# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1949478'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;The Australian National University
Australia
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
Hydrogen atoms were visible in the Fourier difference map. The N-H and O-H
protons were refined with restraints on bond lengths and angles. The  C-H
protons were initially refined with restraints on bond lengths and angles, 
after which the positions were used as the basis for a riding model. 

Apart from restraints on N-H and O-H bond lengths and angles, it was not 
necessary to use any crystallographic restraints.
;

_cell_length_a                   14.533300(16)
_cell_length_b                   14.533300(16)
_cell_length_c                   7.836020(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1655.099(5)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 42/n '
_symmetry_space_group_name_Hall  '-P 4bc'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
y+1/2,-x,z+1/2
-y+1/2,x,-z+1/2
x+1/2,y+1/2,-z
-x+1/2,-y+1/2,z
-y,x+1/2,z+1/2
y,-x+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

_chemical_formula_sum            'C33 H44 N8 O4'
_chemical_formula_moiety         'C29 H28 N8, 4(C H4 O)'
_chemical_compound_source        synthesized
_chemical_formula_weight         616.76


_cell_measurement_reflns_used    3773
_cell_measurement_theta_min      6.08
_cell_measurement_theta_max      73.4
_cell_measurement_temperature    150

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_max          0.58

_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    0.676

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction Supernova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            8618
_diffrn_reflns_av_unetI/netI     0.008
_reflns_number_total             1665
_diffrn_reflns_av_R_equivalents  0.031

_diffrn_reflns_theta_min         4.302
_diffrn_reflns_theta_max         73.803
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        72.327
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   2.19
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.23
_refine_diff_density_max         0.39

# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     11
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1635
_oxford_refine_ls_R_factor_ref   0.0511
_refine_ls_wR_factor_ref         0.1348
_refine_ls_goodness_of_fit_ref   1.0161
_refine_ls_shift/su_max          0.0003060
_refine_ls_shift/su_mean         0.0000326

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1635
_refine_ls_R_factor_all          0.0511
_refine_ls_wR_factor_all         0.1348

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1588
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_gt          0.1326

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 1.18P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N2 N 0.50424(11) 0.52541(10) 0.81131(18) 0.0350 1.0000 Uani D . . . . .
N1 N 0.43225(11) 0.66908(12) 0.8270(2) 0.0393 1.0000 Uani D . . . . .
C3 C 0.49481(11) 0.61017(11) 0.76396(19) 0.0263 1.0000 Uani D . . . . .
C4 C 0.55719(10) 0.64633(10) 0.62840(17) 0.0211 1.0000 Uani . . . . . .
C5 C 0.57726(10) 0.74007(10) 0.61540(18) 0.0226 1.0000 Uani . . . . . .
C6 C 0.63607(10) 0.77171(10) 0.49003(18) 0.0204 1.0000 Uani . . . . . .
C7 C 0.67655(9) 0.71140(9) 0.37269(17) 0.0172 1.0000 Uani . . . . . .
C8 C 0.65638(10) 0.61800(9) 0.38674(18) 0.0204 1.0000 Uani . . . . . .
C9 C 0.59737(10) 0.58598(10) 0.51347(19) 0.0225 1.0000 Uani . . . . . .
C10 C 0.7500 0.7500 0.2500 0.0165 1.0000 Uani S T . . . .
O101 O 0.63928(9) 0.39000(9) 0.81605(17) 0.0384 1.0000 Uani D . . . . .
C102 C 0.61035(16) 0.31348(14) 0.7203(3) 0.0511 1.0000 Uani . . . . . .
H51 H 0.5495 0.7814 0.6930 0.0280 1.0000 Uiso R . . . . .
H61 H 0.6498 0.8347 0.4834 0.0256 1.0000 Uiso R . . . . .
H81 H 0.6838 0.5762 0.3090 0.0244 1.0000 Uiso R . . . . .
H91 H 0.5833 0.5213 0.5209 0.0283 1.0000 Uiso R . . . . .
H12 H 0.4272(15) 0.7263(12) 0.785(3) 0.0473(19) 1.0000 Uiso D . . . . .
H11 H 0.3994(14) 0.6502(13) 0.912(3) 0.0481(19) 1.0000 Uiso D . . . . .
H21 H 0.4600(12) 0.5070(13) 0.886(3) 0.0421(19) 1.0000 Uiso D . . . . .
H1011 H 0.5928(15) 0.4284(16) 0.809(4) 0.060(2) 1.0000 Uiso D . . . . .
H1021 H 0.6404 0.2609 0.7665 0.0759 1.0000 Uiso R . . . . .
H1022 H 0.5443 0.3047 0.7263 0.0758 1.0000 Uiso R . . . . .
H1023 H 0.6296 0.3213 0.6021 0.0761 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          9.0(6)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N2 . C3 . 1.294(2) yes
N2 . H21 . 0.907(15) no
N1 . C3 . 1.343(2) yes
N1 . H12 . 0.899(16) no
N1 . H11 . 0.864(16) no
C3 . C4 . 1.492(2) yes
C4 . C5 . 1.397(2) yes
C4 . C9 . 1.386(2) yes
C5 . C6 . 1.381(2) yes
C5 . H51 . 0.945 no
C6 . C7 . 1.4000(19) yes
C6 . H61 . 0.938 no
C7 . C8 . 1.3930(19) yes
C7 . C10 . 1.5422(13) yes
C8 . C9 . 1.392(2) yes
C8 . H81 . 0.948 no
C9 . H91 . 0.963 no
O101 . C102 . 1.406(2) yes
O101 . H1011 . 0.878(17) no
C102 . H1021 . 0.952 no
C102 . H1022 . 0.969 no
C102 . H1023 . 0.974 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 . N2 . H21 . 112.9(12) no
C3 . N1 . H12 . 120.6(12) no
C3 . N1 . H11 . 117.1(12) no
H12 . N1 . H11 . 122.3(17) no
N1 . C3 . N2 . 124.97(15) yes
N1 . C3 . C4 . 116.67(14) yes
N2 . C3 . C4 . 118.37(15) yes
C3 . C4 . C5 . 121.48(13) yes
C3 . C4 . C9 . 119.71(13) yes
C5 . C4 . C9 . 118.80(13) yes
C4 . C5 . C6 . 120.39(13) yes
C4 . C5 . H51 . 118.9 no
C6 . C5 . H51 . 120.7 no
C5 . C6 . C7 . 121.25(13) yes
C5 . C6 . H61 . 119.7 no
C7 . C6 . H61 . 119.0 no
C6 . C7 . C8 . 118.02(12) yes
C6 . C7 . C10 . 118.20(11) yes
C8 . C7 . C10 . 123.33(11) yes
C7 . C8 . C9 . 120.78(13) yes
C7 . C8 . H81 . 119.0 no
C9 . C8 . H81 . 120.2 no
C8 . C9 . C4 . 120.76(13) yes
C8 . C9 . H91 . 120.0 no
C4 . C9 . H91 . 119.3 no
C7 . C10 . C7 4_655 112.87(5) yes
C7 . C10 . C7 6_665 102.88(10) yes
C7 4_655 C10 . C7 6_665 112.87(5) yes
C7 . C10 . C7 8_565 112.87(5) yes
C7 4_655 C10 . C7 8_565 102.88(10) yes
C7 6_665 C10 . C7 8_565 112.87(5) yes
C102 . O101 . H1011 . 103.9(18) no
O101 . C102 . H1021 . 107.1 no
O101 . C102 . H1022 . 112.0 no
H1021 . C102 . H1022 . 109.3 no
O101 . C102 . H1023 . 109.2 no
H1021 . C102 . H1023 . 108.9 no
H1022 . C102 . H1023 . 110.2 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 . H51 . O101 8_566 130 0.95 2.59 3.2818(19) yes
N1 . H12 . O101 8_566 170.3(19) 0.899 2.175 3.0646(19) yes
N1 . H11 . O101 2_667 160(2) 0.864 2.280 3.1047(19) yes
N2 . H21 . N2 2_667 121.5(17) 0.907 2.476 3.0505(19) yes
O101 . H1011 . N2 . 171(3) 0.878 1.909 2.7796(19) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 14/08/19 at 09:05:10
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (     2 ,X'S,U'S)  UNTIL C    (   102 ) 
CONT H    (    12 ,X'S,U[ISO])  UNTIL H    (  1011 ) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   ( 102,X'S) H   (1021,X'S) H   (1022,X'S) H   (1023,X'S) 
END                                                                             
;

_iucr_refine_instructions_details_restraints 
;
#
# Punched on 14/08/19 at 09:05:10
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H  NO #H U MULT   DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM 
REM TO ACTIVATE THE VIB RESTRAINTS, REMOVE LEADING REM 
REM            H1-N-R1 
DIST 0.86, 0.02 = 
CONT N ( 2) TO H(21) 
REST 0.041, 0.002 = H(21,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 2) TO H(21) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(12) 
CONT N ( 1) TO H(11) 
REST 0.047, 0.002 = H(12,U[ISO]) 
REST 0.047, 0.002 = H(11,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(3) TO N ( 1) TO H(12) 
CONT C(3) TO N ( 1) TO H(11) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 101) TO H(1011) 
REST 0.057, 0.002 = H(1011,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol, acetone, diethyl ether'
####################################################################### 
# 
# 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_1HCO3
_database_code_depnum_ccdc_archive 'CCDC 1949479'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;The Australian National University
Australia
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;
#==============================================================================

# start Validation Reply Form
_vrf_PLAT430_1HCO3               
;
PROBLEM: Short Inter D...A Contact  O22      ..O23      .       2.02 Ang.  
RESPONSE: The 2 x A and 2 x B alerts highlighting closer than 
expected O..O contacts relate to the disorder noted in the 
dimeric (HCO3)2-/water units. The disorder model involves the 
symmetry related atom pairs not being simultaneously present. 
Silimarly, there are a range of G alerts relating to short 
contacts and <100% occupancies etc due to the various disorders 
built into the refinement model.  
;
# end Validation Reply Form

_audit_creation_date             2019-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C H O3), C29 H32 N8, 3(O)'
_chemical_formula_sum            'C33 H36 N8 O15'
_chemical_formula_weight         784.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C33 H44 N8 O16'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      tetragonal
_space_group_IT_number           133
_space_group_name_H-M_alt        'P 42/n b c'
_space_group_name_Hall           '-P 4ac 2b'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, y+1/2, -z'
'y, x, -z+1/2'
'y+1/2, x+1/2, z+1/2'
'y+1/2, -x, -z+1/2'
'-y, x+1/2, -z+1/2'
'-x+1/2, y, -z'
'x, -y+1/2, -z'
'-x, -y, -z'
'-x-1/2, -y-1/2, z'
'-y, -x, z-1/2'
'-y-1/2, -x-1/2, -z-1/2'
'-y-1/2, x, z-1/2'
'y, -x-1/2, z-1/2'
'x-1/2, -y, z'
'-x, y-1/2, z'

_cell_length_a                   13.38177(8)
_cell_length_b                   13.38177(8)
_cell_length_c                   21.75010(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3894.83(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12480
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5640
_cell_measurement_theta_min      3.9020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -5 -10 0.1571
-8 4 0 0.0736
5 4 9 0.1467
8 -4 0 0.0644
-3 -8 1 0.0589
0 1 14 0.1639
-3 -8 -3 0.0883
3 8 0 0.0729
1 2 14 0.1625
2 6 -10 0.1547

_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.142

loop_
_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
-3.1261 -5.0859 -10.2431 -0.1027 0.0005 0.9947
-7.9536 3.5007 0.0074 -0.9996 0.0253 -0.0090
5.3833 3.5750 9.4204 0.4096 -0.0084 -0.9122
7.8820 -3.6545 -0.3013 0.9990 -0.0253 0.0376
-3.4450 -7.9378 1.2696 0.0186 0.7863 0.6175
0.4940 1.2413 13.9406 0.0159 0.5650 -0.8249
-3.3503 -7.8237 -2.8238 0.0163 0.5756 0.8176
3.4324 7.9810 0.0432 -0.0198 -0.7254 -0.6881
0.6596 1.7001 13.7936 0.0112 0.5172 -0.8558
2.4516 5.5785 -10.0646 -0.0251 -0.9989 0.0385

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24851
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.704
_diffrn_reflns_theta_min         4.065
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  29.00   1.00    2.00    --  -36.95  57.00   0.00   50
  2  ω    -27.00  50.00   1.00    2.00    --   36.95 -57.00 -90.00   77
  3  ω     58.00  90.00   1.00    2.00    --   36.95-125.00  60.00   32
  4  ω     36.00  88.00   1.00    2.00    --   36.95-125.00 150.00   52
  5  ω     31.00  75.00   1.00    2.00    --   36.95-125.00-120.00   44
  6  ω    -29.00  34.00   1.00    2.00    --   36.95 -58.00  17.00   63
  7  ω     37.00  65.00   1.00    2.00    --   36.95-125.00  30.00   28
  8  ω     50.00 108.00   1.00    2.00    --   36.95  19.00   0.00   58
  9  ω     33.00  85.00   1.00    2.00    --   36.95-125.00   0.00   52
 10  ω     84.00 117.00   1.00   16.00    --  111.00  12.00 -90.00   33
 11  ω     47.00  72.00   1.00   16.00    --  111.00 -92.00  30.00   25
 12  ω     52.00  78.00   1.00   16.00    --  111.00 -50.00  90.00   26
 13  ω     80.00 106.00   1.00   16.00    --  111.00 -92.00  30.00   26
 14  ω     42.00 129.00   1.00   16.00    --  111.00 -38.00   0.00   87
 15  ω     81.00 107.00   1.00   16.00    --  111.00-111.00  60.00   26
 16  ω     65.00  91.00   1.00   16.00    --  111.00 -92.00   0.00   26
 17  ω    150.00 175.00   1.00   16.00    --  111.00 111.00 120.00   25
 18  ω    109.00 143.00   1.00   16.00    --  111.00 111.00 120.00   34
 19  ω    104.00 144.00   1.00   16.00    --  111.00  77.00 -90.00   40
 20  ω     43.00 105.00   1.00   16.00    --  111.00 -92.00 -60.00   62
 21  ω     75.00 101.00   1.00   16.00    --  111.00  12.00  60.00   26
 22  ω     45.00  70.00   1.00   16.00    --  111.00-111.00  60.00   25
 23  ω     47.00 122.00   1.00   16.00    --  111.00 -64.00  60.00   75
 24  ω    109.00 175.00   1.00   16.00    --  111.00  77.00  90.00   66
 25  ω     96.00 125.00   1.00   16.00    --  111.00 -50.00  90.00   29
 26  ω     44.00  76.00   1.00   16.00    --  111.00 -92.00 -90.00   32
 27  ω     53.00 103.00   1.00   16.00    --  111.00 -92.00-120.00   50
 28  ω     42.00  70.00   1.00   16.00    --  111.00-111.00 120.00   28
 29  ω     83.00 109.00   1.00   16.00    --  111.00-111.00 120.00   26
 30  ω    138.00 174.00   1.00   16.00    --  111.00  50.00  60.00   36
 31  ω     97.00 124.00   1.00   16.00    --  111.00  50.00-120.00   27
 32  ω    141.00 170.00   1.00   16.00    --  111.00  12.00 -90.00   29
 33  ω     79.00 105.00   1.00   16.00    --  111.00 -50.00  30.00   26
 34  ω     47.00 114.00   1.00   16.00    --  111.00 -38.00  90.00   67
 35  ω     66.00 114.00   1.00   16.00    --  111.00 -77.00 150.00   48
 36  ω     76.00 102.00   1.00   16.00    --  111.00 -32.00-164.66   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1047584000
_diffrn_orient_matrix_UB_12      -0.0475480000
_diffrn_orient_matrix_UB_13      0.0016613000
_diffrn_orient_matrix_UB_21      -0.0363668000
_diffrn_orient_matrix_UB_22      -0.0755115000
_diffrn_orient_matrix_UB_23      0.0485411000
_diffrn_orient_matrix_UB_31      -0.0308915000
_diffrn_orient_matrix_UB_32      -0.0726465000
_diffrn_orient_matrix_UB_33      -0.0516123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1812
_reflns_number_total             1976
_reflns_odcompleteness_completeness 98.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_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         0.652
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1976
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0810
_refine_ls_restrained_S_all      1.088
_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)+(0.1677P)²+2.9553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2398
_refine_ls_wR_factor_ref         0.2466
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C21-O21 = C21-O23
 1.31 with sigma of 0.01
 C21-O22
 1.24 with sigma of 0.01
3. Others
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C9)=Sof(H9)=Sof(C8)=Sof(H8)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=FVAR(1)
 Fixed Sof: H11(0.5) O22(0.5) O21(0.5) O23(0.5) C21(0.5) O101(0.5) O111(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C5(H5), C6(H6), C9(H9), C8(H8)
4.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
4.c Idealised tetrahedral OH refined as rotating group:
 O11(H11)
;
_atom_sites_solution_hydrogens   mixed
_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
O12 O 0.750000 0.48592(18) 0.500000 0.0495(7) Uani 1 2 d S T P . .
O11 O 0.67018(13) 0.34288(12) 0.51506(8) 0.0376(5) Uani 1 1 d . . . . .
H11 H 0.671859 0.287538 0.498900 0.056 Uiso 0.5 1 calc GR . . . .
C11 C 0.750000 0.3928(2) 0.500000 0.0324(7) Uani 1 2 d S T P . .
O22 O 0.3040(5) 0.1461(4) 0.1184(3) 0.0781(19) Uani 0.5 1 d D . . A 1
O21 O 0.3166(7) 0.1382(4) 0.2196(3) 0.115(3) Uani 0.5 1 d D . . A .
O23 O 0.2082(4) 0.2387(5) 0.1776(2) 0.0827(18) Uani 0.5 1 d D . . A .
C21 C 0.2760(5) 0.1751(4) 0.1686(3) 0.063(2) Uani 0.5 1 d D . . . .
N1 N 0.6076(2) 0.58526(18) 0.57256(11) 0.0538(7) Uani 1 1 d . . . . .
H1A H 0.650261 0.556129 0.549032 0.065 Uiso 1 1 calc R . . . .
H1B H 0.616271 0.646665 0.582947 0.065 Uiso 1 1 calc R . . . .
N2 N 0.51524(18) 0.44354(15) 0.57737(10) 0.0415(6) Uani 1 1 d . . . . .
H2A H 0.557312 0.413512 0.553873 0.050 Uiso 1 1 calc R . . . .
H2B H 0.463610 0.412143 0.590833 0.050 Uiso 1 1 calc R . . . .
C3 C 0.5297(2) 0.53625(18) 0.59252(10) 0.0370(6) Uani 1 1 d . . . . .
C4 C 0.45566(18) 0.58867(17) 0.63160(10) 0.0343(6) Uani 1 1 d . . . . .
C7 C 0.32119(16) 0.69060(16) 0.70788(9) 0.0279(5) Uani 1 1 d . . . . .
C10 C 0.250000 0.750000 0.750000 0.0239(8) Uani 1 4 d S T P B .
C15 C 0.3620(7) 0.5816(7) 0.6266(4) 0.027(2) Uani 0.208(4) 1 d . . . B 1
H15 H 0.336665 0.539434 0.596372 0.033 Uiso 0.208(4) 1 calc R . . B 1
C16 C 0.2942(7) 0.6331(8) 0.6634(4) 0.027(2) Uani 0.208(4) 1 d . . . B 1
H16 H 0.226326 0.625513 0.655577 0.032 Uiso 0.208(4) 1 calc R . . B 1
C18 C 0.4292(8) 0.7225(8) 0.7103(5) 0.030(2) Uani 0.208(4) 1 d . . . B 1
H18 H 0.450316 0.773162 0.736505 0.036 Uiso 0.208(4) 1 calc R . . B 1
C19 C 0.4966(8) 0.6732(9) 0.6716(5) 0.037(3) Uani 0.208(4) 1 d . . . B 1
H19 H 0.563684 0.691190 0.670236 0.044 Uiso 0.208(4) 1 calc R . . B 1
C5 C 0.4039(2) 0.5356(2) 0.67798(14) 0.0359(7) Uani 0.792(4) 1 d . . . B 2
H5 H 0.414232 0.467383 0.683034 0.043 Uiso 0.792(4) 1 calc R . . B 2
C6 C 0.3373(2) 0.5862(2) 0.71596(13) 0.0322(7) Uani 0.792(4) 1 d . . . B 2
H6 H 0.303278 0.551876 0.746670 0.039 Uiso 0.792(4) 1 calc R . . B 2
C9 C 0.4339(2) 0.6865(2) 0.62188(12) 0.0335(7) Uani 0.792(4) 1 d . . . B 2
H9 H 0.464469 0.720432 0.589646 0.040 Uiso 0.792(4) 1 calc R . . B 2
C8 C 0.3671(2) 0.73618(19) 0.65913(12) 0.0313(7) Uani 0.792(4) 1 d . . . B 2
H8 H 0.352804 0.802856 0.650909 0.038 Uiso 0.792(4) 1 calc R . . B 2
O101 O 0.3113(3) 0.1404(3) 0.0829(2) 0.0425(9) Uani 0.5 1 d . . . C 2
O111 O 0.250000 0.2171(4) 0.000000 0.0584(16) Uani 0.5 2 d S T P D 3
H21 H 0.313(5) 0.187(5) 0.250000 0.13(3) Uiso 1 2 d S T P . .


_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
O12 C11 1.246(4) . ?
O11 C11 1.302(2) . ?
O22 C21 1.216(7) . ?
O21 C21 1.330(6) . ?
O23 C21 1.260(7) . ?
N1 C3 1.306(4) . ?
N2 C3 1.298(3) . ?
C3 C4 1.482(3) . ?
C4 C15 1.261(10) . ?
C4 C19 1.529(11) . ?
C4 C5 1.415(4) . ?
C4 C9 1.358(4) . ?
C7 C10 1.5422(19) . ?
C7 C16 1.288(10) . ?
C7 C18 1.509(10) . ?
C7 C6 1.424(3) . ?
C7 C8 1.369(3) . ?
C15 C16 1.393(14) . ?
C18 C19 1.398(14) . ?
C5 C6 1.391(4) . ?
C9 C8 1.377(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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 C11 O11 120.89(13) . 7_656 ?
O12 C11 O11 120.89(13) . . ?
O11 C11 O11 118.2(3) 7_656 . ?
O22 C21 O21 120.3(6) . . ?
O22 C21 O23 125.2(5) . . ?
O23 C21 O22 113.8(6) 10_665 . ?
O23 C21 O21 98.6(5) 10_665 . ?
O23 C21 O21 114.5(6) . . ?
O23 C21 O23 56.4(5) 10_665 . ?
N1 C3 C4 119.1(2) . . ?
N2 C3 N1 120.9(2) . . ?
N2 C3 C4 119.9(2) . . ?
C3 C4 C19 115.9(5) . . ?
C15 C4 C3 125.4(5) . . ?
C15 C4 C19 117.4(6) . . ?
C5 C4 C3 119.9(2) . . ?
C9 C4 C3 120.7(2) . . ?
C9 C4 C5 119.3(2) . . ?
C16 C7 C10 125.5(5) . . ?
C16 C7 C18 117.6(6) . . ?
C18 C7 C10 115.2(4) . . ?
C6 C7 C10 121.72(18) . . ?
C8 C7 C10 120.52(18) . . ?
C8 C7 C6 117.7(2) . . ?
C7 C10 C7 110.66(8) . 6_656 ?
C7 C10 C7 107.12(15) 6_656 5_466 ?
C7 C10 C7 110.66(8) . 5_466 ?
C7 C10 C7 107.12(15) . 10_675 ?
C7 C10 C7 110.66(8) 10_675 5_466 ?
C7 C10 C7 110.66(8) 6_656 10_675 ?
C4 C15 C16 124.1(8) . . ?
C7 C16 C15 123.0(9) . . ?
C19 C18 C7 117.6(8) . . ?
C18 C19 C4 117.4(9) . . ?
C6 C5 C4 119.5(2) . . ?
C5 C6 C7 120.1(2) . . ?
C4 C9 C8 120.9(2) . . ?
C7 C8 C9 122.1(2) . . ?


_ins_header                      
;
TITL NGW386 in P4(2)/nbc 
REM P4(2)/nbc (#133 in standard setting)
CELL 1.54184  13.381771  13.381771  21.750096  90.0000  90.0000  90.0000
ZERR    4.00   0.000077   0.000077   0.000182   0.0000   0.0000   0.0000
LATT  1
SYMM -x+1/2,-y+1/2, z 
SYMM -y+1/2, x, z+1/2 
SYMM  y,-x+1/2, z+1/2 
SYMM -x+1/2, y,-z 
SYMM  x,-y+1/2,-z 
SYMM  y, x,-z+1/2 
SYMM -y+1/2,-x+1/2,-z+1/2 
SFAC C H N O
UNIT 132.00 176.00 32.00 64.00
TREF
HKLF 4
END
;
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.496

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
