# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_BZMDSLC-II
_database_code_depnum_ccdc_archive 'CCDC 1892488'
loop_
_audit_author_name
_audit_author_address
'Alejandro Pedro Ayala'
;Universidade Federal do Cear?
Brazil
;
_audit_update_record             
;
2019-01-22 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_audit_creation_date             2018-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N3 O4, C7 H6 O3'
_chemical_formula_sum            'C20 H19 N3 O7'
_chemical_formula_weight         413.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.645(3)
_cell_length_b                   21.957(8)
_cell_length_c                   8.674(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.131(11)
_cell_angle_gamma                90
_cell_volume                     2027.0(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1872
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1400 before and 0.0723 after correction. The Ratio of minimum to maximum transmission is 0.9139. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1226
_diffrn_reflns_av_unetI/netI     0.0928
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16752
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         2.525
_diffrn_ambient_temperature      295.85
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1728
_reflns_number_total             3980
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1677
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.001
_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)+(0.0536P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1633
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1A(0.124) H3A(0.141) H5A(0.07) H5B(0.07) H6A(0.074) H6B(0.074)
 H2(0.074) H9(0.083) H13(0.092) H4A(0.116) H4B(0.116) H4C(0.116) H10(0.11)
 H7A(0.105) H12(0.12) H4AA(0.121) H11(0.119) H5AA(0.15) H6AA(0.142)
 Fixed X: H1A(0.634147) H3A(0.657024) H5A(0.28963) H5B(0.420537) H6A(0.383568)
 H6B(0.369093) H2(0.405641) H9(0.756671) H13(0.74803) H4A(0.563597)
 H4B(0.676196) H4C(0.629391) H10(0.971302) H7A(0.883895) H12(0.963064)
 H4AA(0.897506) H11(1.072366) H5AA(1.04971) H6AA(1.046012)
 Fixed Y: H1A(0.490865) H3A(0.66363) H5A(0.333068) H5B(0.306754) H6A(0.287192)
 H6B(0.357337) H2(0.535654) H9(0.375641) H13(0.261945) H4A(0.334997)
 H4B(0.379313) H4C(0.335296) H10(0.388477) H7A(0.497516) H12(0.272544)
 H4AA(0.699453) H11(0.335764) H5AA(0.632917) H6AA(0.532537)
 Fixed Z: H1A(0.885874) H3A(1.02329) H5A(0.548295) H5B(0.599704) H6A(0.340162)
 H6B(0.307281) H2(0.676831) H9(0.394637) H13(0.033861) H4A(0.826576)
 H4B(0.797802) H4C(0.666471) H10(0.364404) H7A(1.102531) H12(0.011808)
 H4AA(1.252329) H11(0.174244) H5AA(1.333287) H6AA(1.257782)
;
_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
O3 O 0.54646(19) 0.33267(10) 0.3577(3) 0.0579(6) Uani 1 1 d . . . . .
O4 O 0.5289(2) 0.28654(11) 0.1288(3) 0.0698(7) Uani 1 1 d . . . . .
O2A O 0.6054(2) 0.59031(11) 0.9327(3) 0.0730(7) Uani 1 1 d . . . . .
N1 N 0.4163(2) 0.39782(12) 0.5976(3) 0.0496(7) Uani 1 1 d . . . . .
O1A O 0.6945(2) 0.49938(12) 0.9421(3) 0.0825(8) Uani 1 1 d . . . . .
H1A H 0.634147 0.490865 0.885874 0.124 Uiso 1 1 calc GR . . . .
O2 O 0.2053(2) 0.42443(14) 0.4099(4) 0.0876(9) Uani 1 1 d . . . . .
N2 N 0.5210(2) 0.46541(13) 0.7396(3) 0.0607(8) Uani 1 1 d . . . . .
O3A O 0.7101(3) 0.68033(13) 1.0786(4) 0.0938(9) Uani 1 1 d . . . . .
H3A H 0.657024 0.663630 1.023290 0.141 Uiso 1 1 calc GR . . . .
N3 N 0.2534(3) 0.46592(17) 0.4837(4) 0.0693(9) Uani 1 1 d . . . . .
O1 O 0.2157(2) 0.51864(13) 0.4804(4) 0.1017(11) Uani 1 1 d . . . . .
C3 C 0.3598(3) 0.45431(15) 0.5809(4) 0.0528(9) Uani 1 1 d . . . . .
C7 C 0.5937(3) 0.31052(15) 0.2263(4) 0.0554(9) Uani 1 1 d . . . . .
C1 C 0.5142(3) 0.40754(16) 0.6950(4) 0.0535(9) Uani 1 1 d . . . . .
C8 C 0.7304(3) 0.31820(15) 0.2174(4) 0.0575(9) Uani 1 1 d . . . . .
C5 C 0.3796(3) 0.33787(15) 0.5373(4) 0.0581(9) Uani 1 1 d . . . . .
H5A H 0.289630 0.333068 0.548295 0.070 Uiso 1 1 calc R . . . .
H5B H 0.420537 0.306754 0.599704 0.070 Uiso 1 1 calc R . . . .
C1A C 0.6902(3) 0.55701(18) 0.9783(4) 0.0593(9) Uani 1 1 d . . . . .
C6 C 0.4112(3) 0.32741(16) 0.3723(4) 0.0614(10) Uani 1 1 d . . . . .
H6A H 0.383568 0.287192 0.340162 0.074 Uiso 1 1 calc R . . . .
H6B H 0.369093 0.357337 0.307281 0.074 Uiso 1 1 calc R . . . .
C2A C 0.7924(3) 0.57803(19) 1.0802(4) 0.0623(10) Uani 1 1 d . . . . .
C2 C 0.4243(3) 0.49445(16) 0.6676(4) 0.0615(10) Uani 1 1 d . . . . .
H2 H 0.405641 0.535654 0.676831 0.074 Uiso 1 1 calc R . . . .
C9 C 0.7975(3) 0.35529(17) 0.3160(5) 0.0691(10) Uani 1 1 d . . . . .
H9 H 0.756671 0.375641 0.394637 0.083 Uiso 1 1 calc R . . . .
C3A C 0.7974(4) 0.6389(2) 1.1250(4) 0.0738(11) Uani 1 1 d . . . . .
C13 C 0.7927(4) 0.28710(18) 0.1016(5) 0.0770(11) Uani 1 1 d . . . . .
H13 H 0.748030 0.261945 0.033861 0.092 Uiso 1 1 calc R . . . .
C4 C 0.6038(3) 0.36007(17) 0.7515(5) 0.0773(12) Uani 1 1 d . . . . .
H4A H 0.563597 0.334997 0.826576 0.116 Uiso 1 1 calc GR . . . .
H4B H 0.676196 0.379313 0.797802 0.116 Uiso 1 1 calc GR . . . .
H4C H 0.629391 0.335296 0.666471 0.116 Uiso 1 1 calc GR . . . .
C10 C 0.9262(4) 0.3626(2) 0.2990(6) 0.0915(14) Uani 1 1 d . . . . .
H10 H 0.971302 0.388477 0.364404 0.110 Uiso 1 1 calc R . . . .
C7A C 0.8865(4) 0.5383(2) 1.1316(5) 0.0876(13) Uani 1 1 d . . . . .
H7A H 0.883895 0.497516 1.102531 0.105 Uiso 1 1 calc R . . . .
C12 C 0.9211(5) 0.2938(2) 0.0879(6) 0.1001(15) Uani 1 1 d . . . . .
H12 H 0.963064 0.272544 0.011808 0.120 Uiso 1 1 calc R . . . .
C4A C 0.8943(5) 0.6590(3) 1.2209(5) 0.1005(16) Uani 1 1 d . . . . .
H4AA H 0.897506 0.699453 1.252329 0.121 Uiso 1 1 calc R . . . .
C11 C 0.9861(4) 0.3313(2) 0.1851(6) 0.0995(15) Uani 1 1 d . . . . .
H11 H 1.072366 0.335764 0.174244 0.119 Uiso 1 1 calc R . . . .
C5A C 0.9848(5) 0.6191(4) 1.2690(6) 0.125(2) Uani 1 1 d . . . . .
H5AA H 1.049710 0.632917 1.333287 0.150 Uiso 1 1 calc R . . . .
C6A C 0.9827(4) 0.5589(3) 1.2247(6) 0.1181(19) Uani 1 1 d . . . . .
H6AA H 1.046012 0.532537 1.257782 0.142 Uiso 1 1 calc R . . . .


_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
O3 C7 1.345(4) . ?
O3 C6 1.453(3) . ?
O4 C7 1.202(4) . ?
O2A C1A 1.221(4) . ?
N1 C3 1.385(4) . ?
N1 C1 1.345(4) . ?
N1 C5 1.467(4) . ?
O1A H1A 0.8200 . ?
O1A C1A 1.305(4) . ?
O2 N3 1.220(4) . ?
N2 C1 1.330(4) . ?
N2 C2 1.353(4) . ?
O3A H3A 0.8200 . ?
O3A C3A 1.357(5) . ?
N3 O1 1.226(4) . ?
N3 C3 1.421(4) . ?
C3 C2 1.339(4) . ?
C7 C8 1.469(5) . ?
C1 C4 1.489(4) . ?
C8 C9 1.371(5) . ?
C8 C13 1.393(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.494(4) . ?
C1A C2A 1.463(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2A C3A 1.392(5) . ?
C2A C7A 1.396(5) . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.390(5) . ?
C3A C4A 1.385(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.382(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.372(6) . ?
C7A H7A 0.9300 . ?
C7A C6A 1.368(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.358(6) . ?
C4A H4AA 0.9300 . ?
C4A C5A 1.360(7) . ?
C11 H11 0.9300 . ?
C5A H5AA 0.9300 . ?
C5A C6A 1.377(7) . ?
C6A H6AA 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
C7 O3 C6 115.7(3) . . ?
C3 N1 C5 130.9(3) . . ?
C1 N1 C3 104.7(3) . . ?
C1 N1 C5 124.3(3) . . ?
C1A O1A H1A 109.5 . . ?
C1 N2 C2 106.2(3) . . ?
C3A O3A H3A 109.5 . . ?
O2 N3 O1 124.0(3) . . ?
O2 N3 C3 119.9(3) . . ?
O1 N3 C3 116.1(3) . . ?
N1 C3 N3 124.2(3) . . ?
C2 C3 N1 108.3(3) . . ?
C2 C3 N3 127.5(3) . . ?
O3 C7 C8 113.0(3) . . ?
O4 C7 O3 122.4(3) . . ?
O4 C7 C8 124.6(3) . . ?
N1 C1 C4 125.4(3) . . ?
N2 C1 N1 111.8(3) . . ?
N2 C1 C4 122.8(3) . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 C13 119.5(3) . . ?
C13 C8 C7 117.9(3) . . ?
N1 C5 H5A 108.6 . . ?
N1 C5 H5B 108.6 . . ?
N1 C5 C6 114.6(3) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
O2A C1A O1A 122.1(3) . . ?
O2A C1A C2A 122.9(4) . . ?
O1A C1A C2A 115.0(3) . . ?
O3 C6 C5 108.3(3) . . ?
O3 C6 H6A 110.0 . . ?
O3 C6 H6B 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C3A C2A C1A 119.7(4) . . ?
C3A C2A C7A 119.2(4) . . ?
C7A C2A C1A 121.1(4) . . ?
N2 C2 H2 125.5 . . ?
C3 C2 N2 109.0(3) . . ?
C3 C2 H2 125.5 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.3(4) . . ?
C10 C9 H9 119.9 . . ?
O3A C3A C2A 122.6(4) . . ?
O3A C3A C4A 117.5(5) . . ?
C4A C3A C2A 119.9(5) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 C8 119.7(4) . . ?
C12 C13 H13 120.2 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(4) . . ?
C11 C10 H10 120.3 . . ?
C2A C7A H7A 119.8 . . ?
C6A C7A C2A 120.4(5) . . ?
C6A C7A H7A 119.8 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.9 . . ?
C3A C4A H4AA 120.2 . . ?
C5A C4A C3A 119.6(5) . . ?
C5A C4A H4AA 120.2 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C4A C5A H5AA 119.2 . . ?
C4A C5A C6A 121.6(5) . . ?
C6A C5A H5AA 119.2 . . ?
C7A C6A C5A 119.4(5) . . ?
C7A C6A H6AA 120.3 . . ?
C5A C6A H6AA 120.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_BZMDFMA-II
_database_code_depnum_ccdc_archive 'CCDC 1892489'
loop_
_audit_author_name
_audit_author_address
'Alejandro Pedro Ayala'
;Universidade Federal do Ceara
Brazil
;
_audit_update_record             
;
2023-04-30 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_audit_creation_date             2018-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N3 O4, C2 H2 O2'
_chemical_formula_sum            'C15 H15 N3 O6'
_chemical_formula_weight         333.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.2928(5)
_cell_length_b                   17.0257(9)
_cell_length_c                   25.6078(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3179.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5143
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.00
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.2007 before and 0.0997 after correction. The Ratio of minimum to maximum transmission is 0.7191. The λ/2 correction factor is Not present.'
_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    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.105
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1521
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            60358
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.095
_diffrn_reflns_theta_min         2.521
_diffrn_ambient_temperature      296
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1673
_reflns_number_total             3511
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.007
_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)+(0.0698P)²+1.0386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1771
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1A(0.111) H2A(0.07) H9(0.076) H2(0.081) H13(0.087) H10(0.087)
 H11(0.091) H5A(0.084) H5B(0.084) H6A(0.09) H6B(0.09) H12(0.096) H4A(0.121)
 H4B(0.121) H4C(0.121)
 Fixed X: H1A(0.505238) H2A(0.344905) H9(0.786862) H2(0.444577) H13(0.883611)
 H10(0.692373) H11(0.690708) H5A(1.093767) H5B(1.032103) H6A(0.853239)
 H6B(1.062678) H12(0.79085) H4A(0.974383) H4B(0.881157) H4C(1.041517)
 Fixed Y: H1A(0.797676) H2A(0.976966) H9(0.809417) H2(0.623112) H13(0.760416)
 H10(0.933416) H11(0.970386) H5A(0.64046) H5B(0.552663) H6A(0.566016)
 H6B(0.580584) H12(0.885038) H4A(0.775718) H4B(0.815585) H4C(0.755522)
 Fixed Z: H1A(0.539093) H2A(0.526576) H9(0.698665) H2(0.553112) H13(0.84897)
 H10(0.721916) H11(0.80853) H5A(0.625845) H5B(0.620134) H6A(0.696648)
 H6B(0.708125) H12(0.871565) H4A(0.622622) H4B(0.574246) H4C(0.566037)
;
_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
O3 O 0.9151(3) 0.67921(11) 0.70642(8) 0.0688(6) Uani 1 1 d . . . . .
O1A O 0.4574(3) 0.84107(11) 0.54173(8) 0.0743(6) Uani 1 1 d . . . . .
H1A H 0.505238 0.797676 0.539093 0.111 Uiso 1 1 calc R . . . .
N1 N 0.8329(3) 0.62930(12) 0.60195(9) 0.0562(6) Uani 1 1 d . . . . .
O2A O 0.6815(4) 0.87497(13) 0.48893(11) 0.0980(9) Uani 1 1 d . . . . .
N2 N 0.6376(4) 0.70882(13) 0.56252(10) 0.0652(7) Uani 1 1 d . . . . .
O2 O 0.7707(4) 0.46776(12) 0.62028(10) 0.0948(8) Uani 1 1 d . . . . .
O4 O 0.9295(4) 0.63897(14) 0.78916(9) 0.0990(9) Uani 1 1 d . . . . .
N3 N 0.6477(5) 0.50611(15) 0.59975(11) 0.0765(8) Uani 1 1 d . . . . .
C2A C 0.4593(4) 0.96993(14) 0.51125(11) 0.0585(7) Uani 1 1 d . . . . .
H2A H 0.344905 0.976966 0.526576 0.070 Uiso 1 1 calc R . . . .
C1 C 0.8020(4) 0.70309(15) 0.58437(11) 0.0586(8) Uani 1 1 d . . . . .
C8 C 0.8435(4) 0.77140(16) 0.77108(12) 0.0587(7) Uani 1 1 d . . . . .
C1A C 0.5460(5) 0.89134(16) 0.51272(12) 0.0602(8) Uani 1 1 d . . . . .
O1 O 0.5016(5) 0.47842(15) 0.58607(14) 0.1230(11) Uani 1 1 d . . . . .
C3 C 0.6756(4) 0.58759(15) 0.59029(11) 0.0585(8) Uani 1 1 d . . . . .
C9 C 0.7869(4) 0.82412(17) 0.73364(12) 0.0637(8) Uani 1 1 d . . . . .
H9 H 0.786862 0.809417 0.698665 0.076 Uiso 1 1 calc R . . . .
C7 C 0.9005(4) 0.69077(18) 0.75806(13) 0.0657(8) Uani 1 1 d . . . . .
C2 C 0.5598(5) 0.63656(16) 0.56581(12) 0.0679(8) Uani 1 1 d . . . . .
H2 H 0.444577 0.623112 0.553112 0.081 Uiso 1 1 calc R . . . .
C13 C 0.8447(4) 0.7951(2) 0.82321(13) 0.0727(9) Uani 1 1 d . . . . .
H13 H 0.883611 0.760416 0.848970 0.087 Uiso 1 1 calc R . . . .
C10 C 0.7306(4) 0.89823(18) 0.74748(14) 0.0724(9) Uani 1 1 d . . . . .
H10 H 0.692373 0.933416 0.721916 0.087 Uiso 1 1 calc R . . . .
C11 C 0.7306(5) 0.9204(2) 0.79920(15) 0.0762(9) Uani 1 1 d . . . . .
H11 H 0.690708 0.970386 0.808530 0.091 Uiso 1 1 calc R . . . .
C5 C 0.9937(5) 0.60413(17) 0.63215(12) 0.0699(9) Uani 1 1 d . . . . .
H5A H 1.093767 0.640460 0.625845 0.084 Uiso 1 1 calc R . . . .
H5B H 1.032103 0.552663 0.620134 0.084 Uiso 1 1 calc R . . . .
C6 C 0.9562(5) 0.60050(17) 0.68967(12) 0.0753(10) Uani 1 1 d . . . . .
H6A H 0.853239 0.566016 0.696648 0.090 Uiso 1 1 calc R . . . .
H6B H 1.062678 0.580584 0.708125 0.090 Uiso 1 1 calc R . . . .
C12 C 0.7889(5) 0.8695(2) 0.83676(14) 0.0804(10) Uani 1 1 d . . . . .
H12 H 0.790850 0.885038 0.871565 0.096 Uiso 1 1 calc R . . . .
C4 C 0.9366(5) 0.76822(16) 0.58706(14) 0.0804(10) Uani 1 1 d . . . . .
H4A H 0.974383 0.775718 0.622622 0.121 Uiso 1 1 calc GR . . . .
H4B H 0.881157 0.815585 0.574246 0.121 Uiso 1 1 calc GR . . . .
H4C H 1.041517 0.755522 0.566037 0.121 Uiso 1 1 calc GR . . . .


_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
O3 C7 1.341(3) . ?
O3 C6 1.439(3) . ?
O1A H1A 0.8200 . ?
O1A C1A 1.305(3) . ?
N1 C1 1.353(3) . ?
N1 C3 1.382(3) . ?
N1 C5 1.469(4) . ?
O2A C1A 1.194(3) . ?
N2 C1 1.327(4) . ?
N2 C2 1.357(4) . ?
O2 N3 1.228(3) . ?
O4 C7 1.207(3) . ?
N3 O1 1.217(4) . ?
N3 C3 1.423(4) . ?
C2A C2A 1.316(5) 5_676 ?
C2A H2A 0.9300 . ?
C2A C1A 1.480(4) . ?
C1 C4 1.483(4) . ?
C8 C9 1.376(4) . ?
C8 C7 1.473(4) . ?
C8 C13 1.395(4) . ?
C3 C2 1.342(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(4) . ?
C2 H2 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.374(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.363(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.499(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C12 H12 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 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
C7 O3 C6 116.6(2) . . ?
C1A O1A H1A 109.5 . . ?
C1 N1 C3 105.5(2) . . ?
C1 N1 C5 125.4(2) . . ?
C3 N1 C5 128.8(2) . . ?
C1 N2 C2 106.5(2) . . ?
O2 N3 C3 119.2(3) . . ?
O1 N3 O2 123.8(3) . . ?
O1 N3 C3 117.0(3) . . ?
C2A C2A H2A 119.3 5_676 . ?
C2A C2A C1A 121.5(4) 5_676 . ?
C1A C2A H2A 119.3 . . ?
N1 C1 C4 124.6(3) . . ?
N2 C1 N1 111.1(2) . . ?
N2 C1 C4 124.3(3) . . ?
C9 C8 C7 122.3(3) . . ?
C9 C8 C13 118.7(3) . . ?
C13 C8 C7 119.0(3) . . ?
O1A C1A C2A 113.3(3) . . ?
O2A C1A O1A 123.2(3) . . ?
O2A C1A C2A 123.5(3) . . ?
N1 C3 N3 125.7(3) . . ?
C2 C3 N1 107.7(2) . . ?
C2 C3 N3 126.5(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
O3 C7 C8 112.5(3) . . ?
O4 C7 O3 122.0(3) . . ?
O4 C7 C8 125.5(3) . . ?
N2 C2 H2 125.4 . . ?
C3 C2 N2 109.2(3) . . ?
C3 C2 H2 125.4 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
N1 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
N1 C5 C6 112.6(3) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
O3 C6 C5 107.0(2) . . ?
O3 C6 H6A 110.3 . . ?
O3 C6 H6B 110.3 . . ?
C5 C6 H6A 110.3 . . ?
C5 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
