# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Met-NAM
_database_code_depnum_ccdc_archive 'CCDC 2067490'
_audit_update_record             
;
2021-03-02 deposited with the CCDC.	2021-09-09 downloaded from the CCDC.
;

_audit_creation_method           'MRIA, SHELXL-97'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 N O3, C6 H6 N2 O'
_chemical_formula_sum            'C18 H21 N3 O4'
_chemical_formula_weight         343.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 '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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4865(7)
_cell_length_b                   10.4664(12)
_cell_length_c                   15.4477(15)
_cell_angle_alpha                96.842(15)
_cell_angle_beta                 90.303(11)
_cell_angle_gamma                97.911(14)
_cell_volume                     872.16(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1070
_cell_measurement_theta_min      2.894
_cell_measurement_theta_max      39.981

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.
_pd_spec_size_axial              15 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              1 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              1 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 
thin layer in the specimen holder of the camera
;
_pd_spec_mount_mode              transmission # options are 'reflection' 
# or 'transmission'

_pd_spec_shape                   flat_sheet # options are 'cylinder',
# 'flat_sheet' or 'irregular'

_pd_char_particle_morphology     'no specific habit'
_pd_char_colour                  colorless # use ICDD colour descriptions

# The following three fields describe the preparation of the specimen. 
# The cooling rate is in K/min.  The pressure at which the sample was
# prepared is in kPa.  The temperature of preparation is in K.



_pd_prep_cool_rate               ?
_pd_prep_pressure                101
_pd_prep_temperature             295(2)


_exptl_special_details           
; 
 ? 
;

# This following item is used to identify the equipment used to record the
# powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
;
Dept. of Chemistry, Moscow State University, 119991 Moscow, Russia
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Fine focus X-ray tube'
_diffrn_source_target            Cu

_diffrn_radiation_source         'line-focus sealed tube'
_diffrn_radiation_monochromator  'Curved Germanium (111)'
_diffrn_measurement_device       'Guinier camera G670'
_diffrn_detector_type            'Imaging Plate'



_diffrn_reflns_number            ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?


_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;
# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_type           CuK\a~1~
_diffrn_radiation_wavelength     1.54059

# The following four items give details of the measured (not processed)
# powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        7601
_pd_meas_2theta_range_min        4.00
_pd_meas_2theta_range_max        80.00
_pd_meas_2theta_range_inc        0.01

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?

# The following fields are used to identify the programs used.

_computing_data_collection       
'G670 Imaging Plate Guinier Camera Software (Huber, 2002)'
_computing_cell_refinement       'MRIA (Zlokazov & Chernyshev, 1992)'
_computing_data_reduction        
'G670 Imaging Plate Guinier Camera Software'
_computing_structure_solution    'simulated annealing (Zhukov et al., 2001)'
_computing_structure_refinement  MRIA
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'MRIA, SHELXL97 (Sheldrick, 2008)'

#==============================================================================

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text
_pd_proc_ls_profile_function     'split-type pseudo-Voigt (Toraya, 1986)'
_pd_proc_ls_pref_orient_corr     none
_pd_proc_ls_background_function  'Chebyshev polynomial up to the 5th order'

_pd_proc_ls_prof_R_factor        0.0311
_pd_proc_ls_prof_wR_factor       0.0408
_pd_proc_ls_prof_wR_expected     0.0198

_refine_special_details          
; ?
;

_refine_ls_R_I_factor            0.0834
_refine_ls_structure_factor_coef Inet
_refine_ls_matrix_type           fullcycle
_refine_ls_weighting_scheme      sigma
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     121
_refine_ls_number_restraints     85
_refine_ls_number_constraints    0

# The following item is the same as CHI, the square root of 'CHI squared=2.274'
_refine_ls_goodness_of_fit_all   2.061

_refine_ls_restrained_S_all      ?
_refine_ls_restrained_S_obs      ?
_refine_ls_shift/su_max          .004
_refine_ls_shift/su_mean         .001


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.
_pd_proc_2theta_range_min        4.00
_pd_proc_2theta_range_max        80.00
_pd_proc_2theta_range_inc        0.01

_pd_proc_wavelength              1.54059

_pd_block_diffractogram_id       INA-PCA_pattern # The id used for the block
# containing the powder 
# pattern profile (section 11).

# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions   none
_pd_proc_info_data_reduction     ?

#==============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2038(10) 0.1227(5) 0.7747(4) 0.060(5) Uiso 1 1 d . . .
O2 O 0.5800(10) 0.1133(5) 0.6435(4) 0.061(5) Uiso 1 1 d . . .
O3 O 0.8783(10) 0.1411(5) 0.5456(3) 0.061(6) Uiso 1 1 d . . .
N1 N 0.7247(12) -0.0613(7) 0.5811(4) 0.068(7) Uiso 1 1 d . . .
H1 H 0.7955 -0.1088 0.5425 0.082 Uiso 1 1 calc . . .
C1 C 0.1338(16) 0.1636(9) 0.8565(6) 0.066(9) Uiso 1 1 d . . .
C2 C 0.2198(16) 0.1221(8) 0.9325(6) 0.058(9) Uiso 1 1 d . . .
H2 H 0.3323 0.0629 0.9282 0.070 Uiso 1 1 calc . . .
C3 C 0.1410(16) 0.1672(8) 1.0134(6) 0.066(10) Uiso 1 1 d . . .
C4 C -0.0372(16) 0.2533(8) 1.0175(6) 0.065(9) Uiso 1 1 d . . .
H4 H -0.0971 0.2821 1.0715 0.078 Uiso 1 1 calc . . .
C5 C -0.1251(16) 0.2961(8) 0.9431(6) 0.070(9) Uiso 1 1 d . . .
C6 C -0.0536(17) 0.2453(8) 0.8626(6) 0.066(9) Uiso 1 1 d . . .
H6 H -0.1276 0.2644 0.8123 0.079 Uiso 1 1 calc . . .
C7 C 0.2410(15) 0.1258(8) 1.0955(6) 0.064(9) Uiso 1 1 d . . .
H7A H 0.1656 0.1666 1.1454 0.096 Uiso 1 1 calc . . .
H7B H 0.4160 0.1514 1.0996 0.096 Uiso 1 1 calc . . .
H7C H 0.2050 0.0331 1.0936 0.096 Uiso 1 1 calc . . .
C8 C -0.3154(16) 0.3903(8) 0.9477(6) 0.062(8) Uiso 1 1 d . . .
H8A H -0.3472 0.4176 1.0076 0.093 Uiso 1 1 calc . . .
H8B H -0.4652 0.3477 0.9188 0.093 Uiso 1 1 calc . . .
H8C H -0.2532 0.4647 0.9195 0.093 Uiso 1 1 calc . . .
C9 C 0.3917(17) 0.0353(9) 0.7696(6) 0.061(10) Uiso 1 1 d . . .
H9A H 0.3355 -0.0426 0.7962 0.073 Uiso 1 1 calc . . .
H9B H 0.5435 0.0781 0.7986 0.073 Uiso 1 1 calc . . .
C10 C 0.4281(16) 0.0033(9) 0.6744(6) 0.069(9) Uiso 1 1 d . . .
H10 H 0.2681 -0.0118 0.6437 0.083 Uiso 1 1 calc . . .
C11 C 0.5690(17) -0.1117(9) 0.6483(6) 0.072(11) Uiso 1 1 d . . .
H11A H 0.6653 -0.1306 0.6969 0.086 Uiso 1 1 calc . . .
H11B H 0.4590 -0.1892 0.6255 0.086 Uiso 1 1 calc . . .
C12 C 0.7449(14) 0.0696(8) 0.5866(5) 0.058(9) Uiso 1 1 d . . .
O4 O 0.7009(10) 0.6191(5) 0.5792(4) 0.061(5) Uiso 1 1 d . . .
N2 N 0.7064(11) 0.4051(6) 0.5514(4) 0.060(6) Uiso 1 1 d . . .
H2A H 0.5890 0.3985 0.5133 0.072 Uiso 1 1 calc . . .
H2B H 0.7685 0.3372 0.5617 0.072 Uiso 1 1 calc . . .
N3 N 1.3251(13) 0.4484(6) 0.7293(5) 0.066(7) Uiso 1 1 d . . .
C13 C 0.7924(16) 0.5210(9) 0.5946(6) 0.070(10) Uiso 1 1 d . . .
C14 C 0.9948(15) 0.5344(8) 0.6619(6) 0.069(9) Uiso 1 1 d . . .
C15 C 1.0695(16) 0.6551(8) 0.7099(5) 0.071(9) Uiso 1 1 d . . .
H15 H 0.9910 0.7260 0.7013 0.085 Uiso 1 1 calc . . .
C16 C 1.2617(15) 0.6688(9) 0.7706(6) 0.074(11) Uiso 1 1 d . . .
H16 H 1.3063 0.7470 0.8060 0.089 Uiso 1 1 calc . . .
C17 C 1.3846(17) 0.5645(9) 0.7774(6) 0.067(9) Uiso 1 1 d . . .
H17 H 1.5155 0.5747 0.8173 0.081 Uiso 1 1 calc . . .
C18 C 1.1308(17) 0.4344(9) 0.6738(6) 0.074(10) Uiso 1 1 d . . .
H18 H 1.0847 0.3536 0.6416 0.089 Uiso 1 1 calc . . .

_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 1.360(10) . ?
O1 C9 1.466(11) . ?
O2 C12 1.352(10) . ?
O2 C10 1.455(10) . ?
O3 C12 1.210(10) . ?
N1 C12 1.351(11) . ?
N1 C11 1.450(11) . ?
N1 H1 0.8602 . ?
C1 C2 1.401(13) . ?
C1 C6 1.422(13) . ?
C2 C3 1.376(12) . ?
C2 H2 0.9299 . ?
C3 C4 1.415(13) . ?
C3 C7 1.512(13) . ?
C4 C5 1.389(13) . ?
C4 H4 0.9298 . ?
C5 C6 1.374(13) . ?
C5 C8 1.528(13) . ?
C6 H6 0.9299 . ?
C7 H7A 0.9603 . ?
C7 H7B 0.9599 . ?
C7 H7C 0.9599 . ?
C8 H8A 0.9601 . ?
C8 H8B 0.9601 . ?
C8 H8C 0.9599 . ?
C9 C10 1.490(12) . ?
C9 H9A 0.9702 . ?
C9 H9B 0.9699 . ?
C10 C11 1.534(13) . ?
C10 H10 0.9802 . ?
C11 H11A 0.9699 . ?
C11 H11B 0.9698 . ?
O4 C13 1.250(11) . ?
N2 C13 1.336(10) . ?
N2 H2A 0.8601 . ?
N2 H2B 0.8600 . ?
N3 C17 1.345(11) . ?
N3 C18 1.346(12) . ?
C13 C14 1.497(12) . ?
C14 C15 1.394(11) . ?
C14 C18 1.395(14) . ?
C15 C16 1.389(12) . ?
C15 H15 0.9297 . ?
C16 C17 1.373(14) . ?
C16 H16 0.9299 . ?
C17 H17 0.9301 . ?
C18 H18 0.9296 . ?

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
C1 O1 C9 115.6(7) . . ?
C12 O2 C10 109.5(6) . . ?
C12 N1 C11 111.7(7) . . ?
C12 N1 H1 124.2 . . ?
C11 N1 H1 124.1 . . ?
O1 C1 C2 124.2(8) . . ?
O1 C1 C6 116.4(8) . . ?
C2 C1 C6 119.2(8) . . ?
C3 C2 C1 121.3(9) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 118.0(8) . . ?
C2 C3 C7 121.1(8) . . ?
C4 C3 C7 120.9(8) . . ?
C5 C4 C3 121.8(8) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.0 . . ?
C6 C5 C4 119.3(9) . . ?
C6 C5 C8 118.7(8) . . ?
C4 C5 C8 121.8(8) . . ?
C5 C6 C1 119.8(8) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.4 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 C10 104.5(7) . . ?
O1 C9 H9A 110.8 . . ?
C10 C9 H9A 110.9 . . ?
O1 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
O2 C10 C9 108.3(7) . . ?
O2 C10 C11 104.1(7) . . ?
C9 C10 C11 115.9(8) . . ?
O2 C10 H10 109.5 . . ?
C9 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
N1 C11 C10 100.6(7) . . ?
N1 C11 H11A 111.6 . . ?
C10 C11 H11A 111.6 . . ?
N1 C11 H11B 111.6 . . ?
C10 C11 H11B 111.6 . . ?
H11A C11 H11B 109.4 . . ?
O3 C12 O2 122.5(8) . . ?
O3 C12 N1 127.7(8) . . ?
O2 C12 N1 109.7(7) . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C17 N3 C18 117.5(8) . . ?
O4 C13 N2 119.5(8) . . ?
O4 C13 C14 119.7(7) . . ?
N2 C13 C14 120.8(8) . . ?
C15 C14 C18 117.2(8) . . ?
C15 C14 C13 119.4(8) . . ?
C18 C14 C13 123.0(8) . . ?
C16 C15 C14 119.6(9) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 118.6(8) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
N3 C17 C16 123.3(8) . . ?
N3 C17 H17 118.3 . . ?
C16 C17 H17 118.4 . . ?
N3 C18 C14 123.6(8) . . ?
N3 C18 H18 118.2 . . ?
C14 C18 H18 118.2 . . ?

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

N1 H1 O3 0.86 2.29 3.071(8) 151 2_756
N2 H2A O4 0.86 2.11 2.967(8) 179 2_666
N2 H2B O3 0.86 2.20 3.032(8) 161 .

_refine_diff_density_max         0.36
_refine_diff_density_min         -0.25
_refine_diff_density_rms         0.17
####################################################################### 
# 
# 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_Metaxalone-4-hydroxybenzoicacid
_database_code_depnum_ccdc_archive 'CCDC 2067491'
_audit_update_record             
;
2021-03-02 deposited with the CCDC.	2021-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 N O3, C7 H6 O3'
_chemical_formula_sum            'C19 H21 N O6'
_chemical_formula_weight         359.37

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1182(2)
_cell_length_b                   13.3984(5)
_cell_length_c                   14.4561(6)
_cell_angle_alpha                89.4000(10)
_cell_angle_beta                 88.7370(10)
_cell_angle_gamma                89.3480(10)
_cell_volume                     990.98(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      30.54

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32063
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.819
_diffrn_reflns_theta_max         30.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6043
_reflns_number_gt                5599
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1104P)²+0.2991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6043
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1733
_refine_ls_wR_factor_gt          0.1706
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.76914(16) 0.53537(6) 0.09143(6) 0.02248(18) Uani 1 1 d . . . . .
O2 O 0.89180(16) 0.46500(6) 0.22515(5) 0.02086(17) Uani 1 1 d . . . . .
O3 O 0.82273(15) 0.26082(6) 0.27679(5) 0.01909(17) Uani 1 1 d . . . . .
O4 O -0.2604(2) 0.91766(8) -0.03774(7) 0.0337(2) Uani 1 1 d . . . . .
O5 O 0.40920(17) 0.61633(6) 0.20567(6) 0.02502(19) Uani 1 1 d . . . . .
O6 O -0.41168(18) 0.95088(7) 0.10537(7) 0.0314(2) Uani 1 1 d D . . . .
N1 N 1.11393(18) 0.42315(7) 0.09884(6) 0.02083(19) Uani 1 1 d . . . . .
C3 C 0.9186(2) 0.47825(7) 0.13313(7) 0.01740(19) Uani 1 1 d . . . . .
C4 C 1.1028(2) 0.39980(8) 0.25713(7) 0.0186(2) Uani 1 1 d . . . . .
H7 H 1.231842 0.440216 0.288435 0.022 Uiso 1 1 calc R U . . .
C5 C 0.9864(2) 0.32630(8) 0.32565(7) 0.01812(19) Uani 1 1 d . . . . .
H6 H 1.124165 0.288551 0.355576 0.022 Uiso 1 1 calc R U . . .
H10 H 0.885137 0.361398 0.372851 0.022 Uiso 1 1 calc R U . . .
C6 C 0.64882(19) 0.20488(7) 0.32894(7) 0.01688(19) Uani 1 1 d . . . . .
C7 C 0.4884(2) 0.14340(8) 0.27815(7) 0.0189(2) Uani 1 1 d . . . . .
H5 H 0.507628 0.141005 0.214087 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2994(2) 0.08558(8) 0.32338(9) 0.0232(2) Uani 1 1 d . . . . .
C9 C 0.1276(3) 0.01826(10) 0.26909(10) 0.0317(3) Uani 1 1 d . . . . .
H13 H 0.222608 -0.041622 0.253410 0.048 Uiso 1 1 calc R U . . .
H12 H 0.075242 0.051977 0.213462 0.048 Uiso 1 1 calc R U . . .
H2 H -0.024590 0.001502 0.305759 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4044(3) 0.15587(11) 0.57481(9) 0.0371(3) Uani 1 1 d . . . . .
H4 H 0.392446 0.089444 0.599982 0.056 Uiso 1 1 calc R U . . .
H15 H 0.248173 0.192781 0.590664 0.056 Uiso 1 1 calc R U . . .
H3 H 0.552709 0.188462 0.599896 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4355(2) 0.15102(8) 0.47099(8) 0.0247(2) Uani 1 1 d . . . . .
C12 C 0.2743(2) 0.09079(9) 0.41947(9) 0.0267(2) Uani 1 1 d . . . . .
H14 H 0.146738 0.053125 0.449921 0.032 Uiso 1 1 calc R U . . .
C13 C 1.2283(2) 0.35736(8) 0.16799(7) 0.0200(2) Uani 1 1 d . . . . .
H8 H 1.417235 0.362305 0.167949 0.024 Uiso 1 1 calc R U . . .
H9 H 1.180171 0.288391 0.158900 0.024 Uiso 1 1 calc R U . . .
C14 C 0.6267(2) 0.20838(8) 0.42522(7) 0.0202(2) Uani 1 1 d . . . . .
H11 H 0.737452 0.248297 0.458621 0.024 Uiso 1 1 calc R U . . .
C15 C -0.2611(2) 0.90326(9) 0.04886(8) 0.0231(2) Uani 1 1 d . . . . .
C16 C -0.0836(2) 0.82754(8) 0.08841(8) 0.0207(2) Uani 1 1 d . . . . .
C17 C 0.1112(2) 0.78247(8) 0.03346(8) 0.0219(2) Uani 1 1 d . . . . .
H18 H 0.128392 0.799868 -0.028804 0.026 Uiso 1 1 calc R U . . .
C18 C 0.2795(2) 0.71178(8) 0.07137(8) 0.0217(2) Uani 1 1 d . . . . .
H17 H 0.409601 0.682137 0.034691 0.026 Uiso 1 1 calc R U . . .
C19 C 0.2525(2) 0.68544(8) 0.16481(8) 0.0195(2) Uani 1 1 d . . . . .
C20 C -0.1097(2) 0.80015(9) 0.18171(8) 0.0234(2) Uani 1 1 d . . . . .
H19 H -0.240218 0.829470 0.218409 0.028 Uiso 1 1 calc R U . . .
C21 C 0.0571(2) 0.72975(9) 0.21989(8) 0.0237(2) Uani 1 1 d . . . . .
H16 H 0.039105 0.712023 0.282055 0.028 Uiso 1 1 calc R U . . .
H1 H 1.151(4) 0.4205(16) 0.0385(16) 0.042(5) Uiso 1 1 d . . . . .
H21 H 0.518(5) 0.5967(18) 0.1692(17) 0.051(6) Uiso 1 1 d . . . . .
H61 H -0.548(5) 0.991(2) 0.078(2) 0.076 Uiso 1 1 d D U . . .


_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 C3 1.2374(13) . ?
O2 C3 1.3445(12) . ?
O2 C4 1.4614(13) . ?
O3 C6 1.3770(12) . ?
O3 C5 1.4234(12) . ?
O4 C15 1.2646(15) . ?
O5 C19 1.3572(13) . ?
O5 H21 0.80(3) . ?
O6 C15 1.2808(14) . ?
O6 H61 0.97(3) . ?
N1 C3 1.3264(13) . ?
N1 C13 1.4542(13) . ?
N1 H1 0.89(2) . ?
C4 C5 1.5077(14) . ?
C4 C13 1.5384(15) . ?
C4 H7 0.9800 . ?
C5 H6 0.9700 . ?
C5 H10 0.9700 . ?
C6 C7 1.3951(14) . ?
C6 C14 1.3951(14) . ?
C7 C8 1.3935(14) . ?
C7 H5 0.9300 . ?
C8 C12 1.3946(17) . ?
C8 C9 1.5055(17) . ?
C9 H13 0.9600 . ?
C9 H12 0.9600 . ?
C9 H2 0.9600 . ?
C10 C11 1.5077(17) . ?
C10 H4 0.9600 . ?
C10 H15 0.9600 . ?
C10 H3 0.9600 . ?
C11 C12 1.3933(18) . ?
C11 C14 1.4015(15) . ?
C12 H14 0.9300 . ?
C13 H8 0.9700 . ?
C13 H9 0.9700 . ?
C14 H11 0.9300 . ?
C15 C16 1.4733(15) . ?
C16 C17 1.3970(15) . ?
C16 C20 1.3980(16) . ?
C17 C18 1.3895(15) . ?
C17 H18 0.9300 . ?
C18 C19 1.3968(15) . ?
C18 H17 0.9300 . ?
C19 C21 1.3957(15) . ?
C20 C21 1.3838(16) . ?
C20 H19 0.9300 . ?
C21 H16 0.9300 . ?

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
C3 O2 C4 108.96(8) . . ?
C6 O3 C5 116.85(8) . . ?
C19 O5 H21 110.0(17) . . ?
C15 O6 H61 116.2(18) . . ?
C3 N1 C13 112.50(9) . . ?
C3 N1 H1 122.5(14) . . ?
C13 N1 H1 124.3(14) . . ?
O1 C3 N1 128.42(10) . . ?
O1 C3 O2 120.38(9) . . ?
N1 C3 O2 111.20(9) . . ?
O2 C4 C5 107.75(8) . . ?
O2 C4 C13 104.59(8) . . ?
C5 C4 C13 117.31(9) . . ?
O2 C4 H7 109.0 . . ?
C5 C4 H7 109.0 . . ?
C13 C4 H7 109.0 . . ?
O3 C5 C4 108.14(8) . . ?
O3 C5 H6 110.1 . . ?
C4 C5 H6 110.1 . . ?
O3 C5 H10 110.1 . . ?
C4 C5 H10 110.1 . . ?
H6 C5 H10 108.4 . . ?
O3 C6 C7 114.94(9) . . ?
O3 C6 C14 124.05(9) . . ?
C7 C6 C14 121.01(9) . . ?
C8 C7 C6 120.02(10) . . ?
C8 C7 H5 120.0 . . ?
C6 C7 H5 120.0 . . ?
C7 C8 C12 118.82(10) . . ?
C7 C8 C9 120.29(11) . . ?
C12 C8 C9 120.89(10) . . ?
C8 C9 H13 109.5 . . ?
C8 C9 H12 109.5 . . ?
H13 C9 H12 109.5 . . ?
C8 C9 H2 109.5 . . ?
H13 C9 H2 109.5 . . ?
H12 C9 H2 109.5 . . ?
C11 C10 H4 109.5 . . ?
C11 C10 H15 109.5 . . ?
H4 C10 H15 109.5 . . ?
C11 C10 H3 109.5 . . ?
H4 C10 H3 109.5 . . ?
H15 C10 H3 109.5 . . ?
C12 C11 C14 119.29(10) . . ?
C12 C11 C10 120.81(11) . . ?
C14 C11 C10 119.90(12) . . ?
C11 C12 C8 121.66(10) . . ?
C11 C12 H14 119.2 . . ?
C8 C12 H14 119.2 . . ?
N1 C13 C4 100.76(8) . . ?
N1 C13 H8 111.6 . . ?
C4 C13 H8 111.6 . . ?
N1 C13 H9 111.6 . . ?
C4 C13 H9 111.6 . . ?
H8 C13 H9 109.4 . . ?
C6 C14 C11 119.19(10) . . ?
C6 C14 H11 120.4 . . ?
C11 C14 H11 120.4 . . ?
O4 C15 O6 123.30(11) . . ?
O4 C15 C16 119.48(10) . . ?
O6 C15 C16 117.22(11) . . ?
C17 C16 C20 119.42(10) . . ?
C17 C16 C15 120.61(10) . . ?
C20 C16 C15 119.97(10) . . ?
C18 C17 C16 120.34(10) . . ?
C18 C17 H18 119.8 . . ?
C16 C17 H18 119.8 . . ?
C17 C18 C19 119.71(10) . . ?
C17 C18 H17 120.1 . . ?
C19 C18 H17 120.1 . . ?
O5 C19 C21 117.29(10) . . ?
O5 C19 C18 122.51(10) . . ?
C21 C19 C18 120.20(10) . . ?
C21 C20 C16 120.54(10) . . ?
C21 C20 H19 119.7 . . ?
C16 C20 H19 119.7 . . ?
C20 C21 C19 119.79(10) . . ?
C20 C21 H16 120.1 . . ?
C19 C21 H16 120.1 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C3 O1 -173.95(10) . . . . ?
C13 N1 C3 O2 5.34(12) . . . . ?
C4 O2 C3 O1 -176.11(9) . . . . ?
C4 O2 C3 N1 4.54(11) . . . . ?
C3 O2 C4 C5 -137.22(9) . . . . ?
C3 O2 C4 C13 -11.69(10) . . . . ?
C6 O3 C5 C4 -164.19(8) . . . . ?
O2 C4 C5 O3 68.57(10) . . . . ?
C13 C4 C5 O3 -49.01(12) . . . . ?
C5 O3 C6 C7 178.66(8) . . . . ?
C5 O3 C6 C14 -0.54(14) . . . . ?
O3 C6 C7 C8 -178.09(9) . . . . ?
C14 C6 C7 C8 1.13(16) . . . . ?
C6 C7 C8 C12 0.17(16) . . . . ?
C6 C7 C8 C9 -179.35(10) . . . . ?
C14 C11 C12 C8 0.43(18) . . . . ?
C10 C11 C12 C8 179.77(12) . . . . ?
C7 C8 C12 C11 -0.95(18) . . . . ?
C9 C8 C12 C11 178.57(11) . . . . ?
C3 N1 C13 C4 -11.95(11) . . . . ?
O2 C4 C13 N1 13.56(10) . . . . ?
C5 C4 C13 N1 132.84(9) . . . . ?
O3 C6 C14 C11 177.50(10) . . . . ?
C7 C6 C14 C11 -1.65(16) . . . . ?
C12 C11 C14 C6 0.87(17) . . . . ?
C10 C11 C14 C6 -178.48(11) . . . . ?
O4 C15 C16 C17 9.65(17) . . . . ?
O6 C15 C16 C17 -171.02(11) . . . . ?
O4 C15 C16 C20 -170.28(11) . . . . ?
O6 C15 C16 C20 9.05(16) . . . . ?
C20 C16 C17 C18 -0.67(17) . . . . ?
C15 C16 C17 C18 179.40(10) . . . . ?
C16 C17 C18 C19 0.31(17) . . . . ?
C17 C18 C19 O5 179.41(10) . . . . ?
C17 C18 C19 C21 0.11(16) . . . . ?
C17 C16 C20 C21 0.63(17) . . . . ?
C15 C16 C20 C21 -179.44(10) . . . . ?
C16 C20 C21 C19 -0.22(17) . . . . ?
O5 C19 C21 C20 -179.49(10) . . . . ?
C18 C19 C21 C20 -0.15(17) . . . . ?

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
N1 H1 O1 0.89(2) 2.00(2) 2.8523(12) 161(2) 2_765
O5 H21 O1 0.80(3) 1.88(3) 2.6750(12) 173(2) .
O6 H61 O4 0.97(3) 1.66(3) 2.6162(13) 167(3) 2_475

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.077

