#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/00/4020099.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_4020099
loop_
_publ_author_name
'Shengming Ma'
'Bin Wu'
'Xuefeng Jiang'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2588
_journal_page_last               2593
_journal_paper_doi               10.1021/jo0480996
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C16 H18 Cl N O'
_chemical_formula_weight         275.76
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.905(3)
_cell_angle_beta                 103.761(3)
_cell_angle_gamma                101.298(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6640(16)
_cell_length_b                   9.2920(17)
_cell_length_c                   9.9179(19)
_cell_measurement_reflns_used    884
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      44.350
_cell_measurement_theta_min      4.461
_cell_volume                     720.8(2)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0852
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4229
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74793
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.427
_exptl_crystal_size_min          0.365
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.828
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0508
_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)+(0.0367P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                1615
_reflns_number_total             3029
_reflns_threshold_expression     >2sigma(I)
_cod_database_code               4020099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 1.04638(8) 0.25836(7) 0.79223(9) 0.0818(3) Uani 1 1 d . . .
O1 O 0.63848(19) -0.12288(17) 0.91114(18) 0.0647(5) Uani 1 1 d . . .
N1 N 0.6183(3) 0.1303(2) 0.9412(2) 0.0567(6) Uani 1 1 d . . .
C1 C 0.6780(3) 0.0078(3) 0.9044(2) 0.0505(6) Uani 1 1 d . . .
C2 C 0.8071(2) 0.1023(2) 0.8584(2) 0.0447(5) Uani 1 1 d . . .
C3 C 0.7361(3) 0.2387(3) 0.9023(3) 0.0486(6) Uani 1 1 d . . .
C4 C 0.6576(3) 0.3059(2) 0.7874(2) 0.0438(5) Uani 1 1 d . . .
C5 C 0.5528(4) 0.1853(3) 0.6425(3) 0.0551(7) Uani 1 1 d . . .
C6 C 0.4751(4) 0.2589(3) 0.5321(3) 0.0654(8) Uani 1 1 d . . .
C7 C 0.3769(4) 0.3626(3) 0.5939(3) 0.0635(7) Uani 1 1 d . . .
C8 C 0.4819(4) 0.4845(3) 0.7375(3) 0.0693(8) Uani 1 1 d . . .
C9 C 0.5599(4) 0.4124(3) 0.8478(3) 0.0613(7) Uani 1 1 d . . .
C10 C 0.9347(3) 0.0875(2) 0.8081(2) 0.0491(6) Uani 1 1 d . . .
C11 C 0.9942(3) -0.0500(3) 0.7623(2) 0.0506(6) Uani 1 1 d . . .
C12 C 1.1170(4) -0.0496(4) 0.6963(4) 0.0947(11) Uani 1 1 d . . .
C13 C 1.1691(5) -0.1792(4) 0.6529(4) 0.1118(12) Uani 1 1 d D . .
C14 C 1.0997(4) -0.3132(4) 0.6720(3) 0.0798(9) Uani 1 1 d . . .
C15 C 0.9784(3) -0.3174(3) 0.7386(3) 0.0725(8) Uani 1 1 d . . .
C16 C 0.9265(3) -0.1859(3) 0.7842(3) 0.0630(7) Uani 1 1 d . . .
H1 H 0.807(2) 0.315(2) 0.992(2) 0.043(6) Uiso 1 1 d . . .
H2 H 0.755(2) 0.371(2) 0.775(2) 0.049(6) Uiso 1 1 d . . .
H3 H 0.467(3) 0.121(2) 0.662(2) 0.065(7) Uiso 1 1 d . . .
H4 H 0.625(2) 0.124(2) 0.604(2) 0.056(6) Uiso 1 1 d . . .
H5 H 0.405(3) 0.179(3) 0.436(3) 0.088(8) Uiso 1 1 d . . .
H6 H 0.567(3) 0.319(3) 0.517(3) 0.075(9) Uiso 1 1 d . . .
H7 H 0.334(3) 0.411(2) 0.525(2) 0.068(7) Uiso 1 1 d . . .
H8 H 0.278(3) 0.297(2) 0.612(2) 0.071(7) Uiso 1 1 d . . .
H9 H 0.571(3) 0.555(3) 0.721(3) 0.076(8) Uiso 1 1 d . . .
H10 H 0.419(3) 0.549(2) 0.776(2) 0.070(7) Uiso 1 1 d . . .
H11 H 0.625(3) 0.491(3) 0.943(3) 0.090(9) Uiso 1 1 d . . .
H12 H 0.475(3) 0.351(2) 0.877(2) 0.056(7) Uiso 1 1 d . . .
H13 H 1.153(4) 0.042(3) 0.675(3) 0.122(12) Uiso 1 1 d . . .
H14 H 1.242(3) -0.183(4) 0.600(3) 0.144(14) Uiso 1 1 d D . .
H15 H 1.134(3) -0.400(3) 0.648(3) 0.087(9) Uiso 1 1 d . . .
H16 H 0.933(3) -0.405(3) 0.754(3) 0.103(11) Uiso 1 1 d . . .
H17 H 0.846(3) -0.192(2) 0.827(2) 0.059(7) Uiso 1 1 d . . .
H18 H 0.546(3) 0.138(2) 0.981(2) 0.056(7) Uiso 1 1 d . . .
