##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;\
(1R,2R,7S,8R,9R)-N-\
(2-Hydroxy-2,6,6,9-tetramethyl-12-\
oxatricyclo[7.2.1.0^1,7^]dodecan-8-yl)acetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H29 N O3'
_chemical_formula_sum     'C17 H29 N O3'
_chemical_formula_iupac     'C17 H29 N O3'
_chemical_formula_weight     295.416
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     14.5077(10)
_cell_length_b     7.9149(4)
_cell_length_c     14.8297(8)
_cell_angle_alpha     90
_cell_angle_beta     106.803(7)
_cell_angle_gamma     90
_cell_volume     1630.15(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6178
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     26.4
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.204
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     648
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.62777
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
                           'Rigaku Oxford Diffraction Xcalibur Eos Gemini ultra'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.1978
_diffrn_reflns_number     16240
_diffrn_reflns_av_R_equivalents     0.0626
_diffrn_reflns_theta_min     2.947
_diffrn_reflns_theta_max     26.369
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.976
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_refine_special_details
;
 All H atoms attached to C atoms were fixed geometrically and
treated as riding with C---H = 0.99 Å (methylene), 0.98 Å (methyl),
1.0Å (methine) with Uiso(H) = 1.2Ueq(CH and CH₂) or Uiso(H) =
1.5Ueq(CH₃). The coordinates of H atoms attached to N atoms were freely
refined with Uiso(H) = 1.2Ueq(N) and the H attached to hydroxyl O atoms
were fixed geometrically and treated as riding with O---H = 0.84Å and
Uiso(H) = 1.5Ueq(O).
;
_reflns_number_total     6178
_reflns_number_gt     4204
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0938
_refine_ls_R_factor_gt     0.0552
_refine_ls_wR_factor_gt     0.1022
_refine_ls_wR_factor_ref     0.1145
_refine_ls_goodness_of_fit_ref     0.990
_refine_ls_restrained_S_all     0.990
_refine_ls_number_reflns     6178
_refine_ls_number_parameters     391
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0496P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.200
_refine_diff_density_min     -0.234
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details     .
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'
_computing_data_collection
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_structure_solution
;
SHELXS2014(Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1A 0.6042(3) 0.9215(5) 0.3367(3) 0.0176(9) Uani d 1 . .
    C C1B 0.1521(3) 0.7991(5) 0.1239(3) 0.0184(9) Uani d 1 . .
    C C2A 0.5787(3) 1.1119(5) 0.3300(3) 0.0194(9) Uani d 1 . .
    C C2B 0.2228(3) 0.8563(5) 0.0698(3) 0.0234(10) Uani d 1 . .
    C C3A 0.5175(3) 1.1635(5) 0.2328(3) 0.0256(11) Uani d 1 . .
    H H3A1 0.5051 1.2838 0.2336 0.031 Uiso calc 1 . .
    H H3A2 0.4559 1.1062 0.2201 0.031 Uiso calc 1 . .
    C C3B 0.2688(3) 0.7124(6) 0.0319(3) 0.0283(11) Uani d 1 . .
    H H3B1 0.3157 0.7598 0.0039 0.034 Uiso calc 1 . .
    H H3B2 0.2193 0.6586 -0.0182 0.034 Uiso calc 1 . .
    C C4A 0.5593(3) 1.1271(5) 0.1517(3) 0.0277(11) Uani d 1 . .
    H H4A1 0.6267 1.1594 0.1703 0.033 Uiso calc 1 . .
    H H4A2 0.5263 1.1964 0.0982 0.033 Uiso calc 1 . .
    C C4B 0.3191(3) 0.5749(6) 0.1016(3) 0.0285(11) Uani d 1 . .
    H H4B1 0.3597 0.5086 0.0733 0.034 Uiso calc 1 . .
    H H4B2 0.3603 0.6285 0.1576 0.034 Uiso calc 1 . .
    C C5A 0.5511(4) 0.9415(6) 0.1212(3) 0.0282(11) Uani d 1 . .
    H H5A1 0.5453 0.9381 0.0544 0.034 Uiso calc 1 . .
    H H5A2 0.4914 0.8977 0.1289 0.034 Uiso calc 1 . .
    C C5B 0.2495(3) 0.4569(5) 0.1303(3) 0.0284(11) Uani d 1 . .
    H H5B1 0.2798 0.3468 0.1431 0.034 Uiso calc 1 . .
    H H5B2 0.1929 0.4441 0.0766 0.034 Uiso calc 1 . .
    C C6A 0.6328(3) 0.8185(5) 0.1716(3) 0.0216(10) Uani d 1 . .
    C C6B 0.2152(3) 0.5072(5) 0.2162(3) 0.0241(10) Uani d 1 . .
    C C7A 0.6721(3) 0.8589(5) 0.2791(3) 0.0162(9) Uani d 1 . .
    H H7A 0.7171 0.9526 0.2824 0.019 Uiso calc 1 . .
    C C7B 0.1981(3) 0.7020(5) 0.2176(3) 0.0188(9) Uani d 1 . .
    H H7B 0.2625 0.7511 0.2426 0.023 Uiso calc 1 . .
    C C8A 0.7331(3) 0.7213(5) 0.3489(3) 0.0182(9) Uani d 1 . .
    H H8A 0.7964 0.7716 0.3785 0.022 Uiso calc 1 . .
    C C8B 0.1376(3) 0.7772(5) 0.2814(3) 0.0204(10) Uani d 1 . .
    H H8B 0.1795 0.8595 0.3233 0.024 Uiso calc 1 . .
    C C9A 0.6804(4) 0.7145(5) 0.4250(3) 0.0248(11) Uani d 1 . .
    C C9B 0.0608(3) 0.8793(5) 0.2109(3) 0.0202(10) Uani d 1 . .
    C C10A 0.5781(3) 0.6436(5) 0.3840(3) 0.0274(11) Uani d 1 . .
    H H10A 0.5509 0.6087 0.4336 0.033 Uiso calc 1 . .
    H H10B 0.5778 0.5483 0.3428 0.033 Uiso calc 1 . .
    C C10B -0.0064(3) 0.7649(5) 0.1357(3) 0.0238(10) Uani d 1 . .
    H H10C -0.0236 0.6636 0.1638 0.029 Uiso calc 1 . .
    H H10D -0.0646 0.8243 0.1020 0.029 Uiso calc 1 . .
    C C11A 0.5228(3) 0.7952(5) 0.3287(3) 0.0273(11) Uani d 1 . .
    H H11C 0.4912 0.7658 0.2635 0.033 Uiso calc 1 . .
    H H11D 0.4753 0.8384 0.3574 0.033 Uiso calc 1 . .
    C C11B 0.0558(3) 0.7226(6) 0.0701(3) 0.0234(10) Uani d 1 . .
    H H11A 0.0608 0.6016 0.0625 0.028 Uiso calc 1 . .
    H H11B 0.0303 0.7747 0.0087 0.028 Uiso calc 1 . .
    C C12A 0.5288(4) 1.1601(5) 0.4038(3) 0.0295(11) Uani d 1 . .
    H H12D 0.5188 1.2800 0.4024 0.044 Uiso calc 1 . .
    H H12E 0.5684 1.1272 0.4650 0.044 Uiso calc 1 . .
    H H12F 0.4678 1.1033 0.3903 0.044 Uiso calc 1 . .
    C C12B 0.1739(4) 0.9771(6) -0.0103(3) 0.0367(13) Uani d 1 . .
    H H12A 0.2208 1.0201 -0.0387 0.055 Uiso calc 1 . .
    H H12B 0.1455 1.0692 0.0142 0.055 Uiso calc 1 . .
    H H12C 0.1247 0.9176 -0.0568 0.055 Uiso calc 1 . .
    C C13A 0.5922(4) 0.6396(6) 0.1448(3) 0.0292(11) Uani d 1 . .
    H H13D 0.6444 0.5607 0.1542 0.044 Uiso calc 1 . .
    H H13E 0.5547 0.6382 0.0798 0.044 Uiso calc 1 . .
    H H13F 0.5523 0.6084 0.1836 0.044 Uiso calc 1 . .
    C C13B 0.2971(4) 0.4656(6) 0.3050(3) 0.0340(12) Uani d 1 . .
    H H13A 0.3077 0.3457 0.3087 0.051 Uiso calc 1 . .
    H H13B 0.2800 0.5030 0.3596 0.051 Uiso calc 1 . .
    H H13C 0.3549 0.5218 0.3023 0.051 Uiso calc 1 . .
    C C14A 0.7174(4) 0.8430(6) 0.1309(3) 0.0321(12) Uani d 1 . .
    H H14D 0.6987 0.8084 0.0661 0.048 Uiso calc 1 . .
    H H14E 0.7709 0.7759 0.1658 0.048 Uiso calc 1 . .
    H H14F 0.7356 0.9600 0.1351 0.048 Uiso calc 1 . .
    C C14B 0.1300(4) 0.3921(5) 0.2153(3) 0.0328(12) Uani d 1 . .
    H H14A 0.1198 0.3926 0.2765 0.049 Uiso calc 1 . .
    H H14B 0.1436 0.2790 0.1995 0.049 Uiso calc 1 . .
    H H14C 0.0731 0.4326 0.1694 0.049 Uiso calc 1 . .
    C C15A 0.7375(4) 0.6418(6) 0.5174(3) 0.0401(14) Uani d 1 . .
    H H15A 0.7021 0.6542 0.5626 0.060 Uiso calc 1 . .
    H H15B 0.7978 0.7005 0.5393 0.060 Uiso calc 1 . .
    H H15C 0.7493 0.5242 0.5096 0.060 Uiso calc 1 . .
    C C15B 0.0104(4) 1.0103(5) 0.2527(3) 0.0305(11) Uani d 1 . .
    H H15D -0.0238 1.0867 0.2042 0.046 Uiso calc 1 . .
    H H15E 0.0570 1.0720 0.3005 0.046 Uiso calc 1 . .
    H H15F -0.0343 0.9558 0.2800 0.046 Uiso calc 1 . .
    C C16A 0.8330(3) 0.5161(5) 0.2981(3) 0.0244(10) Uani d 1 . .
    C C16B 0.1403(4) 0.6587(5) 0.4341(3) 0.0252(11) Uani d 1 . .
    C C17A 0.8449(4) 0.3346(5) 0.2726(3) 0.0346(12) Uani d 1 . .
    H H17A 0.9066 0.2938 0.3095 0.052 Uiso calc 1 . .
    H H17B 0.8407 0.3273 0.2069 0.052 Uiso calc 1 . .
    H H17C 0.7950 0.2671 0.2852 0.052 Uiso calc 1 . .
    C C17B 0.0852(4) 0.5607(6) 0.4879(3) 0.0427(14) Uani d 1 . .
    H H17D 0.0274 0.6209 0.4869 0.064 Uiso calc 1 . .
    H H17E 0.1241 0.5468 0.5518 0.064 Uiso calc 1 . .
    H H17F 0.0687 0.4518 0.4593 0.064 Uiso calc 1 . .
    N N1 0.7507(3) 0.5542(4) 0.3163(2) 0.0207(8) Uani d 1 . .
    H H1 0.7067 0.4781 0.3084 0.025 Uiso calc 1 . .
    N N2 0.0990(3) 0.6698(4) 0.3410(2) 0.0207(8) Uani d 1 . .
    H H2 0.0481 0.6115 0.3158 0.025 Uiso calc 1 . .
    O O1A 0.6662(2) 1.2086(3) 0.34675(18) 0.0217(7) Uani d 1 . .
    H H1A 0.6966 1.2028 0.4026 0.033 Uiso calc 1 . .
    O O1B 0.3005(2) 0.9460(4) 0.1336(2) 0.0299(8) Uani d 1 . .
    H H1B 0.2790 1.0098 0.1662 0.045 Uiso calc 1 . .
    O O2A 0.6627(2) 0.8915(3) 0.43286(17) 0.0228(7) Uani d 1 . .
    O O2B 0.1198(2) 0.9552(3) 0.15845(19) 0.0219(7) Uani d 1 . .
    O O3A 0.8965(2) 0.6211(4) 0.3013(2) 0.0354(8) Uani d 1 . .
    O O3B 0.2193(3) 0.7230(4) 0.4729(2) 0.0359(8) Uani d 1 . .
_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.
;
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
    C1A O2A . 1.453(5) ?
    C1A C11A . 1.526(6) ?
    C1A C2A . 1.548(5) ?
    C1A C7A . 1.560(5) ?
    C1B O2B . 1.465(5) ?
    C1B C11B . 1.520(6) ?
    C1B C2B . 1.542(6) ?
    C1B C7B . 1.560(6) ?
    C2A O1A . 1.442(5) ?
    C2A C3A . 1.514(6) ?
    C2A C12A . 1.524(5) ?
    C2B O1B . 1.432(5) ?
    C2B C3B . 1.508(6) ?
    C2B C12B . 1.530(6) ?
    C3A C4A . 1.524(6) ?
    C3A H3A1 . 0.9700 ?
    C3A H3A2 . 0.9700 ?
    C3B C4B . 1.532(6) ?
    C3B H3B1 . 0.9700 ?
    C3B H3B2 . 0.9700 ?
    C4A C5A . 1.532(6) ?
    C4A H4A1 . 0.9700 ?
    C4A H4A2 . 0.9700 ?
    C4B C5B . 1.523(6) ?
    C4B H4B1 . 0.9700 ?
    C4B H4B2 . 0.9700 ?
    C5A C6A . 1.549(6) ?
    C5A H5A1 . 0.9700 ?
    C5A H5A2 . 0.9700 ?
    C5B C6B . 1.548(5) ?
    C5B H5B1 . 0.9700 ?
    C5B H5B2 . 0.9700 ?
    C6A C14A . 1.529(6) ?
    C6A C13A . 1.541(6) ?
    C6A C7A . 1.563(5) ?
    C6B C13B . 1.533(6) ?
    C6B C14B . 1.533(6) ?
    C6B C7B . 1.563(6) ?
    C7A C8A . 1.586(5) ?
    C7A H7A . 0.9800 ?
    C7B C8B . 1.580(5) ?
    C7B H7B . 0.9800 ?
    C8A N1 . 1.456(5) ?
    C8A C9A . 1.536(5) ?
    C8A H8A . 0.9800 ?
    C8B N2 . 1.451(5) ?
    C8B C9B . 1.522(6) ?
    C8B H8B . 0.9800 ?
    C9A O2A . 1.435(5) ?
    C9A C15A . 1.496(6) ?
    C9A C10A . 1.537(6) ?
    C9B O2B . 1.443(5) ?
    C9B C15B . 1.502(6) ?
    C9B C10B . 1.544(6) ?
    C10A C11A . 1.543(6) ?
    C10A H10A . 0.9700 ?
    C10A H10B . 0.9700 ?
    C10B C11B . 1.542(6) ?
    C10B H10C . 0.9700 ?
    C10B H10D . 0.9700 ?
    C11A H11C . 0.9700 ?
    C11A H11D . 0.9700 ?
    C11B H11A . 0.9700 ?
    C11B H11B . 0.9700 ?
    C12A H12D . 0.9600 ?
    C12A H12E . 0.9600 ?
    C12A H12F . 0.9600 ?
    C12B H12A . 0.9600 ?
    C12B H12B . 0.9600 ?
    C12B H12C . 0.9600 ?
    C13A H13D . 0.9600 ?
    C13A H13E . 0.9600 ?
    C13A H13F . 0.9600 ?
    C13B H13A . 0.9600 ?
    C13B H13B . 0.9600 ?
    C13B H13C . 0.9600 ?
    C14A H14D . 0.9600 ?
    C14A H14E . 0.9600 ?
    C14A H14F . 0.9600 ?
    C14B H14A . 0.9600 ?
    C14B H14B . 0.9600 ?
    C14B H14C . 0.9600 ?
    C15A H15A . 0.9600 ?
    C15A H15B . 0.9600 ?
    C15A H15C . 0.9600 ?
    C15B H15D . 0.9600 ?
    C15B H15E . 0.9600 ?
    C15B H15F . 0.9600 ?
    C16A O3A . 1.232(5) ?
    C16A N1 . 1.332(5) ?
    C16A C17A . 1.508(6) ?
    C16B O3B . 1.234(5) ?
    C16B N2 . 1.339(5) ?
    C16B C17B . 1.498(6) ?
    C17A H17A . 0.9600 ?
    C17A H17B . 0.9600 ?
    C17A H17C . 0.9600 ?
    C17B H17D . 0.9600 ?
    C17B H17E . 0.9600 ?
    C17B H17F . 0.9600 ?
    N1 H1 . 0.8600 ?
    N2 H2 . 0.8600 ?
    O1A H1A . 0.8200 ?
    O1B H1B . 0.8200 ?
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
    O2A C1A C11A . . 100.9(3) ?
    O2A C1A C2A . . 106.4(3) ?
    C11A C1A C2A . . 117.9(3) ?
    O2A C1A C7A . . 101.7(3) ?
    C11A C1A C7A . . 110.3(3) ?
    C2A C1A C7A . . 116.9(3) ?
    O2B C1B C11B . . 100.4(3) ?
    O2B C1B C2B . . 105.2(3) ?
    C11B C1B C2B . . 119.6(3) ?
    O2B C1B C7B . . 101.6(3) ?
    C11B C1B C7B . . 111.3(3) ?
    C2B C1B C7B . . 115.5(3) ?
    O1A C2A C3A . . 105.4(3) ?
    O1A C2A C12A . . 108.7(3) ?
    C3A C2A C12A . . 110.3(4) ?
    O1A C2A C1A . . 108.9(3) ?
    C3A C2A C1A . . 112.7(3) ?
    C12A C2A C1A . . 110.6(3) ?
    O1B C2B C3B . . 105.8(4) ?
    O1B C2B C12B . . 107.6(4) ?
    C3B C2B C12B . . 109.8(3) ?
    O1B C2B C1B . . 108.5(3) ?
    C3B C2B C1B . . 113.9(3) ?
    C12B C2B C1B . . 111.0(4) ?
    C2A C3A C4A . . 116.3(4) ?
    C2A C3A H3A1 . . 108.2 ?
    C4A C3A H3A1 . . 108.2 ?
    C2A C3A H3A2 . . 108.2 ?
    C4A C3A H3A2 . . 108.2 ?
    H3A1 C3A H3A2 . . 107.4 ?
    C2B C3B C4B . . 117.4(3) ?
    C2B C3B H3B1 . . 107.9 ?
    C4B C3B H3B1 . . 107.9 ?
    C2B C3B H3B2 . . 107.9 ?
    C4B C3B H3B2 . . 107.9 ?
    H3B1 C3B H3B2 . . 107.2 ?
    C3A C4A C5A . . 113.5(4) ?
    C3A C4A H4A1 . . 108.9 ?
    C5A C4A H4A1 . . 108.9 ?
    C3A C4A H4A2 . . 108.9 ?
    C5A C4A H4A2 . . 108.9 ?
    H4A1 C4A H4A2 . . 107.7 ?
    C5B C4B C3B . . 113.6(4) ?
    C5B C4B H4B1 . . 108.9 ?
    C3B C4B H4B1 . . 108.9 ?
    C5B C4B H4B2 . . 108.9 ?
    C3B C4B H4B2 . . 108.9 ?
    H4B1 C4B H4B2 . . 107.7 ?
    C4A C5A C6A . . 118.5(4) ?
    C4A C5A H5A1 . . 107.7 ?
    C6A C5A H5A1 . . 107.7 ?
    C4A C5A H5A2 . . 107.7 ?
    C6A C5A H5A2 . . 107.7 ?
    H5A1 C5A H5A2 . . 107.1 ?
    C4B C5B C6B . . 118.0(4) ?
    C4B C5B H5B1 . . 107.8 ?
    C6B C5B H5B1 . . 107.8 ?
    C4B C5B H5B2 . . 107.8 ?
    C6B C5B H5B2 . . 107.8 ?
    H5B1 C5B H5B2 . . 107.2 ?
    C14A C6A C13A . . 107.8(3) ?
    C14A C6A C5A . . 108.6(3) ?
    C13A C6A C5A . . 105.7(4) ?
    C14A C6A C7A . . 106.2(4) ?
    C13A C6A C7A . . 116.8(3) ?
    C5A C6A C7A . . 111.5(3) ?
    C13B C6B C14B . . 107.6(4) ?
    C13B C6B C5B . . 107.3(4) ?
    C14B C6B C5B . . 106.9(3) ?
    C13B C6B C7B . . 106.7(3) ?
    C14B C6B C7B . . 117.1(4) ?
    C5B C6B C7B . . 110.8(3) ?
    C1A C7A C6A . . 121.4(3) ?
    C1A C7A C8A . . 100.5(3) ?
    C6A C7A C8A . . 119.7(3) ?
    C1A C7A H7A . . 104.4 ?
    C6A C7A H7A . . 104.4 ?
    C8A C7A H7A . . 104.4 ?
    C1B C7B C6B . . 120.2(3) ?
    C1B C7B C8B . . 100.3(3) ?
    C6B C7B C8B . . 119.8(3) ?
    C1B C7B H7B . . 104.9 ?
    C6B C7B H7B . . 104.9 ?
    C8B C7B H7B . . 104.9 ?
    N1 C8A C9A . . 112.6(3) ?
    N1 C8A C7A . . 121.6(3) ?
    C9A C8A C7A . . 101.6(3) ?
    N1 C8A H8A . . 106.7 ?
    C9A C8A H8A . . 106.7 ?
    C7A C8A H8A . . 106.7 ?
    N2 C8B C9B . . 113.3(4) ?
    N2 C8B C7B . . 121.5(3) ?
    C9B C8B C7B . . 102.2(3) ?
    N2 C8B H8B . . 106.3 ?
    C9B C8B H8B . . 106.3 ?
    C7B C8B H8B . . 106.3 ?
    O2A C9A C15A . . 111.4(3) ?
    O2A C9A C8A . . 99.5(3) ?
    C15A C9A C8A . . 115.1(4) ?
    O2A C9A C10A . . 102.3(4) ?
    C15A C9A C10A . . 115.9(4) ?
    C8A C9A C10A . . 110.6(3) ?
    O2B C9B C15B . . 111.7(3) ?
    O2B C9B C8B . . 99.2(3) ?
    C15B C9B C8B . . 115.5(3) ?
    O2B C9B C10B . . 101.8(3) ?
    C15B C9B C10B . . 114.9(4) ?
    C8B C9B C10B . . 111.7(3) ?
    C9A C10A C11A . . 102.7(3) ?
    C9A C10A H10A . . 111.2 ?
    C11A C10A H10A . . 111.2 ?
    C9A C10A H10B . . 111.2 ?
    C11A C10A H10B . . 111.2 ?
    H10A C10A H10B . . 109.1 ?
    C11B C10B C9B . . 102.7(3) ?
    C11B C10B H10C . . 111.2 ?
    C9B C10B H10C . . 111.2 ?
    C11B C10B H10D . . 111.2 ?
    C9B C10B H10D . . 111.2 ?
    H10C C10B H10D . . 109.1 ?
    C1A C11A C10A . . 101.3(4) ?
    C1A C11A H11C . . 111.5 ?
    C10A C11A H11C . . 111.5 ?
    C1A C11A H11D . . 111.5 ?
    C10A C11A H11D . . 111.5 ?
    H11C C11A H11D . . 109.3 ?
    C1B C11B C10B . . 101.5(3) ?
    C1B C11B H11A . . 111.5 ?
    C10B C11B H11A . . 111.5 ?
    C1B C11B H11B . . 111.5 ?
    C10B C11B H11B . . 111.5 ?
    H11A C11B H11B . . 109.3 ?
    C2A C12A H12D . . 109.5 ?
    C2A C12A H12E . . 109.5 ?
    H12D C12A H12E . . 109.5 ?
    C2A C12A H12F . . 109.5 ?
    H12D C12A H12F . . 109.5 ?
    H12E C12A H12F . . 109.5 ?
    C2B C12B H12A . . 109.5 ?
    C2B C12B H12B . . 109.5 ?
    H12A C12B H12B . . 109.5 ?
    C2B C12B H12C . . 109.5 ?
    H12A C12B H12C . . 109.5 ?
    H12B C12B H12C . . 109.5 ?
    C6A C13A H13D . . 109.5 ?
    C6A C13A H13E . . 109.5 ?
    H13D C13A H13E . . 109.5 ?
    C6A C13A H13F . . 109.5 ?
    H13D C13A H13F . . 109.5 ?
    H13E C13A H13F . . 109.5 ?
    C6B C13B H13A . . 109.5 ?
    C6B C13B H13B . . 109.5 ?
    H13A C13B H13B . . 109.5 ?
    C6B C13B H13C . . 109.5 ?
    H13A C13B H13C . . 109.5 ?
    H13B C13B H13C . . 109.5 ?
    C6A C14A H14D . . 109.5 ?
    C6A C14A H14E . . 109.5 ?
    H14D C14A H14E . . 109.5 ?
    C6A C14A H14F . . 109.5 ?
    H14D C14A H14F . . 109.5 ?
    H14E C14A H14F . . 109.5 ?
    C6B C14B H14A . . 109.5 ?
    C6B C14B H14B . . 109.5 ?
    H14A C14B H14B . . 109.5 ?
    C6B C14B H14C . . 109.5 ?
    H14A C14B H14C . . 109.5 ?
    H14B C14B H14C . . 109.5 ?
    C9A C15A H15A . . 109.5 ?
    C9A C15A H15B . . 109.5 ?
    H15A C15A H15B . . 109.5 ?
    C9A C15A H15C . . 109.5 ?
    H15A C15A H15C . . 109.5 ?
    H15B C15A H15C . . 109.5 ?
    C9B C15B H15D . . 109.5 ?
    C9B C15B H15E . . 109.5 ?
    H15D C15B H15E . . 109.5 ?
    C9B C15B H15F . . 109.5 ?
    H15D C15B H15F . . 109.5 ?
    H15E C15B H15F . . 109.5 ?
    O3A C16A N1 . . 122.9(4) ?
    O3A C16A C17A . . 120.9(4) ?
    N1 C16A C17A . . 116.2(4) ?
    O3B C16B N2 . . 122.1(4) ?
    O3B C16B C17B . . 122.2(4) ?
    N2 C16B C17B . . 115.8(4) ?
    C16A C17A H17A . . 109.5 ?
    C16A C17A H17B . . 109.5 ?
    H17A C17A H17B . . 109.5 ?
    C16A C17A H17C . . 109.5 ?
    H17A C17A H17C . . 109.5 ?
    H17B C17A H17C . . 109.5 ?
    C16B C17B H17D . . 109.5 ?
    C16B C17B H17E . . 109.5 ?
    H17D C17B H17E . . 109.5 ?
    C16B C17B H17F . . 109.5 ?
    H17D C17B H17F . . 109.5 ?
    H17E C17B H17F . . 109.5 ?
    C16A N1 C8A . . 121.8(4) ?
    C16A N1 H1 . . 119.1 ?
    C8A N1 H1 . . 119.1 ?
    C16B N2 C8B . . 122.1(4) ?
    C16B N2 H2 . . 119.0 ?
    C8B N2 H2 . . 119.0 ?
    C2A O1A H1A . . 109.5 ?
    C2B O1B H1B . . 109.5 ?
    C9A O2A C1A . . 98.5(3) ?
    C9B O2B C1B . . 97.8(3) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O2A C1A C2A O1A . . . . 63.2(4) ?
    C11A C1A C2A O1A . . . . 175.4(3) ?
    C7A C1A C2A O1A . . . . -49.5(4) ?
    O2A C1A C2A C3A . . . . 179.8(3) ?
    C11A C1A C2A C3A . . . . -68.0(4) ?
    C7A C1A C2A C3A . . . . 67.0(5) ?
    O2A C1A C2A C12A . . . . -56.2(4) ?
    C11A C1A C2A C12A . . . . 56.0(5) ?
    C7A C1A C2A C12A . . . . -169.0(3) ?
    O2B C1B C2B O1B . . . . 59.7(4) ?
    C11B C1B C2B O1B . . . . 171.4(3) ?
    C7B C1B C2B O1B . . . . -51.5(4) ?
    O2B C1B C2B C3B . . . . 177.2(3) ?
    C11B C1B C2B C3B . . . . -71.1(5) ?
    C7B C1B C2B C3B . . . . 66.0(4) ?
    O2B C1B C2B C12B . . . . -58.4(4) ?
    C11B C1B C2B C12B . . . . 53.3(5) ?
    C7B C1B C2B C12B . . . . -169.5(4) ?
    O1A C2A C3A C4A . . . . 61.4(4) ?
    C12A C2A C3A C4A . . . . 178.6(4) ?
    C1A C2A C3A C4A . . . . -57.2(5) ?
    O1B C2B C3B C4B . . . . 65.9(5) ?
    C12B C2B C3B C4B . . . . -178.2(4) ?
    C1B C2B C3B C4B . . . . -53.1(5) ?
    C2A C3A C4A C5A . . . . 77.3(5) ?
    C2B C3B C4B C5B . . . . 73.9(5) ?
    C3A C4A C5A C6A . . . . -87.9(5) ?
    C3B C4B C5B C6B . . . . -88.7(5) ?
    C4A C5A C6A C14A . . . . -78.9(4) ?
    C4A C5A C6A C13A . . . . 165.7(4) ?
    C4A C5A C6A C7A . . . . 37.8(5) ?
    C4B C5B C6B C13B . . . . -77.7(5) ?
    C4B C5B C6B C14B . . . . 167.1(4) ?
    C4B C5B C6B C7B . . . . 38.4(5) ?
    O2A C1A C7A C6A . . . . 163.0(3) ?
    C11A C1A C7A C6A . . . . 56.6(5) ?
    C2A C1A C7A C6A . . . . -81.6(5) ?
    O2A C1A C7A C8A . . . . 28.2(3) ?
    C11A C1A C7A C8A . . . . -78.2(4) ?
    C2A C1A C7A C8A . . . . 143.6(3) ?
    C14A C6A C7A C1A . . . . 154.1(3) ?
    C13A C6A C7A C1A . . . . -85.7(5) ?
    C5A C6A C7A C1A . . . . 35.9(5) ?
    C14A C6A C7A C8A . . . . -79.4(4) ?
    C13A C6A C7A C8A . . . . 40.8(5) ?
    C5A C6A C7A C8A . . . . 162.5(4) ?
    O2B C1B C7B C6B . . . . 161.6(4) ?
    C11B C1B C7B C6B . . . . 55.4(5) ?
    C2B C1B C7B C6B . . . . -85.1(5) ?
    O2B C1B C7B C8B . . . . 27.9(4) ?
    C11B C1B C7B C8B . . . . -78.3(4) ?
    C2B C1B C7B C8B . . . . 141.2(3) ?
    C13B C6B C7B C1B . . . . 155.4(4) ?
    C14B C6B C7B C1B . . . . -84.0(5) ?
    C5B C6B C7B C1B . . . . 38.9(5) ?
    C13B C6B C7B C8B . . . . -79.6(5) ?
    C14B C6B C7B C8B . . . . 40.9(6) ?
    C5B C6B C7B C8B . . . . 163.8(4) ?
    C1A C7A C8A N1 . . . . 133.3(4) ?
    C6A C7A C8A N1 . . . . -2.5(6) ?
    C1A C7A C8A C9A . . . . 7.3(4) ?
    C6A C7A C8A C9A . . . . -128.5(4) ?
    C1B C7B C8B N2 . . . . 135.4(4) ?
    C6B C7B C8B N2 . . . . 1.5(6) ?
    C1B C7B C8B C9B . . . . 8.0(4) ?
    C6B C7B C8B C9B . . . . -125.9(4) ?
    N1 C8A C9A O2A . . . . -172.7(3) ?
    C7A C8A C9A O2A . . . . -40.9(4) ?
    N1 C8A C9A C15A . . . . 68.1(5) ?
    C7A C8A C9A C15A . . . . -160.1(4) ?
    N1 C8A C9A C10A . . . . -65.6(4) ?
    C7A C8A C9A C10A . . . . 66.2(4) ?
    N2 C8B C9B O2B . . . . -174.4(3) ?
    C7B C8B C9B O2B . . . . -41.9(3) ?
    N2 C8B C9B C15B . . . . 66.0(5) ?
    C7B C8B C9B C15B . . . . -161.5(4) ?
    N2 C8B C9B C10B . . . . -67.7(4) ?
    C7B C8B C9B C10B . . . . 64.8(4) ?
    O2A C9A C10A C11A . . . . 28.0(4) ?
    C15A C9A C10A C11A . . . . 149.5(4) ?
    C8A C9A C10A C11A . . . . -77.2(4) ?
    O2B C9B C10B C11B . . . . 28.4(4) ?
    C15B C9B C10B C11B . . . . 149.3(3) ?
    C8B C9B C10B C11B . . . . -76.7(4) ?
    O2A C1A C11A C10A . . . . -38.5(3) ?
    C2A C1A C11A C10A . . . . -153.8(3) ?
    C7A C1A C11A C10A . . . . 68.4(4) ?
    C9A C10A C11A C1A . . . . 6.5(4) ?
    O2B C1B C11B C10B . . . . -39.5(4) ?
    C2B C1B C11B C10B . . . . -153.8(3) ?
    C7B C1B C11B C10B . . . . 67.5(4) ?
    C9B C10B C11B C1B . . . . 6.9(4) ?
    O3A C16A N1 C8A . . . . -5.1(6) ?
    C17A C16A N1 C8A . . . . 175.0(3) ?
    C9A C8A N1 C16A . . . . -140.3(4) ?
    C7A C8A N1 C16A . . . . 98.9(5) ?
    O3B C16B N2 C8B . . . . -8.7(6) ?
    C17B C16B N2 C8B . . . . 172.3(4) ?
    C9B C8B N2 C16B . . . . -135.4(4) ?
    C7B C8B N2 C16B . . . . 102.4(5) ?
    C15A C9A O2A C1A . . . . -177.5(4) ?
    C8A C9A O2A C1A . . . . 60.7(4) ?
    C10A C9A O2A C1A . . . . -52.9(3) ?
    C11A C1A O2A C9A . . . . 57.6(3) ?
    C2A C1A O2A C9A . . . . -178.9(3) ?
    C7A C1A O2A C9A . . . . -56.0(3) ?
    C15B C9B O2B C1B . . . . -176.7(3) ?
    C8B C9B O2B C1B . . . . 61.0(3) ?
    C10B C9B O2B C1B . . . . -53.6(3) ?
    C11B C1B O2B C9B . . . . 58.7(3) ?
    C2B C1B O2B C9B . . . . -176.6(3) ?
    C7B C1B O2B C9B . . . . -55.8(3) ?
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
    N1 H1 O1A 1_545 0.86 2.33 3.084(4) 147
    N2 H2 O3A 1_455 0.86 2.15 2.851(5) 139
    O1A H1A O3B 2_656 0.82 1.90 2.712(4) 169
    O1B H1B O2B . 0.82 2.32 2.752(4) 114
    C3A H3A2 O1B 1_555 0.97 2.58 3.516(5) 162
    C15A H15C O3B 2_646 0.96 2.43 3.369(6) 167
    C17A H17C O1A 1_545 0.96 2.35 3.252(6) 156
data_block
_journal_date_recd_electronic     2017-06-03
_journal_date_accepted     2017-07-01
_journal_name_full     'IUCrData'
_journal_year     2017
_journal_volume     2
_journal_issue      7
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314617009701
_journal_coeditor_code     HB4150
_publ_contact_author_name     'Dr Mazoir Noureddine'
_publ_contact_author_address
;
Laboratoire de Chimie des Substances Naturelles
"Unité Associé au CNRST (URAC16)"
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah,
Université Cadi Ayyad
40000 Marrakech, Morocco
;
_publ_contact_author_email     'mazoir17@gmail.com'
_publ_contact_author_fax     '0021224437408'
_publ_contact_author_phone     '0021224434649'
_publ_section_title
;\
(1R,2R,7S,8R,9R)-N-(2-Hydroxy-2,6,6,\
9-tetramethyl-12-oxatricyclo[7.2.1.0^1,7^]dodecan-8-yl)acetamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Benharref, Amed'
;
Laboratoire de Chimie des Substances Naturelles
"Unité Associé au CNRST (URAC16)"
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah,
Université Cadi Ayyad
40000 Marrakech, Morocco
;
    'Ait Elhad, Mustapha '
;
Laboratoire de Chimie des Substances Naturelles
"Unité Associé au CNRST (URAC16)"
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah,
Université Cadi Ayyad
40000 Marrakech, Morocco
;
    'Mazoir, Noureddine'
;
Laboratoire de Chimie des Substances Naturelles
"Unité Associé au CNRST (URAC16)"
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah,
Université Cadi Ayyad
40000 Marrakech, Morocco
;
    'Daran, Jean-Claude'
;
Laboratoire de Chimie de Coordination, 205 route de Narbonne,
 31077 Toulouse Cedex 04, France
;
    'Oukhrib, Abdelouahd '
;
Laboratoire de Chimie des Substances Naturelles
"Unité Associé au CNRST (URAC16)"
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah,
Université Cadi Ayyad
40000 Marrakech, Morocco
;
    'Berraho, Moha'
;
Laboratoire de Chimie des Substances Naturelles
"Unité Associé au CNRST (URAC16)"
Faculté des Sciences Semlalia,
BP 2390 Bd My Abdellah,
Université Cadi Ayyad
40000 Marrakech, Morocco
;
_publ_section_synopsis
;
The asymmetric unit of the title compound contains two independent molecules,
one of which features an intramolecular O---H...O hydrogen bond. In the
crystal, the molecules are linked by N---H...O and O---H...O hydrogen bonds
forming helical chains propagating along the b-axis direction.
;
