#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/19/2221951.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221951
loop_
_publ_author_name
'Carvalho, Paulo'
'Furr, III, Edward B.'
'McCurdy, Christopher'
_publ_section_title
;(E)-Methyl
 2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyacrylate
 ethanol solvate
;
_journal_coeditor_code           BX2206
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1441
_journal_page_last               o1442
_journal_paper_doi               10.1107/S1600536809017309
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C23 H30 N2 O4 , C2 H6 O'
_chemical_formula_sum            'C25 H36 N2 O5'
_chemical_formula_weight         444.56
_chemical_name_common            Mitragynine
_chemical_name_systematic
;(E)-methyl
2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-\
octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyacrylate ethanol
solvate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.60450(10)
_cell_length_b                   11.7534(2)
_cell_length_c                   26.5735(4)
_cell_measurement_reflns_used    3152
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.55
_cell_measurement_theta_min      3.33
_cell_volume                     2375.11(6)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            34365
_diffrn_reflns_theta_full        66.39
_diffrn_reflns_theta_max         66.39
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.179
_refine_ls_abs_structure_details 'Flack (1983), 1758 Friedel pairs'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0469P)²+0.2771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                3649
_reflns_number_total             4158
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2206.cif
_cod_data_source_block           I
_cod_database_code               2221951
_cod_database_fobs_code          2221951
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C3 0.3530(3) 0.08591(16) 0.79611(7) 0.0226(4) Uani d . 1 . .
H H3 0.2920 0.0127 0.7987 0.027 Uiso calc R 1 . .
C C2 0.3100(3) 0.13687(16) 0.74583(7) 0.0224(4) Uani d . 1 . .
C C14 0.2990(3) 0.15900(16) 0.84110(7) 0.0224(4) Uani d . 1 . .
H H14A 0.1750 0.1778 0.8388 0.027 Uiso calc R 1 . .
H H14B 0.3657 0.2293 0.8412 0.027 Uiso calc R 1 . .
C C5 0.6061(3) 0.00338(18) 0.75273(7) 0.0269(5) Uani d . 1 . .
H H5A 0.5360 -0.0647 0.7479 0.032 Uiso calc R 1 . .
H H5B 0.7275 -0.0197 0.7574 0.032 Uiso calc R 1 . .
C C16 0.2800(3) 0.14709(17) 0.93877(7) 0.0237(4) Uani d . 1 . .
C C21 0.5794(3) -0.00691(16) 0.84300(7) 0.0245(4) Uani d . 1 . .
H H21A 0.7032 -0.0267 0.8439 0.029 Uiso calc R 1 . .
H H21B 0.5124 -0.0769 0.8405 0.029 Uiso calc R 1 . .
C C20 0.5303(3) 0.05433(16) 0.89183(7) 0.0228(4) Uani d . 1 . .
H H20 0.5406 -0.0014 0.9191 0.027 Uiso calc R 1 . .
C C7 0.4161(3) 0.13592(16) 0.70469(7) 0.0234(4) Uani d . 1 . .
C C11 0.0631(3) 0.29780(17) 0.60685(8) 0.0301(5) Uani d . 1 . .
H H11 -0.0215 0.3322 0.5867 0.036 Uiso calc R 1 . .
C C17 0.2551(3) 0.25695(16) 0.94916(7) 0.0257(4) Uani d . 1 . .
H H17 0.2198 0.2764 0.9815 0.031 Uiso calc R 1 . .
C C8 0.3190(3) 0.19029(16) 0.66512(7) 0.0231(4) Uani d . 1 . .
C C10 0.2287(3) 0.27195(17) 0.58613(7) 0.0281(5) Uani d . 1 . .
H H10 0.2523 0.2904 0.5528 0.034 Uiso calc R 1 . .
C C6 0.5923(3) 0.07864(19) 0.70579(8) 0.0286(5) Uani d . 1 . .
H H6A 0.6847 0.1355 0.7063 0.034 Uiso calc R 1 . .
H H6B 0.6070 0.0325 0.6758 0.034 Uiso calc R 1 . .
C C15 0.3348(3) 0.09212(16) 0.88976(7) 0.0226(4) Uani d . 1 . .
H H15 0.2658 0.0220 0.8871 0.027 Uiso calc R 1 . .
C C9 0.3566(3) 0.21944(17) 0.61479(7) 0.0246(4) Uani d . 1 . .
C C13 0.1537(3) 0.21960(17) 0.68469(7) 0.0241(4) Uani d . 1 . .
C C12 0.0231(3) 0.27357(17) 0.65616(7) 0.0281(4) Uani d . 1 . .
H H12 -0.0856 0.2921 0.6699 0.034 Uiso calc R 1 . .
C C19 0.6535(3) 0.15316(18) 0.90462(8) 0.0268(4) Uani d . 1 . .
H H19A 0.6527 0.2068 0.8769 0.032 Uiso calc R 1 . .
H H19B 0.6081 0.1923 0.9340 0.032 Uiso calc R 1 . .
C C18 0.8419(3) 0.1177(2) 0.91491(9) 0.0359(5) Uani d . 1 . .
H H18A 0.8946 0.0905 0.8844 0.054 Uiso calc R 1 . .
H H18B 0.8432 0.0583 0.9397 0.054 Uiso calc R 1 . .
H H18C 0.9071 0.1819 0.9272 0.054 Uiso calc R 1 . .
C C24 0.2472(3) 0.06448(17) 0.98062(7) 0.0245(4) Uani d . 1 . .
C C22 0.5687(3) 0.2261(2) 0.54835(8) 0.0362(5) Uani d . 1 . .
H H22A 0.5535 0.3068 0.5450 0.054 Uiso calc R 1 . .
H H22B 0.4941 0.1875 0.5247 0.054 Uiso calc R 1 . .
H H22C 0.6892 0.2066 0.5418 0.054 Uiso calc R 1 . .
C C25 0.2001(4) 0.0389(2) 1.06740(8) 0.0398(6) Uani d . 1 . .
H H25A 0.2861 -0.0208 1.0688 0.060 Uiso calc R 1 . .
H H25B 0.0856 0.0065 1.0623 0.060 Uiso calc R 1 . .
H H25C 0.2013 0.0808 1.0984 0.060 Uiso calc R 1 . .
C C23 0.2173(4) 0.45082(18) 0.93323(9) 0.0393(6) Uani d . 1 . .
H H23A 0.2795 0.4710 0.9634 0.059 Uiso calc R 1 . .
H H23B 0.0936 0.4468 0.9402 0.059 Uiso calc R 1 . .
H H23C 0.2384 0.5073 0.9079 0.059 Uiso calc R 1 . .
C C27 0.7975(3) 0.33626(19) 0.79406(9) 0.0404(6) Uani d . 1 . .
H H27A 0.6948 0.3492 0.8149 0.048 Uiso calc R 1 . .
H H27B 0.7713 0.3627 0.7603 0.048 Uiso calc R 1 . .
C C26 0.9507(4) 0.4008(2) 0.81476(12) 0.0505(7) Uani d . 1 . .
H H26A 1.0519 0.3881 0.7939 0.076 Uiso calc R 1 . .
H H26B 0.9750 0.3752 0.8484 0.076 Uiso calc R 1 . .
H H26C 0.9235 0.4806 0.8153 0.076 Uiso calc R 1 . .
N N2 0.5446(2) 0.06406(13) 0.79818(6) 0.0223(4) Uani d . 1 . .
N N1 0.1505(2) 0.18655(14) 0.73471(6) 0.0237(4) Uani d . 1 . .
H H1 0.0642 0.1955 0.7552 0.028 Uiso calc R 1 . .
O O5 0.83716(18) 0.21863(12) 0.79292(5) 0.0297(3) Uani d . 1 . .
H H5 0.7462 0.1818 0.7960 0.045 Uiso calc R 1 . .
O O3 0.2266(2) -0.03588(11) 0.97486(5) 0.0323(3) Uani d . 1 . .
O O2 0.2782(2) 0.34155(11) 0.91554(5) 0.0303(3) Uani d . 1 . .
O O1 0.52291(19) 0.19211(12) 0.59849(5) 0.0310(3) Uani d . 1 . .
O O4 0.2410(2) 0.11472(11) 1.02612(5) 0.0343(4) Uani d . 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C3 C2 . . 108.46(15) ?
N2 C3 C14 . . 109.44(16) ?
C2 C3 C14 . . 114.45(16) ?
N2 C3 H3 . . 108.1 ?
C2 C3 H3 . . 108.1 ?
C14 C3 H3 . . 108.1 ?
C7 C2 N1 . . 110.71(16) ?
C7 C2 C3 . . 125.74(18) ?
N1 C2 C3 . . 123.47(17) ?
C3 C14 C15 . . 108.83(15) ?
C3 C14 H14A . . 109.9 ?
C15 C14 H14A . . 109.9 ?
C3 C14 H14B . . 109.9 ?
C15 C14 H14B . . 109.9 ?
H14A C14 H14B . . 108.3 ?
N2 C5 C6 . . 111.38(16) ?
N2 C5 H5A . . 109.4 ?
C6 C5 H5A . . 109.4 ?
N2 C5 H5B . . 109.4 ?
C6 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C17 C16 C24 . . 116.77(17) ?
C17 C16 C15 . . 129.11(18) ?
C24 C16 C15 . . 114.11(16) ?
N2 C21 C20 . . 111.97(15) ?
N2 C21 H21A . . 109.2 ?
C20 C21 H21A . . 109.2 ?
N2 C21 H21B . . 109.2 ?
C20 C21 H21B . . 109.2 ?
H21A C21 H21B . . 107.9 ?
C21 C20 C19 . . 113.32(17) ?
C21 C20 C15 . . 109.77(16) ?
C19 C20 C15 . . 112.13(16) ?
C21 C20 H20 . . 107.1 ?
C19 C20 H20 . . 107.1 ?
C15 C20 H20 . . 107.1 ?
C2 C7 C8 . . 106.27(17) ?
C2 C7 C6 . . 121.23(18) ?
C8 C7 C6 . . 132.39(18) ?
C12 C11 C10 . . 121.73(19) ?
C12 C11 H11 . . 119.1 ?
C10 C11 H11 . . 119.1 ?
C16 C17 O2 . . 123.94(18) ?
C16 C17 H17 . . 118.0 ?
O2 C17 H17 . . 118.0 ?
C13 C8 C9 . . 118.26(18) ?
C13 C8 C7 . . 107.40(16) ?
C9 C8 C7 . . 134.32(19) ?
C9 C10 C11 . . 120.73(18) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C7 C6 C5 . . 109.66(16) ?
C7 C6 H6A . . 109.7 ?
C5 C6 H6A . . 109.7 ?
C7 C6 H6B . . 109.7 ?
C5 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
C16 C15 C14 . . 117.18(16) ?
C16 C15 C20 . . 110.83(16) ?
C14 C15 C20 . . 110.24(15) ?
C16 C15 H15 . . 105.9 ?
C14 C15 H15 . . 105.9 ?
C20 C15 H15 . . 105.9 ?
O1 C9 C10 . . 125.35(17) ?
O1 C9 C8 . . 115.38(17) ?
C10 C9 C8 . . 119.27(18) ?
N1 C13 C12 . . 129.34(18) ?
N1 C13 C8 . . 107.59(17) ?
C12 C13 C8 . . 123.07(18) ?
C11 C12 C13 . . 116.90(19) ?
C11 C12 H12 . . 121.5 ?
C13 C12 H12 . . 121.5 ?
C18 C19 C20 . . 114.17(18) ?
C18 C19 H19A . . 108.7 ?
C20 C19 H19A . . 108.7 ?
C18 C19 H19B . . 108.7 ?
C20 C19 H19B . . 108.7 ?
H19A C19 H19B . . 107.6 ?
C19 C18 H18A . . 109.5 ?
C19 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C19 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O3 C24 O4 . . 122.76(18) ?
O3 C24 C16 . . 124.37(17) ?
O4 C24 C16 . . 112.86(16) ?
O1 C22 H22A . . 109.5 ?
O1 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O1 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O4 C25 H25A . . 109.5 ?
O4 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
O4 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
O2 C23 H23A . . 109.5 ?
O2 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
O2 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
O5 C27 C26 . . 109.7(2) ?
O5 C27 H27A . . 109.7 ?
C26 C27 H27A . . 109.7 ?
O5 C27 H27B . . 109.7 ?
C26 C27 H27B . . 109.7 ?
H27A C27 H27B . . 108.2 ?
C27 C26 H26A . . 109.5 ?
C27 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C27 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C21 N2 C5 . . 109.23(14) ?
C21 N2 C3 . . 107.72(15) ?
C5 N2 C3 . . 111.39(15) ?
C2 N1 C13 . . 108.02(16) ?
C2 N1 H1 . . 126.0 ?
C13 N1 H1 . . 126.0 ?
C27 O5 H5 . . 109.5 ?
C17 O2 C23 . . 113.49(15) ?
C9 O1 C22 . . 116.81(16) ?
C24 O4 C25 . . 114.73(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 N2 . 1.481(3) ?
C3 C2 . 1.500(3) ?
C3 C14 . 1.528(2) ?
C3 H3 . 0.9800 ?
C2 C7 . 1.359(3) ?
C2 N1 . 1.378(3) ?
C14 C15 . 1.538(2) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C5 N2 . 1.479(2) ?
C5 C6 . 1.533(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C16 C17 . 1.334(3) ?
C16 C24 . 1.497(3) ?
C16 C15 . 1.512(3) ?
C21 N2 . 1.478(2) ?
C21 C20 . 1.530(3) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C20 C19 . 1.530(3) ?
C20 C15 . 1.553(3) ?
C20 H20 . 0.9800 ?
C7 C8 . 1.435(3) ?
C7 C6 . 1.500(3) ?
C11 C12 . 1.375(3) ?
C11 C10 . 1.408(3) ?
C11 H11 . 0.9300 ?
C17 O2 . 1.348(2) ?
C17 H17 . 0.9300 ?
C8 C13 . 1.403(3) ?
C8 C9 . 1.410(3) ?
C10 C9 . 1.381(3) ?
C10 H10 . 0.9300 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C15 H15 . 0.9800 ?
C9 O1 . 1.375(2) ?
C13 N1 . 1.385(2) ?
C13 C12 . 1.401(3) ?
C12 H12 . 0.9300 ?
C19 C18 . 1.517(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C24 O3 . 1.200(2) ?
C24 O4 . 1.346(2) ?
C22 O1 . 1.434(2) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C25 O4 . 1.447(2) ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
C23 O2 . 1.444(3) ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
C27 O5 . 1.415(3) ?
C27 C26 . 1.495(4) ?
C27 H27A . 0.9700 ?
C27 H27B . 0.9700 ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
N1 H1 . 0.8600 ?
O5 H5 . 0.8200 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O5 H5 N2 . 0.82 2.07 2.876(2) 169.1
N1 H1 O5 1_455 0.86 2.01 2.866(2) 170.4
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655779
