#------------------------------------------------------------------------------
#$Date: 2019-11-23 23:33:39 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235605 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/70/4037052.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_4037052
loop_
_publ_author_name
'Runyon, Scott P.'
'Kormos, Chad M.'
'Gichinga, Moses G.'
'Mascarella, S. Wayne'
'Navarro, Hernán A'
'Deschamps, Jeffrey R.'
'Imler, Gregory H.'
'Carroll, F. Ivy'
_publ_section_title
;
 Design, Synthesis, and Biological Evaluation of Structurally Rigid
 Analogues of 4-(3-Hydroxyphenyl)piperidine Opioid Receptor Antagonists.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10383
_journal_page_last               10391
_journal_paper_doi               10.1021/acs.joc.6b01366
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C12 H15 N O'
_chemical_formula_sum            'C12 H15 N O'
_chemical_formula_weight         189.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.693(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9239(3)
_cell_length_b                   16.0550(7)
_cell_length_c                   8.1077(4)
_cell_measurement_reflns_used    1164
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.77
_cell_measurement_theta_min      5.51
_cell_volume                     1013.54(8)
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.893
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.893
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_number            1643
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.706
_diffrn_reflns_theta_min         5.511
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.752989
_exptl_absorpt_correction_T_min  0.604608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       rod
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0778
_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)+(0.1203P)²+2.7420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2475
_refine_ls_wR_factor_ref         0.2697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1322
_reflns_number_total             1643
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b01366_si_003.cif
_cod_data_source_block           rti147
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037052
_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   0.888
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.7671(5) 0.1669(2) 0.1817(5) 0.0277(9) Uani 1 1 d . .
H1A H 0.8591 0.1518 0.1216 0.033 Uiso 1 1 calc R U
C2 C 0.5889(5) 0.1334(3) 0.1192(5) 0.0316(9) Uani 1 1 d . .
H2A H 0.5286 0.1670 0.0274 0.038 Uiso 1 1 calc R U
H2B H 0.5932 0.0763 0.0814 0.038 Uiso 1 1 calc R U
N3 N 0.5044(4) 0.1387(2) 0.2675(4) 0.0290(8) Uani 1 1 d . .
C3 C 0.3630(5) 0.0798(3) 0.2604(6) 0.0372(10) Uani 1 1 d . .
H3A H 0.3107 0.0871 0.3571 0.056 Uiso 1 1 calc R U
H3B H 0.4061 0.0240 0.2589 0.056 Uiso 1 1 calc R U
H3C H 0.2792 0.0895 0.1605 0.056 Uiso 1 1 calc R U
C4 C 0.6393(5) 0.1268(2) 0.4165(5) 0.0297(9) Uani 1 1 d . .
H4A H 0.6532 0.0682 0.4446 0.036 Uiso 1 1 calc R U
H4B H 0.6111 0.1565 0.5120 0.036 Uiso 1 1 calc R U
C5 C 0.8010(5) 0.1615(2) 0.3697(5) 0.0258(8) Uani 1 1 d . .
H5A H 0.9132 0.1422 0.4294 0.031 Uiso 1 1 calc R U
C6 C 0.7856(4) 0.2462(2) 0.2866(5) 0.0254(8) Uani 1 1 d . .
H6A H 0.6778 0.2756 0.2894 0.031 Uiso 1 1 calc R U
C7 C 0.9362(4) 0.3009(2) 0.2856(4) 0.0249(8) Uani 1 1 d . .
C8 C 1.0954(4) 0.2700(2) 0.2628(5) 0.0275(9) Uani 1 1 d . .
H8A H 1.1124 0.2128 0.2583 0.033 Uiso 1 1 calc R U
O9 O 1.3839(3) 0.29776(18) 0.2197(4) 0.0374(7) Uani 1 1 d . .
H9A H 1.3945 0.2478 0.2396 0.056 Uiso 1 1 calc R U
C9 C 1.2279(4) 0.3240(2) 0.2470(5) 0.0284(9) Uani 1 1 d . .
C10 C 1.2047(5) 0.4092(3) 0.2573(5) 0.0343(10) Uani 1 1 d . .
H10A H 1.2935 0.4455 0.2466 0.041 Uiso 1 1 calc R U
C11 C 1.0486(5) 0.4401(2) 0.2835(5) 0.0323(9) Uani 1 1 d . .
H11A H 1.0332 0.4973 0.2913 0.039 Uiso 1 1 calc R U
C12 C 0.9160(5) 0.3867(2) 0.2980(5) 0.0288(9) Uani 1 1 d . .
H12B H 0.8120 0.4081 0.3162 0.035 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 0.0181 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
C5 C1 C2 107.5(3)
C5 C1 C6 60.0(2)
C2 C1 C6 118.2(3)
C5 C1 H1A 118.8
C2 C1 H1A 118.8
C6 C1 H1A 118.8
N3 C2 C1 104.1(3)
N3 C2 H2A 110.9
C1 C2 H2A 110.9
N3 C2 H2B 110.9
C1 C2 H2B 110.9
H2A C2 H2B 109.0
C3 N3 C4 112.6(3)
C3 N3 C2 113.0(3)
C4 N3 C2 106.8(3)
N3 C3 H3A 109.5
N3 C3 H3B 109.5
H3A C3 H3B 109.5
N3 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
N3 C4 C5 105.6(3)
N3 C4 H4A 110.6
C5 C4 H4A 110.6
N3 C4 H4B 110.6
C5 C4 H4B 110.6
H4A C4 H4B 108.8
C1 C5 C4 106.1(3)
C1 C5 C6 60.7(2)
C4 C5 C6 116.2(3)
C1 C5 H5A 119.6
C4 C5 H5A 119.6
C6 C5 H5A 119.6
C7 C6 C5 122.4(3)
C7 C6 C1 119.1(3)
C5 C6 C1 59.2(2)
C7 C6 H6A 114.9
C5 C6 H6A 114.9
C1 C6 H6A 114.9
C12 C7 C8 118.6(3)
C12 C7 C6 118.8(3)
C8 C7 C6 122.5(3)
C9 C8 C7 120.5(4)
C9 C8 H8A 119.8
C7 C8 H8A 119.8
C9 O9 H9A 109.5
O9 C9 C10 116.7(3)
O9 C9 C8 123.1(3)
C10 C9 C8 120.1(3)
C9 C10 C11 119.7(4)
C9 C10 H10A 120.1
C11 C10 H10A 120.1
C12 C11 C10 120.4(4)
C12 C11 H11A 119.8
C10 C11 H11A 119.8
C11 C12 C7 120.6(3)
C11 C12 H12B 119.7
C7 C12 H12B 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C5 1.501(5)
C1 C2 1.508(5)
C1 C6 1.523(5)
C1 H1A 0.9800
C2 N3 1.484(5)
C2 H2A 0.9700
C2 H2B 0.9700
N3 C3 1.459(5)
N3 C4 1.470(5)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C4 C5 1.508(5)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.513(5)
C5 H5A 0.9800
C6 C7 1.483(5)
C6 H6A 0.9800
C7 C12 1.393(5)
C7 C8 1.399(5)
C8 C9 1.386(5)
C8 H8A 0.9300
O9 C9 1.363(4)
O9 H9A 0.8200
C9 C10 1.384(6)
C10 C11 1.385(5)
C10 H10A 0.9300
C11 C12 1.378(5)
C11 H11A 0.9300
C12 H12B 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9A N3 0.82 1.95 2.729(4) 158.3 1_655
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
C5 C1 C2 N3 19.8(4)
C6 C1 C2 N3 -45.1(4)
C1 C2 N3 C3 -155.6(3)
C1 C2 N3 C4 -31.3(4)
C3 N3 C4 C5 155.3(3)
C2 N3 C4 C5 30.7(4)
C2 C1 C5 C4 -1.5(4)
C6 C1 C5 C4 111.4(3)
C2 C1 C5 C6 -113.0(3)
N3 C4 C5 C1 -17.6(4)
N3 C4 C5 C6 47.2(4)
C1 C5 C6 C7 -107.0(4)
C4 C5 C6 C7 158.6(3)
C4 C5 C6 C1 -94.4(3)
C5 C1 C6 C7 112.5(4)
C2 C1 C6 C7 -152.6(3)
C2 C1 C6 C5 94.9(4)
C5 C6 C7 C12 -144.2(4)
C1 C6 C7 C12 145.7(4)
C5 C6 C7 C8 39.7(5)
C1 C6 C7 C8 -30.5(5)
C12 C7 C8 C9 -2.2(5)
C6 C7 C8 C9 173.9(4)
C7 C8 C9 O9 -178.0(3)
C7 C8 C9 C10 1.4(6)
O9 C9 C10 C11 179.4(4)
C8 C9 C10 C11 0.0(6)
C9 C10 C11 C12 -0.5(6)
C10 C11 C12 C7 -0.4(6)
C8 C7 C12 C11 1.7(6)
C6 C7 C12 C11 -174.5(4)
