#------------------------------------------------------------------------------
#$Date: 2019-11-11 16:55:53 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226629 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/51/4035149.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_4035149
loop_
_publ_author_name
'Banik, Ananya'
'Paira, Rupankar'
'Shaw, Bikash Kumar'
'Vijaykumar, Gonela'
'Mandal, Swadhin K.'
_publ_section_title
;
 Accessing Heterobiaryls through Transition-Metal-Free C-H
 Functionalization.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3236
_journal_page_last               3244
_journal_paper_doi               10.1021/acs.joc.8b00140
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C14 H10 N O'
_chemical_formula_sum            'C14 H10 N O'
_chemical_formula_weight         208.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.85(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.181(6)
_cell_length_b                   4.4360(11)
_cell_length_c                   15.689(4)
_cell_measurement_reflns_used    770
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.1570
_cell_measurement_theta_min      2.6010
_cell_volume                     1052.4(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.7799
_diffrn_measured_fraction_theta_max 0.7799
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -14.00  63.00   1.00  140.47    --   28.08 -99.00  30.00   77
  2  ω     68.00 108.00   1.00  140.47    --   28.08 178.00 -60.00   40
  3  ω    -25.00  82.00   1.00  140.47    --   28.08 -19.00  30.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0411745000
_diffrn_orient_matrix_UB_12      0.0729085000
_diffrn_orient_matrix_UB_13      -0.0097173000
_diffrn_orient_matrix_UB_21      0.0213115000
_diffrn_orient_matrix_UB_22      0.1427500000
_diffrn_orient_matrix_UB_23      0.0053560000
_diffrn_orient_matrix_UB_31      -0.0062211000
_diffrn_orient_matrix_UB_32      0.0016379000
_diffrn_orient_matrix_UB_33      -0.0472063000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1076
_diffrn_reflns_av_unetI/netI     0.1687
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3256
_diffrn_reflns_theta_full        28.3037
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.62
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3142
_exptl_crystal_description       needle
_exptl_crystal_F_000             436.1959
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.6143
_refine_diff_density_min         -0.7675
_refine_diff_density_rms         0.1670
_refine_ls_d_res_high            0.7495
_refine_ls_d_res_low             7.7708
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.7747
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     74
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.7747
_refine_ls_R_factor_all          0.1802
_refine_ls_R_factor_gt           0.0887
_refine_ls_shift/su_max          0.0066
_refine_ls_shift/su_mean         0.0019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.3376
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -20
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                759
_reflns_number_total             2034
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b00140_si_002.cif
_cod_data_source_block           Ligand1
_cod_database_code               4035149
_chemical_oxdiff_formula         'C H N'
_reflns_odcompleteness_completeness 96.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11) = Uanis(C10) = Uanis(C9) = Uanis(C8) = Uanis(C7) = Uanis(C6) =
Uanis(C5) = Uanis(C13) = Uanis(C4) = Uanis(C12) = Uanis(C3) = Uanis(C2) =
Uanis(C1)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C6(H6), C3(H3), C7(H7), C5(H5), C10(H10), C2(H2)
;
_olex2_date_sample_data_collection 2016-02-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.180
_oxdiff_exptl_absorpt_empirical_full_min 0.271
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
O1 O 0.84444(19) 0.5645(8) 0.25677(17) 0.0309(8) Uani 1.000000 .
N1 N 0.8961(2) 0.8857(8) 0.4049(2) 0.0280(9) Uani 1.000000 .
H1 H 0.9004(2) 0.8380(8) 0.3535(2) 0.0336(10) Uiso 1.000000 R
C1 C 0.8296(3) 0.7693(10) 0.4240(2) 0.0267(5) Uani 1.000000 .
C12 C 0.7698(3) 0.5616(10) 0.3627(2) 0.0267(5) Uani 1.000000 .
C8 C 0.6390(3) 0.2370(10) 0.3253(3) 0.0267(5) Uani 1.000000 .
C4 C 0.6830(3) 0.5362(10) 0.4639(2) 0.0267(5) Uani 1.000000 .
C9 C 0.6536(3) 0.1424(10) 0.2437(2) 0.0267(5) Uani 1.000000 .
H9 H 0.6156(3) 0.0028(10) 0.2050(2) 0.0321(6) Uiso 1.000000 R
C11 C 0.7830(3) 0.4658(10) 0.2797(2) 0.0267(5) Uani 1.000000 .
C6 C 0.5532(3) 0.2192(10) 0.4235(2) 0.0267(5) Uani 1.000000 .
H6 H 0.5051(3) 0.1463(10) 0.4364(2) 0.0321(6) Uiso 1.000000 R
C13 C 0.6980(3) 0.4458(10) 0.3842(2) 0.0267(5) Uani 1.000000 .
C14 C 0.9620(3) 1.0855(10) 0.4631(2) 0.0302(10) Uani 1.000000 .
H14a H 0.9867(3) 1.2049(10) 0.4262(2) 0.0362(12) Uiso 1.000000 R
H14b H 0.9342(3) 1.2226(10) 0.4930(2) 0.0362(12) Uiso 1.000000 R
C3 C 0.7452(3) 0.7390(10) 0.5241(2) 0.0267(5) Uani 1.000000 .
H3 H 0.7371(3) 0.7990(10) 0.5774(2) 0.0321(6) Uiso 1.000000 R
C7 C 0.5674(3) 0.1261(10) 0.3459(2) 0.0267(5) Uani 1.000000 .
H7 H 0.5290(3) -0.0119(10) 0.3069(2) 0.0321(6) Uiso 1.000000 R
C5 C 0.6109(3) 0.4208(10) 0.4817(2) 0.0267(5) Uani 1.000000 .
H5 H 0.6014(3) 0.4812(10) 0.5342(2) 0.0321(6) Uiso 1.000000 R
C10 C 0.7217(3) 0.2544(10) 0.2230(3) 0.0267(5) Uani 1.000000 .
H10 H 0.7289(3) 0.1908(10) 0.1696(3) 0.0321(6) Uiso 1.000000 R
C2 C 0.8156(3) 0.8472(10) 0.5061(2) 0.0267(5) Uani 1.000000 .
H2 H 0.8555(3) 0.9743(10) 0.5480(2) 0.0321(6) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C14 N1 C1 125.3(3) .
C12 C1 N1 120.7(3) .
C2 C1 N1 120.9(4) .
C2 C1 C12 118.4(4) .
C11 C12 C1 120.7(4) .
C13 C12 C1 119.2(3) .
C13 C12 C11 120.1(4) .
C13 C8 C9 119.0(4) .
C7 C8 C9 120.9(4) .
C7 C8 C13 120.1(3) .
C3 C4 C13 117.4(4) .
C5 C4 C13 119.6(4) .
C5 C4 C3 123.0(3) .
C10 C9 C8 120.8(4) .
C12 C11 O1 122.7(4) .
C10 C11 O1 120.0(3) .
C10 C11 C12 117.4(4) .
C5 C6 C7 119.5(4) .
C8 C13 C12 120.1(3) .
C4 C13 C12 121.4(4) .
C4 C13 C8 118.4(4) .
C14 C14 N1 112.6(4) 3_776
C2 C3 C4 122.2(3) .
C6 C7 C8 120.7(4) .
C6 C5 C4 121.7(4) .
C11 C10 C9 122.6(4) .
C3 C2 C1 121.1(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.250(5) .
N1 C1 1.321(5) .
N1 C14 1.436(5) .
C1 C12 1.431(6) .
C1 C2 1.428(5) .
C12 C11 1.456(5) .
C12 C13 1.418(6) .
C8 C9 1.444(5) .
C8 C13 1.412(6) .
C8 C7 1.398(6) .
C4 C13 1.414(5) .
C4 C3 1.427(6) .
C4 C5 1.390(6) .
C9 C10 1.351(6) .
C11 C10 1.423(6) .
C6 C7 1.381(5) .
C6 C5 1.378(6) .
C14 C14 1.553(8) 3_776
C3 C2 1.355(6) .
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.000 -0.546 0.250 59.7 19.6
2 0.000 -0.766 0.750 59.7 19.6
