#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/27/2202727.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_2202727
loop_
_publ_author_name
'Gathergood, Nicholas'
'Scammells, Peter J.'
'Fallon, Gary D.'
7,8-didehydro-4,5-epoxy-17-methylmorphinan-6-(naphthalene-1-carboxylate)
_publ_section_title
;
 7,8-Didehydro-4,5-epoxy-17-methylmorphinan-6-yl
 naphthalene-1-carboxylate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1918
_journal_page_last               o1919
_journal_paper_doi               10.1107/S1600536803025121
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C28 H25 N1 O4'
_chemical_formula_sum            'C28 H25 N O4'
_chemical_formula_weight         439.49
_chemical_melting_point          .443E-305
_chemical_name_common            'morphine 3-(1-naphthoate)'
_chemical_name_systematic
7,8-didehydro-4,5-epoxy-17-methylmorphinan-6-(naphthalene-1-carboxylate)
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 111.9000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.7421(2)
_cell_length_b                   7.19080(10)
_cell_length_c                   12.9536(3)
_cell_measurement_reflns_used    14873
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.8
_cell_volume                     1101.24(4)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14873
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       acicular
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0416P)²+0.1452P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                2423
_reflns_number_total             2909
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6134.cif
_cod_data_source_block           I
_cod_original_cell_volume        1101.23(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C28 H25 N1 O4'
_cod_database_code               2202727
_cod_database_fobs_code          2202727
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_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
_atom_site_type_symbol
C1 0.97625(15) 0.5834(3) 0.80473(14) 0.0197(4) Uani d . 1 . . C
C2 0.95002(15) 0.6995(3) 0.87606(15) 0.0217(4) Uani d . 1 . . C
C3 1.03452(17) 0.7424(3) 0.97782(15) 0.0246(4) Uani d . 1 . . C
H3 1.0170 0.8178 1.0294 0.030 Uiso calc R 1 . . H
C4 1.14411(16) 0.6770(3) 1.00531(15) 0.0243(4) Uani d . 1 . . C
H4 1.2013 0.7128 1.0738 0.029 Uiso calc R 1 . . H
C5 1.17139(15) 0.5579(3) 0.93257(15) 0.0213(4) Uani d . 1 . . C
C6 1.08361(15) 0.5091(3) 0.83582(14) 0.0180(4) Uani d . 1 . . C
C7 1.09088(15) 0.3931(3) 0.74229(14) 0.0196(4) Uani d . 1 . . C
C8 0.98416(16) 0.4608(3) 0.64533(15) 0.0215(4) Uani d . 1 . . C
H8 0.9469 0.3528 0.5969 0.026 Uiso calc R 1 . . H
C9 1.00760(16) 0.6150(3) 0.57366(14) 0.0243(4) Uani d . 1 . . C
H9 1.0198 0.5501 0.5108 0.029 Uiso calc R 1 . . H
C10 1.11380(16) 0.7231(3) 0.63347(15) 0.0258(4) Uani d . 1 . . C
H10 1.1150 0.8526 0.6196 0.031 Uiso calc R 1 . . H
C11 1.20582(17) 0.6431(3) 0.70494(16) 0.0269(4) Uani d . 1 . . C
H11 1.2729 0.7143 0.7381 0.032 Uiso calc R 1 . . H
C12 1.20539(16) 0.4407(3) 0.73428(16) 0.0238(4) Uani d . 1 . . C
H12 1.2150 0.3639 0.6740 0.029 Uiso calc R 1 . . H
C13 1.29713(16) 0.3860(3) 0.84632(17) 0.0261(4) Uani d . 1 . . C
H13 1.3718 0.4161 0.8415 0.031 Uiso calc R 1 . . H
C14 1.28953(16) 0.4995(3) 0.94609(16) 0.0274(4) Uani d . 1 . . C
H14A 1.3217 0.4235 1.0145 0.033 Uiso calc R 1 . . H
H14B 1.3369 0.6123 0.9566 0.033 Uiso calc R 1 . . H
C15 1.08588(17) 0.1840(3) 0.76422(16) 0.0255(4) Uani d . 1 . . C
H15A 1.0153 0.1564 0.7766 0.031 Uiso calc R 1 . . H
H15B 1.0839 0.1137 0.6978 0.031 Uiso calc R 1 . . H
C16 1.18642(18) 0.1202(3) 0.86447(17) 0.0300(5) Uani d . 1 . . C
H16A 1.1805 0.1712 0.9331 0.036 Uiso calc R 1 . . H
H16B 1.1861 -0.0172 0.8692 0.036 Uiso calc R 1 . . H
C17 1.39082(19) 0.1051(4) 0.94437(18) 0.0410(6) Uani d . 1 . . C
H17A 1.3874 -0.0310 0.9408 0.061 Uiso calc R 1 . . H
H17B 1.3917 0.1466 1.0168 0.061 Uiso calc R 1 . . H
H17C 1.4597 0.1477 0.9349 0.061 Uiso calc R 1 . . H
C18 0.79496(15) 0.8781(3) 0.75925(15) 0.0224(4) Uani d . 1 . . C
C19 0.67468(16) 0.9225(3) 0.73928(15) 0.0235(4) Uani d . 1 . . C
C20 0.61200(17) 0.7891(3) 0.76669(17) 0.0306(5) Uani d . 1 . . C
H20 0.6470 0.6765 0.8007 0.037 Uiso calc R 1 . . H
C21 0.49613(19) 0.8184(4) 0.7446(2) 0.0398(6) Uani d . 1 . . C
H21 0.4533 0.7250 0.7629 0.048 Uiso calc R 1 . . H
C22 0.44587(18) 0.9796(4) 0.69729(19) 0.0386(6) Uani d . 1 . . C
H22 0.3679 0.9979 0.6834 0.046 Uiso calc R 1 . . H
C23 0.50686(17) 1.1216(4) 0.66800(16) 0.0304(5) Uani d . 1 . . C
C24 0.45392(19) 1.2879(4) 0.61676(19) 0.0372(5) Uani d . 1 . . C
H24 0.3758 1.3056 0.6022 0.045 Uiso calc R 1 . . H
C25 0.51224(19) 1.4235(4) 0.58763(18) 0.0391(6) Uani d . 1 . . C
H25 0.4750 1.5340 0.5525 0.047 Uiso calc R 1 . . H
C26 0.62925(19) 1.3980(4) 0.61029(18) 0.0363(5) Uani d . 1 . . C
H26 0.6705 1.4930 0.5910 0.044 Uiso calc R 1 . . H
C27 0.68311(17) 1.2393(3) 0.65931(17) 0.0294(5) Uani d . 1 . . C
H27 0.7615 1.2256 0.6741 0.035 Uiso calc R 1 . . H
C28 0.62430(16) 1.0943(3) 0.68863(16) 0.0251(4) Uani d . 1 . . C
N1 1.29231(14) 0.1822(3) 0.85621(14) 0.0296(4) Uani d . 1 . . N
O1 0.90821(10) 0.5354(2) 0.69825(10) 0.0220(3) Uani d . 1 . . O
O2 0.91084(12) 0.7307(2) 0.52420(11) 0.0329(4) Uani d . 1 . . O
H2 0.8902 0.7733 0.5740 0.049 Uiso calc R 1 . . H
O3 0.83989(11) 0.7679(2) 0.85129(11) 0.0253(3) Uani d . 1 . . O
O4 0.84723(11) 0.9268(2) 0.70298(11) 0.0284(3) Uani d . 1 . . O
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_publ_flag
O1 C1 C2 127.39(16) y
O1 C1 C6 112.44(15) ?
C2 C1 C6 120.07(16) ?
C1 C2 C3 118.37(17) ?
C1 C2 O3 122.05(16) y
C3 C2 O3 119.51(16) ?
C4 C3 C2 121.14(17) ?
C4 C3 H3 119.4 ?
C2 C3 H3 119.4 ?
C3 C4 C5 120.65(17) ?
C3 C4 H4 119.7 ?
C5 C4 H4 119.7 ?
C6 C5 C4 116.33(17) ?
C6 C5 C14 118.11(17) ?
C4 C5 C14 125.14(17) ?
C5 C6 C1 123.13(17) ?
C5 C6 C7 126.97(17) ?
C1 C6 C7 109.39(15) ?
C6 C7 C15 112.05(15) ?
C6 C7 C12 106.01(15) ?
C15 C7 C12 109.64(16) ?
C6 C7 C8 100.37(15) ?
C15 C7 C8 111.98(16) ?
C12 C7 C8 116.34(15) y
O1 C8 C9 108.95(16) y
O1 C8 C7 105.49(13) y
C9 C8 C7 113.94(15) y
O1 C8 H8 109.4 ?
C9 C8 H8 109.4 ?
C7 C8 H8 109.4 ?
O2 C9 C10 113.09(17) y
O2 C9 C8 111.10(15) y
C10 C9 C8 113.60(15) y
O2 C9 H9 106.1 ?
C10 C9 H9 106.1 ?
C8 C9 H9 106.1 ?
C11 C10 C9 121.94(19) y
C11 C10 H10 119.0 ?
C9 C10 H10 119.0 ?
C10 C11 C12 120.73(19) y
C10 C11 H11 119.6 ?
C12 C11 H11 119.6 ?
C11 C12 C13 114.39(18) ?
C11 C12 C7 108.97(17) y
C13 C12 C7 106.59(15) ?
C11 C12 H12 108.9 ?
C13 C12 H12 108.9 ?
C7 C12 H12 108.9 ?
N1 C13 C12 107.15(17) ?
N1 C13 C14 115.47(18) ?
C12 C13 C14 112.80(16) ?
N1 C13 H13 107.0 ?
C12 C13 H13 107.0 ?
C14 C13 H13 107.0 ?
C5 C14 C13 114.61(16) ?
C5 C14 H14A 108.6 ?
C13 C14 H14A 108.6 ?
C5 C14 H14B 108.6 ?
C13 C14 H14B 108.6 ?
H14A C14 H14B 107.6 ?
C16 C15 C7 112.01(17) ?
C16 C15 H15A 109.2 ?
C7 C15 H15A 109.2 ?
C16 C15 H15B 109.2 ?
C7 C15 H15B 109.2 ?
H15A C15 H15B 107.9 ?
N1 C16 C15 110.68(16) ?
N1 C16 H16A 109.5 ?
C15 C16 H16A 109.5 ?
N1 C16 H16B 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 108.1 ?
N1 C17 H17A 109.5 ?
N1 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
N1 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
O4 C18 O3 123.25(16) y
O4 C18 C19 126.59(17) y
O3 C18 C19 110.15(15) y
C20 C19 C28 120.98(18) ?
C20 C19 C18 117.65(19) y
C28 C19 C18 121.31(17) y
C19 C20 C21 120.5(2) ?
C19 C20 H20 119.8 ?
C21 C20 H20 119.8 ?
C22 C21 C20 120.1(2) ?
C22 C21 H21 119.9 ?
C20 C21 H21 119.9 ?
C21 C22 C23 121.5(2) ?
C21 C22 H22 119.2 ?
C23 C22 H22 119.2 ?
C24 C23 C22 121.50(19) ?
C24 C23 C28 119.1(2) ?
C22 C23 C28 119.4(2) ?
C25 C24 C23 121.5(2) ?
C25 C24 H24 119.2 ?
C23 C24 H24 119.2 ?
C24 C25 C26 119.3(2) ?
C24 C25 H25 120.3 ?
C26 C25 H25 120.3 ?
C27 C26 C25 120.9(2) ?
C27 C26 H26 119.6 ?
C25 C26 H26 119.6 ?
C26 C27 C28 121.17(19) ?
C26 C27 H27 119.4 ?
C28 C27 H27 119.4 ?
C27 C28 C23 118.00(19) ?
C27 C28 C19 124.48(17) ?
C23 C28 C19 117.51(18) ?
C17 N1 C16 112.07(18) ?
C17 N1 C13 113.29(19) ?
C16 N1 C13 112.27(16) ?
C1 O1 C8 106.24(13) y
C9 O2 H2 109.5 ?
C18 O3 C2 117.36(14) y
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
C1 O1 . 1.372(2) y
C1 C2 . 1.376(3) y
C1 C6 . 1.381(2) ?
C2 C3 . 1.390(3) ?
C2 O3 . 1.406(2) y
C3 C4 . 1.388(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.410(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.378(3) ?
C5 C14 . 1.509(3) ?
C6 C7 . 1.502(2) ?
C7 C15 . 1.536(3) ?
C7 C12 . 1.540(3) y
C7 C8 . 1.546(3) y
C8 O1 . 1.480(2) y
C8 C9 . 1.545(3) y
C8 H8 . 1.0000 ?
C9 O2 . 1.426(2) y
C9 C10 . 1.501(3) y
C9 H9 . 1.0000 ?
C10 C11 . 1.324(3) y
C10 H10 . 0.9500 ?
C11 C12 . 1.504(3) y
C11 H11 . 0.9500 ?
C12 C13 . 1.537(3) ?
C12 H12 . 1.0000 ?
C13 N1 . 1.474(3) ?
C13 C14 . 1.562(3) ?
C13 H13 . 1.0000 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.516(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 N1 . 1.462(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 N1 . 1.455(3) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 O4 . 1.208(2) y
C18 O3 . 1.367(2) y
C18 C19 . 1.491(3) y
C19 C20 . 1.377(3) ?
C19 C28 . 1.433(3) ?
C20 C21 . 1.411(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.355(4) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.418(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.411(4) ?
C23 C28 . 1.432(3) ?
C24 C25 . 1.362(4) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.420(3) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.360(3) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.416(3) ?
C27 H27 . 0.9500 ?
O2 H2 . 0.8400 ?
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
O2 H2 O4 . 0.84 2.23 3.067(2) 171
C3 H3 Cg1 2_555 0.95 2.70 3.577(2) 154
C16 H16b Cg1 1_545 0.99 3.14 4.004(2) 146
C14 H14a Cg2 2_545 0.99 3.24 4.068(2) 143
C25 H25 Cg3 2_656 0.95 2.84 3.643(3) 143
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174590
