#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/00/4020098.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_4020098
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            'C14 H22 Cl N O'
_chemical_formula_weight         255.78
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.868(13)
_cell_length_b                   7.868(3)
_cell_length_c                   6.302(3)
_cell_measurement_reflns_used    2021
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.448
_cell_measurement_theta_min      5.177
_cell_volume                     1431.5(11)
_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  0.0941
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7200
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.41
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52406
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.373
_exptl_crystal_size_min          0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(17)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0764
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1356P)²+0.0228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2143
_reflns_number_gt                2080
_reflns_number_total             2513
_reflns_threshold_expression     >2sigma(I)
_cod_database_code               4020098
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.30199(4) 0.1211(2) 0.2103(3) 0.0945(6) Uani 1 1 d . . .
N1 N 0.45702(11) 0.0793(4) 0.2099(6) 0.0475(8) Uani 1 1 d D . .
H22 H 0.4857 0.0830 0.2471 0.057 Uiso 1 1 calc RD . .
O1 O 0.45035(10) -0.0387(4) -0.1287(5) 0.0542(8) Uani 1 1 d . . .
C1 C 0.43603(14) 0.0246(4) 0.0323(7) 0.0415(8) Uani 1 1 d . . .
C2 C 0.38995(14) 0.0722(4) 0.1209(7) 0.0434(9) Uani 1 1 d . . .
C3 C 0.41398(15) 0.1310(5) 0.3193(6) 0.0454(9) Uani 1 1 d D . .
C4 C 0.41068(14) 0.3157(5) 0.3833(7) 0.0470(9) Uani 1 1 d D . .
C5 C 0.44383(17) 0.3574(6) 0.5629(7) 0.0562(11) Uani 1 1 d . . .
H4 H 0.4376 0.2829 0.6821 0.067 Uiso 1 1 calc R . .
H3 H 0.4754 0.3367 0.5164 0.067 Uiso 1 1 calc R . .
C6 C 0.43944(19) 0.5376(6) 0.6330(7) 0.0589(11) Uani 1 1 d . . .
H5 H 0.4619 0.5601 0.7440 0.071 Uiso 1 1 calc R . .
H6 H 0.4088 0.5558 0.6916 0.071 Uiso 1 1 calc R . .
C7 C 0.4473(2) 0.6607(6) 0.4504(8) 0.0627(13) Uani 1 1 d . . .
H8 H 0.4422 0.7762 0.4989 0.075 Uiso 1 1 calc R . .
H7 H 0.4790 0.6517 0.4013 0.075 Uiso 1 1 calc R . .
C8 C 0.4144(2) 0.6211(6) 0.2695(7) 0.0648(14) Uani 1 1 d . . .
H9 H 0.4215 0.6945 0.1501 0.078 Uiso 1 1 calc R . .
H10 H 0.3829 0.6444 0.3140 0.078 Uiso 1 1 calc R . .
C9 C 0.41813(17) 0.4360(5) 0.1996(7) 0.0537(10) Uani 1 1 d . . .
H12 H 0.3952 0.4134 0.0907 0.064 Uiso 1 1 calc R . .
H11 H 0.4485 0.4161 0.1388 0.064 Uiso 1 1 calc R . .
C10 C 0.34730(15) 0.0552(6) 0.0483(9) 0.0591(11) Uani 1 1 d . . .
C11 C 0.33423(18) -0.0190(9) -0.1565(12) 0.0882(18) Uani 1 1 d D . .
H14 H 0.3611 -0.0217 -0.2491 0.106 Uiso 1 1 calc R . .
H13 H 0.3108 0.0514 -0.2231 0.106 Uiso 1 1 calc R . .
C12 C 0.3151(3) -0.2024(13) -0.1280(14) 0.149(4) Uani 1 1 d D . .
H16 H 0.3377 -0.2685 -0.0493 0.179 Uiso 1 1 calc R . .
H15 H 0.2871 -0.1970 -0.0433 0.179 Uiso 1 1 calc R . .
C13 C 0.3047(3) -0.2913(13) -0.3260(18) 0.142(3) Uiso 1 1 d D . .
H18 H 0.3310 -0.2871 -0.4217 0.171 Uiso 1 1 calc R . .
H17 H 0.2781 -0.2405 -0.3957 0.171 Uiso 1 1 calc R . .
C14 C 0.2942(4) -0.4755(16) -0.260(2) 0.166(5) Uiso 1 1 d . . .
H21 H 0.3227 -0.5335 -0.2295 0.249 Uiso 1 1 calc R . .
H20 H 0.2785 -0.5326 -0.3743 0.249 Uiso 1 1 calc R . .
H19 H 0.2748 -0.4755 -0.1366 0.249 Uiso 1 1 calc R . .
H1 H 0.407(4) 0.063(13) 0.442(12) 0.199 Uiso 1 1 d D . .
H2 H 0.3785(14) 0.334(13) 0.421(19) 0.199 Uiso 1 1 d D . .
