# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_olga1805
_audit_block_doi                 10.5517/ccdc.csd.cc1zsln0
_database_code_depnum_ccdc_archive 'CCDC 1840893'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;

_chemical_name_systematic        
7,8,9,11,12-pentamethoxy-1,2,5,13b-tetrahydrodibenzo[c,e]pyrrolo[1,2-a]azepin-3-one
_chemical_name_common            ?
_chemical_melting_point_gt       465
_chemical_melting_point_lt       466
_chemical_formula_moiety         'C22 H25 N O6'
_chemical_formula_sum            'C22 H25 N O6'
_chemical_formula_weight         399.43

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_preparation       'petroleum ether : ethyl acetate, 1:1'

_cell_length_a                   10.9821(5)
_cell_length_b                   9.7710(3)
_cell_length_c                   21.1370(9)
_cell_angle_alpha                90
_cell_angle_beta                 119.629(3)
_cell_angle_gamma                90
_cell_volume                     1971.56(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_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'

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'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1264

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 0.92186(19) 0.3630(2) 0.88886(9) 0.0588(5) Uani 1 1 d . . . . .
H1A H 0.8649 0.4447 0.8782 0.071 Uiso 1 1 calc R U . . .
H1B H 0.8927 0.2970 0.9130 0.071 Uiso 1 1 calc R U . . .
C2 C 1.07577(19) 0.3964(2) 0.93496(10) 0.0682(5) Uani 1 1 d . . . . .
H2A H 1.0949 0.4891 0.9259 0.082 Uiso 1 1 calc R U . . .
H2B H 1.1062 0.3866 0.9863 0.082 Uiso 1 1 calc R U . . .
C3 C 1.14808(18) 0.2936(2) 0.91150(10) 0.0626(5) Uani 1 1 d . . . . .
N4 N 1.04886(13) 0.23842(15) 0.84816(7) 0.0535(4) Uani 1 1 d . . . . .
C5 C 1.07859(17) 0.1420(2) 0.80480(9) 0.0582(5) Uani 1 1 d . . . . .
H5A H 1.0381 0.0537 0.8047 0.070 Uiso 1 1 calc R U . . .
H5B H 1.1791 0.1303 0.8268 0.070 Uiso 1 1 calc R U . . .
C5A C 1.02008(16) 0.19093(18) 0.72735(9) 0.0499(4) Uani 1 1 d . . . . .
C6 C 1.11003(17) 0.22458(19) 0.70111(10) 0.0548(4) Uani 1 1 d . . . . .
H6 H 1.2064 0.2184 0.7318 0.066 Uiso 1 1 calc R U . . .
C7 C 1.05829(17) 0.26684(17) 0.63039(10) 0.0501(4) Uani 1 1 d . . . . .
C8 C 0.91432(16) 0.28311(16) 0.58573(8) 0.0450(4) Uani 1 1 d . . . . .
C9 C 0.82377(15) 0.24899(16) 0.61140(8) 0.0447(4) Uani 1 1 d . . . . .
C9A C 0.87470(16) 0.19970(16) 0.68226(9) 0.0462(4) Uani 1 1 d . . . . .
C9B C 0.77783(15) 0.15612(17) 0.70860(9) 0.0460(4) Uani 1 1 d . . . . .
C10 C 0.66722(16) 0.06787(17) 0.66606(9) 0.0505(4) Uani 1 1 d . . . . .
H10 H 0.6583 0.0338 0.6229 0.061 Uiso 1 1 calc R U . . .
C11 C 0.57092(16) 0.03007(17) 0.68657(9) 0.0514(4) Uani 1 1 d . . . . .
C12 C 0.58593(15) 0.07936(17) 0.75224(9) 0.0502(4) Uani 1 1 d . . . . .
C13 C 0.69640(16) 0.16430(17) 0.79541(9) 0.0489(4) Uani 1 1 d . . . . .
H13 H 0.7064 0.1956 0.8393 0.059 Uiso 1 1 calc R U . . .
C13A C 0.79340(15) 0.20421(16) 0.77468(8) 0.0449(4) Uani 1 1 d . . . . .
C13B C 0.91085(15) 0.30283(17) 0.81973(9) 0.0479(4) Uani 1 1 d . . . . .
H13B H 0.9053 0.3789 0.7882 0.057 Uiso 1 1 calc R U . . .
O3 O 1.27232(14) 0.26448(16) 0.94269(8) 0.0855(5) Uani 1 1 d . . . . .
O7 O 1.13755(12) 0.29626(13) 0.59872(7) 0.0645(4) Uani 1 1 d . . . . .
C71 C 1.28218(18) 0.2623(2) 0.63774(12) 0.0656(5) Uani 1 1 d . . . . .
H71A H 1.3257 0.2887 0.6098 0.098 Uiso 1 1 calc R U . . .
H71B H 1.2924 0.1654 0.6463 0.098 Uiso 1 1 calc R U . . .
H71C H 1.3262 0.3098 0.6835 0.098 Uiso 1 1 calc R U . . .
O8 O 0.86273(12) 0.32680(12) 0.51518(6) 0.0545(3) Uani 1 1 d . . . . .
C81 C 0.8479(3) 0.4700(2) 0.50752(12) 0.0824(6) Uani 1 1 d . . . . .
H81A H 0.8106 0.4942 0.4573 0.124 Uiso 1 1 calc R U . . .
H81B H 0.9377 0.5126 0.5361 0.124 Uiso 1 1 calc R U . . .
H81C H 0.7852 0.5009 0.5240 0.124 Uiso 1 1 calc R U . . .
O9 O 0.68294(11) 0.25690(12) 0.56262(6) 0.0550(3) Uani 1 1 d . . . . .
C91 C 0.60557(19) 0.3573(2) 0.57602(12) 0.0733(6) Uani 1 1 d . . . . .
H91A H 0.5092 0.3537 0.5384 0.110 Uiso 1 1 calc R U . . .
H91B H 0.6430 0.4463 0.5765 0.110 Uiso 1 1 calc R U . . .
H91C H 0.6120 0.3401 0.6223 0.110 Uiso 1 1 calc R U . . .
O11 O 0.45745(12) -0.05125(14) 0.64675(7) 0.0656(4) Uani 1 1 d . . . . .
C111 C 0.4253(2) -0.0820(2) 0.57392(11) 0.0741(6) Uani 1 1 d . . . . .
H11A H 0.3435 -0.1391 0.5512 0.111 Uiso 1 1 calc R U . . .
H11B H 0.5029 -0.1291 0.5749 0.111 Uiso 1 1 calc R U . . .
H11C H 0.4078 0.0015 0.5468 0.111 Uiso 1 1 calc R U . . .
O12 O 0.48557(12) 0.03751(13) 0.76844(7) 0.0632(4) Uani 1 1 d . . . . .
C121 C 0.4866(2) 0.0978(2) 0.82925(11) 0.0733(6) Uani 1 1 d . . . . .
H12A H 0.4111 0.0609 0.8346 0.110 Uiso 1 1 calc R U . . .
H12B H 0.4751 0.1950 0.8223 0.110 Uiso 1 1 calc R U . . .
H12C H 0.5741 0.0784 0.8722 0.110 Uiso 1 1 calc R U . . .


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 C2 1.511(2) . ?
C1 C13B 1.523(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.508(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O3 1.220(2) . ?
C3 N4 1.352(2) . ?
N4 C5 1.459(2) . ?
N4 C13B 1.468(2) . ?
C5 C5A 1.510(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5A C6 1.390(2) . ?
C5A C9A 1.400(2) . ?
C6 C7 1.374(2) . ?
C6 H6 0.9300 . ?
C7 O7 1.3655(19) . ?
C7 C8 1.393(2) . ?
C8 O8 1.3753(18) . ?
C8 C9 1.389(2) . ?
C9 O9 1.3727(18) . ?
C9 C9A 1.400(2) . ?
C9A C9B 1.486(2) . ?
C9B C10 1.396(2) . ?
C9B C13A 1.402(2) . ?
C10 C11 1.377(2) . ?
C10 H10 0.9300 . ?
C11 O11 1.3621(19) . ?
C11 C12 1.400(2) . ?
C12 O12 1.3684(18) . ?
C12 C13 1.378(2) . ?
C13 C13A 1.393(2) . ?
C13 H13 0.9300 . ?
C13A C13B 1.511(2) . ?
C13B H13B 0.9800 . ?
O7 C71 1.421(2) . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
O8 C81 1.409(2) . ?
C81 H81A 0.9600 . ?
C81 H81B 0.9600 . ?
C81 H81C 0.9600 . ?
O9 C91 1.415(2) . ?
C91 H91A 0.9600 . ?
C91 H91B 0.9600 . ?
C91 H91C 0.9600 . ?
O11 C111 1.431(2) . ?
C111 H11A 0.9600 . ?
C111 H11B 0.9600 . ?
C111 H11C 0.9600 . ?
O12 C121 1.409(2) . ?
C121 H12A 0.9600 . ?
C121 H12B 0.9600 . ?
C121 H12C 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
C2 C1 C13B 103.59(14) . . ?
C2 C1 H1A 111.0 . . ?
C13B C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
C13B C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C3 C2 C1 104.29(15) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
O3 C3 N4 125.5(2) . . ?
O3 C3 C2 127.41(18) . . ?
N4 C3 C2 107.07(15) . . ?
C3 N4 C5 123.93(14) . . ?
C3 N4 C13B 113.46(15) . . ?
C5 N4 C13B 121.75(13) . . ?
N4 C5 C5A 111.65(14) . . ?
N4 C5 H5A 109.3 . . ?
C5A C5 H5A 109.3 . . ?
N4 C5 H5B 109.3 . . ?
C5A C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5A C9A 120.66(15) . . ?
C6 C5A C5 120.11(14) . . ?
C9A C5A C5 119.22(14) . . ?
C7 C6 C5A 120.78(15) . . ?
C7 C6 H6 119.6 . . ?
C5A C6 H6 119.6 . . ?
O7 C7 C6 125.14(15) . . ?
O7 C7 C8 115.39(15) . . ?
C6 C7 C8 119.47(14) . . ?
O8 C8 C9 120.50(14) . . ?
O8 C8 C7 119.43(14) . . ?
C9 C8 C7 119.99(14) . . ?
O9 C9 C8 116.85(14) . . ?
O9 C9 C9A 121.92(13) . . ?
C8 C9 C9A 121.08(14) . . ?
C5A C9A C9 117.86(14) . . ?
C5A C9A C9B 120.93(14) . . ?
C9 C9A C9B 121.20(13) . . ?
C10 C9B C13A 119.19(14) . . ?
C10 C9B C9A 119.46(14) . . ?
C13A C9B C9A 121.33(14) . . ?
C11 C10 C9B 121.48(16) . . ?
C11 C10 H10 119.3 . . ?
C9B C10 H10 119.3 . . ?
O11 C11 C10 124.91(16) . . ?
O11 C11 C12 115.89(14) . . ?
C10 C11 C12 119.18(15) . . ?
O12 C12 C13 124.65(16) . . ?
O12 C12 C11 115.51(15) . . ?
C13 C12 C11 119.83(15) . . ?
C12 C13 C13A 121.34(15) . . ?
C12 C13 H13 119.3 . . ?
C13A C13 H13 119.3 . . ?
C13 C13A C9B 118.95(15) . . ?
C13 C13A C13B 121.83(14) . . ?
C9B C13A C13B 119.16(13) . . ?
N4 C13B C13A 111.80(14) . . ?
N4 C13B C1 101.33(13) . . ?
C13A C13B C1 119.25(13) . . ?
N4 C13B H13B 108.0 . . ?
C13A C13B H13B 108.0 . . ?
C1 C13B H13B 108.0 . . ?
C7 O7 C71 117.83(13) . . ?
O7 C71 H71A 109.5 . . ?
O7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
O7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C8 O8 C81 113.27(13) . . ?
O8 C81 H81A 109.5 . . ?
O8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
O8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C9 O9 C91 116.98(13) . . ?
O9 C91 H91A 109.5 . . ?
O9 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
O9 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C11 O11 C111 116.82(14) . . ?
O11 C111 H11A 109.5 . . ?
O11 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
O11 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
C12 O12 C121 117.36(14) . . ?
O12 C121 H12A 109.5 . . ?
O12 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
O12 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 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
C13B C1 C2 C3 -28.82(19) . . . . ?
C1 C2 C3 O3 -165.09(18) . . . . ?
C1 C2 C3 N4 15.2(2) . . . . ?
O3 C3 N4 C5 -4.7(3) . . . . ?
C2 C3 N4 C5 175.00(15) . . . . ?
O3 C3 N4 C13B -174.19(16) . . . . ?
C2 C3 N4 C13B 5.52(19) . . . . ?
C3 N4 C5 C5A -125.15(17) . . . . ?
C13B N4 C5 C5A 43.5(2) . . . . ?
N4 C5 C5A C6 114.73(18) . . . . ?
N4 C5 C5A C9A -66.3(2) . . . . ?
C9A C5A C6 C7 -0.1(3) . . . . ?
C5 C5A C6 C7 178.80(17) . . . . ?
C5A C6 C7 O7 -176.96(16) . . . . ?
C5A C6 C7 C8 3.5(3) . . . . ?
O7 C7 C8 O8 -0.3(2) . . . . ?
C6 C7 C8 O8 179.32(16) . . . . ?
O7 C7 C8 C9 176.59(14) . . . . ?
C6 C7 C8 C9 -3.8(3) . . . . ?
O8 C8 C9 O9 2.1(2) . . . . ?
C7 C8 C9 O9 -174.79(14) . . . . ?
O8 C8 C9 C9A 177.68(14) . . . . ?
C7 C8 C9 C9A 0.8(2) . . . . ?
C6 C5A C9A C9 -2.8(2) . . . . ?
C5 C5A C9A C9 178.26(15) . . . . ?
C6 C5A C9A C9B 176.36(16) . . . . ?
C5 C5A C9A C9B -2.6(2) . . . . ?
O9 C9 C9A C5A 177.82(14) . . . . ?
C8 C9 C9A C5A 2.4(2) . . . . ?
O9 C9 C9A C9B -1.3(2) . . . . ?
C8 C9 C9A C9B -176.71(15) . . . . ?
C5A C9A C9B C10 -130.44(17) . . . . ?
C9 C9A C9B C10 48.7(2) . . . . ?
C5A C9A C9B C13A 51.0(2) . . . . ?
C9 C9A C9B C13A -129.91(17) . . . . ?
C13A C9B C10 C11 1.8(2) . . . . ?
C9A C9B C10 C11 -176.80(15) . . . . ?
C9B C10 C11 O11 177.40(16) . . . . ?
C9B C10 C11 C12 -1.2(3) . . . . ?
O11 C11 C12 O12 1.0(2) . . . . ?
C10 C11 C12 O12 179.71(14) . . . . ?
O11 C11 C12 C13 -178.88(15) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
O12 C12 C13 C13A -178.99(15) . . . . ?
C11 C12 C13 C13A 0.9(2) . . . . ?
C12 C13 C13A C9B -0.2(2) . . . . ?
C12 C13 C13A C13B 176.94(15) . . . . ?
C10 C9B C13A C13 -1.1(2) . . . . ?
C9A C9B C13A C13 177.51(14) . . . . ?
C10 C9B C13A C13B -178.34(14) . . . . ?
C9A C9B C13A C13B 0.3(2) . . . . ?
C3 N4 C13B C13A -151.59(14) . . . . ?
C5 N4 C13B C13A 38.7(2) . . . . ?
C3 N4 C13B C1 -23.49(18) . . . . ?
C5 N4 C13B C1 166.77(15) . . . . ?
C13 C13A C13B N4 116.41(16) . . . . ?
C9B C13A C13B N4 -66.42(19) . . . . ?
C13 C13A C13B C1 -1.4(2) . . . . ?
C9B C13A C13B C1 175.76(15) . . . . ?
C2 C1 C13B N4 31.01(17) . . . . ?
C2 C1 C13B C13A 154.13(15) . . . . ?
C6 C7 O7 C71 9.6(3) . . . . ?
C8 C7 O7 C71 -170.80(15) . . . . ?
C9 C8 O8 C81 91.31(19) . . . . ?
C7 C8 O8 C81 -91.81(19) . . . . ?
C8 C9 O9 C91 -114.02(17) . . . . ?
C9A C9 O9 C91 70.4(2) . . . . ?
C10 C11 O11 C111 -9.8(3) . . . . ?
C12 C11 O11 C111 168.79(16) . . . . ?
C13 C12 O12 C121 7.5(2) . . . . ?
C11 C12 O12 C121 -172.36(15) . . . . ?

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
C1 H1B O8 0.97 2.63 3.564(2) 160.9 4_566
C81 H81A O7 0.96 2.57 3.262(2) 129.5 3_766
C91 H91A O3 0.96 2.64 3.543(2) 156.2 4_465
C111 H11A O9 0.96 2.55 3.045(2) 112.1 3_656
C121 H12B O11 0.96 2.58 3.477(3) 156.0 2_656
########################################################################### 

_audit_creation_method           SHELXL-2013

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'

_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.
;

_cell_measurement_reflns_used    15903
_cell_measurement_theta_min      4.632
_cell_measurement_theta_max      66.030

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.810
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.081
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.8719
_exptl_absorpt_correction_T_max  0.9222
_exptl_special_details           ?

_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_details      
'51 runs, 1320 frames, detector distance = 42 mm'
_diffrn_reflns_number            15903
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_av_R_equivalents  0.0471 # before absorption correction
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.632
_diffrn_reflns_theta_max         66.030
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             3402
_reflns_number_gt                2552
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'X--AREA      (STOE & CIE, 2015)'
_computing_cell_refinement       'X--AREA      (STOE & CIE, 2015)'
_computing_data_reduction        'X--AREA      (STOE & CIE, 2015)'
_computing_structure_solution    'SHELXS97     (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL--2013 (Sheldrick,  2013)'
_computing_molecular_graphics    'Ortep--3     (Farrugia,   1997)'
_computing_publication_material  'WinGX        (Farrugia,   1999)'

_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)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3402
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_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.
;


_refine_diff_density_max         0.290
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_OLGA1703
_audit_block_doi                 10.5517/ccdc.csd.cc1q4l4l
_database_code_depnum_ccdc_archive 'CCDC 1583329'
_audit_update_record             
;
2018-05-03 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;

_chemical_name_systematic        
;
1-(3,4,5-trimethoxybenzyl)-5-(3,4,5-trimethoxyphenyl)pyrrolidin-2-one
;
_chemical_name_common            ?
_chemical_melting_point_gt       408
_chemical_melting_point_lt       409
_chemical_formula_moiety         'C23 H29 N O7'
_chemical_formula_sum            'C23 H29 N O7'
_chemical_formula_weight         431.47
_chemical_absolute_configuration unk

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_preparation       CH₃OH

_cell_length_a                   7.0556(3)
_cell_length_b                   15.3824(5)
_cell_length_c                   10.7866(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.471(3)
_cell_angle_gamma                90
_cell_volume                     1110.38(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

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

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1117

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
N1 N 0.9452(3) 0.22338(13) 0.13396(18) 0.0402(4) Uani 1 1 d . . . . .
C2 C 1.1463(3) 0.22031(15) 0.1745(2) 0.0431(5) Uani 1 1 d . . . . .
C3 C 1.2176(4) 0.2494(2) 0.0641(3) 0.0560(6) Uani 1 1 d . . . . .
H3A H 1.2768 0.2013 0.0313 0.067 Uiso 1 1 calc R U . . .
H3B H 1.3162 0.2953 0.0925 0.067 Uiso 1 1 calc R U . . .
C4 C 1.0341(4) 0.2823(2) -0.0397(3) 0.0593(7) Uani 1 1 d . . . . .
H4A H 1.0307 0.2610 -0.1251 0.071 Uiso 1 1 calc R U . . .
H4B H 1.0332 0.3453 -0.0416 0.071 Uiso 1 1 calc R U . . .
C5 C 0.8538(3) 0.24770(15) -0.0036(2) 0.0406(5) Uani 1 1 d . . . . .
H5 H 0.8006 0.1957 -0.0554 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8284(3) 0.18446(16) 0.2093(2) 0.0427(5) Uani 1 1 d . . . . .
H10A H 0.6989 0.2127 0.1858 0.051 Uiso 1 1 calc R U . . .
H10B H 0.8955 0.1952 0.3014 0.051 Uiso 1 1 calc R U . . .
C11 C 0.7974(3) 0.08733(15) 0.1881(2) 0.0378(4) Uani 1 1 d . . . . .
C12 C 0.6644(3) 0.04560(16) 0.2395(2) 0.0402(5) Uani 1 1 d . . . . .
H12 H 0.5875 0.0777 0.2789 0.048 Uiso 1 1 calc R U . . .
C13 C 0.6470(3) -0.04439(16) 0.2316(2) 0.0393(5) Uani 1 1 d . . . . .
C14 C 0.7610(3) -0.09299(15) 0.1714(2) 0.0402(4) Uani 1 1 d . . . . .
C15 C 0.8926(3) -0.04988(15) 0.1186(2) 0.0391(5) Uani 1 1 d . . . . .
C16 C 0.9099(3) 0.03985(15) 0.1272(2) 0.0392(5) Uani 1 1 d . . . . .
H16 H 0.9973 0.0684 0.0920 0.047 Uiso 1 1 calc R U . . .
O2 O 1.2512(3) 0.19592(16) 0.28319(19) 0.0640(5) Uani 1 1 d . . . . .
C51 C 0.6903(3) 0.31437(14) -0.0240(2) 0.0383(5) Uani 1 1 d . . . . .
C52 C 0.7153(3) 0.38354(16) 0.0621(2) 0.0438(5) Uani 1 1 d . . . . .
H52 H 0.8281 0.3861 0.1357 0.053 Uiso 1 1 calc R U . . .
C53 C 0.5723(4) 0.44919(17) 0.0388(3) 0.0473(5) Uani 1 1 d . . . . .
C54 C 0.4037(3) 0.44458(17) -0.0711(3) 0.0467(5) Uani 1 1 d . . . . .
C55 C 0.3792(3) 0.37507(17) -0.1582(2) 0.0426(5) Uani 1 1 d . . . . .
C56 C 0.5216(3) 0.30922(16) -0.1339(2) 0.0405(5) Uani 1 1 d . . . . .
H56 H 0.5041 0.2622 -0.1906 0.049 Uiso 1 1 calc R U . . .
O13 O 0.5221(3) -0.09188(13) 0.27847(17) 0.0507(4) Uani 1 1 d . . . . .
C17 C 0.4168(4) -0.0479(2) 0.3530(3) 0.0544(6) Uani 1 1 d . . . . .
H17A H 0.5107 -0.0227 0.4293 0.082 Uiso 1 1 calc R U . . .
H17B H 0.3333 -0.0886 0.3791 0.082 Uiso 1 1 calc R U . . .
H17C H 0.3353 -0.0029 0.3008 0.082 Uiso 1 1 calc R U . . .
O14 O 0.7498(3) -0.18195(11) 0.17087(18) 0.0500(4) Uani 1 1 d . . . . .
C18 C 0.6433(5) -0.2192(2) 0.0489(3) 0.0665(8) Uani 1 1 d . . . . .
H18A H 0.5064 -0.2007 0.0237 0.100 Uiso 1 1 calc R U . . .
H18B H 0.6493 -0.2815 0.0560 0.100 Uiso 1 1 calc R U . . .
H18C H 0.7019 -0.2009 -0.0159 0.100 Uiso 1 1 calc R U . . .
O15 O 0.9988(3) -0.10145(12) 0.06183(19) 0.0504(4) Uani 1 1 d . . . . .
C19 C 1.1264(4) -0.0599(2) 0.0015(2) 0.0489(5) Uani 1 1 d . . . . .
H19A H 1.0522 -0.0170 -0.0590 0.073 Uiso 1 1 calc R U . . .
H19B H 1.1786 -0.1024 -0.0443 0.073 Uiso 1 1 calc R U . . .
H19C H 1.2348 -0.0324 0.0671 0.073 Uiso 1 1 calc R U . . .
O53 O 0.5856(3) 0.51955(14) 0.1172(2) 0.0661(6) Uani 1 1 d . . . . .
C57 C 0.7615(5) 0.5287(3) 0.2254(4) 0.0852(12) Uani 1 1 d . . . . .
H57A H 0.7720 0.4809 0.2844 0.128 Uiso 1 1 calc R U . . .
H57B H 0.7561 0.5823 0.2697 0.128 Uiso 1 1 calc R U . . .
H57C H 0.8758 0.5291 0.1953 0.128 Uiso 1 1 calc R U . . .
O54 O 0.2591(3) 0.50784(13) -0.0935(2) 0.0634(5) Uani 1 1 d . . . . .
C58 C 0.2852(6) 0.5757(2) -0.1734(5) 0.0881(12) Uani 1 1 d . . . . .
H58A H 0.4087 0.6051 -0.1310 0.132 Uiso 1 1 calc R U . . .
H58B H 0.1764 0.6161 -0.1887 0.132 Uiso 1 1 calc R U . . .
H58C H 0.2882 0.5524 -0.2553 0.132 Uiso 1 1 calc R U . . .
O55 O 0.2101(3) 0.37797(14) -0.26232(18) 0.0564(5) Uani 1 1 d . . . . .
C59 C 0.1908(5) 0.3171(3) -0.3643(3) 0.0798(11) Uani 1 1 d . . . . .
H59A H 0.3028 0.3224 -0.3961 0.120 Uiso 1 1 calc R U . . .
H59B H 0.0696 0.3284 -0.4342 0.120 Uiso 1 1 calc R U . . .
H59C H 0.1867 0.2593 -0.3316 0.120 Uiso 1 1 calc R U . . .


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
N1 C2 1.347(3) . ?
N1 C10 1.457(3) . ?
N1 C5 1.466(3) . ?
C2 O2 1.230(3) . ?
C2 C3 1.501(4) . ?
C3 C4 1.505(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.539(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C51 1.506(3) . ?
C5 H5 0.9800 . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.387(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.390(4) . ?
C12 H12 0.9300 . ?
C13 O13 1.360(3) . ?
C13 C14 1.400(3) . ?
C14 O14 1.371(3) . ?
C14 C15 1.400(3) . ?
C15 O15 1.362(3) . ?
C15 C16 1.386(3) . ?
C16 H16 0.9300 . ?
C51 C52 1.386(3) . ?
C51 C56 1.391(3) . ?
C52 C53 1.393(3) . ?
C52 H52 0.9300 . ?
C53 O53 1.358(3) . ?
C53 C54 1.390(3) . ?
C54 O54 1.375(3) . ?
C54 C55 1.397(4) . ?
C55 O55 1.355(3) . ?
C55 C56 1.392(3) . ?
C56 H56 0.9300 . ?
O13 C17 1.426(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O14 C18 1.414(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O15 C19 1.419(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O53 C57 1.416(4) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
O54 C58 1.403(5) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
O55 C59 1.417(4) . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 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
C2 N1 C10 121.89(18) . . ?
C2 N1 C5 114.72(18) . . ?
C10 N1 C5 121.60(18) . . ?
O2 C2 N1 125.0(2) . . ?
O2 C2 C3 126.6(2) . . ?
N1 C2 C3 108.4(2) . . ?
C2 C3 C4 105.4(2) . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C3 C4 C5 106.3(2) . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
N1 C5 C51 113.11(18) . . ?
N1 C5 C4 102.14(18) . . ?
C51 C5 C4 112.6(2) . . ?
N1 C5 H5 109.6 . . ?
C51 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
N1 C10 C11 113.62(18) . . ?
N1 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C16 C11 C12 120.4(2) . . ?
C16 C11 C10 120.88(19) . . ?
C12 C11 C10 118.57(19) . . ?
C11 C12 C13 119.56(19) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
O13 C13 C12 124.6(2) . . ?
O13 C13 C14 114.9(2) . . ?
C12 C13 C14 120.51(19) . . ?
O14 C14 C13 119.6(2) . . ?
O14 C14 C15 121.1(2) . . ?
C13 C14 C15 119.2(2) . . ?
O15 C15 C16 124.1(2) . . ?
O15 C15 C14 115.9(2) . . ?
C16 C15 C14 120.0(2) . . ?
C15 C16 C11 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C52 C51 C56 120.5(2) . . ?
C52 C51 C5 119.7(2) . . ?
C56 C51 C5 119.65(19) . . ?
C51 C52 C53 120.3(2) . . ?
C51 C52 H52 119.9 . . ?
C53 C52 H52 119.9 . . ?
O53 C53 C54 116.3(2) . . ?
O53 C53 C52 124.2(2) . . ?
C54 C53 C52 119.5(2) . . ?
O54 C54 C53 120.0(2) . . ?
O54 C54 C55 119.8(2) . . ?
C53 C54 C55 120.2(2) . . ?
O55 C55 C56 125.0(2) . . ?
O55 C55 C54 114.9(2) . . ?
C56 C55 C54 120.1(2) . . ?
C51 C56 C55 119.4(2) . . ?
C51 C56 H56 120.3 . . ?
C55 C56 H56 120.3 . . ?
C13 O13 C17 118.0(2) . . ?
O13 C17 H17A 109.5 . . ?
O13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 O14 C18 114.9(2) . . ?
O14 C18 H18A 109.5 . . ?
O14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 O15 C19 117.60(19) . . ?
O15 C19 H19A 109.5 . . ?
O15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C53 O53 C57 117.5(2) . . ?
O53 C57 H57A 109.5 . . ?
O53 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
O53 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C54 O54 C58 113.6(3) . . ?
O54 C58 H58A 109.5 . . ?
O54 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
O54 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C55 O55 C59 117.7(2) . . ?
O55 C59 H59A 109.5 . . ?
O55 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
O55 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 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
C10 N1 C2 O2 -10.0(4) . . . . ?
C5 N1 C2 O2 -175.0(2) . . . . ?
C10 N1 C2 C3 168.6(2) . . . . ?
C5 N1 C2 C3 3.7(3) . . . . ?
O2 C2 C3 C4 -173.4(3) . . . . ?
N1 C2 C3 C4 8.0(3) . . . . ?
C2 C3 C4 C5 -15.8(3) . . . . ?
C2 N1 C5 C51 -134.6(2) . . . . ?
C10 N1 C5 C51 60.4(3) . . . . ?
C2 N1 C5 C4 -13.3(3) . . . . ?
C10 N1 C5 C4 -178.3(2) . . . . ?
C3 C4 C5 N1 17.2(3) . . . . ?
C3 C4 C5 C51 138.9(2) . . . . ?
C2 N1 C10 C11 -81.8(3) . . . . ?
C5 N1 C10 C11 82.1(2) . . . . ?
N1 C10 C11 C16 14.1(3) . . . . ?
N1 C10 C11 C12 -170.64(19) . . . . ?
C16 C11 C12 C13 1.1(3) . . . . ?
C10 C11 C12 C13 -174.2(2) . . . . ?
C11 C12 C13 O13 180.0(2) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
O13 C13 C14 O14 -4.0(3) . . . . ?
C12 C13 C14 O14 176.5(2) . . . . ?
O13 C13 C14 C15 179.27(19) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
O14 C14 C15 O15 3.2(3) . . . . ?
C13 C14 C15 O15 179.88(18) . . . . ?
O14 C14 C15 C16 -176.2(2) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
O15 C15 C16 C11 -179.3(2) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
C10 C11 C16 C15 174.4(2) . . . . ?
N1 C5 C51 C52 41.5(3) . . . . ?
C4 C5 C51 C52 -73.7(3) . . . . ?
N1 C5 C51 C56 -142.8(2) . . . . ?
C4 C5 C51 C56 102.0(2) . . . . ?
C56 C51 C52 C53 -0.6(4) . . . . ?
C5 C51 C52 C53 175.1(2) . . . . ?
C51 C52 C53 O53 -179.4(2) . . . . ?
C51 C52 C53 C54 0.3(4) . . . . ?
O53 C53 C54 O54 -1.9(4) . . . . ?
C52 C53 C54 O54 178.4(2) . . . . ?
O53 C53 C54 C55 179.1(2) . . . . ?
C52 C53 C54 C55 -0.7(4) . . . . ?
O54 C54 C55 O55 1.5(3) . . . . ?
C53 C54 C55 O55 -179.4(2) . . . . ?
O54 C54 C55 C56 -177.8(2) . . . . ?
C53 C54 C55 C56 1.3(4) . . . . ?
C52 C51 C56 C55 1.2(3) . . . . ?
C5 C51 C56 C55 -174.5(2) . . . . ?
O55 C55 C56 C51 179.3(2) . . . . ?
C54 C55 C56 C51 -1.5(3) . . . . ?
C12 C13 O13 C17 -6.9(3) . . . . ?
C14 C13 O13 C17 173.56(19) . . . . ?
C13 C14 O14 C18 106.7(3) . . . . ?
C15 C14 O14 C18 -76.7(3) . . . . ?
C16 C15 O15 C19 -3.7(3) . . . . ?
C14 C15 O15 C19 176.97(19) . . . . ?
C54 C53 O53 C57 -176.1(3) . . . . ?
C52 C53 O53 C57 3.6(5) . . . . ?
C53 C54 O54 C58 93.1(3) . . . . ?
C55 C54 O54 C58 -87.8(3) . . . . ?
C56 C55 O55 C59 -10.2(4) . . . . ?
C54 C55 O55 C59 170.5(3) . . . . ?

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
C56 H56 O13 0.93 2.65 3.475(3) 148.3 2_554
C18 H18A O2 0.96 2.65 3.312(4) 126.6 2_454
C18 H18C O15 0.96 2.51 3.061(4) 116.2 .
C19 H19B O2 0.96 2.53 3.466(3) 165.0 2_554

_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(19)
################################################################### 

#
# The Model has Chirality at C5  (Polar  SPGR) R  
#
_audit_creation_method           SHELXL-2013

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'

_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.
;

_cell_measurement_reflns_used    8566
_cell_measurement_theta_min      5.192
_cell_measurement_theta_max      72.794

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.790
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.079
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166.
;
_exptl_absorpt_correction_T_min  0.8909
_exptl_absorpt_correction_T_max  0.9240
_exptl_special_details           ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_details      
;
 34 runs, 1132 frames, detector distance = 42 mm
;
_diffrn_reflns_number            8566
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  0.0517 # before absorbtion correction      
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.192
_diffrn_reflns_theta_max         72.794
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.571
_diffrn_reflns_point_group_measured_fraction_full 0.585
_reflns_number_total             2533
_reflns_number_gt                2453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.164
_reflns_Friedel_fraction_max     0.161
_reflns_Friedel_fraction_full    0.174

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'X--AREA      (STOE & CIE, 2015)'
_computing_cell_refinement       'X--AREA      (STOE & CIE, 2015)'
_computing_data_reduction        'X--AREA      (STOE & CIE, 2015)'
_computing_structure_solution    'SHELXS97     (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL--2013 (Sheldrick,  2013)'
_computing_molecular_graphics    'Ortep--3     (Farrugia,   1997)'
_computing_publication_material  'WinGX        (Farrugia,   1999)'

_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)+(0.0755P)²+0.0239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2533
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_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.
;

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_olga1807
_audit_block_doi                 10.5517/ccdc.csd.cc1zsm8n
_database_code_depnum_ccdc_archive 'CCDC 1840912'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;

_chemical_name_systematic        
7,8,10,11,12-Pentamethoxy-1,2,5,13b-tetrahydrodibenzo[c,e]pyrrolo[1,2-a]azepin-3-one
_chemical_name_common            ?
_chemical_melting_point_gt       ????
_chemical_melting_point_lt       ????
_chemical_formula_moiety         'C22 H25 N O6'
_chemical_formula_sum            'C22 H25 N O6'
_chemical_formula_weight         399.43

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_preparation       'ethyl acetate : petroleum ether, 1:1'

_cell_length_a                   15.7969(3)
_cell_length_b                   8.7827(2)
_cell_length_c                   14.6012(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.801(2)
_cell_angle_gamma                90
_cell_volume                     1967.28(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)

_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'

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'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1116

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 0.26216(10) 0.26505(17) 0.75174(10) 0.0454(3) Uani 1 1 d . . . . .
H1A H 0.3248 0.2550 0.7744 0.054 Uiso 1 1 calc R U . . .
H1B H 0.2398 0.3239 0.7970 0.054 Uiso 1 1 calc R U . . .
C2 C 0.21878(10) 0.10999(18) 0.73597(11) 0.0502(4) Uani 1 1 d . . . . .
H2A H 0.2544 0.0335 0.7750 0.060 Uiso 1 1 calc R U . . .
H2B H 0.1620 0.1124 0.7505 0.060 Uiso 1 1 calc R U . . .
C3 C 0.21013(8) 0.07680(16) 0.63296(10) 0.0405(3) Uani 1 1 d . . . . .
N4 N 0.22688(7) 0.20646(12) 0.59130(7) 0.0349(3) Uani 1 1 d . . . . .
C5 C 0.21160(8) 0.22632(14) 0.48966(9) 0.0354(3) Uani 1 1 d . . . . .
H5A H 0.1835 0.1360 0.4582 0.042 Uiso 1 1 calc R U . . .
H5B H 0.2670 0.2384 0.4728 0.042 Uiso 1 1 calc R U . . .
C5A C 0.15534(8) 0.36293(14) 0.45641(9) 0.0336(3) Uani 1 1 d . . . . .
C6 C 0.07044(8) 0.34361(15) 0.40170(9) 0.0354(3) Uani 1 1 d . . . . .
H6 H 0.0497 0.2458 0.3853 0.042 Uiso 1 1 calc R U . . .
C7 C 0.01693(8) 0.46659(15) 0.37168(9) 0.0355(3) Uani 1 1 d . . . . .
C8 C 0.04832(8) 0.61438(15) 0.39695(9) 0.0354(3) Uani 1 1 d . . . . .
C9 C 0.13215(8) 0.63392(14) 0.45048(9) 0.0355(3) Uani 1 1 d . . . . .
H9 H 0.1528 0.7318 0.4667 0.043 Uiso 1 1 calc R U . . .
C9A C 0.18697(8) 0.50910(14) 0.48103(9) 0.0335(3) Uani 1 1 d . . . . .
C9B C 0.27533(8) 0.53284(14) 0.54296(9) 0.0341(3) Uani 1 1 d . . . . .
C10 C 0.33417(8) 0.63713(14) 0.51855(9) 0.0362(3) Uani 1 1 d . . . . .
C11 C 0.41540(8) 0.66355(15) 0.57837(10) 0.0387(3) Uani 1 1 d . . . . .
C12 C 0.43989(8) 0.58479(15) 0.66345(10) 0.0411(3) Uani 1 1 d . . . . .
C13 C 0.38373(8) 0.47877(15) 0.68736(10) 0.0385(3) Uani 1 1 d . . . . .
H13 H 0.4008 0.4249 0.7436 0.046 Uiso 1 1 calc R U . . .
C13A C 0.30235(8) 0.45234(14) 0.62828(9) 0.0334(3) Uani 1 1 d . . . . .
C13B C 0.23867(8) 0.34040(14) 0.65387(9) 0.0335(3) Uani 1 1 d . . . . .
H13B H 0.1822 0.3913 0.6461 0.040 Uiso 1 1 calc R U . . .
O3 O 0.19015(8) -0.04437(12) 0.59214(8) 0.0582(3) Uani 1 1 d . . . . .
O7 O -0.06648(6) 0.45762(11) 0.31776(7) 0.0456(3) Uani 1 1 d . . . . .
C71 C -0.10697(10) 0.31203(18) 0.30876(12) 0.0511(4) Uani 1 1 d . . . . .
H71A H -0.0812 0.2483 0.2694 0.077 Uiso 1 1 calc R U . . .
H71B H -0.1682 0.3231 0.2809 0.077 Uiso 1 1 calc R U . . .
H71C H -0.0989 0.2663 0.3700 0.077 Uiso 1 1 calc R U . . .
O8 O -0.00909(6) 0.73030(11) 0.36616(7) 0.0456(3) Uani 1 1 d . . . . .
C81 C 0.01860(10) 0.87925(16) 0.39720(12) 0.0520(4) Uani 1 1 d . . . . .
H81A H 0.0348 0.8814 0.4649 0.078 Uiso 1 1 calc R U . . .
H81B H -0.0281 0.9499 0.3747 0.078 Uiso 1 1 calc R U . . .
H81C H 0.0678 0.9072 0.3730 0.078 Uiso 1 1 calc R U . . .
O10 O 0.31182(7) 0.70280(11) 0.43076(7) 0.0477(3) Uani 1 1 d . . . . .
C101 C 0.31156(12) 0.8637(2) 0.42590(15) 0.0663(5) Uani 1 1 d . . . . .
H10A H 0.2966 0.9050 0.4808 0.099 Uiso 1 1 calc R U . . .
H10B H 0.2695 0.8963 0.3705 0.099 Uiso 1 1 calc R U . . .
H10C H 0.3684 0.8990 0.4231 0.099 Uiso 1 1 calc R U . . .
O11 O 0.47133(6) 0.76945(11) 0.55522(8) 0.0489(3) Uani 1 1 d . . . . .
C111 C 0.53488(14) 0.7093(2) 0.51292(18) 0.0833(7) Uani 1 1 d . . . . .
H11A H 0.5665 0.6305 0.5522 0.125 Uiso 1 1 calc R U . . .
H11B H 0.5744 0.7886 0.5052 0.125 Uiso 1 1 calc R U . . .
H11C H 0.5073 0.6677 0.4524 0.125 Uiso 1 1 calc R U . . .
O12 O 0.52038(6) 0.61916(13) 0.71804(8) 0.0577(3) Uani 1 1 d . . . . .
C121 C 0.55162(12) 0.5287(3) 0.79910(15) 0.0871(7) Uani 1 1 d . . . . .
H12A H 0.5105 0.5311 0.8380 0.131 Uiso 1 1 calc R U . . .
H12B H 0.6066 0.5679 0.8339 0.131 Uiso 1 1 calc R U . . .
H12C H 0.5590 0.4257 0.7804 0.131 Uiso 1 1 calc R U . . .


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 C2 1.517(2) . ?
C1 C13B 1.5378(18) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.506(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O3 1.2238(17) . ?
C3 N4 1.3467(17) . ?
N4 C5 1.4562(16) . ?
N4 C13B 1.4738(16) . ?
C5 C5A 1.5031(17) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5A C9A 1.3933(18) . ?
C5A C6 1.3980(17) . ?
C6 C7 1.3772(18) . ?
C6 H6 0.9300 . ?
C7 O7 1.3664(15) . ?
C7 C8 1.4070(18) . ?
C8 O8 1.3662(15) . ?
C8 C9 1.3785(17) . ?
C9 C9A 1.4022(18) . ?
C9 H9 0.9300 . ?
C9A C9B 1.4857(17) . ?
C9B C13A 1.4072(18) . ?
C9B C10 1.4099(18) . ?
C10 O10 1.3727(16) . ?
C10 C11 1.3888(18) . ?
C11 O11 1.3792(16) . ?
C11 C12 1.394(2) . ?
C12 O12 1.3637(16) . ?
C12 C13 1.3870(19) . ?
C13 C13A 1.3862(17) . ?
C13 H13 0.9300 . ?
C13A C13B 1.5157(17) . ?
C13B H13B 0.9800 . ?
O7 C71 1.4218(17) . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
O8 C81 1.4190(17) . ?
C81 H81A 0.9600 . ?
C81 H81B 0.9600 . ?
C81 H81C 0.9600 . ?
O10 C101 1.415(2) . ?
C101 H10A 0.9600 . ?
C101 H10B 0.9600 . ?
C101 H10C 0.9600 . ?
O11 C111 1.402(2) . ?
C111 H11A 0.9600 . ?
C111 H11B 0.9600 . ?
C111 H11C 0.9600 . ?
O12 C121 1.413(2) . ?
C121 H12A 0.9600 . ?
C121 H12B 0.9600 . ?
C121 H12C 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
C2 C1 C13B 104.19(11) . . ?
C2 C1 H1A 110.9 . . ?
C13B C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
C13B C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
C3 C2 C1 104.80(11) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
O3 C3 N4 124.82(13) . . ?
O3 C3 C2 127.32(13) . . ?
N4 C3 C2 107.86(12) . . ?
C3 N4 C5 123.99(11) . . ?
C3 N4 C13B 113.85(11) . . ?
C5 N4 C13B 120.12(10) . . ?
N4 C5 C5A 111.48(10) . . ?
N4 C5 H5A 109.3 . . ?
C5A C5 H5A 109.3 . . ?
N4 C5 H5B 109.3 . . ?
C5A C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C9A C5A C6 119.70(11) . . ?
C9A C5A C5 120.27(11) . . ?
C6 C5A C5 120.03(11) . . ?
C7 C6 C5A 121.26(12) . . ?
C7 C6 H6 119.4 . . ?
C5A C6 H6 119.4 . . ?
O7 C7 C6 124.92(12) . . ?
O7 C7 C8 115.81(11) . . ?
C6 C7 C8 119.27(11) . . ?
O8 C8 C9 124.50(12) . . ?
O8 C8 C7 115.87(11) . . ?
C9 C8 C7 119.62(11) . . ?
C8 C9 C9A 121.33(12) . . ?
C8 C9 H9 119.3 . . ?
C9A C9 H9 119.3 . . ?
C5A C9A C9 118.81(11) . . ?
C5A C9A C9B 120.89(11) . . ?
C9 C9A C9B 120.21(11) . . ?
C13A C9B C10 118.10(11) . . ?
C13A C9B C9A 120.72(11) . . ?
C10 C9B C9A 121.17(11) . . ?
O10 C10 C11 120.68(11) . . ?
O10 C10 C9B 118.09(11) . . ?
C11 C10 C9B 121.03(12) . . ?
O11 C11 C10 120.55(12) . . ?
O11 C11 C12 119.69(12) . . ?
C10 C11 C12 119.74(12) . . ?
O12 C12 C13 124.38(13) . . ?
O12 C12 C11 115.66(12) . . ?
C13 C12 C11 119.96(12) . . ?
C13A C13 C12 120.64(12) . . ?
C13A C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C13A C9B 120.48(11) . . ?
C13 C13A C13B 121.78(11) . . ?
C9B C13A C13B 117.71(10) . . ?
N4 C13B C13A 110.98(10) . . ?
N4 C13B C1 101.49(10) . . ?
C13A C13B C1 118.75(11) . . ?
N4 C13B H13B 108.4 . . ?
C13A C13B H13B 108.4 . . ?
C1 C13B H13B 108.4 . . ?
C7 O7 C71 117.12(11) . . ?
O7 C71 H71A 109.5 . . ?
O7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
O7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C8 O8 C81 116.87(10) . . ?
O8 C81 H81A 109.5 . . ?
O8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
O8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C10 O10 C101 117.61(12) . . ?
O10 C101 H10A 109.5 . . ?
O10 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
O10 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
C11 O11 C111 114.95(12) . . ?
O11 C111 H11A 109.5 . . ?
O11 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
O11 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
C12 O12 C121 117.12(12) . . ?
O12 C121 H12A 109.5 . . ?
O12 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
O12 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 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
C13B C1 C2 C3 24.68(15) . . . . ?
C1 C2 C3 O3 168.80(15) . . . . ?
C1 C2 C3 N4 -12.32(15) . . . . ?
O3 C3 N4 C5 9.1(2) . . . . ?
C2 C3 N4 C5 -169.83(11) . . . . ?
O3 C3 N4 C13B 172.79(13) . . . . ?
C2 C3 N4 C13B -6.12(15) . . . . ?
C3 N4 C5 C5A 125.81(13) . . . . ?
C13B N4 C5 C5A -36.95(15) . . . . ?
N4 C5 C5A C9A 68.14(15) . . . . ?
N4 C5 C5A C6 -110.93(13) . . . . ?
C9A C5A C6 C7 -0.23(19) . . . . ?
C5 C5A C6 C7 178.84(12) . . . . ?
C5A C6 C7 O7 179.65(11) . . . . ?
C5A C6 C7 C8 -0.25(19) . . . . ?
O7 C7 C8 O8 1.35(17) . . . . ?
C6 C7 C8 O8 -178.73(11) . . . . ?
O7 C7 C8 C9 -179.33(11) . . . . ?
C6 C7 C8 C9 0.58(19) . . . . ?
O8 C8 C9 C9A 178.81(12) . . . . ?
C7 C8 C9 C9A -0.44(19) . . . . ?
C6 C5A C9A C9 0.38(18) . . . . ?
C5 C5A C9A C9 -178.69(11) . . . . ?
C6 C5A C9A C9B 177.00(11) . . . . ?
C5 C5A C9A C9B -2.07(18) . . . . ?
C8 C9 C9A C5A -0.04(19) . . . . ?
C8 C9 C9A C9B -176.69(11) . . . . ?
C5A C9A C9B C13A -49.17(17) . . . . ?
C9 C9A C9B C13A 127.41(13) . . . . ?
C5A C9A C9B C10 131.35(13) . . . . ?
C9 C9A C9B C10 -52.08(17) . . . . ?
C13A C9B C10 O10 172.78(11) . . . . ?
C9A C9B C10 O10 -7.72(18) . . . . ?
C13A C9B C10 C11 -2.10(18) . . . . ?
C9A C9B C10 C11 177.40(12) . . . . ?
O10 C10 C11 O11 7.38(19) . . . . ?
C9B C10 C11 O11 -177.87(11) . . . . ?
O10 C10 C11 C12 -174.01(12) . . . . ?
C9B C10 C11 C12 0.7(2) . . . . ?
O11 C11 C12 O12 -0.74(19) . . . . ?
C10 C11 C12 O12 -179.36(12) . . . . ?
O11 C11 C12 C13 179.64(12) . . . . ?
C10 C11 C12 C13 1.0(2) . . . . ?
O12 C12 C13 C13A 179.04(13) . . . . ?
C11 C12 C13 C13A -1.4(2) . . . . ?
C12 C13 C13A C9B 0.0(2) . . . . ?
C12 C13 C13A C13B -178.27(12) . . . . ?
C10 C9B C13A C13 1.74(18) . . . . ?
C9A C9B C13A C13 -177.76(11) . . . . ?
C10 C9B C13A C13B -179.96(11) . . . . ?
C9A C9B C13A C13B 0.54(17) . . . . ?
C3 N4 C13B C13A 148.54(11) . . . . ?
C5 N4 C13B C13A -47.05(14) . . . . ?
C3 N4 C13B C1 21.41(14) . . . . ?
C5 N4 C13B C1 -174.18(11) . . . . ?
C13 C13A C13B N4 -111.59(13) . . . . ?
C9B C13A C13B N4 70.12(14) . . . . ?
C13 C13A C13B C1 5.40(18) . . . . ?
C9B C13A C13B C1 -172.89(11) . . . . ?
C2 C1 C13B N4 -27.18(13) . . . . ?
C2 C1 C13B C13A -149.08(12) . . . . ?
C6 C7 O7 C71 13.89(19) . . . . ?
C8 C7 O7 C71 -166.20(12) . . . . ?
C9 C8 O8 C81 -4.28(19) . . . . ?
C7 C8 O8 C81 174.99(12) . . . . ?
C11 C10 O10 C101 -60.04(18) . . . . ?
C9B C10 O10 C101 125.06(14) . . . . ?
C10 C11 O11 C111 -97.14(18) . . . . ?
C12 C11 O11 C111 84.25(19) . . . . ?
C13 C12 O12 C121 7.0(2) . . . . ?
C11 C12 O12 C121 -172.55(17) . . . . ?
######################################################################### 

_audit_creation_method           SHELXL-2013

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'

_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.
;

_cell_measurement_reflns_used    20894
_cell_measurement_theta_min      5.768
_cell_measurement_theta_max      72.943

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.812
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.081
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.8420
_exptl_absorpt_correction_T_max  0.9220
_exptl_special_details           ?

_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_measurement_details      
'65 runs, 1715 frames, detector distance = 42 mm'
_diffrn_reflns_number            20894
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0391 # before absorption correction
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.768
_diffrn_reflns_theta_max         72.943
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3889
_reflns_number_gt                3289
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'X--AREA      (STOE & CIE, 2015)'
_computing_cell_refinement       'X--AREA      (STOE & CIE, 2015)'
_computing_data_reduction        'X--AREA      (STOE & CIE, 2015)'
_computing_structure_solution    'SHELXS97     (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL--2013 (Sheldrick,  2013)'
_computing_molecular_graphics    'Ortep--3     (Farrugia,   1997)'
_computing_publication_material  'WinGX        (Farrugia,   1999)'

_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)+(0.0604P)²+0.2843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3889
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


_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.
;


_refine_diff_density_max         0.207
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

