#------------------------------------------------------------------------------
#$Date: 2019-11-23 16:20:14 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233981 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/45/7124588.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_7124588
loop_
_publ_author_name
'Wang, Nan-Nan'
'Hao, Wen-Juan'
'Zhang, Tian-Shu'
'Li, Guigen'
'Wu, Ya-Nan'
'Tu, Shu-Jiang'
'Jiang, Bo'
_publ_section_title
;
 Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of
 α-diazo carbonyls via radical dediazotization.
;
_journal_issue                   29
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5144
_journal_page_last               5147
_journal_paper_doi               10.1039/c6cc00816j
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C25 H22 N2 O4'
_chemical_formula_weight         414.45
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2016-01-25 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.340(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.398(6)
_cell_length_b                   11.272(5)
_cell_length_c                   16.887(8)
_cell_measurement_reflns_used    1982
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.172
_cell_measurement_theta_min      2.438
_cell_volume                     2146.7(18)
_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      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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10526
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0240P)²+0.5465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                1882
_reflns_number_total             3780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc00816j2.cif
_cod_data_source_block           150717f
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7124588
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
N1 N 0.33108(16) 0.65408(19) 0.16565(12) 0.0595(6) Uani 1 1 d .
N2 N 0.32897(19) 0.83138(19) 0.37312(12) 0.0652(6) Uani 1 1 d .
O1 O 0.37778(13) 0.75089(14) 0.20933(9) 0.0590(5) Uani 1 1 d .
O2 O 0.14563(15) 0.65874(17) 0.20413(11) 0.0838(6) Uani 1 1 d .
O3 O 0.49292(15) 0.61437(17) 0.10394(10) 0.0797(6) Uani 1 1 d .
O4 O 0.59090(16) 0.57234(17) 0.30989(12) 0.0893(6) Uani 1 1 d .
C1 C 0.2142(2) 0.6178(2) 0.16429(15) 0.0587(7) Uani 1 1 d .
C2 C 0.3914(2) 0.5959(2) 0.11162(14) 0.0572(7) Uani 1 1 d .
C3 C 0.3044(2) 0.5102(2) 0.07234(14) 0.0529(6) Uani 1 1 d .
C4 C 0.2009(2) 0.5213(2) 0.10450(14) 0.0573(7) Uani 1 1 d .
C5 C 0.1066(3) 0.4500(3) 0.08010(18) 0.0906(10) Uani 1 1 d .
H5 H 0.0370 0.4563 0.1025 0.109 Uiso 1 1 calc R
C6 C 0.1173(3) 0.3679(3) 0.0211(2) 0.1116(12) Uani 1 1 d .
H6 H 0.0535 0.3189 0.0029 0.134 Uiso 1 1 calc R
C7 C 0.2206(3) 0.3575(3) -0.01120(17) 0.0910(10) Uani 1 1 d .
H7 H 0.2257 0.3011 -0.0508 0.109 Uiso 1 1 calc R
C8 C 0.3166(2) 0.4289(3) 0.01400(15) 0.0708(8) Uani 1 1 d .
H8 H 0.3867 0.4222 -0.0077 0.085 Uiso 1 1 calc R
C9 C 0.4394(2) 0.8196(2) 0.34154(15) 0.0671(7) Uani 1 1 d .
H9A H 0.5035 0.8115 0.3857 0.081 Uiso 1 1 calc R
H9B H 0.4534 0.8915 0.3127 0.081 Uiso 1 1 calc R
C10 C 0.4416(2) 0.7140(2) 0.28577(14) 0.0562(7) Uani 1 1 d .
H10 H 0.3972 0.6491 0.3062 0.067 Uiso 1 1 calc R
C11 C 0.5671(2) 0.6701(2) 0.28158(14) 0.0581(7) Uani 1 1 d .
C12 C 0.6584(2) 0.7432(2) 0.25140(13) 0.0509(6) Uani 1 1 d .
C13 C 0.7750(2) 0.7061(2) 0.26778(15) 0.0633(7) Uani 1 1 d .
H13 H 0.7933 0.6381 0.2983 0.076 Uiso 1 1 calc R
C14 C 0.8642(2) 0.7680(3) 0.23983(16) 0.0716(8) Uani 1 1 d .
H14 H 0.9420 0.7415 0.2521 0.086 Uiso 1 1 calc R
C15 C 0.8406(2) 0.8688(3) 0.19388(16) 0.0642(7) Uani 1 1 d .
C16 C 0.7244(2) 0.9052(2) 0.17752(14) 0.0624(7) Uani 1 1 d .
H16 H 0.7064 0.9728 0.1465 0.075 Uiso 1 1 calc R
C17 C 0.6339(2) 0.8445(2) 0.20571(14) 0.0595(7) Uani 1 1 d .
H17 H 0.5562 0.8717 0.1940 0.071 Uiso 1 1 calc R
C18 C 0.9385(2) 0.9369(3) 0.16363(18) 0.1014(11) Uani 1 1 d .
H18A H 0.9615 1.0024 0.1988 0.152 Uiso 1 1 calc R
H18B H 0.9110 0.9661 0.1108 0.152 Uiso 1 1 calc R
H18C H 1.0053 0.8856 0.1620 0.152 Uiso 1 1 calc R
C19 C 0.2994(2) 0.7489(2) 0.42758(15) 0.0616(7) Uani 1 1 d .
C20 C 0.3834(3) 0.6741(3) 0.46938(16) 0.0776(8) Uani 1 1 d .
H20 H 0.4611 0.6768 0.4586 0.093 Uiso 1 1 calc R
C21 C 0.3550(4) 0.5969(3) 0.52584(18) 0.0978(11) Uani 1 1 d .
H21 H 0.4136 0.5487 0.5532 0.117 Uiso 1 1 calc R
C22 C 0.2422(4) 0.5894(3) 0.5427(2) 0.1127(13) Uani 1 1 d .
H22 H 0.2232 0.5372 0.5815 0.135 Uiso 1 1 calc R
C23 C 0.1575(3) 0.6604(3) 0.5012(2) 0.1110(12) Uani 1 1 d .
H23 H 0.0796 0.6550 0.5114 0.133 Uiso 1 1 calc R
C24 C 0.1848(3) 0.7399(3) 0.44456(17) 0.0845(9) Uani 1 1 d .
H24 H 0.1257 0.7879 0.4176 0.101 Uiso 1 1 calc R
C25 C 0.2374(2) 0.9020(2) 0.32712(16) 0.0815(9) Uani 1 1 d .
H25A H 0.1813 0.8506 0.2961 0.122 Uiso 1 1 calc R
H25B H 0.2725 0.9537 0.2919 0.122 Uiso 1 1 calc R
H25C H 0.1977 0.9485 0.3628 0.122 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
O1 N1 C2 122.46(19)
O1 N1 C1 122.4(2)
C2 N1 C1 114.6(2)
C19 N2 C9 119.6(2)
C19 N2 C25 120.0(2)
C9 N2 C25 116.9(2)
N1 O1 C10 110.75(17)
O2 C1 N1 125.5(3)
O2 C1 C4 131.1(2)
N1 C1 C4 103.4(2)
O3 C2 N1 124.6(2)
O3 C2 C3 131.4(2)
N1 C2 C3 104.0(2)
C8 C3 C4 121.9(2)
C8 C3 C2 129.3(2)
C4 C3 C2 108.9(2)
C5 C4 C3 120.9(3)
C5 C4 C1 130.0(3)
C3 C4 C1 109.1(2)
C4 C5 C6 117.9(3)
C4 C5 H5 121.1
C6 C5 H5 121.1
C7 C6 C5 121.1(3)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C8 121.1(3)
C6 C7 H7 119.5
C8 C7 H7 119.5
C3 C8 C7 117.2(3)
C3 C8 H8 121.4
C7 C8 H8 121.4
N2 C9 C10 113.2(2)
N2 C9 H9A 108.9
C10 C9 H9A 108.9
N2 C9 H9B 108.9
C10 C9 H9B 108.9
H9A C9 H9B 107.7
O1 C10 C9 106.01(19)
O1 C10 C11 113.90(19)
C9 C10 C11 112.5(2)
O1 C10 H10 108.1
C9 C10 H10 108.1
C11 C10 H10 108.1
O4 C11 C12 120.8(2)
O4 C11 C10 115.7(2)
C12 C11 C10 123.3(2)
C13 C12 C17 118.1(2)
C13 C12 C11 118.0(2)
C17 C12 C11 123.9(2)
C14 C13 C12 121.1(2)
C14 C13 H13 119.4
C12 C13 H13 119.4
C13 C14 C15 121.2(3)
C13 C14 H14 119.4
C15 C14 H14 119.4
C16 C15 C14 117.5(2)
C16 C15 C18 121.3(3)
C14 C15 C18 121.2(3)
C15 C16 C17 122.0(2)
C15 C16 H16 119.0
C17 C16 H16 119.0
C16 C17 C12 120.1(2)
C16 C17 H17 120.0
C12 C17 H17 120.0
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C24 C19 N2 121.1(3)
C24 C19 C20 117.0(3)
N2 C19 C20 121.9(3)
C21 C20 C19 121.7(3)
C21 C20 H20 119.1
C19 C20 H20 119.1
C22 C21 C20 120.9(3)
C22 C21 H21 119.6
C20 C21 H21 119.6
C21 C22 C23 118.5(3)
C21 C22 H22 120.8
C23 C22 H22 120.8
C22 C23 C24 121.4(3)
C22 C23 H23 119.3
C24 C23 H23 119.3
C23 C24 C19 120.5(3)
C23 C24 H24 119.8
C19 C24 H24 119.8
N2 C25 H25A 109.5
N2 C25 H25B 109.5
H25A C25 H25B 109.5
N2 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O1 1.380(2)
N1 C2 1.385(3)
N1 C1 1.390(3)
N2 C19 1.384(3)
N2 C9 1.443(3)
N2 C25 1.446(3)
O1 C10 1.448(3)
O2 C1 1.196(3)
O3 C2 1.201(3)
O4 C11 1.217(3)
C1 C4 1.477(3)
C2 C3 1.472(3)
C3 C8 1.367(3)
C3 C4 1.375(3)
C4 C5 1.357(3)
C5 C6 1.378(4)
C5 H5 0.9300
C6 C7 1.372(4)
C6 H6 0.9300
C7 C8 1.375(4)
C7 H7 0.9300
C8 H8 0.9300
C9 C10 1.521(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.524(3)
C10 H10 0.9800
C11 C12 1.475(3)
C12 C13 1.382(3)
C12 C17 1.384(3)
C13 C14 1.372(3)
C13 H13 0.9300
C14 C15 1.380(3)
C14 H14 0.9300
C15 C16 1.376(3)
C15 C18 1.503(3)
C16 C17 1.380(3)
C16 H16 0.9300
C17 H17 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 C24 1.380(4)
C19 C20 1.389(3)
C20 C21 1.365(4)
C20 H20 0.9300
C21 C22 1.359(4)
C21 H21 0.9300
C22 C23 1.366(4)
C22 H22 0.9300
C23 C24 1.379(4)
C23 H23 0.9300
C24 H24 0.9300
C25 H25A 0.9600
C25 H25B 0.9600
C25 H25C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 N1 O1 C10 -92.0(2)
C1 N1 O1 C10 97.0(2)
O1 N1 C1 O2 -6.0(4)
C2 N1 C1 O2 -177.6(3)
O1 N1 C1 C4 174.29(19)
C2 N1 C1 C4 2.7(3)
O1 N1 C2 O3 8.7(4)
C1 N1 C2 O3 -179.7(2)
O1 N1 C2 C3 -173.15(18)
C1 N1 C2 C3 -1.6(3)
O3 C2 C3 C8 -1.6(5)
N1 C2 C3 C8 -179.6(2)
O3 C2 C3 C4 177.6(3)
N1 C2 C3 C4 -0.4(3)
C8 C3 C4 C5 1.0(4)
C2 C3 C4 C5 -178.3(2)
C8 C3 C4 C1 -178.7(2)
C2 C3 C4 C1 2.0(3)
O2 C1 C4 C5 -2.1(5)
N1 C1 C4 C5 177.5(3)
O2 C1 C4 C3 177.6(3)
N1 C1 C4 C3 -2.8(3)
C3 C4 C5 C6 -1.2(4)
C1 C4 C5 C6 178.4(3)
C4 C5 C6 C7 0.9(5)
C5 C6 C7 C8 -0.3(6)
C4 C3 C8 C7 -0.4(4)
C2 C3 C8 C7 178.8(2)
C6 C7 C8 C3 0.0(4)
C19 N2 C9 C10 69.3(3)
C25 N2 C9 C10 -89.7(3)
N1 O1 C10 C9 -154.75(18)
N1 O1 C10 C11 81.0(2)
N2 C9 C10 O1 79.7(2)
N2 C9 C10 C11 -155.2(2)
O1 C10 C11 O4 -126.5(2)
C9 C10 C11 O4 112.9(3)
O1 C10 C11 C12 58.2(3)
C9 C10 C11 C12 -62.4(3)
O4 C11 C12 C13 -10.2(4)
C10 C11 C12 C13 164.8(2)
O4 C11 C12 C17 167.8(2)
C10 C11 C12 C17 -17.2(4)
C17 C12 C13 C14 0.2(4)
C11 C12 C13 C14 178.3(2)
C12 C13 C14 C15 -0.5(4)
C13 C14 C15 C16 0.3(4)
C13 C14 C15 C18 179.7(2)
C14 C15 C16 C17 0.2(4)
C18 C15 C16 C17 -179.2(2)
C15 C16 C17 C12 -0.5(4)
C13 C12 C17 C16 0.3(3)
C11 C12 C17 C16 -177.7(2)
C9 N2 C19 C24 -164.4(2)
C25 N2 C19 C24 -6.1(4)
C9 N2 C19 C20 17.6(4)
C25 N2 C19 C20 175.9(2)
C24 C19 C20 C21 -1.3(4)
N2 C19 C20 C21 176.8(3)
C19 C20 C21 C22 0.7(5)
C20 C21 C22 C23 0.6(6)
C21 C22 C23 C24 -1.3(6)
C22 C23 C24 C19 0.7(5)
N2 C19 C24 C23 -177.5(3)
C20 C19 C24 C23 0.5(4)
