#------------------------------------------------------------------------------
#$Date: 2019-11-10 08:48:20 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225942 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/58/4515842.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_4515842
loop_
_publ_author_name
'Nongthombam, Geetmani Singh'
'Borah, Kasmika'
'Muinao, Thingreila'
'Silla, Yumnam'
'Pal, Mintu'
'Deka Boruah, Hari Prasanna'
'Boruah, Romesh Chandra'
_publ_section_title
;
 Synthesis of D-Ring Annulated Pyridosteroids from β-Formyl Enamides and
 Their Biological Evaluations.
;
_journal_issue                   1
_journal_name_full               'ACS combinatorial science'
_journal_page_first              11
_journal_page_last               27
_journal_paper_doi               10.1021/acscombsci.8b00140
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H39 N O4'
_chemical_formula_sum            'C33 H39 N O4'
_chemical_formula_weight         513.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.428(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.7787(6)
_cell_length_b                   5.9377(2)
_cell_length_c                   16.8849(7)
_cell_measurement_reflns_used    8799
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.19
_cell_measurement_theta_min      2.51
_cell_volume                     1413.66(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47829
_diffrn_reflns_theta_full        28.7138
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         1.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2067
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             552.2625
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.5181
_refine_diff_density_min         -0.3321
_refine_diff_density_rms         0.0585
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.0(14)
_refine_ls_d_res_high            0.7397
_refine_ls_d_res_low             16.1098
_refine_ls_goodness_of_fit_ref   1.0335
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    62
_refine_ls_number_parameters     346
_refine_ls_number_reflns         7218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0335
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0770P)²+0.2600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1547
_reflns_Friedel_coverage         0.985
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                5339
_reflns_number_total             7218
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            co8b00140_si_002.cif
_cod_data_source_block           rcb
_cod_database_code               4515842
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C(H), C4(H4), C13(H13), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C8(H8a,H8b), C9(H9a,H9b), C11(H11a,H11b), C12(H12a,H12b),
 C17(H17a,H17b), C1a(H1aa,H1ab), C1j(H1ja,H1jb)
2.c Aromatic/amide H refined with riding coordinates:
 C1g(H1g), C1k(H1k), C1i(H1i), C1d(H1d), C1e(H1e), C1b(H1b), C7(H7)
2.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C1c(H1ca,H1cb,H1cc), C1l(H1la,H1lb,H1lc), C1m(H1ma,H1mb,
 H1mc)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-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_refinement_flags_posn
N1 N 0.13327(12) 0.6606(3) 0.19752(11) 0.0397(4) Uani 1.000000 .
O O 0.44031(13) 1.0634(3) -0.31013(11) 0.0577(5) Uani 1.000000 .
C9 C 0.27793(15) 0.8955(3) -0.04590(13) 0.0336(4) Uani 1.000000 .
C5 C 0.37204(15) 1.1394(3) -0.11529(13) 0.0376(5) Uani 1.000000 .
C17 C 0.18672(15) 0.8133(4) 0.17397(13) 0.0370(5) Uani 1.000000 .
C28 C 0.08087(16) 0.4765(4) 0.30232(14) 0.0428(5) Uani 1.000000 .
C14 C 0.27763(14) 0.9807(4) 0.09820(12) 0.0333(4) Uani 1.000000 .
C11 C 0.18908(17) 0.7480(4) -0.05593(14) 0.0431(5) Uani 1.000000 .
O1 O 0.25638(14) 0.4868(4) 0.44482(11) 0.0664(6) Uani 1.000000 .
C13 C 0.18021(14) 0.8655(3) 0.08486(13) 0.0346(4) Uani 1.000000 .
C6 C 0.41542(16) 1.2293(4) -0.04118(14) 0.0415(5) Uani 1.000000 .
C7 C 0.38568(15) 1.1984(4) 0.03526(13) 0.0379(5) Uani 1.000000 .
C12 C 0.17548(16) 0.6671(4) 0.02632(14) 0.0415(5) Uani 1.000000 .
C16 C 0.25165(16) 0.9570(4) 0.22793(14) 0.0414(5) Uani 1.000000 .
C15 C 0.29521(17) 1.1159(4) 0.17959(13) 0.0426(5) Uani 1.000000 .
C4 C 0.40512(19) 1.1934(4) -0.18947(15) 0.0477(6) Uani 1.000000 .
C8 C 0.28885(14) 1.0849(3) 0.01901(12) 0.0332(4) Uani 1.000000 .
C10 C 0.28553(15) 0.9856(3) -0.13034(13) 0.0348(4) Uani 1.000000 .
C3 C 0.41606(17) 0.9846(4) -0.23719(14) 0.0475(6) Uani 1.000000 .
C18 C 0.09499(16) 1.0250(4) 0.05088(15) 0.0475(6) Uani 1.000000 .
C1 C 0.29909(19) 0.7820(4) -0.18355(14) 0.0433(5) Uani 1.000000 .
C23 C 0.21798(18) 0.7575(4) 0.33915(14) 0.0472(6) Uani 1.000000 .
C22 C 0.14747(16) 0.6355(4) 0.28000(13) 0.0412(5) Uani 1.000000 .
C2 C 0.32672(19) 0.8464(4) -0.26108(15) 0.0482(6) Uani 1.000000 .
C24 C 0.26776(19) 0.9266(4) 0.31218(15) 0.0490(6) Uani 1.000000 .
O2 O 0.49938(19) 0.7242(5) -0.32871(17) 0.0987(8) Uani 1.000000 .
O3 O 0.2737(3) 0.8457(4) 0.48274(14) 0.1120(11) Uani 1.000000 .
C19 C 0.19581(16) 1.1186(4) -0.17837(15) 0.0460(6) Uani 1.000000 .
C30 C -0.0055(2) 0.1255(5) 0.2780(2) 0.0658(8) Uani 1.000000 .
C29 C 0.05655(17) 0.2762(4) 0.25886(17) 0.0504(6) Uani 1.000000 .
C25 C 0.2492(2) 0.7061(5) 0.43011(16) 0.0601(7) Uani 1.000000 .
C33 C 0.03930(19) 0.5278(5) 0.36382(16) 0.0575(7) Uani 1.000000 .
C20 C 0.4842(2) 0.9226(7) -0.3484(2) 0.0743(10) Uani 1.000000 .
C31 C -0.0447(2) 0.1761(6) 0.3401(2) 0.0745(10) Uani 1.000000 .
C26 C 0.2887(3) 0.4098(7) 0.53087(19) 0.0919(12) Uani 1.000000 .
C32 C -0.0234(2) 0.3760(7) 0.3823(2) 0.0739(9) Uani 1.000000 .
C21 C 0.5091(3) 1.0365(8) -0.4180(2) 0.1042(15) Uani 1.000000 .
C27 C 0.2106(3) 0.3645(9) 0.5606(2) 0.1177(19) Uani 1.000000 .
H1g H 0.05330(19) 0.6631(5) 0.39261(16) 0.0691(8) Uiso 1.000000 R
H1k H -0.0511(2) 0.4105(7) 0.4235(2) 0.0887(11) Uiso 1.000000 R
H1i H -0.0857(2) 0.0746(6) 0.3535(2) 0.0894(12) Uiso 1.000000 R
H1d H -0.0205(2) -0.0092(5) 0.2489(2) 0.0790(9) Uiso 1.000000 R
H1e H 0.08224(17) 0.2424(4) 0.21627(17) 0.0605(7) Uiso 1.000000 R
H1b H 0.31096(19) 1.0171(4) 0.35032(15) 0.0588(7) Uiso 1.000000 R
H H 0.33251(15) 0.7956(3) -0.02409(13) 0.0404(5) Uiso 1.000000 R
H4 H 0.32391(14) 0.8576(4) 0.11190(12) 0.0399(5) Uiso 1.000000 R
H5a H 0.13350(17) 0.8333(4) -0.08620(14) 0.0517(6) Uiso 1.000000 R
H5b H 0.19312(17) 0.6173(4) -0.08916(14) 0.0517(6) Uiso 1.000000 R
H7 H 0.46846(16) 1.3184(4) -0.03676(14) 0.0498(6) Uiso 1.000000 R
H8a H 0.43301(15) 1.1082(4) 0.07472(13) 0.0455(6) Uiso 1.000000 R
H8b H 0.38368(15) 1.3445(4) 0.06036(13) 0.0455(6) Uiso 1.000000 R
H9a H 0.11450(16) 0.5929(4) 0.01534(14) 0.0498(6) Uiso 1.000000 R
H9b H 0.22451(16) 0.5589(4) 0.05238(14) 0.0498(6) Uiso 1.000000 R
H11a H 0.36232(17) 1.1389(4) 0.20689(13) 0.0511(6) Uiso 1.000000 R
H11b H 0.26303(17) 1.2602(4) 0.17028(13) 0.0511(6) Uiso 1.000000 R
H12a H 0.35978(19) 1.2939(4) -0.22617(15) 0.0572(7) Uiso 1.000000 R
H12b H 0.46553(19) 1.2711(4) -0.17086(15) 0.0572(7) Uiso 1.000000 R
H13 H 0.23883(14) 1.1971(3) -0.00223(12) 0.0399(5) Uiso 1.000000 R
H15 H 0.46832(17) 0.8932(4) -0.20277(14) 0.0570(7) Uiso 1.000000 R
H16a H 0.0382(2) 0.9527(13) 0.0544(11) 0.0713(9) Uiso 1.000000 GR
H16b H 0.1052(6) 1.1610(13) 0.0831(7) 0.0713(9) Uiso 1.000000 GR
H16c H 0.0885(8) 1.061(3) -0.0060(4) 0.0713(9) Uiso 1.000000 GR
H17a H 0.34783(19) 0.6844(4) -0.14919(14) 0.0520(6) Uiso 1.000000 R
H17b H 0.24048(19) 0.6966(4) -0.20059(14) 0.0520(6) Uiso 1.000000 R
H1aa H 0.27580(19) 0.9320(4) -0.29861(15) 0.0579(7) Uiso 1.000000 R
H1ab H 0.33651(19) 0.7110(4) -0.28964(15) 0.0579(7) Uiso 1.000000 R
H1ca H 0.1437(3) 1.0163(5) -0.1985(9) 0.0690(8) Uiso 1.000000 GR
H1cb H 0.1807(7) 1.227(2) -0.1420(3) 0.0690(8) Uiso 1.000000 GR
H1cc H 0.2074(4) 1.195(2) -0.2244(7) 0.0690(8) Uiso 1.000000 GR
H1ja H 0.3264(3) 0.2743(7) 0.53455(19) 0.1102(15) Uiso 1.000000 R
H1jb H 0.3284(3) 0.5245(7) 0.56520(19) 0.1102(15) Uiso 1.000000 R
H1la H 0.4522(3) 1.071(6) -0.4616(10) 0.156(2) Uiso 1.000000 GR
H1lb H 0.543(2) 1.173(3) -0.3981(6) 0.156(2) Uiso 1.000000 GR
H1lc H 0.548(2) 0.939(3) -0.4388(15) 0.156(2) Uiso 1.000000 GR
H1ma H 0.1692(15) 0.258(5) 0.5246(14) 0.177(3) Uiso 1.000000 GR
H1mb H 0.2331(4) 0.303(6) 0.6157(10) 0.177(3) Uiso 1.000000 GR
H1mc H 0.1766(16) 0.5015(13) 0.562(2) 0.177(3) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C22 N1 C17 117.19(19)
C20 O C3 119.0(2)
C8 C9 C11 113.28(17)
C10 C9 C11 112.71(16)
C10 C9 C8 112.26(16)
C4 C5 C6 120.6(2)
C10 C5 C6 122.53(19)
C10 C5 C4 116.83(18)
C13 C17 N1 124.58(19)
C16 C17 N1 124.8(2)
C16 C17 C13 110.50(18)
C29 C28 C22 119.7(2)
C33 C28 C22 121.5(2)
C33 C28 C29 118.7(2)
C15 C14 C13 105.08(17)
C8 C14 C13 113.06(16)
C8 C14 C15 122.34(17)
C12 C11 C9 114.49(17)
C26 O1 C25 118.6(3)
C14 C13 C17 99.59(16)
C12 C13 C17 117.63(18)
C12 C13 C14 107.19(17)
C18 C13 C17 107.31(17)
C18 C13 C14 113.76(18)
C18 C13 C12 111.05(18)
C7 C6 C5 125.3(2)
C8 C7 C6 113.60(17)
C13 C12 C11 110.54(17)
C15 C16 C17 110.43(18)
C24 C16 C17 117.6(2)
C24 C16 C15 131.9(2)
C16 C15 C14 99.83(17)
C3 C4 C5 112.39(19)
C14 C8 C9 108.11(16)
C7 C8 C9 109.95(17)
C7 C8 C14 111.25(16)
C5 C10 C9 109.79(16)
C1 C10 C9 108.62(16)
C1 C10 C5 108.33(18)
C19 C10 C9 111.67(18)
C19 C10 C5 108.95(17)
C19 C10 C1 109.42(17)
C4 C3 O 106.2(2)
C2 C3 O 111.51(19)
C2 C3 C4 111.4(2)
C2 C1 C10 114.42(18)
C24 C23 C22 119.2(2)
C25 C23 C22 123.9(2)
C25 C23 C24 116.7(2)
C28 C22 N1 114.79(19)
C23 C22 N1 121.8(2)
C23 C22 C28 123.4(2)
C1 C2 C3 110.15(19)
C23 C24 C16 118.9(2)
C31 C30 C29 119.7(3)
C30 C29 C28 121.0(3)
C23 C25 O1 112.1(2)
O3 C25 O1 123.8(3)
O3 C25 C23 123.8(3)
C32 C33 C28 119.9(3)
O2 C20 O 123.1(3)
C21 C20 O 111.5(3)
C21 C20 O2 125.4(3)
C32 C31 C30 120.1(3)
C27 C26 O1 110.8(3)
C31 C32 C33 120.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C17 1.339(3)
N1 C22 1.353(3)
O C3 1.459(3)
O C20 1.337(4)
C9 C11 1.545(3)
C9 C8 1.544(3)
C9 C10 1.558(3)
C5 C6 1.335(3)
C5 C4 1.509(3)
C5 C10 1.529(3)
C17 C13 1.511(3)
C17 C16 1.398(3)
C28 C22 1.491(3)
C28 C29 1.387(4)
C28 C33 1.389(3)
C14 C13 1.548(3)
C14 C15 1.545(3)
C14 C8 1.527(3)
C11 C12 1.538(3)
O1 C25 1.324(4)
O1 C26 1.460(3)
C13 C12 1.526(3)
C13 C18 1.543(3)
C6 C7 1.494(3)
C7 C8 1.531(3)
C16 C15 1.512(3)
C16 C24 1.382(3)
C4 C3 1.513(3)
C10 C1 1.554(3)
C10 C19 1.548(3)
C3 C2 1.504(3)
C1 C2 1.532(3)
C23 C22 1.409(3)
C23 C24 1.399(4)
C23 C25 1.497(3)
O2 C20 1.226(4)
O3 C25 1.190(3)
C30 C29 1.387(4)
C30 C31 1.374(5)
C33 C32 1.393(4)
C20 C21 1.494(5)
C31 C32 1.371(5)
C26 C27 1.415(5)
