#------------------------------------------------------------------------------
#$Date: 2020-04-03 02:31:07 +0300 (Fri, 03 Apr 2020) $
#$Revision: 249983 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038172.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_4038172
loop_
_publ_author_name
'François, Benjamin'
'Eberlin, Ludovic'
'Berrée, Fabienne'
'Whiting, Andrew'
'Carboni, Bertrand'
_publ_section_title
;
 Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and
 Arylnitroso Compounds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03214
_journal_year                    2020
_chemical_formula_moiety         'C20 H26 B N O5'
_chemical_formula_sum            'C20 H26 B N O5'
_chemical_formula_weight         371.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-31
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.573(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8072(10)
_cell_length_b                   10.7432(9)
_cell_length_c                   14.2090(11)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.94
_cell_measurement_theta_min      2.32
_cell_volume                     1933.2(3)
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            44140
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        30.943
_diffrn_reflns_theta_max         30.943
_diffrn_reflns_theta_min         2.320
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0832 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.9678.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.257
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         6129
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0620P)²+0.8450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5268
_reflns_number_total             6129
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03214_si_001.cif
_cod_data_source_block           15srv085
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038172
_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.
;
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.972
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O3A-C11 \\sim O3B-C11
 with sigma of 0.01
 O3A-N \\sim O3B-N
 with sigma of 0.01
3. Others
 Uiso(H3A)=Uiso(H3B)=Uiso(H3C)=FVAR(1)
 Uiso(H4A)=Uiso(H4B)=Uiso(H4C)=FVAR(2)
 Uiso(H5A)=Uiso(H5B)=Uiso(H5C)=FVAR(3)
 Uiso(H6A)=Uiso(H6B)=Uiso(H6C)=FVAR(4)
 Fixed Sof: H11A(0.875) H11B(0.875) H11C(0.125) H11D(0.125) O3A(0.89) O3B(0.11)
4.a Rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11(H11C,H11D), C12(H12A,H12B), C14(H14A,H14B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_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+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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53576(6) 0.92958(7) 0.84235(5) 0.01786(15) Uani 1 1 d . . . . .
O2 O 0.62374(7) 0.95483(7) 0.71461(5) 0.02109(16) Uani 1 1 d . . . . .
O4 O 0.48182(8) 0.31457(9) 0.53560(7) 0.0316(2) Uani 1 1 d . . . . .
O5 O 0.34050(6) 0.20240(7) 0.56582(5) 0.01971(16) Uani 1 1 d . . . . .
N N 0.37316(7) 0.38890(8) 0.63480(6) 0.01784(17) Uani 1 1 d D . . . .
C1 C 0.57886(8) 1.05569(9) 0.85020(7) 0.01714(18) Uani 1 1 d . . . . .
C2 C 0.66555(9) 1.05027(9) 0.78383(7) 0.01879(19) Uani 1 1 d . . . . .
C3 C 0.48787(10) 1.14273(11) 0.81436(10) 0.0291(2) Uani 1 1 d . . . . .
H3A H 0.4630 1.1258 0.7470 0.038(3) Uiso 1 1 d GR . . . .
H3B H 0.5120 1.2292 0.8218 0.038(3) Uiso 1 1 d GR . . . .
H3C H 0.4300 1.1292 0.8512 0.038(3) Uiso 1 1 d GR . . . .
C4 C 0.62075(10) 1.08130(11) 0.95393(8) 0.0242(2) Uani 1 1 d . . . . .
H4A H 0.5617 1.0851 0.9905 0.032(2) Uiso 1 1 d GR . . . .
H4B H 0.6586 1.1609 0.9593 0.032(2) Uiso 1 1 d GR . . . .
H4C H 0.6691 1.0144 0.9790 0.032(2) Uiso 1 1 d GR . . . .
C5 C 0.68165(12) 1.16976(11) 0.73125(9) 0.0292(3) Uani 1 1 d . . . . .
H5A H 0.7366 1.1572 0.6910 0.039(3) Uiso 1 1 d GR . . . .
H5B H 0.7033 1.2362 0.7773 0.039(3) Uiso 1 1 d GR . . . .
H5C H 0.6154 1.1932 0.6914 0.039(3) Uiso 1 1 d GR . . . .
C6 C 0.77100(9) 1.00133(12) 0.83318(10) 0.0283(2) Uani 1 1 d . . . . .
H6A H 0.7599 0.9236 0.8663 0.034(2) Uiso 1 1 d GR . . . .
H6B H 0.8035 1.0631 0.8793 0.034(2) Uiso 1 1 d GR . . . .
H6C H 0.8177 0.9858 0.7857 0.034(2) Uiso 1 1 d GR . . . .
C7 C 0.51063(8) 0.75723(9) 0.71598(7) 0.01688(18) Uani 1 1 d . . . . .
H7 H 0.5320 0.7252 0.6595 0.020 Uiso 1 1 calc R . . . .
C8 C 0.44013(8) 0.69414(9) 0.75824(7) 0.01538(18) Uani 1 1 d . . . . .
H8 H 0.4214 0.7297 0.8146 0.018 Uiso 1 1 calc R . . . .
C9 C 0.38913(8) 0.57700(9) 0.72708(7) 0.01474(17) Uani 1 1 d . . . . .
C10 C 0.31972(10) 0.52492(11) 0.77655(8) 0.0252(2) Uani 1 1 d . . . . .
H10 H 0.3071 0.5634 0.8340 0.030 Uiso 1 1 calc R . . . .
C11 C 0.26124(9) 0.40867(11) 0.74507(8) 0.0247(2) Uani 1 1 d D . . . .
H11A H 0.2921 0.3379 0.7844 0.030 Uiso 0.875 1 calc R . P A 1
H11B H 0.1865 0.4174 0.7543 0.030 Uiso 0.875 1 calc R . P A 1
H11C H 0.2382 0.3664 0.8004 0.030 Uiso 0.125 1 calc R . P B 2
H11D H 0.1978 0.4288 0.6988 0.030 Uiso 0.125 1 calc R . P B 2
C12 C 0.41636(9) 0.51342(10) 0.63938(8) 0.0208(2) Uani 1 1 d . . . . .
H12A H 0.3865 0.5608 0.5819 0.025 Uiso 1 1 calc R . . . .
H12B H 0.4940 0.5098 0.6421 0.025 Uiso 1 1 calc R . . . .
C13 C 0.40380(8) 0.30268(9) 0.57352(7) 0.01795(19) Uani 1 1 d . . . . .
C14 C 0.37449(11) 0.10275(12) 0.50824(10) 0.0311(3) Uani 1 1 d . . . . .
H14A H 0.4416 0.0664 0.5400 0.037 Uiso 1 1 calc R . . . .
H14B H 0.3856 0.1350 0.4452 0.037 Uiso 1 1 calc R . . . .
C15 C 0.28906(9) 0.00622(10) 0.49688(7) 0.0201(2) Uani 1 1 d . . . . .
C16 C 0.18710(10) 0.03592(11) 0.45382(9) 0.0263(2) Uani 1 1 d . . . . .
H16 H 0.1716 0.1182 0.4314 0.032 Uiso 1 1 calc R . . . .
C17 C 0.10835(10) -0.05319(13) 0.44338(9) 0.0303(3) Uani 1 1 d . . . . .
H17 H 0.0389 -0.0320 0.4144 0.036 Uiso 1 1 calc R . . . .
C18 C 0.13084(11) -0.17364(12) 0.47529(9) 0.0307(3) Uani 1 1 d . . . . .
H18 H 0.0769 -0.2351 0.4685 0.037 Uiso 1 1 calc R . . . .
C19 C 0.23178(12) -0.20384(11) 0.51693(9) 0.0299(3) Uani 1 1 d . . . . .
H19 H 0.2473 -0.2864 0.5385 0.036 Uiso 1 1 calc R . . . .
C20 C 0.31117(10) -0.11416(11) 0.52766(8) 0.0247(2) Uani 1 1 d . . . . .
H20 H 0.3806 -0.1358 0.5562 0.030 Uiso 1 1 calc R . . . .
B B 0.55764(9) 0.88150(10) 0.75795(8) 0.0162(2) Uani 1 1 d . . . . .
O3A O 0.26654(6) 0.38389(8) 0.64727(6) 0.01882(17) Uani 0.89 1 d D . P C 1
O3B O 0.3233(5) 0.3366(6) 0.7060(4) 0.0205(13) Uiso 0.11 1 d D . P C 2
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'
B B 0.0013 0.0007 '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
_geom_angle_publ_flag
B O1 C1 106.96(8) . . ?
B O2 C2 106.83(8) . . ?
C13 O5 C14 114.14(8) . . ?
C13 N C12 120.73(8) . . ?
C13 N O3A 115.53(8) . . ?
C13 N O3B 113.3(3) . . ?
O3A N C12 113.75(8) . . ?
O3B N C12 123.7(3) . . ?
O1 C1 C2 102.36(7) . . ?
O1 C1 C3 106.41(9) . . ?
O1 C1 C4 108.50(8) . . ?
C3 C1 C2 113.51(9) . . ?
C4 C1 C2 114.42(9) . . ?
C4 C1 C3 110.86(9) . . ?
O2 C2 C1 102.11(8) . . ?
O2 C2 C5 108.96(9) . . ?
O2 C2 C6 106.15(9) . . ?
C5 C2 C1 115.32(9) . . ?
C5 C2 C6 110.11(10) . . ?
C6 C2 C1 113.41(9) . . ?
C8 C7 B 120.87(9) . . ?
C7 C8 C9 127.04(9) . . ?
C8 C9 C12 119.65(8) . . ?
C10 C9 C8 120.37(9) . . ?
C10 C9 C12 119.97(9) . . ?
C9 C10 C11 122.50(10) . . ?
O3A C11 C10 110.73(9) . . ?
O3B C11 C10 108.5(3) . . ?
N C12 C9 108.82(8) . . ?
O4 C13 O5 125.21(9) . . ?
O4 C13 N 123.09(9) . . ?
O5 C13 N 111.59(9) . . ?
O5 C14 C15 107.17(9) . . ?
C16 C15 C14 120.66(11) . . ?
C20 C15 C14 120.13(11) . . ?
C20 C15 C16 119.20(10) . . ?
C17 C16 C15 120.61(11) . . ?
C16 C17 C18 119.89(12) . . ?
C19 C18 C17 119.73(11) . . ?
C18 C19 C20 120.47(11) . . ?
C15 C20 C19 120.09(11) . . ?
O1 B C7 122.90(9) . . ?
O2 B O1 113.40(9) . . ?
O2 B C7 123.69(9) . . ?
N O3A C11 107.71(8) . . ?
C11 O3B N 116.6(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4609(12) . ?
O1 B 1.3724(13) . ?
O2 C2 1.4657(12) . ?
O2 B 1.3682(13) . ?
O4 C13 1.2105(13) . ?
O5 C13 1.3430(12) . ?
O5 C14 1.4530(13) . ?
N C12 1.4454(13) . ?
N C13 1.3682(13) . ?
N O3A 1.4039(11) . ?
N O3B 1.393(6) . ?
C1 C2 1.5612(15) . ?
C1 C3 1.5215(16) . ?
C1 C4 1.5166(15) . ?
C2 C5 1.5148(15) . ?
C2 C6 1.5198(17) . ?
C7 C8 1.3404(14) . ?
C7 B 1.5471(14) . ?
C8 C9 1.4560(13) . ?
C9 C10 1.3357(14) . ?
C9 C12 1.5068(14) . ?
C10 C11 1.4903(15) . ?
C11 O3A 1.4264(14) . ?
C11 O3B 1.293(6) . ?
C14 C15 1.4987(15) . ?
C15 C16 1.3940(17) . ?
C15 C20 1.3809(16) . ?
C16 C17 1.3824(18) . ?
C17 C18 1.387(2) . ?
C18 C19 1.378(2) . ?
C19 C20 1.3925(17) . ?
