . ?
C00B C00H 1.410(8) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.413(9) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.386(10) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00H 1.390(9) . ?
C00G C00I 1.391(9) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J H00E 0.9600 . ?
C00J H00J 0.9600 . ?
C00J H00K 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
C00E O003 C00J 114.9(5) . . ?
C00B N005 B00K 128.2(5) . . ?
C00I N005 C00B 107.2(5) . . ?
C00I N005 B00K 124.2(5) . . ?
C008 N006 H006 114.7 . . ?
C008 N006 C00A 130.7(5) . . ?
C00A N006 H006 114.7 . . ?
C009 N007 B00K 125.4(5) . . ?
C00D N007 C009 108.1(5) . . ?
C00D N007 B00K 126.6(6) . . ?
N006 C008 C009 117.1(5) . . ?
N006 C008 C00B 122.8(5) . . ?
C009 C008 C00B 120.0(5) . . ?
N007 C009 C008 121.7(5) . . ?
N007 C009 C00C 108.3(5) . . ?
C00C C009 C008 130.1(6) . . ?
N006 C00A H00A 110.4 . . ?
N006 C00A H00B 110.4 . . ?
N006 C00A C00E 106.8(5) . . ?
H00A C00A H00B 108.6 . . ?
C00E C00A H00A 110.4 . . ?
C00E C00A H00B 110.4 . . ?
N005 C00B C008 117.8(5) . . ?
N005 C00B C00H 108.7(5) . . ?
C00H C00B C008 133.5(6) . . ?
C009 C00C H00C 126.4 . . ?
C009 C00C C00F 107.2(6) . . ?
C00F C00C H00C 126.4 . . ?
N007 C00D H00D 125.2 . . ?
N007 C00D C00F 109.6(6) . . ?
C00F C00D H00D 125.2 . . ?
O003 C00E C00A 111.0(5) . . ?
O004 C00E O003 124.7(6) . . ?
O004 C00E C00A 124.2(6) . . ?
C00C C00F H00F 126.6 . . ?
C00D C00F C00C 106.8(6) . . ?
C00D C00F H00F 126.6 . . ?
C00H C00G H00G 126.1 . . ?
C00H C00G C00I 107.7(6) . . ?
C00I C00G H00G 126.1 . . ?
C00B C00H H00H 126.7 . . ?
C00G C00H C00B 106.6(6) . . ?
C00G C00H H00H 126.7 . . ?
N005 C00I C00G 109.8(6) . . ?
N005 C00I H00I 125.1 . . ?
C00G C00I H00I 125.1 . . ?
O003 C00J H00E 109.5 . . ?
O003 C00J H00J 109.5 . . ?
O003 C00J H00K 109.5 . . ?
H00E C00J H00J 109.5 . . ?
H00E C00J H00K 109.5 . . ?
H00J C00J H00K 109.5 . . ?
F001 B00K F002 108.2(5) . . ?
F001 B00K N005 109.9(5) . . ?
F001 B00K N007 111.4(6) . . ?
F002 B00K N005 110.0(5) . . ?
F002 B00K N007 111.2(5) . . ?
N007 B00K N005 106.1(5) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6 24 2 0.0747 -5.5461 23.8943 2.2690 -0.1499 0.4728 -0.8683
2 -23 -7 0.0450 2.1065 -22.9503 -6.9566 0.6191 -0.4648 0.6330
-9 12 3 0.0864 -8.8661 12.4381 2.5293 -0.0129 -0.0016 -0.9999
4 13 9 0.0595 4.3512 12.5700 9.3680 -0.9427 0.3310 0.0416
3 -4 -11 0.0586 3.1150 -3.6636 -11.1229 0.8191 0.2503 0.5161
3 -14 10 0.0498 2.7920 -14.0545 9.8330 -0.7913 -0.5443 0.2786
4 13 -9 0.0759 4.1681 12.7085 -9.4491 0.5665 0.7483 0.3451
2 -21 8 0.0522 1.6096 -20.9034 8.0806 -0.5800 -0.7562 0.3030
0 20 -9 0.0600 -0.0843 19.5515 -8.8107 0.6016 0.7870 -0.1372
-1 29 -2 0.0645 -1.4838 28.7757 -1.7101 0.0245 0.8576 -0.5137
1 29 1 0.0710 1.1507 29.1160 0.9679 -0.2677 0.9041 -0.3331
9 10 5 0.0836 8.5198 10.2186 4.7602 -0.6821 0.5141 0.5200
-2 -22 -7 0.0461 -1.6863 -22.4965 -7.3388 0.7569 -0.5805 0.3000
-2 -16 -10 0.0377 -1.5044 -15.9545 -9.7540 0.9095 -0.3215 0.2635
0 17 10 0.0413 0.3120 16.9072 9.6482 -0.8717 0.3093 -0.3800
-1 -7 -11 0.0350 -1.4295 -7.3887 -11.2965 0.9845 -0.0243 0.1736
-2 11 11 0.0412 -1.5479 10.6415 10.8494 -0.8802 0.0246 -0.4739
0 9 11 0.0346 -0.1955 9.2784 11.1941 -0.9395 0.0248 -0.3416
3 -26 4 0.0554 2.7481 -26.3008 4.1851 -0.2723 -0.7917 0.5469
-2 26 -4 0.0655 -2.4609 26.3585 -4.3675 0.2783 0.8080 -0.5194

_olex2_submission_special_instructions 'No special instructions were received'
