#------------------------------------------------------------------------------
#$Date: 2019-11-11 18:52:43 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226949 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/55/4035501.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_4035501
loop_
_publ_author_name
'Bulut, Safak'
'Queen, Wendy L.'
_publ_section_title
;
 Catalyst-Free Synthesis of Aryl Diamines via a Three-Step Reaction
 Process.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3806
_journal_page_last               3818
_journal_paper_doi               10.1021/acs.joc.8b00151
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_name_common            'CCDC 1540292_Compound 6_SB97d_2_0m'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.552(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0825(12)
_cell_length_b                   10.495(3)
_cell_length_c                   13.156(3)
_cell_measurement_reflns_used    2542
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      48.560
_cell_measurement_theta_min      4.999
_cell_volume                     689.9(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  Venture
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10854
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.749
_diffrn_reflns_theta_max         24.749
_diffrn_reflns_theta_min         2.499
_exptl_absorpt_coefficient_mu    0.105
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0744
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1293P)²+0.8606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1963
_refine_ls_wR_factor_ref         0.2159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                984
_reflns_number_total             1211
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00151_si_002.cif
_cod_data_source_block           sb97d_2_0m
_cod_database_code               4035501
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.743(4) 0.257(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
3.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C005(H005), C006(H006), C008(H008), C00B(H00C)
3.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O001 O -0.2263(7) 0.4282(3) 0.0502(2) 0.0213(8) Uani 1 1 d .
O002 O -0.3282(7) 0.6323(3) 0.0751(2) 0.0254(9) Uani 1 1 d .
H002 H -0.4715 0.6117 0.0359 0.038 Uiso 1 1 calc GR
N003 N 0.7014(8) 0.5781(4) 0.4251(2) 0.0219(9) Uani 1 1 d .
H003 H 0.7173 0.6489 0.4615 0.026 Uiso 1 1 calc R
C004 C -0.1743(10) 0.5303(4) 0.0961(3) 0.0202(11) Uani 1 1 d .
C005 C 0.0965(10) 0.6571(4) 0.2393(3) 0.0205(10) Uani 1 1 d .
H005 H -0.0266 0.7256 0.2245 0.025 Uiso 1 1 calc R
C006 C 0.4561(9) 0.4559(4) 0.2818(3) 0.0200(11) Uani 1 1 d .
H006 H 0.5786 0.3870 0.2963 0.024 Uiso 1 1 calc R
C007 C 0.0591(10) 0.5468(4) 0.1785(3) 0.0192(10) Uani 1 1 d .
C008 C 0.3093(9) 0.6673(4) 0.3201(3) 0.0202(10) Uani 1 1 d .
H008 H 0.3317 0.7429 0.3606 0.024 Uiso 1 1 calc R
C009 C 0.4938(9) 0.5672(4) 0.3435(3) 0.0188(10) Uani 1 1 d .
C00A C 0.8973(10) 0.4776(4) 0.4544(3) 0.0224(11) Uani 1 1 d .
H00A H 0.9864 0.4570 0.3955 0.027 Uiso 1 1 calc R
H00B H 0.8074 0.3997 0.4733 0.027 Uiso 1 1 calc R
C00B C 0.2431(10) 0.4472(4) 0.2012(3) 0.0201(10) Uani 1 1 d .
H00C H 0.2204 0.3721 0.1601 0.024 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C004 O002 H002 109.5 . .
C009 N003 H003 118.6 . .
C009 N003 C00A 122.8(4) . .
C00A N003 H003 118.6 . .
O001 C004 O002 122.3(4) . .
O001 C004 C007 122.5(4) . .
O002 C004 C007 115.2(4) . .
C007 C005 H005 119.6 . .
C008 C005 H005 119.6 . .
C008 C005 C007 120.8(4) . .
C009 C006 H006 119.9 . .
C00B C006 H006 119.9 . .
C00B C006 C009 120.2(4) . .
C005 C007 C004 121.9(4) . .
C00B C007 C004 119.3(4) . .
C00B C007 C005 118.8(4) . .
C005 C008 H008 119.7 . .
C005 C008 C009 120.7(4) . .
C009 C008 H008 119.7 . .
N003 C009 C006 121.6(4) . .
N003 C009 C008 119.9(4) . .
C008 C009 C006 118.5(4) . .
N003 C00A C00A 108.9(4) . 3_766
N003 C00A H00A 109.9 . .
N003 C00A H00B 109.9 . .
C00A C00A H00A 109.9 3_766 .
C00A C00A H00B 109.9 3_766 .
H00A C00A H00B 108.3 . .
C006 C00B C007 121.1(4) . .
C006 C00B H00C 119.4 . .
C007 C00B H00C 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O001 C004 1.234(5) .
O002 H002 0.8400 .
O002 C004 1.324(6) .
N003 H003 0.8800 .
N003 C009 1.365(6) .
N003 C00A 1.453(6) .
C004 C007 1.463(7) .
C005 H005 0.9500 .
C005 C007 1.399(6) .
C005 C008 1.375(6) .
C006 H006 0.9500 .
C006 C009 1.416(6) .
C006 C00B 1.373(7) .
C007 C00B 1.399(6) .
C008 H008 0.9500 .
C008 C009 1.404(6) .
C00A C00A 1.514(9) 3_766
C00A H00A 0.9900 .
C00A H00B 0.9900 .
C00B H00C 0.9500 .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.743(4)
2 0.257(4)
