#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/38/7103860.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_7103860
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/b305159e
_journal_year                    2003
_chemical_formula_structural     C17H21NO3
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             02/12/2003
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.12(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.75(2)
_cell_length_b                   5.316(5)
_cell_length_c                   12.868(13)
_cell_measurement_reflns_used    297
_cell_measurement_temperature    137(2)
_cell_measurement_theta_max      22.87
_cell_measurement_theta_min      2.40
_cell_volume                     1487(2)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999), XTEL (local package)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      137(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 44.52
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
'   0.30 degree frames measured for  64.59 seconds each'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_measurement_method       'ω 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  0.3471
_diffrn_reflns_av_sigmaI/netI    0.5230
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9184
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_id                MSC03032
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.760
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3511
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.760
_refine_ls_R_factor_all          0.3102
_refine_ls_R_factor_gt           0.0892
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0466P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.2262
_reflns_number_gt                844
_reflns_number_total             3511
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b305159e.txt
_cod_data_source_block           03032
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C2   '
_cod_database_code               7103860
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
O1 O 0.3445(3) 0.0440(11) 0.0511(5) 0.0472(18) Uani 1 1 d . . .
C2 C 0.2970(4) -0.0176(18) 0.0868(6) 0.034(2) Uani 1 1 d . . .
O3 O 0.2444(3) 0.0944(11) 0.0584(4) 0.0378(15) Uani 1 1 d . . .
C4 C 0.1947(4) -0.0022(16) 0.1146(6) 0.036(2) Uani 1 1 d . . .
H22 H 0.1611 -0.0549 0.0664 0.044 Uiso 1 1 calc R . .
H23 H 0.1786 0.1276 0.1620 0.044 Uiso 1 1 calc R . .
C5 C 0.2191(3) -0.2301(16) 0.1773(6) 0.026(2) Uani 1 1 d . . .
H24 H 0.2038 -0.3897 0.1447 0.031 Uiso 1 1 calc R . .
N6 N 0.2842(3) -0.2004(14) 0.1587(5) 0.0307(17) Uani 1 1 d . . .
C7 C 0.3216(4) -0.396(2) 0.1893(7) 0.036(2) Uani 1 1 d . . .
O8 O 0.3014(3) -0.5688(12) 0.2365(5) 0.0448(18) Uani 1 1 d . . .
C9 C 0.3903(3) -0.377(2) 0.1727(7) 0.041(3) Uani 1 1 d . . .
H26 H 0.4030 -0.5167 0.1269 0.050 Uiso 1 1 calc R . .
H25 H 0.3991 -0.2174 0.1365 0.050 Uiso 1 1 calc R . .
C10 C 0.4272(4) -0.387(2) 0.2687(7) 0.048(3) Uani 1 1 d . . .
H27 H 0.4153 -0.5421 0.3077 0.058 Uiso 1 1 calc R . .
C11 C 0.4100(5) -0.156(3) 0.3348(10) 0.097(5) Uani 1 1 d . . .
H28 H 0.4140 -0.0031 0.2930 0.146 Uiso 1 1 calc R . .
H30 H 0.4376 -0.1459 0.3958 0.146 Uiso 1 1 calc R . .
H29 H 0.3674 -0.1728 0.3576 0.146 Uiso 1 1 calc R . .
C12 C 0.4946(4) -0.403(2) 0.2472(7) 0.053(3) Uani 1 1 d . . .
H31 H 0.5004 -0.5483 0.1991 0.064 Uiso 1 1 calc R . .
C13 C 0.5307(4) -0.463(2) 0.3478(8) 0.083(4) Uani 1 1 d . . .
H33 H 0.5747 -0.4697 0.3334 0.124 Uiso 1 1 calc R . .
H34 H 0.5173 -0.6261 0.3748 0.124 Uiso 1 1 calc R . .
H32 H 0.5230 -0.3319 0.3995 0.124 Uiso 1 1 calc R . .
C14 C 0.5209(4) -0.188(3) 0.1992(10) 0.078(4) Uani 1 1 d . . .
H35 H 0.5220 -0.0388 0.2396 0.093 Uiso 1 1 calc R . .
C15 C 0.5441(5) -0.172(4) 0.1043(10) 0.154(8) Uani 1 1 d . . .
H37 H 0.5443 -0.3150 0.0602 0.185 Uiso 1 1 calc R . .
H36 H 0.5605 -0.0166 0.0808 0.185 Uiso 1 1 calc R . .
C16 C 0.2020(3) -0.2221(18) 0.2860(6) 0.028(2) Uani 1 1 d . . .
C17 C 0.2190(3) -0.0379(15) 0.3534(6) 0.0232(19) Uani 1 1 d . . .
H39 H 0.2459 0.0897 0.3297 0.028 Uiso 1 1 calc R . .
C18 C 0.1996(4) -0.0257(16) 0.4524(7) 0.033(2) Uani 1 1 d . . .
H40 H 0.2117 0.1108 0.4959 0.040 Uiso 1 1 calc R . .
C19 C 0.1624(4) -0.2123(19) 0.4896(6) 0.035(2) Uani 1 1 d . . .
H41 H 0.1493 -0.2093 0.5595 0.042 Uiso 1 1 calc R . .
C20 C 0.1444(4) -0.405(2) 0.4234(7) 0.042(2) Uani 1 1 d . . .
H42 H 0.1188 -0.5363 0.4479 0.050 Uiso 1 1 calc R . .
C21 C 0.1633(3) -0.4057(19) 0.3226(7) 0.034(2) Uani 1 1 d . . .
H43 H 0.1496 -0.5354 0.2770 0.041 Uiso 1 1 calc R . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 O3 121.3(8) . . ?
O1 C2 N6 130.3(8) . . ?
O3 C2 N6 108.5(7) . . ?
C2 O3 C4 111.0(7) . . ?
O3 C4 C5 107.2(6) . . ?
N6 C5 C16 115.0(6) . . ?
N6 C5 C4 98.9(6) . . ?
C16 C5 C4 112.9(8) . . ?
C7 N6 C2 127.1(7) . . ?
C7 N6 C5 116.4(7) . . ?
C2 N6 C5 113.5(7) . . ?
O8 C7 N6 120.7(7) . . ?
O8 C7 C9 119.7(9) . . ?
N6 C7 C9 119.3(9) . . ?
C10 C9 C7 113.9(7) . . ?
C9 C10 C12 111.7(7) . . ?
C9 C10 C11 107.5(9) . . ?
C12 C10 C11 113.2(9) . . ?
C14 C12 C10 116.0(10) . . ?
C14 C12 C13 109.3(9) . . ?
C10 C12 C13 110.0(8) . . ?
C15 C14 C12 127.9(16) . . ?
C17 C16 C21 117.0(8) . . ?
C17 C16 C5 124.4(8) . . ?
C21 C16 C5 118.4(9) . . ?
C18 C17 C16 123.5(8) . . ?
C17 C18 C19 119.4(8) . . ?
C18 C19 C20 118.9(8) . . ?
C21 C20 C19 119.9(9) . . ?
C20 C21 C16 121.3(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.184(9) . ?
C2 O3 1.334(9) . ?
C2 N6 1.374(10) . ?
O3 C4 1.408(8) . ?
C4 C5 1.543(11) . ?
C5 N6 1.450(9) . ?
C5 C16 1.456(10) . ?
N6 C7 1.371(11) . ?
C7 O8 1.190(11) . ?
C7 C9 1.518(10) . ?
C9 C10 1.461(11) . ?
C10 C12 1.498(11) . ?
C10 C11 1.545(14) . ?
C12 C14 1.423(16) . ?
C12 C13 1.534(12) . ?
C14 C15 1.334(14) . ?
C16 C17 1.354(11) . ?
C16 C21 1.377(11) . ?
C17 C18 1.352(10) . ?
C18 C19 1.372(11) . ?
C19 C20 1.384(13) . ?
C20 C21 1.369(11) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 O3 C4 -177.3(9) . . . . ?
N6 C2 O3 C4 2.9(9) . . . . ?
C2 O3 C4 C5 -7.9(9) . . . . ?
O3 C4 C5 N6 9.2(8) . . . . ?
O3 C4 C5 C16 131.2(7) . . . . ?
O1 C2 N6 C7 -16.4(16) . . . . ?
O3 C2 N6 C7 163.4(8) . . . . ?
O1 C2 N6 C5 -176.0(10) . . . . ?
O3 C2 N6 C5 3.9(9) . . . . ?
C16 C5 N6 C7 69.7(10) . . . . ?
C4 C5 N6 C7 -169.9(7) . . . . ?
C16 C5 N6 C2 -128.5(8) . . . . ?
C4 C5 N6 C2 -8.0(8) . . . . ?
C2 N6 C7 O8 -165.3(8) . . . . ?
C5 N6 C7 O8 -6.3(12) . . . . ?
C2 N6 C7 C9 21.2(13) . . . . ?
C5 N6 C7 C9 -179.7(8) . . . . ?
O8 C7 C9 C10 -54.7(14) . . . . ?
N6 C7 C9 C10 118.8(9) . . . . ?
C7 C9 C10 C12 172.4(10) . . . . ?
C7 C9 C10 C11 -62.8(11) . . . . ?
C9 C10 C12 C14 66.0(14) . . . . ?
C11 C10 C12 C14 -55.5(13) . . . . ?
C9 C10 C12 C13 -169.4(9) . . . . ?
C11 C10 C12 C13 69.1(14) . . . . ?
C10 C12 C14 C15 -113.7(13) . . . . ?
C13 C12 C14 C15 121.3(13) . . . . ?
N6 C5 C16 C17 51.3(11) . . . . ?
C4 C5 C16 C17 -61.1(10) . . . . ?
N6 C5 C16 C21 -132.4(7) . . . . ?
C4 C5 C16 C21 115.2(9) . . . . ?
C21 C16 C17 C18 -0.5(12) . . . . ?
C5 C16 C17 C18 175.9(8) . . . . ?
C16 C17 C18 C19 2.2(13) . . . . ?
C17 C18 C19 C20 -1.7(12) . . . . ?
C18 C19 C20 C21 -0.4(12) . . . . ?
C19 C20 C21 C16 2.2(13) . . . . ?
C17 C16 C21 C20 -1.7(12) . . . . ?
C5 C16 C21 C20 -178.3(8) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653089
