#------------------------------------------------------------------------------
#$Date: 2021-09-06 14:47:38 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268823 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/30/7243033.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243033
loop_
_publ_author_name
'Jamshaid, Sana'
'Mohandoss, Sonaimuthu'
'Lee, Yong Rok'
_publ_section_title
;
 Indium(iii)-catalyzed solvent-free multicomponent [2 + 2 + 1 +
 1]-annulation to polycyclic functionalized fused pyridines as potential
 optical chemosensors
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              5113
_journal_page_last               5119
_journal_paper_doi               10.1039/D1GC01332G
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_chemical_melting_point          441
_chemical_name_systematic
3-Methoxy-10,10-dimethyl-6,9,10,11-tetrahydrobenzo[c]acridin-8(5H)-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                104.005(8)
_cell_angle_beta                 92.306(8)
_cell_angle_gamma                109.243(7)
_cell_formula_units_Z            4
_cell_length_a                   10.249(3)
_cell_length_b                   11.657(4)
_cell_length_c                   14.822(4)
_cell_measurement_reflns_used    6474
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.31
_cell_volume                     1608.2(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'PHOTON III M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33055
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.417
_diffrn_reflns_theta_min         1.922
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/EtOAc'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7942
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0891P)²+0.7672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1895
_refine_ls_wR_factor_ref         0.2295
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4218
_reflns_number_total             7942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc01332g2.cif
_cod_data_source_block           Lee-A
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7243033--7243035.cif.
;
_cod_original_cell_volume        1608.2(8)
_cod_database_code               7243033
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.6605(3) 0.6734(3) -0.0173(2) 0.0392(7) Uani 1 1 d . . . . .
C2 C 0.5188(3) 0.6304(3) -0.0463(2) 0.0427(7) Uani 1 1 d . . . . .
H2 H 0.4748 0.5487 -0.0864 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4413(3) 0.7064(3) -0.0170(2) 0.0378(7) Uani 1 1 d . . . . .
C4 C 0.5060(3) 0.8278(2) 0.04344(19) 0.0327(6) Uani 1 1 d . . . . .
C5 C 0.6485(3) 0.8681(3) 0.0725(2) 0.0359(6) Uani 1 1 d . . . . .
H5 H 0.6930 0.9489 0.1137 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7261(3) 0.7926(3) 0.0424(2) 0.0389(7) Uani 1 1 d . . . . .
H6 H 0.8224 0.8220 0.0623 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2863(3) 0.6605(3) -0.0471(3) 0.0514(9) Uani 1 1 d . . . . .
H7A H 0.2363 0.6258 0.0008 0.062 Uiso 1 1 calc R U . . .
H7B H 0.2616 0.5932 -0.1059 0.062 Uiso 1 1 calc R U . . .
C8 C 0.2434(3) 0.7690(3) -0.0607(2) 0.0440(7) Uani 1 1 d . . . . .
H8A H 0.2854 0.7972 -0.1133 0.053 Uiso 1 1 calc R U . . .
H8B H 0.1419 0.7399 -0.0757 0.053 Uiso 1 1 calc R U . . .
C9 C 0.2897(3) 0.8770(2) 0.0265(2) 0.0352(6) Uani 1 1 d . . . . .
C10 C 0.4232(3) 0.9089(2) 0.07395(19) 0.0314(6) Uani 1 1 d . . . . .
N1 N 0.4797(2) 1.0107(2) 0.14780(16) 0.0331(5) Uani 1 1 d . . . . .
C11 C 0.4041(3) 1.0839(2) 0.17738(19) 0.0323(6) Uani 1 1 d . . . . .
C12 C 0.2682(3) 1.0559(2) 0.1371(2) 0.0336(6) Uani 1 1 d . . . . .
C13 C 0.2130(3) 0.9514(3) 0.0597(2) 0.0384(7) Uani 1 1 d . . . . .
H13 H 0.1226 0.9316 0.0299 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1878(3) 1.1378(3) 0.1733(2) 0.0381(7) Uani 1 1 d . . . . .
C15 C 0.2635(3) 1.2583(3) 0.2463(2) 0.0416(7) Uani 1 1 d . . . . .
H15A H 0.1955 1.2852 0.2822 0.050 Uiso 1 1 calc R U . . .
H15B H 0.3089 1.3234 0.2151 0.050 Uiso 1 1 calc R U . . .
C16 C 0.3736(3) 1.2492(2) 0.3144(2) 0.0360(6) Uani 1 1 d . . . . .
C17 C 0.4738(3) 1.2001(3) 0.2572(2) 0.0388(7) Uani 1 1 d . . . . .
H17A H 0.5319 1.2671 0.2317 0.047 Uiso 1 1 calc R U . . .
H17B H 0.5355 1.1814 0.2991 0.047 Uiso 1 1 calc R U . . .
O1 O 0.7266(2) 0.59020(18) -0.05281(16) 0.0510(6) Uani 1 1 d . . . . .
C18 C 0.8738(3) 0.6329(3) -0.0310(3) 0.0568(9) Uani 1 1 d . . . . .
H18A H 0.9155 0.7095 -0.0501 0.085 Uiso 1 1 calc R U . . .
H18B H 0.9082 0.5683 -0.0641 0.085 Uiso 1 1 calc R U . . .
H18C H 0.8982 0.6499 0.0360 0.085 Uiso 1 1 calc R U . . .
O2 O 0.0655(2) 1.1086(2) 0.14271(16) 0.0539(6) Uani 1 1 d . . . . .
C19 C 0.4538(3) 1.3797(3) 0.3802(2) 0.0485(8) Uani 1 1 d . . . . .
H19A H 0.4946 1.4379 0.3435 0.073 Uiso 1 1 calc R U . . .
H19B H 0.5272 1.3744 0.4206 0.073 Uiso 1 1 calc R U . . .
H19C H 0.3906 1.4096 0.4181 0.073 Uiso 1 1 calc R U . . .
C20 C 0.3040(3) 1.1589(3) 0.3727(2) 0.0469(8) Uani 1 1 d . . . . .
H20A H 0.3748 1.1543 0.4156 0.070 Uiso 1 1 calc R U . . .
H20B H 0.2542 1.0756 0.3312 0.070 Uiso 1 1 calc R U . . .
H20C H 0.2392 1.1899 0.4080 0.070 Uiso 1 1 calc R U . . .
C21 C 0.9613(3) 0.8177(3) 0.3958(2) 0.0427(7) Uani 1 1 d . . . . .
C22 C 1.0498(3) 0.8549(3) 0.4776(2) 0.0512(9) Uani 1 1 d . . . . .
H22 H 1.1212 0.9345 0.4938 0.061 Uiso 1 1 calc R U . . .
C23 C 1.0358(3) 0.7772(3) 0.5369(2) 0.0441(8) Uani 1 1 d . . . . .
C24 C 0.9294(3) 0.6602(2) 0.51384(19) 0.0317(6) Uani 1 1 d . . . . .
C25 C 0.8391(3) 0.6256(3) 0.4324(2) 0.0404(7) Uani 1 1 d . . . . .
H25 H 0.7653 0.5476 0.4172 0.048 Uiso 1 1 calc R U . . .
C26 C 0.8538(3) 0.7022(3) 0.3726(2) 0.0432(7) Uani 1 1 d . . . . .
H26 H 0.7916 0.6763 0.3172 0.052 Uiso 1 1 calc R U . . .
C27 C 1.1237(4) 0.8238(3) 0.6293(3) 0.0835(15) Uani 1 1 d D . . . .
H27A H 1.0788 0.8683 0.6756 0.100 Uiso 1 1 calc R U . . .
H27B H 1.2142 0.8844 0.6247 0.100 Uiso 1 1 calc R U . . .
C28 C 1.1468(3) 0.7179(3) 0.6630(3) 0.0728(13) Uani 1 1 d D . . . .
H28A H 1.2135 0.6889 0.6270 0.087 Uiso 1 1 calc R U . . .
H28B H 1.1874 0.7504 0.7292 0.087 Uiso 1 1 calc R U . . .
C29 C 1.0159(3) 0.6098(3) 0.6528(2) 0.0407(7) Uani 1 1 d . . . . .
C30 C 0.9138(3) 0.5781(2) 0.57714(19) 0.0307(6) Uani 1 1 d . . . . .
N2 N 0.7978(2) 0.4741(2) 0.55888(16) 0.0323(5) Uani 1 1 d . . . . .
C31 C 0.7801(3) 0.3997(2) 0.6167(2) 0.0337(6) Uani 1 1 d . . . . .
C32 C 0.8753(3) 0.4247(2) 0.6945(2) 0.0347(6) Uani 1 1 d . . . . .
C33 C 0.9947(3) 0.5326(3) 0.7114(2) 0.0412(7) Uani 1 1 d . . . . .
H33 H 1.0613 0.5524 0.7636 0.049 Uiso 1 1 calc R U . . .
C34 C 0.8536(3) 0.3403(3) 0.7566(2) 0.0412(7) Uani 1 1 d . . . . .
C35 C 0.7279(3) 0.2218(3) 0.7282(2) 0.0485(8) Uani 1 1 d . . . . .
H35A H 0.7004 0.1945 0.7843 0.058 Uiso 1 1 calc R U . . .
H35B H 0.7531 0.1554 0.6865 0.058 Uiso 1 1 calc R U . . .
C36 C 0.6024(3) 0.2361(3) 0.6781(2) 0.0429(8) Uani 1 1 d . . . . .
C37 C 0.6500(3) 0.2844(3) 0.5936(2) 0.0457(8) Uani 1 1 d . . . . .
H37A H 0.6664 0.2169 0.5468 0.055 Uiso 1 1 calc R U . . .
H37B H 0.5747 0.3039 0.5653 0.055 Uiso 1 1 calc R U . . .
O3 O 0.9881(2) 0.9010(2) 0.34191(17) 0.0593(7) Uani 1 1 d . . . . .
C38 C 0.9041(4) 0.8632(3) 0.2541(3) 0.0611(10) Uani 1 1 d . . . . .
H38A H 0.9088 0.7841 0.2171 0.092 Uiso 1 1 calc R U . . .
H38B H 0.9377 0.9274 0.2210 0.092 Uiso 1 1 calc R U . . .
H38C H 0.8083 0.8523 0.2642 0.092 Uiso 1 1 calc R U . . .
O4 O 0.9349(2) 0.3653(2) 0.82670(16) 0.0582(7) Uani 1 1 d . . . . .
C39 C 0.4860(4) 0.1080(3) 0.6446(3) 0.0667(11) Uani 1 1 d . . . . .
H39A H 0.4568 0.0766 0.6982 0.100 Uiso 1 1 calc R U . . .
H39B H 0.5196 0.0492 0.6027 0.100 Uiso 1 1 calc R U . . .
H39C H 0.4076 0.1165 0.6116 0.100 Uiso 1 1 calc R U . . .
C40 C 0.5510(4) 0.3285(3) 0.7453(3) 0.0592(10) Uani 1 1 d . . . . .
H40A H 0.6262 0.4092 0.7680 0.089 Uiso 1 1 calc R U . . .
H40B H 0.5202 0.2955 0.7979 0.089 Uiso 1 1 calc R U . . .
H40C H 0.4738 0.3395 0.7127 0.089 Uiso 1 1 calc R U . . .
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'
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
O1 C1 C6 124.6(3) . . ?
O1 C1 C2 115.1(3) . . ?
C6 C1 C2 120.3(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 C7 121.3(3) . . ?
C4 C3 C7 118.6(3) . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 C10 122.0(2) . . ?
C3 C4 C10 119.9(2) . . ?
C6 C5 C4 121.8(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C3 C7 C8 110.0(2) . . ?
C3 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C3 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 110.6(2) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C13 C9 C10 117.8(3) . . ?
C13 C9 C8 124.2(3) . . ?
C10 C9 C8 118.0(3) . . ?
N1 C10 C9 122.8(3) . . ?
N1 C10 C4 117.8(2) . . ?
C9 C10 C4 119.4(2) . . ?
C11 N1 C10 118.3(2) . . ?
N1 C11 C12 122.7(3) . . ?
N1 C11 C17 116.6(2) . . ?
C12 C11 C17 120.7(2) . . ?
C13 C12 C11 117.8(3) . . ?
C13 C12 C14 121.3(2) . . ?
C11 C12 C14 120.8(3) . . ?
C9 C13 C12 120.5(3) . . ?
C9 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
O2 C14 C12 120.9(3) . . ?
O2 C14 C15 121.8(3) . . ?
C12 C14 C15 117.2(2) . . ?
C14 C15 C16 114.0(2) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C19 109.5(2) . . ?
C17 C16 C15 108.2(2) . . ?
C19 C16 C15 109.7(2) . . ?
C17 C16 C20 109.9(2) . . ?
C19 C16 C20 109.2(3) . . ?
C15 C16 C20 110.3(2) . . ?
C11 C17 C16 114.5(2) . . ?
C11 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C11 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C1 O1 C18 117.5(2) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 C22 115.7(3) . . ?
O3 C21 C26 124.5(3) . . ?
C22 C21 C26 119.8(3) . . ?
C21 C22 C23 121.1(3) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 119.7(3) . . ?
C22 C23 C27 120.3(3) . . ?
C24 C23 C27 119.7(3) . . ?
C25 C24 C23 118.4(2) . . ?
C25 C24 C30 121.9(2) . . ?
C23 C24 C30 119.7(2) . . ?
C24 C25 C26 122.0(3) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C25 C26 C21 118.9(3) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?
C23 C27 C28 112.5(3) . . ?
C23 C27 H27A 109.1 . . ?
C28 C27 H27A 109.1 . . ?
C23 C27 H27B 109.1 . . ?
C28 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C29 C28 C27 112.2(3) . . ?
C29 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C33 C29 C30 117.8(2) . . ?
C33 C29 C28 122.3(3) . . ?
C30 C29 C28 119.7(3) . . ?
N2 C30 C29 122.7(2) . . ?
N2 C30 C24 117.4(2) . . ?
C29 C30 C24 120.0(2) . . ?
C31 N2 C30 118.4(2) . . ?
N2 C31 C32 123.0(2) . . ?
N2 C31 C37 116.7(2) . . ?
C32 C31 C37 120.3(2) . . ?
C31 C32 C33 117.4(2) . . ?
C31 C32 C34 121.8(2) . . ?
C33 C32 C34 120.7(3) . . ?
C29 C33 C32 120.7(3) . . ?
C29 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
O4 C34 C32 121.4(3) . . ?
O4 C34 C35 122.0(3) . . ?
C32 C34 C35 116.6(3) . . ?
C34 C35 C36 114.0(2) . . ?
C34 C35 H35A 108.8 . . ?
C36 C35 H35A 108.8 . . ?
C34 C35 H35B 108.8 . . ?
C36 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C39 C36 C40 109.7(3) . . ?
C39 C36 C37 109.4(3) . . ?
C40 C36 C37 110.8(2) . . ?
C39 C36 C35 109.4(2) . . ?
C40 C36 C35 109.8(3) . . ?
C37 C36 C35 107.6(3) . . ?
C31 C37 C36 114.1(2) . . ?
C31 C37 H37A 108.7 . . ?
C36 C37 H37A 108.7 . . ?
C31 C37 H37B 108.7 . . ?
C36 C37 H37B 108.7 . . ?
H37A C37 H37B 107.6 . . ?
C21 O3 C38 117.5(2) . . ?
O3 C38 H38A 109.5 . . ?
O3 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O3 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C36 C40 H40A 109.5 . . ?
C36 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C36 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
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 O1 1.375(3) . ?
C1 C6 1.381(4) . ?
C1 C2 1.382(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.402(4) . ?
C3 C7 1.509(4) . ?
C4 C5 1.392(4) . ?
C4 C10 1.473(4) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.521(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.499(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C13 1.374(4) . ?
C9 C10 1.402(4) . ?
C10 N1 1.345(3) . ?
N1 C11 1.342(3) . ?
C11 C12 1.394(4) . ?
C11 C17 1.504(4) . ?
C12 C13 1.392(4) . ?
C12 C14 1.477(4) . ?
C13 H13 0.9400 . ?
C14 O2 1.222(3) . ?
C14 C15 1.491(4) . ?
C15 C16 1.530(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 C17 1.524(4) . ?
C16 C19 1.528(4) . ?
C16 C20 1.535(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
O1 C18 1.420(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 O3 1.369(3) . ?
C21 C22 1.370(4) . ?
C21 C26 1.383(4) . ?
C22 C23 1.387(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.389(4) . ?
C23 C27 1.484(4) . ?
C24 C25 1.380(4) . ?
C24 C30 1.472(3) . ?
C25 C26 1.382(4) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C27 C28 1.5217(19) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C28 C29 1.478(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C29 C33 1.370(4) . ?
C29 C30 1.393(4) . ?
C30 N2 1.350(3) . ?
N2 C31 1.337(3) . ?
C31 C32 1.389(4) . ?
C31 C37 1.504(4) . ?
C32 C33 1.397(4) . ?
C32 C34 1.476(4) . ?
C33 H33 0.9400 . ?
C34 O4 1.217(3) . ?
C34 C35 1.499(4) . ?
C35 C36 1.535(4) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C36 C39 1.523(4) . ?
C36 C40 1.525(5) . ?
C36 C37 1.528(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
O3 C38 1.418(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 H38C 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 H39C 0.9700 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 H40C 0.9700 . ?
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
O1 C1 C2 C3 -178.7(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 C3 C7 -179.3(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C7 C3 C4 C5 178.5(3) . . . . ?
C2 C3 C4 C10 179.5(3) . . . . ?
C7 C3 C4 C10 -1.8(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C10 C4 C5 C6 -178.8(2) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
O1 C1 C6 C5 179.3(3) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C3 C7 C8 -144.7(3) . . . . ?
C4 C3 C7 C8 36.6(4) . . . . ?
C3 C7 C8 C9 -55.2(4) . . . . ?
C7 C8 C9 C13 -142.1(3) . . . . ?
C7 C8 C9 C10 41.9(4) . . . . ?
C13 C9 C10 N1 -2.3(4) . . . . ?
C8 C9 C10 N1 174.0(2) . . . . ?
C13 C9 C10 C4 176.9(2) . . . . ?
C8 C9 C10 C4 -6.8(4) . . . . ?
C5 C4 C10 N1 -15.7(4) . . . . ?
C3 C4 C10 N1 164.6(2) . . . . ?
C5 C4 C10 C9 165.0(2) . . . . ?
C3 C4 C10 C9 -14.7(4) . . . . ?
C9 C10 N1 C11 0.5(4) . . . . ?
C4 C10 N1 C11 -178.7(2) . . . . ?
C10 N1 C11 C12 2.5(4) . . . . ?
C10 N1 C11 C17 -177.2(2) . . . . ?
N1 C11 C12 C13 -3.7(4) . . . . ?
C17 C11 C12 C13 176.0(2) . . . . ?
N1 C11 C12 C14 178.7(2) . . . . ?
C17 C11 C12 C14 -1.6(4) . . . . ?
C10 C9 C13 C12 1.0(4) . . . . ?
C8 C9 C13 C12 -175.0(3) . . . . ?
C11 C12 C13 C9 1.8(4) . . . . ?
C14 C12 C13 C9 179.4(2) . . . . ?
C13 C12 C14 O2 7.9(4) . . . . ?
C11 C12 C14 O2 -174.6(3) . . . . ?
C13 C12 C14 C15 -170.5(3) . . . . ?
C11 C12 C14 C15 7.0(4) . . . . ?
O2 C14 C15 C16 146.5(3) . . . . ?
C12 C14 C15 C16 -35.1(4) . . . . ?
C14 C15 C16 C17 55.4(3) . . . . ?
C14 C15 C16 C19 174.8(3) . . . . ?
C14 C15 C16 C20 -64.9(3) . . . . ?
N1 C11 C17 C16 -155.8(2) . . . . ?
C12 C11 C17 C16 24.5(4) . . . . ?
C19 C16 C17 C11 -169.1(2) . . . . ?
C15 C16 C17 C11 -49.6(3) . . . . ?
C20 C16 C17 C11 70.9(3) . . . . ?
C6 C1 O1 C18 -4.0(4) . . . . ?
C2 C1 O1 C18 175.4(3) . . . . ?
O3 C21 C22 C23 -178.2(3) . . . . ?
C26 C21 C22 C23 1.7(5) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
C21 C22 C23 C27 -174.1(4) . . . . ?
C22 C23 C24 C25 -0.8(5) . . . . ?
C27 C23 C24 C25 172.4(3) . . . . ?
C22 C23 C24 C30 -179.5(3) . . . . ?
C27 C23 C24 C30 -6.2(5) . . . . ?
C23 C24 C25 C26 1.7(5) . . . . ?
C30 C24 C25 C26 -179.7(3) . . . . ?
C24 C25 C26 C21 -0.8(5) . . . . ?
O3 C21 C26 C25 179.0(3) . . . . ?
C22 C21 C26 C25 -0.9(5) . . . . ?
C22 C23 C27 C28 -152.8(4) . . . . ?
C24 C23 C27 C28 34.0(5) . . . . ?
C23 C27 C28 C29 -46.7(5) . . . . ?
C27 C28 C29 C33 -150.6(4) . . . . ?
C27 C28 C29 C30 34.5(5) . . . . ?
C33 C29 C30 N2 -1.3(4) . . . . ?
C28 C29 C30 N2 173.8(3) . . . . ?
C33 C29 C30 C24 178.0(3) . . . . ?
C28 C29 C30 C24 -6.8(4) . . . . ?
C25 C24 C30 N2 -7.9(4) . . . . ?
C23 C24 C30 N2 170.7(3) . . . . ?
C25 C24 C30 C29 172.7(3) . . . . ?
C23 C24 C30 C29 -8.7(4) . . . . ?
C29 C30 N2 C31 0.8(4) . . . . ?
C24 C30 N2 C31 -178.5(2) . . . . ?
C30 N2 C31 C32 0.1(4) . . . . ?
C30 N2 C31 C37 -179.6(3) . . . . ?
N2 C31 C32 C33 -0.4(4) . . . . ?
C37 C31 C32 C33 179.3(3) . . . . ?
N2 C31 C32 C34 -179.4(3) . . . . ?
C37 C31 C32 C34 0.3(4) . . . . ?
C30 C29 C33 C32 1.0(5) . . . . ?
C28 C29 C33 C32 -174.0(3) . . . . ?
C31 C32 C33 C29 -0.2(4) . . . . ?
C34 C32 C33 C29 178.9(3) . . . . ?
C31 C32 C34 O4 -177.2(3) . . . . ?
C33 C32 C34 O4 3.8(5) . . . . ?
C31 C32 C34 C35 3.7(4) . . . . ?
C33 C32 C34 C35 -175.3(3) . . . . ?
O4 C34 C35 C36 147.7(3) . . . . ?
C32 C34 C35 C36 -33.1(4) . . . . ?
C34 C35 C36 C39 174.8(3) . . . . ?
C34 C35 C36 C40 -64.7(3) . . . . ?
C34 C35 C36 C37 56.0(4) . . . . ?
N2 C31 C37 C36 -154.9(3) . . . . ?
C32 C31 C37 C36 25.4(4) . . . . ?
C39 C36 C37 C31 -170.4(3) . . . . ?
C40 C36 C37 C31 68.5(3) . . . . ?
C35 C36 C37 C31 -51.6(3) . . . . ?
C22 C21 O3 C38 176.5(3) . . . . ?
C26 C21 O3 C38 -3.4(5) . . . . ?
