# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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. 
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data_PR111
_database_code_depnum_ccdc_archive 'CCDC 2051074'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;FU Berlin
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 N4 O4'
_chemical_formula_weight         506.55

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'

_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                   9.45250(10)
_cell_length_b                   11.1197(2)
_cell_length_c                   14.54330(10)
_cell_angle_alpha                97.639(4)
_cell_angle_beta                 108.409(4)
_cell_angle_gamma                106.008(3)
_cell_volume                     1352.99(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7292
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      66.55
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   0.8106
_exptl_transmission_factor_max   0.9791
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_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     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17026
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.300
_diffrn_reflns_theta_max         66.750
_diffrn_reflns_theta_full        66.750
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4780
_reflns_number_gt                3725
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0443P)²+0.9403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4780
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C -0.1908(2) 1.49922(19) 0.60640(15) 0.0179(4) Uani 1 1 d . . . . .
C2 C -0.2788(2) 1.57924(19) 0.57469(16) 0.0199(4) Uani 1 1 d . . . . .
H2 H -0.299572 1.632025 0.622228 0.024 Uiso 1 1 calc R U . . .
C3 C -0.3354(2) 1.58239(19) 0.47581(15) 0.0183(4) Uani 1 1 d . . . . .
H3 H -0.395626 1.636634 0.456084 0.022 Uiso 1 1 calc R U . . .
C4 C -0.3056(2) 1.50652(18) 0.40329(15) 0.0168(4) Uani 1 1 d . . . . .
C5 C -0.2137(2) 1.42894(19) 0.43642(15) 0.0183(4) Uani 1 1 d . . . . .
H5 H -0.189084 1.378562 0.389554 0.022 Uiso 1 1 calc R U . . .
C6 C -0.1590(2) 1.42466(19) 0.53484(16) 0.0196(4) Uani 1 1 d . . . . .
H6 H -0.098787 1.370460 0.554770 0.024 Uiso 1 1 calc R U . . .
C7 C -0.1351(2) 1.49273(19) 0.71034(15) 0.0181(4) Uani 1 1 d . . . . .
C8 C -0.3663(2) 1.50579(19) 0.29928(15) 0.0183(4) Uani 1 1 d . . . . .
C11 C -0.4659(2) 1.5765(2) 0.26202(15) 0.0194(4) Uani 1 1 d . . . . .
C12 C -0.3294(3) 1.4321(2) 0.22927(16) 0.0214(5) Uani 1 1 d . . . . .
C15 C -0.0305(3) 1.5533(2) 0.88316(16) 0.0246(5) Uani 1 1 d . . . . .
H15A H -0.088690 1.577170 0.924423 0.030 Uiso 1 1 calc R U . . .
H15B H 0.084744 1.592848 0.921952 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0786(3) 1.4072(2) 0.84922(16) 0.0236(5) Uani 1 1 d . . . . .
H16A H 0.013436 1.378133 0.874368 0.028 Uiso 1 1 calc R U . . .
H16B H -0.162305 1.362801 0.872336 0.028 Uiso 1 1 calc R U . . .
C17 C -0.0080(3) 1.72783(19) 0.78639(16) 0.0209(5) Uani 1 1 d . . . . .
H17A H -0.017864 1.731910 0.717147 0.025 Uiso 1 1 calc R U . . .
H17B H 0.106272 1.760215 0.828385 0.025 Uiso 1 1 calc R U . . .
C18 C -0.2299(3) 1.25286(19) 0.67885(16) 0.0212(5) Uani 1 1 d . . . . .
H18A H -0.298531 1.257542 0.613016 0.025 Uiso 1 1 calc R U . . .
H18B H -0.299572 1.208676 0.711404 0.025 Uiso 1 1 calc R U . . .
C19 C -0.0858(2) 1.81513(19) 0.82294(15) 0.0187(4) Uani 1 1 d . . . . .
C20 C -0.0036(3) 1.9476(2) 0.85241(15) 0.0210(5) Uani 1 1 d . . . . .
H20 H 0.099521 1.979289 0.850734 0.025 Uiso 1 1 calc R U . . .
C21 C -0.0698(3) 2.0332(2) 0.88390(16) 0.0204(5) Uani 1 1 d . . . . .
H21 H -0.011655 2.123005 0.904641 0.024 Uiso 1 1 calc R U . . .
C22 C -0.2219(3) 1.9883(2) 0.88539(15) 0.0200(4) Uani 1 1 d . . . . .
C23 C -0.3048(3) 1.8558(2) 0.85620(16) 0.0218(5) Uani 1 1 d . . . . .
H23 H -0.408395 1.824117 0.857114 0.026 Uiso 1 1 calc R U . . .
C24 C -0.2363(3) 1.7706(2) 0.82590(16) 0.0216(5) Uani 1 1 d . . . . .
H24 H -0.292941 1.680545 0.806931 0.026 Uiso 1 1 calc R U . . .
C25 C -0.2878(3) 2.0851(2) 0.91892(15) 0.0206(5) Uani 1 1 d . . . . .
C26 C -0.5112(3) 2.1307(2) 0.9278(2) 0.0334(6) Uani 1 1 d . . . . .
H26A H -0.503680 2.193787 0.886879 0.050 Uiso 1 1 calc R U . . .
H26B H -0.453708 2.174990 0.998470 0.050 Uiso 1 1 calc R U . . .
H26C H -0.622808 2.087026 0.916248 0.050 Uiso 1 1 calc R U . . .
C27 C -0.1295(3) 1.17321(19) 0.66281(15) 0.0201(5) Uani 1 1 d . . . . .
C28 C 0.0343(3) 1.2252(2) 0.69528(16) 0.0230(5) Uani 1 1 d . . . . .
H28 H 0.086059 1.313932 0.728069 0.028 Uiso 1 1 calc R U . . .
C29 C 0.1234(3) 1.1495(2) 0.68060(16) 0.0224(5) Uani 1 1 d . . . . .
H29 H 0.235393 1.186465 0.703196 0.027 Uiso 1 1 calc R U . . .
C30 C 0.0487(3) 1.0191(2) 0.63268(15) 0.0199(4) Uani 1 1 d . . . . .
C31 C -0.1159(3) 0.9668(2) 0.59825(16) 0.0210(5) Uani 1 1 d . . . . .
H31 H -0.168062 0.878355 0.564450 0.025 Uiso 1 1 calc R U . . .
C32 C -0.2029(3) 1.0429(2) 0.61311(15) 0.0209(5) Uani 1 1 d . . . . .
H32 H -0.315100 1.006316 0.589161 0.025 Uiso 1 1 calc R U . . .
C33 C 0.1388(3) 0.9325(2) 0.62037(15) 0.0209(5) Uani 1 1 d . . . . .
C34 C 0.3911(3) 0.9153(2) 0.65350(19) 0.0309(5) Uani 1 1 d . . . . .
H34A H 0.360358 0.868963 0.584174 0.046 Uiso 1 1 calc R U . . .
H34B H 0.374727 0.853066 0.694194 0.046 Uiso 1 1 calc R U . . .
H34C H 0.503183 0.969145 0.679402 0.046 Uiso 1 1 calc R U . . .
N9 N -0.0751(2) 1.59345(16) 0.78812(13) 0.0191(4) Uani 1 1 d . . . . .
N10 N -0.1381(2) 1.38326(16) 0.73958(13) 0.0193(4) Uani 1 1 d . . . . .
N13 N -0.5476(2) 1.6347(2) 0.23250(15) 0.0298(5) Uani 1 1 d . . . . .
N14 N -0.2970(3) 1.3711(2) 0.17363(15) 0.0342(5) Uani 1 1 d . . . . .
O1 O -0.44238(18) 2.03631(14) 0.90055(12) 0.0291(4) Uani 1 1 d . . . . .
O2 O -0.20995(19) 2.19712(14) 0.95793(12) 0.0293(4) Uani 1 1 d . . . . .
O3 O 0.29623(18) 0.99528(14) 0.65751(12) 0.0263(4) Uani 1 1 d . . . . .
O4 O 0.08059(18) 0.81758(14) 0.58367(12) 0.0274(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.402(3) . ?
C1 C2 1.404(3) . ?
C1 C7 1.454(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.409(3) . ?
C4 C5 1.411(3) . ?
C4 C8 1.436(3) . ?
C5 C6 1.372(3) . ?
C7 N9 1.328(3) . ?
C7 N10 1.338(3) . ?
C8 C12 1.410(3) . ?
C8 C11 1.413(3) . ?
C11 N13 1.158(3) . ?
C12 N14 1.155(3) . ?
C15 N9 1.479(3) . ?
C15 C16 1.525(3) . ?
C16 N10 1.472(3) . ?
C17 N9 1.460(3) . ?
C17 C19 1.506(3) . ?
C18 N10 1.455(3) . ?
C18 C27 1.512(3) . ?
C19 C24 1.387(3) . ?
C19 C20 1.396(3) . ?
C20 C21 1.379(3) . ?
C21 C22 1.394(3) . ?
C22 C23 1.397(3) . ?
C22 C25 1.486(3) . ?
C23 C24 1.386(3) . ?
C25 O2 1.207(3) . ?
C25 O1 1.333(3) . ?
C26 O1 1.453(3) . ?
C27 C28 1.388(3) . ?
C27 C32 1.398(3) . ?
C28 C29 1.386(3) . ?
C29 C30 1.394(3) . ?
C30 C31 1.393(3) . ?
C30 C33 1.479(3) . ?
C31 C32 1.374(3) . ?
C33 O4 1.211(3) . ?
C33 O3 1.346(3) . ?
C34 O3 1.435(3) . ?

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
C6 C1 C2 118.15(19) . . ?
C6 C1 C7 120.73(18) . . ?
C2 C1 C7 121.11(18) . . ?
C3 C2 C1 121.01(19) . . ?
C2 C3 C4 121.13(19) . . ?
C3 C4 C5 117.34(19) . . ?
C3 C4 C8 122.24(18) . . ?
C5 C4 C8 120.42(18) . . ?
C6 C5 C4 121.45(19) . . ?
C5 C6 C1 120.88(19) . . ?
N9 C7 N10 111.32(18) . . ?
N9 C7 C1 124.84(18) . . ?
N10 C7 C1 123.84(18) . . ?
C12 C8 C11 116.99(18) . . ?
C12 C8 C4 120.67(18) . . ?
C11 C8 C4 122.33(18) . . ?
N13 C11 C8 179.3(2) . . ?
N14 C12 C8 178.5(2) . . ?
N9 C15 C16 103.27(17) . . ?
N10 C16 C15 103.17(16) . . ?
N9 C17 C19 113.86(17) . . ?
N10 C18 C27 113.76(18) . . ?
C24 C19 C20 118.7(2) . . ?
C24 C19 C17 123.24(19) . . ?
C20 C19 C17 117.99(19) . . ?
C21 C20 C19 121.0(2) . . ?
C20 C21 C22 120.16(19) . . ?
C21 C22 C23 119.2(2) . . ?
C21 C22 C25 117.77(19) . . ?
C23 C22 C25 123.0(2) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C19 120.77(19) . . ?
O2 C25 O1 123.2(2) . . ?
O2 C25 C22 123.5(2) . . ?
O1 C25 C22 113.25(18) . . ?
C28 C27 C32 118.32(19) . . ?
C28 C27 C18 122.25(19) . . ?
C32 C27 C18 119.43(19) . . ?
C29 C28 C27 120.99(19) . . ?
C28 C29 C30 120.0(2) . . ?
C31 C30 C29 119.3(2) . . ?
C31 C30 C33 118.52(19) . . ?
C29 C30 C33 122.1(2) . . ?
C32 C31 C30 120.08(19) . . ?
C31 C32 C27 121.3(2) . . ?
O4 C33 O3 122.8(2) . . ?
O4 C33 C30 124.9(2) . . ?
O3 C33 C30 112.29(18) . . ?
C7 N9 C17 125.72(17) . . ?
C7 N9 C15 111.04(17) . . ?
C17 N9 C15 120.01(17) . . ?
C7 N10 C18 126.56(18) . . ?
C7 N10 C16 111.14(16) . . ?
C18 N10 C16 119.70(17) . . ?
C25 O1 C26 114.20(17) . . ?
C33 O3 C34 115.07(17) . . ?

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
C6 C1 C2 C3 1.4(3) . . . . ?
C7 C1 C2 C3 -178.1(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C8 178.5(2) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C8 C4 C5 C6 -177.7(2) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C7 C1 C6 C5 178.9(2) . . . . ?
C6 C1 C7 N9 139.3(2) . . . . ?
C2 C1 C7 N9 -41.2(3) . . . . ?
C6 C1 C7 N10 -40.7(3) . . . . ?
C2 C1 C7 N10 138.8(2) . . . . ?
C3 C4 C8 C12 177.76(19) . . . . ?
C5 C4 C8 C12 -2.8(3) . . . . ?
C3 C4 C8 C11 -2.9(3) . . . . ?
C5 C4 C8 C11 176.47(19) . . . . ?
N9 C15 C16 N10 2.2(2) . . . . ?
N9 C17 C19 C24 -20.7(3) . . . . ?
N9 C17 C19 C20 161.22(18) . . . . ?
C24 C19 C20 C21 0.0(3) . . . . ?
C17 C19 C20 C21 178.13(19) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C20 C21 C22 C25 -179.30(19) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C25 C22 C23 C24 -179.9(2) . . . . ?
C22 C23 C24 C19 -0.8(3) . . . . ?
C20 C19 C24 C23 0.9(3) . . . . ?
C17 C19 C24 C23 -177.18(19) . . . . ?
C21 C22 C25 O2 -10.9(3) . . . . ?
C23 C22 C25 O2 168.7(2) . . . . ?
C21 C22 C25 O1 168.33(18) . . . . ?
C23 C22 C25 O1 -12.0(3) . . . . ?
N10 C18 C27 C28 -5.9(3) . . . . ?
N10 C18 C27 C32 174.49(18) . . . . ?
C32 C27 C28 C29 -1.2(3) . . . . ?
C18 C27 C28 C29 179.2(2) . . . . ?
C27 C28 C29 C30 -0.1(3) . . . . ?
C28 C29 C30 C31 1.2(3) . . . . ?
C28 C29 C30 C33 -176.4(2) . . . . ?
C29 C30 C31 C32 -1.1(3) . . . . ?
C33 C30 C31 C32 176.60(19) . . . . ?
C30 C31 C32 C27 -0.2(3) . . . . ?
C28 C27 C32 C31 1.3(3) . . . . ?
C18 C27 C32 C31 -179.08(19) . . . . ?
C31 C30 C33 O4 -1.3(3) . . . . ?
C29 C30 C33 O4 176.4(2) . . . . ?
C31 C30 C33 O3 -179.50(18) . . . . ?
C29 C30 C33 O3 -1.9(3) . . . . ?
N10 C7 N9 C17 159.34(19) . . . . ?
C1 C7 N9 C17 -20.7(3) . . . . ?
N10 C7 N9 C15 -0.1(2) . . . . ?
C1 C7 N9 C15 179.82(19) . . . . ?
C19 C17 N9 C7 123.4(2) . . . . ?
C19 C17 N9 C15 -78.8(2) . . . . ?
C16 C15 N9 C7 -1.4(2) . . . . ?
C16 C15 N9 C17 -162.23(18) . . . . ?
N9 C7 N10 C18 163.25(19) . . . . ?
C1 C7 N10 C18 -16.7(3) . . . . ?
N9 C7 N10 C16 1.8(2) . . . . ?
C1 C7 N10 C16 -178.19(19) . . . . ?
C27 C18 N10 C7 116.4(2) . . . . ?
C27 C18 N10 C16 -83.6(2) . . . . ?
C15 C16 N10 C7 -2.5(2) . . . . ?
C15 C16 N10 C18 -165.45(18) . . . . ?
O2 C25 O1 C26 2.4(3) . . . . ?
C22 C25 O1 C26 -176.81(18) . . . . ?
O4 C33 O3 C34 -1.9(3) . . . . ?
C30 C33 O3 C34 176.31(18) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.051



