#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/23/4022360.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_4022360
loop_
_publ_author_name
'Jason E. Field'
'Thomas J. Hill'
'D. Venkataraman'
_publ_contact_author_address
;
Department of Chemistry
University of Massachusetts
Amherst, MA 01003
;
_publ_contact_author_email       dv@chem.umass.edu
_publ_contact_author_fax         413-545-4490
_publ_contact_author_name        'D. Venkataraman'
_publ_contact_author_phone       413-545-2028
_publ_section_title
;
 Bridged Triarylamines: A New Class of Heterohelicenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6071
_journal_page_last               6078
_journal_paper_doi               10.1021/jo026883p
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C32 H23 N O2 '
_chemical_formula_sum            'C32 H23 N O2'
_chemical_formula_weight         453.541
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 128.574(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.986(2)
_cell_length_b                   13.832(2)
_cell_length_c                   11.967(2)
_cell_measurement_reflns_used    1191
_cell_measurement_theta_max      20.600
_cell_measurement_theta_min      4.076
_cell_volume                     2327.7(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.01801
_diffrn_orient_matrix_UB_12      0.01926
_diffrn_orient_matrix_UB_13      -0.06605
_diffrn_orient_matrix_UB_21      -0.05197
_diffrn_orient_matrix_UB_22      -0.04264
_diffrn_orient_matrix_UB_23      -0.02660
_diffrn_orient_matrix_UB_31      -0.03722
_diffrn_orient_matrix_UB_32      0.08163
_diffrn_orient_matrix_UB_33      -0.05810
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2151
_diffrn_reflns_theta_full        20.55
_diffrn_reflns_theta_max         20.55
_diffrn_reflns_theta_min         4.13
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1156
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.273
_refine_ls_R_factor_all          0.1827
_refine_ls_R_factor_gt           0.1242
_refine_ls_shift/su_max          0.846
_refine_ls_shift/su_mean         0.122
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3322
_refine_ls_wR_factor_ref         0.3715
_reflns_number_gt                696
_reflns_number_total             1156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026883psi20021219_022332_3.cif
_cod_data_source_block           comp3
_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      'C 2/c         '
_cod_original_formula_sum        'C32 H23 N O2 '
_cod_database_code               4022360
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'
'-X,+Y,-Z+ 1/2'
'+X,-Y,+Z+ 1/2'
'+X+ 1/2,-Y+ 1/2,+Z+ 1/2'
'-X+ 1/2,+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.3536(5) 0.0662(5) 0.3546(8) 0.089(2) Uani 1 1 d .
N1 N 0.5000 0.2019(8) 0.2500 0.062(3) Uani 1 2 d S
C1 C 0.5000 -0.1008(11) 0.2500 0.077(4) Uani 1 2 d S
C2 C 0.4499(7) -0.0510(7) 0.2804(9) 0.072(3) Uani 1 1 d .
C3 C 0.4464(7) 0.0490(8) 0.2776(9) 0.070(3) Uani 1 1 d .
C4 C 0.5000 0.0992(10) 0.2500 0.063(4) Uani 1 2 d S
C5 C 0.3865(8) 0.1055(8) 0.2992(10) 0.074(3) Uani 1 1 d .
C6 C 0.3650(7) 0.2049(7) 0.2497(9) 0.062(3) Uani 1 1 d .
C7 C 0.4198(7) 0.2506(7) 0.2170(9) 0.062(3) Uani 1 1 d .
C8 C 0.3842(6) 0.3383(6) 0.1381(9) 0.055(2) Uani 1 1 d .
C9 C 0.4182(7) 0.3779(8) 0.0662(10) 0.080(3) Uani 1 1 d .
C10 C 0.3841(8) 0.4637(8) -0.0050(11) 0.082(3) Uani 1 1 d .
C11 C 0.3180(9) 0.5123(8) -0.0111(12) 0.089(4) Uani 1 1 d .
C12 C 0.2811(7) 0.4775(8) 0.0501(12) 0.084(3) Uani 1 1 d .
C13 C 0.3141(7) 0.3886(7) 0.1249(10) 0.065(3) Uani 1 1 d .
C14 C 0.2676(8) 0.3467(9) 0.1712(11) 0.091(4) Uani 1 1 d .
C15 C 0.2896(7) 0.2564(10) 0.2304(10) 0.083(3) Uani 1 1 d .
C16 C 0.5000 -0.2089(14) 0.2500 0.122(7) Uani 1 2 d SD
C17 C 0.5119(19) -0.2584(10) 0.154(2) 0.221(11) Uani 1 1 d D
C18 C 0.5994(11) -0.2404(17) 0.357(3) 0.179(15) Uani 0.50 1 d PD
H2 H 0.4168 -0.0850 0.3040 0.086 Uiso 1 1 d R
H9 H 0.4635 0.3445 0.0673 0.096 Uiso 1 1 d R
H10 H 0.4059 0.4887 -0.0520 0.098 Uiso 1 1 d R
H11 H 0.2965 0.5718 -0.0574 0.107 Uiso 1 1 d R
H12 H 0.2348 0.5120 0.0452 0.101 Uiso 1 1 d R
H14 H 0.2195 0.3802 0.1630 0.109 Uiso 1 1 d R
H15 H 0.2567 0.2280 0.2583 0.099 Uiso 1 1 d R
H17A H 0.5107 -0.3271 0.1646 0.332 Uiso 1 1 calc R
H17B H 0.5717 -0.2402 0.1775 0.332 Uiso 1 1 calc R
H17C H 0.4611 -0.2404 0.0570 0.332 Uiso 1 1 calc R
H18A H 0.6021 -0.3098 0.3603 0.269 Uiso 0.50 1 calc PR
H18B H 0.6236 -0.2160 0.4497 0.269 Uiso 0.50 1 calc PR
H18C H 0.6372 -0.2160 0.3323 0.269 Uiso 0.50 1 calc PR
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_
_diffrn_radiation_wavelength
0.71073
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
C7 N1 C7 122.8(12) 2_655 .
C7 N1 C4 118.6(6) 2_655 .
C7 N1 C4 118.6(6) . .
C2 C1 C2 118.8(14) . 2_655
C2 C1 C16 120.6(7) . .
C2 C1 C16 120.6(7) 2_655 .
C1 C2 C3 122.0(11) . .
C4 C3 C2 118.6(11) . .
C4 C3 C5 117.9(9) . .
C2 C3 C5 123.5(9) . .
C3 C4 C3 119.8(13) 2_655 .
C3 C4 N1 120.1(7) 2_655 .
C3 C4 N1 120.1(7) . .
O1 C5 C6 122.2(11) . .
O1 C5 C3 119.9(10) . .
C6 C5 C3 117.9(9) . .
C7 C6 C15 119.3(9) . .
C7 C6 C5 118.8(10) . .
C15 C6 C5 121.8(11) . .
N1 C7 C6 118.4(8) . .
N1 C7 C8 123.6(10) . .
C6 C7 C8 117.5(9) . .
C13 C8 C7 121.1(9) . .
C13 C8 C9 116.3(9) . .
C7 C8 C9 122.6(9) . .
C10 C9 C8 120.8(10) . .
C11 C10 C9 120.9(12) . .
C12 C11 C10 121.1(11) . .
C11 C12 C13 120.0(11) . .
C8 C13 C14 119.1(10) . .
C8 C13 C12 120.8(10) . .
C14 C13 C12 119.7(11) . .
C15 C14 C13 122.4(11) . .
C14 C15 C6 118.9(10) . .
C1 C16 C17 117.9(9) . .
C1 C16 C17 117.9(9) . 2_655
C17 C16 C17 124.2(18) . 2_655
C1 C16 C18 107.2(12) . 2_655
C17 C16 C18 82.5(14) . 2_655
C17 C16 C18 81.7(16) 2_655 2_655
C1 C16 C18 107.2(12) . .
C17 C16 C18 81.7(16) . .
C17 C16 C18 82.5(14) 2_655 .
C18 C16 C18 146(2) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.255(10) .
N1 C7 1.407(10) 2_655
N1 C7 1.407(10) .
N1 C4 1.420(15) .
C1 C2 1.352(11) .
C1 C2 1.352(11) 2_655
C1 C16 1.50(2) .
C2 C3 1.385(13) .
C3 C4 1.385(10) .
C3 C5 1.477(13) .
C4 C3 1.385(10) 2_655
C5 C6 1.450(13) .
C6 C7 1.417(12) .
C6 C15 1.417(12) .
C7 C8 1.420(12) .
C8 C13 1.360(12) .
C8 C9 1.439(13) .
C9 C10 1.364(13) .
C10 C11 1.327(13) .
C11 C12 1.348(14) .
C12 C13 1.414(13) .
C13 C14 1.388(14) .
C14 C15 1.367(15) .
C16 C17 1.463(13) .
C16 C17 1.463(13) 2_655
C16 C18 1.474(14) 2_655
C16 C18 1.474(14) .
