# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_DF
_database_code_depnum_ccdc_archive 'CCDC 1828487'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-08-07 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         ?
_chemical_formula_sum            'C24 H18 Cl F N2 O3'
_chemical_formula_weight         436.85

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.474(3)
_cell_length_b                   11.271(3)
_cell_length_c                   17.518(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.136(9)
_cell_angle_gamma                90
_cell_volume                     2056.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.15

_exptl_crystal_description       Block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            74936
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.823
_diffrn_reflns_theta_max         30.584
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6283
_reflns_number_gt                4065
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0410P)²+0.8737P] 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         6283
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_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
Cl1 Cl 0.01769(5) 0.67777(6) 0.04469(3) 0.0782(2) Uani 1 1 d . . . . .
O3 O 0.46768(10) 0.56060(10) 0.33249(6) 0.0391(3) Uani 1 1 d . . . . .
F1 F 1.18330(12) 0.61291(14) 0.89219(7) 0.0828(4) Uani 1 1 d . . . . .
O2 O 0.46833(11) 0.35006(10) 0.40745(7) 0.0440(3) Uani 1 1 d . . . . .
N1 N 0.83923(14) 0.55060(14) 0.63315(8) 0.0454(4) Uani 1 1 d . . . . .
N2 N 0.40665(14) 0.41457(13) 0.11277(8) 0.0460(4) Uani 1 1 d . . . . .
C22 C 0.14863(15) 0.62987(16) 0.10675(10) 0.0433(4) Uani 1 1 d . . . . .
C23 C 0.16814(16) 0.68288(16) 0.17931(10) 0.0437(4) Uani 1 1 d . . . . .
H23 H 0.114068 0.743191 0.192569 0.052 Uiso 1 1 calc R U . . .
C24 C 0.26751(15) 0.64509(14) 0.23049(9) 0.0372(3) Uani 1 1 d . . . . .
H24 H 0.280705 0.679780 0.278857 0.045 Uiso 1 1 calc R U . . .
C18 C 0.35020(13) 0.55402(12) 0.21065(8) 0.0296(3) Uani 1 1 d . . . . .
C16 C 0.45393(14) 0.50913(13) 0.26169(8) 0.0306(3) Uani 1 1 d . . . . .
C12 C 0.57197(14) 0.52912(14) 0.38581(9) 0.0345(3) Uani 1 1 d . . . . .
C13 C 0.56842(14) 0.42442(14) 0.42740(9) 0.0351(3) Uani 1 1 d . . . . .
C9 C 0.66606(15) 0.40481(15) 0.48715(9) 0.0390(4) Uani 1 1 d . . . . .
H9 H 0.666161 0.335156 0.515609 0.047 Uiso 1 1 calc R U . . .
C8 C 0.76247(15) 0.48765(16) 0.50446(9) 0.0403(4) Uani 1 1 d . . . . .
C7 C 0.86164(17) 0.46941(18) 0.57289(10) 0.0499(5) Uani 1 1 d . . . . .
H7A H 0.856917 0.388538 0.591322 0.060 Uiso 1 1 calc R U . . .
H7B H 0.946940 0.482111 0.557653 0.060 Uiso 1 1 calc R U . . .
C6 C 0.92572(14) 0.56149(14) 0.69823(9) 0.0352(3) Uani 1 1 d . . . . .
C5 C 0.90033(15) 0.63675(15) 0.75743(9) 0.0384(4) Uani 1 1 d . . . . .
C2 C 0.98338(18) 0.65454(17) 0.82259(10) 0.0478(4) Uani 1 1 d . . . . .
H2 H 0.962893 0.705768 0.861075 0.057 Uiso 1 1 calc R U . . .
C1 C 1.09792(18) 0.59382(19) 0.82883(10) 0.0509(5) Uani 1 1 d . . . . .
C20 C 0.33008(14) 0.50215(14) 0.13680(9) 0.0342(3) Uani 1 1 d . . . . .
C21 C 0.22572(16) 0.54250(15) 0.08479(9) 0.0419(4) Uani 1 1 d . . . . .
H21 H 0.210457 0.509224 0.036092 0.050 Uiso 1 1 calc R U . . .
C19 C 0.50167(17) 0.37857(16) 0.16300(10) 0.0461(4) Uani 1 1 d . . . . .
H19 H 0.554688 0.319236 0.147213 0.055 Uiso 1 1 calc R U . . .
C17 C 0.52992(15) 0.42158(14) 0.23792(9) 0.0376(4) Uani 1 1 d . . . . .
H17 H 0.598319 0.391315 0.270326 0.045 Uiso 1 1 calc R U . . .
C10 C 0.76519(16) 0.58941(16) 0.46062(10) 0.0447(4) Uani 1 1 d . . . . .
H10 H 0.831274 0.644044 0.471127 0.054 Uiso 1 1 calc R U . . .
C11 C 0.66962(16) 0.61029(15) 0.40097(10) 0.0409(4) Uani 1 1 d . . . . .
H11 H 0.671525 0.678680 0.371413 0.049 Uiso 1 1 calc R U . . .
C3 C 1.12893(17) 0.51771(18) 0.77379(11) 0.0507(5) Uani 1 1 d . . . . .
H3 H 1.206644 0.477085 0.779639 0.061 Uiso 1 1 calc R U . . .
C4 C 1.04305(16) 0.50122(17) 0.70853(10) 0.0437(4) Uani 1 1 d . . . . .
H4 H 1.064086 0.448855 0.670795 0.052 Uiso 1 1 calc R U . . .
C14 C 0.47196(17) 0.23501(15) 0.44354(11) 0.0464(4) Uani 1 1 d . . . . .
H14A H 0.462853 0.243031 0.497824 0.056 Uiso 1 1 calc R U . . .
H14B H 0.553134 0.196152 0.438118 0.056 Uiso 1 1 calc R U . . .
C15 C 0.3633(2) 0.16377(18) 0.40478(14) 0.0632(6) Uani 1 1 d . . . . .
H15A H 0.363211 0.086370 0.427657 0.095 Uiso 1 1 calc R U . . .
H15B H 0.283563 0.202930 0.410629 0.095 Uiso 1 1 calc R U . . .
H15C H 0.373458 0.156252 0.351179 0.095 Uiso 1 1 calc R U . . .
F2 F 0.78701(10) 0.69642(10) 0.74955(6) 0.0556(3) Uani 1 1 d . . . . .
H100 H 0.763(2) 0.5772(17) 0.6346(11) 0.050(5) Uiso 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
Cl1 C22 1.7423(16) . ?
O3 C16 1.3628(18) . ?
O3 C12 1.4048(17) . ?
F1 C1 1.3660(19) . ?
O2 C13 1.3583(19) . ?
O2 C14 1.441(2) . ?
N1 C6 1.3837(19) . ?
N1 C7 1.435(2) . ?
N1 H100 0.86(2) . ?
N2 C19 1.320(2) . ?
N2 C20 1.366(2) . ?
C22 C21 1.355(2) . ?
C22 C23 1.400(2) . ?
C23 C24 1.367(2) . ?
C23 H23 0.9300 . ?
C24 C18 1.410(2) . ?
C24 H24 0.9300 . ?
C18 C20 1.415(2) . ?
C18 C16 1.4242(19) . ?
C16 C17 1.361(2) . ?
C12 C11 1.377(2) . ?
C12 C13 1.389(2) . ?
C13 C9 1.401(2) . ?
C9 C8 1.385(2) . ?
C9 H9 0.9300 . ?
C8 C10 1.382(3) . ?
C8 C7 1.514(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C5 1.387(2) . ?
C6 C4 1.399(2) . ?
C5 F2 1.3584(19) . ?
C5 C2 1.374(2) . ?
C2 C1 1.375(3) . ?
C2 H2 0.9300 . ?
C1 C3 1.356(3) . ?
C20 C21 1.421(2) . ?
C21 H21 0.9300 . ?
C19 C17 1.401(2) . ?
C19 H19 0.9300 . ?
C17 H17 0.9300 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C14 C15 1.495(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C16 O3 C12 119.78(12) . . ?
C13 O2 C14 117.31(12) . . ?
C6 N1 C7 121.23(14) . . ?
C6 N1 H100 118.4(13) . . ?
C7 N1 H100 118.1(13) . . ?
C19 N2 C20 116.24(14) . . ?
C21 C22 C23 122.31(15) . . ?
C21 C22 Cl1 120.08(13) . . ?
C23 C22 Cl1 117.60(13) . . ?
C24 C23 C22 119.32(15) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C18 120.64(15) . . ?
C23 C24 H24 119.7 . . ?
C18 C24 H24 119.7 . . ?
C24 C18 C20 119.39(13) . . ?
C24 C18 C16 123.45(14) . . ?
C20 C18 C16 117.15(13) . . ?
C17 C16 O3 125.37(13) . . ?
C17 C16 C18 119.83(14) . . ?
O3 C16 C18 114.80(13) . . ?
C11 C12 C13 121.62(14) . . ?
C11 C12 O3 117.98(14) . . ?
C13 C12 O3 120.04(14) . . ?
O2 C13 C12 116.89(13) . . ?
O2 C13 C9 125.22(15) . . ?
C12 C13 C9 117.87(15) . . ?
C8 C9 C13 120.96(16) . . ?
C8 C9 H9 119.5 . . ?
C13 C9 H9 119.5 . . ?
C10 C8 C9 119.71(14) . . ?
C10 C8 C7 119.97(16) . . ?
C9 C8 C7 120.28(17) . . ?
N1 C7 C8 110.09(14) . . ?
N1 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
N1 C6 C5 120.62(14) . . ?
N1 C6 C4 123.50(15) . . ?
C5 C6 C4 115.88(14) . . ?
F2 C5 C2 118.75(16) . . ?
F2 C5 C6 117.51(14) . . ?
C2 C5 C6 123.74(16) . . ?
C5 C2 C1 117.57(17) . . ?
C5 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C3 C1 F1 119.46(17) . . ?
C3 C1 C2 122.11(16) . . ?
F1 C1 C2 118.42(18) . . ?
N2 C20 C18 123.05(14) . . ?
N2 C20 C21 118.05(14) . . ?
C18 C20 C21 118.90(14) . . ?
C22 C21 C20 119.44(15) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
N2 C19 C17 125.94(16) . . ?
N2 C19 H19 117.0 . . ?
C17 C19 H19 117.0 . . ?
C16 C17 C19 117.77(14) . . ?
C16 C17 H17 121.1 . . ?
C19 C17 H17 121.1 . . ?
C8 C10 C11 120.20(16) . . ?
C8 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.59(16) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C1 C3 C4 119.12(17) . . ?
C1 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C6 121.57(17) . . ?
C3 C4 H4 119.2 . . ?
C6 C4 H4 119.2 . . ?
O2 C14 C15 107.51(14) . . ?
O2 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O2 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C21 C22 C23 C24 -0.6(3) . . . . ?
Cl1 C22 C23 C24 177.98(14) . . . . ?
C22 C23 C24 C18 0.3(3) . . . . ?
C23 C24 C18 C20 0.4(2) . . . . ?
C23 C24 C18 C16 -178.83(15) . . . . ?
C12 O3 C16 C17 4.2(2) . . . . ?
C12 O3 C16 C18 -175.68(13) . . . . ?
C24 C18 C16 C17 -179.55(15) . . . . ?
C20 C18 C16 C17 1.2(2) . . . . ?
C24 C18 C16 O3 0.4(2) . . . . ?
C20 C18 C16 O3 -178.86(13) . . . . ?
C16 O3 C12 C11 107.41(17) . . . . ?
C16 O3 C12 C13 -79.33(19) . . . . ?
C14 O2 C13 C12 172.49(15) . . . . ?
C14 O2 C13 C9 -8.8(2) . . . . ?
C11 C12 C13 O2 -179.55(15) . . . . ?
O3 C12 C13 O2 7.4(2) . . . . ?
C11 C12 C13 C9 1.7(2) . . . . ?
O3 C12 C13 C9 -171.35(14) . . . . ?
O2 C13 C9 C8 -178.24(15) . . . . ?
C12 C13 C9 C8 0.4(2) . . . . ?
C13 C9 C8 C10 -2.2(2) . . . . ?
C13 C9 C8 C7 175.44(15) . . . . ?
C6 N1 C7 C8 -172.17(16) . . . . ?
C10 C8 C7 N1 70.1(2) . . . . ?
C9 C8 C7 N1 -107.58(19) . . . . ?
C7 N1 C6 C5 -177.34(17) . . . . ?
C7 N1 C6 C4 3.9(3) . . . . ?
N1 C6 C5 F2 1.4(2) . . . . ?
C4 C6 C5 F2 -179.74(15) . . . . ?
N1 C6 C5 C2 -178.03(17) . . . . ?
C4 C6 C5 C2 0.8(2) . . . . ?
F2 C5 C2 C1 -179.45(16) . . . . ?
C6 C5 C2 C1 0.0(3) . . . . ?
C5 C2 C1 C3 -0.8(3) . . . . ?
C5 C2 C1 F1 178.17(17) . . . . ?
C19 N2 C20 C18 0.8(2) . . . . ?
C19 N2 C20 C21 -179.27(16) . . . . ?
C24 C18 C20 N2 179.20(15) . . . . ?
C16 C18 C20 N2 -1.5(2) . . . . ?
C24 C18 C20 C21 -0.7(2) . . . . ?
C16 C18 C20 C21 178.54(14) . . . . ?
C23 C22 C21 C20 0.2(3) . . . . ?
Cl1 C22 C21 C20 -178.30(13) . . . . ?
N2 C20 C21 C22 -179.51(16) . . . . ?
C18 C20 C21 C22 0.4(2) . . . . ?
C20 N2 C19 C17 0.3(3) . . . . ?
O3 C16 C17 C19 179.82(15) . . . . ?
C18 C16 C17 C19 -0.2(2) . . . . ?
N2 C19 C17 C16 -0.6(3) . . . . ?
C9 C8 C10 C11 1.9(3) . . . . ?
C7 C8 C10 C11 -175.72(16) . . . . ?
C13 C12 C11 C10 -2.0(2) . . . . ?
O3 C12 C11 C10 171.20(15) . . . . ?
C8 C10 C11 C12 0.1(3) . . . . ?
F1 C1 C3 C4 -178.26(18) . . . . ?
C2 C1 C3 C4 0.7(3) . . . . ?
C1 C3 C4 C6 0.2(3) . . . . ?
N1 C6 C4 C3 177.90(17) . . . . ?
C5 C6 C4 C3 -0.9(3) . . . . ?
C13 O2 C14 C15 -171.99(15) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_PT
_database_code_depnum_ccdc_archive 'CCDC 1828488'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-08-07 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         ?
_chemical_formula_sum            'C25 H23 N2 O2 Cl1'
_chemical_formula_weight         418.92

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'
Cl Cl 0.1484 0.1585 '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                   5.350(4)
_cell_length_b                   14.080(11)
_cell_length_c                   14.717(11)
_cell_angle_alpha                101.00(3)
_cell_angle_beta                 90.44(3)
_cell_angle_gamma                97.24(3)
_cell_volume                     1078.9(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.15

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Transparent
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            29991
_diffrn_reflns_av_unetI/netI     0.2460
_diffrn_reflns_av_R_equivalents  0.2045
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.034
_diffrn_reflns_theta_max         32.093
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             6626
_reflns_number_gt                2450
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.2000P)²] 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         6626
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3659
_refine_ls_R_factor_gt           0.1973
_refine_ls_wR_factor_ref         0.4426
_refine_ls_wR_factor_gt          0.3719
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.000
_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
Cl1 Cl 0.1997(4) 0.96873(14) 0.33893(12) 0.0753(6) Uani 1 1 d . . . . .
O1 O 0.5721(6) 0.7045(3) 0.6333(2) 0.0486(10) Uani 1 1 d . . . . .
O2 O 0.9799(8) 0.7857(3) 0.7401(3) 0.0578(11) Uani 1 1 d . . . . .
N1 N 0.9809(10) 0.3740(4) 0.8237(4) 0.0580(14) Uani 1 1 d . . . . .
C1 C 0.3043(13) 0.1539(7) 1.0309(6) 0.089(2) Uani 1 1 d . . . . .
H1A H 0.340397 0.087612 1.019526 0.133 Uiso 1 1 calc R U . . .
H1B H 0.324368 0.180674 1.095991 0.133 Uiso 1 1 calc R U . . .
H1C H 0.134158 0.155446 1.010667 0.133 Uiso 1 1 calc R U . . .
C2 C 0.4847(11) 0.2137(5) 0.9780(4) 0.0585(16) Uani 1 1 d . . . . .
C3 C 0.6644(11) 0.1705(5) 0.9221(4) 0.0607(16) Uani 1 1 d . . . . .
H3 H 0.675658 0.104483 0.917917 0.073 Uiso 1 1 calc R U . . .
C5 C 0.8266(10) 0.2247(4) 0.8727(4) 0.0526(14) Uani 1 1 d . . . . .
H5 H 0.945290 0.193969 0.836209 0.063 Uiso 1 1 calc R U . . .
C7 C 0.8177(10) 0.3226(4) 0.8758(4) 0.0452(12) Uani 1 1 d . . . . .
C8 C 1.0512(11) 0.4773(5) 0.8455(4) 0.0548(15) Uani 1 1 d . . . . .
H8A H 1.231265 0.490820 0.837687 0.066 Uiso 1 1 calc R U . . .
H8B H 1.019679 0.499895 0.910373 0.066 Uiso 1 1 calc R U . . .
C9 C 0.9172(9) 0.5367(4) 0.7885(4) 0.0452(13) Uani 1 1 d . . . . .
C11 C 0.7019(9) 0.4956(4) 0.7343(4) 0.0479(13) Uani 1 1 d . . . . .
H11 H 0.633242 0.431292 0.733154 0.057 Uiso 1 1 calc R U . . .
C12 C 0.5912(10) 0.5526(4) 0.6817(4) 0.0488(13) Uani 1 1 d . . . . .
H12 H 0.449194 0.525686 0.644363 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6883(9) 0.6472(4) 0.6845(3) 0.0433(12) Uani 1 1 d . . . . .
C17 C 0.6498(9) 0.7059(4) 0.5443(3) 0.0385(11) Uani 1 1 d . . . . .
C20 C 0.5347(8) 0.7682(4) 0.4971(3) 0.0382(11) Uani 1 1 d . . . . .
C21 C 0.3559(10) 0.8274(4) 0.5373(4) 0.0477(13) Uani 1 1 d . . . . .
H21 H 0.305847 0.825503 0.597412 0.057 Uiso 1 1 calc R U . . .
C25 C 0.2572(11) 0.8867(4) 0.4893(4) 0.0539(14) Uani 1 1 d . . . . .
H25 H 0.139685 0.925820 0.516432 0.065 Uiso 1 1 calc R U . . .
C24 C 0.3309(10) 0.8898(4) 0.3980(4) 0.0512(14) Uani 1 1 d . . . . .
C4 C 0.4751(11) 0.3105(6) 0.9819(4) 0.0652(18) Uani 1 1 d . . . . .
H4 H 0.356143 0.340717 1.018662 0.078 Uiso 1 1 calc R U . . .
C6 C 0.6385(11) 0.3666(5) 0.9323(4) 0.0576(15) Uani 1 1 d . . . . .
H6 H 0.627449 0.432774 0.936916 0.069 Uiso 1 1 calc R U . . .
C10 C 1.0150(10) 0.6329(4) 0.7918(4) 0.0480(13) Uani 1 1 d . . . . .
H10 H 1.158021 0.659602 0.828670 0.058 Uiso 1 1 calc R U . . .
C13 C 0.9021(9) 0.6903(4) 0.7405(3) 0.0439(12) Uani 1 1 d . . . . .
C15 C 1.1966(11) 0.8330(4) 0.7970(4) 0.0560(15) Uani 1 1 d . . . . .
H15A H 1.348169 0.808351 0.771982 0.067 Uiso 1 1 calc R U . . .
H15B H 1.179033 0.820749 0.859492 0.067 Uiso 1 1 calc R U . . .
C16 C 1.2123(14) 0.9401(5) 0.7978(5) 0.078(2) Uani 1 1 d . . . . .
H16A H 1.355594 0.974049 0.835381 0.118 Uiso 1 1 calc R U . . .
H16B H 1.229916 0.951348 0.735713 0.118 Uiso 1 1 calc R U . . .
H16C H 1.061531 0.963691 0.822834 0.118 Uiso 1 1 calc R U . . .
C18 C 0.8243(9) 0.6531(4) 0.5018(4) 0.0479(13) Uani 1 1 d . . . . .
H18 H 0.905625 0.612972 0.532272 0.057 Uiso 1 1 calc R U . . .
C19 C 0.8801(10) 0.6606(5) 0.4087(4) 0.0546(15) Uani 1 1 d . . . . .
H19 H 0.999483 0.623402 0.380011 0.065 Uiso 1 1 calc R U . . .
N2 N 0.7787(8) 0.7152(4) 0.3600(3) 0.0517(12) Uani 1 1 d . . . . .
C22 C 0.6060(9) 0.7708(4) 0.4040(3) 0.0416(12) Uani 1 1 d . . . . .
C23 C 0.4999(10) 0.8332(4) 0.3551(4) 0.0501(13) Uani 1 1 d . . . . .
H23 H 0.544323 0.835717 0.294549 0.060 Uiso 1 1 calc R U . . .
H100 H 1.053(14) 0.330(6) 0.788(6) 0.10(3) Uiso 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
Cl1 C24 1.743(6) . ?
O1 C17 1.380(6) . ?
O1 C14 1.399(6) . ?
O2 C13 1.356(7) . ?
O2 C15 1.438(7) . ?
N1 C7 1.392(7) . ?
N1 C8 1.428(8) . ?
N1 H100 0.86(8) . ?
C1 C2 1.517(10) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.361(10) . ?
C2 C3 1.393(9) . ?
C3 C5 1.385(8) . ?
C3 H3 0.9300 . ?
C5 C7 1.377(8) . ?
C5 H5 0.9300 . ?
C7 C6 1.400(8) . ?
C8 C9 1.526(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.381(8) . ?
C9 C11 1.392(8) . ?
C11 C12 1.394(8) . ?
C11 H11 0.9300 . ?
C12 C14 1.360(8) . ?
C12 H12 0.9300 . ?
C14 C13 1.405(7) . ?
C17 C18 1.350(7) . ?
C17 C20 1.412(7) . ?
C20 C21 1.408(7) . ?
C20 C22 1.430(7) . ?
C21 C25 1.343(8) . ?
C21 H21 0.9300 . ?
C25 C24 1.411(8) . ?
C25 H25 0.9300 . ?
C24 C23 1.360(8) . ?
C4 C6 1.406(9) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C10 C13 1.392(7) . ?
C10 H10 0.9300 . ?
C15 C16 1.498(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.425(8) . ?
C18 H18 0.9300 . ?
C19 N2 1.307(7) . ?
C19 H19 0.9300 . ?
N2 C22 1.373(7) . ?
C22 C23 1.404(7) . ?
C23 H23 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
C17 O1 C14 117.9(4) . . ?
C13 O2 C15 118.3(4) . . ?
C7 N1 C8 123.9(5) . . ?
C7 N1 H100 105(5) . . ?
C8 N1 H100 129(5) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 C3 117.4(6) . . ?
C4 C2 C1 121.8(6) . . ?
C3 C2 C1 120.8(6) . . ?
C5 C3 C2 120.9(6) . . ?
C5 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C7 C5 C3 122.1(5) . . ?
C7 C5 H5 118.9 . . ?
C3 C5 H5 118.9 . . ?
C5 C7 N1 120.4(5) . . ?
C5 C7 C6 117.3(5) . . ?
N1 C7 C6 122.3(5) . . ?
N1 C8 C9 115.9(5) . . ?
N1 C8 H8A 108.3 . . ?
C9 C8 H8A 108.3 . . ?
N1 C8 H8B 108.3 . . ?
C9 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C11 120.5(5) . . ?
C10 C9 C8 118.2(5) . . ?
C11 C9 C8 121.3(5) . . ?
C9 C11 C12 118.8(5) . . ?
C9 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C14 C12 C11 120.8(5) . . ?
C14 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C14 O1 120.4(5) . . ?
C12 C14 C13 121.0(5) . . ?
O1 C14 C13 118.6(5) . . ?
C18 C17 O1 124.6(5) . . ?
C18 C17 C20 119.8(4) . . ?
O1 C17 C20 115.7(4) . . ?
C21 C20 C17 123.2(4) . . ?
C21 C20 C22 119.1(5) . . ?
C17 C20 C22 117.7(4) . . ?
C25 C21 C20 120.3(5) . . ?
C25 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C25 C24 120.3(5) . . ?
C21 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C23 C24 C25 122.0(5) . . ?
C23 C24 Cl1 119.4(4) . . ?
C25 C24 Cl1 118.6(4) . . ?
C2 C4 C6 122.5(6) . . ?
C2 C4 H4 118.8 . . ?
C6 C4 H4 118.8 . . ?
C7 C6 C4 119.8(6) . . ?
C7 C6 H6 120.1 . . ?
C4 C6 H6 120.1 . . ?
C9 C10 C13 120.8(5) . . ?
C9 C10 H10 119.6 . . ?
C13 C10 H10 119.6 . . ?
O2 C13 C10 125.4(5) . . ?
O2 C13 C14 116.4(5) . . ?
C10 C13 C14 118.2(5) . . ?
O2 C15 C16 107.3(5) . . ?
O2 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O2 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C18 C19 117.9(5) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
N2 C19 C18 125.9(5) . . ?
N2 C19 H19 117.1 . . ?
C18 C19 H19 117.1 . . ?
C19 N2 C22 116.2(4) . . ?
N2 C22 C23 117.8(5) . . ?
N2 C22 C20 122.5(5) . . ?
C23 C22 C20 119.7(5) . . ?
C24 C23 C22 118.7(5) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?

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
C4 C2 C3 C5 0.1(9) . . . . ?
C1 C2 C3 C5 179.0(6) . . . . ?
C2 C3 C5 C7 -0.4(9) . . . . ?
C3 C5 C7 N1 -178.8(5) . . . . ?
C3 C5 C7 C6 0.7(8) . . . . ?
C8 N1 C7 C5 -156.5(6) . . . . ?
C8 N1 C7 C6 24.0(8) . . . . ?
C7 N1 C8 C9 -101.6(6) . . . . ?
N1 C8 C9 C10 -165.9(5) . . . . ?
N1 C8 C9 C11 14.1(7) . . . . ?
C10 C9 C11 C12 1.6(7) . . . . ?
C8 C9 C11 C12 -178.3(5) . . . . ?
C9 C11 C12 C14 -1.2(7) . . . . ?
C11 C12 C14 O1 -178.4(4) . . . . ?
C11 C12 C14 C13 -0.2(8) . . . . ?
C17 O1 C14 C12 -90.4(6) . . . . ?
C17 O1 C14 C13 91.4(5) . . . . ?
C14 O1 C17 C18 2.4(7) . . . . ?
C14 O1 C17 C20 -177.3(4) . . . . ?
C18 C17 C20 C21 -178.4(5) . . . . ?
O1 C17 C20 C21 1.3(7) . . . . ?
C18 C17 C20 C22 1.4(7) . . . . ?
O1 C17 C20 C22 -179.0(4) . . . . ?
C17 C20 C21 C25 178.6(5) . . . . ?
C22 C20 C21 C25 -1.1(8) . . . . ?
C20 C21 C25 C24 0.3(9) . . . . ?
C21 C25 C24 C23 0.8(9) . . . . ?
C21 C25 C24 Cl1 -179.4(5) . . . . ?
C3 C2 C4 C6 -0.2(9) . . . . ?
C1 C2 C4 C6 -179.1(6) . . . . ?
C5 C7 C6 C4 -0.7(8) . . . . ?
N1 C7 C6 C4 178.7(6) . . . . ?
C2 C4 C6 C7 0.5(9) . . . . ?
C11 C9 C10 C13 -0.6(8) . . . . ?
C8 C9 C10 C13 179.4(5) . . . . ?
C15 O2 C13 C10 -0.1(8) . . . . ?
C15 O2 C13 C14 179.4(5) . . . . ?
C9 C10 C13 O2 178.7(5) . . . . ?
C9 C10 C13 C14 -0.8(7) . . . . ?
C12 C14 C13 O2 -178.3(4) . . . . ?
O1 C14 C13 O2 -0.1(7) . . . . ?
C12 C14 C13 C10 1.2(7) . . . . ?
O1 C14 C13 C10 179.4(4) . . . . ?
C13 O2 C15 C16 -169.6(5) . . . . ?
O1 C17 C18 C19 178.6(5) . . . . ?
C20 C17 C18 C19 -1.8(7) . . . . ?
C17 C18 C19 N2 0.6(9) . . . . ?
C18 C19 N2 C22 1.0(9) . . . . ?
C19 N2 C22 C23 177.7(5) . . . . ?
C19 N2 C22 C20 -1.4(7) . . . . ?
C21 C20 C22 N2 -179.9(5) . . . . ?
C17 C20 C22 N2 0.3(7) . . . . ?
C21 C20 C22 C23 1.0(7) . . . . ?
C17 C20 C22 C23 -178.8(5) . . . . ?
C25 C24 C23 C22 -0.9(8) . . . . ?
Cl1 C24 C23 C22 179.3(4) . . . . ?
N2 C22 C23 C24 -179.1(5) . . . . ?
C20 C22 C23 C24 0.0(7) . . . . ?

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
C16 H16B Cl1 0.96 2.97 3.491(8) 115.1 2_676

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.108

