#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/49/7054986.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_7054986
loop_
_publ_author_name
'Chandrasekhara Rao, Lenka'
'Satish Kumar, Nandigama'
'Jagadeesh Babu, Nanubolu'
'Mitaram Meshram, Harshadas'
_publ_section_title
;
 A simple and efficient one-pot synthesis of 2-alkyl/aryl/pyridyl
 substituted 2H-chromenes
;
_journal_issue                   9
_journal_name_full               'New J. Chem.'
_journal_page_first              7164
_journal_paper_doi               10.1039/C5NJ01377A
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C17 H13 Cl2 N O4'
_chemical_formula_sum            'C17 H13 Cl2 N O4'
_chemical_formula_weight         366.18
_chemical_name_systematic
;
Ethyl 6,8-dichloro-2-hydroxy-2-(pyridin-4-yl)-2H-chromene-3-carboxylate
;
_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
_audit_update_record
;
2015-02-10 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                99.319(3)
_cell_angle_beta                 103.875(2)
_cell_angle_gamma                106.460(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7181(13)
_cell_length_b                   8.3117(14)
_cell_length_c                   14.132(2)
_cell_measurement_reflns_used    3682
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.64
_cell_volume                     817.9(2)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7594
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_T_max  0.9438
_exptl_absorpt_correction_T_min  0.8407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0554
_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)+(0.0615P)²+0.5634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                2434
_reflns_number_total             2869
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj01377a2.cif
_cod_data_source_block           ax65m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7054986.cif.
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7054986
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
C1 C 0.4876(4) 0.9712(4) 0.2379(2) 0.0443(7) Uani 1 1 d .
C2 C 0.6325(5) 1.1038(4) 0.3107(3) 0.0588(9) Uani 1 1 d .
H2A H 0.6790 1.2119 0.2983 0.071 Uiso 1 1 calc R
C3 C 0.7068(5) 1.0728(5) 0.4021(2) 0.0644(10) Uani 1 1 d .
C4 C 0.6408(4) 0.9166(4) 0.4235(2) 0.0565(8) Uani 1 1 d .
H4 H 0.6928 0.8998 0.4861 0.068 Uiso 1 1 calc R
C5 C 0.4941(4) 0.7826(4) 0.35010(19) 0.0401(6) Uani 1 1 d .
C6 C 0.4170(3) 0.8101(3) 0.25675(19) 0.0360(6) Uani 1 1 d .
C7 C 0.1984(3) 0.5061(3) 0.18883(18) 0.0313(5) Uani 1 1 d .
C8 C 0.2903(3) 0.4816(4) 0.29113(18) 0.0349(6) Uani 1 1 d .
C9 C 0.4236(4) 0.6110(4) 0.36348(19) 0.0407(6) Uani 1 1 d .
H9 H 0.4729 0.5894 0.4251 0.049 Uiso 1 1 calc R
C10 C -0.0115(3) 0.4793(3) 0.17081(18) 0.0289(5) Uani 1 1 d .
C11 C -0.0712(4) 0.5471(4) 0.2473(2) 0.0466(7) Uani 1 1 d .
H11 H 0.0151 0.6033 0.3106 0.056 Uiso 1 1 calc R
C12 C -0.2585(4) 0.5315(4) 0.2299(2) 0.0517(8) Uani 1 1 d .
H12 H -0.2957 0.5783 0.2828 0.062 Uiso 1 1 calc R
C13 C -0.3305(4) 0.3887(4) 0.0682(2) 0.0429(7) Uani 1 1 d .
H13 H -0.4194 0.3340 0.0055 0.051 Uiso 1 1 calc R
C14 C -0.1454(3) 0.3973(3) 0.07884(19) 0.0356(6) Uani 1 1 d .
H14 H -0.1119 0.3486 0.0249 0.043 Uiso 1 1 calc R
C15 C 0.2305(4) 0.3054(4) 0.3088(2) 0.0433(7) Uani 1 1 d .
C16 C 0.0156(5) 0.0165(4) 0.2354(3) 0.0561(8) Uani 1 1 d .
H16A H -0.0497 -0.0005 0.2855 0.067 Uiso 1 1 calc R
H16B H 0.1216 -0.0257 0.2503 0.067 Uiso 1 1 calc R
C17 C -0.1165(5) -0.0777(5) 0.1324(3) 0.0745(11) Uani 1 1 d .
H17A H -0.2168 -0.0302 0.1172 0.112 Uiso 1 1 calc R
H17B H -0.1693 -0.1982 0.1301 0.112 Uiso 1 1 calc R
H17C H -0.0484 -0.0652 0.0840 0.112 Uiso 1 1 calc R
Cl1 Cl 0.39258(12) 1.00569(11) 0.12213(7) 0.0622(3) Uani 1 1 d .
Cl2 Cl 0.89525(19) 1.24092(17) 0.49063(8) 0.1170(5) Uani 1 1 d .
H2O H 0.339(5) 0.421(4) 0.120(2) 0.048(9) Uiso 1 1 d .
N1 N -0.3900(3) 0.4530(3) 0.14139(19) 0.0439(6) Uani 1 1 d .
O1 O 0.2743(2) 0.6870(2) 0.18324(13) 0.0440(5) Uani 1 1 d .
O2 O 0.2248(3) 0.4056(2) 0.11088(13) 0.0381(5) Uani 1 1 d .
O3 O 0.3090(4) 0.2650(3) 0.38046(18) 0.0741(7) Uani 1 1 d .
O4 O 0.0813(3) 0.1971(3) 0.23576(16) 0.0500(5) Uani 1 1 d .
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
C2 C1 C6 120.7(3)
C2 C1 Cl1 119.7(2)
C6 C1 Cl1 119.6(2)
C3 C2 C1 118.7(3)
C3 C2 H2A 120.7
C1 C2 H2A 120.7
C4 C3 C2 122.3(3)
C4 C3 Cl2 120.2(3)
C2 C3 Cl2 117.4(3)
C3 C4 C5 119.1(3)
C3 C4 H4 120.5
C5 C4 H4 120.5
C4 C5 C6 119.8(3)
C4 C5 C9 123.0(3)
C6 C5 C9 117.1(2)
O1 C6 C1 117.8(2)
O1 C6 C5 122.7(2)
C1 C6 C5 119.5(2)
O2 C7 O1 106.81(19)
O2 C7 C10 110.4(2)
O1 C7 C10 102.15(18)
O2 C7 C8 113.3(2)
O1 C7 C8 111.4(2)
C10 C7 C8 112.09(19)
C9 C8 C15 119.5(2)
C9 C8 C7 122.3(2)
C15 C8 C7 118.1(2)
C8 C9 C5 122.6(2)
C8 C9 H9 118.7
C5 C9 H9 118.7
C11 C10 C14 117.6(2)
C11 C10 C7 119.5(2)
C14 C10 C7 122.8(2)
C12 C11 C10 119.7(3)
C12 C11 H11 120.1
C10 C11 H11 120.1
N1 C12 C11 123.6(3)
N1 C12 H12 118.2
C11 C12 H12 118.2
N1 C13 C14 124.4(3)
N1 C13 H13 117.8
C14 C13 H13 117.8
C10 C14 C13 118.6(2)
C10 C14 H14 120.7
C13 C14 H14 120.7
O3 C15 O4 123.5(3)
O3 C15 C8 124.2(3)
O4 C15 C8 112.2(2)
O4 C16 C17 106.8(3)
O4 C16 H16A 110.4
C17 C16 H16A 110.4
O4 C16 H16B 110.4
C17 C16 H16B 110.4
H16A C16 H16B 108.6
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C13 N1 C12 116.1(2)
C6 O1 C7 123.66(19)
C7 O2 H2O 111(2)
C15 O4 C16 119.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.380(4)
C1 C6 1.390(4)
C1 Cl1 1.730(3)
C2 C3 1.379(5)
C2 H2A 0.9300
C3 C4 1.364(5)
C3 Cl2 1.744(3)
C4 C5 1.395(4)
C4 H4 0.9300
C5 C6 1.395(4)
C5 C9 1.436(4)
C6 O1 1.344(3)
C7 O2 1.363(3)
C7 O1 1.474(3)
C7 C10 1.523(3)
C7 C8 1.523(3)
C8 C9 1.331(4)
C8 C15 1.486(4)
C9 H9 0.9300
C10 C11 1.373(4)
C10 C14 1.375(3)
C11 C12 1.372(4)
C11 H11 0.9300
C12 N1 1.331(4)
C12 H12 0.9300
C13 N1 1.324(4)
C13 C14 1.380(4)
C13 H13 0.9300
C14 H14 0.9300
C15 O3 1.199(3)
C15 O4 1.320(3)
C16 O4 1.440(4)
C16 C17 1.495(5)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
O2 H2O 0.83(3)
