# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1541465'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_chemical_name_systematic        
6-acetyl-4,7-dimethyl-5-[3-(morpholin-4-yl)propoxycoumarin
_chemical_name_common            ?
_chemical_formula_moiety         C20H25O5N
_chemical_formula_sum            C20H25O5N
_chemical_formula_iupac          ?
_chemical_formula_weight         359.41

_chemical_melting_point          'MP: 128 -- 131 \%C'

_space_group_crystal_system      monoclinic
_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                   17.1277(16)
_cell_length_b                   9.9821(9)
_cell_length_c                   10.6929(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.349(2)
_cell_angle_gamma                90
_cell_volume                     1817.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9147
_cell_measurement_theta_min      2.9613
_cell_measurement_theta_max      25.4371
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.068
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            27947
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.43
_diffrn_reflns_theta_full        25.43
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12

_refine_special_details          'Refined as a 2-component twin.'

_reflns_number_total             3346
_reflns_number_gt                2502
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1238
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_number_reflns         3346
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.0790P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 V2013 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2013 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.47858(6) 0.29989(10) 0.35826(10) 0.0209(3) Uani d . . . 1.0 . .
C C2 0.49988(9) 0.18203(16) 0.30342(14) 0.0207(4) Uani d . . . 1.0 . .
O O2 0.55141(7) 0.19055(11) 0.23486(11) 0.0277(3) Uani d . . . 1.0 . .
C C3 0.45964(9) 0.06322(15) 0.33400(15) 0.0210(4) Uani d . . . 1.0 . .
H H3 0.4744 -0.0189 0.2985 0.025 Uiso calc U . R 1.0 . .
C C4 0.40172(9) 0.06035(15) 0.41049(14) 0.0173(3) Uani d . . . 1.0 . .
C C4A 0.37844(9) 0.18696(15) 0.46312(14) 0.0189(3) Uani d . . . 1.0 . .
C C5 0.31564(9) 0.20655(15) 0.53598(14) 0.0177(3) Uani d . . . 1.0 . .
C C6 0.29436(9) 0.33265(15) 0.57379(13) 0.0185(3) Uani d . . . 1.0 . .
C C7 0.33691(9) 0.44662(15) 0.54429(13) 0.0187(3) Uani d . . . 1.0 . .
C C8 0.39932(9) 0.42988(15) 0.47443(14) 0.0188(3) Uani d . . . 1.0 . .
H H8 0.4294 0.5052 0.4542 0.023 Uiso calc U . R 1.0 . .
C C8A 0.41810(9) 0.30357(14) 0.43389(14) 0.0171(3) Uani d . . . 1.0 . .
C C9A 0.31411(10) 0.58430(16) 0.58403(15) 0.0230(4) Uani d . P . 0.74(2) A 1
H H9A1 0.3241 0.5921 0.6758 0.035 Uiso calc U P R 0.74(2) A 1
H H9A2 0.2582 0.5991 0.5576 0.035 Uiso calc U P R 0.74(2) A 1
H H9A3 0.3452 0.6515 0.5446 0.035 Uiso calc U P R 0.74(2) A 1
C C9B 0.31411(10) 0.58430(16) 0.58403(15) 0.0230(4) Uani d . P . 0.26(2) A 2
H H9B1 0.3558 0.6207 0.6447 0.035 Uiso calc U P R 0.26(2) A 2
H H9B2 0.2651 0.579 0.6231 0.035 Uiso calc U P R 0.26(2) A 2
H H9B3 0.3066 0.6429 0.5102 0.035 Uiso calc U P R 0.26(2) A 2
C C10 0.36392(10) -0.07071(15) 0.43517(15) 0.0220(4) Uani d . . . 1.0 . .
H H10A 0.3074 -0.0654 0.4083 0.033 Uiso calc U . R 1.0 . .
H H10B 0.3724 -0.0909 0.5253 0.033 Uiso calc U . R 1.0 . .
H H10C 0.3872 -0.1417 0.388 0.033 Uiso calc U . R 1.0 . .
C C11 0.22108(10) 0.34484(16) 0.63949(15) 0.0231(4) Uani d . . . 1.0 . .
O O3 0.22431(7) 0.37268(14) 0.74995(11) 0.0348(3) Uani d . . . 1.0 . .
C C12A 0.14525(10) 0.3248(2) 0.55953(17) 0.0334(4) Uani d . P . 0.17(3) B 1
H H12A 0.1334 0.2289 0.553 0.05 Uiso calc U P R 0.17(3) B 1
H H12B 0.1492 0.3614 0.4754 0.05 Uiso calc U P R 0.17(3) B 1
H H12C 0.1032 0.371 0.5975 0.05 Uiso calc U P R 0.17(3) B 1
C C12B 0.14525(10) 0.3248(2) 0.55953(17) 0.0334(4) Uani d . P . 0.83(3) B 2
H H12D 0.1496 0.2475 0.5042 0.05 Uiso calc U P R 0.83(3) B 2
H H12E 0.1328 0.4051 0.5084 0.05 Uiso calc U P R 0.83(3) B 2
H H12F 0.1034 0.3086 0.6133 0.05 Uiso calc U P R 0.83(3) B 2
O O4 0.27186(6) 0.09878(10) 0.56932(9) 0.0178(3) Uani d . . . 1.0 . .
C C13 0.29812(9) 0.04933(16) 0.69508(13) 0.0194(4) Uani d . . . 1.0 . .
H H13A 0.287 0.1165 0.7589 0.023 Uiso calc U . R 1.0 . .
H H13B 0.3554 0.0327 0.7035 0.023 Uiso calc U . R 1.0 . .
C C14 0.25473(10) -0.07913(16) 0.71490(15) 0.0235(4) Uani d . . . 1.0 . .
H H14A 0.2785 -0.1221 0.7935 0.028 Uiso calc U . R 1.0 . .
H H14B 0.2612 -0.141 0.6444 0.028 Uiso calc U . R 1.0 . .
C C15 0.16800(9) -0.05799(16) 0.72325(15) 0.0234(4) Uani d . . . 1.0 . .
H H15A 0.1614 -0.0039 0.799 0.028 Uiso calc U . R 1.0 . .
H H15B 0.1453 -0.0067 0.6487 0.028 Uiso calc U . R 1.0 . .
N N1 0.12501(7) -0.18341(13) 0.72967(12) 0.0215(3) Uani d . . . 1.0 . .
C C16 0.04053(9) -0.16066(18) 0.71008(16) 0.0274(4) Uani d . . . 1.0 . .
H H16A 0.0265 -0.1191 0.6266 0.033 Uiso calc U . R 1.0 . .
H H16B 0.0253 -0.0979 0.7749 0.033 Uiso calc U . R 1.0 . .
C C17 -0.00387(10) -0.29042(19) 0.71737(16) 0.0306(4) Uani d . . . 1.0 . .
H H17A -0.061 -0.2725 0.7039 0.037 Uiso calc U . R 1.0 . .
H H17B 0.0095 -0.3516 0.6501 0.037 Uiso calc U . R 1.0 . .
O O5 0.01501(7) -0.35234(12) 0.83595(12) 0.0307(3) Uani d . . . 1.0 . .
C C18 0.14355(10) -0.25072(18) 0.85030(16) 0.0284(4) Uani d . . . 1.0 . .
H H18A 0.1318 -0.1901 0.919 0.034 Uiso calc U . R 1.0 . .
H H18B 0.2003 -0.2721 0.8627 0.034 Uiso calc U . R 1.0 . .
C C19 0.09673(11) -0.3778(2) 0.8558(2) 0.0378(5) Uani d . . . 1.0 . .
H H19A 0.1113 -0.4409 0.7909 0.045 Uiso calc U . R 1.0 . .
H H19B 0.1096 -0.4205 0.9391 0.045 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.3814(19) ?
O1 C8A . 1.3834(18) ?
C2 O2 . 1.2112(19) ?
C2 C3 . 1.428(2) ?
C3 C4 . 1.354(2) ?
C3 H3 . 0.95 ?
C4 C4A . 1.457(2) ?
C4 C10 . 1.496(2) ?
C4A C8A . 1.400(2) ?
C4A C5 . 1.410(2) ?
C5 O4 . 1.3806(18) ?
C5 C6 . 1.383(2) ?
C6 C7 . 1.406(2) ?
C6 C11 . 1.510(2) ?
C7 C8 . 1.380(2) ?
C7 C9A . 1.503(2) ?
C8 C8A . 1.383(2) ?
C8 H8 . 0.95 ?
C9A H9A1 . 0.98 ?
C9A H9A2 . 0.98 ?
C9A H9A3 . 0.98 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 O3 . 1.2087(19) ?
C11 C12A . 1.487(2) ?
C12A H12A . 0.98 ?
C12A H12B . 0.98 ?
C12A H12C . 0.98 ?
O4 C13 . 1.4561(17) ?
C13 C14 . 1.509(2) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.513(2) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 N1 . 1.458(2) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
N1 C16 . 1.457(2) ?
N1 C18 . 1.458(2) ?
C16 C17 . 1.508(2) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 O5 . 1.416(2) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
O5 C19 . 1.415(2) ?
C18 C19 . 1.505(3) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C8A . . 121.38(11) ?
O2 C2 O1 . . 116.19(13) ?
O2 C2 C3 . . 126.84(15) ?
O1 C2 C3 . . 116.96(13) ?
C4 C3 C2 . . 124.09(14) ?
C4 C3 H3 . . 118.0 ?
C2 C3 H3 . . 118.0 ?
C3 C4 C4A . . 117.71(13) ?
C3 C4 C10 . . 119.03(13) ?
C4A C4 C10 . . 123.25(14) ?
C8A C4A C5 . . 115.25(13) ?
C8A C4A C4 . . 118.34(14) ?
C5 C4A C4 . . 126.29(13) ?
O4 C5 C6 . . 117.74(14) ?
O4 C5 C4A . . 120.27(13) ?
C6 C5 C4A . . 121.98(13) ?
C5 C6 C7 . . 120.73(14) ?
C5 C6 C11 . . 117.96(13) ?
C7 C6 C11 . . 121.18(14) ?
C8 C7 C6 . . 118.38(14) ?
C8 C7 C9A . . 120.32(14) ?
C6 C7 C9A . . 121.28(14) ?
C7 C8 C8A . . 120.06(14) ?
C7 C8 H8 . . 120.0 ?
C8A C8 H8 . . 120.0 ?
C8 C8A O1 . . 115.00(13) ?
C8 C8A C4A . . 123.55(15) ?
O1 C8A C4A . . 121.43(13) ?
C7 C9A H9A1 . . 109.5 ?
C7 C9A H9A2 . . 109.5 ?
H9A1 C9A H9A2 . . 109.5 ?
C7 C9A H9A3 . . 109.5 ?
H9A1 C9A H9A3 . . 109.5 ?
H9A2 C9A H9A3 . . 109.5 ?
C4 C10 H10A . . 109.5 ?
C4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O3 C11 C12A . . 122.37(15) ?
O3 C11 C6 . . 121.51(15) ?
C12A C11 C6 . . 116.09(14) ?
C11 C12A H12A . . 109.5 ?
C11 C12A H12B . . 109.5 ?
H12A C12A H12B . . 109.5 ?
C11 C12A H12C . . 109.5 ?
H12A C12A H12C . . 109.5 ?
H12B C12A H12C . . 109.5 ?
C5 O4 C13 . . 112.42(11) ?
O4 C13 C14 . . 108.13(12) ?
O4 C13 H13A . . 110.1 ?
C14 C13 H13A . . 110.1 ?
O4 C13 H13B . . 110.1 ?
C14 C13 H13B . . 110.1 ?
H13A C13 H13B . . 108.4 ?
C13 C14 C15 . . 113.08(13) ?
C13 C14 H14A . . 109.0 ?
C15 C14 H14A . . 109.0 ?
C13 C14 H14B . . 109.0 ?
C15 C14 H14B . . 109.0 ?
H14A C14 H14B . . 107.8 ?
N1 C15 C14 . . 112.79(13) ?
N1 C15 H15A . . 109.0 ?
C14 C15 H15A . . 109.0 ?
N1 C15 H15B . . 109.0 ?
C14 C15 H15B . . 109.0 ?
H15A C15 H15B . . 107.8 ?
C16 N1 C15 . . 110.98(13) ?
C16 N1 C18 . . 108.35(12) ?
C15 N1 C18 . . 112.06(13) ?
N1 C16 C17 . . 110.92(14) ?
N1 C16 H16A . . 109.5 ?
C17 C16 H16A . . 109.5 ?
N1 C16 H16B . . 109.5 ?
C17 C16 H16B . . 109.5 ?
H16A C16 H16B . . 108.0 ?
O5 C17 C16 . . 110.78(14) ?
O5 C17 H17A . . 109.5 ?
C16 C17 H17A . . 109.5 ?
O5 C17 H17B . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 108.1 ?
C19 O5 C17 . . 109.70(13) ?
N1 C18 C19 . . 110.99(15) ?
N1 C18 H18A . . 109.4 ?
C19 C18 H18A . . 109.4 ?
N1 C18 H18B . . 109.4 ?
C19 C18 H18B . . 109.4 ?
H18A C18 H18B . . 108.0 ?
O5 C19 C18 . . 111.42(15) ?
O5 C19 H19A . . 109.3 ?
C18 C19 H19A . . 109.3 ?
O5 C19 H19B . . 109.3 ?
C18 C19 H19B . . 109.3 ?
H19A C19 H19B . . 108.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A O1 C2 O2 . . . . 177.13(13) ?
C8A O1 C2 C3 . . . . -3.4(2) ?
O2 C2 C3 C4 . . . . -179.25(16) ?
O1 C2 C3 C4 . . . . 1.3(2) ?
C2 C3 C4 C4A . . . . 1.0(2) ?
C2 C3 C4 C10 . . . . 179.90(14) ?
C3 C4 C4A C8A . . . . -1.3(2) ?
C10 C4 C4A C8A . . . . 179.84(14) ?
C3 C4 C4A C5 . . . . 174.57(14) ?
C10 C4 C4A C5 . . . . -4.3(2) ?
C8A C4A C5 O4 . . . . 179.34(12) ?
C4 C4A C5 O4 . . . . 3.4(2) ?
C8A C4A C5 C6 . . . . 1.0(2) ?
C4 C4A C5 C6 . . . . -174.96(14) ?
O4 C5 C6 C7 . . . . 179.29(12) ?
C4A C5 C6 C7 . . . . -2.3(2) ?
O4 C5 C6 C11 . . . . -4.8(2) ?
C4A C5 C6 C11 . . . . 173.56(13) ?
C5 C6 C7 C8 . . . . 1.4(2) ?
C11 C6 C7 C8 . . . . -174.35(13) ?
C5 C6 C7 C9A . . . . 179.59(13) ?
C11 C6 C7 C9A . . . . 3.9(2) ?
C6 C7 C8 C8A . . . . 0.8(2) ?
C9A C7 C8 C8A . . . . -177.44(14) ?
C7 C8 C8A O1 . . . . 176.21(12) ?
C7 C8 C8A C4A . . . . -2.2(2) ?
C2 O1 C8A C8 . . . . -175.25(12) ?
C2 O1 C8A C4A . . . . 3.2(2) ?
C5 C4A C8A C8 . . . . 1.3(2) ?
C4 C4A C8A C8 . . . . 177.54(14) ?
C5 C4A C8A O1 . . . . -177.03(13) ?
C4 C4A C8A O1 . . . . -0.7(2) ?
C5 C6 C11 O3 . . . . 110.58(18) ?
C7 C6 C11 O3 . . . . -73.6(2) ?
C5 C6 C11 C12A . . . . -71.25(19) ?
C7 C6 C11 C12A . . . . 104.59(18) ?
C6 C5 O4 C13 . . . . -84.78(15) ?
C4A C5 O4 C13 . . . . 96.79(16) ?
C5 O4 C13 C14 . . . . -172.00(12) ?
O4 C13 C14 C15 . . . . -68.54(17) ?
C13 C14 C15 N1 . . . . 174.20(12) ?
C14 C15 N1 C16 . . . . -167.62(13) ?
C14 C15 N1 C18 . . . . 71.10(17) ?
C15 N1 C16 C17 . . . . -179.72(14) ?
C18 N1 C16 C17 . . . . -56.28(18) ?
N1 C16 C17 O5 . . . . 59.11(19) ?
C16 C17 O5 C19 . . . . -58.99(19) ?
C16 N1 C18 C19 . . . . 55.60(18) ?
C15 N1 C18 C19 . . . . 178.38(14) ?
C17 O5 C19 C18 . . . . 58.6(2) ?
N1 C18 C19 O5 . . . . -57.9(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 O1 2_645 0.95 2.65 3.5689(19) 162.7 ?
C12A H12A O4 . 0.98 2.69 3.123(2) 107.0 ?
C12B H12D O4 . 0.98 2.60 3.123(2) 113.6 ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH3Cl'
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1541420'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_chemical_name_systematic        
'4,7-dimethyl-5-{3-[4-(2-fluorophenyl)piperazin-1-yl]propoxy}coumarin '
_chemical_name_common            ?
_chemical_formula_moiety         'C24H27O3N2 F'
_chemical_formula_sum            'C24H27O3N2 F'
_chemical_formula_iupac          ?
_chemical_formula_weight         410.47

_chemical_melting_point          'MP: 113 --115 \%C'

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7995(6)
_cell_length_b                   9.8117(8)
_cell_length_c                   14.8527(12)
_cell_angle_alpha                78.6250(19)
_cell_angle_beta                 82.4050(18)
_cell_angle_gamma                69.9762(18)
_cell_volume                     1044.36(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      3.0186
_cell_measurement_theta_max      25.3769
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.694
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.134
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            22213
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             3690
_reflns_number_gt                3303
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0899
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         3690
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+0.3735P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0141(18)

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'

_computing_data_collection       'APEX2 V2013 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2013 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.27572(11) 0.62800(8) 0.96988(6) 0.0199(2) Uani d . . . 1 . .
C C2 1.18645(16) 0.77437(13) 0.97357(9) 0.0215(3) Uani d . . . 1 . .
O O2 1.25417(12) 0.83224(10) 1.01736(7) 0.0313(2) Uani d . . . 1 . .
C C3 1.02348(16) 0.84261(13) 0.92481(8) 0.0211(3) Uani d . . . 1 . .
H H3 0.9657 0.9457 0.9212 0.025 Uiso calc U . R 1 . .
C C4 0.94807(16) 0.76795(13) 0.88388(8) 0.0191(3) Uani d . . . 1 . .
C C4A 1.03700(15) 0.61034(12) 0.88840(7) 0.0168(2) Uani d . . . 1 . .
C C5 0.97276(15) 0.51214(13) 0.85485(7) 0.0179(2) Uani d . . . 1 . .
C C6 1.07298(16) 0.36452(13) 0.86137(8) 0.0188(3) Uani d . . . 1 . .
H H6 1.0268 0.3008 0.8387 0.023 Uiso calc U . R 1 . .
C C7 1.24188(15) 0.30734(13) 0.90091(8) 0.0186(3) Uani d . . . 1 . .
C C8 1.30569(15) 0.39931(13) 0.93611(8) 0.0183(3) Uani d . . . 1 . .
H H8 1.4191 0.3621 0.964 0.022 Uiso calc U . R 1 . .
C C8A 1.20256(15) 0.54649(12) 0.93037(8) 0.0169(2) Uani d . . . 1 . .
C C9 1.35239(17) 0.14776(13) 0.90388(9) 0.0244(3) Uani d . . . 1 . .
H H9A 1.4578 0.1236 0.9404 0.037 Uiso calc U . R 1 . .
H H9B 1.3953 0.1284 0.8411 0.037 Uiso calc U . R 1 . .
H H9C 1.2762 0.0871 0.9321 0.037 Uiso calc U . R 1 . .
C C10 0.77586(17) 0.85189(14) 0.83578(9) 0.0267(3) Uani d . . . 1 . .
H H10A 0.7449 0.957 0.8374 0.04 Uiso calc U . R 1 . .
H H10B 0.6757 0.8176 0.8669 0.04 Uiso calc U . R 1 . .
H H10C 0.7946 0.8358 0.7716 0.04 Uiso calc U . R 1 . .
O O3 0.80865(11) 0.57316(9) 0.81676(6) 0.0221(2) Uani d . . . 1 . .
C C11 0.73318(17) 0.48149(13) 0.78162(8) 0.0224(3) Uani d . . . 1 . .
H H11A 0.7075 0.4066 0.8318 0.027 Uiso calc U . R 1 . .
H H11B 0.8193 0.4307 0.7342 0.027 Uiso calc U . R 1 . .
C C12 0.55831(16) 0.58332(14) 0.74035(8) 0.0226(3) Uani d . . . 1 . .
H H12A 0.5852 0.6635 0.6952 0.027 Uiso calc U . R 1 . .
H H12B 0.4715 0.6282 0.7896 0.027 Uiso calc U . R 1 . .
C C13 0.46963(17) 0.50339(13) 0.69281(8) 0.0224(3) Uani d . . . 1 . .
H H13A 0.5565 0.4586 0.6435 0.027 Uiso calc U . R 1 . .
H H13B 0.4433 0.423 0.738 0.027 Uiso calc U . R 1 . .
N N1 0.29964(13) 0.60120(11) 0.65276(7) 0.0204(2) Uani d . . . 1 . .
C C14 0.20241(16) 0.51561(13) 0.62367(8) 0.0216(3) Uani d . . . 1 . .
H H14A 0.1765 0.4457 0.6771 0.026 Uiso calc U . R 1 . .
H H14B 0.2805 0.4581 0.5769 0.026 Uiso calc U . R 1 . .
C C15 0.02428(16) 0.61517(14) 0.58360(8) 0.0216(3) Uani d . . . 1 . .
H H15A -0.0419 0.5554 0.5661 0.026 Uiso calc U . R 1 . .
H H15B -0.0545 0.6734 0.6299 0.026 Uiso calc U . R 1 . .
C C16 0.33567(16) 0.70450(14) 0.57351(8) 0.0227(3) Uani d . . . 1 . .
H H16A 0.4191 0.6493 0.5271 0.027 Uiso calc U . R 1 . .
H H16B 0.3969 0.766 0.5932 0.027 Uiso calc U . R 1 . .
C C17 0.16072(17) 0.80220(14) 0.53082(9) 0.0240(3) Uani d . . . 1 . .
H H17A 0.0803 0.8623 0.5758 0.029 Uiso calc U . R 1 . .
H H17B 0.189 0.8697 0.4765 0.029 Uiso calc U . R 1 . .
N N2 0.06575(13) 0.71322(11) 0.50266(7) 0.0198(2) Uani d . . . 1 . .
C C18 -0.03792(17) 0.86338(14) 0.35715(9) 0.0250(3) Uani d . . . 1 . .
C C19 -0.16827(19) 0.94708(15) 0.29737(9) 0.0300(3) Uani d . . . 1 . .
H H19 -0.1344 0.9929 0.2385 0.036 Uiso calc U . R 1 . .
C C20 -0.35077(18) 0.96394(14) 0.32430(9) 0.0291(3) Uani d . . . 1 . .
H H20 -0.4435 1.0217 0.284 0.035 Uiso calc U . R 1 . .
C C21 -0.39579(18) 0.89624(15) 0.40983(9) 0.0294(3) Uani d . . . 1 . .
H H21 -0.5202 0.9055 0.428 0.035 Uiso calc U . R 1 . .
C C22 -0.26154(17) 0.81440(14) 0.47003(9) 0.0246(3) Uani d . . . 1 . .
H H22 -0.2961 0.77 0.5292 0.03 Uiso calc U . R 1 . .
C C23 -0.07801(16) 0.79617(13) 0.44549(8) 0.0201(3) Uani d . . . 1 . .
F F1 0.14023(10) 0.84508(10) 0.32862(5) 0.0383(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.3735(14) ?
O1 C8A . 1.3768(14) ?
C2 O2 . 1.2109(15) ?
C2 C3 . 1.4344(17) ?
C3 C4 . 1.3482(17) ?
C3 H3 . 0.95 ?
C4 C4A . 1.4539(16) ?
C4 C10 . 1.5023(16) ?
C4A C8A . 1.3976(16) ?
C4A C5 . 1.4191(16) ?
C5 O3 . 1.3601(14) ?
C5 C6 . 1.3812(16) ?
C6 C7 . 1.4012(16) ?
C6 H6 . 0.95 ?
C7 C8 . 1.3776(17) ?
C7 C9 . 1.5017(16) ?
C8 C8A . 1.3833(16) ?
C8 H8 . 0.95 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
O3 C11 . 1.4342(14) ?
C11 C12 . 1.5101(16) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.5202(17) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 N1 . 1.4645(15) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
N1 C16 . 1.4591(15) ?
N1 C14 . 1.4604(15) ?
C14 C15 . 1.5161(17) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 N2 . 1.4593(15) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C17 . 1.5087(16) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 N2 . 1.4678(15) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
N2 C23 . 1.4124(15) ?
C18 F1 . 1.3587(15) ?
C18 C19 . 1.3694(18) ?
C18 C23 . 1.3949(18) ?
C19 C20 . 1.388(2) ?
C19 H19 . 0.95 ?
C20 C21 . 1.374(2) ?
C20 H20 . 0.95 ?
C21 C22 . 1.3890(18) ?
C21 H21 . 0.95 ?
C22 C23 . 1.3879(17) ?
C22 H22 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C8A . . 121.87(9) ?
O2 C2 O1 . . 116.50(11) ?
O2 C2 C3 . . 126.91(11) ?
O1 C2 C3 . . 116.59(10) ?
C4 C3 C2 . . 123.38(11) ?
C4 C3 H3 . . 118.3 ?
C2 C3 H3 . . 118.3 ?
C3 C4 C4A . . 118.53(10) ?
C3 C4 C10 . . 118.29(10) ?
C4A C4 C10 . . 123.17(10) ?
C8A C4A C5 . . 115.56(10) ?
C8A C4A C4 . . 117.69(10) ?
C5 C4A C4 . . 126.75(10) ?
O3 C5 C6 . . 123.22(10) ?
O3 C5 C4A . . 115.68(10) ?
C6 C5 C4A . . 121.10(10) ?
C5 C6 C7 . . 120.93(11) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C8 C7 C6 . . 119.29(10) ?
C8 C7 C9 . . 120.58(10) ?
C6 C7 C9 . . 120.13(10) ?
C7 C8 C8A . . 119.15(10) ?
C7 C8 H8 . . 120.4 ?
C8A C8 H8 . . 120.4 ?
O1 C8A C8 . . 114.59(10) ?
O1 C8A C4A . . 121.51(10) ?
C8 C8A C4A . . 123.90(11) ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C4 C10 H10A . . 109.5 ?
C4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C5 O3 C11 . . 119.31(9) ?
O3 C11 C12 . . 105.82(9) ?
O3 C11 H11A . . 110.6 ?
C12 C11 H11A . . 110.6 ?
O3 C11 H11B . . 110.6 ?
C12 C11 H11B . . 110.6 ?
H11A C11 H11B . . 108.7 ?
C11 C12 C13 . . 112.03(10) ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12B . . 109.2 ?
C13 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
N1 C13 C12 . . 112.43(10) ?
N1 C13 H13A . . 109.1 ?
C12 C13 H13A . . 109.1 ?
N1 C13 H13B . . 109.1 ?
C12 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
C16 N1 C14 . . 108.87(9) ?
C16 N1 C13 . . 111.26(9) ?
C14 N1 C13 . . 110.26(9) ?
N1 C14 C15 . . 110.92(10) ?
N1 C14 H14A . . 109.5 ?
C15 C14 H14A . . 109.5 ?
N1 C14 H14B . . 109.5 ?
C15 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.0 ?
N2 C15 C14 . . 108.64(9) ?
N2 C15 H15A . . 110.0 ?
C14 C15 H15A . . 110.0 ?
N2 C15 H15B . . 110.0 ?
C14 C15 H15B . . 110.0 ?
H15A C15 H15B . . 108.3 ?
N1 C16 C17 . . 111.10(10) ?
N1 C16 H16A . . 109.4 ?
C17 C16 H16A . . 109.4 ?
N1 C16 H16B . . 109.4 ?
C17 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
N2 C17 C16 . . 110.39(10) ?
N2 C17 H17A . . 109.6 ?
C16 C17 H17A . . 109.6 ?
N2 C17 H17B . . 109.6 ?
C16 C17 H17B . . 109.6 ?
H17A C17 H17B . . 108.1 ?
C23 N2 C15 . . 117.43(9) ?
C23 N2 C17 . . 113.54(9) ?
C15 N2 C17 . . 108.79(9) ?
F1 C18 C19 . . 118.02(11) ?
F1 C18 C23 . . 118.33(11) ?
C19 C18 C23 . . 123.65(12) ?
C18 C19 C20 . . 118.91(12) ?
C18 C19 H19 . . 120.5 ?
C20 C19 H19 . . 120.5 ?
C21 C20 C19 . . 119.29(12) ?
C21 C20 H20 . . 120.4 ?
C19 C20 H20 . . 120.4 ?
C20 C21 C22 . . 120.76(12) ?
C20 C21 H21 . . 119.6 ?
C22 C21 H21 . . 119.6 ?
C23 C22 C21 . . 121.38(12) ?
C23 C22 H22 . . 119.3 ?
C21 C22 H22 . . 119.3 ?
C22 C23 C18 . . 115.96(11) ?
C22 C23 N2 . . 124.44(11) ?
C18 C23 N2 . . 119.58(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A O1 C2 O2 . . . . 173.22(10) ?
C8A O1 C2 C3 . . . . -7.06(16) ?
O2 C2 C3 C4 . . . . -174.28(12) ?
O1 C2 C3 C4 . . . . 6.04(18) ?
C2 C3 C4 C4A . . . . -0.63(18) ?
C2 C3 C4 C10 . . . . 179.33(11) ?
C3 C4 C4A C8A . . . . -3.82(16) ?
C10 C4 C4A C8A . . . . 176.22(11) ?
C3 C4 C4A C5 . . . . 175.76(11) ?
C10 C4 C4A C5 . . . . -4.20(18) ?
C8A C4A C5 O3 . . . . 177.87(9) ?
C4 C4A C5 O3 . . . . -1.71(17) ?
C8A C4A C5 C6 . . . . -2.07(16) ?
C4 C4A C5 C6 . . . . 178.35(11) ?
O3 C5 C6 C7 . . . . 179.70(10) ?
C4A C5 C6 C7 . . . . -0.36(17) ?
C5 C6 C7 C8 . . . . 1.92(17) ?
C5 C6 C7 C9 . . . . -177.50(11) ?
C6 C7 C8 C8A . . . . -0.92(17) ?
C9 C7 C8 C8A . . . . 178.50(10) ?
C2 O1 C8A C8 . . . . -177.14(10) ?
C2 O1 C8A C4A . . . . 2.81(16) ?
C7 C8 C8A O1 . . . . 178.22(9) ?
C7 C8 C8A C4A . . . . -1.72(18) ?
C5 C4A C8A O1 . . . . -176.78(9) ?
C4 C4A C8A O1 . . . . 2.85(16) ?
C5 C4A C8A C8 . . . . 3.16(16) ?
C4 C4A C8A C8 . . . . -177.21(10) ?
C6 C5 O3 C11 . . . . 0.30(16) ?
C4A C5 O3 C11 . . . . -179.63(9) ?
C5 O3 C11 C12 . . . . -177.10(9) ?
O3 C11 C12 C13 . . . . 175.25(9) ?
C11 C12 C13 N1 . . . . 179.85(10) ?
C12 C13 N1 C16 . . . . 69.85(13) ?
C12 C13 N1 C14 . . . . -169.25(10) ?
C16 N1 C14 C15 . . . . -58.70(12) ?
C13 N1 C14 C15 . . . . 178.98(9) ?
N1 C14 C15 N2 . . . . 61.48(12) ?
C14 N1 C16 C17 . . . . 56.67(13) ?
C13 N1 C16 C17 . . . . 178.39(10) ?
N1 C16 C17 N2 . . . . -58.03(13) ?
C14 C15 N2 C23 . . . . 168.67(10) ?
C14 C15 N2 C17 . . . . -60.64(12) ?
C16 C17 N2 C23 . . . . -167.64(10) ?
C16 C17 N2 C15 . . . . 59.59(13) ?
F1 C18 C19 C20 . . . . 178.32(12) ?
C23 C18 C19 C20 . . . . -1.7(2) ?
C18 C19 C20 C21 . . . . -0.12(19) ?
C19 C20 C21 C22 . . . . 1.5(2) ?
C20 C21 C22 C23 . . . . -1.09(19) ?
C21 C22 C23 C18 . . . . -0.64(18) ?
C21 C22 C23 N2 . . . . -179.24(11) ?
F1 C18 C23 C22 . . . . -177.97(11) ?
C19 C18 C23 C22 . . . . 2.07(18) ?
F1 C18 C23 N2 . . . . 0.70(17) ?
C19 C18 C23 N2 . . . . -179.26(11) ?
C15 N2 C23 C22 . . . . 13.92(16) ?
C17 N2 C23 C22 . . . . -114.54(13) ?
C15 N2 C23 C18 . . . . -164.63(11) ?
C17 N2 C23 C18 . . . . 66.91(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 O2 2_777 0.95 2.52 3.3857(15) 152.2 ?
C8 H8 O2 2_867 0.95 2.62 3.4771(14) 150.4 ?
C17 H17B F1 . 0.99 2.35 2.9671(15) 119.7 ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
