# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_V17e
_database_code_depnum_ccdc_archive 'CCDC 2306137'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4CE00408F 2024
loop_
_audit_author_name
_audit_author_address
'Vladimir Chernyshev'
;Lomonosov Moscow State University
Russia
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;

_audit_creation_method           'MRIA, SHELXL-97'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 Cu N2 O6, 0.25(H2 O)'
_chemical_formula_sum            'C14 H16.50 Cu N2 O6.25'
_chemical_formula_weight         376.38
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu -1.9646 0.5888 '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'
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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   12.2970(11)
_cell_length_b                   14.4258(11)
_cell_length_c                   8.5061(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1508.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    561
_cell_measurement_theta_min      4.72
_cell_measurement_theta_max      40.00

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             774
_exptl_absorpt_coefficient_mu    2.382
_exptl_absorpt_correction_type   none
_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 on the non-diffracting silicon plate
;
_pd_spec_mount_mode              reflection # 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                  'light blue' # 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               
;
A.N.Frumkin Institute of Physical Chemistry and Electrochemistry RAS,
Moscow
;

_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  ?
_diffrn_measurement_device       Empyrean
_diffrn_detector_type            ?



_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
_diffrn_radiation_wavelength     1.5418

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

_pd_meas_number_of_points        4297
_pd_meas_2theta_range_min        6.980
_pd_meas_2theta_range_max        80.012
_pd_meas_2theta_range_inc        0.017

# 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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        0.0157
_pd_proc_ls_prof_wR_factor       0.0207
_pd_proc_ls_prof_wR_expected     0.0102

_refine_special_details          
; 
?
;

_refine_ls_R_I_factor            0.055
_refine_ls_structure_factor_coef Inet
_refine_ls_matrix_type           fullcycle
_refine_ls_weighting_scheme      sigma
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_parameters     122
_refine_ls_number_restraints     83
_refine_ls_number_constraints    0

# The following item is the same as CHI, the square root of 'CHI squared = 4.150'
_refine_ls_goodness_of_fit_all   2.034

_refine_ls_restrained_S_all      ?
_refine_ls_restrained_S_obs      ?
_refine_ls_shift/su_max          .002
_refine_ls_shift/su_mean         .000


# 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        6.980
_pd_proc_2theta_range_max        80.012
_pd_proc_2theta_range_inc        0.017

_pd_proc_wavelength              1.5418

_pd_block_diffractogram_id       V17e_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
Cu1 Cu 0.81920(12) 0.41920(8) 0.80699(18) 0.062(1) Uiso 1 1 d . . .
N1 N 0.9502(6) 0.3604(4) 0.7245(9) 0.069(3) Uiso 1 1 d . . .
N2 N 0.8397(7) 0.3219(4) 0.9918(9) 0.068(3) Uiso 1 1 d . . .
C1 C 1.0166(8) 0.4051(5) 0.6091(11) 0.075(4) Uiso 1 1 d . . .
C2 C 0.9749(7) 0.4714(5) 0.5049(12) 0.078(4) Uiso 1 1 d . . .
C3 C 1.0445(8) 0.5174(5) 0.4004(12) 0.074(4) Uiso 1 1 d . . .
H3 H 1.0161 0.5597 0.3289 0.089 Uiso 1 1 calc . . .
C4 C 1.1557(8) 0.5003(5) 0.4028(12) 0.081(4) Uiso 1 1 d . . .
H4 H 1.2022 0.5318 0.3351 0.097 Uiso 1 1 calc . . .
C5 C 1.1962(7) 0.4349(6) 0.5087(11) 0.073(4) Uiso 1 1 d . . .
C6 C 1.1281(7) 0.3873(5) 0.6130(11) 0.072(4) Uiso 1 1 d . . .
H6 H 1.1567 0.3446 0.6836 0.086 Uiso 1 1 calc . . .
C7 C 0.8551(7) 0.4972(5) 0.4906(12) 0.069(4) Uiso 1 1 d . . .
C8 C 1.3150(7) 0.4188(6) 0.5171(11) 0.078(4) Uiso 1 1 d . . .
O1 O 0.7855(5) 0.4691(3) 0.5955(7) 0.071(3) Uiso 1 1 d . . .
O2 O 0.8257(5) 0.5420(4) 0.3681(7) 0.068(3) Uiso 1 1 d . . .
O3 O 1.3770(4) 0.4760(4) 0.4458(8) 0.072(3) Uiso 1 1 d . . .
H3A H 1.4406 0.4606 0.4582 0.108 Uiso 1 1 calc . . .
O4 O 1.3510(5) 0.3549(3) 0.6003(7) 0.067(3) Uiso 1 1 d . . .
C9 C 0.9665(8) 0.2723(5) 0.7753(11) 0.073(4) Uiso 1 1 d . . .
O5 O 1.0451(5) 0.2246(3) 0.7408(6) 0.066(3) Uiso 1 1 d . . .
C10 C 0.8871(8) 0.2409(5) 0.9018(11) 0.068(4) Uiso 1 1 d . . .
H10 H 0.9248 0.1996 0.9753 0.082 Uiso 1 1 calc . . .
C11 C 0.7854(7) 0.1923(6) 0.8394(12) 0.072(4) Uiso 1 1 d . . .
H11A H 0.7741 0.2078 0.7296 0.086 Uiso 1 1 calc . . .
H11B H 0.7933 0.1256 0.8483 0.086 Uiso 1 1 calc . . .
C12 C 0.6897(8) 0.2254(5) 0.9377(11) 0.077(4) Uiso 1 1 d . . .
H12A H 0.6403 0.2623 0.8746 0.092 Uiso 1 1 calc . . .
H12B H 0.6501 0.1731 0.9809 0.092 Uiso 1 1 calc . . .
C13 C 0.7387(8) 0.2828(5) 1.0670(12) 0.068(4) Uiso 1 1 d . . .
H13A H 0.7567 0.2449 1.1575 0.082 Uiso 1 1 calc . . .
H13B H 0.6896 0.3318 1.0995 0.082 Uiso 1 1 calc . . .
C14 C 0.9156(7) 0.3648(5) 1.1007(12) 0.066(4) Uiso 1 1 d . . .
H14A H 0.9774 0.3878 1.0438 0.099 Uiso 1 1 calc . . .
H14B H 0.9392 0.3197 1.1764 0.099 Uiso 1 1 calc . . .
H14C H 0.8804 0.4152 1.1540 0.099 Uiso 1 1 calc . . .
O6 O 0.9136(5) 0.5543(4) 0.9058(8) 0.075(3) Uiso 1 1 d . . .
H6A H 0.9049 0.6028 0.8509 0.112 Uiso 1 1 d . . .
H6B H 0.8748 0.5548 0.9884 0.112 Uiso 1 1 d . . .
O7 O 1.560(2) 0.2963(15) 0.633(3) 0.080 Uiso 0.25(1) 1 d P . .
H7A H 1.4902 0.2911 0.6272 0.120 Uiso 0.25 1 1 calc . .
H7B H 1.5904 0.2776 0.5493 0.120 Uiso 0.25 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
Cu1 O2 1.939(6) 2_665 ?
Cu1 N1 1.951(7) . ?
Cu1 O1 1.981(6) . ?
Cu1 N2 2.122(7) . ?
Cu1 O6 2.419(6) . ?
N1 C9 1.357(10) . ?
N1 C1 1.431(12) . ?
N2 C14 1.454(12) . ?
N2 C13 1.506(12) . ?
N2 C10 1.514(11) . ?
C1 C6 1.395(13) . ?
C1 C2 1.401(12) . ?
C2 C3 1.401(13) . ?
C2 C7 1.524(12) . ?
C3 C4 1.390(13) . ?
C3 H3 0.9304 . ?
C4 C5 1.396(13) . ?
C4 H4 0.9303 . ?
C5 C6 1.400(13) . ?
C5 C8 1.481(12) . ?
C6 H6 0.9303 . ?
C7 O2 1.278(11) . ?
C7 O1 1.301(11) . ?
C8 O4 1.244(10) . ?
C8 O3 1.277(11) . ?
O2 Cu1 1.939(6) 2_664 ?
O3 H3A 0.8202 . ?
C9 O5 1.222(11) . ?
C9 C10 1.522(13) . ?
C10 C11 1.529(13) . ?
C10 H10 0.9799 . ?
C11 C12 1.520(14) . ?
C11 H11A 0.9701 . ?
C11 H11B 0.9700 . ?
C12 C13 1.503(13) . ?
C12 H12A 0.9702 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9701 . ?
C13 H13B 0.9701 . ?
C14 H14A 0.9601 . ?
C14 H14B 0.9597 . ?
C14 H14C 0.9599 . ?
O6 H6A 0.8479 . ?
O6 H6B 0.8495 . ?
O7 H7A 0.8622 . ?
O7 H7B 0.8459 . ?

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
O2 Cu1 N1 168.7(3) 2_665 . ?
O2 Cu1 O1 86.9(2) 2_665 . ?
N1 Cu1 O1 90.2(3) . . ?
O2 Cu1 N2 95.8(3) 2_665 . ?
N1 Cu1 N2 83.1(3) . . ?
O1 Cu1 N2 159.6(2) . . ?
O2 Cu1 O6 96.6(2) 2_665 . ?
N1 Cu1 O6 94.5(3) . . ?
O1 Cu1 O6 97.1(2) . . ?
N2 Cu1 O6 102.6(2) . . ?
C9 N1 C1 123.8(7) . . ?
C9 N1 Cu1 114.5(6) . . ?
C1 N1 Cu1 121.5(5) . . ?
C14 N2 C13 114.7(7) . . ?
C14 N2 C10 113.8(7) . . ?
C13 N2 C10 104.1(6) . . ?
C14 N2 Cu1 105.5(5) . . ?
C13 N2 Cu1 117.7(6) . . ?
C10 N2 Cu1 100.5(5) . . ?
C6 C1 C2 120.0(8) . . ?
C6 C1 N1 117.5(8) . . ?
C2 C1 N1 122.2(8) . . ?
C3 C2 C1 120.0(8) . . ?
C3 C2 C7 115.1(8) . . ?
C1 C2 C7 124.8(8) . . ?
C4 C3 C2 120.5(8) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.7(8) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 121.8(8) . . ?
C4 C5 C8 119.3(8) . . ?
C6 C5 C8 118.8(8) . . ?
C1 C6 C5 118.8(8) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O2 C7 O1 122.0(7) . . ?
O2 C7 C2 117.5(8) . . ?
O1 C7 C2 120.3(8) . . ?
O4 C8 O3 122.5(8) . . ?
O4 C8 C5 119.7(8) . . ?
O3 C8 C5 117.7(7) . . ?
C7 O1 Cu1 126.7(5) . . ?
C7 O2 Cu1 128.6(6) . 2_664 ?
C8 O3 H3A 109.5 . . ?
O5 C9 N1 124.6(8) . . ?
O5 C9 C10 120.6(7) . . ?
N1 C9 C10 114.1(7) . . ?
N2 C10 C9 112.0(6) . . ?
N2 C10 C11 102.4(7) . . ?
C9 C10 C11 114.6(8) . . ?
N2 C10 H10 109.2 . . ?
C9 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C12 C11 C10 107.4(8) . . ?
C12 C11 H11A 110.2 . . ?
C10 C11 H11A 110.3 . . ?
C12 C11 H11B 110.2 . . ?
C10 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C13 C12 C11 105.4(8) . . ?
C13 C12 H12A 110.7 . . ?
C11 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C12 C13 N2 103.1(8) . . ?
C12 C13 H13A 111.1 . . ?
N2 C13 H13A 111.2 . . ?
C12 C13 H13B 111.1 . . ?
N2 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
N2 C14 H14A 109.4 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Cu1 O6 H6A 114.4 . . ?
Cu1 O6 H6B 91.4 . . ?
H6A O6 H6B 112.2 . . ?
H7A O7 H7B 111.6 . . ?

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

O3 H3A O6 0.82 1.86 2.634(8) 157 2_764
O6 H6A O5 0.85 2.02 2.802(8) 153 4_756
O6 H6B O1 0.85 2.20 2.952(9) 148 2_665

_refine_diff_density_max         0.44
_refine_diff_density_min         -0.33
_refine_diff_density_rms         0.23
####################################################################### 
# 
# 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_V30
_database_code_depnum_ccdc_archive 'CCDC 2324603'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4CE00408F 2024
loop_
_audit_author_name
_audit_author_address
'Vladimir Chernyshev'
;Lomonosov Moscow State University
Russia
;
_audit_update_record             
;
2024-01-10 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT340_V30                 
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01342 Ang. 
RESPONSE: This crystal structure has been solved from the laboratory 
X-ray powder diffraction data.
;
# end Validation Reply Form

_audit_creation_method           'MRIA, SHELXL-97'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O5'
_chemical_formula_sum            'C14 H16 N2 O5'
_chemical_formula_weight         292.29
_chemical_absolute_configuration syn

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           orthorhombic
_symmetry_space_group_name_H-M   'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'

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

_cell_length_a                   18.6262(17)
_cell_length_b                   8.5302(9)
_cell_length_c                   17.2181(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2735.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    427
_cell_measurement_theta_min      4.75
_cell_measurement_theta_max      37.49

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_type   none
_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 on the non-diffracting silicon plate
;
_pd_spec_mount_mode              reflection # options are 'reflection' 
# or 'transmission'

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

_pd_char_particle_morphology     needle
_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               
;
A.N.Frumkin Institute of Physical Chemistry and Electrochemistry RAS,
Moscow
;

_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  ?
_diffrn_measurement_device       Empyrean
_diffrn_detector_type            ?



_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
_diffrn_radiation_wavelength     1.5418

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

_pd_meas_number_of_points        4001
_pd_meas_2theta_range_min        7.000
_pd_meas_2theta_range_max        75.000
_pd_meas_2theta_range_inc        0.017

# 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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        0.0275
_pd_proc_ls_prof_wR_factor       0.0358
_pd_proc_ls_prof_wR_expected     0.0118

_refine_special_details          
; 
?
;

_refine_ls_R_I_factor            0.0514
_refine_ls_structure_factor_coef Inet
_refine_ls_matrix_type           fullcycle
_refine_ls_weighting_scheme      sigma
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_parameters     119
_refine_ls_number_restraints     63
_refine_ls_number_constraints    0

# The following item is the same as CHI, the square root of 'CHI squared = 7.322'
_refine_ls_goodness_of_fit_all   2.706

_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        7.000
_pd_proc_2theta_range_max        75.000
_pd_proc_2theta_range_inc        0.017

_pd_proc_wavelength              1.5418

_pd_block_diffractogram_id       V17e_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     ?

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


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 0.1938(2) 0.3114(8) 0.4609(3) 0.068(3) Uiso 1 1 d . . .
O2 O 0.1697(2) 0.4248(8) 0.3515(4) 0.070(2) Uiso 1 1 d . . .
O3 O -0.1975(3) 0.2740(9) 0.3930(3) 0.069(2) Uiso 1 1 d . . .
O4 O -0.1765(2) 0.2076(8) 0.5149(3) 0.066(2) Uiso 1 1 d . . .
H4 H -0.2202 0.1957 0.5152 0.099 Uiso 1 1 calc . . .
O5 O 0.0160(3) 0.2620(9) 0.6670(3) 0.071(2) Uiso 1 1 d . . .
N1 N 0.0907(3) 0.2535(12) 0.5614(4) 0.067(3) Uiso 1 1 d . . .
H1 H 0.1349 0.2411 0.5485 0.080 Uiso 1 1 calc . . .
N2 N 0.1265(4) 0.1992(12) 0.7722(4) 0.070(3) Uiso 1 1 d . . .
H2 H 0.0800 0.2294 0.7785 0.084 Uiso 1 1 calc . . .
C1 C 0.0436(4) 0.2865(13) 0.4992(5) 0.072(4) Uiso 1 1 d . . .
C2 C 0.0709(5) 0.3275(17) 0.4256(5) 0.081(4) Uiso 1 1 d . . .
C3 C 0.0234(4) 0.3514(13) 0.3628(5) 0.074(4) Uiso 1 1 d . . .
H3 H 0.0413 0.3878 0.3157 0.089 Uiso 1 1 calc . . .
C4 C -0.0503(5) 0.3215(14) 0.3700(6) 0.080(4) Uiso 1 1 d . . .
H4A H -0.0808 0.3303 0.3274 0.096 Uiso 1 1 calc . . .
C5 C -0.0767(4) 0.2782(14) 0.4428(5) 0.071(4) Uiso 1 1 d . . .
C6 C -0.0312(5) 0.2582(16) 0.5068(5) 0.078(3) Uiso 1 1 d . . .
H6 H -0.0500 0.2265 0.5543 0.094 Uiso 1 1 calc . . .
C7 C 0.1484(4) 0.3579(16) 0.4118(5) 0.077(5) Uiso 1 1 d . . .
C8 C -0.1567(4) 0.2535(19) 0.4483(6) 0.078(4) Uiso 1 1 d . . .
C9 C 0.0765(4) 0.2382(16) 0.6395(7) 0.079(4) Uiso 1 1 d . . .
C10 C 0.1411(5) 0.1908(17) 0.6891(5) 0.079(4) Uiso 1 1 d . . .
H10 H 0.1800 0.2648 0.6778 0.095 Uiso 1 1 calc . . .
C11 C 0.1694(4) 0.0269(15) 0.6734(6) 0.070(4) Uiso 1 1 d . . .
H11A H 0.2215 0.0259 0.6728 0.084 Uiso 1 1 calc . . .
H11B H 0.1518 -0.0125 0.6241 0.084 Uiso 1 1 calc . . .
C12 C 0.1400(5) -0.0718(14) 0.7418(6) 0.077(5) Uiso 1 1 d . . .
H12A H 0.0932 -0.1153 0.7296 0.092 Uiso 1 1 calc . . .
H12B H 0.1726 -0.1565 0.7549 0.092 Uiso 1 1 calc . . .
C13 C 0.1350(4) 0.0467(16) 0.8074(6) 0.072(5) Uiso 1 1 d . . .
H13A H 0.0942 0.0231 0.8405 0.087 Uiso 1 1 calc . . .
H13B H 0.1783 0.0439 0.8388 0.087 Uiso 1 1 calc . . .
C14 C 0.1734(4) 0.3197(16) 0.8101(5) 0.081(5) Uiso 1 1 d . . .
H14A H 0.1663 0.4193 0.7853 0.121 Uiso 1 1 calc . . .
H14B H 0.2228 0.2890 0.8052 0.121 Uiso 1 1 calc . . .
H14C H 0.1611 0.3280 0.8641 0.121 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 C7 1.260(10) . ?
O2 C7 1.249(12) . ?
O3 C8 1.230(10) . ?
O4 C8 1.267(12) . ?
O4 H4 0.8204 . ?
O5 C9 1.240(9) . ?
N1 C9 1.377(13) . ?
N1 C1 1.413(11) . ?
N1 H1 0.8600 . ?
N2 C13 1.444(16) . ?
N2 C10 1.458(11) . ?
N2 C14 1.498(14) . ?
N2 H2 0.9101 . ?
C1 C2 1.410(13) . ?
C1 C6 1.420(12) . ?
C2 C3 1.412(13) . ?
C2 C7 1.485(12) . ?
C3 C4 1.401(12) . ?
C3 H3 0.9303 . ?
C4 C5 1.396(14) . ?
C4 H4A 0.9301 . ?
C5 C6 1.400(12) . ?
C5 C8 1.508(10) . ?
C6 H6 0.9303 . ?
C9 C10 1.529(13) . ?
C10 C11 1.519(19) . ?
C10 H10 0.9800 . ?
C11 C12 1.547(15) . ?
C11 H11A 0.9703 . ?
C11 H11B 0.9699 . ?
C12 C13 1.519(16) . ?
C12 H12A 0.9699 . ?
C12 H12B 0.9704 . ?
C13 H13A 0.9703 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9598 . ?
C14 H14B 0.9601 . ?
C14 H14C 0.9602 . ?

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
C8 O4 H4 109.4 . . ?
C9 N1 C1 129.8(6) . . ?
C9 N1 H1 115.1 . . ?
C1 N1 H1 115.1 . . ?
C13 N2 C10 110.3(9) . . ?
C13 N2 C14 111.8(7) . . ?
C10 N2 C14 110.6(8) . . ?
C13 N2 H2 108.0 . . ?
C10 N2 H2 108.0 . . ?
C14 N2 H2 108.0 . . ?
C2 C1 N1 120.5(7) . . ?
C2 C1 C6 118.6(8) . . ?
N1 C1 C6 120.4(8) . . ?
C1 C2 C3 119.9(8) . . ?
C1 C2 C7 122.5(8) . . ?
C3 C2 C7 117.5(8) . . ?
C4 C3 C2 121.3(9) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 118.2(8) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
C4 C5 C6 121.7(7) . . ?
C4 C5 C8 116.2(8) . . ?
C6 C5 C8 122.1(8) . . ?
C5 C6 C1 120.0(8) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O2 C7 O1 119.2(7) . . ?
O2 C7 C2 121.4(8) . . ?
O1 C7 C2 119.3(9) . . ?
O3 C8 O4 124.4(7) . . ?
O3 C8 C5 122.8(9) . . ?
O4 C8 C5 112.8(7) . . ?
O5 C9 N1 122.2(8) . . ?
O5 C9 C10 123.0(9) . . ?
N1 C9 C10 114.8(7) . . ?
N2 C10 C11 106.5(9) . . ?
N2 C10 C9 112.9(8) . . ?
C11 C10 C9 114.6(9) . . ?
N2 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C9 C10 H10 107.5 . . ?
C10 C11 C12 104.1(8) . . ?
C10 C11 H11A 111.0 . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11B 111.0 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C11 103.0(9) . . ?
C13 C12 H12A 111.2 . . ?
C11 C12 H12A 111.2 . . ?
C13 C12 H12B 111.1 . . ?
C11 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
N2 C13 C12 107.1(8) . . ?
N2 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
N2 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.4 . . ?

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 0.86 1.96 2.632(8) 134 .
N2 H2 O5 0.91 2.04 2.903(9) 158 4_556
O4 H4 O1 0.82 1.65 2.457(5) 165 6_456

_refine_diff_density_max         0.39
_refine_diff_density_min         -0.35
_refine_diff_density_rms         0.25
