#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:56:18 +0100 (lun 21 de mar de 2016) $
#$Revision: 178412 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/33/4023313.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_4023313
loop_
_publ_author_name
'Adam W. Franz'
'Frank Rominger'
'Thomas J. J. Müller'
_publ_contact_author_address
;
        Institut für Makromolekulare Chemie und Organische Chemie
        Heinrich-Heine-Universität Düsseldorf
        Universitätsstrasse 1
        D-40225 Düsseldorf
        Germany
;
_publ_contact_author_email       ThomasJJ.Mueller@uni-duesseldorf.de
_publ_contact_author_fax         '+49 211 - 8114324'
_publ_contact_author_name        'Müller, Thomas J.J.'
_publ_contact_author_phone       '+49 211 - 8112298'
_publ_section_title
;
 Synthesis and Electronic Properties of Sterically Demanding
 N-Arylphenothiazines and Unexpected Buchwald-Hartwig Aminations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1795
_journal_page_last               1802
_journal_paper_doi               10.1021/jo702389v
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H24 O2'
_chemical_formula_weight         320.41
_chemical_name_systematic
;
 ?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.220(2)
_cell_angle_beta                 104.065(2)
_cell_angle_gamma                102.182(2)
_cell_formula_units_Z            1
_cell_length_a                   6.1109(5)
_cell_length_b                   8.1002(7)
_cell_length_c                   9.9882(8)
_cell_measurement_temperature    200(2)
_cell_volume                     436.21(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0842
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4580
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pale_yellow
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.062(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0441P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                1088
_reflns_number_total             1986
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702389v-File001_3.cif
_cod_data_source_block           afr4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4023313
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
C1 C 0.4196(2) 0.66154(18) 0.51631(15) 0.0271(4) Uani 1 1 d . . .
O1 O 0.35421(18) 0.79616(14) 0.53137(12) 0.0398(3) Uani 1 1 d . . .
C2 C 0.3611(2) 0.53995(18) 0.59706(15) 0.0254(4) Uani 1 1 d . . .
C3 C 0.2234(3) 0.57629(19) 0.68728(16) 0.0322(4) Uani 1 1 d . . .
H3 H 0.1689 0.6795 0.6979 0.039 Uiso 1 1 calc R . .
C4 C 0.1646(3) 0.46373(19) 0.76193(16) 0.0330(4) Uani 1 1 d . . .
H4 H 0.0699 0.4915 0.8230 0.040 Uiso 1 1 calc R . .
C5 C 0.2397(2) 0.31104(18) 0.75041(15) 0.0258(4) Uani 1 1 d . . .
C6 C 0.3766(2) 0.27533(18) 0.65893(15) 0.0271(4) Uani 1 1 d . . .
H6 H 0.4299 0.1716 0.6482 0.033 Uiso 1 1 calc R . .
C7 C 0.4381(2) 0.38640(18) 0.58255(14) 0.0239(3) Uani 1 1 d . . .
C11 C 0.1663(2) 0.18131(19) 0.82775(15) 0.0280(4) Uani 1 1 d . . .
C12 C 0.0807(3) 0.2706(2) 0.95435(18) 0.0491(5) Uani 1 1 d . . .
H12A H 0.2056 0.3811 1.0256 0.074 Uiso 1 1 calc R . .
H12B H 0.0430 0.1862 1.0043 0.074 Uiso 1 1 calc R . .
H12C H -0.0613 0.3018 0.9144 0.074 Uiso 1 1 calc R . .
C13 C -0.0355(3) 0.0158(2) 0.71141(17) 0.0414(5) Uani 1 1 d . . .
H13A H -0.1680 0.0555 0.6692 0.062 Uiso 1 1 calc R . .
H13B H -0.0885 -0.0685 0.7583 0.062 Uiso 1 1 calc R . .
H13C H 0.0211 -0.0452 0.6324 0.062 Uiso 1 1 calc R . .
C14 C 0.3728(3) 0.1188(2) 0.89197(17) 0.0409(4) Uani 1 1 d . . .
H14A H 0.4230 0.0528 0.8116 0.061 Uiso 1 1 calc R . .
H14B H 0.3226 0.0389 0.9430 0.061 Uiso 1 1 calc R . .
H14C H 0.5053 0.2248 0.9626 0.061 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0287(9) 0.0230(8) 0.0311(9) 0.0106(7) 0.0111(7) 0.0085(7)
O1 0.0563(7) 0.0342(6) 0.0531(8) 0.0257(6) 0.0354(6) 0.0279(6)
C2 0.0275(8) 0.0220(8) 0.0272(9) 0.0095(7) 0.0107(7) 0.0057(7)
C3 0.0437(10) 0.0269(9) 0.0384(10) 0.0161(8) 0.0233(8) 0.0183(8)
C4 0.0396(10) 0.0331(9) 0.0365(10) 0.0149(8) 0.0233(8) 0.0159(8)
C5 0.0262(8) 0.0246(8) 0.0240(8) 0.0083(7) 0.0072(7) 0.0051(7)
C6 0.0319(9) 0.0232(8) 0.0292(9) 0.0107(7) 0.0113(7) 0.0110(7)
C7 0.0271(8) 0.0214(8) 0.0237(8) 0.0072(7) 0.0101(7) 0.0080(7)
C11 0.0312(8) 0.0284(8) 0.0289(9) 0.0138(7) 0.0138(7) 0.0087(7)
C12 0.0756(13) 0.0435(11) 0.0537(12) 0.0303(10) 0.0433(11) 0.0249(10)
C13 0.0383(9) 0.0389(10) 0.0477(11) 0.0250(8) 0.0100(8) 0.0045(8)
C14 0.0415(10) 0.0513(11) 0.0391(10) 0.0282(9) 0.0139(8) 0.0152(8)
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'
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 C1 C2 121.07(13) . . ?
O1 C1 C7 121.34(12) . 2_666 ?
C2 C1 C7 117.59(12) . 2_666 ?
C3 C2 C7 118.63(12) . . ?
C3 C2 C1 119.67(13) . . ?
C7 C2 C1 121.68(12) . . ?
C4 C3 C2 120.60(13) . . ?
C3 C4 C5 122.04(13) . . ?
C4 C5 C6 116.86(13) . . ?
C4 C5 C11 122.22(12) . . ?
C6 C5 C11 120.85(12) . . ?
C7 C6 C5 122.21(13) . . ?
C6 C7 C2 119.65(12) . . ?
C6 C7 C1 119.61(12) . 2_666 ?
C2 C7 C1 120.73(12) . 2_666 ?
C14 C11 C12 107.92(12) . . ?
C14 C11 C13 109.18(12) . . ?
C12 C11 C13 109.25(13) . . ?
C14 C11 C5 111.06(11) . . ?
C12 C11 C5 111.73(12) . . ?
C13 C11 C5 107.66(11) . . ?
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
C1 O1 1.2197(15) . ?
C1 C2 1.4866(19) . ?
C1 C7 1.4881(18) 2_666 ?
C2 C3 1.3868(18) . ?
C2 C7 1.4010(17) . ?
C3 C4 1.3824(19) . ?
C4 C5 1.3911(18) . ?
C5 C6 1.3913(18) . ?
C5 C11 1.5337(19) . ?
C6 C7 1.3913(18) . ?
C7 C1 1.4881(18) 2_666 ?
C11 C14 1.526(2) . ?
C11 C12 1.528(2) . ?
C11 C13 1.5332(19) . ?
