#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:57:53 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234541 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/63/4036320.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_4036320
loop_
_publ_author_name
'Ram, Ram N.'
'Soni, Vineet Kumar'
_publ_section_title
;
 Synthesis of α-Functionalized Trichloromethylcarbinols.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8922
_journal_page_last               8928
_journal_paper_doi               10.1021/acs.joc.5b01547
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C19 H17 Cl3 N2 O4'
_chemical_formula_sum            'C19 H17 Cl3 N2 O4'
_chemical_formula_weight         443.70
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                 92.949(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.054(2)
_cell_length_b                   17.784(5)
_cell_length_c                   12.497(3)
_cell_measurement_reflns_used    1915
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.49
_cell_measurement_theta_min      2.19
_cell_volume                     2009.6(9)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17746
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.1115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                3060
_reflns_number_total             3540
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01547_si_002.cif
_cod_data_source_block           vin1m
_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/ACS/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_cell_volume        2009.4(9)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4036320
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
Cl1 Cl 0.49551(5) 0.16468(3) 0.78669(4) 0.03668(15) Uani 1 1 d .
Cl2 Cl 0.48260(5) 0.16628(3) 1.01451(4) 0.03655(15) Uani 1 1 d .
Cl3 Cl 0.36869(6) 0.03801(3) 0.89440(4) 0.04207(16) Uani 1 1 d .
O1 O 0.36025(15) 0.39891(8) 0.80009(12) 0.0423(3) Uani 1 1 d .
O2 O 0.17112(14) 0.26649(7) 0.70972(9) 0.0337(3) Uani 1 1 d .
O3 O 0.24367(13) 0.25159(6) 0.88459(9) 0.0269(3) Uani 1 1 d .
O4 O 0.15857(16) 0.15340(10) 1.05709(10) 0.0538(4) Uani 1 1 d .
N1 N 0.12679(17) 0.41456(8) 0.85676(11) 0.0292(3) Uani 1 1 d .
N2 N -0.00552(15) 0.11868(8) 0.92477(11) 0.0281(3) Uani 1 1 d .
C1 C -0.01654(19) 0.38288(10) 0.87535(13) 0.0272(4) Uani 1 1 d .
C2 C -0.0403(2) 0.34759(10) 0.97159(15) 0.0324(4) Uani 1 1 d .
H2 H 0.0375 0.3403 1.0221 0.039 Uiso 1 1 calc R
C3 C -0.1818(2) 0.32312(11) 0.99194(16) 0.0393(5) Uani 1 1 d .
H3 H -0.1990 0.2993 1.0563 0.047 Uiso 1 1 calc R
C4 C -0.2966(2) 0.33409(11) 0.91710(17) 0.0399(5) Uani 1 1 d .
H4 H -0.3916 0.3186 0.9318 0.048 Uiso 1 1 calc R
C5 C -0.2715(2) 0.36782(12) 0.82062(16) 0.0406(5) Uani 1 1 d .
H5 H -0.3490 0.3740 0.7696 0.049 Uiso 1 1 calc R
C6 C -0.1311(2) 0.39256(11) 0.79937(15) 0.0347(4) Uani 1 1 d .
H6 H -0.1140 0.4156 0.7343 0.042 Uiso 1 1 calc R
C7 C 0.23778(19) 0.37482(10) 0.81793(13) 0.0278(4) Uani 1 1 d .
C8 C 0.20823(18) 0.29184(10) 0.79460(13) 0.0250(4) Uani 1 1 d .
C9 C 0.23279(19) 0.17104(9) 0.87729(13) 0.0256(4) Uani 1 1 d .
H9 H 0.1921 0.1570 0.8059 0.031 Uiso 1 1 calc R
C10 C 0.1250(2) 0.14618(10) 0.96235(14) 0.0304(4) Uani 1 1 d .
C11 C -0.05266(18) 0.11723(9) 0.81292(13) 0.0257(4) Uani 1 1 d .
C12 C -0.0296(2) 0.05355(11) 0.75263(15) 0.0358(4) Uani 1 1 d .
H12 H 0.0137 0.0111 0.7843 0.043 Uiso 1 1 calc R
C13 C -0.0712(2) 0.05372(12) 0.64559(17) 0.0462(5) Uani 1 1 d .
H13 H -0.0552 0.0114 0.6040 0.055 Uiso 1 1 calc R
C14 C -0.1369(2) 0.11682(13) 0.59949(16) 0.0442(5) Uani 1 1 d .
H14 H -0.1637 0.1169 0.5266 0.053 Uiso 1 1 calc R
C15 C -0.1633(2) 0.17965(12) 0.66038(16) 0.0389(5) Uani 1 1 d .
H15 H -0.2090 0.2216 0.6291 0.047 Uiso 1 1 calc R
C16 C -0.1213(2) 0.17961(10) 0.76761(15) 0.0314(4) Uani 1 1 d .
H16 H -0.1391 0.2215 0.8095 0.038 Uiso 1 1 calc R
C17 C 0.1505(2) 0.49363(10) 0.88725(16) 0.0393(5) Uani 1 1 d .
H17A H 0.1513 0.4982 0.9638 0.059 Uiso 1 1 calc R
H17B H 0.0721 0.5239 0.8554 0.059 Uiso 1 1 calc R
H17C H 0.2435 0.5105 0.8624 0.059 Uiso 1 1 calc R
C18 C 0.38734(19) 0.13762(10) 0.89521(13) 0.0278(4) Uani 1 1 d .
C19 C -0.1148(2) 0.09675(14) 1.00121(16) 0.0463(5) Uani 1 1 d .
H19A H -0.0691 0.0961 1.0722 0.069 Uiso 1 1 calc R
H19B H -0.1521 0.0475 0.9834 0.069 Uiso 1 1 calc R
H19C H -0.1948 0.1322 0.9981 0.069 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'
Cl Cl 0.1484 0.1585 '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
C8 O3 C9 117.39(13)
C7 N1 C1 123.32(15)
C7 N1 C17 119.76(15)
C1 N1 C17 116.86(14)
C10 N2 C11 123.92(14)
C10 N2 C19 118.79(15)
C11 N2 C19 116.89(14)
C6 C1 C2 120.64(17)
C6 C1 N1 119.35(16)
C2 C1 N1 119.87(16)
C1 C2 C3 119.19(18)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 120.19(18)
C4 C3 H3 119.9
C2 C3 H3 119.9
C5 C4 C3 120.27(19)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.11(19)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 119.57(18)
C1 C6 H6 120.2
C5 C6 H6 120.2
O1 C7 N1 125.92(17)
O1 C7 C8 117.20(15)
N1 C7 C8 116.88(15)
O2 C8 O3 125.80(17)
O2 C8 C7 125.30(15)
O3 C8 C7 108.67(14)
O3 C9 C18 108.61(14)
O3 C9 C10 106.57(13)
C18 C9 C10 113.24(14)
O3 C9 H9 109.4
C18 C9 H9 109.4
C10 C9 H9 109.4
O4 C10 N2 123.49(16)
O4 C10 C9 120.39(16)
N2 C10 C9 116.10(15)
C16 C11 C12 120.87(17)
C16 C11 N2 119.26(16)
C12 C11 N2 119.87(16)
C13 C12 C11 119.23(18)
C13 C12 H12 120.4
C11 C12 H12 120.4
C12 C13 C14 119.96(19)
C12 C13 H13 120.0
C14 C13 H13 120.0
C15 C14 C13 120.71(18)
C15 C14 H14 119.6
C13 C14 H14 119.6
C16 C15 C14 119.37(18)
C16 C15 H15 120.3
C14 C15 H15 120.3
C15 C16 C11 119.81(18)
C15 C16 H16 120.1
C11 C16 H16 120.1
N1 C17 H17A 109.5
N1 C17 H17B 109.5
H17A C17 H17B 109.5
N1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C9 C18 Cl2 114.67(12)
C9 C18 Cl1 108.62(12)
Cl2 C18 Cl1 107.61(9)
C9 C18 Cl3 107.51(12)
Cl2 C18 Cl3 109.61(10)
Cl1 C18 Cl3 108.70(9)
N2 C19 H19A 109.5
N2 C19 H19B 109.5
H19A C19 H19B 109.5
N2 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C18 1.7795(17)
Cl2 C18 1.7590(18)
Cl3 C18 1.7794(19)
O1 C7 1.220(2)
O2 C8 1.185(2)
O3 C8 1.357(2)
O3 C9 1.438(2)
O4 C10 1.214(2)
N1 C7 1.340(2)
N1 C1 1.444(2)
N1 C17 1.470(2)
N2 C10 1.341(2)
N2 C11 1.441(2)
N2 C19 1.463(2)
C1 C6 1.380(3)
C1 C2 1.383(3)
C2 C3 1.389(3)
C2 H2 0.9300
C3 C4 1.376(3)
C3 H3 0.9300
C4 C5 1.376(3)
C4 H4 0.9300
C5 C6 1.384(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.525(3)
C9 C18 1.526(2)
C9 C10 1.544(2)
C9 H9 0.9800
C11 C16 1.379(2)
C11 C12 1.382(3)
C12 C13 1.371(3)
C12 H12 0.9300
C13 C14 1.382(3)
C13 H13 0.9300
C14 C15 1.380(3)
C14 H14 0.9300
C15 C16 1.374(3)
C15 H15 0.9300
C16 H16 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 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
C7 N1 C1 C6 -97.8(2)
C17 N1 C1 C6 85.0(2)
C7 N1 C1 C2 86.5(2)
C17 N1 C1 C2 -90.8(2)
C6 C1 C2 C3 -1.2(3)
N1 C1 C2 C3 174.54(16)
C1 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 1.5(3)
C3 C4 C5 C6 -1.6(3)
C2 C1 C6 C5 1.1(3)
N1 C1 C6 C5 -174.64(16)
C4 C5 C6 C1 0.3(3)
C1 N1 C7 O1 179.46(16)
C17 N1 C7 O1 -3.4(3)
C1 N1 C7 C8 -0.9(2)
C17 N1 C7 C8 176.25(15)
C9 O3 C8 O2 -1.2(2)
C9 O3 C8 C7 -176.03(13)
O1 C7 C8 O2 -84.0(2)
N1 C7 C8 O2 96.3(2)
O1 C7 C8 O3 90.81(18)
N1 C7 C8 O3 -88.85(18)
C8 O3 C9 C18 115.03(15)
C8 O3 C9 C10 -122.66(15)
C11 N2 C10 O4 173.17(18)
C19 N2 C10 O4 0.6(3)
C11 N2 C10 C9 -5.2(2)
C19 N2 C10 C9 -177.75(17)
O3 C9 C10 O4 -66.9(2)
C18 C9 C10 O4 52.4(2)
O3 C9 C10 N2 111.54(17)
C18 C9 C10 N2 -129.10(17)
C10 N2 C11 C16 -85.9(2)
C19 N2 C11 C16 86.8(2)
C10 N2 C11 C12 94.5(2)
C19 N2 C11 C12 -92.9(2)
C16 C11 C12 C13 2.2(3)
N2 C11 C12 C13 -178.16(17)
C11 C12 C13 C14 -0.7(3)
C12 C13 C14 C15 -0.9(3)
C13 C14 C15 C16 1.1(3)
C14 C15 C16 C11 0.4(3)
C12 C11 C16 C15 -2.1(3)
N2 C11 C16 C15 178.30(16)
O3 C9 C18 Cl2 54.13(16)
C10 C9 C18 Cl2 -64.04(17)
O3 C9 C18 Cl1 -66.27(15)
C10 C9 C18 Cl1 175.56(12)
O3 C9 C18 Cl3 176.28(10)
C10 C9 C18 Cl3 58.11(16)
