#------------------------------------------------------------------------------
#$Date: 2017-11-07 03:24:08 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/76/1547602.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_1547602
loop_
_publ_author_name
'Peng, Shan-Qing'
'Zhang, Xiao-Wei'
'Zhang, Long'
'Hu, Xiang-Guo'
_publ_section_title
;
 Esterification of Carboxylic Acids with Difluoromethyl Diazomethane and
 Interrupted Esterification with Trifluoromethyl Diazomethane: A Fluorine
 Effect.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5689
_journal_page_last               5692
_journal_paper_doi               10.1021/acs.orglett.7b02866
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         C11H9F2N1O2
_chemical_formula_sum            'C11 H9 F2 N O2'
_chemical_formula_weight         225.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.200(10)
_cell_angle_beta                 93.657(8)
_cell_angle_gamma                103.638(10)
_cell_formula_units_Z            2
_cell_length_a                   5.5743(6)
_cell_length_b                   8.0878(11)
_cell_length_c                   12.3099(11)
_cell_measurement_reflns_used    2608
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      3.6690
_cell_measurement_theta_min      3.6690
_cell_volume                     509.85(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5499
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0557
_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)+(0.0740P)²+0.0548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1474
_reflns_number_gt                1453
_reflns_number_total             1896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b02866_si_003.cif
_cod_data_source_block           fz2016112101
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1547602--1547605.cif.
;
_cod_original_cell_volume        509.85(10)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1547602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.3567(3) 0.1659(2) 1.07847(13) 0.0444(4) Uani 1 1 d .
H1 H 0.2103 0.1011 1.0785 0.053 Uiso 1 1 calc R
C6 C 0.5461(4) 0.2319(3) 1.16807(16) 0.0402(5) Uani 1 1 d .
C7 C 0.6807(4) 0.3193(3) 1.01890(17) 0.0451(5) Uani 1 1 d .
H7 H 0.7793 0.3710 0.9731 0.054 Uiso 1 1 calc R
C8 C 0.4369(4) 0.2194(3) 0.98816(16) 0.0411(5) Uani 1 1 d .
C1 C 0.7543(4) 0.3292(3) 1.13347(16) 0.0418(5) Uani 1 1 d .
C2 C 0.9763(4) 0.4094(3) 1.21204(19) 0.0529(6) Uani 1 1 d .
H2 H 1.1174 0.4740 1.1916 0.063 Uiso 1 1 calc R
C5 C 0.5512(4) 0.2141(3) 1.27738(17) 0.0483(5) Uani 1 1 d .
H5 H 0.4118 0.1496 1.2991 0.058 Uiso 1 1 calc R
C4 C 0.7704(4) 0.2954(3) 1.35159(18) 0.0527(6) Uani 1 1 d .
H4 H 0.7789 0.2869 1.4254 0.063 Uiso 1 1 calc R
C3 C 0.9807(4) 0.3906(3) 1.31899(18) 0.0548(6) Uani 1 1 d .
H3 H 1.1271 0.4424 1.3710 0.066 Uiso 1 1 calc R
O2 O 0.3684(3) 0.22732(19) 0.80180(11) 0.0507(4) Uani 1 1 d .
O1 O 0.0522(3) 0.0736(2) 0.86620(12) 0.0587(5) Uani 1 1 d .
C9 C 0.2654(4) 0.1648(3) 0.88231(17) 0.0429(5) Uani 1 1 d .
C10 C 0.2106(4) 0.1733(3) 0.69391(17) 0.0525(6) Uani 1 1 d .
H10A H 0.0603 0.2135 0.7042 0.063 Uiso 1 1 calc R
H10B H 0.1634 0.0436 0.6600 0.063 Uiso 1 1 calc R
F1 F 0.2187(3) 0.2106(2) 0.51620(12) 0.0956(6) Uani 1 1 d .
C11 C 0.3588(5) 0.2585(4) 0.6200(2) 0.0653(7) Uani 1 1 d .
H11 H 0.4068 0.3894 0.6550 0.078 Uiso 1 1 calc R
F2 F 0.5629(3) 0.1986(2) 0.60133(13) 0.0902(6) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0374(9) 0.0544(10) 0.0402(10) 0.0184(8) 0.0061(8) 0.0060(8)
C6 0.0419(11) 0.0430(11) 0.0358(10) 0.0122(9) 0.0050(9) 0.0123(9)
C7 0.0470(12) 0.0477(12) 0.0412(11) 0.0196(10) 0.0087(10) 0.0061(10)
C8 0.0466(11) 0.0435(11) 0.0353(11) 0.0149(9) 0.0080(9) 0.0128(9)
C1 0.0447(11) 0.0416(11) 0.0384(11) 0.0132(9) 0.0040(9) 0.0100(9)
C2 0.0462(12) 0.0563(13) 0.0511(13) 0.0183(11) 0.0028(10) 0.0038(10)
C5 0.0504(12) 0.0553(13) 0.0417(12) 0.0206(10) 0.0090(10) 0.0114(10)
C4 0.0630(14) 0.0586(14) 0.0378(11) 0.0178(10) 0.0026(10) 0.0173(11)
C3 0.0519(13) 0.0586(14) 0.0472(13) 0.0142(11) -0.0063(11) 0.0092(11)
O2 0.0495(9) 0.0601(9) 0.0384(8) 0.0219(7) -0.0011(7) 0.0012(7)
O1 0.0428(9) 0.0794(11) 0.0519(10) 0.0270(8) 0.0053(7) 0.0056(8)
C9 0.0457(12) 0.0469(12) 0.0392(11) 0.0157(9) 0.0080(9) 0.0153(10)
C10 0.0546(13) 0.0587(13) 0.0399(12) 0.0189(10) -0.0054(10) 0.0062(11)
F1 0.1021(13) 0.1317(15) 0.0496(9) 0.0444(9) -0.0108(9) 0.0105(11)
C11 0.0739(17) 0.0789(17) 0.0444(13) 0.0270(12) 0.0004(12) 0.0159(14)
F2 0.0809(11) 0.1257(14) 0.0721(11) 0.0369(10) 0.0259(9) 0.0320(10)
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'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 '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
C6 N1 C8 109.07(16)
C6 N1 H1 125.5
C8 N1 H1 125.5
N1 C6 C5 129.66(19)
N1 C6 C1 107.97(16)
C5 C6 C1 122.36(19)
C8 C7 C1 107.20(18)
C8 C7 H7 126.4
C1 C7 H7 126.4
N1 C8 C7 109.12(17)
N1 C8 C9 119.02(18)
C7 C8 C9 131.86(18)
C6 C1 C2 118.51(18)
C6 C1 C7 106.64(17)
C2 C1 C7 134.8(2)
C3 C2 C1 118.9(2)
C3 C2 H2 120.6
C1 C2 H2 120.6
C4 C5 C6 117.3(2)
C4 C5 H5 121.4
C6 C5 H5 121.4
C5 C4 C3 121.6(2)
C5 C4 H4 119.2
C3 C4 H4 119.2
C2 C3 C4 121.4(2)
C2 C3 H3 119.3
C4 C3 H3 119.3
C9 O2 C10 115.17(16)
O1 C9 O2 122.45(19)
O1 C9 C8 125.02(18)
O2 C9 C8 112.53(17)
O2 C10 C11 105.88(17)
O2 C10 H10A 110.6
C11 C10 H10A 110.6
O2 C10 H10B 110.6
C11 C10 H10B 110.6
H10A C10 H10B 108.7
F2 C11 F1 106.6(2)
F2 C11 C10 111.24(19)
F1 C11 C10 108.4(2)
F2 C11 H11 110.2
F1 C11 H11 110.2
C10 C11 H11 110.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.362(2)
N1 C8 1.371(2)
N1 H1 0.8600
C6 C5 1.394(3)
C6 C1 1.407(3)
C7 C8 1.371(3)
C7 C1 1.417(3)
C7 H7 0.9300
C8 C9 1.452(3)
C1 C2 1.409(3)
C2 C3 1.369(3)
C2 H2 0.9300
C5 C4 1.372(3)
C5 H5 0.9300
C4 C3 1.395(3)
C4 H4 0.9300
C3 H3 0.9300
O2 C9 1.341(2)
O2 C10 1.434(2)
O1 C9 1.211(2)
C10 C11 1.477(3)
C10 H10A 0.9700
C10 H10B 0.9700
F1 C11 1.353(3)
C11 F2 1.345(3)
C11 H11 0.9800
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
C8 N1 C6 C5 179.38(19)
C8 N1 C6 C1 -0.5(2)
C6 N1 C8 C7 0.6(2)
C6 N1 C8 C9 -179.91(15)
C1 C7 C8 N1 -0.4(2)
C1 C7 C8 C9 -179.83(19)
N1 C6 C1 C2 -179.32(17)
C5 C6 C1 C2 0.8(3)
N1 C6 C1 C7 0.3(2)
C5 C6 C1 C7 -179.63(18)
C8 C7 C1 C6 0.1(2)
C8 C7 C1 C2 179.6(2)
C6 C1 C2 C3 -0.4(3)
C7 C1 C2 C3 -179.8(2)
N1 C6 C5 C4 179.87(18)
C1 C6 C5 C4 -0.3(3)
C6 C5 C4 C3 -0.7(3)
C1 C2 C3 C4 -0.5(3)
C5 C4 C3 C2 1.1(3)
C10 O2 C9 O1 -2.0(3)
C10 O2 C9 C8 178.14(15)
N1 C8 C9 O1 -0.1(3)
C7 C8 C9 O1 179.3(2)
N1 C8 C9 O2 179.70(15)
C7 C8 C9 O2 -0.9(3)
C9 O2 C10 C11 179.21(17)
O2 C10 C11 F2 62.7(3)
O2 C10 C11 F1 179.53(18)
