#------------------------------------------------------------------------------
#$Date: 2016-01-06 12:28:57 +0200 (Wed, 06 Jan 2016) $
#$Revision: 173595 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/17/4031749.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_4031749
loop_
_publ_author_name
'Bodapati, Ramakrishna'
'Sarma, Monima'
'Kanakati, Arunkumar'
'Das, Samar K.'
_publ_section_title
;
 Asymmetrically Substituted and π-Conjugated 2,2'-Bipyridine Derivatives:
 Synthesis, Spectroscopy, Computation, and Crystallography.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12482
_journal_page_last               12491
_journal_paper_doi               10.1021/acs.joc.5b02345
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C25 H27 N3 O2'
_chemical_formula_sum            'C25 H27 N3 O2'
_chemical_formula_weight         401.50
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.953(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5975(14)
_cell_length_b                   10.5316(19)
_cell_length_c                   27.162(5)
_cell_measurement_reflns_used    4781
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.23
_cell_measurement_theta_min      2.46
_cell_volume                     2152.4(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            22541
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorles
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0806
_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)+(0.0852P)²+1.3060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1929
_refine_ls_wR_factor_ref         0.2045
_reflns_number_gt                3603
_reflns_number_total             4436
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02345_si_001.cif
_cod_data_source_block           18
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4031749.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               4031749
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O2 O 0.1193(2) 0.66247(16) 0.02022(7) 0.0543(5) Uani 1 1 d .
C17 C 0.2605(3) 0.9931(2) 0.01000(8) 0.0418(5) Uani 1 1 d .
H17 H 0.2557 1.0580 -0.0133 0.050 Uiso 1 1 calc R
O1 O 0.4016(2) 1.13411(16) 0.07363(6) 0.0539(5) Uani 1 1 d .
C16 C 0.3344(3) 1.0178(2) 0.05827(8) 0.0406(5) Uani 1 1 d .
C15 C 0.2721(3) 0.8058(2) 0.08010(8) 0.0440(6) Uani 1 1 d .
H15 H 0.2754 0.7416 0.1037 0.053 Uiso 1 1 calc R
C18 C 0.1924(3) 0.8735(2) -0.00520(8) 0.0394(5) Uani 1 1 d .
N1 N 0.1213(3) 0.8539(2) -0.05413(7) 0.0476(5) Uani 1 1 d .
C19 C 0.1981(3) 0.7796(2) 0.03214(8) 0.0424(5) Uani 1 1 d .
C14 C 0.3427(3) 0.9244(2) 0.09509(8) 0.0403(5) Uani 1 1 d .
C13 C 0.4198(3) 0.9521(2) 0.14611(9) 0.0441(6) Uani 1 1 d .
H13 H 0.4978 1.0206 0.1505 0.053 Uiso 1 1 calc R
C3 C 0.9893(3) 1.0852(3) 0.34984(9) 0.0516(6) Uani 1 1 d .
H3 H 0.9515 1.0410 0.3761 0.062 Uiso 1 1 calc R
C7 C 0.6350(3) 0.9906(2) 0.24622(9) 0.0468(6) Uani 1 1 d .
H7 H 0.6808 1.0283 0.2197 0.056 Uiso 1 1 calc R
C25 C 0.1110(4) 0.9578(3) -0.08985(9) 0.0556(7) Uani 1 1 d .
H25A H 0.2282 0.9906 -0.0930 0.067 Uiso 1 1 calc R
H25B H 0.0375 1.0263 -0.0803 0.067 Uiso 1 1 calc R
C10 C 0.4827(4) 0.9176(3) 0.23711(9) 0.0518(6) Uani 1 1 d .
C4 C 0.8881(3) 1.0818(2) 0.30340(9) 0.0483(6) Uani 1 1 d .
C12 C 0.3919(3) 0.8913(3) 0.18693(9) 0.0507(6) Uani 1 1 d .
H12 H 0.3078 0.8266 0.1835 0.061 Uiso 1 1 calc R
C20 C 0.2327(4) 0.5562(3) 0.02972(12) 0.0662(8) Uani 1 1 d .
H20A H 0.3349 0.5668 0.0129 0.099 Uiso 1 1 calc R
H20B H 0.1700 0.4806 0.0179 0.099 Uiso 1 1 calc R
H20C H 0.2702 0.5490 0.0648 0.099 Uiso 1 1 calc R
N2 N 0.9355(4) 1.1437(3) 0.26467(9) 0.0836(9) Uani 1 1 d .
C6 C 0.7202(3) 1.0086(3) 0.29400(9) 0.0504(6) Uani 1 1 d .
C2 C 1.1445(4) 1.1532(3) 0.35755(10) 0.0636(8) Uani 1 1 d .
C24 C 0.0272(5) 0.8961(4) -0.13776(11) 0.0809(10) Uani 1 1 d .
H24A H -0.1014 0.8962 -0.1402 0.097 Uiso 1 1 calc R
H24B H 0.0618 0.9395 -0.1664 0.097 Uiso 1 1 calc R
N3 N 0.6600(4) 0.9592(4) 0.33366(9) 0.0968(12) Uani 1 1 d .
C21 C 0.3773(4) 1.2355(3) 0.03961(11) 0.0635(8) Uani 1 1 d .
H21A H 0.4430 1.2192 0.0125 0.095 Uiso 1 1 calc R
H21B H 0.4192 1.3127 0.0560 0.095 Uiso 1 1 calc R
H21C H 0.2534 1.2437 0.0271 0.095 Uiso 1 1 calc R
C9 C 0.4220(5) 0.8651(5) 0.27821(11) 0.1007(15) Uani 1 1 d .
H9 H 0.3213 0.8139 0.2746 0.121 Uiso 1 1 calc R
C22 C 0.1088(5) 0.7321(3) -0.07965(10) 0.0653(8) Uani 1 1 d .
H22A H 0.0039 0.6858 -0.0733 0.078 Uiso 1 1 calc R
H22B H 0.2132 0.6806 -0.0693 0.078 Uiso 1 1 calc R
C11 C 1.2556(5) 1.1600(4) 0.40778(13) 0.0945(13) Uani 1 1 d .
H11A H 1.3286 1.0855 0.4129 0.142 Uiso 1 1 calc R
H11B H 1.1793 1.1648 0.4331 0.142 Uiso 1 1 calc R
H11C H 1.3299 1.2341 0.4094 0.142 Uiso 1 1 calc R
C1 C 1.1934(5) 1.2156(5) 0.31766(13) 0.1124(17) Uani 1 1 d .
H1 H 1.2979 1.2627 0.3208 0.135 Uiso 1 1 calc R
C5 C 1.0859(6) 1.2080(5) 0.27254(13) 0.129(2) Uani 1 1 d .
H5 H 1.1217 1.2513 0.2458 0.155 Uiso 1 1 calc R
C23 C 0.0965(7) 0.7682(4) -0.13403(12) 0.1004(14) Uani 1 1 d .
H23A H 0.2128 0.7648 -0.1449 0.121 Uiso 1 1 calc R
H23B H 0.0176 0.7107 -0.1544 0.121 Uiso 1 1 calc R
C8 C 0.5136(6) 0.8899(6) 0.32466(12) 0.137(2) Uani 1 1 d .
H8 H 0.4689 0.8553 0.3519 0.165 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
C19 O2 C20 115.33(19)
C16 C17 C18 122.4(2)
C16 O1 C21 117.97(19)
O1 C16 C17 123.0(2)
O1 C16 C14 115.69(19)
C17 C16 C14 121.3(2)
C19 C15 C14 123.1(2)
N1 C18 C17 119.9(2)
N1 C18 C19 123.8(2)
C17 C18 C19 116.3(2)
C18 N1 C22 125.6(2)
C18 N1 C25 120.5(2)
C22 N1 C25 110.5(2)
C15 C19 O2 120.4(2)
C15 C19 C18 120.5(2)
O2 C19 C18 119.0(2)
C15 C14 C16 116.3(2)
C15 C14 C13 123.0(2)
C16 C14 C13 120.7(2)
C12 C13 C14 127.6(2)
C2 C3 C4 120.7(2)
C6 C7 C10 121.1(2)
N1 C25 C24 103.2(2)
C9 C10 C7 116.3(2)
C9 C10 C12 120.6(2)
C7 C10 C12 123.1(2)
N2 C4 C3 122.1(2)
N2 C4 C6 116.1(2)
C3 C4 C6 121.8(2)
C13 C12 C10 125.3(2)
C5 N2 C4 116.5(2)
N3 C6 C7 122.5(2)
N3 C6 C4 116.6(2)
C7 C6 C4 120.9(2)
C1 C2 C3 117.0(3)
C1 C2 C11 121.2(3)
C3 C2 C11 121.8(3)
C23 C24 C25 103.5(3)
C8 N3 C6 116.1(2)
C8 C9 C10 118.8(3)
N1 C22 C23 103.6(3)
C2 C1 C5 119.1(3)
N2 C5 C1 124.5(3)
C24 C23 C22 105.9(3)
N3 C8 C9 125.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C19 1.390(3)
O2 C20 1.415(3)
C17 C16 1.378(3)
C17 C18 1.402(3)
O1 C16 1.370(3)
O1 C21 1.407(3)
C16 C14 1.398(3)
C15 C19 1.374(3)
C15 C14 1.397(3)
C18 N1 1.379(3)
C18 C19 1.413(3)
N1 C22 1.455(3)
N1 C25 1.457(3)
C14 C13 1.458(3)
C13 C12 1.323(3)
C3 C2 1.371(4)
C3 C4 1.384(3)
C7 C6 1.381(3)
C7 C10 1.383(4)
C25 C24 1.513(4)
C10 C9 1.381(4)
C10 C12 1.466(3)
C4 N2 1.329(3)
C4 C6 1.482(4)
N2 C5 1.320(4)
C6 N3 1.333(3)
C2 C1 1.362(5)
C2 C11 1.504(4)
C24 C23 1.445(5)
N3 C8 1.324(4)
C9 C8 1.379(4)
C22 C23 1.515(4)
C1 C5 1.378(5)
