#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/65/1516529.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_1516529
loop_
_publ_author_name
'Patel, Pitambar'
'Chang, Sukbok'
_publ_section_title
;
 N-substituted hydroxylamines as synthetically versatile amino sources in
 the iridium-catalyzed mild C-h amidation reaction.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3328
_journal_page_last               3331
_journal_paper_doi               10.1021/ol501338h
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C20 H20 N2 O2'
_chemical_formula_sum            'C20 H20 N2 O2'
_chemical_formula_weight         320.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.3970(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5080(4)
_cell_length_b                   10.4245(4)
_cell_length_c                   17.1939(7)
_cell_measurement_reflns_used    21326
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.29
_cell_volume                     1685.92(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21326
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.5473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                3161
_reflns_number_total             3436
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501338h_si_003.cif
_cod_data_source_block           0122b-1
_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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516527--1516529.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1516529
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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 0.55381(8) 0.30298(8) 0.48115(4) 0.0239(2) Uani 1 1 d U
O2 O 0.73790(9) 0.17673(9) 0.53528(5) 0.0301(2) Uani 1 1 d U
N2 N 0.80086(10) 0.48049(9) 0.30001(5) 0.0244(2) Uani 1 1 d U
N1 N 0.74061(10) 0.28444(9) 0.41946(6) 0.0240(2) Uani 1 1 d U
H1B H 0.6934 0.3401 0.3871 0.029 Uiso 1 1 calc R
C15 C 0.87209(12) 0.23928(11) 0.40116(6) 0.0207(2) Uani 1 1 d U
C16 C 0.68162(12) 0.24750(11) 0.48398(6) 0.0221(2) Uani 1 1 d U
C7 C 1.08916(12) 0.27204(10) 0.34388(6) 0.0203(2) Uani 1 1 d U
C5 C 0.92051(12) 0.45780(10) 0.35018(6) 0.0202(2) Uani 1 1 d U
C12 C 1.12848(12) 0.14223(11) 0.36157(6) 0.0220(2) Uani 1 1 d U
C6 C 0.95946(12) 0.32046(10) 0.36596(6) 0.0197(2) Uani 1 1 d U
C13 C 1.03636(13) 0.06355(11) 0.39842(6) 0.0242(3) Uani 1 1 d U
H13A H 1.0622 -0.0230 0.4104 0.029 Uiso 1 1 calc R
C14 C 0.91134(12) 0.10956(11) 0.41711(7) 0.0237(2) Uani 1 1 d U
H14A H 0.8503 0.0546 0.4409 0.028 Uiso 1 1 calc R
C11 C 1.25918(13) 0.09469(12) 0.34291(7) 0.0266(3) Uani 1 1 d U
H11A H 1.2850 0.0080 0.3545 0.032 Uiso 1 1 calc R
C1 C 0.76935(13) 0.60341(12) 0.28149(7) 0.0282(3) Uani 1 1 d U
H1A H 0.6853 0.6205 0.2459 0.034 Uiso 1 1 calc R
C4 C 1.00656(12) 0.55628(11) 0.38510(7) 0.0257(3) Uani 1 1 d U
H4A H 1.0881 0.5374 0.4222 0.031 Uiso 1 1 calc R
C8 C 1.18292(13) 0.34803(11) 0.30553(7) 0.0246(3) Uani 1 1 d U
H8A H 1.1576 0.4339 0.2912 0.030 Uiso 1 1 calc R
C17 C 0.47254(12) 0.29046(11) 0.54823(6) 0.0237(3) Uani 1 1 d U
C10 C 1.34849(13) 0.17176(13) 0.30850(7) 0.0299(3) Uani 1 1 d U
H10A H 1.4371 0.1395 0.2977 0.036 Uiso 1 1 calc R
C9 C 1.30877(13) 0.29925(12) 0.28902(7) 0.0292(3) Uani 1 1 d U
H9A H 1.3703 0.3521 0.2641 0.035 Uiso 1 1 calc R
C3 C 0.97154(14) 0.68231(12) 0.36493(8) 0.0304(3) Uani 1 1 d U
H3A H 1.0290 0.7510 0.3878 0.037 Uiso 1 1 calc R
C2 C 0.85179(14) 0.70657(11) 0.31107(7) 0.0300(3) Uani 1 1 d U
H2A H 0.8268 0.7917 0.2948 0.036 Uiso 1 1 calc R
C19 C 0.34061(12) 0.36939(12) 0.51998(7) 0.0284(3) Uani 1 1 d U
H19A H 0.2878 0.3295 0.4730 0.043 Uiso 1 1 calc R
H19B H 0.3687 0.4565 0.5073 0.043 Uiso 1 1 calc R
H19C H 0.2802 0.3731 0.5615 0.043 Uiso 1 1 calc R
C18 C 0.55726(14) 0.34906(15) 0.62146(7) 0.0343(3) Uani 1 1 d U
H18A H 0.5801 0.4385 0.6109 0.051 Uiso 1 1 calc R
H18B H 0.6455 0.3005 0.6359 0.051 Uiso 1 1 calc R
H18C H 0.5008 0.3460 0.6648 0.051 Uiso 1 1 calc R
C20 C 0.43268(14) 0.15104(13) 0.55925(8) 0.0336(3) Uani 1 1 d U
H20A H 0.3789 0.1184 0.5103 0.050 Uiso 1 1 calc R
H20B H 0.3741 0.1449 0.6015 0.050 Uiso 1 1 calc R
H20C H 0.5193 0.1000 0.5730 0.050 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
C16 O1 C17 120.39(8)
C1 N2 C5 117.28(10)
C16 N1 C15 124.52(9)
C6 C15 N1 120.00(10)
C6 C15 C14 120.60(10)
N1 C15 C14 119.38(10)
O2 C16 O1 126.18(10)
O2 C16 N1 124.81(10)
O1 C16 N1 109.01(9)
C8 C7 C12 117.68(10)
C8 C7 C6 123.19(10)
C12 C7 C6 119.13(10)
N2 C5 C4 122.38(10)
N2 C5 C6 116.70(10)
C4 C5 C6 120.91(10)
C13 C12 C11 121.26(10)
C13 C12 C7 119.06(10)
C11 C12 C7 119.67(10)
C15 C6 C7 119.63(10)
C15 C6 C5 121.07(10)
C7 C6 C5 119.30(9)
C14 C13 C12 121.30(10)
C13 C14 C15 120.24(10)
C10 C11 C12 120.91(11)
N2 C1 C2 124.03(11)
C3 C4 C5 119.08(11)
C9 C8 C7 121.00(11)
O1 C17 C19 101.72(9)
O1 C17 C18 109.57(9)
C19 C17 C18 111.10(10)
O1 C17 C20 110.38(9)
C19 C17 C20 110.38(10)
C18 C17 C20 113.10(11)
C11 C10 C9 119.75(11)
C8 C9 C10 120.92(11)
C2 C3 C4 119.02(11)
C3 C2 C1 118.12(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C16 1.3403(13)
O1 C17 1.4848(13)
O2 C16 1.2127(14)
N2 C1 1.3436(15)
N2 C5 1.3445(15)
N1 C16 1.3695(14)
N1 C15 1.4136(14)
C15 C6 1.3855(15)
C15 C14 1.4189(15)
C7 C8 1.4243(16)
C7 C12 1.4249(15)
C7 C6 1.4339(15)
C5 C4 1.3930(16)
C5 C6 1.4937(15)
C12 C13 1.4154(16)
C12 C11 1.4175(16)
C13 C14 1.3630(16)
C11 C10 1.3651(18)
C1 C2 1.3832(19)
C4 C3 1.3869(17)
C8 C9 1.3675(17)
C17 C19 1.5193(16)
C17 C18 1.5203(17)
C17 C20 1.5208(17)
C10 C9 1.4086(18)
C3 C2 1.3821(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139043596
