# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s
_database_code_depnum_ccdc_archive 'CCDC 1036454'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
7-(diethylamino)-2-oxo-2H-chromene-3-carbohydrazide
_chemical_name_common            1a
_chemical_melting_point          433-438
_chemical_formula_moiety         'C14 H17 N3 O3'
_chemical_formula_sum            'C14 H17 N3 O3'
_chemical_formula_weight         275.31

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2120(18)
_cell_length_b                   12.624(3)
_cell_length_c                   12.927(3)
_cell_angle_alpha                94.78(3)
_cell_angle_beta                 109.99(3)
_cell_angle_gamma                105.42(3)
_cell_volume                     1336.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'SADABS(Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11095
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4609
_reflns_number_gt                3980
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0552P)²+0.1648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4609
_refine_ls_number_parameters     377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.37094(13) 0.21008(9) 1.22555(9) 0.0275(3) Uani 1 1 d . . .
N2 N 0.30689(13) -0.11563(9) 0.58434(9) 0.0284(3) Uani 1 1 d . . .
H2 H 0.2697 -0.1665 0.6173 0.034 Uiso 1 1 calc R . .
N3 N 0.30169(16) -0.14910(10) 0.47591(10) 0.0329(3) Uani 1 1 d . . .
H3A H 0.402(2) -0.1143(13) 0.4745(12) 0.039 Uiso 1 1 d . . .
H3B H 0.2251(19) -0.1225(12) 0.4269(13) 0.039 Uiso 1 1 d . . .
N4 N 0.89924(13) 0.48848(9) 0.76298(9) 0.0270(3) Uani 1 1 d . . .
N5 N 0.80165(14) 0.74503(10) 1.37557(9) 0.0318(3) Uani 1 1 d . . .
H5 H 0.7327 0.6789 1.3491 0.038 Uiso 1 1 calc R . .
N6 N 0.82009(17) 0.80199(11) 1.48069(10) 0.0363(3) Uani 1 1 d . . .
H6A H 0.926(2) 0.8406(14) 1.5127(13) 0.044 Uiso 1 1 d . . .
H6B H 0.764(2) 0.8522(14) 1.4672(13) 0.044 Uiso 1 1 d . . .
O1 O 0.28301(10) -0.04724(7) 0.90355(7) 0.0240(2) Uani 1 1 d . . .
O2 O 0.23042(11) -0.17647(7) 0.75952(8) 0.0302(2) Uani 1 1 d . . .
O3 O 0.42149(12) 0.06902(7) 0.59713(8) 0.0327(2) Uani 1 1 d . . .
O4 O 0.73383(10) 0.54885(7) 1.06811(7) 0.0268(2) Uani 1 1 d . . .
O5 O 0.64654(11) 0.56195(8) 1.20531(8) 0.0332(2) Uani 1 1 d . . .
O6 O 0.98580(12) 0.88513(8) 1.34805(8) 0.0363(3) Uani 1 1 d . . .
C1 C 0.29031(16) 0.12102(11) 1.27217(11) 0.0288(3) Uani 1 1 d . . .
H1A H 0.3312 0.1439 1.3531 0.035 Uiso 1 1 calc R . .
H1B H 0.3171 0.0539 1.2558 0.035 Uiso 1 1 calc R . .
C2 C 0.10701(17) 0.09453(12) 1.22498(13) 0.0356(3) Uani 1 1 d . . .
H2A H 0.0799 0.1610 1.2399 0.053 Uiso 1 1 calc R . .
H2B H 0.0598 0.0380 1.2597 0.053 Uiso 1 1 calc R . .
H2C H 0.0652 0.0677 1.1455 0.053 Uiso 1 1 calc R . .
C3 C 0.41947(16) 0.32444(11) 1.28706(11) 0.0304(3) Uani 1 1 d . . .
H3C H 0.3544 0.3267 1.3319 0.036 Uiso 1 1 calc R . .
H3D H 0.3976 0.3736 1.2339 0.036 Uiso 1 1 calc R . .
C5 C 0.38721(14) 0.18923(11) 1.12620(10) 0.0240(3) Uani 1 1 d . . .
C6 C 0.46878(15) 0.27726(11) 1.08375(11) 0.0261(3) Uani 1 1 d . . .
H6 H 0.5104 0.3502 1.1245 0.031 Uiso 1 1 calc R . .
C7 C 0.48636(15) 0.25586(11) 0.98443(11) 0.0261(3) Uani 1 1 d . . .
H7 H 0.5406 0.3148 0.9591 0.031 Uiso 1 1 calc R . .
C8 C 0.42479(14) 0.14692(10) 0.91857(10) 0.0228(3) Uani 1 1 d . . .
C9 C 0.34594(14) 0.06170(10) 0.96191(10) 0.0220(3) Uani 1 1 d . . .
C10 C 0.32577(15) 0.07987(10) 1.06140(10) 0.0237(3) Uani 1 1 d . . .
H10 H 0.2718 0.0204 1.0862 0.028 Uiso 1 1 calc R . .
C11 C 0.43012(15) 0.11847(10) 0.81278(10) 0.0236(3) Uani 1 1 d . . .
H11 H 0.4809 0.1745 0.7827 0.028 Uiso 1 1 calc R . .
C12 C 0.36371(14) 0.01185(10) 0.75288(10) 0.0227(3) Uani 1 1 d . . .
C13 C 0.28939(14) -0.07697(10) 0.80039(10) 0.0228(3) Uani 1 1 d . . .
C14 C 0.36618(15) -0.00953(11) 0.63860(11) 0.0242(3) Uani 1 1 d . . .
C15 C 0.77031(16) 0.38048(11) 0.71588(12) 0.0311(3) Uani 1 1 d . . .
H15A H 0.7669 0.3405 0.7764 0.037 Uiso 1 1 calc R . .
H15B H 0.7982 0.3366 0.6647 0.037 Uiso 1 1 calc R . .
C16 C 0.60172(17) 0.38807(12) 0.65377(12) 0.0353(3) Uani 1 1 d . . .
H16A H 0.5670 0.4233 0.7056 0.053 Uiso 1 1 calc R . .
H16B H 0.5268 0.3142 0.6198 0.053 Uiso 1 1 calc R . .
H16C H 0.6048 0.4315 0.5966 0.053 Uiso 1 1 calc R . .
C17 C 0.94072(18) 0.59463(12) 0.61468(11) 0.0359(3) Uani 1 1 d . . .
H17A H 0.8339 0.5520 0.5619 0.054 Uiso 1 1 calc R . .
H17B H 1.0130 0.6143 0.5757 0.054 Uiso 1 1 calc R . .
H17C H 0.9360 0.6615 0.6527 0.054 Uiso 1 1 calc R . .
C18 C 1.00263(17) 0.52522(11) 0.69962(11) 0.0297(3) Uani 1 1 d . . .
H18A H 1.0117 0.4597 0.6607 0.036 Uiso 1 1 calc R . .
H18B H 1.1109 0.5689 0.7521 0.036 Uiso 1 1 calc R . .
C19 C 0.91279(15) 0.55621(10) 0.85589(10) 0.0240(3) Uani 1 1 d . . .
C20 C 1.03027(15) 0.66525(11) 0.89623(11) 0.0268(3) Uani 1 1 d . . .
H20 H 1.0969 0.6914 0.8576 0.032 Uiso 1 1 calc R . .
C21 C 1.04569(16) 0.73123(11) 0.99049(11) 0.0284(3) Uani 1 1 d . . .
H21 H 1.1233 0.8018 1.0148 0.034 Uiso 1 1 calc R . .
C22 C 0.94828(15) 0.69654(10) 1.05264(10) 0.0252(3) Uani 1 1 d . . .
C23 C 0.83348(15) 0.58968(10) 1.01162(10) 0.0233(3) Uani 1 1 d . . .
C24 C 0.81296(15) 0.52076(11) 0.91663(10) 0.0250(3) Uani 1 1 d . . .
H24 H 0.7336 0.4509 0.8922 0.030 Uiso 1 1 calc R . .
C25 C 0.95869(16) 0.75889(11) 1.15171(11) 0.0267(3) Uani 1 1 d . . .
H25 H 1.0336 0.8304 1.1790 0.032 Uiso 1 1 calc R . .
C26 C 0.86312(15) 0.71852(10) 1.20929(10) 0.0253(3) Uani 1 1 d . . .
C27 C 0.74238(15) 0.60859(11) 1.16528(11) 0.0256(3) Uani 1 1 d . . .
C28 C 0.88711(16) 0.78989(11) 1.31583(11) 0.0267(3) Uani 1 1 d . . .
C4 C 0.59829(17) 0.36708(12) 1.36317(11) 0.0350(3) Uani 1 1 d . . .
H4A H 0.6184 0.3233 1.4207 0.053 Uiso 1 1 calc R . .
H4B H 0.6265 0.4441 1.3971 0.053 Uiso 1 1 calc R . .
H4C H 0.6631 0.3609 1.3199 0.053 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C5 1.3556(17) . ?
N1 C3 1.4624(18) . ?
N1 C1 1.4677(17) . ?
N2 C14 1.3330(18) . ?
N2 N3 1.4107(15) . ?
N2 H2 0.8600 . ?
N3 H3A 0.919(16) . ?
N3 H3B 0.932(16) . ?
N4 C19 1.3634(17) . ?
N4 C15 1.4650(19) . ?
N4 C18 1.4680(17) . ?
N5 C28 1.3372(17) . ?
N5 N6 1.4166(17) . ?
N5 H5 0.8600 . ?
N6 H6A 0.891(17) . ?
N6 H6B 0.914(17) . ?
O1 C9 1.3787(16) . ?
O1 C13 1.3800(15) . ?
O2 C13 1.2175(16) . ?
O3 C14 1.2397(15) . ?
O4 C27 1.3768(16) . ?
O4 C23 1.3823(15) . ?
O5 C27 1.2168(15) . ?
O6 C28 1.2336(17) . ?
C1 C2 1.5155(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.518(2) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C5 C10 1.4126(19) . ?
C5 C6 1.4284(19) . ?
C6 C7 1.3620(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.4135(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.4007(18) . ?
C8 C11 1.4053(18) . ?
C9 C10 1.3704(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.3601(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.4481(18) . ?
C12 C14 1.4886(18) . ?
C15 C16 1.518(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.5155(19) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.4128(18) . ?
C19 C20 1.428(2) . ?
C20 C21 1.3596(19) . ?
C20 H20 0.9300 . ?
C21 C22 1.4090(18) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(2) . ?
C22 C25 1.4060(19) . ?
C23 C24 1.3698(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.3643(19) . ?
C25 H25 0.9300 . ?
C26 C27 1.450(2) . ?
C26 C28 1.4956(19) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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
C5 N1 C3 121.40(11) . . ?
C5 N1 C1 122.22(11) . . ?
C3 N1 C1 116.14(11) . . ?
C14 N2 N3 123.67(11) . . ?
C14 N2 H2 118.2 . . ?
N3 N2 H2 118.2 . . ?
N2 N3 H3A 107.9(9) . . ?
N2 N3 H3B 106.6(9) . . ?
H3A N3 H3B 108.6(13) . . ?
C19 N4 C15 121.26(11) . . ?
C19 N4 C18 121.46(11) . . ?
C15 N4 C18 117.01(11) . . ?
C28 N5 N6 122.69(12) . . ?
C28 N5 H5 118.7 . . ?
N6 N5 H5 118.7 . . ?
N5 N6 H6A 104.4(10) . . ?
N5 N6 H6B 107.6(10) . . ?
H6A N6 H6B 107.9(15) . . ?
C9 O1 C13 122.64(10) . . ?
C27 O4 C23 122.90(10) . . ?
N1 C1 C2 112.30(11) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 112.45(12) . . ?
N1 C3 H3C 109.1 . . ?
C4 C3 H3C 109.1 . . ?
N1 C3 H3D 109.1 . . ?
C4 C3 H3D 109.1 . . ?
H3C C3 H3D 107.8 . . ?
N1 C5 C10 121.42(12) . . ?
N1 C5 C6 121.03(12) . . ?
C10 C5 C6 117.55(12) . . ?
C7 C6 C5 120.89(12) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 122.11(12) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C11 118.05(12) . . ?
C9 C8 C7 116.12(12) . . ?
C11 C8 C7 125.77(12) . . ?
C10 C9 O1 116.46(11) . . ?
C10 C9 C8 123.50(12) . . ?
O1 C9 C8 120.04(11) . . ?
C9 C10 C5 119.83(12) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
C12 C11 C8 122.32(12) . . ?
C12 C11 H11 118.8 . . ?
C8 C11 H11 118.8 . . ?
C11 C12 C13 119.46(12) . . ?
C11 C12 C14 118.67(12) . . ?
C13 C12 C14 121.85(11) . . ?
O2 C13 O1 115.24(11) . . ?
O2 C13 C12 127.39(12) . . ?
O1 C13 C12 117.38(11) . . ?
O3 C14 N2 122.37(12) . . ?
O3 C14 C12 120.55(12) . . ?
N2 C14 C12 117.07(11) . . ?
N4 C15 C16 114.84(12) . . ?
N4 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
N4 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 C17 114.17(11) . . ?
N4 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
N4 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
N4 C19 C24 121.36(12) . . ?
N4 C19 C20 121.07(12) . . ?
C24 C19 C20 117.56(12) . . ?
C21 C20 C19 120.71(12) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 122.37(12) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C23 C22 C25 118.13(12) . . ?
C23 C22 C21 116.10(12) . . ?
C25 C22 C21 125.76(12) . . ?
C24 C23 O4 116.70(11) . . ?
C24 C23 C22 123.49(12) . . ?
O4 C23 C22 119.81(11) . . ?
C23 C24 C19 119.76(12) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
C26 C25 C22 122.53(12) . . ?
C26 C25 H25 118.7 . . ?
C22 C25 H25 118.7 . . ?
C25 C26 C27 119.07(12) . . ?
C25 C26 C28 118.48(12) . . ?
C27 C26 C28 122.44(12) . . ?
O5 C27 O4 115.46(11) . . ?
O5 C27 C26 127.00(12) . . ?
O4 C27 C26 117.54(11) . . ?
O6 C28 N5 121.91(12) . . ?
O6 C28 C26 120.65(12) . . ?
N5 C28 C26 117.41(12) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.035
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, petroleum ether'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1036457'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
7-(diethylamino)-2-oxo-N'-phenyl-2H-chromene-3-carbohydrazide
_chemical_name_common            1b
_chemical_melting_point          474-476
_chemical_formula_moiety         'C20 H21 N3 O3'
_chemical_formula_sum            'C20 H21 N3 O3'
_chemical_formula_weight         351.40

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   13.1553(7)
_cell_length_b                   6.9401(4)
_cell_length_c                   21.0792(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.629(5)
_cell_angle_gamma                90.00
_cell_volume                     1812.67(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS(Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9709
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3485
_reflns_number_gt                2166
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0736P)²+0.2401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3485
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1421
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53480(12) -0.2737(2) -0.01747(9) 0.0596(5) Uani 1 1 d . . .
O2 O 0.83643(12) -0.2323(3) -0.04626(8) 0.0617(5) Uani 1 1 d . . .
O3 O 0.87160(11) 0.0374(2) 0.01139(7) 0.0460(4) Uani 1 1 d . . .
N1 N 0.96435(15) 0.6411(3) 0.12437(9) 0.0523(5) Uani 1 1 d . . .
N2 N 0.64660(15) -0.4190(3) -0.06289(10) 0.0550(5) Uani 1 1 d . . .
H2A H 0.7151 -0.4197 -0.0658 0.066 Uiso 1 1 d R . .
N3 N 0.58237(15) -0.5855(3) -0.07972(10) 0.0579(6) Uani 1 1 d . . .
H3A H 0.6260 -0.6851 -0.0800 0.069 Uiso 1 1 d R . .
C1 C 0.4824(2) -0.4437(5) -0.18961(15) 0.0745(8) Uani 1 1 d . . .
H1 H 0.5283 -0.3377 -0.1813 0.089 Uiso 1 1 calc R . .
C2 C 0.3977(3) -0.4595(6) -0.25055(16) 0.0959(11) Uani 1 1 d . . .
H2 H 0.3876 -0.3632 -0.2828 0.115 Uiso 1 1 calc R . .
C3 C 0.3293(3) -0.6137(7) -0.26385(17) 0.1018(13) Uani 1 1 d . . .
H3 H 0.2729 -0.6228 -0.3046 0.122 Uiso 1 1 calc R . .
C4 C 0.3454(3) -0.7544(6) -0.21614(18) 0.0937(12) Uani 1 1 d . . .
H4 H 0.2993 -0.8601 -0.2245 0.112 Uiso 1 1 calc R . .
C5 C 0.4289(2) -0.7416(5) -0.15596(14) 0.0718(8) Uani 1 1 d . . .
H5 H 0.4391 -0.8395 -0.1243 0.086 Uiso 1 1 calc R . .
C6 C 0.49771(18) -0.5854(4) -0.14196(13) 0.0539(6) Uani 1 1 d . . .
C7 C 0.62059(17) -0.2751(3) -0.02877(11) 0.0454(5) Uani 1 1 d . . .
C8 C 0.70092(16) -0.1178(3) -0.00396(10) 0.0414(5) Uani 1 1 d . . .
C9 C 0.80316(16) -0.1151(3) -0.01546(10) 0.0433(5) Uani 1 1 d . . .
C10 C 0.84576(16) 0.1862(3) 0.04689(10) 0.0389(5) Uani 1 1 d . . .
C11 C 0.74687(16) 0.1822(3) 0.05807(10) 0.0407(5) Uani 1 1 d . . .
C12 C 0.67628(16) 0.0281(3) 0.03149(11) 0.0442(5) Uani 1 1 d . . .
H12 H 0.6101 0.0255 0.0384 0.053 Uiso 1 1 calc R . .
C13 C 0.72570(17) 0.3365(4) 0.09483(11) 0.0503(6) Uani 1 1 d . . .
H13 H 0.6615 0.3380 0.1042 0.060 Uiso 1 1 calc R . .
C14 C 0.79721(18) 0.4843(3) 0.11712(11) 0.0495(6) Uani 1 1 d . . .
H14 H 0.7807 0.5844 0.1414 0.059 Uiso 1 1 calc R . .
C15 C 0.89635(16) 0.4884(3) 0.10404(10) 0.0423(5) Uani 1 1 d . . .
C16 C 0.92006(17) 0.3309(3) 0.06935(10) 0.0433(5) Uani 1 1 d . . .
H16 H 0.9856 0.3251 0.0617 0.052 Uiso 1 1 calc R . .
C17 C 1.0568(2) 0.6700(4) 0.10111(14) 0.0686(8) Uani 1 1 d . . .
H17A H 1.0464 0.5921 0.0612 0.082 Uiso 1 1 calc R . .
H17B H 1.0584 0.8039 0.0883 0.082 Uiso 1 1 calc R . .
C18 C 1.1605(3) 0.6213(7) 0.15083(17) 0.1070(13) Uani 1 1 d . . .
H18A H 1.1611 0.4875 0.1624 0.161 Uiso 1 1 calc R . .
H18B H 1.1721 0.6985 0.1904 0.161 Uiso 1 1 calc R . .
H18C H 1.2169 0.6459 0.1325 0.161 Uiso 1 1 calc R . .
C19 C 0.9410(2) 0.7972(4) 0.16422(12) 0.0561(6) Uani 1 1 d . . .
H19A H 0.8658 0.8337 0.1440 0.067 Uiso 1 1 calc R . .
H19B H 0.9845 0.9083 0.1622 0.067 Uiso 1 1 calc R . .
C20 C 0.9624(2) 0.7460(4) 0.23738(12) 0.0639(7) Uani 1 1 d . . .
H20A H 1.0377 0.7184 0.2587 0.096 Uiso 1 1 calc R . .
H20B H 0.9206 0.6348 0.2400 0.096 Uiso 1 1 calc R . .
H20C H 0.9424 0.8524 0.2598 0.096 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 C7 1.229(2) . ?
O2 C9 1.210(2) . ?
O3 C9 1.382(3) . ?
O3 C10 1.383(2) . ?
N1 C15 1.360(3) . ?
N1 C19 1.465(3) . ?
N1 C17 1.471(3) . ?
N2 C7 1.341(3) . ?
N2 N3 1.405(3) . ?
N2 H2A 0.9227 . ?
N3 C6 1.407(3) . ?
N3 H3A 0.9000 . ?
C1 C6 1.371(4) . ?
C1 C2 1.394(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.487(3) . ?
C8 C12 1.360(3) . ?
C8 C9 1.445(3) . ?
C10 C16 1.370(3) . ?
C10 C11 1.398(3) . ?
C11 C13 1.403(3) . ?
C11 C12 1.404(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.421(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.407(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.454(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.514(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C9 O3 C10 123.30(15) . . ?
C15 N1 C19 120.96(18) . . ?
C15 N1 C17 122.12(19) . . ?
C19 N1 C17 116.5(2) . . ?
C7 N2 N3 120.52(18) . . ?
C7 N2 H2A 118.0 . . ?
N3 N2 H2A 119.8 . . ?
N2 N3 C6 117.1(2) . . ?
N2 N3 H3A 107.6 . . ?
C6 N3 H3A 107.5 . . ?
C6 C1 C2 119.6(3) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 N3 124.0(2) . . ?
C5 C6 N3 117.1(3) . . ?
O1 C7 N2 121.8(2) . . ?
O1 C7 C8 121.1(2) . . ?
N2 C7 C8 117.16(18) . . ?
C12 C8 C9 119.3(2) . . ?
C12 C8 C7 117.85(18) . . ?
C9 C8 C7 122.81(19) . . ?
O2 C9 O3 115.54(18) . . ?
O2 C9 C8 127.3(2) . . ?
O3 C9 C8 117.14(18) . . ?
C16 C10 O3 117.25(17) . . ?
C16 C10 C11 123.54(19) . . ?
O3 C10 C11 119.20(19) . . ?
C10 C11 C13 116.5(2) . . ?
C10 C11 C12 118.43(19) . . ?
C13 C11 C12 125.05(19) . . ?
C8 C12 C11 122.57(19) . . ?
C8 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C14 C13 C11 121.5(2) . . ?
C14 C13 H13 119.3 . . ?
C11 C13 H13 119.3 . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
N1 C15 C16 122.13(19) . . ?
N1 C15 C14 120.3(2) . . ?
C16 C15 C14 117.6(2) . . ?
C10 C16 C15 119.47(19) . . ?
C10 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 N1 114.1(2) . . ?
C18 C17 H17A 108.7 . . ?
N1 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
N1 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 114.0(2) . . ?
N1 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
N1 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C6 90.3(3) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C2 C1 C6 N3 178.2(2) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C4 C5 C6 N3 -178.8(2) . . . . ?
N2 N3 C6 C1 7.8(3) . . . . ?
N2 N3 C6 C5 -174.5(2) . . . . ?
N3 N2 C7 O1 -8.0(3) . . . . ?
N3 N2 C7 C8 171.01(19) . . . . ?
O1 C7 C8 C12 -0.2(3) . . . . ?
N2 C7 C8 C12 -179.18(19) . . . . ?
O1 C7 C8 C9 179.3(2) . . . . ?
N2 C7 C8 C9 0.3(3) . . . . ?
C10 O3 C9 O2 178.69(18) . . . . ?
C10 O3 C9 C8 -1.3(3) . . . . ?
C12 C8 C9 O2 -179.3(2) . . . . ?
C7 C8 C9 O2 1.2(4) . . . . ?
C12 C8 C9 O3 0.7(3) . . . . ?
C7 C8 C9 O3 -178.75(19) . . . . ?
C9 O3 C10 C16 -178.44(18) . . . . ?
C9 O3 C10 C11 1.6(3) . . . . ?
C16 C10 C11 C13 -0.4(3) . . . . ?
O3 C10 C11 C13 179.52(18) . . . . ?
C16 C10 C11 C12 178.8(2) . . . . ?
O3 C10 C11 C12 -1.2(3) . . . . ?
C9 C8 C12 C11 -0.4(3) . . . . ?
C7 C8 C12 C11 179.0(2) . . . . ?
C10 C11 C12 C8 0.7(3) . . . . ?
C13 C11 C12 C8 179.9(2) . . . . ?
C10 C11 C13 C14 1.4(3) . . . . ?
C12 C11 C13 C14 -177.8(2) . . . . ?
C11 C13 C14 C15 0.0(4) . . . . ?
C19 N1 C15 C16 -175.99(19) . . . . ?
C17 N1 C15 C16 11.5(3) . . . . ?
C19 N1 C15 C14 4.4(3) . . . . ?
C17 N1 C15 C14 -168.1(2) . . . . ?
C13 C14 C15 N1 177.3(2) . . . . ?
C13 C14 C15 C16 -2.3(3) . . . . ?
O3 C10 C16 C15 178.20(17) . . . . ?
C11 C10 C16 C15 -1.9(3) . . . . ?
N1 C15 C16 C10 -176.43(19) . . . . ?
C14 C15 C16 C10 3.1(3) . . . . ?
C15 N1 C17 C18 -104.0(3) . . . . ?
C19 N1 C17 C18 83.1(3) . . . . ?
C15 N1 C19 C20 75.7(3) . . . . ?
C17 N1 C19 C20 -111.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.039
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_preparation       Luminescent
